Sunteți pe pagina 1din 507

Contents

A SaaS Startups Journey to $100,000 a Month

5 Early Wins That Got Our SaaS Startup 1,000 Beta Users

10

3 Early Fails That Nearly Killed Our Startup

17

7 Lessons We Learned Going from Zero to $30k/Month in Under a Year

29

The Pricing Model That Increased Our Free Trial Signups by 358% (and Revenue by 25%)

39

How We Grew Our Blog to 5,000+ Subscribers in Five Weeks

47

How We Got 1,000+ Subscribers from a Single Blog Post in 24 Hours

55

How We Failed Our Way to a Day on the Front Page of Hacker News

67

Why I Turned Down $5 Million in VC Funding

76

100,000+ Reasons To Be Thankful

83

Why I Dont Stress Over Competition Anymore

85

Announcing the 2013 SaaS Small Business Conversion Survey

93

Our Metrics REVEALED: Revenue, Churn, Conversions and More

98

Results Of The 2013 SaaS Small Business Conversion Survey!

104

How A Single Email Made Customers 350% More Likely To Convert

109

How we got more than 1,500 survey responses with a last-minute scramble

114

What I Fear Most As a Founder

121

How We Grew Our Customer Exit Survey Responses by 785%

127

The 25% Discount that Cost Us $12,000 (Plus, a Big Announcement)

133

Unlock $10,000 in Free SaaS Apps and Help Us Give Away $50,000,000

140

The Meltdown That Brought Our Startup to Its Knees for 15 Hours

145

Dont Make THIS Customer Communication Mistake

157

How We Grew Conversions 100% by Rethinking Our Design Strategy

161

How Our Startup Beat Burnout

174

The 3 Deadliest Challenges of Scaling a Startup

181

3 Lessons Learned From Testing Hundreds Of Onboarding Emails

190

How Our Startup Hires Top Talent Without Bidding Against Google (PLUS, We're Hiring!)

198

What I Did When I Couldn't Find a Technical Co-Founder

205

Lessons Learned Growing our Startup to $50,000 in Monthly Revenue

212

The Pros & Cons of Being a Remote Team (& How We Do It)

228

8 Things Every Non-Technical Founder Should Know How to Do

237

Its Lonely Being a Single Founder

248

The ROI of Blogging: What the Groove Blog is Worth to Our Startup

257

The Simple Test That Increased Our Referrals by 30%

266

Why Bug Reports and Feature Requests Dont Overwhelm Us Anymore

272

Lessons Learned Sending a Net Promoter Survey to 4,000 Users

279

Our Startups 12-Month Growth Strategy

286

How Weve Reached More Than 1 Million People by Guest Blogging

295

6 A/B Tests That Did Absolutely Nothing for Us

304

Why We Killed One of Our Biggest Features to Grow Our Business

309

Six Months Later: Weve Given Away More Than $50,000,000 in SaaS Apps

315

Why Investor Updates Are Important (Even If You Dont Have Investors)

321

The Value of the Hustle: How We Saved $25,000 by Thinking Outside the Box

327

Feel Guilty About Taking a Vacation In Your Startup? Heres Why We Dont.

333

How Sharing Feature Release Dates Turned Us Into Liars

339

14 Ways Our Remote Team Stays Sane Working From Home

344

Lessons Learned Building a Startup Team

354

The Power of Testimonials (And How We Get Great Ones)

363

How Ive Become A Better Founder By Practicing Patience

371

Why Were Doubling Down on Content (Plus, a Big Announcement)

378

How We Got 2,000+ Customers by Doing Things That Didnt Scale

387

We Deleted Our Facebook Page. Heres Why.

396

Customer Development for Startups: What I Learned Talking to 500 Customers in 4 Weeks

403

SEO for Startups How We Got Over Our Fear of SEO

415

Performance Metrics

429

How We Choose, Build and Launch Partner Integrations to Grow Our Business

438

How We Increased Our Net Promoter Score by 45%

453

Why I Walked Away From a $12M Acquisition Offer 18 Months After Our Startups Launch

465

How We Created a Product Explainer Video That Actually Got People to Buy

474

How Gratitude Has Made Me a Better Founder

487

Lessons Learned Growing a Startup From Zero to $100k/month in 2 Years

493

A SaaS Startups Journey


to $100,000 a Month
September 25, 2013

That damn dangling carrot Always in


sight, never within reach. Until now.
My last company, Bantam Live, was acquired early on, before we had a chance or
needed to truly scale our business. Those early acquisition offers can be damn
tempting, and I dont fault any hustling entrepreneur for jumping on one.
But this time, things are different. With Groove, I want to build something bigger.
Not a quick exit. Not a VC-driven feet-to-the-fire sprint to the finish. This time,
Im in it for the long haul.
The game Im in is maximum happiness for the maximum amount of
time. What I found is one of the things that makes me really happy is
to work on stuff that I care about with people I really like working
with, with the independence of nobody telling me what the fuck to
do.
- David Heinemeier Hansson, Creator of Ruby on Rails, partner at
37signals

Thats not to say the temptation isnt there. I wasted six months entertaining
offers to buy Groove while we were in beta. It was a distraction, and it was a
failure on my part to ignore the bigger picture. It wasnt our first fail as a business,
4

and it wont be our last. But failures are a huge part of the startup journey, and
that journey is what this blog will be about.

Are you working your ass off to grow your


startup?
This is the blog I wish I had read the first time I started a company. Its going to
cover the lessons we learn from our own experiences, including our tests, our
wins and our fails, backed up with real numbers. Everything from design,
development, strategy, marketing, sales, growth hacking, hiring, fundraising,
culture, customer support and more.

Now, Im not saying that there arent any good places online and offline for
you to learn about these things. There are tons of amazing resources out there.
More successful entrepreneurs, smarter analysts and better writers. I know,
because I read as many of them as I can, and Ill be sharing the best of what I find.
But what were going after with this blog is a different perspective. A view from
the drivers seat, with actionable takeaways that you can put directly into your
Basecamp project or Trello board to test in your own startup. You wont find any
armchair analysis here; everything we write about will be hard-earned lessons
5

from our own experience, as we learn them on our way to $100,000 in monthly
revenue.

Why $100,000 in Monthly Revenue?


Because goals matter. And big milestones like that one give our whole team a
massive red bullseye to aim for, every time we look at our roadmap.
One of the biggest (and most counter-intuitive) lessons Ive learned as an
entrepreneur is that just about the hardest way to make more money is to try to
make more money.
Confusing, I know.
Rather, the easiest way to make more money is to provide more value. Our
customers dont care that we want to make more money, nor should they. Our
customers do care that we want to improve their lives, help them to do their jobs
better, and make their businesses succeed. And that, theyre willing to pay for.

Where Our Journey Starts

Were in the same place as a lot of you: in transition. Weve been developing,
designing and just barely starting to promote. As Marc Andreesen puts it, the life
of a startup can be divided into two parts: Before Product/Market Fit, and After
Product/Market Fit.

When you are BPMF, focus obsessively on getting to product/market


fit. Do whatever is required, including changing out people,
rewriting your product, moving into a different market, telling
customers no or yes when you dont want to, raising that fourth
round of highly dilutive venture capital.
- Marc Andreesen, VC

We launched to the public about 11 months ago, and the story up until recently has
been one of focusing obsessively on getting to product-market fit. Weve
redesigned, redeveloped, restrategized, and apologized for hiccups more times
than we can count.
Then, a couple of months ago, something awesome happened. The feedback
became more positive. We were getting more and more emails from customers
who loved our product, and fewer complaints about bugs and UX issues.
We ran the Product/Market Fit survey pioneered by Sean Ellis, and the results
confirmed what we suspected:

If you find that over 40% of your users are saying that they would be
very disappointed without your product, there is a great chance
you can build sustainable, scalable customer acquisition growth on
this must have product.
- Sean Ellis

We were on our way to product/market fit.


Finally, our customers were proud to share Groove with their friends and
coworkers. Word of mouth began to spread, and new users started to sign up at a
pace we hadnt seen before; first at a steady trickle, and now at a strong, healthy
clip.

What You'll Learn


Starting with our next post, well outline how exactly we got to where we are
today. Well talk about the strategies and tactics we applied, and the lessons we
learned, including:
How we got 1000+ private beta signups in just 7 days, without getting
Crunched.
Why we passed on a $5 million raise from VC's 6 months in.
How we wasted $50,000 designing the wrong website (and how you can avoid
the same mistake)
Fair warning: there are over a dozen big lessons like the ones above that weve
learned up until now. This next post will be very long. But its going to be packed
with detailed explanations, and Im not exaggerating when I say that if I had this
information before we launched, wed probably be at $100,000/month by now. If
you get even a fraction of that benefit from reading it, Ill be happy.
After next weeks post, well shift to a more real-time perspective on our mission.
8

Weve got hundreds of tests were going to run, and whether we win or lose, well
be sharing the results with you. And if all goes well, well continue to share our
insights and lessons all the way to $100,000 and beyond.

So Whats Next?
Hopefully, youll join us on our journey. Its totally free, and you dont have to be a
Groove customer (though youre more than welcome to sign up for a free trial
here).
Well be releasing a new post each week, starting with the one outlined above. To
get each post emailed to you as soon as its published, sign up for the $100K
mailing list below.
See you next week. Have something you want to learn more about? Let me know
in the comments below or hit me up on Twitter.

5 Early Wins That Got Our SaaS


Startup 1,000 Beta Users
October 3, 2013

Last week we launched a new series


about our journey to $100K a month.
Now let's go back to where it all began
In May of 2011, I was talking on the phone with a fairly well-known VC.
We had been introduced through mutual friends, and I was telling him about my
plans for Groove.
Why on earth would you want to enter this space?
Youll be fighting an uphill battle against huge players. Zendesk,
Desk.com, plus an overcrowded market of smaller companies.
That was true.
There was no doubt that wed have a long road ahead of us if we were going to
become competitive. Wed be far from the only new kids on the block.
But, I explained, that was exactly why I wanted to build customer support
software. Businesses were no longer relying on email to do support, and the
success of the incumbents proved that a market for a solution exists. Plus, Ive
10

always loved going after competitive markets I see a competitive frenzy as proof
that theres big demand for a great solution.

The problem with the crowded customer support software market was that none
of the solutions seemed all that great to me.
That doesnt mean there weren't great products available; it just means that there
wasnt one that was perfect for me. And if I was in that boat, I suspected others
were too.
At my last company, BantamLive, we looked at a dozen options for support
software, and ultimately chose Zendesk, a product that many people love. But as
I a career-long product guy with no customer support experience used it, I
found it clunky, and, well, enterprise-y. As naive as it may be, Ive always thought
that business software shouldnt feel like business software. Why cant I get the
Apple experience at work?
If youre reading this, youre probably a hustler, and you know exactly what I mean
when I say that the product I wanted didnt exist, so I knew I had to build it.
As soon as my check from the acquisition cleared, I put $250,000 into a business
checking account, tapped a team of developers and designers, and got to work.
11

Groove was born.


Takeaway: Dont let competition deter you. Competition means that theres
demand in the marketplace. Just because there are solutions out there, doesnt
mean theyre right for everyone. You can create a profitable company serving a
small niche in a competitive market.

The 5 Early Wins that Kept Us Alive


During those initial months of product development, we had some wins, as well as
a few losses. Some of them were our own doing, and others happened organically.
It didnt take very long to get to (what, in hindsight was) a crude beta product, and
a small group of non-paying users. A few things helped us get there:

1. Our PR Strategy (and our full outreach list)

We were fortunate to get picked up early by The Next Web. This brought us a few
hundred email signups from folks who were interested in joining our private beta.
How did we get picked up by a major tech blog?
12

We laid out a PR plan and ended up emailing about 40 outlets. See the full list
here, and feel free to use it for your own outreach note that some of these may
be outdated.
The thing is, PR plans have a funny way of shriveling up and dying when you
expose them to reality, and we only got one response, which came from
TNW though, to be fair, they were our first pitch, and we were excited to get
covered.
Still no love from TechCrunch, which at the time, we naively looked at as so
many do as the pinnacle of startup PR success.
Takeaway: Theres more to PR than pitching TechCrunch. Too many startups see
TechCrunch as a success metric, but there are hundreds of great press outlets. We
shared more than 40 of them right here.

2. Twitter Buzz (and the value of Twitter traffic)


After the TNW piece went live, Twitter which hadnt been an influence on us
until that point exploded.

People Tweeted links to the post (and to Groove), and while Twitter traffic didnt
convert nearly as well as some other channels, we did get a handful of free trial
13

signups, which led to more Tweets, which led to more signups, and on and on.
We didnt track this at the time (doh!), but I suspect those that found us on
Twitter were more engaged in social media; thus more likely to Tweet about us. I
can't prove it, but my gut says this was very high-value traffic for us.
Takeaway: Twitter is no longer optional. Ill admit, I dont personally like using
Twitter. But as a business, you must go to where your customers are. When the
TNW piece brought us Twitter buzz, we realized how valuable that traffic was, and
the platform is now a big part of our strategy.

3. A Viral Sign-Up Form (and how we hacked beta invites)


After testing a couple of approaches, we settled on a signup flow that required
users to invite three friends in order to gain access to our beta.

While the number of initial subscribers (non-invitees) dropped when we did this,
we got about 30% more subscribers per day after invitees responded to their
friends posts on Facebook and Twitter.

14

Takeaway: Customer Acquisition doesnt have to happen one user at a time.


Think about how you can leverage one user or subscriber, and double or triple the
impact.

4. Blogging (and an evolving content strategy)


To say we were blogging back then would be a massive overstatement, but we
did write a few pieces that got shared quite a bit, and brought us some new users.
Funnily enough, the piece that brought in the most new users was about how we
had just gotten a whole bunch of users. It even made it to #1 on Hackers News for
a half a day! Can you tell I was excited? :)

We built our early blogging strategy off of studying what worked on the blogs that
we read ourselves, and came up with a 44-point checklist for what we thought
would work. To an extent, it did work, but not enough to justify the resources
needed to stay on course, so now we use a modified approach. And yes, well be
sharing it.
Takeaway: Start blogging, ASAP. Think about what content your target customers
would find valuable, and give them lots of it, for free. For early stage startups, its
one of the most cost effective ways to establish your brand and build an audience.

5. Design, Design, Design (the mantra that saved us)


Weve always focused hard on design; its been the driving force behind our
product since the beginning, and the biggest differentiator we have from our
competitors. As Tom Tunguz says so eloquently, good design is telepathic, and
that was, is, and always will be our goal.
Nearly all of the positive early feedback related to our design and user interface.
15

People were more forgiving of our buggy product because the beautiful UI was a
pleasure to use, and that kept us alive for months.
Takeaway: Dont compromise on what makes people love you. For us, it was
design. For you, it might be price, speed, service or one of a thousand other
possible differentiators. Protect that part of your business with everything youve
got, because it will be what saves you when everything else is going wrong.

Whats Next?
Like almost every growing startup, we had our share of early fails too.
Next week Ill go into detail about the three biggest mistakes we made, each of
which cost us dearly in the two most important currencies we have: time and
money.
Well cover:
Burning through $50k on design for nothing.
Letting outside distractions set us back six months.
Adding feature after feature until our app was on its deathbed.
Well be releasing a new post each week. To get each post emailed to you as soon
as its published, sign up for the $100K mailing list below.
See you next week. Have something you want to learn more about? Let me know
in the comments below or hit me up on Twitter.

16

3 Early Fails That Nearly


Killed Our Startup
October 10, 2013

Last week we detailed what went right in


Grooves early days. Now lets take a look
at what went wrong
If youre part of an early-stage startup, you know how fragile a young business can
be. Without sustainable revenue or an established brand to fall back on, it doesnt
take a whole lot to crash and burn.
In Grooves early days, we nearly crashed and burned not once, but three times.
What follows is exactly what happened, and what you can learn to avoid making
the same mistakes.

The Temptation Of Selling Out


Soon after our beta launch and the explosion of attention from our TNW coverage
(detailed in last weeks post), I received two early acquisition offers that wouldve
been a hell of a paycheck for the six months of work our team did.

17

Overnight, the way that I looked at Groove changed.


The siren song of an early exit can be damn powerful, and instead of thinking
about the future of Groove, I began to think about how to optimize an acquisition
payout.
I cut back on costs, and product development more or less stalled while I took
meeting after meeting, working out the terms that would make us all rich.
This lasted for months. As I walked away from the 10th meeting in the long,
drawn-out process, I couldnt help but think I was doing something wrong.
I started thinking about the reason that I founded Groove in the first place. After
my first acquisition, I promised myself that my next business would create a longterm, sustainable lifestyle.
I wanted to build a company that provided my team and me the means to do
everything that we love both in and out of the office. Burning out and selling
every three years isnt the way to do that. Once I realized that, I knew I had to end
our acquisition talks.
But as I took stock of where we were, I came to the painful realization that this
distraction had cost us dearly. I wasted almost a year entertaining these offers,
distracting the team from product development and crippling our productivity.
18

We also missed some important opportunities; we were chosen for the Under The
Radar conference, and didnt even attend because of the acquisition talks I didnt
think it was necessary.
So a year behind on development, and no longer looking for a way out, we recommitted ourselves to building a sustainable, growing business.
Disclaimer: I know that acquisition offers arent a problem that most early-stage
startups deal with. Hell, most founders would love to have my problems, and I fully
admit that I really, truly have nothing to complain about.
But the issue here isnt acquisition offers; its back-office distractions.
For many startups, that means deciding on whether or not to bring on a cofounder, hiring decisions and going back on forth on figuring out what payroll and
accounting software to use.
No matter how big or small, these are distractions that keep you from your
number one priority, which should be building your business.
What I learned: Focus is absolutely essential. No business can afford to be
stagnant for months while the founder waffles on his dreams. The grind will wear
you down and cloud your judgment. Know what you got into this game for, and try
to never forget it.

Creating a Monster (Product)


We had a wishlist of features that we thought would add value to our product.
The only problem is, that wishlist turned into a must have list, and it grew each
time we thought of something we liked.
Just like the acquisition setback, we lost sight of what we had set out to do: build a
simple, elegant solution that wasnt like the existing, cumbersome products.
Nonetheless, slowly but surely we added feature after feature, pushing our launch
date back with each one.

19

I made the mistake of thinking that more features would result in more value,
which flew directly in the face of the product I set out to build: a simple
alternative to the incumbents.
Unfortunately, when youre staring down the end of your runway and facing the
reality that you need to find some customers or your company will die, logic has
the tendency to fly out the window.
I was sure that the more we offered, the more users we could be helpful to.
Unfortunately, the opposite turned out to be true.
We were trying to figure out why beta users were abandoning our product so
quickly after signing up, when it hit me like a ton of bricks.
Except instead of bricks, it was a ton of features.
As an example, heres what our onboarding process looked like:

20

Who, in reality, could possibly want to go through a process like that, just to get
the value they had just been promised was only a few clicks away?
The Need Help? in the bottom right corner is almost funny to me now.
Anyone would need help trying to navigate that monster. And that monster
existed because we had added so many features, and tried to push every single
one of them on our users.
We were approaching the end of our runway. Not only that, but our product was
becoming what we hated most: a big bag of bloat. Sure, we had lots of features,
gamification, ancillary apps and more, but we also didnt have a single paying
customer.
We would soon strip down the product (more on that later) and finally begin to
get our users engaged. The only thing standing in our way? Getting more people
to actually sign up...
What I learned: Focus on the single thing you do best, and be the best in the
marketplace for your customers not for everyone else. Trying to be everything
to everyone is the easiest way to become right for no one, and we were headed in
that direction.

21

The Terrible, Horrible, Inexcusable $50,000


Mistake That No Startup Should Ever Make
Your marketing site is supposed to tell the story of your product, right?
Well, as I painfully learned, not exactly. Your marketing site is supposed to tell the
story of your targets pain points, to show them the solution, and to convert them
into users.
Nonetheless, when we started out, I assumed that we needed to tell our story.
The whole story.
Now, while we were in private beta, we had a very simple site that actually worked
really well at converting visitors to beta subscribers.

Not terrible, right?


But as I was getting ready to launch Groove to the public, a paralyzing fear started
to take hold: even if our product was awesome, how could anyone take us
seriously when our site looks so spartan compared to the competition?

22

Zendesk, Desk.com and UserVoice all had (and still have) big, robust marketing
sites. If people looked at Grooves simple little landing page, theyd think we must
be some kind of chumps. Right?
This is where everything starts going wrong.
First, we had to do some research.
But not just any research. We couldnt risk being underprepared, so our research
included a 42-page competitive canvas, a number of messaging and positioning
exercises, and a comprehensive market gap analysis that I now wonder how we
ever made sense of.
That research took us weeks to complete, and during that time, we didnt mock up
a single design.
But, armed with massive amounts of research to back up our strategy, we were
ready to get started. We set out to build the best damn marketing site, period.
Except that we thought best meant most impressive.
Everyone else had long-scroll landing pages with carousels and dynamic images.
So we would, too.
Here are a couple of our earliest sketches.

23

Happy that our design plan covered the scope of everything a marketing site
would ever need to have, I gave the go-ahead to push forward.
Of course, the bigger a site is, the longer it takes to build. And as our site grew and
grew, the fact that we didnt have a single paying customer yet didnt matter; the
payroll checks still had to be cut. I was burning through our runway as if we had
revenue, and the idea of spending a week getting our icon sets right didnt even
phase me. It had to be perfect.
Hindsight is 20/20. Hindsight can also be incredibly painful. The decisions I was
making could not have been dumber.
We built page after page and section after section, forging on without testing any
of them on a single user.

24

Still, as wrong as my vision was, five months after we started, my vision became
reality. Heres what that the final site looked like:

It sure was pretty to look at. So we flipped the switch, and the site went live.
The traffic came, and after the first 2 weeks, I looked at our analytics.
You know that feeling in your gut when you begin to think that you may have
made a huge mistake? Yeah.

25

Our conversion rate was less than 2%.


Nobody was even scrolling past the fold. The site was overwhelming our visitors,
and the navigation we were asking of them was simply too much work.
But it wasnt just the design. We also suffered on the positioning end: because we
had two features that we thought were equally valuable, we made the painful error
of thinking that we could position ourselves as a product company offering a
suite of support products, rather than simply a customer support company. Our
messaging was scattered and our visitors were confused; nobody was sure what
we actually did.
Realizing that if our conversion rate continued to suck this badly, wed soon have
to fold, I had a difficult decision to make. But looking at our metrics and visitor
behavior, the only way out of this mess would be to abandon five months of
painstaking (and painfully expensive) work.
So we swallowed our pride and put up a three-page (landing, pricing and signup)
site that was hyper-focused on the benefits of our helpdesk platform, and nothing
else. No live chat. No ancillary features. The site took three days to build.

Conversions tripled overnight.

26

Perhaps the most painful part of this lesson is how closely the new, effective site
resembles our original beta site. If we had simply made tweaks to that one, added
pricing and launched it to the public, I suspect we would be in a completely
different place today.
Since the turnaround, weve gone through many iterations to optimize
conversions, but each one was tested early and often. No comprehensive research
exercises. Just build it, ship it, test it, and iterate.
Ultimately, our mistake wasnt that we were building the wrong marketing site.
The mistake was being so damn sure our initial assumptions were right, that we
thought we had to do whatever it took to deliver on those assumptions. What it
took was $50,000 and five months of work.
Wasting $50,000 hurts any business. Wasting $50,000 only to ultimately cripple
your business? That cuts a lot deeper.
What I learned: Swallow your pride, and test your assumptions vigorously. Your
customers dont care about your grand plans for the business, they care about you
solving their problems and providing more value than you charge for. Thats it.
Distill your messaging so that its incredibly clear what value youre providing.
Whatever you think you know, theres a great chance that youre wrong, so test
fast before betting the house on a single strategy. And please, please, please dont
spend as much time as we did on market research.

Stripping Down and Turning a Corner


We exited beta testing and launched to the public in November of 2012, raising a
$1M convertible note from a group of angel investors our terms were much
more favorable and less restrictive than the ones we explored with VCs, and the
level of trust that I had in our investors was much higher from the start. Simply
put, they have more skin in the game.
Though we werent quite ready for the onslaught of signups, TNW covered the
launch. And while we hadnt yet found product/market fit, we were obsessive
about tracking user behavior and feedback, so we were able to learn a lot from the
new wave of traffic.
Over the next few months, the feedback we were getting was clear: while the
design was awesome, the product was more than users needed, and it was getting
more complicated each time we enhanced it.
We had disproved our initial hypothesis about the features we thought users
wanted, and learned what our users actually wanted: simple ticketing and

27

knowledge base software. So armed with that data, we stripped down the product
to its core, moved our ancillary features into the App Store, and simplified the
user experience.
That simplification was a major turning point for us.

Whats Next?
The past eleven months since our public launch have been a whirlwind, and Ive
got the eye wrinkles to prove it. But weve learned an incredible amount in a short
time.
Next week, Ill be sharing how we turned a $0/month company into a
$30K/month company. Ill detail the strategies that we used, and the ones that we
plan to use moving forward on our road to $100K and beyond.
Well cover:
The specific blogs that I study every week to be a better entrepreneur
The single Tweet that brought us 100 new trial signups
The stupid-simple A/B test we ran that boosted conversions nearly 300%
Well be releasing a new post each week. To get each post emailed to you as soon
as its published, sign up for the $100K mailing list below.
See you next week.

28

7 Lessons We Learned Going from


Zero to $30k/Month in Under a Year
October 17, 2013

After some early wins and epic fails,


Groove launched to the public.
Weve come a long way, but not
without some hurdles
In the weeks after Grooves public launch, we saw our user acquisition numbers
grow slowly but steadily. And while any growth is good, slow and steady isnt
always enough when you have mounting bills and a team that depends on you to
keep the paychecks coming.
Over the next several months, I learned more than I ever have in such a short
period. We tested dozens of strategies and hacks, and explored hundreds of
approaches to try and find the magic bullet to business growth.
The good news is that so far, weve done a decent job. To the tune of growing from
$0 in revenue to $30,000 per month.
The bad news is that there is no magic bullet. Growth takes work. A lot of it.
But weve been doing that work for nearly a year, and we have some key takeaways
that you can apply to your own quest for growth.

29

Background: Filling The Knowledge Gap


As I much as I learned in college, I didnt have a single class that covered
marketing automation, hiring, cash flow management, growth hacking, product
development, company culture, customer support or sales.
There are a lot of things that, before starting my last company, I simply never
learned how to do. As an entrepreneur, one of the scariest things in the world for
me is that uncertainty.
What if Im doing it wrong? I probably am. What am I not doing? Probably a lot.
What am I supposed to do in this situation? I have no idea.
Theres no way to make smart decisions with that sort of self-doubt.
Fortunately, it can be overcome. There are so many entrepreneurs who are
smarter, more experienced and more successful than I am. Much of their wisdom
is available for free on the internet.
So I dove in.
I spent an entire weekend tracking down the richest, most highly-regarded blogs
and publications on the web. I listed every single one I could find, and then I
devoured every post I could on those sites.

It took me three days to gather enough knowledge to take our business to the
next level.

30

For the list of blogs I came up with, check out this spreadsheet.
Copyblogger taught me how to put together the email autoresponder that now
gets delivered to every free trial user. Introducing that sequence boosted
conversions by more than 30%.
KISSmetrics helped us write headlines that converted 2-4x better than our
previous ones.
And HubSpot convinced me to stop looking at pageviews and start looking at the
metrics that actually mattered (more on that below).
This insight is all 100% free, and it has made a huge difference in the success of
Groove. I still make it a priority to devote at least an hour each day to keeping up
with some of the highest-value blogs on the internet.
Once youve done your research, youll have more ideas for growth strategies than
youll know what to do with
Takeaway: Theres so much free golden advice out there for startups and small
businesses, and youre robbing yourself if you dont take advantage of it. Too many
people look at reading blogs as a way to waste time, rather than the amazing
investment in their business that it truly is.

Getting New Users: Acquisition


Two strategies have accounted for more new users than everything else weve
tried, combined.
The first is something that every single business should be doing:

Inbound Marketing
Before we started blogging, traffic would come in bursts when we got news
coverage or social media buzz. Thats not a sustainable way to grow, and we knew
that we needed a better long-term strategy.
We began to think about what startups and small businesses would find useful,
and we started writing those pieces. One post was accepted as a guest post
submission on OnStartups, and another was syndicated by Business Insider.
We even studied successful small business-focused blogs and created a 44-point
checklist that listed the elements that we thought made those blogs work.
Our early blogging was hardly groundbreaking. But it didnt need to be. To go from
100 visitors per day to over 1000 (1000% growth) was more than we needed to
31

jumpstart our growth, and that traffic was mostly due to a few pieces of content
that our audience was able to learn from:

Of course, our inbound strategy has been (and still is) constantly evolving, and
were seeing returns now that dwarf what those first few posts brought in (and
yes, Ill be writing about that). But that initial step of starting to blog was the most
important one.
Takeaway: Start blogging, right now. Its the single highest-return strategy that
weve used for user acquisition.
The other strategy that helped us move the needle on user acquisition was

Powered By Groove
One afternoon, frustrated by the lack of progress we were seeing in our
acquisition efforts, I decided to start asking our newest users how they found out
about us. I didnt put together a survey or set up an eblast, I just sent a quick,
personal note to the last 20 people who had signed up.
That email turned out to be one of the best marketing decisions I ever made.
What I heard back was absolutely enlightening.
Of the 14 users that responded, eight of them replied that they saw an awesome
help widget on the website of a company that they loved, and they emailed those
companies to find out who was behind their helpdesks.

32

People were coming to us because they saw our product, and they had to ask our
customers who we were.
We were hiding from incredibly high-value prospects in plain sight.
If those eight customers loved what they saw enough to put in the effort and track
us down, how many potential users were out there who never bothered to follow
up?
As it turned out, a lot.
Two days later, we pushed a change to the Groove help widget. We added a small
hyperlink that said Powered By Groove that directed customers to our site.
The impact was immediate. Within three days, 100 visitors came to our site
through the widget, and 19 of them became customers.
Even today, while Powered By Groove only accounts for about 5% of our traffic,
visitors who come through this link are almost four times more likely to sign up
for a free trial.

33

Takeaway: Make sure that you know where your most valuable customers are
coming from, and double down on those channels.

Getting Our Users Engaged: Activation


More than any other challenge, activation was our primary post-launch focus.
If you cant get users actually using your product, then your acquisition efforts are
all for nothing.
When it came to overcoming the activation challenge, the first piece of the puzzle
was to

Optimize Our Onboarding Process


I discussed this at length in the Early Fails post, but Groove simply had too many
features. It was overwhelming for new users.
Because of that, we had a seven-step onboarding flow that took about seven
minutes to complete. It asked the user to engage with nearly all of our features,
and it turned out to be a huge abandonment point.
In February, 15% of users who began our onboarding flow would continue all the
way through it.

34

The product issue was hurting us in more places than just activation, and we were
forced to strip it down by removing several ancillary features, and putting other
features and integrations in an App Store that would only be accessed by a user
after they were engaged.
We also asked our most engaged customers what their wow moment with
Groove was. The one when they knew that this was the right tool for them.
The responses we got made it clear that for most users, the aha moment came
when they created a mailbox and looked at their new dashboard.
The metrics confirmed it: users who created a mailbox during their first session
were nearly six times more likely to return for a second visit.
We scaled the flow back and focused it on getting users to complete that single,
simple task.
The result? Over 4X the engagement.

Thats a huge boost in activation, and it all came about from looking at usage
metrics and talking to our users.

35

The second strategy that helped us beat the activation blues was

Automated Activation Emails


Since we knew that the big challenge was getting users to create a mailbox, we set
up the autoresponder for free trial users to focus on that single call to action. Any
user who didnt create a mailbox during their first session would get an automated
email to nudge them back to that simple little task.

36

We saw within two weeks that users who received the activation emails were 18%
more likely to stick around than users that didnt.
Takeaway: Find out where the friction in your onboarding process is, and get rid
of it. Know what your products activation triggers are, and do everything you can
to get your users to complete them.

Keeping Your Users: Retention


The activation emails didnt just serve to engage first-time users.
By continuing to send automated nudges to existing users after they became
active, we were able to introduce new features and functionality in a much more
digestible way, which ultimately led users to get far more value out of using
Groove.

These engagement emails helped us drop 30-day abandonment by almost 20%.


We also had another secret weapon in the battle against abandonment:

Awesome Customer Support


As we started to track everything more closely, we began to notice a trend: the
small subset of free trial users who emailed us for support were nine times more
37

likely to become paying customers by the end of their trial than those who never
reached out. Its a bit counterintuitive (which is why you must test every
assumption), but my suspicion is that this is due to those customers simply
putting more value on (and getting more value from) Groove from the very
beginning. If they werent getting great value from us, they likely wouldnt bother
asking for help when they hit a snag.
So, following the 80/20 rule, we doubled down on free trial support. We made the
contact links more prominent and began to send calls to action encouraging users
to reach out to us if they needed help. We were able to achieve a 20% lift in the
number of users who did actually reach out, and we started focusing on making
sure that those users had absolutely wow experiences.
Takeaway: Automate the process of helping your users get value out of your
product, because creating value for them is the only way to keep them around. For
startups and small businesses, being really good at support is not optional.

Next Up: Revenue - Turning Users Into


Customers
While user counts and engagement metrics are a great way to judge the health of
your product, theres only one true standard by which to judge the success of your
business: revenue. If you cant turn your users into paying customers, you wont
get the cash flow you need to survive and grow.
In next weeks post, well detail how we turned on the revenue jets, and finally
went from a $0 company to a $30,000 a month business.
Well cover:
Why listening to your customers about pricing could be a terrible idea.
How we got pricing wrong (twice) before getting it right, and how you can
avoid the same mistake.
The change we made to our pricing model to boost free-to-paid conversions
by 400%.
Well be releasing a new post each week. To get each post emailed to you as soon
as its published, sign up for the $100K mailing list below.
See you next week.

38

The Pricing Model That Increased Our


Free Trial Signups by 358% (and
Revenue by 25%)
October 24, 2013

A few months after launch, we were


acquiring, activating and retaining users.
Still, there was one piece missing
As most of the Groove team sat around my kitchen table, we were brainstorming
about how were were going to solve the ultimate business challenge:
How are we going to make money?
Of course, the first and most important answer to that question is to have
something that people are willing to pay for.
But after months of tweaking, stripping down, building up and optimizing, we had
that. People were getting real business value out of using Groove.
Still, all we had been asking for in return is user feedback.
That was a fair trade when we were trying to put together a product that actually
works, but now, in order to keep the business alive, we had to start getting paid.

39

Disclaimer: the pricing models discussed in this post, no matter how disruptive we
tried to be, arent revolutionary. Theyre the same basic models that youd find in
many SaaS businesses. But the lesson, for me at least, was the importance of testing
everything, no matter how basic or simple it seems. Read on to see what I mean
We began kicking around ideas:
What if we just use the same model as Zendesk or Desk.com, but cheaper?
How about we have a low base price and charge for extras?
We could do a flat rate per company, instead of billing per agent.
No.
These werent disruptive enough. We got into this game to change the way
people think about support, and that starts with pricing. We have to blow peoples
minds with a customer-friendly pricing model that was unlike anything out there.
So thats what we set out to create.

Freemium (and Conversion-Killing) Pricing


After a few days, we had what we thought was the winning formula:
Unmatched flexibility in a freemium offering that had per-agent pricing, but also
let companies have part-time agents.
Doesnt get much more flexible than that, right?

40

To us, the page looked like a breath of fresh air when compared to the
competition.
But to our customers and prospects?

Boy, did that fail.


As we talked to more and more site visitors, something we shouldve known all
along became very clear: our pricing model was ridiculous. It was overwhelming,
and made the decision to buy from Groove a complex one.
Our unmatched flexibility was costing us customers. We had to change
direction.
Takeaway: Never complicate what you can simplify. Especially if your competitors
are simplifying. Making your customers work to understand your pricing is never
the right approach.

Straightforward, Pay-As-You-Go (and


Terrifying) Pricing
Asking our customers had worked well for us in the past, so we decided to try it
again.
We asked 30 customers both from the most-engaged pool as well as the leastengaged one what sort of pricing might be the best fit for them.

41

Of the 30, 11 gave us nearly the same answer:

People wanted to pay for the number of support tickets they handled, not the
number of agents on their team.
Great! It only took a couple of days to put this new, improved pricing scheme
together:

42

Another research breakthrough!


Well, not really.
While Id love to say that this research-backed change went on to make us a ton of
money, this one flopped, too.

Even though people told us that this approach would make them happy, when we
dug deep and asked site visitors for honest feedback, we found that they ended up
being scared about the uncertainty of never knowing what theyd be paying in a
given month.
Takeaway: Your customers are your lifeblood. Love them, support them, and help
them succeed. But you dont always have to listen to them. For many issues (like
pricing), what they say they want and what theyll actually act on are entirely
different.

Super-Simple (and Finally Effective) Pricing


This was getting really frustrating. We were putting a ton of work into pricing, and
seeing nothing but negative results.
Our aha moment came one afternoon when we werent even working on pricing.
The team was huddled around the Groove web app, and we were busy simplifying.
As we stripped off feature after feature, moving ancillary functions into the
Groove App Store to streamline the user experience, it hit me:
If our uniqueness comes from being the simplest, easiest app, then our pricing has to
43

reflect that, too.


Well, it wasnt that eloquent in my head at the time, but the point was clear: we
needed to simplify pricing.
So just as we did with our product, we stripped down pricing to its most basic,
simple form.
One single price. Everything included. No extra charges. 14 days free.

We had a winner. Almost immediately, we began to see conversions rise more


than 350% over the previous model!

44

And even more importantly, this simple change (no pun intended) led to a 25%
increase in overall revenue. We had finally solved one of the most pressing
challenges in our business: we were making money, and we were doing it
effectively.
Takeaway: No pricing model is right for everyone. For us, a simple, flat price
finally worked. For you, that might be increasingly robust tiers of a business app,
or pay-as-you-go. Think about what your customers expect from your product,
and make your pricing reflect that.

Bonus: The Pricing Comparison Chart


Shortly after we introduced the winning pricing model, we added something that
boosted conversions even further: a tool that made the decision to use Groove
even easier.
We put together a chart that compared what a user would pay for Groove, versus
what they would pay using our competitors apps:

Notice how this isnt a feature matrix that only has a few features checked in our
competitors columns, and a column full of checks for Groove. These are bullshit,
and everyone knows it.
The chart above takes an objective look at a single differentiating factor: cost. And
45

it makes the decision for those for whom cost is a deciding factor very, very easy.
Takeaway: No pricing model is right for everyone. For us, a simple, flat price
finally worked. Note that "simple" doesnt have to mean "cheaper." Think about
what your customers expect from your product, and make your pricing reflect
that.

What's Next?
In next weeks post, well cover how we launched our new blog and get 88
comments, 1,000 subscribers and thousands of shares within 24 hours.
It will cover:
Why influencers like Gary Vaynerchuk, Andrew Warner and Dharmesh Shah
were excited to share our content.
The exact email scripts we used to build relationships with influencers and
get feedback that dramatically improved our content and shares.
A simple email hack that increased the number of recipients who shared our
blog post by nearly 50%
What havent we done?
A whole lot.
With our focus on product development while we made the long, slow trudge
toward product/market fit, we havent done much more for growth than what you
see above.
That all changes now.
Nearly all of our focus from this point forward will be on testing, tuning and
applying new strategies and techniques to go from where we are ($30K in monthly
revenue) to where weve set our sights ($100K) and beyond.

46

How We Grew Our Blog to 5,000+


Subscribers in Five Weeks
October 31, 2013

We were struggling to get traction on


our blog. Heres exactly what we did to
go from 200 to over 5,000 subscribers
Our blog sucks. Lets discuss at 10AM tomorrow.
Thats the email I sent to my guys at 2:11PM on August 24th, that sparked a month
long sprint to launch the series youre reading right now. In just five weeks, it's
brought us 82,629 unique visitors, 5,256 email subscribers, and most importantly
535 new trials.

47

Today, Im pulling back the curtain on the most important lessons we learned
along the way.
Disclaimer: Yes, it has only been five weeks. Yes, this effort could crash and burn
spectacularly at any time. No, Im not an expert at this. But the goal of this series is
to offer an unfiltered view of growth as it happens. And while I cant tell you what
will work for your business, I hope that you can learn a lot from whats
working and not working for ours.

Finding Our Identity


When our team met the next day, we spent an hour looking at our blog. No
discussion, no strategizing. Just reading every post in its entirety.
This simple exercise which we hadnt done in months of publishing made one
thing very clear: it had zero chance of being a serious marketing channel.

While we had around 1,000 pageviews a day and a few posts that had been shared
a handful of times, there was nothing that made our blog unique. We were simply
writing lowest common denominator posts about general customer support and
startup advice. Commodity content that wouldve looked equally at home on about
a thousand other blogs.

48

We had no focus, no hook, and worst of all no identity.


Look at some of the most successful content marketers out there:
HubSpot takes a unique approach to inbound marketing.
Copyblogger focuses on high-impact strategies to make your writing more
successful.
Helpscout is a direct competitor of ours, but Ill swallow my pride to say that
they do a terrific job blogging in the research-backed customer loyalty niche.

Trying to beat these guys at their own game would be a suckers bet. We cant be a
better version of Copyblogger. Theyre just too good and too entrenched.
We needed to carve out our own space. To find that unique Groove voice, and
amplify it.
Takeaway: You must tell your own story to stand out. Learn as much as you can
from successful blogs, but dont try to copy their angle. Take the strategies that
helped those blogs grow, and apply them to the voice and content that makes you
unique.
49

What Makes a Blog Great?


All successful blogs we studied had two things in common:
1. A ton of free value for their audience.
2. A great unique selling proposition.
Ive found that its helpful to think of your company's blog like any other product
you build.
If your product doesnt deliver massive value to your users, then no amount of
growth hacking will help you succeed. Our topic had to be useful to our audience.
It had to provide real, actionable advice; not just the soapbox philosophizing that
we like many other business bloggers had been guilty of in the past.
Beyond that, just like great products, the best blogs have a clear and unique value
proposition that makes it obvious why you should care about them.
For a great example of this, see Optimizelys fantastic CRO blog:

There are a lot of great blogs, but fortunately there are lots of unique angles that
have yet to be covered

50

What Would Make Our Blog Great?


What content could we, an early stage startup, possibly have to offer?
We didnt have Ten Tips for Building a Successful Business or A Guide To Making
Millions; because, we hadnt lived those stories yet.
But the more we discussed it, we realized that the reality we were living in that
long, slow startup haul was something that a lot of people struggle with.
And as deep as I dug, one thing I couldnt find was a completely transparent,
authentic look at that long, slow road to startup success. Most of what's out there
is written after the fact. And while hindsight is 20/20, real-time vision is raw,
unadulterated, and ultimately far more relatable for those of us in the trenches.
Thats a story that we could tell. The one about our own journey to success. About
going from where we were (a $30K/month startup) to where we had set our sights
for our next milestone: $100,000 in monthly revenue.

The content would be relatable and valuable. Nearly every startup and small
business struggles with growth. If we could relay our experiences and how we
overcame specific challenges, other businesses would be able to learn a lot. And
even when we failed, startups could still learn from that too. It was a topic
uniquely suited for our audience.
(That assumption turned out to be right, but also wrong. While many of our
readers are startup and small business owners, I get a lot of emails from funded
companies, investors, and even college professors about how much theyre
enjoying the journey.)
So our Journey to $100K a Month blog was born.

51

Takeaway: Dont underestimate what you can teach others. Things that seem
obvious to you are probably completely new and scary for others. Sharing your
experience and the lessons you've learned can be incredibly valuable.

What Did Great Blogs Have That We Didnt?


As we got to work putting together the first few posts for our new blog, we began
to apply a few of the other elements that the most successful blogs we studied
had in common:
1. High quality visuals: Aside from breaking up walls of text and making content
easier to digest, we noticed that well designed visuals added an air of authority to
blog posts. I committed one of my designers to making the blog images beautiful
and easy-to-understand.
The images for the first post took about 16 man-hours to get right. Next week, Ill
lay out exactly why I think that investment was worth it.
2. A reason to subscribe: With only a few hundred subscribers in six months, the
half-assed sidebar subscription form we had in the past wasnt cutting it:

Of course, neither was the blog, but the poor call-to-action certainly wasnt
helping.

52

If our blog was going to become a true business asset, we needed to capture every
possible lead that we could. Our subscription form had to be persuasive and give
readers a real reason to sign up.

While were still testing and optimizing, this form has converted around 5.3% of
new readers so far.
3. Influencers: Blogs like KISSMetrics are constantly being shared by people with
massive audiences. Clearly, influencers hold the keys to an incredibly valuable
kingdom. And like the most successful bloggers out there, we wanted access too.

Making It Happen (Plus, Are We Crazy?)


The strategy we ended up executing helped us get over 1,000 email subscribers
within 24 hours of publishing our first post.
Hint: It started well before that day.
The gears of engagement started spinning around four weeks before we launched
our blog. I wish I could say that I managed the process like a puppet master,
knowing that if I do x, y, and z, Id get the results I want.

53

But to be completely honest, while I had done a TON of research, I still had no
idea whether we would be successful or not.
And beyond that, I was scared.
When you stop and think about it, its crazy for a business to be this transparent.
What happens when we hit a bump in the road? What will our customers think?
Our investors?
Fortunately, I found a great way to validate our approach before we launched, and
to improve our content in the process. The best part is that its a technique that
anyone can use. And in my next post, Ill be laying it out for you step by step.

Engineering (and Not Just Hoping For) a


Successful Blog Launch
Next week, Ill share the strategies and techniques that got us those first 1,000
subscribers within 24 hours, including the exact email scripts that helped build
relationships with some of the most influential people in the startup world.
Well also cover:
How we validated our idea for the blog with a single email.
The influencer outreach spreadsheet that got our first post (and subsequent
ones) shared by guys like Dharmesh Shah and Andrew Chen.
A simple email hack that increased the number who shared our blog post by
nearly 50%.
Well be releasing a new post each week. To get each post emailed to you as soon
as its published, sign up for the $100K mailing list below.
See you next week.

54

How We Got 1,000+ Subscribers from


a Single Blog Post in 24 Hours
November 7, 2013

We had content, but no readers. Here


are the exact steps we took to build
relationships with influencers and find
an audience
We had just started working on the first post in our new blog series, and over
lunch, I was excitedly telling my friend a fairly well-known entrepreneur and
blogger about this latest development.
Awesome idea. Whats your plan for getting readers?
I was thinking Id launch it, and then email the link to as many important people as
I can.
My friend looked up from his iPhone and raised his eyebrows.
If expressions could talk, his was saying Dude. Are you kidding me right now?
Fortunately, he continued:
Do you know how many emails like that I get every single day? 99% of them come

55

from people who Ive never heard from before. Of those, 100% get ignored
immediately.
When I pressed him on why he did that, it became clear that his inbox was simply
too crowded with people he didnt know wanting his helpfor free.
Nobody cares about your email unless they care about you.
Over the next 20 minutes, my friend changed nearly everything I thought I knew
about reaching important people.
The most important lesson, by far, can be distilled down to this:
Forget your promotion strategy, and focus on engagement and building real,
mutually beneficial relationships, before you need them.
I know it sounds fluffy and buzzwordy, but lets take a look at exactly how weve
been able to apply this concept to our blog and get more than 5,000 subscribers
in just five weeks of publishing.

Step One: Building an Influencer List


Four weeks before we launched the blog, we began to put together a list of our
target influencers. Who do we want to build relationships with?

56

Our criteria was two-fold:


1. The influencer must speak to the same general audience SaaS startups and
small businesses that were trying to reach.
This seems obvious, but the more I spoke with influencers, the more I learned
about how many non-targeted email pitches they get. One customer service
blogger told me about a message he got asking to share the senders new post
about freelance bookkeeping tips.
Targeting people with whom you have nothing in common is, at best, a waste of
both of your times.
2. They should personally be able to get value out of our content.
Influencers have spent a lot of time and money building a reputation with their
audience. Why should they waste it sharing your crappy content?
This is just another reason to focus on making content as high-value as possible;
not just to help your readers personally, but to give them a reason to share.
We only wanted to reach out to influencers who could get value out of reading
our content (and applying our strategies to their own business), or out of sharing
it (by building social capital through sharing new, helpful ideas with their
audience).
Takeaway: Influencers hold the keys to the readership kingdom, but engagement
doesnt start with a pitch. Make a list of people who its possible to build
relationships with that would benefit both of you.

Step Two: Putting in the Effort to Engage


What do I want for Grooves content?
Ultimately, of course, I want it to grow Groove as a business.
But I also want people to get tremendous value out of it. To share it. To leave
insightful comments on it. And yes, even to give me internet high-fives.
Turns out, Im not the only one. Every content creator loves to know that their
content is making an impact. So I dove deep into our influencers content and
devoured it, learning an incredible amount in a short time.
But I didnt stop there.

57

I got to work promoting all of the great content Id read on our social channels,
and leaving insightful comments and starting discussions on their blogs.

You can find an easy-to-follow template of my engagement strategy here.


In a week, I began to build relationships with more than 80 influencers in ways
that made it obvious that I read and valued their material.

58

Takeaway: In the end, every content creator wants the same thing: validation that
their content is valuable. Find those whose content really is valuable, extract and
apply that value, and let them know that you did.
After I engaged with a writer a few times on their own blogs or via Twitter, it was
time for a small ask

Step Three: Validating The Idea


I emailed the influencers with whom Id already engaged with to let them know
about my crazy plans for the Journey to $100K a Month blog.
The ask might surprise you.

Note the key points:


First, we didnt just send them a link to the post. We asked for permission to share
an exclusive link to the post with them. This is a technique that we learned from
the brilliant Derek Halpern, and it was incredibly effective: more than 85% of the
people we sent the email to said yes!
Why?
59

Because were not shoving our content in their faces, as most people do.
Instead, were giving them a very brief synopsis of the content, and asking if
theyre interested in reading more. That way, when we do send them the content,
were no longer making such a huge ask; they were the ones who asked us to
share!
Second, we didnt ask them to post our content on their social networks. Why
should they? They had no idea who we were yet, and theres no good reason for
them to waste their audiences attention on us.
Instead, we asked them for feedback on the post. Its a much more benign ask, and
more importantly, helped us start real back-and-forth conversations with people.
The feedback we got from expert bloggers helped us make massive improvements
to our content, and still does.
And most importantly of all, much of the feedback that we got validated our idea
to write about our journey:

Takeaway: Before you ask anyone to help you grow your business, think about
how you can help them grow theirs. Only reach out to people who you can
legitimately help, and find a way to make your ask interesting for them.
Remember: nobody cares about you until you give them a reason.

60

Step Four: Preparing To Launch


Because of our early efforts at getting feedback and validation, a lot of influencers
were already aware of our upcoming post, and were excited to see it launch.
After all, they played a role in making it happen!
This gave us a massive advantage when it came to actually promoting the post.
About an hour before we published the post, we emailed our influencers and gave
them a heads up, and included a small ask.

This is where most content promoters start, but for us, most of the heavy lifting
had already been done. We were reaching out to people with whom we already
had relationships; we werent just pitching.
We sent emails to customers and inactive users with an announcement about the
blog post. In half of the emails, we tested the following:
Those who received that link were 52% more likely to Tweet the post!
If youre creating real value for your readers, theyll want to hear from you.
Takeaway: As my mother always told me, you dont get what you dont ask for, so
ask specifically for what you want. But make it easy for the people youre asking to
61

deliver, and more importantly, put in the work to build those relationships before
you ask.

Step Five: Responding To EVERY Comment


By the time we announced the post on Twitter, we already had more than 20
comments from some very big names:

I dont have data to back this up, but I truly believe that these comments were
instrumental in convincing new visitors to read the content. Even though they
62

didnt know who we were, they definitely knew guys like Gary, Dharmesh and
Andrew, and that was validation enough to convince newcomers from sources like
Hacker News that our content was worth reading.
In addition to the validation of having an active discussion, the comments gave us
a great opportunity to engage again with each reader who posted.
Additionally, we got some incredible feedback on what people wanted to read
about in the future. Now, we have 2,500-word posts in the queue inspired solely
by reader comments.

Takeaway: Dont underestimate the value of comments. Getting an influencer to


comment on your post can be just as valuable as having them share it. If you can,
respond to every comment you get: its an opportunity to engage that takes
almost no time at all (especially in the beginning).

Step Six: Sustainable Growth


Since our first post, weve published weekly content for seven weeks, and we have
no plans of stopping.
Nor do I have plans of stopping my engagement efforts; Ive said it before: I
genuinely learn a ton from reading other bloggers every week, and I continue to
comment, share and engage. Its a process that has allowed me to meet and
become friends with some extraordinary people.
Of course, you cant ask (or expect) people to help you every single week.
I didnt want to bite the hands that were feeding us, so I tried a little Permission
63

Marketing. Instead of bombarding my new friends with pitch emails every week, I
created an Inner Circle a list to whom I would send new posts for feedback
well before they were published.
I asked all of the people who had helped me with the blog whether they wanted to
join.

Surprisingly (to me), nearly 80% of those I asked said that theyd like to be
included.
The list continues to provide amazing feedback to make this blog better and more
helpful to our readers.

64

Takeaway: Feedback from brilliant people never gets less valuable. Find a way to
make sure that you keep getting that feedback from those who want to give it to
you.

The Results After 5 Weeks


Weve gotten more than 5,000 subscribers and 535 trial signups through our blog
efforts.
Weve also gotten a number of emails like this one:

From a revenue standpoint (since thats what this blog is all about), weve
generated about $3,425 in transactional revenue, though the real test of how
valuable these new users are over time remains to be seen. Well definitely keep
you posted.

65

Theres also the unmeasurable X-Factor in all of this: authority, thought


leadership, brand awareness, whatever marketing buzzword you want to assign to
it, its a difference we can feel. The same people we used to go to for guidance are
now asking us for advice. Im getting interview requests and speaking
engagements. All of this helps Groove grow.

Onward
We still have a number of approaches we want to test, and dozens of ideas in the
pipeline.
Were talking to potential syndication partners, exploring guest blogging
opportunities, and looking at other media (for example, video) for delivering our
content.
Well be sure to let you know how it works out.

Whats Next?
In next weeks post, well cover a growth issue that weve been struggling with for
quite some time: hiring. While some challenges still remain, weve been able to
overcome quite a few of them.
Well cover:
How I was able to recruit top talent at an early stage, without big investors.
The job posting A/B test that nearly doubled the number of qualified
applicants.
Strategies that have worked for us to build a company culture with a (mostly)
remote team.

66

How We Failed Our Way to a Day on


the Front Page of Hacker News
November 14, 2013

We had a foolproof strategy to get on the


front page of Hacker News. Heres what
happened when it failed
Holy shit. This is awesome.
We had been trying to figure out Hacker News. How to, at the risk of sounding
cliche, hack the thing.
And here, this post from Alex Taub biz dev guy from Dwolla and excellent
blogger offered the answer on a silver platter.
Like every content marketer, I got a rush from seeing our posts on the front page,
and the rush of traffic it gave us had the potential to make a huge impact on our
business.
And so, every time we published a post, I dutifully submitted it to HN and sent the
link to everyone I could think of, asking for upvotes. Somehow, nothing seemed to
work.
Alex's post made it clear to me, I was doing it all wrong.

67

The first two points that Alex made came as a complete surprise to me:

1. You only get one upvote per IP address. Asking everyone in the
office to upvote your post will result in 1 upvote (and I think if
you post from that IP, then possibly none).
2. Sending someone a direct link to your post results in an invalid
upvote. So if you plan on sending a link like this
(http://news.ycombinator.com/item?id=4371851) dont expect
anyone who upvotes from the link to be counted towards your
post.

Well, looking at our previous outreach efforts, it was obvious why things werent
working.

We were breaking the rules in every way possible.


Alex then goes on to stress the importance of writing great content, and then
shares his strategy:

1. Put the name and the direct URL, when submitting. Dont use
Bit.ly or any URL shortener.
2. As soon as you post you will be in
http://news.ycombinator.com/newest
3. Send the link (http://news.ycombinator.com/newest) to at least
20 people from different locations that you know will upvote or
submit it.

68

Ive heard that people submitting or upvoting with a solid


amount of karma helps (although Im not sure how much really).
4. Once you hit 5 or 6 upvotes, within the first five to ten minutes,
you should get to the first or second page.
5. Now you change the link (http://news.ycombinator.com/news)
and send the frontpage to people when asking to upvote going
forward. I would try to send to another 10 people. All at different
locations.
6. At this point you are 20-30 minutes in and if you have written
something interesting you will gain natural traction. If not,
there is really nothing anyone can do for you.

Boom. I love it when someone hands me a magic bullet.

Lets Do This
We had our next blog post Seven Lessons We Learned Going from $0 to
$30K/month ready to go.
We decided to publish the post on Thursday, October 17th. We also decided to go
one step further than the strategy that Alex outlined rather than just asking
others to upvote, wed also try and get someone outside of Groove to do the initial
submission. The reasoning was that our own submissions had been doing worse
and worse I suspect, but obviously cant prove, that this might be algorithmic on
the part of HN so that the front page isnt always occupied by the same users.
That morning, I tapped a friend (and influencer with 3K+ Hacker News karma) to
submit the post.

69

Once he was on board, I went to work lining up a team of upvoters from different
IP addresses.
Following Alexs strategy, we wanted to get as many upvotes as we could, as
quickly as possible.

At precisely 11AM, the post went live. Game time.


Jumping into action, I emailed everyone I had arranged to upvote our submission.
They dutifully navigated over to the New Submissions page and logged their
upvotes.
Everything went exactly as planned
until it didnt.

70

Well, that was fast.


Less than ten minutes after executing on our bulletproof strategy, our post was
nowhere to be found.
Not on the front page, not on page two, not on page three.
Oh, well. Another test Im glad I ran, and another valuable lesson learned.
Well have to blog about this, I thought as I opened up my inbox and got back to
work.
Takeaway: Theres no magic bullet. It sounds obvious in hindsight, but the best
practices that work for others might not work for you, but thats okay. Testing
and failing is valuable, too.

But Wait!
An hour later, I was sitting at my desk and responding to a customer email, when a
HipChat notification popped up in the corner of my screen.

71

It was a message from one of our developers, Jordan.

We were on the front page! And our post was absolutely crushing it at the #1 spot.

Except that it wasnt our submission. One of our readers, joshdance, had
submitted the post himself.
And interestingly, he changed the headline from 7 Lessons We Learned Going from
72

Zero to $30k/Month in Under a Year, to Lessons Learned Going from Zero to


$30k/Month in a Year.
Shorter, simpler, more direct. Flies in the face of the copywriting wisdom I had
been reading about specificity and numbered lists. And yet, it worked!
An unexpected lesson, to be sure, but one that I loved learning. Thanks Josh!
A couple of hours later, the post was still on the front page. And at 8AM the next
morning, we were sitting high at number ten.
That post stayed on the front page of Hacker News for more than 30 hours.

Takeaway: While Alexs step-by-step strategy didnt work for us, his first point was
spot on: create content that people will love and want to share with their friends.
We werent able to hack HN, but we didnt have to; by putting effort into
publishing high-value content, we were able to get our readers to do much of the
heavy lifting for us.

The Value of Hacker News Traffic


This is a blog about business growth, so lets talk about what our 30+ hour front
page marathon meant to Grooves numbers.
73

Using KISSMetrics, we tracked the behavior of visitors from the ycombinator.com


domain. In a two-day period starting when Josh first submitted our post, we got:

Not bad for free traffic.


I also loved getting emails like this one:

Heres the best part: of the 96 free trial signups, 12 converted to paid accounts
after their 14-day free trial. A 12.5% conversion rate. Certainly not a statistically
significant data set, but it does get me excited to do more testing.

74

Takeaway: Hacker News traffic may or may not be more valuable than the traffic
youre getting from other channels, but that doesnt really matter. If you do what
we plan on doing in the future not touching it and letting our readers post if
they feel our content is share-worthy then its absolutely free. And for our small,
not-yet-viable sample size, the conversion rate is strong.

Hacker News is Not a Promotion Strategy


Its important to note that our blog post was helped to succeed by Hacker News.
But it didnt succeed solely because of HN. And neither will yours.
Weve laid out our multi-faceted strategic approach to blog creation and
engagement. I hope youll read them, learn the same lessons we did, and apply
them to your own blog.
And then, if you do all of those things right, I can all-but-guarantee that the
Hacker News love will come.

75

Why I Turned Down


$5 Million in VC Funding
November 21, 2013

After weeks of gut-wrenching


indecision, I turned down a dream offer.
Today, Im sharing the five critical
questions that led me to make that call
I really appreciate the offer, but I Im going to pass.
The uncomfortable 5-second silence that followed gave me plenty of time to think
about what a colossal mistake I was making.
I cant believe Im saying no.
I had spent the last four weeks sweating over an unexpected offer from a fairly
well-known east coast venture capitalist.
The offer would make it easy to tackle our two-year product roadmap in a
sixmonth sprint.
In that four-week span of indecisiveness, I made more pro/con lists, pulled more
straws and called on more friends and mentors for advice than I had in my entire
life.

76

But ultimately, I said no. And as I write this a year later, Im extremely happy with
that decision.
The decision to pass was made easiest by a conversation with a founder friend of
mine who made the opposite choice: his SaaS startup took a big helping of VC
cash. And though he made out very well when his company was acquired a few
months ago, he shared his own approach to fundraising: five questions that, once
answered, gave me the clarity I needed to see the right choice for Groove.
Disclaimer: Im not trying to build a case against venture capital funding. It can be
valuable for many types of businesses. Im trying to offer a framework for thinking
about how to approach fundraising for your own business, and to help you reach the
right conclusions for yourself.
Im admittedly not an expert on this; but I hope that by opening up my own
thought process, we can all learn from each other.

1) How Badly Do You Need the Cash?

I had bootstrapped Groove with the cash I made when my last company was
acquired. After a brutally stagnant eight months of back-and-forth acquisition
talks led to nothing, I raised a $1M convertible note from a small group of local
angel investors. I knew these folks well, and I trusted them deeply. And the
convertible debt vs. standard equity financing, which is what VCs generally
offer was frankly much more attractive to us at our early stage.
When the VC offer came, we were pulling in roughly $16,000 in monthly revenue,
77

and had about eight months of cash left in the bank.


Importantly, with eight months of runway, Groove didnt need the money. There
were great arguments to be made about how we could use the money, but werent
running out of cash.
Takeaway: Are you taking funding for the sake of taking funding, or do you
actually need the money? If its the former, consider carefully whether you can
grow on your own, if only to put yourself in a better position for funding later.
Traction and growth = leverage = more favorable terms.

2) Whats Your Endgame?


As Aileen Lee writes, more than ever, top VC firms need billion-dollar exits to win.
For example to return just the initial capital of a $400 million
venture fund, that might mean needing to own 20 percent of two
different $1 billion companies, or 20 percent of a $2 billion company
when the company is acquired or goes public.
As blasphemous as it may be to the TechCrunch crowd, I have no interest in
turning Groove into a billion-dollar company.
To me, Groove is a business that I want to work on for a very long time. I love
customer support. I love helping other startups and small businesses succeed. I
would be perfectly happy to do this every day for the rest of my career.
Of course, I want to be successful. I want enough wealth to have the option of
quitting whenever I choose. I want to surf.

78

I want, as DHH so aptly puts it, maximum happiness for the maximum amount of
time. I want my team to have the same.
But Ive run the numbers, and that dream doesnt require a billion dollars.
It doesnt require a massive payout, and it doesnt require an IPO.
With that in mind, itd be tough to find a VC investor with whom our interests
truly aligned.
Takeaway: Youre running your business based on the goals you have for it. Your
investors need to share those goals, otherwise you may be headed towards a nasty
collision. If your goal is to have a billion-dollar exit, VC funding may be the best
choice for you.

3) What Will the Money Change?


Although I didnt think so at the time, but when these conversations were
happening, our product sucked.

79

If we had taken in a few million dollars, my focus wouldve been on scaling: getting
as many customers as possible to use our shitty app.
Groove wasnt mature enough as a product to offer real value, and I wasnt mature
enough as a founder to admit that.
Had we tried to scale, we wouldve almost certainly been left with a ton of angry
customers, even more ex-customers, and an app that couldnt keep up with any of
it.
Takeaway: If you want to take funding to help you scale, make sure that your
product is ready for it. Think its impossible to be over-funded? Think again.

4) How Much are You Willing to Get Diluted?


It was my own mistake, one founder friend of mine told me over coffee, but if I
realized how much I was giving away, I probably wouldnt have taken the money.
Now, Id have more upside if I just took a job.
That revelation floored me. That a born entrepreneur a hustler through and
through was so diluted (between three co-founders and one big VC investor)
that he predicted his chances of financial success would be higher if he went to
work for someone else.
Every time you give equity in your company to someone else, you raise the
threshold of profit you need to hit (or the size of your exit, if thats what youre
after) in order to hit your own personal goals.

80

A founder with different goals or maybe one thats just more brave than I
am might have rightfully decided to take the money.
I couldnt.
Takeaway: Take the time to do the math right. Its possible that dilution will force
you to change your goals so that you can still achieve a favorable outcome. Will
your business still be viable if it has to do twice as well as you originally hoped?

5) Is There Another Way to Get to Your


Goals?
This is the question that sealed the decision for me.
I thought long and hard about what our near-term goals actually were.
In the end, it was pretty simple:

Our goals didnt require a huge cash infusion. Our goals could be reached, by my
calculation, through growing our revenue alone.
How much revenue would we need, exactly, to get to where we needed to be?
Around $100,000 a month.

81

Thats why I turned down the money.


And thats a big part of why youre reading this blog series today.
Takeaway: Now, more than ever, its possible to reach your goals without a huge
pile of cash. There are almost unlimited resources out there to help you grow your
business on your own. If you dont take advantage of those, and instead assume
that you need funding to grow, youre doing yourself a disservice.

Theres No Best Answer.


Theres only the best answer for your company at an exact moment in time.
There are hugely successful companies that simply wouldnt exist today if it
werent for institutional investors. There are plenty of great bootstrapped success
stories, too.
For Groove, earlier this year, the answer was that VC funding was I hope the
wrong choice. Things may be different in just a few months or years.
Of course, many startups would kill to just be in the position to choose whether to
accept funding or not. That was Groove not too long ago. I hope that reading this
leaves you more prepared for that difficult decision when the time comes.

82

100,000+ Reasons To Be Thankful


November 27, 2013

Its Thanksgiving in the U.S. tomorrow.


No strategies, hacks, or lessons in this
post. Just one very important message
We started writing this blog ten weeks ago as an experiment.
Would people care about our little SaaS startups journey to success?
Thankfully, it turned out that many of you care. And Im grateful that since we
published our first post, more than 100,000 unique visitors have come to our blog
and shared in the lessons weve been learning along the way.
Im also grateful that youve helped us move closer to our $100,000 goal as of
this month, weve increased our monthly revenue by more than 10% since we
started the blog.
And more than all of that, Im grateful for the community weve all built here. So
many of you come back each week and spark lively, fascinating discussions in the
comments, and we all learn so much from them. In many ways, those discussions
are more helpful to me as a founder than writing the blog itself.
Ill be the first to admit that Im not immune to the founder ego that plagues so
many small businesses. Ive written before about how much it hurt Groove early
on, and Ive been working really hard to improve. I find that expressing gratitude is
83

one of the best ways to remind myself that Im not even remotely the only one
responsible for Grooves success. I recommend that every founder - and every
person, really - give gratitude a determined try.
And while gratitude is a year-round pursuit, Thanksgiving is a fantastic reminder
to those of us that need it.
So thank you.
Thank you for reading, for sharing, for commenting, for teaching me and the team
a lot over these last ten weeks.
Im grateful.

84

Why I Dont Stress Over Competition


Anymore
December 5, 2013

Every entrepreneur that I know has lost


sleep worrying about their competition.
Heres why Ive decided to stop
worrying
Damn.
As I frowned at the mirror and traced the lines with my finger, I couldnt help but
think that 32 is way too young to be getting wrinkles around my eyes.

85

I was stressed, and it showed. I wasnt sleeping well, I wasnt eating right, and I
was bummed out.
Simply running a business is more than enough of an excuse to make almost every
other stressed-out entrepreneur nod their head sympathetically, but I wasnt
ready to accept it.
So a few months ago, I set out to find and eliminate (or at least reduce) the specific
sources of stress in my business life.
What I realized was that by far, the most disproportionate and
controllable cause for anxiety was the hours I spent thinking about what our
competitors were up to.
Are they stealing my customers?
Are they better at running a business?
Are they building some new industry-defining feature that I havent thought of?
And while I knew I had to stop focusing so much on the competition, the fixation
couldnt simply be turned off. I had to work really hard at it.
And while Im doing a much better job these days at managing stress and focusing
on the right things, sweating the competition is still something I have to
deliberately stop myself from doing.
To that end, what follows is as much a reminder for me as I hope it is for you.
Im happy to say that after a whole lot of conversations with advisors and other
entrepreneurs far smarter than I am, as well as honest reflection on the state of
Groove and our goals, Im no longer losing sleep over competition, and heres why:

1) Competition Validates Your Business


Ive told this story on the blog before, but early on in Grooves development, a
fairly well-known VC asked me:
Why on earth would you want to enter this space? Youll be fighting
an uphill battle against huge players. Zendesk, Desk.com, plus an
overcrowded market of smaller companies.
And he was absolutely right our customers had dozens of options.
But that was exactly why I wanted to get into this market.

86

Fifty other companies trying to solve the exact same problem?


Fantastic. Ill take that over trying to convince people of a problem they didnt
even know they had.
The frenzy of customer support software companies shows that its a problem
that people want solved.
Plus, we dont have to be better than Zendesk.
We just have to be better than Zendesk for our specific audience.
Groove isnt right for everyone, and neither is Zendesk. Or Uservoice. Or
Desk.com.
But by building the best damn support software possible for our small-ish niche of
potential users, Groove can become the no-brainer best option for enough
customers to still achieve our goals as a business.
One of our readers, Mark Hansen, was kind enough to do the math on his blog:
There are 125 million SMBs (small or medium businesses) in the
world.
Lets say 5% could benefit from SaaS customer service. Thats
probably conservative.
So, rounding down, we have:
6 million potential customers.
Apply the 80/20 rule and say that 80% of these potential customers
follow the herd and pick one of the top 3 providers like Zendesk.
So, 20% of the market is left for Groove and the smaller guys.
That leaves: 1.2 million potential Groove customers.
How many of these customers does Groove need in order to get to
$100,000 per month?
The product costs $15 per month per user. Being conservative, lets
suppose that all their customers have only one user [Note from Alex:
this number is actually higher, see my explanation below].

87

So, they need 100,000/15 = (rounding up) 7,000 customers required


to hit the goal.
Thats just a tiny fraction of the potential customers,
7,000 / 1,200,000 = 0.58%
Inversely, the market can potentially support 1,200,000 / 7,000 = 171
companies like Groove could potentially reach $100,000 per month
in sales.
Marks approach is spot on, but our average customer has closer to three users.
So, the number of customers we need to hit $100,000 is more like
2,222 fortunately about 3x lower than Marks estimate.

Takeaway: A competitive marketplace means that theres a need for a solution, and
theres no way the biggest players are solving the problem for everyone. Theres
always a (potentially profitable) niche to carve out, with the caveat that you cant
simply build another solution; you must build a better one for a targeted audience.

2) Stressing Over Competition Might Not


Help
For some people, stressing over competition is the path to victory.
If youre looking to make a billion-dollar exit, you need to destroy your
competition. The potential benefit is huge when you look at exit multiples, as

88

Jason Lemkin beautifully illustrates.


But Groove isnt looking to make a billion-dollar exit.
I explained this in the post about turning down VC funding: Im in this game, as
DHH says, for maximum happiness for the maximum amount of time.
That approach lets our whole team strike a balance between working hard and
living the way we want to.

And it lets us happily push forward without trying to figure out how to destroy our
competitors.
With that said, our audience is certainly looking at the competition when they
evaluate their options, so we need to make sure Groove is better for our
customers specific needs. But theres a fine line between building a competitive
product and being obsessed about competition.
Takeaway: Figure out what your end goals are. If you want a huge exit, then focus
(some of your energy) on your competition. But if your goal is smaller and more
sustainable, then theres a lot less to be gained.

3) In Fact, Stressing Over Competition Could


Kill Your Business
I love watching other startups succeed, and Ive been cheering on Fab.com since

89

they hit the scene.

Its hard to watch their recent struggles, but theres a valuable lesson to be
learned: focusing on your competitors can come at a huge cost to your own
business.
Jason was hell-bent on destroying Fabs European competitor, and he sunk so
many millions into doing so that it wasnt long before the company hit a financial
wall. The layoffs and executive abandonment have left a painful hole in Fab. I hope
Jason can turn things around, and Im rooting for him.
Of course, there were many other factors involved, and the above is a huge
oversimplification, but it still gets at an important point: distraction is a businesskiller.
We learned the same lesson the hard way when six months of waffling on early
acquisition offers stalled our development nearly killed Groove you can read all
about it in my post about our early fails.
Takeaway: Dont get caught focusing on your competitors at the cost of making
wise decisions about your own business. At best, its a waste of energy and
resources, and at worst, its a startup death wish.

4) Even Worse, It Could Kill You


Im not a doctor nor a health expert, but I believe the British Medical Journal when
they say that even low-level stress can increase the risk of heart attack or stroke
by 20%.

90

What do health risks have to do with a startup blog?


As I mentioned above, Im in this game for the long haul. That long haul is going to
be a lot shorter if I worry myself to death.
The startup community loves to glorify the high-stress 24/7 slog of a lifestyle that
entrepreneurship brings, but Im doing my best to not fall into the same trap.
So while I still worry plenty about things that can make a big impact on our
business conversion rates, user experience, customer support the less sleep I
can lose, the better.
Easier said than done, I know, but reminding myself of this little fact helps.
Takeaway: Most entrepreneurs already carry enough stress to do real damage to
their health. Adding to that by worrying about something you cant even change?
Not worth it.

And at the End of the Day, Your Competitors


are Just as Worried as You Are
I try to bare it all on this blog: wins, fails, goals, excitement, disappointment, fear
One of the most enlightening lessons for me has been reading the comments and
seeing how many entrepreneurs echo the ups and downs of my emotions.
91

Were all riding the same roller coaster, and your competitors have the same fears
and concerns that you do.
Given the damage that competition-induced stress can do to a business, Im more
than happy to let our competitors do the worrying, and trade in my own stress for
a competitive edge.

92

Announcing the 2013 SaaS Small


Business Conversion Survey
December 12, 2013

Were giving away thousands of dollars in


awesome SaaS prizes from KISSMetrics,
Unbounce, Mixergy, Clarity.fm and more.
Heres why
A few weeks ago, I got an email from a reader that included this line:
More than anything, thanks for sharing your analytics. There isnt
enough transparency out there, and seeing how other startups are
doing is really helpful to first-time founders like me :)
Since starting this blog, Ive gotten hundreds of emails and comments expressing
that same sentiment.
And while I understand why many want to be super-protective of their metrics, I
wish we could all be more open about how our businesses are doing.
It would help all of us first-time founders and seasoned vets alike better
understand our space and benchmark our own efforts.
The reason that I started this blog is that my first time around as an entrepreneur,
93

I was simply lost when it came to how we stacked up:


Are we doing well?
Is our conversion rate good?
Whats our bounce rate SUPPOSED to be?
And while every business is different and thus all of our success metrics will be
different its incredibly helpful to know what baseline numbers we should be
aiming for, and what strategies are working for others to improve those numbers.
And while I wont ask you all to shout your metrics from the rooftops, I hope that
by sharing them anonymously and studying the results, we can all perform better.
Thats why Im excited to announce the launch of the 2013 SaaS Small Business
Conversion Survey. Take the survey now, or read on for more details.

Why You Should Take This Survey Right Now


We want to bring the community Grooves 7,000 subscribers, as well as the rest
of the SaaS startup/small business ecosystem together to create a free, valuable
resource for each other.
Were asking SaaS startups and small businesses to (anonymously) share data on
conversion rates, user acquisition strategies and other facets of their businesses,
to make us all more educated, more savvy and more successful.
Well compile and publish the results to answer some important questions about
our industry:
What user acquisition strategies are SaaS startups and small businesses
getting the most value from?
What are average website conversion rates for SaaS companies?
What are the average churn rates for SaaS businesses?
The survey itself takes about five minutes to complete. It just went live.
Take the 2013 SaaS Small Business Conversion Survey now.

Prizes
While the betterment of the SaaS community is the ultimate goal, we want to give
you even more incentive to participate.

94

Thats why weve partnered up with some incredible SaaS companies to offer these
awesome prizes:

A 90-day subscription to KISSmetrics


Value: $450
A six-month subscription to Unbounce
Value: $594
A three-month subscription to to Mixergy (x3)
Value: $199 each
A one-year subscription to Buffer (x3)
Value: $120 each
95

A SIGNED copy of Jab, Jab, Jab, Right Hook (x10)


Value: $30+ each
A $50 credit to Clarity.fm (x10)
Value: $50 each
A three-month subscription to Groove (x10)
Value: $135 each
A three-month subscription to CrazyEgg
Value: $297
A three-month subscription to Moz
Value: $297

Plus, for one very lucky winner

GRAND PRIZE: Two Tickets To The 2014 Business Of Software Conference


Value: $3,000
Thats more than $7,000 in prizes, yours for the taking.
Winners will be selected at random from survey participants.

96

Deadline
The survey will run until midnight EST on December 31, 2013.
We all get busy with the holiday season, so dont put this off until your vacation!
Fill out the survey now.

Tell Your Friends


The more people participate in this survey, the better our data is, the more
valuable the results of the survey will be for everyone. So, please tell your SaaS
friends about the survey.
To make things even easier, heres a Tweet you can send right now:
Take the 2013 SaaS Small Business Conversion Survey
Looking for a link to the survey? Its right here.

97

Our Metrics REVEALED: Revenue,


Churn, Conversions and More
December 19, 2013

Last week, we invited you to take the


2013 SaaS SMB Conversion Survey.
Today, were putting our own cards on
the table
If were trying to promote transparency, why dont we pull back the
curtain on our own responses to the survey?
Ill admit that the challenge one of our developers issued threw me off at first. I
think most founders have an instinctive gut reaction to keep their private data
private.
But my goal is to overcome that reaction in my own mind, and convince other
founders that by sharing more than we hide, we can all become better at business.
One of the ways Ive been doing that is by forcing myself to be very open with
Grooves numbers on this blog.
Hell, you can find our monthly revenue by scrolling down to the bottom of every
post.

98

But I know that the data were trying to collect in our survey can be even more
sensitive than that.
Revealing metrics like churn and average revenue per user the sorts of details
that competitors would love to get their hands on isnt that easy for me.
But, in the interest of drinking my own Kool-Aid, Im doing it anyway. And I hope
that doing so will help convince you to do the same (albeit anonymously, of
course).
In case you missed it, were asking SaaS startups and small businesses to
anonymously share data on conversion rates, user acquisition strategies and other
facets of their businesses, to make us all more educated, more savvy and more
successful.
Plus, weve partnered with KISSmetrics, Unbounce, Mixergy, Clarity.fm, Buffer and
the Business of Software Conference to offer more than $7,000 in prizes. All you
have to do for a chance to win is fill out the survey.
The deadline for completing the survey is midnight on December 31st.
Lets get into the details, shall we?
Has your business reached Product/Market Fit?
Yep. I covered how we determined that in this post.
What kind of SaaS business are you?
B2B.
How long have you been in business?
1-2 years. 26 months, to be exact.
How many full-time employees does your business have (including
founders)?
7.
What is your Monthly Recurring Revenue (MRR)?
$35,167. This one is no secret. After all, its what this blog is about.
What is your Average Revenue Per User (ARPU)?
$40.51. Our average customer has just under three support agents.
Which of these user acquisition strategies did you benefit MOST from this
year?
Content marketing, email marketing and customer/user referrals. The first

99

one shouldnt surprise anyone I wrote about how weve managed to


succeed in content here and here.
Do you offer a free trial (or free version) of your SaaS product?
Yep, 14 days free.
Do you require a credit card for free trial signups?
No. Weve tested it, and for us, requiring a credit card wasnt particularly
helpful.
What is your website visitor-to-free trial conversion rate?
2.3%. Pretty terrible at the moment, actually. Well be releasing a post soon
about this one, but it has a lot to do with the value of your traffic sources
for example, Hacker News traffic converts at a far lower rate than organic
blog traffic.
What is your free trial to paid customer conversion rate?
8%
What is your churn rate?
1.6%. I published a post on the KISSmetrics blog this week about how we
reduced this from 4.5%.

Now It's Your Turn


While our numbers alone wont be that helpful to you, collecting thousands of
data points will be valuable. Well use that data to answer questions like:
What user acquisition strategies are SaaS startups and small businesses
getting the most value from?
What are average website conversion rates for SaaS companies?
What are the average churn rates for SaaS businesses?
We want to bring the community together to build benchmarks and lessons for all
of us, and Id appreciate it if you took five minutes to be a part of our survey.
As a reminder, by filling out the survey, youre entering to win:

100

A 90-day subscription to KISSmetrics


Value: $450
A six-month subscription to Unbounce
Value: $594
A three-month subscription to to Mixergy (x3)
Value: $199 each
A one-year subscription to Buffer (x3)
Value: $120 each
A SIGNED copy of Jab, Jab, Jab, Right Hook (x10)
101

Value: $30+ each


A $50 credit to Clarity.fm (x10)
Value: $50 each
A three-month subscription to Groove (x10)
Value: $135 each
A three-month subscription to CrazyEgg
Value: $297
A three-month subscription to Moz
Value: $297

Plus, for one very lucky winner

GRAND PRIZE: Two Tickets To The 2014 Business Of Software Conference


Value: $3,000
Thats more than $7,000 in prizes, yours for the taking.
Winners will be selected at random from survey participants.

102

Deadline
The survey will run until midnight EST on December 31, 2013. We all get busy with
the holiday season, so dont put this off until your vacation! Fill out the survey
now.

103

Results Of The 2013 SaaS Small


Business Conversion Survey!
January 9, 2014

We asked businesses to share metrics


like conversion rates, churn rates and
revenue. Today, were publishing the
results.
In the early days of Groove, our team thought that wed made a huge
breakthrough when we decided to track everything.
Almost overnight, we had more insight into our business and our
customers than we knew what to do with. It was eye-opening to see just how
weak our assumptions about things like app performance and user behavior were
when they came face to face with the real numbers.
But we were wrong in thinking that tracking was the breakthrough.
The real turning point came when we acted on the data. When we began working
to move the needles, and to figure out which needles would have the biggest
impact on our business.
When we set the right goals, and focused on achieving them, Groove began to
take off.

104

But by far, the biggest challenge for me was trying to make sense of what our
numbers should look like. I didnt have anything to benchmark against, and that led
to a lot of guess-and-check that couldve been made easier by simply having some
data to start from.
Today, were taking a small step towards solving that problem for other SaaS
startups and small businesses

The 2013 SaaS Small Business


Conversion Survey
Last month, we called on the SaaS community to (anonymously) pull back the
curtain on their metrics for the greater good. We were blown away to get more
than 1,500 responses.
If you participated, thank you. It really means a lot to me, and hopefully to
everyone who benefits from this information.
Our promise was that in exchange for your submissions, wed compile a free
resource for SaaS startups and small businesses that would help benchmark
performance and set better goals, so that we can all become more savvy
entrepreneurs.
(Our other promise, of course, was 41 prizes, together worth more than $7,000.
More on that below.)
In this post, were publishing the top-level results of that survey.
Theres certainly more that we can do to dig even deeper into the data, and were
working on that. But we didnt want to wait another minute than we had to to
share these numbers with you

The Results
For this initial report, we removed outliers, normalized all currency to USD and
cut the data to only include the 712 respondents who have reached
Product/Market Fit, have been in business for at least 6 months and have at least
$1,000 (but less than $500K) in monthly recurring revenue.

105

106

107

The Winners Of More Than $7,000 In Prizes


This morning, we used Random.org to generate 41 winning respondents. Were
emailing all of the winners today, and they have until 5PM EST on Monday to claim
their prizes.
Winners: leave a comment below letting everyone know what youve won!

Thanks To All Who Participated


Once again, thanks to everyone who took the time to respond to our survey. We
were excited and energized by the awesome response of the community, and well
almost certainly be doing this again.
And yes, a post on the execution and promotion of the survey is coming soon.

108

How A Single Email Made Customers


350% More Likely To Convert
January 16, 2014

After finding a surprise in our data,


we set out to see if we could get more
incoming customer support
emails on purpose.
Early last year, Groove got serious about being a data-driven business. We began
to track everything, and between our marketing efforts, sales interactions and
user analytics, our massive cache of data was growing fast.
In May, I issued a challenge to our team: dig deep into our metrics, and try to find
non-obvious points where we can tweak, tune and optimize to make an impact on
our growth.
We found lots of little correlations; some that led to dead ends, and others that we
still pay attention to today.
But what one of our developers found was more than a little bit shocking (to me,
anyway).
In looking at our customer support data, he saw that free trial users who emailed
us for support were nearly nine times more likely to convert to paying customers

109

at the end of their trials than those who never reached out.
With the growing popularity of Knowledge Base software (even among our own
customers), most businesses were trying to go in the opposite direction: get fewer
support emails by helping customers help themselves, the assumption being that
customers would rather have faster answers than wait to deal with a support
agent.
Looking at our data, we wondered if everyone even our own customers had
been doing it wrong.
Of course, we couldnt take that data as gospel; it was far from statistically
significant, and it didnt account for variables on the reasons for the support
emails.
But it was enough to get us to do a little bit of testing.
And Im glad we did

Increasing Our Support Emails


We had never tried to increase support tickets before, so we tested three different
strategies to see what would work best:

Prominent In-App Calls-to-Action


We use Grooves help widget (shocker, I know) on our app, and it puts a support
tab in the bottom right corner of the users screen.

110

Previously, we had only been using the widget on the dashboard and a few select
internal pages of the app, as there were pages where we simply assumed that
users would never need support.
We tried putting the widget on every single screen within the Groove app.
Just for the hell of it, we also tested completely removing the widget from every
screen.
The results?
When we removed the widget, support emails dropped like a brick to the tune
of nearly 50% fewer emails received. The widget was definitely helping, especially
on the dashboard and ticket view pages.
But putting the widget on ancillary pages (for example, the Keyboard Shortcuts tab)
had only a marginal impact: an uptick of about 1% more users emailing us. Hardly
enough to make a dent.
Takeaway: A support widget can be incredibly effective at getting users to reach
out for support, but for us, the gains were mostly on the primary pages of our app.
Adding the widget to ancillary pages brought diminishing returns.

Time-Triggered Emails
We knew that our users generally responded very well to emails. For example, our
onboarding autoresponder emails with calls-to-action that prompt the reader
to go to the Groove app and complete specific tasks get upwards of 30%+
clickthrough on first open.
So, we began to add customer support emails to our onboarding sequence.
At the three-, six- or eleven-day marks, some free trial users would receive
support-specific emails prompting them to engage with us for help:

111

This email got almost a 22% response rate, and the users we ended up speaking
with were 40% more likely to convert. Nowhere near the 900% from our starter
data, but a significant improvement nonetheless.
Takeaway: As my mother told me growing up, you wont get what you want unless
you ask for it. Rather than trying to engineer user behavior through your app, if
you want your users to do something, no matter how simple, just try asking.

Behavior-Driven Emails
As I wrote in my recent guest post on KISSmetrics, we know how long certain
tasks within Groove are supposed to take:
Creating a rule generally takes between 10 and 30 seconds.
Integrating a Twitter account takes around 20 seconds.
Customizing a support widget is 2 to 3 minutes.
We figured that some of the users who were spending far more time than average
on these tasks might simply be stuck.
So we built a simple system that would alert us when a user would spend too
much time on a particular task in multiple sessions.
Then, we reached out to the user:

This email got a 10% response rate, and 30% of the users were still customers
after 30 days; more than 350% higher than our average free trial users (we
normally convert at about 8%).
112

Takeaway: You can probably identify "red flag metrics" that tell you when a
customer may be having trouble with your app. Use those as an opportunity to
reach out to those users and ensure that they have a good experience. Otherwise,
the data suggests that they probably wont email you; theyll just leave.

How To Apply This To Your Business


Between the various strategies we tested, we were able to increase the number of
trial users who emailed us by about 20% and of that 20%, nearly 25% convert
into paying customers.
Now, theres still a lot we dont know:
Exactly why these engagements increase conversions
How these engagements increase long term retention
Whether these results are specific to Groove, or if this strategy will work for
anyone
Sure, I have my suspicions, but my suspicions are often wrong. Regarding the first
two bullet points, were doing a lot of testing and customer development to get to
the answers.
Regarding the third point, I suggest you give increasing your support emails a try.
Or at the very least, look hard at your data to see if you can spot a correlation that
warrants further testing.
But more than that, the lesson for me and, I hope, for you is that our deeplyheld assumptions (for example, fewer support emails is better) could be keeping
us from achieving the results that we want.
These assumptions arent limited to support. Entrepreneurs who learn from
studying others make assumptions about every aspect of business, from marketing
to hiring to development to sales.
Often, testing those assumptions is cheap and easy, and at least in this case, it
certainly paid off.

113

How we got more than 1,500 survey


responses with a last-minute
scramble
January 23, 2014

Three days before releasing our survey,


we realized that we were totally
unprepared. Heres how we rallied
our way back
Id love to say that we had a rock-solid strategy in place well before we launched
our survey.
Id love to say that we systematically reverse-engineered our path to success.
Id love to, but I cant.
The fact is, we were treating the 2013 SaaS Small Business Conversion Survey like
any other blog post on our editorial calendar.
Sure, wed share it with our subscribers and ask folks to pass it on, but beyond
that, we hadnt really thought about promotion.
until three days before we were scheduled to launch it.

114

I was getting ready to power down for the day, and decided to give the survey
another quick read-through before calling it quits.
Well, shit, I realized as I reached the end.
We were asking for a hell of a lot.
Our usual ask of our readers is to leave a comment and share the post. A few
seconds of effort, and plenty of incentive if they think our content will be valuable
to their friends.
But this?
We were asking people not only to take five minutes about 1,000% more time
than usual to fill out a survey, but we were asking for data that, for many, would
require digging through internal numbers to come up with.
On top of that, we wanted data that most people would cringe at the thought of
sharing.
Not a small request, to be sure.
The following morning, our team huddled and brainstormed how we could extend
the reach of the survey, and get as many people as possible to take the time and
fill it out.
The ensuing scramble may very well have saved our survey

Putting together prizes that people


actually wanted
One tactic that we shamelessly stole from dozens of other companies who had
successfully asked readers to participate in events, surveys and contests was to
give away prizes.
My first thought was to put a $100 Amazon gift card as a grand prize.
Thinking about it now, that probably would have gotten us a total of four
responses (and mine would be 1/4 of them).
The prizes had to be big, and they had to be desirable.

115

We thought about what we would want if we were in the running, and came up
with a dream list of prizes.
The total value of our prize list?
Over $7,000.
Yikes.
We certainly didnt have that kind of budget for this. So we got to work.

Surprisingly (to me), every single company we emailed said yes.


In the end, we were able to offer:
A 90-day subscription to KISSmetrics (Value: $450)

116

A six-month subscription to Unbounce (Value: $594)


A three-month subscription to to Mixergy (x3) (Value: $199 each)
A one-year subscription to Buffer (x3) (Value: $120 each)
A $50 credit to Clarity.fm (x10) (Value: $50 each)
A three-month subscription to CrazyEgg (Value: $297)
A three-month subscription to Moz (Value: $297)
We threw in ten three-month subscriptions to Groove, ten signed copies of Gary
Vaynerchuks book (I bought 500 of these when he was doing a big promotional
push), and two tickets to the Business of Software Conference, and we finally had
a prize list to be proud of.
What impact did the prizes have on the outcome? Unfortunately, its not
something we could track, but my gut tells me it was significant.
And anecdotally, I got dozens of emails from people requesting to win specific
prizes.
(For the record, we picked the winners using random.org.)
Takeaway: People love prizes, but they have to be big enough to warrant what
youre asking. With the right strategy, offering thousands of dollars (or more) in
prizes doesnt have to cost you anything.

Getting partners on board


One big side benefit to our prize collection efforts was the team of rock-star
partners it led us to.
Every company who put up prizes got their logo on our blog, aligning our brands.
They now had skin in the game.
And best of all, the reach of our group of partners, put together, is massively wider
than the reach of our own blog.
When all was said and done, traffic from Tweets like these accounted for more
than 20% of the survey click-throughs from our blog:

117

Takeaway: Think outside of your own audience, and come up with ways you can
incentivize other influencers to get involved. The value is not only in the traffic
numbers they can deliver; the validation they offer can clear a lot of hurdles in
getting people to do what youre asking.

Promotion and Repetition


With a big ask like ours, we didnt think that a single post on our blog would bring
in a ton of responses.
118

And sure enough, our first post (not counting the partner Twitter traffic from
above) netted only a couple hundred responses.
We needed to stay in front of people, and doing that took two tactics:
First, we cleared the rest of our editorial calendar for the next couple of weeks
and dedicated the rest of December to campaign for survey responses on the blog.
We published a follow-up post Our Metrics REVEALED: Revenue, Churn,
Conversions and More that pulled the curtain back on our own responses to the
survey, followed by a call-to-action prompting readers to go to the survey.
The key here was that it wasnt another post parroting the same message; frankly,
that would be annoying.
We made sure that this post met the same criteria as our regular posts:
interesting, valuable and fun to read.
The repetition paid off, and this second post brought in nearly 40% more
responses than the first one did.
Second, we pulled an appropriately metrics-focused post out of our own blog
queue, added info about the survey at the end, and pitched it to KISSmetrics as a
guest blog post.

119

The piece How One SaaS Startup Reduced Churn 71% Using Red Flag
Metrics was relevant to their audience, and they agreed to publish it.
The post performed very well on their blog (in fact, we still get traffic from it). This
extended our reach far beyond our own audience, and kept the survey in peoples
minds.
Takeaway: As long as its valuable, interesting and relevant, content marketing is
incredibly valuable for promoting, well, just about anything.

What made this all possible


Truthfully, I suspect none of this would have worked out the same way if we didnt
have three things:
A strong, engaged audience of readers who trusted us enough to fill out the
survey, and gave our partners an incentive to get involved
Relationships with influencers that made it easy to pitch them on our idea
Pre-existing content that we could quickly and easily tweak for guest posting
The thing is, we didnt have any of those things just six months ago.
We got them all simply by executing on the content marketing and engagement
strategies Ive already shared in detail here and here.
With some effort and smartly-applied strategy, any business can replicate (or top)
these results.
If, a few months from now, you think you may need a last-minute scramble to
succeed, the time to start executing is now.

120

What I Fear Most As a Founder


January 30, 2014

My name is Alex, and Im scared. Heres


why thats not a bad thing, and why you
shouldnt be afraid of fear, either.
I was watching an entrepreneur give a talk about what it takes to build a
successful company.
Being bold isnt enough, he proclaimed with enough enthusiasm to make the
whole room lean in to listen.
He narrowed his eyes and pointed at his listeners.
You have to be fearless.
The room was dead silent as the audience absorbed this seemingly profound
lesson.
The speaker is a brilliant, successful guy whos founded and sold two startups. Ive
learned a lot from him and I admire him tremendously.
And I have no doubt that he is, in fact, fearless.
But if what he says is true, then Groove doesnt stand a chance.

121

As an entrepreneur, I fear a lot of things.


When things got bad and we were close to death, that fear nearly drove me to the
brink of complete emotional breakdown.
When things are good or even great, as they are today that fear refuses to be
suppressed, and I still sometimes lose sleep, dreading (or sometimes even
expecting) the worst case scenario.
And through it all, while that fear has nearly cost me my sanity on more than one
occasion, Ive learned to love it.
Why?
Because they make me a better entrepreneur. Every one of my biggest fears drives
me to ensure that I never have to see them come true.
I hope youll forgive the self-indulgent post, but my goal isnt just to share my own
fears. Its to demonstrate that the fearless entrepreneur stereotype doesnt apply
to all of us, and yes, you can be scared absolutely shitless, and still be successful.
I hope.

The fear of letting down our customers


I started a business because I believed that I could be good at it.
But I started this business a customer support company because I believed
that I could help other small businesses become successful by getting really good
at support.
To date, more than 1,000 customers have bought into that vision. And I think were
doing pretty well at achieving what we set out to do.
But what if we fail?
What if we suffer a technical issue that costs our customers dearly?
What if we fall behind on innovation and allow our users to be lapped by their
competitors, armed with better tools?
There are fates worse than going under, and hurting the people who entrust you
with their business is the most painful one I can think of.
How it drives me: Our customers are the center of our world, and every business

122

decision we make revolves around making them more successful. It sounds like
marketing fluff, but its truly changed the way we run our business for the better,
and it all came from being scared to let our users down.

The fear of letting down our investors


We didnt raise a big venture round, but I did take some early cash from a few
angel investors that I trusted deeply.
Before Groove reached Product/Market Fit, before we had paying customers,
before we had a talented team, before we had any semblance of a real business,
our investors believed in us enough to put their hard-earned cash behind our
dream.
Im incredibly grateful for their help, and we wouldnt be where we are today
without them, but even more than that, Im scared to let down the only people
who were so into Groove that they willingly put their skin in the game, knowing
that as an early-stage startup, the odds were stacked high against us.
Im scared that I might someday have to tell them that they were wrong for
believing in us.
How it drives me: While making our customers grow is essential to making Groove
successful, we cant help anyone if we run out of money. This fear has led us to
take monetization and pricing very seriously, testing and iterating for months to
get to a model that finally worked.

The fear of making a bad product decision


This is one of the fears that weve actually had come true.
In the early days of Groove, we made some huge product fails and it cost us six
months and $50,000, nearly killing the company.
Seeing the fear realized, and then fighting through and emerging on the other
side didnt make the fear go away. Instead, Im now even more worried about huge
product missteps.
This fear has spurred us to make massive changes in the way we develop. By
running lean and building iteratively, we hedge against the possibility that well
have to go through the same debacles again.
Still, like any business, were vulnerable.

123

The fear of past decisions coming back to


haunt us
Since the start, weve been a remote team. We have folks all over the world
working on Groove, and we keep in touch throughout the day using a variety of
tools.
But what if that was the wrong choice?
What if an in-house team really is more effective?
What if our culture were stronger?
Would we be growing faster?
I wonder how much if anything weve given up by not focusing on having a
headquarters where everyone works side by side.
How it drives me: In practice, the decision is pretty much irreversible, and the fear
surrounding that has led us to putting a ton of effort into working together better.
Weve learned a lot in that regard, and Ill be writing about it in the future.

The fear of being consumed by my work


Like most founders I know, I can be obsessive.
Not 60 hours a week obsessive.
More like forget to eat, sleep and acknowledge the people around me obsessive.
Ironically, I have to work really hard to not work too much. And I do make that
effort, for the sake of my own health, my personal relationships and my ability to
run the company.
But Im scared of slipping. Of an impending feature launch or some other crunch
time deadline dragging me into the rabbit hole, and of my own obsessiveness
taking over and never letting me out.
How it drives me: This fear forces me to take time away from work. It feels strange
to say, as I never thought Id have to drag myself out to go surfing, but I do it fairly
frequently, and Im glad I do.

124

The fear of falling out of love with Groove


A lot of very smart, hard-working people build companies opportunistically. They
see a hole in the market, regardless of how well they know the market, and they
fill it. If theyre savvy, they often sell fairly quickly and make out with a nice
payday.
Im simply not capable of doing that.
Groove is a labor of love for me. If I didnt love working on this company every
single day the product, the marketing, the blog, the customer support I
wouldnt do it.
There are a lot of far easier ways to make a living than building a software startup,
and theyre certainly tempting.
But Groove is what I love. And right now, I want nothing more than to make it my
lifes work.
While I have no reason to believe that it will (see: The fear of becoming obsessed
with my work), Im terrified that that might change.
If I ever fell out of love with my job, I hope Id be smart enough (and self-aware
enough) to hand the reins over to someone who can ensure Grooves success. But
what if Im not?
How it drives me: This was a lot harder in our early days, before we had customers
telling us every day about the impact Groove was making on their businesses. I
had to remind myself daily (in fact, I had a calendar notification for this; I literally
reminded myself to remind myself) why I got into this. Im driven to make Groove
successful, so that even if I do fall out of love with the work, the company can go
on without me.

How to apply this to your life and business


Its easy to look at most of the business content out there and conclude that the
people writing it are fearless warriors who dont flinch in the face of danger.
Thats not the only way to succeed.
Its okay to be scared. I know I am.
125

The key is to harness your fears; dont hold crippling fears, but instead turn them
into driving fears that will help you avoid the things youre scared of, become a
better entrepreneur and grow your business.
I challenge you to do this together with me: leave a comment below about your
biggest business fear, and how youre using it or plan to use it to achieve your
goals.

126

How We Grew Our Customer Exit


Survey Responses by 785%
February 6, 2014

Learning the reasons why your


customers cancel is painful, but
its unquestionably valuable.
Heres how we do it.
Truthfully, it sucked. We couldnt deal with the constant bugs. The app isnt ready
for primetime.
As a founder, one of the most painful things in the world to hear is criticism of
your baby.
Especially sharp, stinging criticism from a customer that youve now let down.
In our very early stages when just about every element of Groove deserved
criticism I was terrible at handling anything negative being said about us. It cut
deep, and I almost always let it get to me. Even worse, I did nothing to
systematically collect and measure the feedback I was getting.
Theres no way around it, it still sucks when people point out where youve failed
them.

127

But actively collecting and leveraging that feedback has become one of the most
important drivers for continuous improvement at Groove.
And by testing, measuring and iterating on the way which we collect (and act on)
negative feedback from customers who cancel, weve been able to improve
customer satisfaction and retention, keep Groove growing, and even bring back
some of the customers who left.

The Customer Exit Survey


At first, we had no system in place for collecting feedback from customers who
closed their accounts.
But after seeing it from countless apps I signed up for and canceled, I decided to
give customer exit surveys a try.
We studied dozens of surveys and put together one of our own.
It was a single question (why did you cancel your account?) with a drop-down
menu of options that we had already been hearing from customers, reasons like
too expensive, didnt get value out of Groove, chose another solution, and a few
others.
We sent this survey to every customer who canceled. We even tested four
different emails to get people to respond.
The result?

128

A whopping 1.3% survey completion rate. Pretty awful, and on top of that, the data
was practically useless. Responses were spread across the board in a near-even
split between the top three choices.
After this first test, we had little data and nothing to act on, but we werent done
testing.
Takeaway: While we didnt get tremendous results from our closed-ended survey,
we did clearly see the potential for gathering exit data. But dont discount this
approach; while they didnt work for us, a lot of very successful companies use
closed-ended surveys, so they may work for you.

An Open-Ended Breakthrough
After thinking about how we could get better insight from our exit surveys, we
decided to sacrifice our goal of getting a neatly quantifiable data set, and instead
see what ex-customers had to say when we didnt pre-fill their answers.
We sent out a simple email:

Not only was the response rate nearly eight times greater at 10.2%, but we were
finally starting to get real, actionable data.
Specific bugs that our active customers werent telling us about.
Hang-ups in our user experience that we didnt catch.
Workflow inefficiencies for use cases that we had never considered.
129

Now we were getting somewhere.


Takeaway: By removing the pre-filled answers in our exit survey, we were able to
unlock loads of valuable and actionable data.

A Simple A/B Test That Nearly Doubled


Conversions
We set out to optimize the survey even further, and tested nearly half a dozen
variants.
The winner looks exactly like the email above, except for one small difference.
Instead of why did you cancel?, we ask what made you cancel?.
A tiny difference in framing nearly doubled conversions, and the latter email got a
roughly 19% response rate.
I dont have a deep understanding of the why, but I suspect that why did you
cancel? simply sounds more standoffish and puts the reader on the defensive,
whereas what made you cancel? doesnt have the same accusatory tone.
Takeaway: Its not just doing a survey thats important; you need to optimize your
question(s) to ensure that youre asking them the right way. A simple wording
change can make a big impact on responses.

The Next Level: Customer Exit Interviews


Story time.
A while back, I heard a great anecdote about self-help guru (and brilliant
entrepreneur) Tony Robbins. I dont know if its true or not, but I think theres an
important lesson here.
When Tony was starting out as a speaker, he would approach one or two audience
members after his talks and ask them two questions:
What did I do well, and what could I do better next time?
Of course, he got lots of glowing praise from folks who were too polite to criticize
him to his face, but getting negative feedback proved more difficult. People would
often say things like that was great, your style is invigorating and inspirational,
and I wouldnt change a thing.

130

But that wasnt good enough for Tony.


Hed push: I appreciate that, but this conversation isnt over until you tell me one
thing I can do better the next time I give this talk.
Tony didnt ask for feedback. He demanded it. And it paid off: he used that negative
feedback to improve every single time, and hes now one of the most successful
(and highest-paid) speakers in the world.
Of course, its really hard to be demanding in an email survey. But I wanted to try
and put Tonys experience to work.
We began emailing customers who canceled, asking to set up a five-minute exit
interview. We promised that we wouldnt pitch them, and that we just wanted to
learn how we could make Groove better.
While the response rate wasnt great (around five percent), we did have some
really valuable conversations and got great, honest feedback from former
customers who didnt always give us straight answers right away. Tonys technique
definitely works.
With that said, we dont do these anymore.
The marginal value over the open-ended email survey simply isnt there, and the
resource commitment is exponentially higher.
Im still glad we tested it, and Im certain it would work well for businesses with
smaller customer bases (like consultancies or agencies).
Takeaway: Demanding feedback in a live conversation definitely works. Whether it
works at scale depends on your business; we get enough value out of email
surveys that it doesnt make sense for us, but exit interviews could still be the best
fit for you.

How To Apply This To Your Business


Since weve started doing open-ended exit surveys eight months ago, weve been
able to make a lot of positive changes and fixes to Groove. Retention, along with
many of our usage metrics, have improved as a result of some of these changes.
Weve even started testing recovery campaigns for former customers whose
issues weve fixed; Ill write about that in a future post, but the early results are
very promising.
Taking criticism is hard, but it can be one of the most effective ways to improve
131

your product. And with automated open-ended exit surveys, its really easy to do.
If youre not already doing it, I encourage you to give it a shot. If your experience
is anything like Grooves, youll get a ton of new insight that will help you hold on
to the customers you still have.

Finally, An Announcement
Groove is a customer support company, though we dont talk about that too much
on this blog.
And we dont plan to; this blog is, and always will be about the growth of our
business.
But with more than 1,000 customers, hundreds of support-focused tests and
millions of data points, we do have a lot of valuable support insight into what
works and what doesnt. And now, were chronicling that on the Groove Customer
Support Blog.
Just like this blog, well be posting weekly. And just like this blog, were not going
to pitch you on our product. Just like this blog is focused on sharing our
experiences to make you better at business, our support blog will share our
experiences to make you better at support.
Check it out here, and subscribe if youd like the weekly posts emailed to you. The
support blog email list is separate from this one, so you can choose which content
you want.
I hope you enjoy it, and I hope youll let me know what you think.

132

The 25% Discount that Cost Us


$12,000 (Plus, a Big Announcement)
February 13, 2014

As the new customers rolled in, our


promotion was looking to be a home run.
Unfortunately, it was costing us dearly.
I couldnt help but grin as I watched the new accounts roll in.
Three in the first five minutes.
This is it, I thought. We cracked it.
Another five in the next ten minutes.
Hell yeah. Its finally happening.
By the time the day was over, we had 46 new trial signups. At the time, it was our
biggest day ever.
I practically skipped out of the office that night, relieved and excited that Groove
had finally figured out how to solve the customer acquisition problem.

133

It was early March 2013, and that morning we had pulled the lever on a new
promotion: 30% off for new accounts, on top of our standard 14-day free trial.
Sure, theres nothing groundbreaking about a 25% off deal, but it was the first time
we had ever tried any sort of discount at all.
And just like that, the signups started coming.
There was no stopping us now.
Sixty days later, the promotion was gone. So were most of those early signups.
We were, disappointingly, back where we started.

Why We Ended Our Highest-Converting


Promotion Ever
As a founder, nothing makes me happier than the peaks of entrepreneurship.
Thats because, especially early on, the journey is mostly through valleys.
So to get such instant gratification dozens of new customers at a rate wed
never seen before from a move I thought was highly strategic felt really good.
And thats why it crushed me to admit, not very long after, that it was a failure.

134

But digging deeper than the signup numbers, it was shockingly obvious.
We were getting exponentially worse customers.
Even with the discount, users who signed up with the offer were 12 times less
likely to sign up for a paid account than our usual free trial users.

And for those few that did, just over 30% of them renewed for a second month. To
put that in perspective, thats less than a third of our normal churn!

135

And Groove wasnt doing these users any favors, either.


Our (regular) average user logs in to Groove just over four times per day.
Users who signed up via the offer logged in, on average, just over once per week.
Thats with our improved onboarding and activation campaigns, which were doing
very well with other users.
While Im positive that the poor usage and terrible conversions are deeply
connected, Im not sure where the causation begins.
Either way, there was no way we could continue the offer. Our cost-peracquisition was the same (around $60), but the average lifetime value of the offer
users, based on how many canceled within the first month, would likely never rise
above $30.
With those numbers, we run out of money fast.
All in all, we spent (lost) around $12,000 on this effort, and its worth noting that
not a single user who signed up via the promotion remains with Groove today.
A very painful lesson learned.

How to Apply This to Your Business


Please dont read this post as an indictment of discounts.
For many companies, they work very well.
Instead, read this as a shining example of how what works well for some might be
disastrous for others.
And beyond that, read this as an argument to go deeper than what your vanity
metrics are telling you, and figure out whether your user acquisition methods are
getting you high-quality users that will grow your business over the long term, or
pump-and-dump freeloaders coming along for a cheap ride.
With that said, we have found that certain types of offers work much better for us,
cost us less money, and get us fantastic users.
By far, the best promotion weve since run has been a limited-time extended free
trial.
The users have been great, conversions have been high, and weve been able to

136

help many of them achieve great things.


Which leads me to

A Big, Exciting, $50,000,000 Announcement


We dont write a lot about apps and tools, but we do get a lot of questions about
what we use at Groove.
People keep asking us to recommend our favorite apps, and we keep saying that
weve got something in the works for them.
And thats all weve said.
Its been as frustrating for us to be so tight-lipped about it as it is to hear such a
fluffy non-answer to an important question.
But that all changes now.

Weve partnered up with 19 of our favorite saas apps to offer more than $10,000 in
free software to startups and small businesses.

137

Over the past few months, Ive personally convinced each and every one of these
all-star SaaS companies to extend a special offer just for this launch, and the
response has been incredible.
Weve got heavy hitters that youve definitely heard of, plus some amazing younger
SaaS companies that are already delivering massive value to their users, and that I
personally think will be the next wave of must-have apps:
KISSmetrics (90 Days Free)
Unbounce (75% Off for 3 Months)
Shopify (90 Days Free)
Grasshopper ($50 Credit)
Moz (90 Days Free)
CrazyEgg (90 Days Free)
Drip (90 Days Free)
Wistia (90 Days Free)
Vero (90 Days Free)
Customer.io (90 Days Free)
Zapier (90 Days Free)
iDoneThis (15% Discount)
BidSketch (90 Days Free)
Mention (90 Days Free)
PipeDrive (90 Days Free)
ExitMonitor (90 Days Free)
PlanScope (90 Days Free)
Uncover (90 Days Free)
Stride (90 Days Free)
Groove (90 Days Free)
This is a set of offers that you wont find anywhere else, and its 100% free.
If youve been following this blog, youve seen the difference that the right tools
can make in the growth of a startup. By helping us to understand, automate and
optimize our business, the apps we use have been a huge catalyst for the revenue
progress bar you see below each post.
138

And while the value has been huge, the apps we use arent necessarily cheap.
If youve seen what some of these apps cost (some of them are $500 a month and
up), then you understand why Im so excited that weve been able to put together
these offers for startups and small businesses (like us) that have to make every
dollar count.
As I said, access to these offers is totally free.
But there is one small catch.
Our goal with the Small Business Stack is to empower as many startups and small
businesses as we can, and weve set our sights high: 5,000 companies in 2014. If we
reach 5,000 companies, well have given away more than $50,000,000 in free
software.
We cant do that on our own, and Id be incredibly grateful for your help.
Once you enter your name and email address here, the form will ask you to share
the Small Business Stack via Twitter, Facebook or email. As soon as you do any one
of those, youll get instant access to all 20 offers.
Click here to join!

139

Unlock $10,000 in Free SaaS Apps and


Help Us Give Away $50,000,000
February 20, 2014

Last week we launched the Small Business


Stack to give away more than $10,000 in
software to startups. Heres why
Since weve launched this blog, weve gotten a lot of comments and emails about
the tools we use at Groove.
People want to know what software helps us track the metrics we talk about on
this blog, or the apps we use to manage marketing emails and social media.

140

Now, Ive also heard, time and time again, some variation of the phrase its not the
tool, its how you use it.
And to an extent, thats true.
Spending countless days obsessing over which software is best will bring you
decidedly lower returns than simply picking something anything and just
getting started.
Analysis paralysis is real, and its dangerous.
But if youre already taking action, honing your skills and strategies and seeing
good results from it, then optimizing your tools can have a big impact on your
business.
Its certainly true for us.
Being able to use top-of-the-line SaaS products has given us the luxury of better
insights, better efficiency and better results.
In short, the tools we use have directly contributed to the growth of Groove.
But while these apps have incredible value for us, they aint cheap.
And as valuable as they are, a lot of startups simply cant swing the budget to use
software that costs hundreds of dollars a month.
I know, because Ive been there more than once.
Thats why I was so excited last week to launch the Small Business Stack.
141

I spent months convincing 19 all-star SaaS companies to join Groove in offering


exclusive deals for startups and small businesses, and together, we put together a
package worth more than $10,000 that were giving away for free to everyone that
signs up.
KISSmetrics (90 Days Free)
Unbounce (75% Off for 3 Months)
Grasshopper ($50 Credit)
Moz (90 Days Free)
CrazyEgg (90 Days Free)
Drip (90 Days Free)
Wistia (90 Days Free)
Vero (90 Days Free)
Customer.io (90 Days Free)
Zapier (90 Days Free)
iDoneThis (15% Discount)
BidSketch (90 Days Free)
Mention (90 Days Free)
PipeDrive (90 Days Free)
ExitMonitor (90 Days Free)

142

PlanScope (90 Days Free)


Uncover (90 Days Free)
Stride (90 Days Free)
Groove (90 Days Free)
When we launched the Small Business Stack, our goal was to help 5,000 startups
and small businesses in 2014. If we can do that, well have given away $50,000,000
in free software.
In just one week, weve had more than 1,000 signups; were already 20% of the
way there!
The response has been incredible.

143

If youve joined the Small Business Stack and unlocked these amazing offers, please
leave a comment on this post and let us know about your experience so far.
And if you havent unlocked your $10,000 in free software yet, unlock the Small
Business Stack now.
Once you enter your name and email address here, the form will ask you to share
the Small Business Stack via Twitter, Facebook or email. As soon as you do any one
of those, youll get instant access to all 20 offers.
Youll help yourself to $10,000 in free apps, and youll help us give away
$50,000,000 in software to startups and small businesses in 2014.
Heres the link: www.groovehq.com/software-stack

144

The Meltdown That Brought Our


Startup to Its Knees for 15 Hours
February 27, 2014

As a founder, I always thought Id be


ready when the shit hit the fan. Last
Friday, I learned how wrong I was
Knock, knock.
When the first knock came at 7:30AM, I was still dreaming.
Knock, knock, knock.
Drifting between deep sleep and a groggy haze, I lifted my head, wondering where
that obnoxious noise was coming from.
KNOCK KNOCK KNOCK KNOCK KNOCK
At this point, there was no mistaking it: the banging was coming from my own
front door.
Why would anyone come knocking this early?
My thoughts cloudy, my eyelids heavy, and still wearing only my boxers, I clumsily
stumbled down the stairs and pulled open the door to find my confused neighbor
145

(and good friend), Jon, holding out his cell phone.


Its Adam.
Still half-asleep, I didnt even think to question this bizarre scene. I took his phone.
Adam?
Dude, what the hell? Ive been trying to call you. The app has been down for eleven
hours.
In the two seconds it took my foggy brain to process Adams words, time stood
still. And thats when my jaw dropped, and a wrecking ball planted itself firmly in
the pit of my stomach.

No Time To Be Surprised
I was wide awake instantly. I handed Jon his phone back, sprinted back up the
staircase and opened my laptop, doing my best to mentally prepare myself for the
shit to hit the fan.
But as I saw as soon as I opened Twitter, it already had.

146

The outage had been going on for the entire night, and our customers on the
other side of the globe had been dealing with it for an entire business day without
so much as a peep from us.
They were confused and concerned, and some were downright furious. As they
should have been.
I grabbed my iPhone, which had died the night before, plugged it in and powered
it on. My first calls were to Jordan and Chris, Grooves lead developers, asking
them to come online immediately.
We convened on HipChat and the team got to work trying to find the cause of the
outage.
And when I say that the team got to work, I mean that Jordan and Chris got to
work as I, a non-developer with very little technical expertise, helplessly stood by.
The first ten minutes, for me, were the most agonizing in Grooves history.
While the developers worked, my mind raced.
There are few things worse than working your ass off for years to build a business,
hustling every chance that you get, and running head on into a disaster thats out
of your control and threatens to undo your dreams.
Resisting every urge to punch my computer screen, I began to help Adam respond
to the barrage of incoming emails.
We wrote an email for our customers to make them aware of the outage,
apologize and let them know that we were on it.
As I gave it a final read-through, a pop-up notified me of an incoming message. It
was from Engine Yard, our cloud server management company.
Unsure if the email had anything to do with our current issues, I shared it with the
team on HipChat.
Almost immediately, Jordan shot back: Thats it.

147

Ten minutes later, on the phone with Engine Yard, Jordan learns that the server in
question, scheduled to be retired in five days, had been mistakenly terminated the
night before.
I was angry, but it wasnt totally Engine Yards fault. Not even close.
If we had known about the outage when it happened, it wouldnt have taken us
very long to find the cause. And it certainly wouldnt have been twelve hours
before our worried customers heard from us.
You see, we had server monitoring in place. Except that it was set to send us email
alerts in case of outages.
And since we dont check email in the middle of the night, the entire team slept as
the disaster unfolded.
It was an idiotic, absent-minded, careless, colossal fuck-up.

148

Takeaway: If youre a SaaS company without a round-the-clock team, do this right


now: setup your server monitoring service to call the personal phones of at least
three team members in case of an outage. If we had done that, this story would be
a lot less painful to write.

A Surprising Response From Our Customers


I wanted to cry.
I wanted to throw up.
I wanted to board a plane, visit the office of every single customer who had been
impacted, drop to my knees and beg for forgiveness.
Instead, all I could do was send an email to update our customers:

To my surprise, the majority of email responses that I received were supportive


and understanding.

149

Still, as I continued to check in with our developers as the minutes passed, I


couldnt keep the worst out of my head:
How many customers are we losing?
How much trust are we losing?
How are we going to recover from this?
For a while, things had been amazing.
January was Grooves best month ever, revenue-wise, and February was shaping
up to be even better.
The Small Business Stack had taken off, with more than 1,500 businesses signing
up in the first two weeks.

150

We had just announced a huge new integration with HipChat the day before,
with the HipChat team helping us promote the news and sending droves of new
users to Groove.
How quickly it all seemed to start falling apart. I had just blogged a couple of
weeks before about my biggest fear as a founder: its letting down our customers.
Now, that fear was becoming reality.
Takeaway: Always remember that there are peaks and valleys. For startups, even
when you think youve broken through the worst of it, shit can go downhill fast. No
advice I could give would make this rollercoaster emotionally easier, but knowing
that a steep drop is probably coming up can, at the very least, help you be more
prepared to ride it.

Damage Control

Because the terminated server was our master database, our team needed to
rebuild the entire cluster, which would take hours.
Throughout the process, we did our best to keep customers informed. The emails
we pushed out throughout the day were among the most painful Ive ever had to
send, as I knew just how frustrated and angry I would be if I were in the readers
shoes.

151

152

We also Tweeted like crazy:

153

We overcommunicated, because if a service that I relied on heavily was


inexplicably down, Id want constant updates, too.
After five torturous hours, we finally got the app back up, and two hours later we
restored it to full functionality.
We also published a post on our product blog about the technical details of the
outage.
Based on the conversations Ive had with customers since the outage, our
responsiveness and emails throughout the day prevented more than a few of them
from jumping ship.
Takeaway: When disaster strikes, dont leave your customers in the dark. Outages
can happen to anyone (and they regularly do), but respecting your customers
trust in you and keeping them in the know is critical. Get on Twitter. Get on email.
Get wherever your customers are. Be communicative, be honest, be
understanding, and be apologetic.

Planning for Next Time


Our entire team was 100% focused on the outage and customer communication
related to it for the whole day.
Thats dozens of cumulative hours of productivity and thousands of dollars in
overhead that would have otherwise gone to growing the business, instead of
saving it.
There are costs that we dont fully know about yet, either.
While no customers cancelled their accounts on Friday, I know that some current
trial prospects wont convert over this.

154

Were not sure what impact it will have on monthly churn, or new customer
acquisition. Were not sure if or how much weve damaged the Groove brand, and
that kills me. But when we do have enough data to calculate that damage, Ill
update this post.
Ultimately, we were caught completely and utterly unprepared. While the Engine
Yard error should never have happened, neither should our delayed response and
subsequent scramble.
Since our launch, weve been working hard on enhancing Groove: features, UI
improvements and tackling bugs have all been huge priorities.
Unfortunately, we hadnt spent as much time as we should have on fail-proofing
our infrastructure. While we had our heads down in the sand plowing through
product development, our servers simply worked. And it took an awful wake-up
call like this to realize that we needed to do better.
No longer will infrastructure be a feature to be weighed and prioritized against
others in our backlog. Its the foundation of everything we have, everything we do,
and it will be treated as such.
Beyond simply upgrading our server monitoring to PagerDuty, weve now spent
many more hours of developer time putting together a detailed plan to make our
server infrastructure stronger and more stable.
Were also working on a new push to share more and more transparently
about the development/IT side of Groove, and not just our business growth. Stay
tuned for more on that next week, including a public link to our detailed
infrastructure improvement plan.
Well also be signing up for StatusPage.io (incidentally, a Groove customer) to help
us in case of future outages.
And while I think we did pretty well communicating with our customers
throughout the outage, weve also written a crisis communication plan that will
help us spend less time flailing about next time (as much as I loathe to say it, for
most businesses there will be a next time) before establishing contact with our
customers.
You can find a copy of that plan here.
Just like all of the other regrets I have, if we did these exercises a week ago, I may
have been writing an entirely different post today.
Takeaway: Whether you have five customers or five thousand, spend time

155

thinking about how youll react when not if major issues happen. Think about
infrastructure. Think beyond delivering value to your customers, and think about
what youll do when that value (temporarily) disappears.

Time to Move Forward


A lot of things went wrong last Friday that made me feel more panicked, upset and
guilty than anything has in a very long time.
But a few things went right.
When we finally learned about the outage, our team jumped into action, and Im
proud of how we performed under pressure.
And when we began to talk with our customers about what was going on, I was
surprised at the understanding and appreciative responses we were getting, and
at how few people actually left that day.
To me, thats a glimmer of hope that weve built something special.
Something thats valuable enough that our customers are willing to forgive a
massive screw-up (at least this once) and stick with us.
And while Ill always remember the grey hairs I earned and the lessons I learned
last Friday, that hope is why Im not going to dwell on the issue any longer.
That hope is why we march on.

156

Dont Make THIS Customer


Communication Mistake
March 6, 2014
He wasnt the first customer to say we screwed up, and certainly wont be the last.
In the aftermath of our outage two weeks ago, I received a stinging email from one
of our customers...

157

As hard as it was for me to read, he was absolutely right.


As open and consistent as weve been sharing about our growth efforts on this
blog, weve been terrible at communicating whats going on behind the scenes on
the development side.
While Im very happy with the job weve been doing providing useful information
to the readers of this blog, we havent been doing the same for the people who
keep our lights on: Grooves customers.
That changes now.
Takeaway: We all market to our target customers, but its critical to communicate
with existing customers, too. Theyre quite literally your most valuable
audience.

We Spend 90% of Our Time on Product


Its not that we dont have war stories from the development trenches.
Not even close.
For every grey hair I have from tackling business growth challenges, I have two
grey hairs and a forehead wrinkle from obstacles weve come up against trying to
make Groove the best product it can be.
This blog makes it look like we spend our whole day doing marketing, but the
reality is that the overwhelming majority of my time is spent on product: testing,
roadmapping, hunting for bugs, supporting our development team in any way I
can.
It has to be that way. As much as we blog, Groove is a product company. If the
product sucks, we fail.
But because of this blog, its easy for anyone to think that growth is where our sole
focus lies.
Up until now, our communication about product development has been confined
to an awful excuse for a product blog which has had exactly two posts in the last
six months. Beyond that, we certainly let customers know about updates when we
talk to them or when they email us for support, but thats about it.
Frankly, in hindsight, thats insane.
We know the value that consistent, open communication has from this blog. It
158

helps to build trust and develop deep relationships with people. Why wouldnt we
do the same with our customers?
Takeaway: Its not the customers job to know whats going on with your product.
It's your job to tell them.

How Were Going To Do Better


This week, were officially launching The Groove Report.

Every Monday morning, well post an update from the developers here at Groove.
Well share:
What we worked on the week before
What well be working on in the upcoming week
Takeaways and lessons that we can all learn from
Were not going to pick and choose what we publish based on how sexy it is. The
Groove Report is a full access backstage pass to what our developers are doing,
from the boring (bugs and tiny code enhancements) to the awesome (new
features, integrations and major UI improvements).
First and foremost, The Groove Report is for Groove customers. We want to be as
open and honest with you about our product development as we are about our
159

startups growth. Subscribe to the blog to learn exactly whats going on with your
customer support software.
In addition to our customers, I hope other startups will find it interesting, too.
When youre doing your own thing, its hard not to think about what others are up
to. The Groove Report will give you a sneak peek at how another growing SaaS
startup is handling product development on a very granular level, and what our
developers are learning.
Of course, this changes nothing for the Journey to 100K blog or our Customer
Support Academy, both of which will still get weekly updates. The only difference
is that well (happily) be working harder to deliver even more content thats
transparent, interesting and useful.
You can find the first post from The Groove Report (from this Monday) here. If
youre interested in following along and learning with our development team, I
hope youll subscribe.

160

How We Grew Conversions 100% by


Rethinking Our Design Strategy
March 13, 2014

Our customers were happy, our product


was strong, but our conversion rate was
awful. Heres how we changed that
I was on the phone with a marketer friend; an expert who some of the biggest web
companies in the world call for guidance on conversion optimization.
To be completely honest, Im surprised youre getting any
conversions at all.
His feedback was grim, but it was clear. And I knew it was right.
Theres no narrative, the messaging is all over the place and it
doesnt give me a single good reason to do business with you.
Sometimes at least for me it takes having someone else say it to realize the
truth thats been right in front of me all along.
On the product side, things were fantastic. We had recently achieved
Product/Market Fit, and our customers were loving Groove.

161

On the marketing side, this blog was bringing us thousands of new visitors, but at
2.3%, our conversion rate was terrible.

Of course, not all traffic is valuable. For plenty of people who read this blog or visit
from Twitter or Hacker News, Groove is not the best solution. Only a fraction of
our traffic consists of highly qualified prospects that were the right fit for, but we
needed to do a much better job at reaching that segment.
At 2.3%, we wouldnt stay in business very long.
We needed a big win.

Five Things We Did to Get


Ready to Redesign GrooveHQ.com
If we werent smarter than before, we were, without a doubt, more experienced.
We knew how devastating it could be to jump into an overhaul blind.
The last time we did that, it cost us six months and $50,000.
This time, we were going to do our research first.

162

1) Learning Everything We Could


We knew the site wasnt performing, but in order to do better, we needed to figure
out why.
We started by reading everything we could get our hands on, online and off, about
landing page design.
Some of the most useful free resources we found were:
Anatomy of a High Converting Landing Page by Neil Patel
How To Write A Landing Page With A 500% Conversion Lift by Michael Alexis
Does Optimization Ever End? by Conversion Rate Experts
10 Principles of Effective Web Design by Vitaly Friedman
Broadening Our Thinking On The Practice of Conversion Rate Optimization
by Rand Fishkin
Landing Page Best Practices Interview with Oli Gardner
The 10 Commandments of Landing Pages That Work by Steven Lowe
Takeaway: Whenever I take on a project, I make it a point to always try and learn
from people smarter and more experienced than myself. If youre going to invest
the time and resources to build a site, invest the time and resources to
understand what works for others. It wont all work for you, but it will pay off.

2) Talking to the Experts


Our next step was to go deeper into figuring out why our site was failing. To
validate our quantitative results by getting qualitative feedback from people who
knew what they were doing.
We asked nearly a dozen experts for feedback on our site, including:
Three optimization bloggers with nearly 200,000 monthly readers between
them
A landing page agency CEO
Two marketers behind businesses that are often written about for their
growth hacking
We didnt want to skew their feedback, so we didnt tell them our conversion rates.
Instead, we asked open-ended questions about what they thought of our site,
based on their experience and expertise.
The results werent pretty, but they were massively helpful.
In short, our messaging and positioning were somewhere in the space between
pretty awful and unbelievably awful.

163

Customer support is a product, not a problem. What problem are you


solving, exactly?

Youre selling me on how easy it is to set up, but you havent even
convinced me that I want to set it up yet.
164

We were, to put it bluntly, missing the point.


Youre talking to your customers the way you think marketers are
supposed to talk. Its marketing-speak, and people hate that.
I knew this was true, and I knew it was wrong. I told him I understood that we
should just be using our own voice, and talking the way we normally do. He
interjected:
Nope, you should talk like your customers do.
Takeaway: If youve been building relationships with people who know more about
marketing than you do, there are few things more valuable you can ask for than
expert feedback on your strategy. They may not have all of the answers, but youll
have far more insight than you started with.

3) Talking to Our Customers


We set out to learn, as our friends suggested, how our customers talked and what
was most important to them.
We set up a power report in KISSmetrics to identify our most engaged users:
those who managed more than 40 emails per week.
And then we picked up the phone.
We didnt send out surveys, we didnt email them questions, and we didnt ask
anything that could be answered with a yes or no.
We knew that if we really wanted to get the insight we needed not data, but
words the best way to do that would be through having actual conversations
with our customers.
Through phone calls and Skype, we asked our power users a set of probing
questions, designed to not only help us understand their problems and what they
loved and hated about Groove, but to give us deep insights into the exact words
they used to describe those things.
The four questions we asked were:
What problems were you hoping Groove would solve when you signed up?
What has your experience been like so far?
What was getting started with Groove like?
What was your aha moment the moment you knew you loved Groove?
You can find notes from one of our calls, including the responses from a customer
(with identifying data scrubbed), here.
165

Not only were the responses that we got full of surprises for us, but many of them
would become the foundation of our messaging for the new site.
Takeaway: Your customers can teach you more about marketing your business
than anyone. Ask them lots of questions and look for trends in the responses; if
youre hearing the same things over and over again, its probably worth focusing
on in your marketing.

4) Talking to New Customers


We knew what our customers were thinking, but we wanted to go deeper into the
decision triggers that made people sign up for Groove. If we learned exactly why
people signed up while the decision was still fresh in their mind, we would know
which positioning and messaging we would need to focus on to elicit the same
behavior from others.
As we learned in our previous customer development campaigns, sometimes the
best way to get an answer to a question is just to ask.
We set up our welcome email to ask new customers a simple question:

The results have been overwhelming. This email gets a 41% response rate, and has
given us more business insight than any email weve ever sent, with responses like:

166

Just like our customer surveys, the answers weve gotten from this question have
had a massive impact on our marketing.
Interestingly, we found that the answers to this question varies widely between
customers who answer it immediately after signup, and those who have been
using Groove for a week or longer. After a few days, the responses begin to skew
more toward specific features within the app.
For that reason, we felt it was important to ask the question right away, so that
the decision was still fresh in the users mind.
Takeaway: Figuring out what drives your customers to buy is a lot easier than you
might think. All you have to do is ask; immediately after signup is best.
167

5) Defining Who We Are and Who We Want to Be


While the most important thing would be to develop messaging around our
customers, we also wanted to make sure we were building Groove to be the
business that we wanted, too.
On the advice of one of the entrepreneurs we had talked to in our initial research
stages, we decided to interview ourselves.
The exercise we did was very similar to the one we performed when we were
figuring out what this blog was going to be: everyone on the Groove team
answered a set of questions that we designed to help us not only figure out who
we were, but whether we were all on the same page about it.
You can find these questions and steal them for your own brand development
efforts here.
This exercise was invaluable. The conversations that it started and the conclusions
it led to helped our team grow closer and more cohesive than weve ever been.
Armed with our research, our customer insights and our own answers, we started
to build.
Takeaway: Before you can tell your story, you have to internalize it. It sounds
simple, but a basic exercise like the one above can bring your team closer together
and make you much more prepared to talk about your business.

How We Built a Copy-First Design


In every prior iteration of our site, we put aesthetics first.
More than anything, it needed to look nice.
We would build designs, draft copy, and then cut or rewrite our words to fit the
design.
Looking back, this was insane.
Not only was it expensive changing text in HTML is much easier than re-doing
design it forced us to compromise on the single most important asset of our
site: our message.
We were painting our house before we built it.
This time, we took a different approach.
We took the data that we got from our reading, our expert feedback, our customer
conversations and our own introspection, and we thought about how we would
tell the right story this time, based on what our findings were telling us.
We knew that we wanted to try a long-form landing page, but that was about it.
168

And while we wanted copy to be the lead here, we found it very hard to simply
write without any structure.
So, using Balsamiq, we built a very basic wireframe of a long-form page, guided by
design elements from sites that we liked (and knew converted well), like
CrazyEggs and a 2011 sales page for Highrise from the team at Basecamp (formerly
37Signals), among others.

Most importantly, we didnt wed ourselves to this layout. We simply used it as a


guide, knowing that it was flexible and fluid, and that we would shape it around
the copy we wrote.

169

And then we wrote that copy. Pages and pages and pages of it, using everything
we learned in the weeks before.
We also knew that we wanted customer stories to feature prominently on our site.
We wanted people to be able to visualize themselves in the shoes of a Groove
customer, reaping all of the benefits of doing business with us.
So while we wrote, we asked our friend (and Groove customer) Allan Branch at
LessFilms if he would help us with a testimonial video featuring his SaaS business,
LessAccounting. In just a few days, they produced a brilliant piece for our
homepage.

We wanted the site to feel like a conversation with the reader, so as we wrote, we
read it out loud to each other, hundreds of times.
We wrote two totally separate narratives around the problems that our customers
faced. We chose the two we did based on the trends in our customer feedback.
Within each one, we wrote dozens of headline and copy variations to test.
It took us writing fifty headlines to come up with just five to test. We led with
benefits, not features. With focused on real problems that we solved rather than
vague descriptions of Grooves use cases. We tried to show exactly why Groove
was the best option to solve our readers problem. We included validation
elements and multiple calls to action. We spent days crafting the way we
presented our offer.
We edited, cut and rewrote nearly everything until we were satisfied that we had
something we could build: finally, a starting point.
And only then did we start to design.

170

We bended and rearranged our wireframe to fit the copy we had written, and then
we built a mockup from that.

We werent interested in spending months or even weeks designing and


developing before launch. We would sacrifice perfection in the name of shipping
171

it, and four days later, we had a working prototype that we were ready to test.
Takeaway: Im not disparaging good design; hell, I obsess over the stuff. But
focusing on design at the expense of content can be deadly. To find a balance, we
had to reverse course and put design in the back seat, taking a copy-first
approach.

Results and Looking Ahead


It may sound anti-climactic, but launch day didnt really mean much of anything
for us. Our data was far from statistically significant, and it took about ten days to
finally get viable numbers.
But once we did, the results were incredible.
Our conversion rate, previously 2.3%, was now 4.3%.

172

Conversions nearly doubled!


Over the following weeks, our tests and tweaks drove conversions up to nearly
4.7%, where we hover today.
There are still many stones left unturned. We have hundreds of tests left to run,
and lots of insights left to gain.
Some of the steps were taking:
Weve installed Qualaroo and are already getting hundreds of valuable
responses as to why visitors arent converting.
Were continuing to A/B test headlines, subheads, images and calls to action
using Optimizely.
Were wrapping up a short-form landing page to test versus the existing
long-form one. Personally, Im most excited about this test.
Takeaway: Design and development are processes, not events. Youre only done
when youre ready to stop growing your business. Theres always more to test and
tune.

How to Apply This to Your Business


This post was by no means an exhaustive list of everything we considered and
tried in our site development. That would be too long and too boring to publish.
Nor is it an ultimate guide or end-to-end how to for landing page design.
Its simply a story about what worked for us in achieving our conversion rate
gains, along with a set of key takeaways with ideas to try in your own business.
If youre struggling with an under-performing site, use the above exercises to help
you think about how to find a breakthrough.
If your site is doing well, try some of the tactics (like the welcome email) to make
your business even more successful.
Above all, I hope youve learned that talking to people experts, customers,
prospects, coworkers is the most important thing you can do, not only in your
design, but in your business. It will shape marketing, product, strategy and just
about everything else.
I challenge you, whatever stage youre in, to go and ask lots of questions, and then
listen carefully. What you learn could completely change your business.

173

How Our Startup Beat Burnout


March 19, 2014

Our team was working long hours and


teetering on the edge of burnout. Heres
how weve managed to turn things around.
Weve, uhhh, wrapped up the chat updates, and, uh, fixed the Twitter
bug, along with a few others. Tomorrow, well get through the rest
of them.
As I listened to one of our developers take me through the days progress, I could
hear the exhaustion in his voice.
He was tired.
We all were.
This wasnt some aha moment. Wed been feeling this for weeks.
While Groove was growing rapidly, so was our teams workload. Without new hires
(yet), more and more work kept falling on the same shoulders.
More and more days were ending with long, exasperated sighs.
It was wearing on us.

174

And it wasnt just a feeling.


Our productivity was slipping. Over four weeks, our Pivotal Tracker velocity
dropped by nearly 20%.

Now, velocity is not an exact measure of productivity. But it is a quantifiable


metric of how fast were completing tasks, and together with our own
observations of our productivity slipping, it painted a grim picture of how much
work we were getting done.
There isnt a single person whos worked for a startup who doesnt understand
that every now and then, you need to push a little bit harder.
When youre scrambling to grow a business, there are times when putting in extra
hours is simply unavoidable. Youll have launches, deadlines and do-or-die
emergencies.
Thats just a part of the game, and the rare 12-hour day wont kill you.
But when every now and then turns into a regular occurrence, or worse, every day,
youve got a serious and dangerous problem on your hands.
Thats where we were.
It simply wasnt sustainable; the burnout needed to be stopped.

175

Vacation Time Isnt The Answer


Ive written before about how much I value work/life balance.
If we burn out, nobody wins.
But as more and more seemingly urgent tasks come along, priorities have an
unfortunate tendency to shift in the wrong direction.
For too many myself included the answer might have seemed as simple as
take a vacation.
Its not like we dont allow for vacation. Everyone on the team is allowed to take as
much time as they need.
The problem was that nobody was actually taking that time.
Through some very frank conversations, the reasons why became pretty clear:
fear and guilt.
The team was scared; work was already piling up, and if they took time off to
recharge, the incoming work wouldnt stop, it would just be there when they got
back, worse than ever. They were (rightly) scared that knowing this, they wouldnt
be able to enjoy their time off.
Another developer mentioned and others agreed that he felt guilty about
leaving his workload behind for his teammates.

Wow.
Either one of these reasons would be enough to drive many people away from
vacation forever. Together, they ensured that nobody ever risk a day off.
Takeaway: Being entitled to vacation time does nothing to help with stress and
productivity; only actually using it can do that. Simply offering time off to your
team may not be enough.

176

The Three Steps We Took To Fix Things


To be clear, this wasnt a failure on the teams part by any means.
Nor was it the fault of our ever-growing task list.
This was a management failure, pure and simple. I didnt see it coming. I didnt
plan for it. And I didnt take action to fix it until it was bordering on too late.
But finally, I had no choice but to do something.
I tried a lot of things, but three in particular were instrumental to getting us back
on course:

1) Hiring A New Developer


The most obvious solution was also the one I had been putting off the longest, to
the detriment of our whole team. Hiring is risky: it strains a startup budget, and
making the wrong choice threatens to throw off a small companys culture and
dynamic. To me, that was (stupidly) enough to keep pushing hire a new dev
down into next weeks to-do list, week after week.
That wasnt an option any longer. Ive been fortunate to build a network of
connected people, which made getting introduced to a few highly qualified
developers pretty easy. I hired two talented programmers for month-long test
contracts, and one of them ended up becoming a full-time Groove employee.
This step, bringing our team size to six, almost immediately began to relieve
pressure from the rest of our company.
Takeaway: Dont wait to make a hire until your team has already suffered. Do it as
soon as you can afford it; if youre growing and are willing to rework your budget
to make this investment., Id urge you that you can make it work much sooner
than you think.

2) Making Not Working Work


It was obvious that offering vacation time wasnt nearly enough to get people to
actually take it.
Even encouraging people to take time off wasnt enough when their workload
simply wouldnt allow it.
We had to make it work. And to do that, the workload had to change.
We took a deep, unforgiving look at Pivotal Tracker.

177

The truth is, we werent getting that many more mission-critical tasks. We were
just flagging them as mission-critical because they were critical to keeping our
productivity in line with the previous exhausting, overworked weeks.
When we took the time to do a reality check and think about what truly needed to
get done urgently, the list began to shrink, we were able to re-prioritize and push
back less important tasks, and the workload began to become much more
manageable.
All of a sudden, taking a vacation was no longer outside of the realm of possibility.
Takeaway: Growth thats achieved at an unsustainable workload is just that:
unsustainable. Youll have to pull back the amount of work sooner or later; waiting
too long can cost you dearly.

3) Setting An Example
Fear and guilt werent just keeping my employees from taking time off.
They were keeping me put, too.
I had the same fear that my own tasks would pile up to unmanageable levels if I
stepped away, even for a day.
178

I also had overwhelming guilt about the idea of taking a vacation while my team
was hammering away: how can I ask them to work if Im not going to?
But, as one of my founder friends and mentors explained to me, I had to lead by
example.
So, in December, for the first time in a long time, I took a week off and went to
Maine. In fact, I forcibly froze all non-critical tasks on our to-do list and closed the
Groove offices for an entire week after Christmas. Nobody was allowed to work.
The week we returned was our most productive in months. And since then, Ive
made it a point to take regular time off to recharge myself, and the rest of the
team has followed suit.
Takeaway: Being a founder or CEO is no excuse to work yourself into the ground.
On the contrary, if you want your team to be less stressed and more productive,
lead by counter-intuitive example and take a vacation.

Results And Moving Forward Sustainably


In the four months since weve started our burnout-battling efforts, the results
have been impressive.
Our velocity has increased by 38%.

And each team member has taken an average of 1.7 days off per month (not
179

including weekends), compared to less than 0.4 previously.


But moving forward, theres more work to be done:
Better tracking of Employee happiness: productivity is only one indicator of
how stressed out an employee is, and a terrible one at that. I need to do a
better job of tracking our teams stress levels. Im looking at 15five.com as an
option for this.
Better systems for ensuring time off gets used: were exploring systemsbased approaches to making sure our team gets the rest it needs.
In the comments, Id love to hear about your own suggestions and experiences
managing your teams time off, productivity, stress levels and happiness.
Leave a note below: lets learn from each other so we can all do better.

180

The 3 Deadliest Challenges of Scaling


a Startup
March 27, 2014

Once we started seeing real growth, we


were excited to be over the hump.
Unfortunately, the hard work had just begun.
I was stoked.
Really stoked.
And I had every right to be; this was a big milestone.
Hitting Product/Market Fit meant that we were no longer scrambling to build
something of value.
We had it. People were buying it. They were loving it.
And now, our job was to scale it.
Over an after-work beer, I excitedly told my friend an entrepreneur several
years (and a couple of successful companies) ahead of me how great it felt to be
at this point, and how eager I was to finally be able to turn our grand plans for
Groove into reality.

181

The features wed get to build, the sales channels wed dominate, the forever-upand-to-the-right growth chart wed undoubtedly ride to the very top.
I was so pumped up that when he looked at me over his glass with a knowing eye
and said listen, thats awesome, but whatever you think youre going to do over the
next year, divide it by three, it barely even registered.
I ignored it, the conversation moved on, and within a few minutes, I had
completely forgotten about his remark.
In fact, I didnt think about it again for months.
Until last week, when I met my friend again; this time, for lunch.
As we filled each other in, I was far less animated than I had been in our meeting
many months before.
I was upbeat, and I was excited about our direction, but my enthusiasm was
dampened: our growth was strong, but it had brought with it new challenges that I
was totally unprepared for, and it felt like new obstacles crept up every day.
He knew exactly what I meant. He had seen it all. And over the next hour, he
shared his own invaluable experiences and helped me break through many of my
own mental blocks.
I left that lunch with new ideas that helped Groove overcome some of our most
frustrating scaling challenges.
As I thanked my friend, he got up to leave.
But not before he shot me a sly grin and a friendly, well-deserved I told you so.

Scaling Is The Hardest Thing Weve Ever Done


As we sit on the cusp of $50,000 in monthly revenue, Groove looks a whole lot
different than we did even a few months ago.
Our short-term goals are different.
Our day-to-day priorities are different.
And most importantly, our challenges are different than theyd ever been.
Building a product that people loved was hard, theres no doubt about that.

182

It took us a long time, and a lot of money, with a number of setbacks and neardeath experiences along the way.
To an extent, I knew how hard that would be. I had done it before, and I had some
idea of what to expect.
But my last company was acquired before we had to scale. This next stage was
completely uncharted territory for me.
And now, as I look back at what weve battled, learned and overcome in the past
several months, and every battle yet to be fought, one thing is clear to me: scaling
is, without a doubt, the hardest part of building a business.

183

The 3 Biggest Scaling Challenges Weve Faced


Weve hit literally hundreds, if not thousands of new obstacles as weve worked to
scale Groove. But most of them fall into one of three distinct categories:

1) Scaling Shifts Your Teams Focus


I cringe when I read Derek Sivers story about the cost of an unclear email:
At my last company I had about 2 million customers. When writing
an email to everyone, if I wasn't perfectly clear, I'd get 20,000
confused replies, which would take my staff all week to reply back to
each, costing me at least $5000 plus lost morale.
Ouch.
We dont have two million customers, but I sure as hell feel his pain.
When we had 100 users, rapidly building new features was easy. So was testing
major product changes, or launching a third-party integration.
We just did it.
When a couple of users ran into issues because of their browser of choice or
another plugin, we simply helped them work through it.
It was simple.
Now, we have thousands of users using a host of browsers, apps, email providers,
operating systems and other variables that all impact the way Groove functions.
Launching a new feature without ensuring that it works for the majority of those
customers would mean many thousands of dollars in lost time: time spent emailing
back and forth with customers, researching new bugs and issues and ultimately
building and deploying fixes.
And even with all of the preparation and testing that we now do before pushing
updates, customers still run into issues.
With more customers pushing our product to its furthest reaches, bugs and
incompatibilities are being found all the time.
This isnt unique to Groove. Every single software founder Ive discussed this with
agrees: more customers means more bugs.
And more bugs means less time for our team to work on everything else.
184

Simply put: everything moves slower.


Takeaway: Youre not going to be able to move as quickly or as aggressively as
youd planned. But thats okay; dont let growth come at the cost of your existing
customers experience.

2) Scaling Is Expensive
Early on, our costs were, for the most part, fixed.
Our infrastructure could easily handle the first few hundred customers without
much issue, and the products and services we used all gave us plenty of wiggle
room for early growth without any cost increase.
But now, as the number of customers were supporting rises, so do our costs.
Every expense gets bigger:
Servers and the infrastructure to support them
Analytics and marketing apps that price based on traffic or subscribers
Back-end software that prices based on the actions of our customers
In a perfect world, every incremental dollar of revenue would go toward hiring

185

new talent to continue helping us grow faster and smoother.


But as we grow, it gets more and more expensive just to keep the lights on.

Dont get me wrong; were making more money too, and our projections are
strong, but were not profitable yet, and watching each new expense eat away at
our runway can be a scary thing.
Thats why were so focused on things like pricing and conversion optimization;
these arent mental marketing exercises that we do so we can blog about them.
Theyre going to mean the difference between life and death.
Takeaway: The bigger your business gets, the more expensive everything will be.
Be careful not to let your costs scale faster than your revenue.

3) Scaling Amplifies Everything


As we grow, the amazing feedback that we get from our customers goes farther
and farther.
We see it all over Twitter, mainstream news sites and blogs weve never heard of.
The network effect of having lots of happy customers is incredibly valuable, as it
helps us reach more and more new customers.

186

But that reach isnt all roses.


Just as it amplifies the good, scaling amplifies the bad.
When we had a major outage that crippled us for an entire day, people knew it.
It wasnt just an issue for our handful of customers anymore; it created hundreds
and hundreds of rightfully frustrated customers, and was seen by hundreds of
thousands of people on Twitter.

Thats a lot more damage to our brand, and a lot more trust that we had to win
back.
Takeaway: Youre not living in obscurity anymore. Good news travels fast, and bad
news travels faster. Know what to do when the shit hits the fan, and be prepared
for the climb back from every setback.
187

How Were Working Through The


Challenges Of Scaling
Limited focus, limited time, limited money and huge distractions are all obstacles
that stand in the way of a growing startup and its goals.
So how do we overcome those challenges?
Well, truth be told, were still working through them.
We have a lot to learn, and a long way to go.
But weve had more than a few wins and a lot of valuable advice that have led
us to put our scaling eggs into two important baskets:

1) Future-Proofing
Its not enough anymore to fix things as we go along.
While it ties up cash and keeps us from tackling our product roadmap as
aggressively as Id like to, were making long-term investments into ensuring that
well have the resources and stability we need to be a strong business in the long
run.
Were hiring new people and investing in them to keep our team happy and
productive.
Weve spent time rebuilding our IT infrastructure from the ground up so that our
product can be more stable and reliable for our customers.
Were thinking hard about future situations that we may not be expecting (like
outages) and making sure that were prepared for them.
These investments wont help us double our conversion rate overnight or even get
a single new customer in the short term, but theyre absolutely critical for
ensuring (or at least maximizing the chances) that Groove is around for a long
time to come.
Takeaway: Dont be short-sighted. If you can, invest in the things that will allow
you to focus on growth without worrying about disaster. If you cant make that
investment, then youre not ready to scale.

2) Building Systems
There are a lot of things about our business that well never fully automate.

188

Development, marketing, customer support; these all require people to be deeply


involved.
But within those departments, there are systems we can build (and have built) to
automate various processes that make our entire operation scale more smoothly.
Unsurprisingly, we rely heavily on Groove for customer support. And as weve
grown, we begin to use it in different ways than we had in the past. These days,
were a lot more reliant on the automation features to scale our support without
hiring new people.
On the development side, we lean on a number of apps to reduce the amount of
work our team has to do by hand.
For marketing, weve purchased apps and built systems to streamline our email
campaigns, our landing page development and even the development of this blog.
Well never automate something that could be done better by a human, but scaling
our business has forced us to look very carefully at ways to take repetitive tasks
out of the hands of our team.
These systems have played a huge role in freeing us up to focus on the more
important challenges we face.
Takeaway: Some things simply dont automate. For everything else, build systems;
theyre a lot easier to scale quickly than humans.

Dont Let This Post Scare You


Theres no question about it: scaling is really hard.
But its also doable.
Sure, were not moving as rapidly as Id dreamed.
But by focusing on building systems, future-proofing our business and continuing
to make sure that every single customer has an amazing experience, were slowly
but surely getting closer and closer to our goal.
Sooner or later, were going to get there.
And believe me; if we can, then you can, too.
The most important thing to remember is this: dont do what I did. Dont assume
that once you get over the hump of Product/Market Fit, the hard work is done.
The first stage may have been tough, but its only now that the true grind begins.

189

3 Lessons Learned From Testing


Hundreds Of Onboarding Emails
April 3, 2014

We set out to build a better onboarding


experience. Here's what we found.
Onboarding Confusion

It didnt matter.
None of the marketing in the world the redesigned site, the conversion hacks,
the blog meant a thing if we couldnt get users to stick around.
With a trial-to-customer conversion rate of just over 8%, we had to do better.
Having spent a lot of time and effort rebuilding our marketing site from scratch

190

with great results, we suspected that wed have to take a completely new
approach.
As wed learned from our site redesign, asking "how can we get users to stick
around?" (or, in the case of the site, how do we get them to convert?) was the
wrong way.
We had to ask: "how can we serve our users better?"
How can we make their trial so good, and the value they get from it so high, that
becoming a customer will be the obvious choice?
Part of that is on the product side: weve been focusing hard on our onboarding
user experience since we started, and were continuing to test a variety of
changes.
We know that the product can deliver massive value to users, because we see it
every day.
But we also know that helping a user bridge the gap between sign-up and high
engagement can have a huge impact on how much value they get from the app,
and, in the end, whether or not they convert.

Changing Our Perspective


In the past, if you had asked me why we send onboarding emails to our trial users,
I would have said, without missing a beat, "to get them to use Groove."
It seemed so obvious.
And if you look at the emails we used to send, it was obvious:

Welcome Email

191

Useless product tidbits that had little to do with what the user actually wanted.
Our metrics showed it, too: average open rates hovered around 28% for the first
email. Great for marketing to prospects, terrible for a someone who signed up for
your product within the last five minutes.
The painstaking process of redesigning our site with a focus on what the customer
wants and not what we want them to do was absolutely transformative.
It changed the way we thought about our business.
And it was time to apply those changes to our onboarding emails, too.
In our redesign research, just like we had asked probing questions about our
customers experience using our product, we had also asked a number of
questions about our customers onboarding experiences.
We asked about their first login experience.
We asked about their learning experience.
We asked about the emails we had been sending, and how useful (or useless) they
had been.
We learned a lot. Especially about how bad our onboarding emails were.
In talking to our users: they simply dont care about "getting more out of their
Groove account."
They care about real things.
Happier customers.
More efficient workflows for their team.
Thats what those emails had to deliver. And so thats what we set out to do.
Takeaway: There could be a huge gap between what youre telling your customers,
and what they want or need -- to hear. The only way to find out the truth is
surprisingly simple: ask.

The Three Biggest Wins From Our


Onboarding Optimization
During the process of writing our new emails, we tested hundreds of different
192

emails, some with only very minor tweaks. Subjects, bodies, to/from fields, calls
to action and more.
And we tracked the results closely.
Open rates, click-through rates, engagement, conversion from trial, retention.
We ended up with many thousands of data points, but only four clear wins.
By far, four key improvements had the biggest impact on how much value our
users got, and ultimately, on trial-to-customer conversions.

1) "Youre In" Email


This email is the flagship of our onboarding sequence. Its the first thing anyone
who signs up for Groove gets in their inbox.
It asks a simple question: why did you sign up for Groove?

Why Did You Sign Up?

With a 41% response rate, we get massive amounts of qualitative marketing data
about the "decision triggers" that drive people to sign up for Groove.
Aside from that, this email accomplishes three important things:

193

It establishes a relationship between the customer and me (the CEO).


Emails that came directly from me, rather than from a nameless Groove account,
performed better across the board. We learned that when users know that they
have a direct line to the CEO, they feel more connected to Groove, and are less
likely to quit if they hit a snag.
It helps us identify any unique needs that the user may have.
Knowing the specific reason a user signed up for Groove helps our team
customize our interactions with that user to ensure that the product is perfect for
them.
If they signed up because Zendesk is too complicated, we focus on walking them
through processes that theyll recognize from Zendesk that are simpler to do on
Groove.
If they signed up because their team is growing rapidly, well focus on showing
them how to easily add and onboard new employees.
It sets the stage for whats coming.
Whats noticeably missing from this email is any sort of product-related call-toaction (e.g., "go download our mobile app").
Thats very much on purpose.
In our testing, we found that product emails immediately after signup went largely
ignored.
This may be because our in-app walkthrough, which we spent a lot of time
improving, is good enough to keep the user engaged in their first session.
However, we did find that product emails help later on in the process, and that
adding the note letting the user know that well be sending those emails actually
increased open rates for the messages that followed by about 8%.
Takeaway: Counterintuitively, a product-focused message was not the best
performing post-signup email. A different approach has given us invaluable insight
for marketing, support and building relationships with our customers.

2) Behavioral Triggers
Our old email drip was "standard," in that every single user got the same 14-day
sequence.

194

A user who logs in three times per day and is highly engaged from day one would
get the same exact emails as a user who never logged in after their first session.
This was bad.
Those two users are of completely different mindsets, and theyre at totally
different points in the trial cycle.
Sending advanced-level product emails to disengaged users is like asking "would
you like fries with that?" before a customer even steps up to the counter.
We tested customizing the email sequence based on user behavior, and it turned
out to be one of the best things we did.
At first, we did this manually. It was painstaking, but the results made it clear that
the effort was worth pursuing (and automating).
End-of-trial conversions increased, on average, by 10% or more in most of our
cohorts.
Now, a user might get an email like this on the third day of their trial:

Mailbox Created

Or, they might get this one:

195

Mailbox Not Created

Or one of several others.


In our 14-day sequence that, for most users, includes six total emails, we have 22
different messages that go out based on user behavior.
Takeaway: Startups stress over hyper-targeted marketing, but once a user signs
up, we treat them all the same. Two people using your product can still have very
different needs, and your onboarding emails should reflect that.

3) The Winback
Another mistake we were making was abandoning the users who abandoned
Groove.
We had a 14-day sequence that coincided with our 14-day trial, and that was it.
If the user didnt convert, theyd stop hearing from us.
As we learned in talking to some of those users, including quite a few who ended
up becoming customers later on, we were leaving customers on the table.
We heard, more than a few times, sentiments like "I liked Groove, we just werent
ready for it."
Just because Groove wasnt right for a customer when they signed up, doesnt
mean that well never be right for them.

196

So we began testing winback emails at 7, 21 and 90 days after a user didnt convert.

90 Days Later

The 90-day email has converted at around 2%.


Thats not impressively high, and were still working on it, but thats 2% that
wouldnt be Groove customers right now otherwise.
Takeaway: Not every customer quits because they dislike your product. There
could very well come a time in the near future that youre both perfect for each
other, but youll never know unless you reach out to them.

How To Apply This To Your Business


As always, this is not a comprehensive guide; its simply a snapshot of whats
working for us right now.
And while what works for us may not necessarily work for you, hopefully you can
use what weve learned to learn about what approach would for your unique
customers.
To be sure, this is also not a "how we did it" success story. Our email sequence is
very much a work in progress, and we continue to run new tests and learn new
things every week.
But weve been amazed by what weve learned so far. And by applying some of
these tests to your own onboarding emails, my hope is that youll be amazed, too.
197

How Our Startup Hires Top Talent


Without Bidding Against Google
(PLUS, We're Hiring!)
April 10, 2014

I was frustrated when we lost a great


engineering prospect to Google. Here's
why that turned out to be a good thing.
"Im also considering an offer from Google."
As a startup founder working desperately to build his team, nothing scared me,
from a recruiting standpoint, more than hearing those words.
For good reason: Google is, well, Google. Theyve got insane offices with even
crazier perks. Theyve got names that would skyrocket the value of any resume.
And most importantly, theyve got infinitely deeper pockets than I do or ever will.
While I was offering salaries that were highly competitive in our market, there was
no way I could compete with what Google could offer top engineers.
And so, as that same prospect explained to me a week later, he would be taking
their higher offer.

198

Theyd beaten us. And I was terrified that theyd continue to beat us.
"I dont want to have to go up against Google," I complained to one of our advisors.
"I cant compete."
His response?
"You dont have to."
The conversation that followed completely changed the way we did recruiting,
and has allowed us to build a top-notch team that wants to be here, without
getting into bidding wars.

Looking for Employees Is Like


Looking for Customers
Working at a big tech company offers a lot of benefits.
Stability. Predictability. A wide array of corporate perks. And yes, big cash for top
talent.

Perks

We cant compete for the employees that are motivated by those things.

199

But as a startup, we can compete for employees looking for something different.
There are a lot of parallels to our quest for new customers. When we first started
out, we tried to compete against Zendesk and Desk on price. One of our primary
messages was that Groove was cheaper.
The problem with positioning on price is that it gets you exactly the type of
customer youre asking for: price shoppers.
Higher maintenance, far less loyal, and gone at the drop of a hat when a cheaper
option comes along.
Plus, if you try to compete for customers on price, a bigger player can always
lower their prices to bleed you out of business.
We learned that had to compete on other differentiators. Ones that actually made
people want to do business with us because we were the best choice for them, not
because we were the cheapest. We needed customers who were motivated by
more than price.
That same principle applies to hiring.
As a young startup, you cant compete on salary.
Even if you win, what happens when a more lucrative offer comes along? That
employee that chose you because you won a bidding war is gone.
But you can compete for the right employees (and customers) who are motivated
by something greater.
Takeaway: Competing for employees on salary will get you employees who are
most motivated by exactly that. Its a losing proposition in the long term, and a
game that startups cant afford to play.

Our Value Proposition


to Prospective Employees
Being on the ground floor of an early stage startup is a very unique thing.
And it takes a unique kind of person to thrive under those conditions, and to
prefer them over the alternative.
Our company is NOT right for many people. Probably for most people. And we try
to make that absolutely clear in our job postings.

200

But for the people who would excel here, we work really hard to make sure that
we convey that Groove is the perfect fit.
And after doing hundreds of interviews in the last year and testing a number of
approaches, I think Ive finally cracked the code for the three big differentiators
that help us qualify and attract the right people.
Note: these differentiators arent necessarily unique to Groove. Lots of startups
have them.
But most big companies dont. And thats what the most important part of finally
succeeding in building a great team was: Figuring out how to get into the right
talent pool.

1) Impact
When youre small, every customer support interaction can have a big impact on
the business.
If the customer comes away absolutely thrilled with your support, theyll not only
stay with you, but theyll refer their friends.

Happy Customers Tell Their Friends

If the customer comes away disappointed, you may have lost another chunk of
revenue that you cant afford to lose, along with the referrals you wont get now.
The same goes for every line of code and every blog post.
This is the case at almost every startup. and its resonated with every team
member Ive hired. Yet I see the point being made in very few startup job
descriptions.

2) Autonomy and Remote Work


Most people cant work remotely for a startup.
Most of us are simply too conditioned to working at an office, and the chaos of

201

startup life mixed with being thrown into the deep end of remote work is simply
too much.
Weve found that here at Groove a few times with new hires.
Sometimes, weve been able to fix it and help the employee adjust.
Other times, weve failed.
But weve been very fortunate to build a team of very productive, very organized
and very close-knit remote workers.
If you want to succeed as a distributed team, theres no other option.
Weve done that by finding people with the right experience: those who have
worked from home and at startups (or as freelancers).
And we arm them with the best tools weve been able to find so far:
HipChat and ScreenHero for staying in constant touch with one another.
Pivotal Tracker and Trello for keeping on top of our daily tasks.
Google Drive to share and collaborate on content and long-term plans.
Being part of a remote team is one of the most appreciated benefits of working
here.

3) Culture and Values


We dont have a culture deck, or a Groove manifesto.
We simply havent gotten there yet.
But we do have the culture and values of our team radiating from every corner of
our business.
On the outside, this blog is the biggest example of that. Simply reading these posts
can give most people a fantastic idea of whether theyd fit in here or not.
And, since weve launched the blog and continued to hire, every single person
weve hired has been a reader of this blog.
Perhaps its bias on our part, but i think its powerful self-selection on the
applicants side, too.
Internally, one only need to spend a day in one of our HipChat rooms to get a feel
for the dynamic of our team.

202

An Average Hipchat Afternoon

And thats why we do trial periods for new hires before they become full time
employees.
Both parties learn very quickly if its a good fit.
Takeaway: Every company can offer something different and unique to its
employees. Figure out what your differentiators are, and focus on them
aggressively.

How to Apply This to Your Startup


Please dont read this as an excuse for paying low wages.
Its really important to me to invest in competitive salaries for top talent.
It keeps the business secure by keeping our employees feeling appreciated.
And frankly, its the right thing to do.
But getting into bidding wars with Google is on a whole other level that goes far
beyond market rates.

203

We cant play in that sandbox, so weve had to look for other ways to set ourselves
apart for talented applicants.
The above are just a few of the most effective ways weve found to do that.
The best advice I can give is to focus on what makes you different, and be very
clear about it.
Youll close the door to a lot of potential applicants, but youll appeal strongly to
the right ones. And thats far more important and valuable to your business in the
long term.

204

What I Did When I Couldn't Find a


Technical Co-Founder
April 17, 2014

Without a developer, Groove would never


get built. Heres how I took the first step
to turning my idea into a business.
I had nothing.
No prototype. No customers. And certainly no funding.
Sure, my last company was recently acquired, and that gave me a little leverage.
And I was ready and willing to put my own money on the line.
But why would any seasoned, skilled developer worth his salt join me with no
reason to believe that we would succeed?
The weeks were flying by, and my search for a technical co-founder was going
nowhere.
If I ever wanted to get my crazy idea off of the ground, Id have to look at other
options.
Now, a lot of smart people disagree vehemently about whether startups need
technical co-founders early on.
205

Mark Suster believes that If you dont have somebody inside your organization who
is setting the technology direction then Im convinced youll never head for
greatness.
Drew Houston acknowledges how tough it is to find a technical co-founder, and
suggests learning to code or outsourcing the job.
Unlike taking on a co-founder or hiring a freelance developer, working with an
agency is not an alternative that a lot of founders consider.
And frankly, I think Mark is right.
If I had found the right technical co-founder with the right chops at the right
price and for the right piece of equity, Id be telling a different story now.
But I didnt, and Im not.
If I wanted to get Groove off the ground quickly, I had to get creative. I decided to
begin a search for a development firm to build the first iteration of Groove.
I looked at dozens of agencies without finding the right fit. Nobody really made
me feel like they got what I was trying to do.
And then, in a chance encounter, I stumbled on MojoTech, an up-and-coming rails
shop in my home state of Rhode Island.
That introduction set into motion the events that would finally turn my idea for
Groove into the app our customers use today.
Note: Groove isnt getting anything for mentioning MojoTech in this post. My goal
is to tell a balanced story of my decision to hire an agency, and the results of that
decision, in the hopes that it helps others who are going through the same
struggle.

Making the call


For days, I waffled back and forth on what my next move should be.
I weighed the potential pros and cons.
Working with an agency would be expensive. Really expensive. Likely around three
times more expensive than hiring a developer myself.
But, my search for a technical co-founder was getting me nowhere, and this way
Id at least be guaranteed a product sooner rather than later.
206

I also had my doubts when it came to trust. With an agency that had to bill me to
keep their own lights on, would our interests truly be aligned? Would they be as
motivated to work fast as I am, or as a co-founder with skin in the game would be?
Of course, if I hired an agency, I wouldnt need to recruit a team yet. It would let
me focus on working side-by-side with them on getting the product built, rather
than many of the other tasks that normally come with building a business.
Then there was the issue of ownership. By outsourcing development, Id keep
100% of the company. This was good.
On the other hand, this also meant that every decision stopped with me. There
wouldnt be the checks-and-balances system that comes with having a partner
with a different and in many cases, more relevant perspective.

Decisions, Decisions

Ultimately, there were two major factors that led me to pull the trigger on signing
with the Mojo:
First, I was, by background, a product manager. I felt comfortable with the tools
and processes that they used, and I felt confident in my own ability to navigate
and evaluate the path wed be going down together.
And second, as I rewrote my pros-and-cons list for the sixth or seventh time, I had
a sobering realization

207

Four months from now, I could have a living, breathing product in the market that
would let me collect user feedback, get validation and push this business forward. Or,
I could still potentially be sitting here with nothing.
I signed the contract that afternoon.
Takeaway: Its always easier to not make a decision than it is to make one.
Unfortunately, no business ever got built on indecision. Simply choosing a path
and taking it even if its not the optimal choice is always better than being
paralyzed by the process of choosing.

Working Together
In the months that followed, I worked closely with the 4-person team that they
assigned to Groove.
During that time, I was in HipChat with them every single day.
We worked as a team, and we had a teaser site and a beta app completed in about
four months.

Four Months Later

Getting to that point was all I needed to test my assumption that there was
demand for a simple alternative to Zendesk.
We launched the trial, The Next Web quickly ran a post about us, and a week later
we had 1,000+ private beta signups.

208

Now I had the leverage I was missing early on.


I had prospective customers. Validation in the press. Calls from potential
investors.
In short, I had something to build from.
I worked with MojoTech on a few further iterations of the Groove app and
marketing site while I began to recruit Grooves first employees.
And a few months later, after I had hired two developers of my own, we parted
ways with a handshake.
As I think about the work we did together, there are a number of takeaways both
positive and negative that Id urge any founder in a similar position to consider:

The Good
I had an app
The most important consideration of all. Four months after we got started, I had a
working app that we released into the market. We were able to collect feedback,
test the product, learn about our users and improve.
Had I not hired MojoTech, I have no idea how long it would have been before the
app was built.
I had a lot of work done for me
I didnt have to recruit. I didnt have to train any employees. And while I worked
very closely with the MojoTech team, I didnt have to manage anyone directly; I
could focus on what was most important to me: contributing directly to the
creation of the product.
I had leverage
With the app built, the users signed up and the TNW story published, I had what I
needed to not only begin building a team of my own, but I could look for investors
to help me continue building the company, and I had more than just an idea to
show them. While raising money is never easy, the validation did give me a bit of
leverage which helped to convince investors that Groove would be a reasonable
bet.
Soon after we released the beta app, I raised $700,000 from a small group of angel
investors. This gave us the boost we needed to start building a team.
209

I had accountability
Before investing $300,000 on working with MojoTech, Groove lived in my head
and in a few documents on my computer. I showed it off to potential partners at
coffee shops, and never really made any tangible progress. Committing to having
the app built gave me accountability; stalling was no longer an option. The money
was spent and the die was cast, I had to begin working on the business.

The Bad
It was not cheap
As I mentioned above, I could have done quite a lot with the money I invested in
working with MojoTech. I could have hired my own developers from the start.
Whether or not the result would have been the same, I have no idea, but the cost
is not inconsiderable, and for many people, impossible.
I still wish I had a co-founder from the start
I dont have a co-founder to help with major decisions, or even minor ones. Many
prospective investors and partners didnt take me seriously without a technical
co-founder. Being a single founder (without the emotional support of someone
sharing your journey) is lonely to an extent that has real business implications; Ill
share more on that in an upcoming post.
I absolutely love what I do every day, but that doesnt mean it never sucks.
I didnt always love the agency approach
As an entrepreneur, Ive always wanted to build the quickest and dirtiest version of
our vision that we could, get it into the market and start testing and iterating.
The structured process of working with an agency the branding exercises, the
competitive matrix mapping, the seemingly huge amount of attention and time
given to every little aesthetic detail was hard to swallow for me. While Groove
has benefited massively since weve begun taking a research-driven approach to
growth (see the entire history of this blog for examples), I dont know that Id take
such a structured approach so early on again.
There are legacy challenges to team-building
There isnt a single developer on our team who was there for our first line of code.
Thats a huge challenge. Not only does it sometimes take longer to find bugs and
fix problems, but its a morale issue, too. I would have loved for our team to feel
the ownership of the product that comes with having built it from day one.
210

Should You Hire A Development


Agency To Build Your App?
This post is for the dozens of founders and would-be founder whove emailed and
commented asking for advice about getting their product off of the ground.
Will hiring an agency work for you?
Honestly, I dont know.
It worked for me. I hired MojoTech, they built the early versions of Groove, and
after an insane amount of hustle, hard-fought wins and near-death experiences,
were here. Were not yet where we want to be, but were here.
Would we have been here if I had continued to hunt for a technical co-founder?
I guess Ill never know.
But I hope that by sharing my own experiences, I can help you make your decision
a little bit easier.
The choice will never be clear, and the conditions will never be perfect.
But the most important thing you can do, no matter which approach you take, is
start.

211

Lessons Learned Growing our Startup


to $50,000 in Monthly Revenue
April 24, 2014

Its been seven months since weve


officially started documenting our journey
to $100k. Heres where we stand today
My cursor hovered over the publish button for what seemed like hours.
What the hell am I doing?
An email notification popped up in the corner of my screen.
A distraction!
Ill post this later, that email is probably important.
Half an hour later of sending emails, calling our developers, and doing whatever
else I could to put this off, I was back on the publish button.
This could be a really bad idea. What if people hate it?
I struggled with myself.
Ah, another email. Ill just go check that out.
212

I played that game for four more hours.


To be honest, it didnt really matter.
The die had been cast.
I had already shared the post with almost 100 people. And they were expecting me
to publish it.
I was just nervous.
Up until then, Groove had been pretty much out of the public eye, aside from a
blip on the radar when The Next Web wrote about us.
If this effort was as successful as wed hoped it would be, things would be very
different.
But if it flopped, Id look like a complete idiot to 100 brilliant, successful
entrepreneurs.
Finally, I gave up.
Whatever. Lets do this.
*Click*
The first post in our Journey To $100K blog was live.
I didnt fully appreciate it at the time, but it marked a totally new direction for
Groove.
But it also marked the start of something much, much bigger: the amazing
community of startup and small business founders and employees that come to
this blog every single week to learn and share their own experiences.
And almost every week, someone emails or leaves a comment asking me to post an
update when we reach the halfway point in our journey.
This is that update.

213

The 7 Big Wins


1) A New Approach
About six months ago, we had a massive, fundamental shift in the way we saw our
business.
In the past, our decisions had been driven by the ultimate question: how can we
succeed?
And while that approach got us to a decent starting point, eventually things began
to slow.
We tried to test and tune every aspect of Groove: our site, our product, our brand,
our emails, our blog. Everything.
And through that process, we did hundreds of hours of research.
Surveys, one-on-one conversations, digging deep into our metrics.
One of the most enlightening things we learned was that when our customers
succeeded, so did we.
It sounds so ridiculously obvious and almost trite, but it was something wed never
truly been confronted with before. We shouldnt have been surprised by it, but it
was a revelation.
When our blog readers succeed at business because of the lessons we share, many
of them become trial users.
When our trial users succeed at making their whole team better at support, many
of them become customers.
And when our customers succeed at making their customers happy time and time
again, and growing their business because of it, Groove succeeds.
We realized that our success has very little to do with getting people to pay us
money, and everything to do with delivering so much value that paying us
becomes the easy choice.
This approach informed and continues to inform everything:
Our successful marketing site redesign that doubled conversions
Our email onboarding optimization that increased trial-to-customer
conversions by 10% or more.
Our blog overhaul that got us 5,000+ subscribers in five weeks.
214

215

Takeaway: Your prospects care very little about your business. They care about
themselves, and their own problems; we all do. Rather than thinking about how to
benefit your business, think about how to benefit your customer, and the revenue
will follow.

2) Committing To And Investing In Data


That research I mentioned above?
It would have never been possible without the right tools.
Sure, a lot of it was done by hand: emails, Skype, phone calls.
The data we got from those sources was unquestionably valuable. It led to huge
changes in positioning and strategy, including the decision to improve our
communication about product updates.
But a big part of the data we collect comes from the apps we use to track our
business.
Apps like:
KISSmetrics for deep insights into our visitors and customers.

KISSmetrics

216

Crazy Egg for helping us understanding where our site was failing.

Crazy Egg

Campaign Monitor for super-valuable analytics on our email sends.

Campaign Monitor

217

Qualaroo for breakthrough lessons about why visitors werent converting.

Qualaroo

I talk to a lot of entrepreneurs who think that some of these apps are too
expensive.
They say things like when we get big enough, well pay for it.
We wouldnt have gotten big enough without paying for it. These apps have paid
for themselves many times over.
But its important to understand that apps arent everything, and neither is the
one-on-one data collection. The two need to work in concert.
The way we see data at Groove is pretty simple: tools can tell us what is
happening. Its up to us to figure out why.
Takeaway: Research isnt sexy, and it isnt easy. But its the only way to get the
deep understanding of your audience and customers that will put you ahead of
your competitors.

218

3) Inbound Marketing
One of the most common questions we get is where do you find customers?
And the answer is right here.
Literally.
This blog, the community around it, and our efforts to publish content thats
hugely valuable to readers every single week have all had a massive impact on
Grooves growth.
Its come a long way since we first envisioned building a resource for
entrepreneurs that I wish had existed when I started my first business.
We read everything we could get our hands on, talked to anyone who would listen
and worked hard to build a network of influencers that would help us get 1,000
subscribers in less than 24 hours after we published our first post.
This blog is our brand.
Without it, I have no doubt that we would not have reached this milestone.
Its our biggest source of leads by a huge margin.
And the best part? Unlike an ad, a good blog post pays off forever.
We get hundreds of visitors each day from people stumbling upon blog posts that
are several months old.
That evergreen traffic benefit has helped us go from a $30,000/month business
with very little online footprint to a $50,000/month business that ranks on the
front page of Google for many of the topics we write about.
If we had started blogging earlier, we would have reached $30,000 a lot faster.
And its not just subscribers and search traffic that comes from publishing this
blog. Weve gotten tens of thousands of visitors from our posts appearing on the
front page of Hacker News, and from the bit of guest blogging weve done on the
Shopify and KISSmetrics blogs.
The latter is an effort we plan to double down on (in fact, we had a guest post
published on the Buffer blog yesterday) and explore much further.

219

Long-Term SEO Benefits

Takeaway: If youre not blogging, you need to start yesterday. But blogging for
bloggings sake isnt enough. Find a specific, unique angle to deliver value to your
readers, and do it better than anyone else. Youll be rewarded forever.

4) Improving The Customer Experience


The bigger and faster we grew, the more bugs and product issues we had.
Its not that the product was getting worse. Its just that with more customers,
people were finding edge case bugs that hurt the customer experience for a
limited group of users.
But as you grow, so do those limited groups of users.
And while one of the challenges of scaling is that we spend more developer
resources fixing those new bugs than we do on building the product, we still never
stop tuning and tweaking our app.

220

Reaching Product/Market Fit is not an excuse to stop building.


And while Groove hasnt changed that much since that milestone, the features
weve added have helped us grow.
For example, our HipChat integration, built in response to big demand from our
own users, has opened the door to a massive new audience of HipChat users who
now know about Groove.
Beyond actual product enhancements, weve been able to improve the customer
experience by making everything around the product better.
Through better email onboarding, we helped customers get productive faster.
Through more proactive support, weve made customers feel comfortable that
were here for them, and weve made it more likely that theyll reach out with any
problems.
And through behaviorally-triggered emails, weve been able to spot at-risk
customers before they quit, and help them get back on track.

Behavioral Emails

Takeaway: Product development never stops. Even if youve reached


Product/Market Fit, there will always be more you can do to make customers fall
deeper in love with your product.

221

5) Not Being Afraid To Break Stuff


If all we did for marketing was blog, we might have reached the $50,000 milestone.
It wouldnt have been now.
It might have been in a year or two.
But maybe we wouldve gotten here.
The truth is, weve tried dozens of new strategies and tactics to deliver more value
to people.
Some of them worked:
Introducing the Customer Support Academy has helped both customers and noncustomers get better at support, and has led to traffic, referrals and signups for
Groove.

Groove Support Academy

Running the SaaS Small Business Conversion Survey let us help the community in
a unique way, and also gave us a lot of lessons to share about successfully
deploying surveys.

222

Putting together the Small Business Stack was a huge win for us; we helped
thousands of startups and small businesses get access to software they might not
have been able to afford otherwise, and weve given valuable exposure to dozens
of really useful SaaS companies.

The Small Business Stack

Adding Powered By Groove to the customer satisfaction ratings page. Unlike the
Powered by link in our support widget, this one reaches prospects after theyve
already received awesome support, so theyre far more likely to want to learn
more about Groove.
Some of them didnt work:
Offering discounts for Groove attracted the wrong kinds of customers, devalued
our brand and cost us a lot of money
Tiered pricing confused visitors, turned people away and completely went against
the simplicity we were trying to achieve.
223

Powered By Groove

Tiered Pricing

224

The wins were big breakthroughs for us, but the failures were, too. We learned
really valuable lessons when we did end up making the wrong decision, and were
a stronger company for it today.
And if we were afraid to try new approaches because of the risk of failure, we
wouldve coasted (or worse, stagnated), and never found the big wins that have
helped us reach this milestone.
Takeaway: Dont be scared to try new things. Even if they fail, they probably wont
do nearly the damage your worst nightmares suggest they will. And no matter
what, youll learn from the process.

6) An Obsessive Focus On Support


As Paul Graham says, weve had to do a lot of things that dont scale.
The most important of those things is support.
Of course, we use our own tool to make things easier, but delivering the best
support possible will always require a human.
And delivering the best support possible was a big part of what got us to $30K,
and now to $50K a month.
Its not something were willing to compromise on.

The ROI of Support

225

Every customer gets the same personal attention now as they did when we were
in beta.
In fact, they get more.
There are parts of the experience that weve been able to automate (like email
onboarding), but we still offer a human touch to every customer that signs up.
And its certainly helped us grow.
Takeaway: If something made you special to your customers when you were just
starting out, do everything you can to never compromise that differentiator. Even
if it means doing things that dont scale.

7) Focusing On Big Wins


Notice how few of the wins above are tactical.
No a/b tests of button colors.
No swapping icons or images.
No playing with email send times.
Weve done those things. And weve gotten some results from them.
But theyre not the big wins.
Maybe one day well be big enough where changing our button color makes a
material impact on our bottom line.
But for now, our big wins the ones that actually push the business forward
have come from big changes.
Changes in perspective, messaging, positioning. In the way we offered our
product. In the way we understood our customers.
Thats where the breakthroughs have come from.
The 100%, 200%, 300%+ increases in conversion rates and engagement.
The jump from $0 a month to $30,000 a month to $50,000 a month.
Takeaway: Tactics are great, but strategy is where the big wins are for most
startups and small businesses. Little tests can generate results, too, but big
business-changing breakthroughs come from big business-changing tests.

226

The Next $50,000


Theres no question about it, Groove has come a long way since we started this
blog.
Were a more successful company, sure. But were also a better company.
Theres still a whole lot more to be done. Were going to be exploring and testing:
Referral programs
SEO
Retargeting
More Guest blogging
Community building
Education
More partnerships and integrations
And much, much more.
And well keep working on the product, and on support, and on making our
customer experience the very best.
Over the last six months, weve focused on completely relaying the foundation of
our business, and re-engineering our strategy.
Its paid off, but what worked for us wont necessarily work for you.
And what didnt work for us might be your breakthrough.
But I hope that above all, by sharing our experiences, we can convey how
important it is to always be looking for big wins in your business.
Those big wins might lie behind a tiny a/b test on your landing page.
But they probably dont.
When we study whats happening, do the hard work to dig into why its happening,
and then test big changes, we make huge leaps in our growth.
And I hope you will, too.

227

The Pros & Cons of Being a


Remote Team (& How We Do It)
May 1, 2014

Working remotely has a lot of


advantages, but its far from perfect.
Heres what weve learned in our journey
as a remote team.
Headphones.
They were practically all I could see.
An ocean of big, round, silver headphones attached to silent, focused faces that
hadnt said a word all day.
When my last company grew big enough, we did what startups in New York were
supposed to do.
We rented a big, trendy SoHo loft to give our team a headquarters.
It was a wide open floor plan that gave everyone the opportunity to talk to one
another and collaborate seamlessly.
It was an opportunity that few actually took.

228

At around 9AM, employees would wander into the office, pour themselves a cup of
coffee, sit down at their desks, put on those big silver headphones and get to
work.
And theyd stay in that position for the whole day.

Headphone City

We were productive, and we got along really well, but anyone looking at the scene
above would see an army of headphones getting little benefit from sharing a
physical space.
When I started Groove, I decided to go in a different direction.
To forsake the office and build a remote team.
I still wonder if it was the best decision, but regardless, its the one I made.
Many months later, Ive learned a lot about remote work.
About working from a home office, managing a remote team and building a
business where the employees hardly ever see one another.

229

Below are some of the most important lessons Ive learned.


If your team is already a well-tuned distributed machine, youll already know
about most or all of these lessons, because like us, youve learned them the hard
way.
But if youre at the same crossroads I was at in choosing which direction to go, or
if youre looking for tips on being a more efficient, cohesive and productive
remote team, then this post is for you.

The Good: Pros of Running a Remote Team


1) We have access to more and better talent, faster.
When it was time to start hiring, I tried to contain my initial push for developers
to the area surrounding Newport.

Asking for referrals

Unfortunately, I couldnt find anyone with the skills, experience and intangibles
that I was looking for.
As soon as I opened up my search to include the rest of the country, I found the
right employees very quickly.
Our first two engineering hires were made within the next few weeks, and theyre
still with Groove today.
We now have team members in Rhode Island, Maryland, North Carolina, Colorado,
Utah and Illinois, with part-time help from Bulgaria, Russia and a few other parts
of the world, depending on what were working on.
230

And averaging one to three weeks, the searches for those team members were
relatively short compared to the six-week-or-more recruiting campaigns wed
undergo to hire a single employee at my last startup.

2) Our employees have lives outside of work.


Yes, weve struggled with burnout in the past (though we no longer do).
But our team is happy, and one of the things we all appreciate is the freedom to
spend time doing the things that are important to us beyond our jobs.
We have a 15-minute team call every Monday morning that everyone attends.
Thats when we make sure that were all on the same page about accomplishments
from the previous week, and goals, deliverables and challenges for the coming
week.
Of course, theres a ton of collaboration that happens outside of that weekly call,
but thats our only scheduled meeting.
Aside from that, our team works when and where they want to. And we all have
other commitments.
Most of us are married or in serious relationships.
Two of our team members have babies (read: second full-time jobs).
Another is engaged to a nurse whose schedule changes every week. Their lives are
made a lot easier by the fact that hes able to work the same hours as her
(sometimes, that means early mornings, evenings or weekends) and get time off
when she does (usually weekdays).
Personally, I love living next to the ocean. On more than one occasion, Ive
stopped what I was doing, grabbed my board and headed out for some mid-day
surfing.

231

Would all of these things be possible if we worked in an office?


Sure, there are a lot of people who make it work.
But not spending two hours per day commuting, and having the flexibility to work
when you prefer sure does make it easier.

3) We can respond to "oh shit" situations faster.


When our server disaster hit, we were definitely caught off guard.
But being a remote team helped us restore service when we did, and not hours
later.
When we learned of the issue, we didnt have to waste time waiting for our team
to assemble at the office.
Everyone had everything that they needed to get to work right away.
Sure, with VPNs, practically anyone can work from anywhere if the shit hits the
fan.
But if youre accustomed to working together in an office, working remotely is a
workflow disruption to your team on top of an already high-stress crisis.
We were lucky that, as far as collaboration goes, things were business as usual and
we were able to move quickly and without interruption.

4) Our overhead is lower.


Office space isnt cheap.
Neither is furniture, or electricity, or business-level internet access (at least here
in the US).
The costs of running a virtual team are minimal in comparison. Our "office"
expenses are subscriptions for the SaaS tools we use to function:
HipChat for constant communication: $14/month.
Screenhero for screen sharing and VoIP: free (for now).
Skype for customer demos and calls: $30/month for a few premium
accounts.
Google Drive for collaborating and sharing files: free.
15five for staying on top of our teams happiness and challenges: $49/month.
Pivotal Tracker and Trello for project management: $23/month (though we
would certainly use these from an office, too).
Every dollar we save on rent is a dollar we can reinvest in the growth of the
business and our employees.

232

The Bad: Cons Of Running a Remote Team


1) A great startup employee doesnt necessarily make a great remote
startup employee.
While the talent pool certainly gets bigger when youre hiring from around the
world, your hiring needs also change drastically.
We cant just hire good startup employees, because weve found that that simply
isnt enough.
Most people dont have the organization, focus and motivation to be productive
working remotely.
Its not that they cant. Its just that they havent had to.
Successfully working from home is a skill, just like programming, designing or
writing. It takes time and commitment to develop that skill, and the traditional
office culture doesnt give us any reason to do that.
We had some early hires very talented people not work out, only because they
had never worked remotely before and we were unsuccessful at helping them
develop that skill.
Now, we dont just look for good startup employees, but we look for good startup
employees with experience working remotely.
Everyone on our team has either worked on a distributed team before, or been a
freelancer or entrepreneur in the past.

2) Company culture takes a hit.


Theres a lot more to startup culture than having an office. At the end of the day,
culture is about shared values and goals.
But having everyone in one place makes it a lot easier to build that culture.
The more exposure team members have to each other, the more developed and
defined that culture becomes.
Simply by virtue of being remote, that exposure is necessarily limited.
Weve done a pretty good job at working on culture through close contact in
HipChat, team culture exercises and ensuring that new employees are a good fit
through trial periods before we hire.

233

An Average Hipchat Afternoon

But its still, and I suspect always will be, a challenge.

3) Communication gets harder.


With team members in different time zones and on different schedules, there are
very few times when everyone is available.
Most of the time, this isnt an issue.
Outside of our weekly call, our team primarily uses HipChat to talk, as it keeps
everything in one place and saves chat messages for when a user gets back online.
But sometimes, you need an answer now.
Maybe a customer needs an urgent fix and the developer you need is coding away
in full-screen.
Maybe theres a question about a blog post that needs to go out today, but the only
person who can answer it is three time zones away and wont be up for another
two hours.
234

In an office, if someone isnt responding to an email, its easy enough to stop by


their desk and get what you need.
On a distributed team, thats not really possible.
Of course, in a truly urgent situation, we wont hesitate to call.
But for everything else, it means we have to be organized and diligent about
tracking what we need from each other. And if getting that information or
deliverable is an obstacle, we need to be able to switch tasks until we can get it.
Its not the most efficient system.
While I think theres a net positive impact on productivity from working remote,
the communication barrier can, and sometimes does throw a wrench in the gears.

4) Its (practically) impossible to transition to an office.


At this point, whether or not I was wrong about going the remote route doesnt
really matter.
Switching to an office-based team would mean either a) moving everyone to one
place, or b) laying off the team and starting over.
We have an amazing team, and theyve got deep roots all over the place.
Neither of those options are on the table now, nor will they ever be.
So in the practical sense, the fact that we cant switch isnt a challenge, since its
not happening.
But its a challenge in that I always wonder whether it was the right move.
Would we have grown faster if our team was in one place?
Would we have been taken more seriously by press and potential business
partners?
Would we have been more productive and efficient by working elbow-to-elbow?
Well never know.

Weve Still Got (Remote) Work To Do


Although weve tackled a lot of the hardest challenges of working as a remote
team, and reaped many big rewards from it, Id hesitate to call us a remote success
story yet.

235

Weve still got work to do, and much of that revolves around developing and
protecting our culture and collaboration as we grow.
Some of the ways were going to be doing that include:
Retreats to bring the whole team together in person (its crazy to me that Ive
never actually met a couple of the people I work with).
More defined systems for onboarding new employees to our remote "office."
Hiring employees in more time zones to improve our support coverage and
development cycle.
I hope that our experiences help you make up your own mind about whether
remote is the right way to go for your business, and if youre a remote team, I
hope youve learned something new.
This is an important topic to Groove, and well keep writing about it as we learn
new things and grow our team.
But first, Im going surfing.

236

8 Things Every Non-Technical


Founder Should Know How to Do
May 8, 2014

Ive founded three SaaS startups, all


without writing a single line of code.
Heres what I wish I knew from the start
Sorry, but until theres a programmer on the founding team, this discussion cant
move forward.
Trying to raise money as a non-technical founder was an uphill battle.
One where I kept getting pushed back with politely-worded attacks of you dont
have what it takes.
Thanks for the vote of confidence, guys.
Even though I had a product, I wasnt a developer. And despite my efforts, I didnt
have a technical co-founder, either.
In the technical world, non-technical founders risk being seen as unqualified.
Ive seen the attitude from potential investors, employees, partners, advisors and
even fellow founders who have no stake in the business.

237

You cant build a software business if you cant make software.


Bullshit.
While weve got a long way to go, Im damn proud of how far weve come at
Groove.
And weve done it with an outsourced prototype, a killer team and a ton of hustle.
And me. A decidedly non-technical founder.
This isnt a woe-is-me cry for non-technical founders to get more respect in the
industry. Respect is earned, and there are a lot of groups far more maligned.
But this is now the third time Ive been a non-technical founder, and Ive learned a
lot of lessons along the way.
Lessons that have helped me work more effectively with my technical team
members, add more value to our product and become a better entrepreneur.
I hope you can learn from them.
Note: a lot of these are great skills for technical founders to have, too. And many
technical founders I know are really good at them.
But from my experience, for us non-technical folks who cant contribute to the
codebase, Ive found these to be absolutely critical.

The Skills That Have Helped Me Succeed as a


Non-Technical Founder
1) Research and Validation
Before my first startup, I started my career as an assistant to my brother, a
financial advisor.
Soon after that, I began to get frustrated that there was nothing out there to help
us automate the customer management side of things.
Everything followups, lead nurturing, tracking was manual.
I thought that maybe if I was having this problem, then others might be, too.
So I put a PowerPoint deck together about the solution I envisioned a CRM for
financial advisors and then I picked up the phone.

238

Circa 2004

I called other financial advisors in my area, asking if I could have five minutes of
their time.
Then I asked them about their own experiences and pains, and learned that
dozens of them shared the same burning frustrations that we did.
It was then and only then that I decided to team up with my technical
cofounder and get the product built.
Its a process Ive repeated for all of my startups, and the time I put in early on has
paid off exponentially in building a better solution than we otherwise would have.
Takeaway: Without the ability to hack together a prototype, the easiest way to
validate your idea is simply to go talk to your potential customers first. Youll be
amazed at how many people are happily willing to share their time and opinions
with you.

2) Building Visuals
I was lucky to team up with one of my best friend developers who had just left
Yahoo! and agreed to join me.
Before he got started, I tried to sit him down and explain all of the features and
functionality I imagined our app would have.

239

After about five rambling minutes, he stopped me.


We cant build from a list, he explained. Lets organize your thoughts and map
this out so that we know what itll look like first.
And so I did.
I started to draw sketches. And then those turned into wireframes. And finally, I
learned how to use Photoshop and built mockups of the app.
It bridged the gap between the thoughts in my head and my cofounders
understanding of them, which meant that we saved a lot of time on changes and
iterations early on.
And while these days Ive ditched Photoshop and switched to Balsamiq for
mockups, its still my favorite way to show our team exactly what we need to do.
For example, I might point to a part of the site that needs fixing:

Fixing Typos

Or I wireframe up a whole page to make it easier for the team to understand my


vision for it:

240

Wireframe

Or, if theres a user experience issue, Ill record the behavior using Jing, a motion
screen-capture tool, and send it that way:

241

Screen-Capture in Action

These are much more helpful to our team than a description could ever be.
Takeaway: Wherever youre able, showing is better than telling. Pick good tools for
mockups and screen captures, and use them to show your team what you want.

3) Giving Bulletproof Feedback


When you do tell instead of show, learn to tell as descriptively as possible.
Early on at my second startup, we were trying to build a login page for our
customers, and it was goingpoorly.
The form needs to be bigger, and we need fewer navigation links, I emailed our
development lead.
If you have product development experience, youre shaking your head in disgust
right now.
No problem, hed say. And an hour later, Id get a new version with a too-big form
box and critical links missing from the header.
We had been dancing this dance for days; me flat-footedly asking for vague
changes, and him dutifully matching my steps.
Finally, I was fed up.

242

Why on earth would we remove the link to the home page?, I quizzed him.
Um, you were the one who told me you wanted fewer links.
And so I was.
That afternoon, we had a long discussion that was incredibly helpful for me.
I learned the importance of giving clear, thorough feedback.
After all, if someone sent a blog post back to me with the comment needs to be
shorter, Id be just as lost.
Now, instead of fewer navigation links, I might say lets remove the About,
Contact and Features links, and increase the size of the form submit button by
20%.
Things move a whole lot smoother.
Takeaway: Theres no excuse to give vague feedback. It slows down your team,
creates confusion and hurts your product. Be clear, concise and direct.

4) Pre-Selling
At that first startup, while my friend sat coding, I, again, hit the phones.
I called more than 1,000 financial advisors around the country, and just as I did in
our earlier stages, asked them about their frustrations.
And while I was able to get some amazing insights that helped us in our
development, I also got something that massively increased our chances of
success once we launched.
In those conversations, after hearing about how much the agent hated doing their
follow-ups by hand, Id say something along the lines of:
Just so you know, were building a tool to automate all of that. Itll do [X, Y and Z].
When its ready, Id love to show it to you and get your feedback. Would that be
alright?
That effort got us a list of hundreds of highly qualified leads, and dozens of paying
customers within weeks of our launch.
Takeaway: You can be selling even before you have anything to sell. In fact, while
your product is being built, thats one of the best uses of your time.

243

5) Selling
Ive found that my job as a non-technical founder, more than anything, has been to
sell.
Want to raise money? You need to connect with investors who see hundreds of
pitches each week and make the case that your company is worth betting on.
Want to sell your product? You need to connect with your customers and deeply
understand their challenges, hopes and fears.
Want to hire the best? You need to connect with talented prospects from a variety
of backgrounds, understand their goals and show them why your company is the
best fit for them.
Want to secure a profitable partnership? You need to connect with the person
youre exploring the deal with, know what theyre looking for and convey how you
can help.
Want to manage effectively? You need to connect with your team and stay on top
of a number of markers: happiness, productivity, obstacles, goals and schedules.
The list goes on and on.
Selling is a skill that can absolutely be learned. A couple of my favorite books that
helped me do just that are Neil Rackhams SPIN Selling and Yes! by Noah
Goldstein, Steve J. Martin and Robert Cialdini.
But beyond studying, the most important thing is to practice. Early on, every day
you spend selling gets easier than the day before.
As Ive learned from my own experiences, and from talking to people who are
much better at sales than I am, youll always run into new challenges and
frustrations. But over time, you get much better at dealing with them, and the
process becomes a whole lot easier.
And as a non-technical founder, its where the bulk of your value to the company
will come from as you grow.
Takeaway: The biggest job of a non-technical founder is to grow the business
through customer acquisition, hiring, managing and more. Get very good at
connecting with people; its a skill that can be learned through practice.

6) Cheerleading
In each of my three startups, Ive come up against people telling me that I have no
shot because Im not a developer.
244

Frankly, naysayers are a challenge that every founder deals with.


But they always sting the most when they harp on the things you know are true;
like the fact that you cant code.
Ive had to learn to be my own cheerleader. To motivate myself to push through
those fights and focus on what matters.
And through that, Ive learned to be a cheerleader for everyone else.
When our developers are focused on a nasty issue thats holding back the
company, theres not a whole lot I can do to help on the technical side of things.
But thats when I can be a cheerleader for our customers, helping them get
through the problem with constant communication.

Cheerleading For Customers

And for our team, sharing every win I can to boost morale and keep everyone
happy and motivated.

245

Cheerleading For Our Team

As the one who cant dive into the server and fix things, its the biggest
contribution I can make.
Takeaway: Its your job to be a cheerleader for yourself, your team and your
customers. Itll keep you sane, your team motivated, and your customers happy
and loyal.

7) Knowing the Tools of the Trade.


Like everyone else, developers use tools to help them do their jobs better and
easier.
To avoid disrupting peoples workflows and stalling the development of product,
Ive had to learn how to use those tools.
Every team will use different tools, but no matter what your team prefers, being
familiar with those developer tools can help the whole team.
When I find a bug, I dont send a productivity-crushing email for each little issue. I
write a descriptive user story and put it in Pivotal Tracker, which puts my
feedback seamlessly into the development teams existing workflow.

User Stories

246

Most of the tools out there dont take very long to learn (for example, Pivotal
Tracker has great, easy-to-understand video tutorials), but its an effort that will
contribute massively to the success of your team.
Takeaway: Dont try to bring your development team into the tools that you use.
Those probably arent built for development. Instead, streamline the process and
make life easier for your team by learning their tools.

8) Doing Everything Else


Ive had to learn to wear hundreds of hats.
Do we need to build a spreadsheet and find contact information for blog
engagement?
Thats my job.
Do we need to research and pick an app for screenshare product demos?
Im on it.
Does a developer need me to email Pivotal Tracker support and find out why our
updates arent syncing?
Right away, boss.
I cant afford not to do everything in my power to make everyone elses job easier.
Takeaway: Ego has no place here; your job is to do absolutely anything that isnt a
good use of your developers time. Otherwise, youre putting your growth at risk.

Theres Lots More to Learn


Ive been a non-technical founder for almost ten years now, and Im still learning
new lessons every single day.
But right now, if you asked me what I wish I had known when I started, this would
be it.
If youre a non-technical founder (or thinking of becoming one), I hope these
lessons help you succeed in working with technical people.
And if youre technical, I hope this helps you understand the perspective of the
non-technical people you work with, and how you can help them help you more
effectively.
More than anything, I hope you understand that not being technical should never
be the reason you dont pursue a startup.
Get out there, get started however you can, and learn the skills you need along the
way.
247

Its Lonely Being a Single Founder


May 15, 2014

As a single founder, I felt like I was carrying


a weight that I couldnt share with anyone.
Heres how Im fighting back
Are you sure you have what it takes?
Your chances of success would certainly be higher if you had someone technical
leading the charge.
To be completely honest, I dont really know if you can handle this on your own.
Maybe you should quit now.
The objections and criticisms flew, and there was nothing I could say to shut them
up.
After all, I was dealing with something that people much smarter and more
successful have failed to beat; I was trying to quiet the voices in my own head.
I cant remember connecting with any line so deeply as when Jonathan Hefter told
Alyson Shontell that starting [his company] as a sole founder was the most
isolating experience of my life.
My goal here is not to write a whiny post complaining about my lot in life. All
things considered, I have it really damn good.
248

But the issues and challenges of being a single founder are unique to the job, and
they can absolutely derail your business.
I hope that by writing about it, I can help other founders going through the same
thing battle through this crippling obstacle and come out stronger on the other
side.

The Loneliness of Being a Single Founder


Im not a lonely person as some might traditionally think of the term.
Im happily engaged.
I have amazing, fulfilling, deep friendships with people that I love and care about
very much.
But single founder loneliness is solitude unlike any other.

Solitude

Every responsibility and every failure is yours.


Im surrounded by brilliant, motivated, hard-working people at Groove.
Every single day, we work really hard together on building this business and
helping our customers be successful.

249

I help wherever I can, but our team does a lot of things that I cant or dont know
how to do.
But at the end of the day, if theres a failure in the chain, Im responsible.
I made the decision about who should handle which tasks.
Im the one the customer is angry at for something going wrong.
Ultimately, its my fault.
On an even more painful level, if the business fails and my employees lose their
income
Thats 100% my fault.
Its one of my biggest fears as a founder, and while it gets easier as the business
grows more successful, it never truly goes away.
At my last company, we had four co-founders. While none of us wanted the
business to fail, there was at least some comfort in knowing that there were
always three others bearing and talking about that same burden.
Theres literally nobody else in the world who bears that same exact responsibility
for your team as you, the lone founder.
Thats an incredibly isolating feeling.

Four Ways to Beat Single Founder Loneliness


I dont have all of the answers yet.
Its a challenge I still struggle with at times.
But Im feeling massively better about being a single founder now than I was six
months ago, when every day felt like I was sitting alone on an island with no
escape.
Heres how I changed that:

1) I Realized That in Some Ways, Im Not Alone.


For too long, I made the mistake of thinking that because nobody in my life related
exactly to what I was going through, they wouldnt understand.

250

But when I actually tried talking to a friend about it over lunch, I was shocked at
how relieved I felt afterwards.
How simply getting the words this fucking sucks, man out and into the ears
of a supportive, comforting person instantly lightened the load.
Hes never been a founder. Hes never worn those shoes.
But he listened, and he told me that things would be fine.
It doesnt matter if thats a lie. It helped.
My friends and family come to me for support with problems I may never relate to:
medical problems, job challenges, other personal issues.
Im always happy to lend an ear, and in almost every situation, I can tell that the
other person feels better after we talked.
I have no idea why I was scared to do the same.
Now, when Im feeling particularly overwhelmed, I make it a point to take time out
of my day and have lunch with a friend, or talk about it over dinner with my
fiancee.
And it always helps.
Takeaway: Just like any other problem, talking to someone about it can be super
helpful. As I learned, it doesnt matter if that person doesnt know exactly what
youre going through. Just talk.

2) I Disconnected
One of the things that made founder loneliness worse was being constantly
confronted with it.
Id get emails, support requests and Tweets that were prominent reminders of
decisions and responsibilities that only I had to deal with.
When Im working, thats fine. Its part of the job I signed up for.
But when it bleeds into the rest of my life, its a constant source of anxiety.
I tried a lot of things: meditating, taking long walks, forcing myself not to think
about things.

251

But in reality, the only thing that truly worked for disconnecting was, quite
literally, disconnecting.
I began turning off push notifications on my phone in the evenings.
If I was doing anything on the computer unrelated to Groove, Id close my email
client.
I stopped checking Twitter just because.

Disconnected

On the whole, those 3-5 hours of being totally disconnected every night have
been one of the biggest breakthroughs in battling not just single founder stress,
but any stress altogether.
Takeaway: You can do whatever helps you disconnect from your work, as long as
you do something. For me, that meant turning off every reminder of Groove for a
few hours a day.

3) I Started Taking Better Care of Myself.


Perhaps the most obvious and most-often repeated way to battle loneliness
and anxiety is by getting healthier.
The problem is that getting healthier is absurdly vague. Where do you start?
And a Google search for get healthier yields millions of tips and solutions that
are enough to overwhelm anyone.

252

Overwhelming

For me, the mindset of well if I want to be healthy, I need to exercise five times a
week for the rest of my life causes as much anxiety as what I was trying to cure in
the first place.
So I started small.
I exercised once per week for a while.
That made it easier to step up to two.
And three.
Now, I look forward to my workouts, because I know that theyre helping me battle
stress and making me happier.
In a similar vein, I began to stand instead of sitting.
I bought a standing desk, and started using it for an hour each day.

253

And then two hours.


And three hours.
Now, I spend about half of my day standing up, my back feels much better, and I
dont get into the same desk slump I would find myself in after being slouched
over for ten hours straight.

Standing Desk

These arent huge-scale health changes. They were tiny steps I took to improve
my wellbeing, and even those small changes made a big impact on dealing with my
founder loneliness.
Takeaway: Whether youre a founder or not, getting healthier can go a long way
toward helping you deal with your stress. And it doesnt take changing your whole
life. Start small, and the results will motivate you.

4) I Practice Openness With the Team.


Around the time we started this blog an exercise in transparency with our
audience we began to be more open and transparent internally, too.
On our weekly call, I make an effort to bring our team in on the state of the

254

business; where its going, how were doing, how far we are from breakeven, things
like that.
I ask for feedback.
And then I act on it.
Weve recently been automating this process with 15five, and its brought a lot of
great changes to the business.

15five

Having great people around me that have the ability, knowledge and willingness to
offer feedback brutal, honest insights is hugely valuable.
And when I am feeling stressed about a choice I have to make, I talk to them about
it.
To date, nothing bad has ever happened from asking the team to weigh in on
founder-level decisions.
It brings us closer together, makes everyone happier and more invested in the
business, and on a personal level, it makes me feel like I dont sit on an island.
Takeaway: Being open and honest with your employees can go a long way in
making you feel less isolated. And it has massive benefits for the team and your
business, too. Theres a whole lot less that you cant share than you probably
think.

Were All in This Together


Single founder loneliness sucks.
Theres no doubt about it, and theres no way to avoid it altogether.
But hopefully my experiences can help you deal with it better.
255

To not be afraid to talk to people about your problems, like I was.


To not constantly be surrounded with reminders of the loneliness, like I was.
To not ignore the loneliness-crushing benefits of healthy habits, like I was.
And if you cant think of anyone youd want to share your burden with, then just
share it below in the comments. Well all help each other.

256

The ROI of Blogging: What the Groove


Blog is Worth to Our Startup
May 22, 2014

No business effort is a success unless it


makes money. Heres what this blog
means to Grooves bottom line
Wheres the value in this?
It was a fair question.
And as much as I wanted to go with my emotional knee-jerk reaction of its
content marketing, and were getting traffic, and everyone knows its really
valuable!, I also knew that that wasnt good enough.
The question was posed by one of our angel investors a brilliant old-school
businessman who was about as far from a digital marketer as one could be.
It was a few weeks after we started blogging, and it was also the first time I was
forced to truly dig deep to answer that question.
But it was a worthwhile exercise, and its forced us to keep a close eye on the
business metrics related to the blog, and not just the vanity numbers.
Blogging or at least our blogging isnt free.
257

But it is relatively cheap, especially compared to other channels.


And most of the costs only become serious with growth. The barrier to entry is
next to nothing.
Aside from my own time spent on the blog each week, heres what it costs us:
$500 per month: Engine Yard hosting for groovehq.com
$129 per month: Campaign Monitor, which we use to send emails to our
subscriber list
$1,500 per post: Team hours spent on writing, editing, research, design and
coding
Now, there are certainly other costs we sometimes incur related to the blog:
KISSmetrics, Optimizely, Crazy Egg and some other apps and tools. But wed be
paying for these anyway, as we use them heavily for our marketing site; the blog
traffic doesnt push us into the next pricing tier for any of them.
That brings us to a grand total divided by four posts per month of $1,657.25
per post.
And heres what we get for that

1) Subscribers
Subscribers are not signups, true.
But looking at our data, theyre just about the next best thing.
In their first 30 days after subscribing, roughly 10% of our subscribers sign up for
a free trial of Groove.

Subscriber Trial Signups

258

Compare that to a marketing site conversion rate for non-subscribers of around


5%:

Non-Subscriber Trial Signups

Subscribers are twice as likely to become trial users.


And as we get deeper into the funnel, the numbers look just as good.
Trial users who were subscribed to the blog before they signed up for Groove
convert to paid users at around 18%.

Subscriber Trial Conversions

259

Non-subscribers convert at around 12%.

Non-Subscriber Trial Conversions

Subscribers become paid users at a rate thats roughly 50% greater than nonsubscribers.
What does that mean for our bottom line?

Subscribers vs. Non-Subscribers

A subscriber is worth more than 3.6 times the value of a non-subscribing visitor.
Takeaway: We found that a blog subscriber is multiple times more valuable than
an average site visitor. This means that we can focus on optimizing the types of
visitors that mean the most to our business.

260

2) Validation
Not every facet of the blogs ROI can be tracked as systematically as the email list,
but that doesnt mean its not valuable.
We all want to do business with someone we trust.
But for a startup, building that trust with very few users and almost no attention
is really, really tough. We learned that first hand early on.
What weve found is that the blog has done that for us.
I get emails like this every single week:

Blog-Driven Signups

And this:

More Blog-Driven Signups

261

There are many, many more just like these.


One thing thats been interesting to see is the reason people connect with the
blog. For many, its not necessarily expertise or because of how we sell our
product here (we never do), but its because of the transparency and brutal
honesty weve approached the blog with.
A lot of people trust us not because of our authority in the space, but because they
relate with the vulnerability in our blog: the emotions, the stories, the wins and
the failures.
I cant say that this part of it was totally planned and strategized. But its definitely
a welcome surprise.
Takeaway: Trust is a huge driver of buying decisions in any industry. Blogging, for
Groove, was a really effective way to build that trust before we had much of
anything else to show.

3) Social
Through the popularity of the blog, Groove has entered a conversation that we
werent a part of before.
When we publish content that people find valuable, they love to share it.

Blog Mentions

Many of our readers become subscribers, and we know that blog subscribers are
more valuable than non-subscribers.
But were also seeing more and more mentions of our product on Twitter and
elsewhere around the web.

262

Product Mentions

Of course, the blog might not be solely responsible for that, but anecdotally, this
trend correlates closely with the blogs launch.
In talking to some of the customers who have referred us, we hear the blog
mentioned quite often.
Were finding that with the blogs popularity, customers are more likely to stick
their necks out and recommend Groove.
Again, we cant back this one with data (yet), but its an insight that really surprised
me, and its too interesting not to share.
Takeaway: Our presence online has been massively impacted by the success of the
blog, and it has driven referrals and signups from customers who otherwise might
have never heard of Groove.

4) X-Factors
There are a lot of X-factors that weve been able to take advantage of because of
the success of the blog, and the legitimacy, validation and authority that it brings
Groove.
Weve gotten huge opportunities for partnerships with amazing companies like
HipChat.
Weve been able to write for much bigger audiences at blogs like KISSmetrics,
Buffer and Shopify because they loved our work here.
Weve leveraged the influence of our blog to help put together a rock-star group
of SaaS partners for our Small Business Stack, which has generated nearly 3,000
signups so far.

263

Weve had a much easier time hiring great talent as the blog has made us a more
appealing name to work for.

Attracting Talent

Weve gotten press mentions and interviews from reporters and bloggers whove
read our posts.

Interview Requests

And weve seen our blog and story used often without us even knowing in
posts and case studies for the power of content marketing.
Many of these have directly resulted in revenue for Groove, and none of them
would have happened without the blog.
Takeaway: Aside from the obvious benefits, the blog has helped us take advantage
of numerous and big business opportunities, none of which would have been
available to us otherwise.

264

How to Apply This to Your Business


Blogging can be hugely valuable to your business.
It can bring you more authority, more validation, more customers and more
revenue.
But only if you do it right.
Buying keyword-optimized content from content farms isnt doing it right.
Writing fluffy content thats exactly like what everyone else is doing isnt doing it
right.
Doing it right means doing your best to publish valuable, interesting and useful
content, and then doing everything you can to make sure that your potential
customers see it.
You can start the way we first did, by just trying a bunch of things and failing until
we got it right.
Or you can read about the strategies we used when we finally did get it right.
You can start here: How We Grew Our Blog To 5,000+ Subscribers In Five Weeks
and How We Got 1,000+ Subscribers From A Single Blog Post In 24 Hours.
But wherever you start, start today.

265

The Simple Test That Increased Our


Referrals by 30%
May 29, 2014

One of our biggest focuses at the


moment is growing referrals. Heres one
test thats worked so far
Sure, a lot of companies do it, but seems like it would piss people off.
We had a lot of doubts on our team about testing something that would effectively
force referrals onto our customers.
Strong doubts that, at numerous points, very nearly killed the tests before we
even started them.
Several months ago, we were going to test a Powered by link in our support
widget (the Contact Us widget that appears on Groove customers sites), and I
was really hesitant to pull the trigger.
It seems a bit spammy.
But then we resolved to ask our customers about it first.
And, to our surprise, for most of them it was a total non-issue. The tiny link we
were proposing didnt bother them one bit.
266

And after we launched it, we even heard from some that they were happy to stop
having to answer questions about which helpdesk they were using.
And it certainly helped us.

Powered By

As our customer base has grown, the conversion rate hasnt stayed at 19% like it
was before, but we still get a significant amount of traffic from it, and that traffic
signs up for a free trial at about a 9% rate (though it usually takes at least a couple
of visits).

Powered By Conversions

But there was more work to be done


267

The Test That Increased Referrals by 30%


The obvious question: if the Powered By hack worked on the support widget,
where else might it have value?
We weighed a number of options to test, and decided to start with the first one
that came to mind: on our customer satisfaction ratings page.
Some background: when a Groove user sends a support reply to a customer,
theres an embedded link in the email that asks the customer to rate their reply.

Rate My Reply

Clicking on one of those links takes the customer here:

Ratings Page

268

At the bottom of that form is where we placed the referral link (though, as you see,
with some altered copy).

New Referral Link

It took about a week, but the results were pretty clear: while fewer people were
clicking through this link (for obvious reasons fewer people see it), those who
did click signed up for trials at nearly double the rate of those who clicked on the
support widget.
When we account for trial-to-customer conversions, this second link ultimately
gets us about 30% more referrals than the widget link.
Takeaway: If something works, dont leave it alone. Use it as an indicator that
theres more to be gained from taking the same approach and applying it
elsewhere throughout your business.

269

Why It Worked
Weve spent a lot of time talking and thinking about why the referral link
performed so much better on the ratings page.
While we cant say that we know the answer for sure, weve got some ideas that we
feel pretty good about:

1) The Visitors Are More Qualified to Try Groove


This probably accounts for conversions more than click-throughs.
The interaction that the prospect has had with Groove goes deeper than simply
clicking to open the Support Widget. Theyve used the customer-facing side of the
app more; sometimes that means that theyve clicked through the widget to find
answers to their question, or theyve filled out the contact form, or completed a
live chat with the support agent.
They know Groove better than the average passerby, and thus they know what
theyre getting into when they sign up for a trial.

2) The Context of the Offer Is Stronger


A prospect who sees the Powered by link on the Groove widget isnt really
getting promised much.
The promise of the Powered by link is that if they click through, then they, too,
could have a support widget just like the one theyre looking at.
But on the ratings page, that promise is a bit different.
Presumably, the prospect has just received great support. Theyre happy about it,
and they, too, want to deliver the same support to their customers.
Now when they see the referral link, they can tie it to a stronger end benefit: great
support, and not just a support widget.
Again, I dont have data to back this assertion up; but my sense is that this may be
the strongest force at play here.

3) The Message Is Stronger


Clearly, weve changed the copy to a more benefit-focused promise in this test.
The only way to compare the two links, apples-to-apples, would be to have the
same exact copy, and well run that test in the near future.
But for now, this test suggests to me that we can improve the copy on the widget
270

link. Whether itll make a difference in that context, I dont know.


But it seems like its worth a test.
Takeaway: Its not enough to simply know that something works. Understanding
why it works is what will allow you to duplicate those results. Unfortunately, that
understanding isnt always as data-driven as wed like it to be, but thinking, talking
and hypothesizing can be valuable exercises, too.

How to Apply This to Your Business


The point here isnt necessarily that you should add a Powered by link to your
app.
For many businesses, that probably doesnt make sense.
The point is that as you strive to help more and more customers its important
to think about all of the different places you might find those customers, and try
to put yourself in those places.
As weve learned, if you do it right, it wont come across as spammy or annoying to
the people that matter.

A Long Way to Go
Were just touching the tip of the iceberg when it comes to referrals, and I hope
that this link becomes a tiny part of our overall execution.
Admittedly, its one of the biggest holes in our acquisition strategy at the moment.
Were working hard to implement a real referral program, and we expect to launch
something in the coming weeks.
Well definitely be writing about our experiences with that.
In the meantime, I hope that this post has given you an idea or two to test in your
own business. As you can see, even the small stuff a text-only link, for example
can have a big impact.

271

Why Bug Reports and Feature


Requests Dont Overwhelm
Us Anymore
June 5, 2014

We were getting crushed under the weight


of incoming tasks. Heres how we turned a
firehose into two simple, efficient systems
It was bad.
Really bad.
And the more we grew, the worse it got.
There will always be some level of chaos involved in running a startup, but we
were hitting a point where the chaos was deeply hurting Groove.
Every day, customers would send us bug reports and feature requests by the
dozen.
And while we had tools (practically living inside of Pivotal Tracker), we didnt have
systems, and so the tools were nothing more than a place to house the chaos,
rather than organize it.

272

We would pluck tasks based on snap judgment calls, mostly for the developers
from the master list, and spend our days battling against the ever-growing tide of
incoming work.
We were spending far too much time dealing with workflow issues, and if we ever
wanted to crawl out of that hole, we had to get real about managing incoming
requests and reports.
So a couple of months ago, thats what we did.
And the change has been massive.
We dont feel overwhelmed by our backlog.
Were not constantly scrambling to catch up.
And our development team isnt left wondering how to prioritize and tackle tasks
anymore.
All it took was a couple of days spent building systems to organize and manage the
chaos.

The First System: Bug Reports


As a software company, bugs are the bane of our teams existence.
They piss off our customers, they frustrate us, and they cost us a lot of money.
And while well always have to deal with fixing bugs, thoughtlessly dumping
incoming bug reports into Pivotal Tracker was crushing us.
We needed a better workflow to help us spend more time fixing the bugs that
matter most, and less time figuring out what bugs we should tackle next.
After exploring a number of options and testing different approaches, the best
solution was a simple and obvious one: prioritize at the front end when the bug
comes in, rather than at the back end when the team is figuring out what to work
on next.
Heres the system we built to do that:

273

274

With this simple system developers are never left wondering what to do next and
bugs are addressed in a straightforward, organized flow.
This workflow has singlehandedly saved our team more than ten hours per week
on managing bug reports.

275

The Second System: Feature Requests


Like any other growing SaaS business, we get a lot of feature requests.
Some of them will never get made, some of them need to be considered carefully,
and some of them are no-brainers for developing.
Regardless, all of them need to be organized and acted on, even if that action is an
email letting our customer know that we cant build a particular feature.
Just like with bug reports, managing feature requests was much easier a few
hundred customers ago.
And just like with bug reports, we found that building a system to handle incoming
requests has saved us huge amounts of time and money.
Heres how we deal with feature requests:

276

277

Just like with bug reports, the key here is to act on each request immediately, even
if that action is to file the request into a bucket.
Our weekly and monthly roadmapping meetings keep this flow moving, and we
always know what were working on next.

How to Apply These Systems to Your


Business
While the two processes have a few differences, the key factors that make them
work are the same:
1. Every incoming task is prioritized the day it arrives, rather than tossed on
the pile.
2. Theres a single gatekeeper whos responsible for that initial prioritization
decision.
3. Theres a bucket for every conceivable task; nothing gets stranded in nomans land.
4. Theres a single, central place where we can keep track of everything. We
always know whos accountable for what.
Thats really it. While we use Trello and Pivotal Tracker, weve learned that the
tools matter far less than the systems.
If youre not already doing it, I hope youll give these systems a try. If youre like us,
itll save you time, money and a whole lot of unnecessary work.

278

Lessons Learned Sending a Net


Promoter Survey to 4,000 Users
June 12, 2014

Weve done thousands of surveys, tests and


interviews to learn from our customers.
Heres what happened when we decided to
measure our Net Promoter Score
Over the past year, weve done a lot to collect qualitative data from our customers.
Weve had thousands of conversations that helped us inform the redesign of our
marketing site.
We ask every single new customer a simple question that has given us incredibly
valuable feedback on their problems and motivations for signing up.
And when customers leave us, we use it as an opportunity to learn and grow.
But one of our biggest challenges has always been quantifying that qualitative
feedback.
For example, weve got thousands of Qualaroo responses. Juicy, open-ended
answers that give us insight into the minds of our prospects.

279

And that insight is massively valuable.

Tons of Feedback

But we havent been very good at turning that feedback into quantifiable data that
we can use to benchmark ourselves and measure the success of the steps we take
to improve.
Thats why we decided to try a Net Promoter Score survey.

Net Promoter Score: A Brief Overview


In short, NPS measures customer loyalty and sentiment about your business by
asking two simple questions:
Results from the first question tell us how many of our customers are promoters
(those who respond with a 9 or 10), passives (7 or 8) and detractors (0 to 6) of
Groove.
Results from the second question tell us why.
Many businesses use NPS to determine which customers to target for referral
campaigns. And we certainly plan on doing that, as referrals are a huge focus for
us at the moment.
But what sold us on the idea of doing NPS was that wed finally have a quantitative
benchmark for how our customers feel; one that goes a bit deeper than just
looking at revenue or retention.

280

Net Promoter Score Survey

Takeaway: The Net Promoter Score survey is a popular way for brands to measure
customer loyalty. We knew that a lot of companies use NPS and decided to take
the plunge, but we werent quite sure what to expect

Deploying Our NPS Survey


After looking at a number of options, we decided to go with Promoter.io, a web
app that automates much of the NPS-deployment process.
Were not getting anything from Promoter.io for mentioning them, and you can
probably get great results from using most survey tools, or even a free DIY
solution like Google Forms. But we were very happy to have a turnkey app that did
the hard work for us.
We sent a survey to 4,000 Groove users. Within hours, the responses started
coming in. It quickly became pretty clear that the data we were getting our hands
on was going to be very valuable.
Takeaway: As always, choosing the right tool for the job isnt nearly as important
as actually doing the job. There are a number of options at your disposal. Pick one
quickly and act.
281

Qualitative Feedback
Now, weve collected a ton of qualitative feedback before we did NPS, and that
wasnt really the hole we were trying to plug.
But as weve learned, you can never get too much insight into what customers are
thinking, and it was exciting to get some of our older findings confirmed, and
others brought into question.
From promoters, we learned what our biggest fans love about Groove.

Promoter Feedback

From passives, we learned what we need to do to take some of our users from
liking Groove to loving it.

Passive Feedback

And from detractors, we learned about what we really needed to do better.

Detractor Feedback

282

And on a smaller scale, some of the detractor feedback has shown us what types
of customers were not a great fit for.
Sorting the data, weve also learned some great lessons about what our customers,
as a whole, value most about Groove.

What Customers Love Most

Takeaway: The qualitative feedback we got from our NPS survey was really
valuable to us, and we already make an effort to have thousands of conversations
each month with our customers. If you dont already do that, then the feedback
you get from NPS could very well change your business.

Quantitative Results
When all was said, done and tallied, we netted out with a score of 11.
While there are guidelines of differing opinions all over the web, on its own, that
number is pretty meaningless to us.

283

But as a benchmark metric for gauging the sentiment of our customers, its
absolutely critical and precisely the reason that we did the survey.
It makes our path to success clearer, and our strategy much more measurable.
Takeaway: There are a lot of ways to measure how good your Net Promoter
Score is, but thats not what were focused on right now. The most valuable part of
this effort, for us, was a benchmark that we can now test ourselves against over
the coming weeks, months and years.

What Weve Done, and What Were Doing


Our first move was to email every customer who logged a response, thanking
them for their time and feedback. In some cases, we shared their enthusiasm. In
others, we promised to do better (and meant it).
In hindsight, this increased the value of our survey quite a bit: around 20% of the
emails that we sent got responses with even more feedback.

The Value of Follow-Up

We put every bug report and feature request that the responses contained
through our prioritization workflow, and hope to tackle many of them in the
coming days.
The responses are only about a week old, so we havent done a whole lot yet.
But theres much to come.
Now that we have a quantifiable goal to aspire to, our roadmap is much clearer.
Next time, we want our NPS to hit 20.

284

We plan on repeating our NPS survey quarterly, and our efforts in between will be
focused on turning our passive users into promoters.

How to Apply This to Your Business


The Net Promoter Score survey, based on our early experiences, looks like it will
be tremendously valuable for us in the long run.
But every business is different, and the point here isnt necessarily that you need
to run an NPS survey, too.
The point is that, like many startups, we try to optimize a lot of things:
conversions, traffic, retention, engagement.
But most of us dont pay too much attention to optimizing customer feedback.
This exercise has given us a great way to optimize the way that we listen to our
customers, and to set quantitative benchmarks to make sure that were acting on
what we learn.
So whether you use Promoter.io, forms, surveys, email, Skype, telephone, or any
other channel: please take this post as a reminder to go out, ask a lot of questions,
and listen very hard.
Its not the sexiest part of optimization, but if your experience is like ours, itll be
more valuable for your business than any single conversion hack could ever be.

285

Our Startups 12-Month Growth


Strategy
June 19, 2014

Until about six weeks ago, our startup has


been in a constant scramble to keep up and
get better. Heres how we changed that

That email led to the most significant strategic meeting our team has had in the
lifetime of Groove.
286

Over the past couple of years, weve spent a lot of time with our heads down,
focusing on putting out todays fires and building whatever is necessary to keep
the business running tomorrow.
But we havent, as a team, spent a lot of time talking about what happens beyond
that.
We havent had a serious, organized discussion about 3, 6 and 12-month goals,
strategic roadmaps and action plans to achieve those goals.
Weve simply been too focused on today.
But finally, a few weeks ago, we had that discussion.
For four and a half hours, we brainstormed, challenged each other, and came up
with the blueprint for how were going to achieve our 12-month goal.
In the interest of transparency, and because I think it can help other companies
structure their own thinking about roadmapping, the email that resulted from that
discussion is below.
Theres not much focus on specific tactics, to-dos and processes; those are
separate discussions, and weve got posts in the works about each of them. I will
say this: in the six weeks since weve started executing on this plan, weve learned
and matured significantly as a team, and the way we work now is very different to
the way we worked even a couple of months ago.
With that said, below is a behind-the-scenes look at how we think about growth at
Groove.
The below is taken from an internal email. Its not prettied up or censored for the
blog.

Over the past two years, weve gone from having nothing but a barebones prototype to becoming one of the fastest-growing startups in the
customer support space.
We hit Product/Market Fit.
We have customers that love Groove.
And weve built the foundation for a brand that people are starting to
notice.

287

Weve done a lot of things right, and weve learned from that.
Weve also done a lot of things wrong. And weve learned from that, too.
We have a massive opportunity in front of us. In a 2013 report, IDC
estimated that there were close to 76 million SMBs worldwide. Our own
research suggests that many of them have not been able to find or
afford the right customer support software. And that many of them are
using products that they hate.
If we execute on our mission of helping as many of those companies
succeed as we can, well all win.
Over the next twelve months, our teams long-view focus will be on a
single goal: to have 5,000 paying customers using Groove.
To do that, our strategy will stand on three pillars:

The Three Pillars of Our Growth


Strategy
1) Leadership in the SMB Market
Weve gotten here by serving small businesses and entrepreneurs.
Unlike some of our competitors, were not going to move upmarket. Our
product, our blog and our other efforts have all helped SMBs grow, and
were going to keep doing that. As youll see below, we have plans to
increase by a huge margin the amount of value were delivering to
our community. Our mission is to become the preeminent resource for
small businesses when it comes to support, growth and business
strategy.

2) Building the Groove Brand


As weve seen many times in the SaaS space, a good product isnt enough
for long-term growth. We need to build a lasting brand that people love
to do business with. Weve begun to do that with the 100K blog, but
theres a lot of work left to be done.

3) Becoming Even More Data-Driven


Theres no doubt that collecting, analyzing and using the right data can
help us make smarter business decisions about our time, our budget and
our roadmap. Weve seen it with our own successes. We need to do a

288

better job of this. We need to get to a point where we can treat our
efforts marketing channels, product features, team hours and focus
as levers; when we push or pull one, we know what result to expect. We
cant depend on luck; this will be the only way to make our growth
systematic.

What Are Our Biggest Concerns?


As we discuss and execute on our strategy, we cant risk being blind to
the risks and worries we have. Its the only way to tackle them head on
and ensure that they dont hurt the business.

Building the Right Team


Are we doing everything that we can to put together the right mix of
talent to take Groove to the next level? How can we hire the right
employees as we grow?
Its not enough to be good marketers, developers, designers or support
agents. We all need to think like startup CEOs; the goals in this email
our business vision needs to drive every work decision that any one of
us makes. Were all responsible for lighting the fires under our own
asses.

Doing More Faster


To meet our goals, we need to be moving faster than we are. In order to
do that, well need to set more regular milestones and timelines to
constantly be pushing forward and not get stuck working on any one
thing. Moving forward, well work together to set quarterly and monthly
goals to keep us focused on the right tasks to progress toward our 12month goal.
[Alex note: since we wrote this, weve developed an entirely new system of benchmarking
and goal-setting (based on a system used at many successful companies) that has made a
huge impact on our productivity and workflow. Excited to share more on this soon.]

Bugs and Infrastructure Debt


A good portion of our development week is spent squashing bugs. If
were going to accept that this is going to be the case, I think we should
realistically look at our resources and figure out how we can account for
these resources being used.
In addition to bugs, we cant seem to get over our infrastructure debt.
With bugs and infrastructure stories like parsing etc. we cant ever seem

289

to get over the Next Up bucket in PT. This is unacceptable and well
never be able to grow if this continues.
[Alex note: since we wrote this, weve covered one of our solutions to this issue in this post
about our bug report workflow.]

Estimations
Weve been consistently off on our estimates of how long things will
take. Most notably, Trends, Settings, Parsing etc. have all taken 3x longer
than expected. In order for us to more accurately plan for future growth
initiatives, we must get better at estimating releases. On that note, when
we release features we need to make sure were not cleaning up that
feature for days/weeks to follow.
[Alex note: the systems in the post I linked above have also helped us get better at
estimating and planning.]

How We Plan to Accomplish Our Goals


Doubling Down on Blogging
To date, our content efforts have driven more users than any other
channel. Were going to grow this through:
Keyword research to better validate blog topics (especially for the
new support blog)
Launching a new, improved support blog in the next month
Closely tracking blog metrics and movement of blog visitors
through our funnels
Publishing more guest blog posts on high-profile outside blogs
[Alex note: weve got two very exciting guest blog posts planned on sites that everyone
reading this blog will recognize. The first drops on June 24th.]

Community Building & Online Engagement


While the community on our blog is incredibly active and engaged, were
going to be doing more to build the Groove brand outside of our own
web properties:
Developing a data-driven social media strategy (which platforms
are best for us?)
Sourcing case studies from Groove customers to be published
around the web
Creating a community for entrepreneurs (and Groove customers)
Building the relationships we need to get more high-profile
customers using Groove
290

Organic SEO
Through the blog, were already ranking for a number of competitive
startup-focused keywords on Google. Were going to be taking a more
strategic approach to organic SEO by:
Developing personas for customers who are closer to being ready
to get value from Groove than the traffic were currently getting
Doing keyword research to find out what those customers are
searching for
Building blog/webinar content and targeted landing pages
specifically for those interests
[Alex note: to date, weve largely ignored SEO. While itll never change the way we write,
it will help us figure out the best ways to add value in ways that more people are looking
for.]

Referrals
Weve talked about this quite a bit, and its going to be a big focus for us
moving forward. We need to build a more structured referral engine,
whether we build it ourselves or use a turnkey solution.
[Alex note: weve written quite a bit about this in the last few weeks.]

Expanding Integration Partnerships


Our HipChat integration has been a big boost to Groove, both to our
customer base and our brand. We should continue to build an
ecosystem for companies to integrate with Groove, and to do that, well
need to launch a lot more integrations.
Part of that is on the development side. Part of it means building deep
relationships with potential partners to help us spread the word when
we launch the integrations.

Product Improvements
Weve done a lot of great work to take the product from where it was
two years ago to today. And Im really proud of our team for that.
We all know that theres a lot of work left to do to make Grooves
software the no-brainer best option for SMBs.
To do that, well:
Invest resources into strengthening the core infrastructure of
Groove to minimize bugs, performance lags and regression issues.
291

Rewrite the Knowledge Base app so that it becomes good enough to


be a standalone
Fix Live Chat bugs to make the experience better
Make the transition from other helpdesks to Groove more seamless
Put more polish on the app to make it more fun to use (a la Slack,
MailChimp, etc)
As a team, we also need to do a better job setting realistic expectations
for development timelines. This will help us set better goals and have
more wins, rather than spend our time playing catch-up.
[Alex note: weve got a lot to do here, and will keep our development team incredibly busy.
More on our plans for this coming soon.]

Driving Paid Traffic


While it wont be our primary strategy, well test driving paid traffic to
support our other efforts, including:
Retargeting
Pay Per Click on Google, Facebook, LinkedIn, Outbrain
Native Ads elsewhere
[Alex note: weve tested some paid traffic in the past, but werent impressed with the
results. Well revisit this more strategically and see how it goes, though I doubt itll ever
become a cornerstone of our business; organic traffic has been exponentially more
valuable to us.]

Improving the Marketing Site


Our marketing site converts, but it can convert much, much better. Over
the next twelve months, were going to be:
Testing all major elements of the page
Testing more video content
Building case study videos
Creating more targeted landing pages that are vertical-specific,
content-specific and partner-specific
Improving our feature tour
Doing SEO keyword research to optimize our copy
[Alex note: Our redesign made a big difference, but theres much more to do. Expect to
read a lot about this on the blog.]

Better Lead Nurturing


With more than 10,000 blog subscribers, among thousands of other
email addresses, we have a lot of qualified leads, and we havent been
doing a whole lot to nurture them. To change that, well be:
292

Implementing drip campaigns for new subscribers that drive them


toward signup
Creating more middle-of-the-funnel content for qualified leads
[Alex note: were not going to start selling here, or to our blog list. But we will be exploring
ways to ensure that when people are ready, they know exactly where and how they can
sign up for Groove.]

What now?
It sounds cliche, but this is an exciting time at Groove.
Weve turned down multiple acquisition offers.
Our valuation has continued to rise dramatically.
We truly are on the verge of breaking out as a major player in the SaaS
support space, and were all poised to benefit from that.
What we need to do to accomplish it is keep our eyes focused on the
next big goal: 5,000 paid companies.
In the coming days, well work together to set monthly and quarterly
milestones that we can work towards to ensure our success.
Well start executing on these strategies.
Well track and test everything.
And together, well win.

What Happens Next?


Clearly, weve got a lot of work to do.
Weve gotten started on breaking much of this strategy into individual and team
action items, and building more granular tactical plans for executing, tracking and
testing every element of our strategy.
Things are going well, and the team is excited to have a single, focused vision to
drive toward, rather than what felt like an infinite scramble.

293

I cant wait to see what this effort brings.


In the meantime, my goal in sharing this was to get you thinking about your own
business goals, and how you can accomplish them strategically and systematically.
Of course, feel free to copy any of the content above for your own plan. I hope its
as useful for you as it has been for us.

294

How Weve Reached More Than


1 Million People by Guest Blogging
June 26, 2014

Blogging has been the foundation of our


strategy for some time, but it turns out
that our own blog was only the
beginning
Holy shit.
Wed never seen numbers like this before.
Watching real-time analytics, it quickly became obvious that April 22nd would
easily become one of our biggest traffic days ever.
Within an hour of the post being published, we had 1,000 new unique visitors.
That soon turned into 5,000, and then 10,000, and before long, 20,000.
What happened that day?
We published a blog post.
Not on our own blog, but on Buffers.
And it was doing really well.

295

Today, that post has been shared online more than 10,000 times, and has
cemented guest blogging as a cornerstone of our growth strategy.

The Value of Guest Posting


Weve now had guest posts published at OnStartups, Shopify, KISSmetrics, Buffer,
AngelHack and Copyblogger, and the impact has been tremendous.

GrooveHQ.com Trac From Guest Post

[The Copyblogger post isn't shown above, as it was only published two days ago and our traffic data is
incomplete.]

These numbers dont necessarily reflect the overall influence of any of these
blogs; a lot of factors go into the success of each post, from the effectiveness of
the headline to the relative usefulness of the content to each specific audience, or
even what day of the week the post is published.
In any case, guest posting has exposed us to huge new audiences quickly and
efficiently.
We have just over 10,000 subscribers to the Groove blog.
296

In sum, our partners have more than 1 million subscribers.


And reaching those subscribers costs no more than the resources it takes to write
a great blog post.
Takeaway: Theres no faster or cheaper way to reach massive audiences than
guest blogging. By leveraging existing audiences in a way that delivers value, you
create opportunities for exponential growth.

How We Come Up With Guest Content Ideas


We dont think about guest content the same way we think about our own posts.
The Journey to 100K blog is about Grooves journey, and thats what people come to
read about.
No other blog has the same focus, and so nobody elses readers care all that much
about Groove.
To write guest post pitches that not only get accepted, but that turn into great
blog posts, you need to think about each specific audience and their unique
interests, goals and challenges.
To do that, its helpful to think about a few things:

1) Whos Reading the Blog, and What Do They Care About?


Shopifys readers tend to be Ecommerce business owners, while Buffers audience
wants to know how to make the most of their social media and content marketing.
KISSmetrics attracts analytics buffs, and OnStartups is, no surprise here, focused
on startups.
Good guest posts have nothing to do with the writer, and everything to do with
the audience.

2) What Audience Challenge Has the Blog Not Tackled Yet, and Can
You Solve It?
If you know the audiences challenges, itll be easier to determine what remains
unsolved.
For example, we knew that Buffers audience wanted to succeed at content
marketing, and that Buffer had put out a ton of amazing content around it. But one
approach that hadnt been addressed was how to set the scene in blog post
intros. It was a topic that we care very deeply about, and that were well-qualified
to write about, so thats what we pitched.

297

3) What Kind of Content Does Well on This Blog?


This isnt data science; its easy to take a cursory look at comment and share
counts and get a general feel for the types of content that perform best on a given
blog. For a number of blogs, itll be Top 10 lists and slideshows. For others, itll be
story-driven content, while some find their success in image-heavy posts.
Again, doing just a little bit of research can help inform your pitch and set you up
to write the best post possible.
Coming up with great content is the most challenging part of this process, but
putting in the hard work of doing research first, and then developing the best post
you possibly can, makes the next step the pitch a lot easier.
Takeaway: Your potential partners blog isnt the same as your blog, and you
should approach it differently. Think about their audiences unique problems, and
solve them in a way that you already know will work.

Pitching Guest Posts


For some posts, weve written the entire post and then pitched it.
For others, weve floated the concept by the publisher before writing.
But in any case, one thing that has remained constant has been our pitch.
Heres the script we used (taking our Buffer post as an example).

Guest Post Pitch

298

A few important things to note:

1) Warm Introduction
This is probably the single most important part of this process.
Weve never pitched a guest blog post cold.
Weve always found a way to make sure that the recipient of the email knows who
we are before they get our pitch.
That might mean developing a relationship in their blog comments, having a
friend introduce us, or any other way in that we can find. For more on this
process, see our post on engaging influencers.

2) Put Their Blog First


A subtle but important point: this isnt just a good post, its a good post for their
blog.

3) Validate Yourself
If youve had guest content published elsewhere, mention that. If not, use any
form of validation you can: subscribers, traffic, press mentions. Dont lie here; if
you dont have anything to share yet, dont worry about it.

4) Post Teaser
Summarize your post in 2-3 sentences, but make sure that the summary is as juicy
as possible. By teasing the content (rather than just attaching it or pasting the
entire post), youre respecting the recipients time; now they dont need to read an
entire post to know whether they want it or not.

5) Call to Action
Using the same call to action we used for our influencer outreach strategy, we
make a clear ask with a direct question. No let me know if you want to see it
here.

6) On the Back End


I wish I could say that we have a bulletproof system for turning guest post traffic
into leads.
But truthfully, were not at that stage yet.
In fact, as embarrassing as it is to admit, this weeks Copyblogger post was the
first post weve built a targeted landing page for.

299

Targeted Landing Page

300

301

But in the first couple of days, weve had some very promising results, and were
excited to keep testing and continue to build out our systems as we move forward.
Takeaway: You dont need sophisticated tracking and funneling systems in place
to get started, but youll want to build these eventually. Still, weve been successful
without them until now.

302

Start Guest Posting Now


If we had known the power that guest posting has two years ago, we wouldve
been doing this a lot sooner.
One of the mandates in our 12-month growth strategy is to double down on guest
posting.
Weve got some great partners and some great content lined up.
Id encourage everyone to do this. Its easily one of the best and fastest ways to
build an audience for your content (and leads for your business).
Your audience is almost certainly different than ours, and the blogs that are best
for you are probably different, too.
But using the process and script above, Im confident that anyone can succeed at
growing their business by publishing guest content thats interesting, valuable and
actionable.

303

6 A/B Tests That Did Absolutely


Nothing for Us
July 3, 2014

Weve written about how A/B tests have


helped us grow Groove. But thats only
the tip of the iceberg
Imagine having a button that you could push to instantly double your conversion
rate, without having to do any hard work, research or trial-and-error?
Sounds pretty amazing, doesnt it?
Itd sure make the struggles of being a startup founder the long days, the
neverending roadblocks, the constant fear a whole lot easier to battle through.
Seeing blog posts nearly every day about how a company doubled, tripled, or
quadrupled their results with the simple flick of a switch even on this very blog
can make it easy to believe that such a button exists.
But one of the hardest lessons that Ive had to learn as an entrepreneur is that, try
as I might, I cant find that button.
And I likely never will.
What we dont see when we look at those big win case studies is the hundreds
(sometimes thousands) of tests that had to completely flop before success
happened with a simple test.
304

I know weve been guilty of only showing the tip of the iceberg ourselves, if only
because the background work doesnt make for very interesting reading.
But I think its important for anyone looking for a magic bullet to understand one
simple truth: testing is mostly failure after failure. If youre lucky, you find a
statistically viable win after a few weeks. Most of the time, we see results after
months of iteration.
To illustrate the point, I thought Id share some tests that are frequently pointed
to as easy wins that did absolutely nothing for Groove.

1) Signup Button Color

Theres a lot of psychology research that points to the impact various colors make
on our behavior, and a lot of companies have gotten results from testing button
color changes. We didnt get the same result.

2) Homepage Headline

Headline/messaging tests have produced big wins for us, and well share those
results later, but weve had dozens of tests end up like the one above.
305

3) Signup Call to Action

We tried to add some urgency to our call to action in the hopes that it would get
more visitors to act. Didnt happen.

4) Email Subject Line

I have a friend who found that free access had a massive impact on her open
rates. Not here.

306

5) Customer Logos

We thought wed try showing customer examples from a variety of industries in


hopes of determining which logos were most relatable to visitors. No difference.

6) Pricing

Fierce forum debates have erupted over whether a price should end in .00, .99 or
.97. In our homepage test, it didnt matter.

307

How to Apply This to Your Business


The fact that these tests failed for us doesnt mean that they wont work for you.
It also doesnt mean that theyll fail for us in a week, or a month, or a year.
It just means that at the time we ran the test, it didnt produce any statistically
significant change positive or negative in our results.
Ive said it before, but one of the most important lessons weve learned as a
business is that big, long-term results dont come from tactical tests; they come
from doing the hard work of research, customer development and making big
shifts in messaging, positioning and strategy.
Then A/B testing can help you optimize your already validated approach.
But my hope is that this post lifted the veil a bit from the standard how we
doubled our conversions with a simple test case studies that so many of us have
published.
Testing can deliver great results.
But be ready for a long, slow haul.

308

Why We Killed One of Our Biggest


Features to Grow Our Business
July 10, 2014

Since we launched, our Live Chat feature


has been a big source of pride for Groove.
Heres why were getting rid of it
Ugh.
Looking at the metrics for our Live Chat app, I knew that things didnt look good.
People werent using it.
We had tried a number of tests and campaigns to drive usage of the app, but
ultimately, we were fooling ourselves.
Our Live Chat app simply wasnt that good.
And it was costing us: each week, our developers would spend precious hours
fixing bugs and supporting an app that our customers didnt love.
Live Chat has been a huge part of Groove since we launched; we brag about it on
our marketing site, we talk it up to our customers, and we know how valuable chat
can be in delivering great support.

309

But the more we looked at the evidence, the more we realized that we werent
proud of the Live Chat app.
We were proud of having a Live Chat app.
Its a key difference, and it kept us from making the decision to kill the app for far
too long.
I hope that by sharing our experiences making the tough call to discontinue a
major feature, youll be less likely to make the same mistakes we did for so long.

Four Reasons We Made the Decision to Kill


Our Live Chat App
1) Usage Was Low
Looking at our user metrics, the adoption rate of Live Chat was, frankly,
embarrassing.

Live Chat Adoption

Compared to our other apps Knowledge Base, for example, has nearly seven
times more users chat simply wasnt connecting with customers.

2) Maintenance Costs Were High


The app, built as an add-on in our first iteration of Groove, had more than a few
bugs that impacted our customers. As a result, our developers would spend more
than ten hours per week working on fixes to Live Chat, at the expense of spending
time improving on our core helpdesk product.
310

The resources that Live Chat was eating up were massively disproportionate to
the benefit our customers and our business got from supporting it.

3) The Product Was Too Weak


As we considered and debated the future of the Live Chat app, we spent hours
testing competing products, including Olark, SnapEngage, LiveChat and others.
The reality was quickly pretty clear, and we realized what should have been
obvious from the start: the companies who focused 100% on building the best
chat product on the planet were doing it better than us.
Their products were more stable, more functional and simply superior to ours.
And in hindsight, of course they were. These companies live and breathe live chat
the same way that we live and breathe helpdesk software. If we compared Groove
to a clip-on helpdesk app from a company whos focused on something else, itd be
ridiculous if our product werent vastly superior.
The biggest benefit that our app had over competing chat apps was the seamless
integration with Groove.
But that also meant an untapped opportunity

4) The Opportunity Cost of Not Having Partners


Weve learned that integration partnerships are a huge driver of new customers
and awareness.
Our partnership with HipChat has led to customers adopting Groove that may
have never found us otherwise.
And when our developers looked into the competing products, we concluded that
theres no reason we cant make their integration with Groove as seamless as our
own Live Chat integration is now, only with a better chat product.
By choosing to keep Live Chat in-house, we were not only offering an inferior
product, but we were passing up the opportunity to build mutually beneficial
partnerships with some great companies.
While we certainly had an emotional tie to the Live Chat app, looking at the
evidence made it pretty hard to defend.
It was a tough decision, but in the end, we simply couldnt justify letting our
customers settle for an inferior chat experience, and letting ourselves settle for
passing up an opportunity to deliver more value through a partnership than we
could deliver on our own.
311

Letting Our Customers Know


When it comes to customer communication, there are few things I hate more than
getting emails that position obvious service cuts as across-the-board
enhancements.
Yes, these changes are often made to improve the business and in turn, to allow
the business to improve the value it delivers to the customer but painting cuts
as 100% positive is disingenuous at best.
I truly believe that this change is in the best interest of ALL Groove customers
(including Live Chat users), and I wanted that to be absolutely clear to them. But
the reality is that by doing this, we were disappointing some of our customers, and
we had to own up to that, too.
Heres the email we sent to all Groove customers on Monday:

Our Email To Customers

312

And yes, some customers were disappointed.

Disappointment

But I went back and forth with several upset customers, and nearly all of them
came around to seeing why we had to do what we did.
In fact, one trial user even signed up for a paying account after our exchange.

Coming Around

We also got more than a few emails from customers who were hugely supportive
of our decision.

Support

In the end, the backlash wasnt nearly as severe as we feared, and we were excited
to see so many customers support this change.
313

Moving Forward
Without a doubt, this change is a bummer to some.
But having a very clear 12-month goal makes our decision much easier.
If we want to help 5,000 businesses by the end of the year, we need to keep our
resources focused on on that goal.
Live Chat was not a good enough product for us, or for our customers. And as
much as it hurts to cut off a part of the app, we needed to.
So were going to leave chat to the companies that do it best, while we continue to
focus on building the best damn helpdesk on the planet.

How to Apply This to Your Business


Its hard to let go of features and products that you think make your product
better.
Really hard.
Sometimes, as in our case, the tie to that feature is emotional, and that can make
the veil over your eyes that much thicker.
But I hope youll take this opportunity to look very closely at every single feature
in your product.
Does it:
Live up to the standards youve set for your business?
Deliver more value to your customers than if they were using a competing
product for that feature?
Deliver more value to your business than the resources you spend to support
and maintain it?
Clearly have a direct impact on you meeting your goals as a business?
If the answer is no to any of those, it might be time to make some tough choices.

314

Six Months Later: Weve Given Away


More Than $50,000,000 in SaaS Apps
July 17, 2014

Six months ago, we launched the biggest


small business software giveaway ever.
Heres how things are going
What apps do you use to grow your business?
Its a question I get asked a lot.
In many ways, its not a great question. Or not the right first question for most
people, at least.
Its usually asked under a flawed assumption: that tools are the difference between
a struggling business and a successful one.
Its like thinking that the major difference between Lebron and a struggling rookie
is the shoes theyre wearing. Often, thats about the only thing they have in
common, and Lebron would still handily win a one-on-one game wearing hiking
boots.
We write a lot on this blog about the fundamentals of business, and how were
always looking to improve our own foundation.
We talk about the strategic development of our messaging and positioning.
We talk about the painstaking process we used to grow our blog from nothing.
315

We talk about the big wins that come from having hard conversations with
thousands of customers.
In those cases, tools arent the most important factor. Not even close.
But after and only after we adopted the mindset of fundamentals first, and
put in the hard work of developing those fundamentals, we found that the tools
we used did start making a difference.
For example, we work hard to drive traffic to our site. KISSmetrics makes it easier
for us to analyze that traffic and make decisions about what we need to change or
test.
Without the hard work, an analytics tool would be pretty useless.
But when combined with the foundation weve set, KISSmetrics makes our lives
much, much easier.

After Youve Done the Hard Work


Earlier this year, we realized something: a lot of the people who read this blog
have done the hard work.
Theyve set strong foundations, and theyre at the point where they could benefit
from using the same tools that the most successful startups use.
Thats why, in February, we launched the Small Business Stack.

The Small Business Stack

316

We wanted to make it easy for startups who were ready for powerful SaaS tools
but not quite ready to pay for them to get access to those tools.
We set a goal: help 5,000 startups and small businesses by the end of the year.
Now that were a bit past halfway through, heres where we stand

The Small Business Stack Stats


At launch, the Stack had 19 partners offering free or deeply discounted SaaS apps
worth more than $10,000.
Today, there are 37 industry-leading companies represented, offering more than
$20,000 in free software.
And with more than 400 companies asking to be featured, weve had to be very
selective in who we add.
We had to turn away some really cool businesses with valuable products that we
loved, simply because it wasnt the right fit for the startups and small businesses
we built the Stack for.
At the time this post was written, just over 2,900 people had signed up to unlock
the offers in the Stack.
The response has been overwhelmingly positive:

Tweets About The Stack

317

318

Its been awesome to watch, to say the least.

Whos New in the Small Business Stack


Our original class of 19 must-have apps set a damn high standard for the Stack:
Groove (90 Days Free)
KISSmetrics (90 Days Free)
Unbounce (75% Off for 3 Months)
Grasshopper ($50 Credit)
Moz (90 Days Free)
CrazyEgg (90 Days Free)
Drip (90 Days Free)
Wistia (90 Days Free)
Vero (90 Days Free)
Customer.io (90 Days Free)
Zapier (90 Days Free)
iDoneThis (15% Discount)
BidSketch (90 Days Free)
Mention (90 Days Free)
PipeDrive (90 Days Free)
ExitMonitor (90 Days Free)
PlanScope (90 Days Free)
Uncover (90 Days Free)
Stride (90 Days Free)
Every single one of those offers still remains a part of the Stack. Fortunately, weve
been able to keep that high standard for the newest wave of 18 must-have SaaS
apps:
Freshbooks (90 Days Free)
AnyPerk (30 Days Free)
Cyfe (90 Days Free)
Prefinery (90 Days Free)
Blossom (90 Days Free)
InVision (90 Days Free)
CoSchedule (120 Days Free)
Friendbuy (50% Discount for 90 Days After Trial)
AdEspresso (30% Discount)
3dcart (90 Days Free)
ProjectLocker (90 Days Free)
iubenda (50% Discount)
Workable (90 Days Free)
Evercontact (25% Discount On All Plans)
Close.io (90 Days Free)
319

(The three apps below are being added this week.)


Ghost.org (90 Days Free)
15five (90 Days Free)
Flow (90 Days Free)

Want $20,000 in Free SaaS Software?


We still want to help 5,000 businesses this year. were more than halfway there,
but we need your help to hit our goal.
If you havent yet, unlock the Small Business Stack now.
Once you enter your name and email address here, the form will ask you to share
the Small Business Stack via Twitter, Facebook or email. As soon as you do any one
of those, youll get instant access to all 37 offers.
Youll help yourself to $20,000 in free apps, and youll help us give away
$100,000,000 (!!!) in software to startups and small businesses in 2014.
Heres the link: www.groovehq.com/software-stack

One Small Request


I hardly ever ask for anything on this blog.
I write about our experiences and what we learn, and I hope that you learn from it
all, too.
Today, Ive got just one request for you:
If youve signed up for the Small Business Stack: Leave a comment and tell us about
your experience. What have you gotten out of it? Have any of the apps in
particular helped you grow?
If you havent signed up for the Small Business Stack: Leave a comment and tell us
why. Whats holding you back? What would get you to sign up? Any particular
apps youre looking for?
Thanks for helping us help other startups.

320

Why Investor Updates Are Important


(Even If You Dont Have Investors)
July 24, 2014

Every three months, I send an email to


Grooves small group of angel investors with
an update on our progress. Heres a behindthe-scenes look at how it helps us grow
We ran into a tiny technical issue last week.
Bullshit. It was NOT tiny. Not even a little.
A small outage brought us down for a bit.
Dude. Get real.
I mustve written, deleted and rewritten the sentence a half dozen times before I
got the truth out: the server outage (the same one from this post) was disastrous.
I was writing my quarterly investor update, and I had to tell them the truth the
whole truth about what happened.
But that didnt make it feel any less shitty.

321

These people believed in Groove enough to put their own money behind our
dream, and every time I share a fail with them, Im paralyzed by my fear of letting
them down.
Of course, sharing the wins feels amazing.
Over time, Ive developed a system for sending investor updates that keeps them
in the loop about Groove, maintains our strong relationships and helps us work
through business challenges.
In fact, Ive gotten so much from simply writing investor updates that Id force
myself to do them even if I didnt have investors.
More on that below

Four Reasons Why Frequent Investor


Updates Are Important
Why is regular investor communication such an important entrepreneurial habit?
There are four big reasons, one of which has nothing to do with investors:
1. The obvious one: it keeps investors in the loop. They want to know whats
going on with their investment, and they shouldnt have to ask.
2. It keeps your startup top of mind. That means that if you have problems that
youre asking for advice on, theyll be thinking about those problems. And if
you have (hiring/funding/networking) needs that youve asked them to help
you with, theyll be reminded to do that, too.
3. It shows that youre a communicative entrepreneur who respects their
contributions to your business. Not only is that simply the right way to treat
people, but it can be useful if you need to ask them for funding later, either
for your current business or the next one.
4. For me, I find that writing these every three months creates valuable
mileposts in the way I think about Groove. I reflect on our growth, think
about our strategy and evaluate the business at the 50,000-foot level. When
were in the trenches, that macro perspective often escapes us, and if I didnt
force myself to sit down and create these updates, I might not be so diligent
about stepping back and evaluating our growth this way.
Takeaway: Writing regular investor updates is critical for keeping up your investor
relationships, but its valuable even if you dont have investors. Itll give you a
birds-eye look at your business that many startup entrepreneurs I know struggle
to get.

How I Write Investor Updates


Heres an example of an update I sent earlier this year:

322

Example Investor Update

323

Frankly, I dont know if my approach is the best one out there, but it works for me.
The feedback I get from our investors is overwhelmingly positive and grateful for
the over-communication.
There are four elements to the email above that Id consider critical to any good
investor update. And while I don't organize my updates in sections this way, it's
how I think these updates through in my head:

324

1) Respect Their Time.


Much like with landing page design, youll have readers who want the full story,
and skimmers who just want the top-level details.
For that reason, I always lead with the big picture, and then break up the update
with bold headlines, lots of whitespace and clear, direct language. Its also worth
noting that I use the same exact order for the categories each time, so that those
who only want to see a specific section will know exactly where to scroll.
If Im making a particularly important or urgent ask, Ill make sure to bold and
emphasize it so that it cant be missed.

2) DDPN: Done, Doing, Planned & Numbers.


This is the core of every update I send:
What weve done since the last time investors heard from us.
What were doing right now to grow the business.
What weve got planned for the near-term.
And of course, the numbers: number of customers, churn, monthly recurring
revenue, monthly burn and cash on hand.

3) Other Wins, Fails and Needs.


Anything that doesnt fall under DDPN goes here:
Wins that wouldnt be covered under stuff weve done, including great PR hits
and growth milestones.
Important fails like downtime, major lost accounts or anything else that
might impact the health of the company.
Needs that stand in the way of achieving bigger, faster growth. This might
include hires you need to make, partnerships youd like to explore or any
other big strategic challenges you might be facing. This leads to

4) The Ask.
Hopefully, your investors bring more than money to the table.
If theyre passionate about helping your business grow, then theyre probably
happy to tap into their networks to help you solve your challenges. I almost always
ask for something at the end of each email. It might be something small like an
introduction, but it always helps us move toward our goals.

5) Above All, Be Totally, Uncompromisingly Honest. No B.S.


Ill admit, it can be really tempting, especially early on, to sugarcoat your
companys struggles.
I still have to work to overcome that temptation, like in the story at the beginning
of this post.
325

But every time, I remind myself that there are two huge problems with that:
First, any good investor will have been through the gauntlet, and will know how
businesses grow from nothing. There are a ton of challenges, and for a while you
may have more fails than wins to report. If you lie and pretend that everything is
always sunshine and roses, your investors will either know youre lying, or theyll
think youre delusional; neither is good.
Second, sugarcoating the bad stuff undermines the value that your investors can
bring to the table. If theyve been around the block before, chances are they might
have some solid advice for working through whatever it is youre facing now. Sure,
you dont have to take their advice, but skipping over your struggles means that
youll never have the chance to consider their advice in the first place.

How to Apply This to Your Business (Even if


You Dont Have Investors)
First of all, if your investors havent heard from you in a while, use the template
above to get them back into the loop. Theyll appreciate your update, and it just
could get you the advice or favor you need to break through whatever
challenge youre struggling with right now.
If you dont have investors, I still recommend going through the exercise of
writing a hypothetical investor update at least every three months.
As an entrepreneur, I get lost in the day-to-day hustle all the time, and Ive found
these updates to be immensely valuable for seeing the big picture of how your
business is really doing.
Whether you have investors or not, my hope is that by sharing my approach to
investor updates, I can help you evaluate your own business on a month-tomonth level, no matter what stage youre in.

326

The Value of the Hustle:


How We Saved $25,000 by
Thinking Outside the Box
July 31, 2014

As a startup, a lot of pricey products and


services can seem out of reach. Heres
how weve dealt with that challenge
Uhhhhh can you repeat that?
I had just finished a demo of a really slick marketing automation app.
It was the kind of app that I could definitely see us using and getting value from.
And thats when the founder of the company told me the monthly fee.
I thought I heard it wrong.
Its not that the cost was unreasonable. Thousands of companies pay it and
much more for the valuable product.
But in my lean-early-stage-startup mind (this was more than a year ago), the price
I was quoted was multiple times more than I was expecting, and there was no way
we could swing that kind of spend so early on.
I know Im not alone in this.
327

Ive talked to a lot of founders who get sticker shock when they hear the price of a
lot of business expenses. Not just for software, but for talent, events,
memberships, ads, everything.
Even Groove, at $15 per user per month, gets dozens of discount requests every
week.

Discount Requests

Im not saying that these things are overpriced. Im a big believer in paying for the
best people and products you can afford, as the payoff is often much greater than
skimping.
I am saying that these things are expensive. And often, they seem too expensive to
many startups and small businesses, especially in the early stages.
But what weve learned along the way, that too many founders dont know, is that
almost everything is negotiable.

Three Ways Weve Hustled Our Way to Huge


Savings and Extra Value
We dont discount our product. Not anymore, anyway.
And we dont expect discounts for valuable resources that are worth every penny
they cost.
328

But we do believe in mutually beneficial partnerships that help both companies


get real business value.

1) Leveraging Our Product


When I heard the price of the marketing app, I was surprised, but I wasnt done.
In fact, heres the exact email I sent to the sales rep that same afternoon:

A Simple Proposal

Within two hours, he responded: sure.


We still use and love the software today, and we still pay a deeply discounted price
for it.
Takeaway: Dont let price be a dealbreaker without exploring other options first. If
your product is just as valuable as the one youre trying to buy, a swap might work.

329

2) Leveraging Our Skills


About a year ago, we needed another designer for a growing number of tasks, but
we werent ready to hire someone full time.
None of the part-time designers we talked to seemed like a good fit, and we were
getting frustrated.
Eventually, I remembered that I had been introduced to the founder of an elite
design and development agency.
Their designers were incredible, but as I learned when I asked him, they were also
off-limits.
We dont rent out our designers, he told me (and rightfully so).
But in our conversations, I learned something else: the agency was trying to figure
out how to do content marketing and generate more leads.
As it turns out, were pretty good at content marketing.
So I made him an offer: wed share everything we know and help them get set up
with the right strategy, tools and approach something a top consultant would
charge many thousands of dollars to do in exchange for a few hours per week of
their designers time.
He readily agreed, and weve since gotten many thousands of dollars of designer
time because of the arrangement we made.
Takeaway: Dont limit yourself to only thinking about your business main product
or service as your trading leverage. You have other skills that youve had to learn
as youve grown your business, and those can be very valuable to others facing
similar challenges.

3) Leveraging Our Partners


Early on at Groove, there was yet another piece of business software that I wanted
to buy.
It was expensive (to us), but looking at the numbers, I figured that we could
probably make the spend work.
But before I pulled the trigger, I decided to see if I could use this opportunity to
help get even more value out of the deal (in a way that would also be fair and
valuable to our partner).

330

Sweetening The Deal

The sales rep responded right away that he would have to check with his CEO, but
ultimately, they agreed, and we ended up getting some great early exposure for
Groove.
Takeaway: Hustling isnt just for discounts. You can also often get more value out
of deals than you would have, simply by asking. Sometimes, the things you can get
might not have been available to you otherwise, but because youre already doing
business with your partner, theyre incentivized to work with you on what youre
asking for.

You Have More to Offer Than You Think


Lets say youre pre-launch, and dont have a product to offer yet.
Or your product isnt relevant to the person youre trying to strike a deal with.
This is where thinking outside of the box comes in handy.
Have you solved a unique business challenge that you can spend some time
helping your partner work through?
Have you built a unique automation or process to make things more faster that
you can share or help your partner implement?
Do you have readers or customers who might benefit from being exposed to your
potential partner?

331

On that note: never, ever, ever try to do the last one secretly. First of all, its probably
illegal. Second, its a betrayal of your readers/customers trust, and thats not worth
any amount of money. Weve never traded exposure on our blog or email list, but if
we ever did, wed either a) be upfront about it on the blog, and b) truly believe that
whatever were sharing can be of real, positive value for our audience.
Takeaway: Even if you dont have a product or service that would be interesting to
your potential partner, you still might have something non-obvious to offer. This
is where thinking outside the box pays off massively.

How to Apply This to Your Business


Ive been told no a lot, too. And that sucks.
But the value weve gotten out of hustling is worth a thousand nos.
You cant get everything by bartering, but youll never get anything by staying
quiet.
As with anything, you should practice always asking for what you want.
Think about everything you have to offer, and how it aligns with what your
partners might benefit from.
And always keep thinking about how you might be able to get more value for your
business by adding unconventional enhancements to your deals.
I hope that by sharing this, Ive helped you and other startups and small
businesses realize that theres almost always more than one way to pay for what
your business needs.

332

Feel Guilty About Taking a Vacation In


Your Startup? Heres Why We Dont.
August 7, 2014

Taking time off is critically important, but


its also a big challenge for fast-moving
startups. Heres how we make it work
Over two weeks in July, Groove signed up just over 40 new customers.
Our monthly revenue increased by about $1800.
We published two blog posts that each got shared just over 1,000 times.
It was a pretty standard two weeks, as far as Groove is concerned, except for one
detail: I put in about an hour of work, in total, over those two weeks. And most of
that hour was spent responding to blog comments.
And thats because I was on vacation, living the good life in Hawaii for my
honeymoon.
One thing I notice in a lot of conversations with startup friends (especially
founders) is that its impossible to talk about vacation time without talking about
the guilt that many of us feel when we think about taking time off.
What about all of the work that still needs to get done?
333

What about my team members who are going to be stuck without me?
In a startup, every second counts. Am I stealing from the company by going on
vacation?
Im not writing this post to brag about my own trip (though the waves at
Shipwrecks beach did make for some pretty epic surfing), but to highlight just
how important it is for the business that everyone on the team takes time off from
work, and how we make it work at Groove.

On Vacation

The Value of Shutting Off, and the Cost of


Always Being on
Our team takes burnout seriously.
We have to, since the last time we accidentally slipped into a routine of running
ourselves in the ground, our productivity crashed and we risked the future of the
company.
Weve long believed in the value of taking time away.
334

Personally, every time I get back from vacation, Im rested, rejuvenated, and really
excited to get back to work.
And when Im overworked, I feel stressed, tired and my decision-making suffers.
But its not just anecdotal.
Ernst & Young did a study that found that for every 10 additional hours of vacation
time their employees took, their performance ratings from supervisors improved
by 8 percent.

The Benefits Of Vacation

At the same time, overworking without breaks takes a huge toll on our health,
making us sick in all kinds of ways.
And it hurts companies, too. One study found that employees lack of sleep a
curse I fall victim to every time we start to work too much cost companies more
than $63 billion in productivity each year.
Takeaway: Theres no doubt about it: the dangers of not taking time off from work
massively outweigh the (diminishing) benefits of putting in those extra two weeks
every year. Its hard to remember to take time off, especially at startups, but its also
critical to your success as a business.

335

How we make it work as a small remote team


We all take time off from work we have to but that doesnt mean it doesnt
come with challenges.
The toughest thing about making vacations work in a small team is that we dont
have a lot of overlap in our roles; were all critical.
If our only designer leaves for a week, well, nothing is getting designed that week.
We cant simply step into each others shoes.
There are three things that weve found work best to ensure that vacations dont
end up bringing the company to a halt:

1) Building Vacation Time Into Our Roadmap


Realistic roadmapping is one of the biggest struggles for almost any startup.
Until your team has been working together for quite some time, almost everything
takes longer than you think it will. And thats with everyone working at full
productivity.
But when an employee goes on vacation or even has a sick day things can get
bad, fast.
One of the most important resource planning lessons weve learned is to budget
liberally for vacation time and sick days, so that they never come as a surprise.
Our weekly project plans look less ambitious than they did a year ago, but we hit
our milestones far more consistently.
Takeaway: Make sure that youre accounting for time off in your project planning.
Itll avoid painful stalls and missed milestones when team members get sick or go on
vacation.

2) Frontloading The Work


Another critical consideration: dont just budget for less work to get done when a
team member is gone.
You also need to budget for less work the week before a vacation, as the employee
will need to spend time doing work that minimizes the number of tasks that get
pushed onto teammates.
Take this blog, for example: generally, after a post is written, Ill work with our
designer to build the images and code the post. Then Ill write the email that gets

336

sent to our subscribers, load that into Campaign Monitor and queue it for sending.

Blog Workflow

Before I left, I spent extra time doing those tasks (and scheduling the email sends)
so that nobody else would have to. In fact, just about the only thing that nobody
else can do answer my emails and comments was all that was left to do during
the time I was away, and that was what I spent that hour of work doing.
With the work frontloaded and the right systems in place, the company still ran
with minimal disruption to everyone elses workflow.
Takeaway: Think about what needs to be done while youre away, and do your best to
minimize what gets left to your teammates. By doing the extra work up front, you let
the company run as seamlessly as possible without you.

3) Hiring the Right People


Ive talked a number of times about how important hiring the right people is,
especially for a remote team.
When it comes to handling workload and time off, having the right team is critical.
As a remote team, we cant babysit each other. So just as important as it is to hire
people who can be their own CEO and get their work done, its also important to
hire people who know how to manage their workload without getting overworked,
and who already deeply understand the benefits (for the whole team) of taking
time off.
337

If someone on the team cant handle the combination of remote autonomy and
startup craziness, theyll burn out fast. Burnouts lead to lost productivity and
stalled progress, and we all know where that leads.
Having the team on the same page with regard to vacation keeps us all
accountable, too.
When I made the mistake of checking in less than an hour after my vacation
started (Im only human), I was called out for it:

Oops

Its a funny example, but an important point: good teams know how valuable it is
for everyone to take the time to recharge.
Takeaway: Hiring the right people is important for so many reasons, but keeping
your team sane and healthy is a big one. Make sure new hires know how valuable
time off is, and how to manage their workload to ensure that they dont burn out.

How To Apply This To Your Business


It can be easy to feel like taking a vacation is robbing your team, and your
business, of valuable time and effort.
But in fact, the opposite is true: by not taking time off, youre stealing productivity
and creativity that could be moving the business forward.
Vacation doesnt have to mean a trip to Hawaii; it could be a camping trip, a week
in another city, or even time spent at home.
The only necessity is that you turn off, tune out and step away from your work.

338

How Sharing Feature Release Dates


Turned Us Into Liars
August 13, 2014

We used to share planned feature release


dates with our customers. Here's how
that ended up hurting us
I feel like you guys lied to me.
Ouch.
This one was going to be tough to explain.
Just two weeks before, a customer had emailed us. He was a new user, and was
having a bit of difficulty using Groove. His business had a pretty unique need that
our feature set didnt support yet.
But - we were working on a product update at that very moment an
enhancement to our Rich Text Editor that would solve his problem.
I was excited to share that with him, so when I heard about his issue, I checked in
with our developers about the status of the development.
We were almost finished, and right on schedule, with the release expected to be
ready in a week.
339

So thats what we told the customer.

A Dangerous Promise

Experienced product folks are shaking their heads right now, because we know
what happens next.
A week later, we hit a snag in the final stages of testing and find a series of nasty
bugs that render the update too unstable to release.
Because our small team has to balance that project with the everyday work of
maintaining the app, supporting our customers and fixing other critical issues, the
bugs take another week and half to diagnose and eliminate.
And while we kept our concerned customer and everyone else who had
requested the feature updated, it was clear that the episode didnt make us look
very good.
In fact, he was right. Even though it wasnt on purpose, we lied.
It wasnt the first time something like this had happened we shouldve known
better but having a customer call us out so directly was a big learning
experience for our whole team, and we certainly havent let it happen again.

Why We No Longer Share Release Dates


With Our Customers
This may sound obvious to some, or shady and deceptive to others, but in fact, the
opposite is true.
Let me explain.
When you share a release date, and it turns out to be wrong, you lose your
customers trust.
340

As product teams, we should know that unexpected issues happen quite often,
and that planned release dates arent always accurate. While we do our best to
plan our efforts well and forecast our progress accurately, things dont always go
the way we hope they do.
So if we promise a delivery date to our customers, even if we hit our milestones
more often than not which we do just one missed goal turns us into liars.
So by not sharing release dates, were being more honest the truth is, we dont
know exactly when the release will be than the alternative.
In business, a customers trust is what we work hardest to gain. Once you have it,
its easy to lose, and incredibly difficult to get back.
Were always working to get better at hitting our development milestones, and
frankly, weve gotten much better at it.
Still, we cant and wont risk letting down our customers by misleading them
on our feature roadmap. Its not just a development issue, but a communications
one.
Takeaway: Not sharing release dates may seem dishonest, but its not. In our case,
we know that we dont hit our milestones 100% of the time, so wed rather be
honest about not being able to perfectly predict the future, than use our goals to
make promises that we may be forced to break.

Three Steps Weve Taken to Solve This


Problem
1) No Product Announcements Until the Product Is Ready.
This is, by far, the easiest and best way to protect your business from accidentally
lying to your customers.
As startups, we run into a lot of obstacles. And unfortunately, theres often a lot of
bad news.
We cant build everything we want, and we cant fix everything we want to fix as
quickly as every customer wants us to fix it.
Some days, theres nothing we want more than to give a frustrated customer good
news; to tell them that their issue would be fixed tomorrow, or next week.
Its tempting, but its simply too risky. Thats why weve decided to never announce
new features until theyre staged and functioning well enough to release to our
customers.
341

Takeaway: As tempting as it is, dont announce anything until its ready. This one
simple rule can guarantee that youll never lie to your customers about release
dates.

2) Only Give Customers Info You Know to Be 100% True.


While we wont give release dates, we are honest and transparent about what
were working on.
We publish frequent development updates on our Better blog, and we do our best
to communicate to customers that were working hard to solve their issues, even if
we cant give them a specific time that itll be fixed.
As an example, this is what we recently told a customer whos running into a
problem thatll be solved by a feature currently in development:

A New Approach

I have no doubt that this approach costs us some customers with critical issues
who are on their way out the door.
And while theres nothing I hate more than having a customer leave it feels like a
punch in the gut, and it never, ever, ever gets easier Id rather lose them (and
potentially have them come back when we can better solve their problem) than
lose their trust and business forever.
Takeaway: Not sharing release dates doesnt mean that you cant and shouldnt
be completely honest and upfront about what your development team is working
on. You should still let customers know that youre working hard to help them.

3) Better Communications Between Development and Support.


Weve always focused on communication. As a remote team, you have to if you
want to have any hope of success.

342

But in this instance, there was a specific communication gap that we needed to fill
to solve this problem.
On our weekly team calls, weve started diving deeper into the development
roadmap not just that weeks to-dos, but how the future roadmap looks, and
whether or not its changed from the week before so that our whole team has a
better understanding of the features were working on and releasing.
And Mo, our head of customer support, has become very involved in our
development roadmap, spending quite a bit of time logging issues in Pivotal
Tracker so that the dev team always knows where the biggest customer pain
points and opportunities are. We recently shared that workflow on this blog.
Takeaway: This isnt just a customer communication issue, but a team
communication issue, too. Make sure that your developers and support team are
on the same page and supporting one another to help your customers in the most
thorough way they can.

How to Apply This to Your Business


If you hit your development milestones 100% of the time with zero unexpected
delays, and know for a fact that youll continue to do so forever, then you probably
dont need this advice.
But unfortunately, for most startups and small businesses, this simply isnt the
reality.
It can be tempting to try and keep a customer happy by promising them a solution
by a certain date, but dont do it.
If you turn out to be right, the customer is pleased.
If you turn out to be wrong, you may lose their trust forever.
As obvious as it seems, its an issue thatve been battling and we were finally forced
to face. Im glad we did, and I hope that our experience helps you do the same.

343

14 Ways Our Remote Team Stays Sane


Working From Home
August 21, 2014

Like most founders, I cant say that I


consider myself completely sane.
By the very nature of our jobs, were taking big risks, and our dreams are far
beyond what the data suggests we can reasonably expect.
To take that plunge, I think you have to be a little bit strange.
I have quirks, paralyzing fears and near-breakdowns, and many of the founders I
know do, too.
Thats all made worse by the fact that for most of my working hours, theres not a
single person in the physical space around me.
Were a remote team, so its something that everyone at Groove deals with.
For some including me working solo is the best way to go. Im still happier and
more productive than Ive ever been working from a shared office.
But still, the isolation can get to you.
Over the years, Ive become much better at spotting when the isolation is about to
get to me. And Ive developed a number of ways to stop it in its tracks.

344

In 3 years of working solo, heres what Ive found works best to help me stay sane
working from home:

1) Playing
I work hard. We all do.
So when I look out my window and see that the surf is looking particularly good
that day, I feel no guilt about taking my board to the beach for a couple of hours.

Taking a break

Its a welcome release, and doing something I love helps me get out of my work
head. More often than not, I come back to work refreshed, relaxed and ready to
tackle the next big task.

2) Walking the Dog


Working from home is absolutely NOT a good-enough reason to get a dog (or any
pet). Caring for a dog takes a lot of time and effort; everything people say about
dog ownership being a big commitment is true.
But I will say this: having a dog forces me to take daily breaks that I might not
otherwise take, and thats a very, very powerful benefit.
It gets me out of the house, and while I dont know if Id call my leisurely strolls
exercise, they certainly make me feel better.
345

The Honey Badger

3) Team Chat (Not Just for Work)


Were on Slack all day at Groove, and more than 95% of our teams communication
takes place there (with the other 5% being Screenhero and Skype).
Team chat is a huge asset to any remote team, but what many people dont talk
about is the social aspect of it. We have the water cooler conversations in our
Slack room that wed otherwise use for casual social interaction in an office, and
its a lot of fun.
It certainly helps us feel like were not always working.

346

The Water Cooler

4) Having Regular Calls (Even When You


Dont Have To)
To me, hearing another persons voice helps me feel like Im not the only one in
the room.
And while we have weekly team calls, and Im almost always on Skype with one or
more of our employees every day, sometimes thats not enough.
So I schedule calls to connect with other founders and startup folks. It helps me
build my network and learn from others, while giving me the benefit of actually
connecting with other people while I sit at home.
347

5) Sleeping Well
Theres been so much written about the value of sleep, and anecdotally, theres no
doubt in my mind that when I have a good nights sleep, Im happier and more
productive than when I dont.
I also know that when I spend all evening working, I sleep much worse than when
I give myself time to wind down and relax. Thats why I disconnect around 7PM:
disabling push notifications on my phone, closing my email client and stopping
myself from checking Twitter just because.

6) Listening to Music
Theres hardly a time when Im working that Pandora isnt on. Like many people I
know, having light background noise helps me focus, and its a lot more fun than
working in silence.

Working to music

348

Some of my favorite Pandora stations to work to are Van Morrison, Bob Marley,
Moby, Kings of Leon, Adele, Avett Brothers, Bruce Springsteen and Bon Iver.

7) Standing Desk
About two years ago, I switched to working from a standing desk.

Standing Desk

Aside from the health benefits which, in fairness, theres debate over I find
that it simply makes me move more. Im a lot more likely to pace, or walk to the
kitchen for a glass of water, than I would be if I were sitting comfortably. And
moving around helps me feel less closed in.

8) Sitting Desk
As much as I love my standing desk, I also love changing things up.
Every couple of days, I move my workspace over to the kitchen table.
The change of scenery stimulates me, and keeps my environment from feeling
stale.

349

Sitting desk

9) Exercise
Just like sleep, the benefits of exercise have been discussed ad nauseum.
What Ive found to be most is to pick something you actually enjoy; if you hate
running, why force yourself to run? Youll be less likely to make it a habit if you
dont look forward to it. Youre better off playing tennis or basketball or doing
something else that makes you happy.
I actually enjoy running, so thats usually what I go with.

10) Stretching
This is probably the simplest, easiest thing I do that helps me stay sane while
working from home.
Its also probably something that many people at offices feel less than comfortable
doing.
Every hour or so, I step back from my desk and spend five minutes doing
stretches. I like how it makes my body feel, but it also helps to have something
that keeps you from overworking by building breaks into your day.
350

I also asked the Groove team for their best working-solo advice, and got some great
tips:

11) Playtime With the Cats


Cats Domino and Gorilla

Mo: Like Alexs dog walking, I enjoy spending some quality cuddle time with my
own two furry coworkers: Cats Domino and Gorilla.
They are the best kind of coworkers in that they dont distract from getting deep
in the work zone when I need to put my head down and crank out tickets, but
always remind me when its time to take a brain break to chase a string or play
fetch with a stuffed mouse (yes, my cats fetch)

12) Meditating
Len: Meditation doesnt have to be a religious thing or a spiritual thing. For me, its
just a great way to step back and relax my brain for a few minutes. I use the
Headspace app, which has been absolutely amazing; for 10 minutes a day, it
teaches you how to meditate in 10 days.

351

Len With His Meditation Coach

13) Family Time


Jordan: With a two-year old son at home, a change of pace is never far away. My
breaks usually involve big trucks, blocks, and a giant sock monkey.

Family Time

352

14) Playing a Musical Instrument


Chris: I like to keep my saxophone or a guitar sitting close by for those times when
I need to clear my head. The really hard problems require whipping out some
early Metallica at full volume, more subtle issues will inspire some John Coltrane
on the sax. If its a really happy day, the neighbors (the local moose family) [Alex
note: Chris lives in the Colorado Rockies] might be tapping their hooves to Let it Go
from Frozen, even in winter. After all, the cold never bothered me anyway :-)

Jamming

How to Apply This to Your Life


Not all of these tips will be interesting or useful to you.
But it doesnt take 14 tips to make an impact. Pick 2-3 that you could see yourself
doing, and work on making them regular habits.
Whether you work from home or in an office, I hope this helps you feel better and
get through your day in a more productive and positive way.

353

Lessons Learned Building


a Startup Team
August 28, 2014

Building a team that works well together


isn't easy. Here's how we've approached
hiring at Groove
At first, it was just me.
I hired an engineering team at an agency to build Grooves beta product, and went
to work doing everything else: product spec, sales, marketing, QA, customer
support, research, project management, investor relations.
Then, it was Edmond and me. Edmond was a developer I hired to bring the app in
house after MojoTech was finished with it.
When youre a team of one or two, you dont worry about hiring. Every job is
yours, and you find a way to get it done, whether you know how to do it or not.
But eventually, with a ton of hustle and some good luck, you get a chance to grow.
We were fortunate in that regard, and it was soon time to figure out how to build
a small team.
Now, two years later, were a full-time team of six.

354

Granted, in the scheme of things, were still tiny.


In fact, people have asked me incredulously how we support so many customers
with so few employees. But if you think about it, its actually not crazy at all.
Take a company like Basecamp, which has 35 employees and supports more than
300,000 paying customers. Thats one employee for every 9,000+ customers.
Or Buffer, a 23-person team supporting nearly 700,000 users, at one employee
per 30,000+ customers.
Sure makes our 1-employee-per-333-customers seem like small potatoes.
But even building a tiny team, weve learned valuable lessons, made some
mistakes, and scored big wins to get to where we are.
So when I got this email from a reader

Hiring Question

I thought it would be helpful to share some of the lessons weve learned along the
way:

1) At First, Hire for Immediate Needs Only.


When we first started, Groove needed to accomplish two things: make a product,
and get it into peoples hands.
For better or worse, we werent too worried about accounting, legal filings,
operations or HR. Yet.
355

So we focused on hiring people who could help us accomplish our two main goals.
I wasnt looking for anyone that could be trained to do a great job tomorrow (more
on how thats changed below), but instead I wanted people who had the skills and
experience to get us closer to where we wanted to go today.
At the time, we were working on transitioning our development from MojoTech,
the agency who built our first iteration. We needed developers who could deeply
understand the existing codebase and build the features we wanted to build
immediately.

An Old Job Posting

So my first hire was Edmund, a full-stack developer, and a bit later, Chris, a backend engineer.
Not long after that, I hired Jordan, another full-stack developer.
While Edmund had to take off for personal reasons, Jordan and Chris are still part
of our team today.
Takeaway: When youre starting out, dont worry about who youll need in six
months or a year. Focus on getting the people who can create progress today.

2) Once Tomorrow Is Secure, Hire for the Future.


Early on, we didnt really have the luxury of planning for next month, let alone
next year.
But when we turned a corner and hit Product/Market Fit, Groove began to grow
fast. We were hitting the milestones on our product roadmap, and building at a
good pace.
We had the runway to plan for the future, and so our hiring changed a bit to
reflect that.
356

In general, the approach weve taken is this: its time to hire for a position when
the pain of not having that person on your team is bigger than the cost of adding
them.
Heres an example: In our first year, I was pounding the pavement, selling Groove
to anyone who would listen. Over time, the need for a customer support person
became more and more pressing. I couldnt continue doing all of the support and
marketing at the same time.
Thats when I hired Adam, one of my childhood best friends, to join us as our Head
of Customer Success.
Takeaway: After you turn a corner and have the benefit of being able to think
months and years ahead, thats when you should start to make the hires that
will help you achieve the goals youre setting out.

3) Turnover Will Happen. It Wont Be as Bad as You Think.


Several months ago, Adam left Groove to return to the finance world.
It was a smart move; he has a new baby, and needed more stability and income
than a startup could provide.
When he told me he was leaving, I couldnt help but panic.
Its not that I expected him to stay forever; in fact, early on, we had talked about
this being a temporary arrangement while we got the company off of the ground.
But over two years of working together, we not I had become Groove.
When your company is two, three, four, five or six people people who battle in
the trenches together every single day it can be hard to envision the business
without those team members. Thinking about losing them can be a tough shock to
the system.
Plus, theres always the fear: what will people think? Our customers talk to Adam
every day, are they going to be upset that hes gone? Will everyone think were in
trouble because our first employee is leaving?
As a founder with many fears, it can be paralyzing.
But, as with most things, it never ends up being as bad as you think itll be.
Adam was gracious to give us more than a months notice, and helped us find and
357

train Mo, our new Head of Customer Success, whos been an amazing addition to
our team (our customers agree).

Alive and Well

(For anyone interested, Adam is still one of my best friends.)


Takeaway: Losing a team member is scary for a startup, but it wont end up being
nearly as bad as you fear. Try to make the most of their final weeks and have them
help you train their replacement. Either way, life and business goes on.

4) Supplement With Part-time Help.


Not every need requires a full-time effort to fill.
Theres a lot of resistance among founders Ive talked to when it comes to hiring
part-time help. They say things like we want someone whos going to be part of
the team, and end up hiring full-time employees to fill part-time needs.
It doesnt have to be all-or-nothing.
358

Along our journey, Ive supplemented the Groove team with part time help, and its
allowed us to stay lean as we grow. In fact, we still use a part-time designer for the
header art on this blog.
Its also opened up big opportunities for us: sometimes, the people you want on
your team arent necessarily available for a full-time gig.
Len, our head of marketing, was consulting for a number of companies when he
first joined us to work part-time with copy and messaging. Over time, hes helped
us with content strategy, messaging and copy for our site redesign. It wasnt until
two years later that the stars aligned and he wrapped up his other projects to
come join our team full-time.
A bit of a teaser: Lens hiring also has a lot to do with Lesson 3 above, as hes going
to be heading up a new blog were excited to announce soon and helping us to
double down on content.

Coming Soon

Serg, our front-end developer, started out working just a few hours per week,
helping us to code our blog posts. Now, several months later, hes a big part of the
team, coding everything from our marketing site to our app UI.
Takeaway: Dont be afraid to lean on part-time help. If you dont need a full-time
employee, it can save you money. If you are looking for a full-time solution, it can
plug the gap while you search. And often, it can end up becoming a full-time
arrangement in the future.

359

5) Reduce the Risk for Everyone.


A bad hire is always costly. For a startup, it can be devastating.
When I say bad hire, Im not referring to the person youre hiring. Im referring to
the decision to hire someone thats not the right fit for your team, and then the
passive decision to keep them there.
Its a mistake thats burned me in the past, and I was determined not to let it
happen with Groove.
Thats why we use the trial-to-hire method: every new employee joins us for a
trial project something they can do during nights and weekends while keeping
their current job of 2-4 weeks. After the project is done although usually, its
apparent much sooner we can evaluate whether were the best fit for each
other.

Our Hiring Process

This approach has helped us slowly but effectively build a team that works and
fits well together.
Takeaway: Hiring someone is a big investment, and can be risky for both parties.
Interviews can only tell you so much. Use trials to make sure that every new team
member fits in well.
360

6) Dont Be Too Slow to Spot a Poor Fit.


There are few management cliches more often-repeated than hire fast, fire
faster.
And while I dont necessarily agree with the first part (we hire pretty carefully and
methodically), I know that I could use some help internalizing the second part.
Sometimes, you make mistakes.
You hire people, and it doesnt work out. Maybe theyre not a great fit for the team.
Maybe their strengths arent what you thought they would be. Maybe you
misjudged the need for a full-time person in their position.
Whatever it is, these mistakes can be very costly.
Heres the problem: a person is not an app. Regardless of whether you have a payas-you-go contract with them or not, cutting ties with and employee is a much
more difficult and emotional act than canceling an app subscription.
In my entire career, Ive had to fire dozens of people. People with families and
responsibilities. Its devastating, and over the years, it hasnt gotten any easier.
If anything, its gotten harder, as I get angry with myself for continuing to make
hiring mistakes from time to time, costing people their jobs.
But at the end of the day, keeping an employee who isnt a good fit for the team
can be crippling.
It brings down the whole team, and ties up cash you could be using for better
investments in your business.
Its tempting to try and make it work; to brainstorm and try to figure out ways to
make the fit better.
But Ive never been good enough to do that successfully.
One of the things Ive learned and worked on a lot over the past year is being
much faster to spot whether a new team member is a good fit or not.
It takes some unpleasant brutal honesty with yourself, but in the long run, its
critical to your business future.
Takeaway: Firing people is hard. Really hard. But if you want to hire and manage a
successful team, you need to learn how to determine whether or not someone is
going to be a strong part of your teams makeup in the long term, and if the
answer is no, you need to take action as soon as you can.
361

How to apply this to your business


I dont know if this is the best way to build a startup team.
But its certainly worked well for us.
If youre at a crossroads with hiring and thinking about how to move forward, I
hope that our experiences can help shine some light on one possible approach.
Id also be interested to hear about your own hiring lessons learned: just leave a
note in the comments below.

362

The Power of Testimonials


(And How We Get Great Ones)
September 4, 2014

One of the best ways to connect with


prospects is by using stories from existing
customers. Heres how we do that

Its frustrating, infuriating and agonizing at the same time.


Every startup with a big competitor knows this battle: when youre the little guy,
youre not the safe choice.

363

Youre the risk. Youre the one that has to scrap harder to get picked.
That saying, nobody ever got fired for hiring IBM?
In our world, nobody ever got fired for signing up for Zendesk.
When something as critical as customer support is on the line, people want to
know that they can trust the company theyre hiring. They want to know that our
product will work for them, specifically.
And if they choose Zendesk, its often because there are tens of thousands of
others just like them using Zendesk, too. It sure makes the decision a lot easier to
justify.
We cant fault prospects for that: Ill almost always take the safe choice, too.
The challenge, then, is: how does the scrappy, unproven startup become more of a
sure thing?
While were always learning and we still have a long way to go, weve gotten pretty
good at making that case over the last couple of years, and one of the things thats
helped us the most is using testimonials to help prospects overcome those
uncertainty objections.

The Power of Testimonials


Its no secret: people tend to follow others like them.
Marketers call it social proof: when we see lots of others doing something, we
assume that thats the correct behavior.
There have been dozens of studies on social proof. This is one of my favorites, in
which a psychologist placed people standing on a sidewalk staring up at a
building, and observed hundreds of passerby stopping to stare up when they saw
his actors, too.
But social proof is only one side of it.
How many times have we been like the people at the beginning of this post?
When we see a product that looks like it works well, we sometimes think: great,
but it probably wont work for me because Im (insert any unique trait or condition
here).
We build objections to any marketing pitch we see, and testimonials help to
364

overcome those by showing us that yes, this product does work for people just like
us.

What IS that?

Takeaway: The psychology of testimonials is deep and powerful, and lies on two
important pillars: social proof and overcoming the objection that your product
wont work for a particular customer.

What Makes a Good Testimonial?


At Groove, weve found that good testimonials increase conversions by up to 15%
on our homepage, guest post landing pages and email marketing.
Whats a good testimonial?
Hint: its not a fluffy, gushing Groove is amazing and changed my life statement.
Its much more nuanced than that.
I encourage everyone to read Sean DSouzas two-part Copyblogger series on The
Secret Life of Testimonials (Part One and Part Two), but what weve found is that
the best-testing testimonials are specific about who the testimonial writer is, and
what problem Groove solved for them.

365

Example Mini-Testimonial

The first part helps the reader put themselves in the shoes of the testimonial
writer. As a SaaS founder, Im a lot more likely to relate, for example, to Allan
Branch, another SaaS founder, than the anonymous John S., Boston, MA that I
see offering up testimonials all over the web.
The second part, specificity about a problem, demonstrates to the reader not just
that your product is generally good (thats not enough), but that you can solve
their problem.
In the example above, one of the most pressing problems weve found in our
customer development is that enterprise help desk users feel bogged down by the
complexity of the software, so we need to make sure we hit that pain point in our
testimonials.
Takeaway: Good testimonials arent fluffy; they communicate very specifically the
type of person the testimonial writer is and the type of problem theyve been able
to overcome. This helps readers put themselves in the storytellers shoes.

366

How We Get Good Testimonials


Unfortunately, its not as simple as saying could you please provide a
testimonial?
Sure, thatll get you a testimonial, but itll probably be a weak, generic and cannedsounding blurb that wont help you any more than not having testimonials.
But weve found that while its not that simple, it is fairly straightforward to get
good testimonials by following a few basic approaches.
Note: in all of the examples below, we never post a testimonial without first asking
the customer for permission.

1) Capturing Objections
Every single person who signs up for Groove gets this email:

Youre In Email

Its not just amazingly valuable for collecting qualitative data about the
conversion triggers that worked in getting people to sign up, but it gives us
profound insight into the objections and obstacles people had to overcome to
make the choice to sign up for Groove.

367

Objections and Challenges

(Alex note: the person who sent that email above has now been a customer for six
months).
Often well go back in a few weeks or months and follow up with customers to see
how theyre doing. Using those stories (customers who went from big challenges
to being successful using Groove) in our testimonials helps us connect deeply with
prospects going through the same emotions.
Takeaway: Good testimonials dont just capture the end result. They capture the
struggles and objections at the beginning, too.

2) Listening to Customers
If youve been following the blog, you know that we spend a lot of time talking to
our customers.
Mo, our head of support, does it for 8+ hours per day. The rest of our team
engages with customers, too. I devote at least a quarter of my time to talking to
Groove customers.
(In fact, one of my goals for the next few months is to talk to every single one of
our customers about their experiences and how we can improve.)
And while the goal of our conversations is always to help the customer do better
with Groove, weve also learned to listen for the underlying stories they share
about their experiences.
Its usually in these natural conversations and not the canned requests for
testimonials that we get the best, most compelling customer stories.
Once the conversation is over or the support issue is resolved, well go back and
ask the customer if we can share their story.
368

Underlying Stories

Takeaway: There are a lot of important reasons to always be talking with your
customers. Being able to spot and extract powerful testimonials is just one of
them.

3) The Straight Ask


Sometimes, customers dont necessarily need to talk to you; theyre doing just fine
on their own.
And if theyre busy, it can be hard to get them on the phone with you.
But if we know someone is succeeding with Groove and that their story might
make a great testimonial, well send them an email that looks like this:

Testimonial Request

369

Notice how we dont just ask for a testimonial, but walk them through the steps
required to hit the most important traits of a great testimonial.
The script above is yours to use as youd like; I hope it nets you some powerful
stories.
Takeaway: The way you ask for a testimonial can mean the difference between a
crappy testimonial and an amazing one. It takes a bit more work, but its worth
doing right.

How to Apply This to Your Business


Testimonials can be a powerful tool, and if youre not already using them, I hope
this post inspires you to test them in your marketing.
If you are using them, but your testimonials arent as good as they could be this
is almost always the case, as were also always working to improve our customer
stories I hope youll revisit them now.
Feel free to use the scripts and strategies above to tell better stories, connect
more deeply with your prospects and improve your conversions.

370

How Ive Become A Better Founder By


Practicing Patience
September 11, 2014

Move fast and break stuff is a startup


mantra. Heres a different take on things
This doesnt work.
The first email came a few minutes after we pushed it live.
Looks like its broken for me.
The widget isnt showing up on our site.
How do I turn it on?
Two years ago, we released an updated version of our (now-discontinued) live
chat app.
Within half an hour, our support mailbox was flooded with complaints about bugs
and technical issues.
It wasnt ready. And there was nobody to blame but me.
In the never-ending battle to balance our teams time with the list of high-priority
tasks we needed to accomplish, I had gotten impatient with our weeks-long effort
to get this new version of live chat in our customers hands.
371

It seemed to work fine for me, and despite our developers recommendations that
we spend more time testing, I made the call: Lets just get this out there.
The ensuing mess cost us more than $10,000 in lost productivity as we worked to
answer emails and pulled the app down to fix it. Worse, it cost us the trust of
customers who had taken a chance on a young startup, believing that we would
reward their risk with a product that worked the way we said it would.
It was a painful but important lesson for me: patience is one of the most valuable
skills to develop as an entrepreneur.

The Power of Patience in Business


Theres plenty of research that supports the value of patience.
A number of studies have shown that people who are patient tend to be more
healthy, happy and successful.
Anecdotally, I know that impatience has a negative impact on my mood, and more
importantly, my ability to make decisions.
When Im feeling impatient, Im more impulsive. If were building something that
Ive been antsy to release for weeks, and the only thing standing between us and
going live is a bit of polish, its tempting to say fuck it and push the feature out.
Sometimes, that can be a good thing. Weve used the lean approach to many of our
releases in the past, and its helped us get early feedback and make fast
improvements.
But its not always useful to just ship it.
With marketing, you dont get a second chance. We spend many hours on every
blog post, every email, every piece of copy, to make them as good as we possibly
can.
The same is often true with UX changes, especially those that impact the
onboarding experience. New customers arent as forgiving as those who have been
with you for years, and delivering a less-than-perfect experience can easily be the
difference between retention and churn.
And as I recounted at the beginning of this post, shipping too early has hurt us
badly in the past.
Shipping something before its ready can be dangerous, but Im human, and
impatience can and sometimes does still get the best of me. Its been a tough
372

lesson to learn over the years, but I know that actively working on developing
patience has made me a better entrepreneur.

Four Ways Ive Built and Continue


to Build Patience
1) Being Honest About the Consequences
I cant count the number of times Ive said: We need to get this out by Friday.

Tick Tock

But of those times, I can only recall a few where I was able to follow that
statement up with because
We often set arbitrary deadlines, and that can be a very good thing for keeping
ourselves motivated and productive.
But things arent always in our control, and external factors can cause us to miss
those deadlines.
Heres the thing: I cant think of a single time where missing a deadline has had a
long-term, negative impact on our business. I can think of multiple times where
shipping a buggy or unpolished feature has hurt us. Id much rather do the former
than the latter.

373

Im not advocating laziness, or a casual attitude toward deadlines. We hustle hard


every single day, and we work overtime to hit deadlines when we need to.
But there are times when a deadline isnt absolute, and when we and our
customers benefit from me being a little bit more patient and taking a bit more
time to get things right.
Takeaway: Deadlines are a valuable tool for productivity, but if youre not going to
hit your deadline, be honest with yourself: are you better off shipping something
thats not quite done? In many cases, for us, that answer has been no.

2) Taking Lessons From Other Areas of Life


As a Rhode Island boy, Ive been surfing since I was 15 years old.

Patience on the water

Funny thing about the ocean: it doesnt give a damn about your schedule.
Ive waited hours for a good wave.
Ive waited hours and gone home disappointed that a good wave never came.
Ive waited hours and been rewarded with 10 seconds of pure bliss that put me in
an amazing mood for days.
When I was younger, surfing taught me patience, and that the wait for a great
wave pays off in spades.

374

As I got older and busier, I had less time to spend on the beach, and didnt get to
appreciate that constant, unavoidable reminder of the value of patience.
At Groove, Ive forced myself to make a little more time for play, and surfing is a
big part of that.
And every time Im out there at Ruggles, I re-learn a valuable lesson that I can
instantly apply to my work.
Takeaway: Many hobbies take patience to learn and get good at, but even though
weve developed that patience, we dont think to apply it to our business lives.
Being more aware of how patience helps you in all areas of life can help you
become a more patient person at work, too.

3) Not Measuring Against Someone Elses Yardstick


Its ridiculously easy to look at a competitor and think, They released [Feature X]
last week. We need to build it NOW!
There are multiple reasons why that attitude is a poor way to make product
choices, but its a tough thought to avoid. I know Im guilty of it.
Theres a quote that I love, though Ive seen it attributed to so many different
people that I have no idea whos ultimately responsible for it: Never compare your
beginning to someone elses middle.
My natural impulse is to measure my progress against people who are more
successful than I am, and who have been at this game for far longer.
And while thats a great driver for motivation, its a terrible way to build patience.
We often see the end result (e.g., a competitor releasing a specific feature), but not
the amount of work that went into achieving that result (the many weeks they
spent building and testing that feature). Trying to shortcut our way to achieving
that result is a great way to guarantee that well never be as good as the people
were competing against.
Takeaway: Dont let other peoples progress make you lose sight of your own path.
Comparing your beginning to someone elses middle can be a quick path to losing
patience and falling behind.

4) Track and Celebrate Little Wins


When you spend weeks working towards a goal, its easy to think of the results as
binary: either we accomplished that goal, or we didnt.
But that, for me, is a dangerous mindset, because if we dont hit our deadline, then
375

the binary perspective makes our whole project a failure, even if we had a number
of smaller wins during the process.
Ive found it immensely valuable to break down every project into smaller microgoals to help us track those smaller wins.
For example, we finished our last website redesign a few days late.
But along the way, we tracked a number of small wins that made our business
stronger:

Small wins along the way

Having the progress be so visible makes it easier to be patient about the ultimate
result, and seeing the little wins helps motivate our team to keep hustling.
Takeaway: Dont think of your deadlines as pass/fail only. Remember to track and
celebrate the little wins along the way. Itll make you more patient and productive.

How to Apply This to Your Business


Patience is one of the toughest skills to develop, yet one of the most valuable
assets Ive built as an entrepreneur.
Its not always a tool youll want to use: there are situations where overtime, a bit
of extra hustle, and putting pressure on the people around you to move faster are
necessary.
376

But for me, and for the sustainable growth of our business, Ive found that those
situations are better off as the exceptions, and not the rule.
I hope that these techniques help you develop the patience to wait when you need
to, and to ultimately make better decisions for your business.

377

Why Were Doubling Down on Content


(Plus, a Big Announcement)
September 18, 2014

Weve decided to make a big change to


our marketing strategy. Heres why, and
how were going to do it
I couldnt believe it.
There we were, eight months after publishing our first post on this blog, and
everything had changed.
The Groove team was on our weekly call, and we were reviewing the previous
months numbers.
Now, were far from a success story, and as a founder, part of my job is never being
satisfied with where we are, but it was unmistakable: things were looking pretty
good.
And it was (almost) all thanks to this very blog.
To be sure, it wasnt a magic bullet. There is no magic bullet.
It was months and months of hard work, committing many hours each week to
producing the very best content we possibly could. It was grueling, and it cost us a
lot of opportunities to attack other growth strategies.
378

But it certainly paid off.


So when it came time to talk about how we were going to develop a strategy to
meet our 12-month goals, one choice, among many, was obvious

Five Big Wins From Content Marketing


Ive said this before, but its worth noting for anyone thinking about their own
business growth: content marketing has been, without a close second, our most
effective strategy for growing Groove.
Weve grown our:

1) Traffic
Theres no question that the blog has delivered huge traffic for us.
The numbers speak for themselves, and dont really need much of an explanation.
Heres a look at our numbers back in April of last year, before we started taking
blogging seriously:

Trac a year ago

And again this April, a year later:

379

Trac today

2) Thought Leadership
When we started, virtually nobody knew who Groove was.

Thought Leadership

380

Now, I get almost daily emails with interview and speaking requests, and bloggers
asking for info about Groove that they can feature in their content.
The thought leadership weve built through the blog has scored us many
thousands of dollars of free PR.

3) Trial Signups
As our traffic grew, our trial signups grew, too.
Heres a snapshot from a 7-day period last April:

Signups a year ago

And another one from a year later:

Signups today

381

4) Community
The community that lives in our blog comments is an active and passionate one.
We have folks from every corner of the world who come to participate on every
post, sharing their own insights and reflections on whatever were discussing that
week.
Weve gotten some powerful advice from commenters that has given us new ideas
for our own growth efforts.

Ideas from the community

5) Bottom Line
The most important benefit of all: the blog has helped us go from $28,525 in
monthly recurring revenue to more than $81,000 as of this week.
Thats nearly triple the revenue, and its all organic: no ads, no promotions,
nothing but careful planning, hustle and persistence.

Where This Blog Falls Short


To be sure, this blog has been amazing for our business.
And we have no plans at all to take our foot off of the gas here.
But as weve grown the blog, one interesting challenge has become very clear.

382

Thousands of businesses now know about Groove.


Thats a very good thing.
Many of them, unfortunately, still dont know what we do.
Thats not so good.
One recent blog post described us as a CRM company:

Ouch.

When I read that, I couldnt help but wince.


And while its always the responsibility of the writer to get their facts right, I
couldnt blame them, because it was our fault.
Weve done very little on this blog to get people to think of Groove as a customer
support company.
So as we look to double down on content, the natural direction for us to go seems
very clear.
Except

Weve Tried This Before (And Failed)


Back in April, we introduced the Customer Support Academy.
For a while, we published weekly support tips, sharing the strategies weve used
to deliver better customer support.
Eight weeks later, we had a whopping 500 subscribers.
But thats not the bad part. If we only had a handful of subscribers, but great
content, Id be fine with it, because Id know that we have the experience and skills
we need to grow our blog to success.
What made us abandon the blog after two months was a simple, but painful truth:
we werent proud of it.
383

It was an inexcusable, shameful half-assed effort.


Our posts were short, shallow and less-than-interesting.

Not good enough.

384

The blog had no name or voice behind it. With the $100K blog, I didnt have time to
write a second blog, so the support blog was a sloppily cobbled together team
effort from all of us.
We didnt employ any of the influencer engagement strategies that we knew
worked.
Thinking back, the decision not to promote it was probably subconscious, as we
werent creating content that we were excited to share with the world.
The blog had no heart, and the shitty results made that clear. We didnt succeed
because we didnt deserve to.
This blog is successful because each week, we work hard to earn our right into
peoples inboxes, reading lists and Twitter feeds.
Looking back, theres no way we could say the same about the Support Academy.

This Time, Were Swinging for the Fences.


This new blog hasnt been a few days in the making, or a few weeks.
Weve been working for months to put together actionable, useful and interesting
content to help startups and small businesses get better at customer support, and
understand how to use it to grow their bottom line.
Were investing our time and resources in high-quality content, art and
promotion.
The new blog also has a new voice: Len, our new content marketer, is heading up
the support blog.
Its his baby, and hes going to be giving the blog the time and attention that it
deserves, but that I dont have.
Im thrilled with the content hes put together, and Im confident that its going to
be a valuable resource for anyone interested in building better relationships with
their customers.
Well be publishing new posts every Wednesday, and also trying new types of
content that we havent explored on this blog. For one thing, weve got some
incredible guest content lined up from top entrepreneurs and support experts. If
youre interested in contributing, email Len (Len at groovehq.com).
I hope youll go read the first post, and let us know what you think in the
comments.
385

Well be taking every piece of feedback seriously, and appreciate your help as we
get this new effort off of the ground.

Introducing the NEW Groove Support Blog

To read the first post, click here: What Is Good Customer Service? Three
Principles for Getting Customers for Life.

How to Apply This to Your Business


Will this work?
I have no idea.
But were not doing it half-heartedly this time. Were taking the same approach
that worked on this blog, and putting everything weve got behind building the
best customer support blog on the planet.
If anything, I hope youll learn from our failure: if youre going to try anything, it
makes no sense to half-ass it.
Releasing anything that sucks doesnt count as testing. The results you get from a
poor effort tell you nothing about the results youd get if you did something right.
Go big or go home.

386

How We Got 2,000+ Customers by


Doing Things That Didnt Scale
September 25, 2014

Some of our growth tactics will never


scale. Heres why were okay with that
I could tell you what were doing, but it wouldnt help you.
When I was getting ready to launch Groove, I spent a lot of time talking to other
founders. And I would almost always start with the wrong question:
What are you guys doing for user acquisition?
Sometimes, theyd play along and clue me in to what they were up to.
Invariably, they were the types of things that help later-stage companies become
very successful: referrals, upselling, advertising. The spectrum was huge, and I was
a little overwhelmed, though planning on trying everything I could.
Until finally, one founder graciously called me out.
Look, I could tell you what were doing, but it wouldnt help you. We have 10,000
customers. You have zero. You need to focus on your first five customers.
He went on to share some of the things that he did when they were working to get
their first handful of users.

387

I hadnt heard anything like it in my other conversations.


They scrapped, clawed and fought hard for every single customer in their early
days. The founder would spend many hours with every single customer, learning,
coaching and making sure that they had a positive experience.
None of it was scaleable, but it didnt matter. Without it, he told me, theyd never
get the chance to scale.
That chat changed the way I thought about growth.
By now, nearly everyone in the startup space has read Paul Grahams brilliant
essay, Do Things That Dont Scale. And if you havent, you absolutely should. He
shares some great examples of things that now-successful startups did to get
customers in their early days; tactics that would never work for a larger, highvolume business.
Weve also done a number of things at Groove that are far from scaleable. We now
have 2,000+ companies signed up, but our growth approach has been to get one
customer at a time.
Below are six of the most valuable non-scaleable growth tactics weve used to get
customers for Groove:

1) Youre In Email
Ive mentioned this before, but one of our biggest onboarding wins has come from
our Youre In email.

388

The insights weve gotten early on from the responses to that email have been
game-changing.
Weve been able to transform our messaging based on what we learned is most
important to new customers, and weve been able to build deeper relationships
with those customers by helping them with whatever unique goals or challenges
drove them to sign up.
I still read and act on every single response I get.
Takeaway: Learning why new customers decided to sign up is incredibly valuable.
It informs your marketing and makes your customers experiences better. This is a
lot easier with a handful of customers than with many.

2) Customer Development
Earlier this month, I sent an email to our customers:

A Request

389

Over the years, theres nothing thats been more valuable for us as a growth tool
than one on one conversations with our customers.
And over the next few months, Im blocking off hundreds of hours of time to talk
to every single one of them.
I had nearly 30 of these calls last week, and this isnt the first time weve done this.
Ive already gotten some feedback that were using to improve the product.
At 2,000 customers, me talking to all of them is probably crazy. At 5,000, its
practically impossible.
Takeaway: Early on, theres nothing you can do thatll inform your strategy better
than talking to your customers. Theres no other way to deeply understand their
challenges, and get a true sense for their experience with your product.

3) Content Promotion
When we first launched this blog, we built our audience one influencer at a time.
I spent many, many hours emailing people and building relationships to help us
get our content into peoples hands.
Theres no doubt in my mind that it was worth it.

Worth It

And now, with our new customer support blog, Im at it again, emailing just about
everyone I know.
390

Len, whos writing the support blog, is doing the same.


The early results look good, but theyre also stalling just about everything else that
Len and I need to be doing on a day-to-day basis at Groove.
Still, were not going to slow down.
Takeaway: Content promotion is one of the most time-consuming and nonscaleable efforts we do, but the results speak for themselves.

4) Community Engagement
More than once, people have told me that they were surprised that I respond to
every comment on this blog.
Sometimes it takes me a little while, but I think its important. When people take
the time to read what we publish, and post a thoughtful comment about it, I cant
imagine not acknowledging that.
And more than that, its helped me build great relationships with some of the
readers of this blog. Some of those commenters have turned into customers
precisely because I engage with them.

The Value of Engagement

We get anywhere from 40 to 200 comments on any given post, so it can certainly
be a time-consuming task.
If and when the blog grows and that number doubles or triples, Im honestly not
sure how Ill possibly be able to keep up.
But for now, Im not worrying about that.
Takeaway: Ive gotten massive value from engaging with the readers of this blog,
and I suggest that every founder who blogs does the same.

391

5) Onboarding/Nurturing
A couple of weeks ago, James Altucher published as always a deep and
introspective post about a entrepreneurs event that he went to.
In it, he mentions a point that Joey Coleman made in his talk:
Joeys point was very simple: he had THE 100-day RULE.
If you hand-hold the client for 100 days, thats all you need to do.
Then they are your client for life. FOR LIFE.
As I read that, I couldnt help but nod my head in agreement.
Weve found a similar trend to hold true at Groove; when we hold our customers
hands for the first two months, theyre far, far more likely to stay with us after that
time.
So during the first two months of a customers time with us, its everyones job to
make that customer happy.
Now, thats not to say that customers are forgotten about after that.
Generally, after that time, we see support requests drop off naturally, so theres
less of a need for the all-hands-on-deck approach. But in the early days, its
critical.
On top of our regular support, our developers will jump in and help with any
technical questions, and Ill almost always be involved in support during that time
window.
Obviously, I wouldnt be able to do that so easily if we quadrupled our customer
base.
But for now, Im thrilled to be able to.
Takeaway: Getting your customers to wow might be a time- and teamconsuming effort, but until your product is established enough to speak for itself,
theres no way around it.

6) Scrapping
A while ago, I stumbled on this blog post:

392

Help Desk Comparison

In the post, Tyler put together a detailed comparison of Groove, Helpscout,


Zendesk and Desk.
I was happy about the mention, and then I saw

The Decision

Right away, I emailed Tyler.


Heres the thing: his rundown and his decision were totally sharp and wellreasoned. I respected his decision to go with Help Scout, and I wasnt emailing him
just to change his mind.
393

I wanted to learn more about his experience with Groove, and what we could do
better to start winning that battle.
We went back and forth for a bit, and I was grateful that Tyler was so open about
sharing his thoughts. Fortunately, the bugs that cost us Tylers business the first
time around had been fixed, so I asked him if hed be willing to give us another
chance.
A few weeks later, he published this update to the post:

Tyler Returns

Is scrapping for every one that got away a scalable approach? Absolutely not. But
it helped us win a happy customer early on, and to me, theres no question that
thats worth it.
Takeaway: When youre an early-stage startup, youll lose a lot of customers
because you dont have everything worked out yet. When you do work things out,
those lost customers might come back, and its worth fighting for every single
one.

How to Apply This to Your Business


Ive talked to a lot of early-stage founders who are struggling to get customers.
Many of them are taking the long view. That is, trying to use acquisition
strategies that theyll be able to use when they have 500, 1,000, 5,000 or 20,000
customers.

394

The trouble is, this approach hardly ever works.


Startup growth isnt as linear or neat as wed like to think, and there are a lot of
very valuable things you can do early on that definitely wont work later. And thats
okay, because theres a good chance that without those early battles, you wont get
a later.
And while I cant guarantee that the non-scaleable tactics that worked for us will
work for you, I hope that youll try at least some of them.
Or at the very least, I hope that youll be convinced to give non-scaleable growth a
shot.

395

We Deleted Our Facebook Page.


Heres Why.
October 2, 2014

There are lots of tactics youre


supposed to use. Heres why thats
dangerous
Screw it. Lets just delete the thing.
Something felt odd about saying that.
Like we were about to break the rules.
But the more we discussed it, the more obvious the choice became: our company
Facebook account had to go.
There were two major factors that drove the call:

1) Frankly, It Was Embarrassing.


We have more than 2,000 customers, 20,000 blog subscribers and many
thousands of unique visitors each week. And yet Groove had just under 200
Likes on Facebook.
Not really something I want people searching for us on Facebook to see.

396

197 Likes

2) It Was a Waste of Time for Us.


Now, Im NOT saying that Facebook is a waste of time for businesses. Many
companies use Facebook very successfully to grow.
But we were spending an hour or so each week updating the page. Obviously, we
werent getting any results.

No Results

397

And when we spent time discussing it and thinking about why we were doing it in
the first place, the answer was simple, straightforward, and just as embarrassing as
our Like count.
We were on Facebook because everybody else was. It was what we were
supposed to be doing.
And thats just not good enough.

Using Time Wisely


Like most other startups and small businesses, we have limited resources.
So when we got together to build our 12-month growth strategy, the question
wasnt what are the things we could be doing?
The question was what efforts would be the highest and best use of every team
members time?
That is, what can we do that will drive the biggest growth for Groove?
For example, we know that blogging helps us grow, because we track the numbers
carefully.

The ROI of Blogging

On the other hand, we cant tie our Facebook efforts to any revenue at all.
398

Every hour that we spend managing the Facebook page is an hour that we could
spend building the blog. An hour each week may seem insignificant, but thats 52
hours in a year.
The amount of traffic and signups we could get by spending 52 more hours on the
blog is significant.
And yet, we were robbing the blog of 52 hours of added time because of our blind,
knee-jerk tendency to do what we were supposed to.
Takeaway: It can be surprising to learn how much time youre wasting without
even knowing it. It certainly was for us. Do the math and figure out the
opportunity cost of doing things that dont work.

Three Things We Dont Do That Were


Supposed To
There are dozens probably hundreds of tactics out there that one expert or
another will claim as being a must-do for every business.
And so, so many businesses do those things. Thats why its so hard, on a mental
level, to wrap our heads around the fact that often, most of those tactics probably
arent that useful to us.
Its something Ive struggled with a lot.
As metrics-driven as I like to think we are, its tough to pull away from doing the
things we think were supposed to be doing. Id be lying if I said I didnt feel a little
bit guilty deleting the Facebook page.
But in the end, its a win for the thing that matters most: the performance of the
business.
Facebook isnt the only must-do tactic that weve dropped over the past few
months:

1) Networking Events
Early on, a lot of people told me that I needed to get out there and build
relationships, and that the best way to do that was by going to networking events.
I found that while the first part was absolutely 100% true, the latter was not. I met
some interesting folks at events, but of the most high-value relationships I have,
zero of them started at networking events.

399

2) Conferences
Having a booth with your logo on it at a conference like DreamForce or South By
Southwest is almost considered a rite of passage for growing tech startups.
While its nice to see your name up there, weve experimented with trade shows,
and theyve never driven the sorts of high-quality leads that we get from our other
efforts. Plus, they cost a lot more time and money.

3) PR
When we launched, we had put quite a bit of time and effort into building
relationships with journalists, and it did pay off.

Press

As it does for many businesses, getting mentioned in a high-profile publication


drove traffic and got us a big handful of signups.
But as we grew, the return on the PR traffic splashes began to lessen. The signups
were often of lower quality, churning faster than users who signed up via the blog
or other channels. Eventually, we pulled the plug.

400

I think its important to note something here, because I can picture the angry
comments were going to get from social media consultants and event organizers.
The above isnt a list of growth strategies that dont work.
In fact, almost the opposite is true: theyve worked so well for some people that
theyve somehow been added to a sacred list of things that every startup must be
doing.
Weve consciously decided not to do those things, and its helped us. What works
for others may be different.
Takeaway: Dont let must-do lists dictate the way you use your time. Instead, run
tests, figure out what actually works for you, and focus as many of your resources
as you can on those winners.

Our Three Focus Tactics Today


There are tactics were focusing as many of our resources as possible right now.
In fact, every so often, someone will comment on how much time we spend on the
blog.

Making Time

But just as I believe in cutting mercilessly when it comes to non-performing


tactics, I believe in making massive amounts of time available to do the things that
work. Fortunately, with enough work on the former goal, the latter becomes
easier.
While there are other things were working on, these are the three big focus
tactics that were giving a disproportionate amount of our resources to today:

1) Blogging
It may seem crazy to spend more than 20% of my time on it, but the ROI of this
blog speaks for itself. And thats the reason were doubling down on content, too.

401

2) Customer Development
Weve gotten such high returns from talking to our customers one-on-one that
Im dedicating hundreds of hours over the next few months to having customer
conversations. Again, it may sound like a ridiculous amount of time, but if anything
is important enough, well all make time for it.

3) Metrics
Next week, Ill publish a post that dives deep into how we used core metrics to
change the way we run our business, and transformed our growth as a result. That
never would have happened if I hadnt pulled one of our engineers off of product
development for more than a week to set up a thorough tracking system.
Takeaway: Dont be scared of spending too much time on something, as long as
theres a payoff. Theres no good guideline for how much time to spend on tactics
X, Y and Z, because theres no business that operates exactly like yours.

How to Apply This to Your Business


I hesitated to publish the actual lists of tactics that we do and dont use, because I
think that theyre secondary to and possibly distracting from the main
takeaway of this post.
In the end, I kept them because I think they serve as helpful examples, but I hope
that what youll take away is this: your time is far too precious (and failure nearly
always too near) to spend even an hour of it spinning your wheels.
Doing things that dont work isnt a bad thing on its own. In fact, its the only way
we grow and find what actually does work.
But doing things that dont work over and over again, simply because you think
youre supposed to be doing them, is actively and aggressively damaging to your
business.
Not too long ago, I needed a reminder of that. I hope that my reminder is helpful
to you, too.

402

Customer Development for Startups:


What I Learned Talking to 500
Customers in 4 Weeks
October 9, 2014

I recently spent more than 100 hours


talking to Groove customers.
Heres what I learned
In some movies, top military commanders have red phones that they only pick up
when things start to go wrong.
Theyll usually see that an issue is getting out of hand, and theyll grab the phone
(without dialing, of course), yelling something dramatic like get me the President!
While I have no idea if this emergency phone exists, I do believe that something
similar exists for startup founders.
When your core metrics start to lag behind your goals in our case, I wasnt
happy to see churn creeping up close to 3% as our customer base grew theres a
lot you can do to start to right the ship.
You can, and should, dig deep into your metrics to spot the weak points. You can,
and should, ask the smart people around you for advice. You can, and should, test
new tactics and approaches to improve.
But the hypothetical red phone that always seems to help us the most connects
directly to our customers.
403

In the very early days, we spent many hours talking to every single one of our
customers. We didnt have a choice; exhaustive feedback was the only way to
make our product good enough to reach Product/Market Fit.
And weve continued to believe strongly in the power of qualitative research; weve
done a ton of it, from collecting feedback in onboarding emails to Qualaroo
widgets to Net Promoter Score surveys.
But it had been a while since I dove in to hardcore customer development
interviews. In-depth one-on-one conversations to help us understand the
experience of our users like no survey ever could.
And with a core metric slipping too far for comfort, it was time to pick up the red
phone again.

How I Had 500 Customer Conversations in


Four Weeks
On September 10th, I sent this email to every Groove customer:

The Ask

404

The response blew me away. I expected a couple hundred people to write back
over the following week, but my inbox quickly began to fill.

Uh oh.

There was no way Id be able to schedule all of these without drowning under a
heap of back-and-forth emails. Scrambling, I signed up for a Doodle account,
which let me send a link to people who were willing to chat, giving them the
chance to schedule their call at a time that worked for them.

Doodle

405

Slots quickly began to fill up (I had to go back and add more spots four times).
While I only asked for ten minutes, I booked the calls in 30-minute blocks just in
case they went long, and to give myself some breathing room to compile notes
and digest each call afterwards.
I used Skype or my cell phone for the calls, Join.me for screen shares to walk
through Groove with the customers when I needed to, and old-school paper and
pen for taking notes.
I compiled data in a simple Google Spreadsheet, which you can find and copy
here.

The Tools

In all, I ended up spending more than 100 hours over four weeks on customer
development calls, which are still ongoing. When I shared this with a founder
friend of mine, he asked a fair, and obvious, question: why didnt I have someone
else do it, or split the calls with other team members?
Heres the thing: I trust my team members tremendously. I dont hire fast I only
hire people after I know I can rely on them to be a valuable asset to our company
and a great fit for our team. Its certainly not that I dont trust anyone on my team
enough to do customer development.
Its just that I consider customer development to be such a core part of building a
company, that its simply the CEOs job at this stage. Its just as important as
making strategy decisions or meeting with investors.
Plus, talking to customers isnt the same as reading the answers someone else
recorded on a spreadsheet. I wanted to feel and internalize our customers
perspectives so that they could drive the other decisions I need to make.
406

And thats why I tackled it on my own.


Takeaway: You dont need many tools to talk to your customers. And while its a
time-consuming task, its one of the highest-ROI efforts you can tackle as a
startup CEO.

What Questions Did I Ask?


I considered using a scripted series of survey questions, but ultimately decided
against it.
I wanted raw, off-the-cuff insights into how our customers think and feel about
Groove not how they think about specific questions regarding the features and
elements that we think are important. I didnt want to influence any of the
feedback I got with leading questions.
Instead, at the beginning of each call, I simply said:
Hey, thanks so much for agreeing to chat. I wont take too much of
your time. The conversations Ive been having with customers have
been invaluable in helping us shape the product and our plans for
the future, so Im excited to get your feedback.
My goal is to get an overall feel of how youre using the app, what
you like, what you dont like, and what we can do to make it better.
Ill let you take the floor.
Usually, the very first thing that people told me turned out to be the most
important part of their user experience, from their perspective. And often, those
important elements didnt line up at all with what I had assumed people would say.
There were more than a few surprises, including bugs we didnt know existed,
minor (to us) features that turned out to be hugely valuable for some users, and
use cases for Groove that we had never considered.
Takeaway: There isnt necessarily one right way to structure the conversations,
but there is a clear wrong way: influencing your customers feedback with leading
questions wont get you the results youre looking for.

7 Big Wins From Talking to 500 of Our


Customers
The ultimate win from customer development is deep insights into how our
customers think, feel and use our app. That insight is absolutely critical to the

407

growth of any business, and its the biggest reason I took this project on. It had an
immediate impact on how we approach our product roadmap and day-to-day
decisions.
Even if there were no other benefits, that benefit one alone would make it
worthwhile.
With that said, there were quite a few more big wins that ended up coming about
from the effort

1) We Learned That We Need Better Second-Tier Onboarding.


In more than a few of the calls, customers would mention particular challenges
they faced that could be solved with new features or functionality. Thing is,
sometimes they were features we already had; for example, third-party app
integration (when looking at support tickets, users can choose to bring in data
about their customers from other apps like Stripe and CRM tools). When I showed
them the feature, Id hear a painful but valuable reaction:
Wow! I didnt know that existed.
To me, thats a clear sign that we need to improve our onboarding as users get
more deeply engaged with Groove so that they can better discover some of the
more advanced features. Weve already updated our onboarding email sequence to
address this, and are working on building the guidance into the app.

2) We Turned Unhappy Customers Into Happy Customers.


I was able to repair a handful of relationships with customers who were unhappy
with the product. In once case, a customer wrote me an email criticising Groove.

Not Happy

408

I responded:

The Ask

I was a bit surprised when he agreed to get on the phone with me, but once he
did, I explained that I wanted to understand why he felt the way he did, and what
we could do to make it better.
As it turned out, he was upset about the lack of a couple of features that we had
planned to build in the immediate weeks ahead. When I shared that with him, he
quickly warmed up, and hes now a much happier customer.
Note: its important to be honest here. No product is perfect, and there are parts of
Groove that we wish were better. Those are the parts were working on. But never
try to convince a customer that a shitty part of your app doesnt actually suck.
Youll lose their trust in a heartbeat.

3) We Better Understood the Personas of Our Customer Base (With


Some Surprises).
Weve always had (tested) assumptions about the personas of our customers. And
many of them held true in these conversations. But as weve grown, things sure
have changed.
I learned about several new use cases for Groove that I hadnt considered before.
For example, several of our customers are schools that use Groove to offer IT
support to students and faculty.

409

For some of the newly discovered personas, there were enough examples that
weve decided to build case studies to try and attract more users that fit those
personas, or at least test the market to see if theres a strong fit.

4) We Built Better Relationships With Hundreds of Customers.


This benefit cant be understated enough: the number of positive reactions, even
from customers who complained about bugs or issues, was huge. Surprisingly, I
heard from many of our customers that no other businesses that they used were
doing this, and that the gesture of asking them for their thoughts not just with a
mass-emailed survey, but by reaching out for a one-on-one conversation meant
a lot to them.
Its amazing how easy it is to stand out with a bit of effort.

5) We Got the Chance for Some Quick Customer WOWs.


Sometimes, things that bugged customers were easy fixes or updates that they
had never reached out to tell us about. For example, one customer told me that
about an issue they were having CCing people from a certain domain. This was a
weird bug, but something we could fix in just a few minutes, and we ended up
pushing a fix for her issue that night.
Her response?

Customer WOW

An easy win that helped us delight a valuable customer.

6) We Learned How to Improve Our Marketing Copy.


Were always working to improve the way we position and write about Groove (see
our landing page design post for more). Hearing our customers talk about the app

410

and its benefits, along with their personal stories, challenges and goals, is the only
way we can write marketing copy that actually connects.
Talking to our customers is the only way to talk like our customers talk.
While I heard a lot of phrases that I was very familiar with already (Zendesk was
just too complicated, for example), I also spotted some new trends that youll see
on our marketing site very soon.

7) We Got Great Feedback Even When We Didnt Get to Chat.


Some customers couldnt or wouldnt get on the phone with me. And I
completely understand; theres nothing more valuable than time, and its a huge
ask to disrupt someones day, even if for a few minutes, to talk about a product
they use.
But while there were those I couldnt schedule talks with, many customers chose
to email me their thoughts instead.

Email Feedback

These were, in many cases, just as valuable as the conversations I had.

411

How to Act on Customer Development


Feedback
The feedback you get from customer development, just like any data, is useless if
you dont act on it. In fact, its worse than useless, since you wasted no small
amount of hours collecting it.
So to ensure that we got value out of this exercise, here are the steps weve taken
and are still taking to make use of the feedback weve gathered:

Step 1: Organize Feedback to Help You Spot Trends


After each conversation, I added labels (e.g., Search, Mailbox, Support, Automation,
Pricing) to capture the most important things covered in each conversation.

Organization

This has helped us go through the data and see which topics trended throughout
the conversations, so we know what customers are most vocal about.

Step 2: Process the Data


Once things were organized, it was easier to go through and decide how to act on
various trends. Core fixes and feature requests that bubbled to the top were
added to the roadmap. More ancillary features or less popular ones that had
potential were added to our wishlist for future releases; well continue to collect
data on these requests.

Step 3: Line Up Customer Case Studies


In my conversations, I unearthed quite a few customers who were having a lot of
success with Groove, as well as (like I mentioned) new personas that we hadnt
been targeting before. Those are both great candidates for new case studies to
412

feature as example of Grooves value, and weve already reached out to several of
these customers to make it happen.

Step 4: Send Thank You Emails


If a customer takes time out of their day to give you feedback on their app, its a
gift. They have a thousand other better uses (from their perspective) of their time.
So thanking them is important.
Ive always appreciated a thank you more when it was personal and made me feel
like my contribution was valuable, so I try to do that with my own thank-yous.
Each thank you notes included a brief recap of our conversation, along with any
action Im taking because of it, if any.

Thank you.

Step 5: Write About the Experience


This one is pretty meta, Ill admit.
But as hopeful as I am that sharing my experience will be for you, its also
incredibly valuable for me, giving me a chance to reflect on the results and
importance of customer development. As Ive researched this post, Ive caught a
number of things that I missed the first time I looked at my notes.

Step 6: Make It a Habit


Weve now added a call to action for a customer development chat into our
onboarding emails for every new customer.
Thankfully, itll be a lot easier to schedule calls one at a time than 2,000 at a time.

413

Talking to every customer.

How to Apply This to Your Business


Getting qualitative feedback isnt a tactic. Its a way of doing business that startups
need to live and breathe.
There are dozens of ways to get qualitative feedback from your customers:
Surveys
Net Promoter Surveys
Emails
Live Chat
And we use all of those strategies. But none has been quite as mindblowingly
valuable as actually taking the time to talk to our customers. It has changed our
product, our business and the way we think. Its certainly been responsible for any
growth weve had.
You dont have to go on a mission to talk to every single customer. But reach out
to a handful today. You might learn something that will change your business.

414

How We Got Over Our Fear of SEO


and Improved Conversions 20%
in the Process
October 16, 2014

I used to think of SEO as a scammy


strategy for startups. Heres
why I changed my mind.
This is a post about being wrong.
About totally misjudging something, and waiting too long to try it because of
preconceived notions.
And about how finally digging into the potential value of doing SEO right
convinced me that it was worth pursuing.
If youre in the same boat that is, curious about SEO but not really sure where to
start or why then this post is for you.

Three Reasons We Didnt Do Any SEO Before


There are a number of reasons we hadnt given much thought to SEO in the past.
Looking back, some of them were completely valid, and others totally misguided

415

1) Focus
Our team is big on focus. We believe in optimizing our time to spend it on the
things that we know will drive results, and cutting mercilessly in the areas that
dont bring much of a return.
Thats why we deleted our Facebook page last month.

Focus

Things were already going well, and in a world where were spending hundreds of
team hours per week on product, blogging, content promotion, support and
customer development, we didnt really have the capacity to shift focus to SEO.
At least, I didnt think we did.

2) Lack of Knowledge
Ive started four businesses, and grew them all without even thinking about SEO.
I dont say that to brag; I say that to explain that SEO simply isnt something Ive
come across in my career. Its not something Ive ever worried about.
Because of that, I knew next to nothing about it until I hired Jordan, our CTO, a
self-taught search marketer who has successfully used SEO and SEM in his own
416

businesses since 2000. Jordan has led the charge and taught our team a lot about
doing SEO right, but before that, I didnt really know much about it.
Which leads me to

3) SEO Is Scammy
I have no doubt that Im going to piss off some SEO experts by saying this.
But frankly probably because I didnt know anything about it before last year, I
had the pre-existing notion that SEO was not a whole lot more than a scammy
tactic to game Google.
My experiences with SEO mostly consisted of:
Struggling to finish reading blog posts and company websites that were
obviously built to house keywords, and not interesting content.
Seeing (and deleting) posts with generic comments and links back to business
sites on this blog, every single week.

(Note: I actually dont mind people linking to their business on our blog at all.
If youre adding value to our community, Im all about spreading the good
word. Its those who dont even take the time to read or contribute before
spamming us with their links that I cant stand.)
Getting pitch after pitch from offshore SEO agencies offering to write
keyword-optimized articles and submit them to hundreds of sites around the
web.

417

Unfortunately, this was a case of only seeing the bad side and assuming the worst.
And even more unfortunately, that ignorance was costing us traffic.

Why We Decided to Optimize Our Website


We first began to consider the idea of optimizing our marketing site for Google
when we did our last redesign. And while we didnt do it then, I was warming up to
the idea.
The more I read about real SEO and not the scammy stuff I had come across
the more I began to see the real value in taking this on.
Some of the resources I found invaluable were:
Neil Patels SEO: A Comprehensive Guide for Beginners.
David Zhengs guest post on OkDork, How We Grew OkDork 200% With These
Exact SEO Tips.
Brian Clarks How To Create Compelling Content That Ranks Well In Search
Engines.
The Adaptive SEO Approach by Yomar Lopez on the Unbounce blog.
Finally, I looked at our own conversion numbers, and what I found sealed the deal.
Visitors from external sources were signing up at a rate of 2.9%.

Conversions: External Sources

Traffic from the blog was converting at just over 5%.

418

Conversions: Blog

But traffic from organic search? A whopping 9.4%.

Conversions: Organic Search

A new goal became clear: we needed to increase our search traffic.

419

Our Strategy: How We Built a Solid SEO


Foundation
I want to be very clear: this is NOT an expert-level plan for SEO.
This isnt even an intermediate list of the things that you could do.
This is how we, as a startup that was doing literally nothing for SEO, began to
build a foundation to increase organic search traffic to our marketing site.
If youre an SEO expert, this will be very basic. But if youre interested in taking the
first steps and seeing how we got awesome results from a simple process then
read on to see what we did.

Step 1: Identify the Problem


We had a single-page marketing site that, while converting reasonably well, wasnt
doing us any favors in search engines. In a crowded space, we were often falling
onto the third, fourth or fifth page for searches relevant to our customers.

Falling Behind

Takeaway: While our site was doing well when it came to conversions, we were
leaving money on the table with a single-page design by not giving search engines
anything to pick up.

Step 2: See What Prospects Are Searching for


We had a bit of a head start here, as we had done similar research for a small
AdWords test last year. But essentially, we used Googles Keyword Planner to
check how frequently people were searching hundreds of different terms (and
variations of those terms).
420

Google Keyword Planner

For some of the terms, we simply guessed, but for many, we used records from my
customer development conversations, which continued to pay off. As it turned
out, many of the challenges and goals our customers described to me were highquality targeted keywords for us.
We also used Keyword Tool, which generates a list of Googles autocomplete
suggestions for any search, to find long-tail keywords that people were searching
for.

Keyword Tool

421

This research also proved to be invaluable for the strategy of our new customer
service blog, which we were building at around the same time. Ill dive much more
deeply into the development of that blog in a future post.
Takeaway: Keyword research is a get your hands dirty process, but well worth it.
Try to think like your customers, or better yet, actually talk to your customers to
learn how they think. There are tools to make this easier.

Step 3: Plan the Sitemap


We ignored any keyword that had many tens of thousands of searches per month
(e.g., customer service), and did our best to focus on smaller to medium sized
terms (a few thousand searches per month).
Why?
Because ranking for a term like help desk software would not only be a huge
uphill climb for us, but it would hardly yield the most targeted prospects (there
are many, many people who search for customer service who will never buy
customer service software).
On the other hand, the smaller keywords (e.g., help desk for saas startup), while
they didnt have nearly as many searches, would yield far, far more targeted leads.
Plus, by focusing on 100 smaller terms rather than one or two big ones, we would
diversify our targeting so that the success of our site wouldnt be dependant on
the fluctuating interest in a single term.
We took our list of keywords and began to build the sitemap. Our goal was to
create enough pages so that we could target the most important keywords, but to
stop before we began creating duplicate content; something that, aside from
damaging the visitor experience, is a sign of those scammy tactics and an instant
turn-off when I see it on a marketing site.
We housed our map in a simple Google Spreadsheet to help us keep track of
which keywords wed need to hit for each page, along with titles and meta
descriptions.

422

Each page had one or two primary keywords, along with long-tail keywords that
we used to capture hyper-targeted searches. We would try to make sure that our
primary keywords were included across the headers for each page.
Takeaway: There are a number of guidelines and best practices for building a
sitemap, but it comes down to picking the most high-value keywords and building
content that people will want to read.

Step 4: Wireframe
We built simple wireframes for each page. Complete enough to give us some idea
of what kind of copy wed need, but basic enough that the copy could still take the
stage without worrying about where it would fit.

Wireframes

Takeaway: Were big believers in copy first design, so while we mocked up basic
wireframes, we left ourselves plenty of room to let the copy be the star.

Step 5: Copy
Even though the goal of this effort was to improve our SEO, our keywords still
came second in our copy.
We were sensitive to our fear of our site moving away from the customer-friendly
messaging we have and losing our voice at the expense of trying to force
keywords into our copy.

423

So first, we focused on doing all of the things we learned how to do in our first
redesign. We used language from our customer development interviews and tried
to talk like our customers do. We hit pain points, goals, and important benefits;
including many of the ones we knew were successful from tests on our existing
site.
And while we had the keywords in mind as we developed the copy, we didnt
worry about whether or not we checked them off along the way.
Only after we were happy with the way everything read did we look at ways to
incorporate:
Primary keywords into headers
Secondary keywords into subheads
Long-tail keywords into copy
In addition, anywhere we linked to other pages within the site, we would try to
include the primary keywords for the linked page around the hyperlink.

Optimizing Links

In the end, we were satisfied that we were able to maintain our voice and tone
while improving the copy.
Takeaway: By writing interesting, quality content first, we were able to
incorporate our keywords afterwards and still maintain messaging that resonates
with our customers.

424

Step 6: Design
After putting the pieces together, we were left with a site that looked and felt
good enough to launch.

Final Design

425

Our friends at Less Films also created an awesome product video for the

426

homepage that incorporated everything wed learned since the first time we made
a Groove video. The making of the video was an in-depth and fascinating process
with tons of research and background work involved, and Ill definitely be writing
about the experience here in the future.

Takeaway: Our total time from start to finish was just a few weeks. A simple
design process let us ship a solid site quickly and iterate from there.

The Results
Its early, but the results have been promising.
A week after launch, we were ranking on the front page for a number of our
targeted terms.

427

And with the lift from organic search, overall conversions were boosted, too.

Note: these results might not be typical. Weve spent more than a year building
this blog, and our site has quite a bit of SEO power because of the number of links
that it gets. But with time, you can do exactly the same.

How to Apply This to Your Business


Weve still got a long way to go. And plenty left to do when it comes to fortifying
our SEO strategy.
But by just taking a few simple steps, weve managed to get some very exciting
results.
As I said, this isnt an advanced, or even intermediate strategy. In fact, theres a
good chance that you know more about SEO than I do.
This is meant to serve as a basic primer for businesses who were in the same
position as us: afraid and unaware of how to actually do SEO right without
becoming those people.
If you havent started doing any SEO because you dont know where to start, then I
hope this post has inspired you to give it a try.
It was certainly worth it for us.

428

Metrics Are NOT the Only Thing That


Matters in a Startup
October 23, 2014

Startup folks (myself included) love


talking about being data-driven. Heres
why thats dangerous
That number is the ONLY thing your team should be thinking about.
The speaker, a growth hacker giving a talk at a startup event I went to a couple
of months ago, was referring to monthly growth rate, a core metric used by many
startups (including Groove) to measure the health of the company.
I agreed that focusing on metrics was important, but something about the delivery
didnt sit right with me.
Since then, Ive been paying more attention to what people have been saying when
they talk about metrics, and to be honest, it concerns me.
I keep seeing things like:
Metrics are all that matters.
The one thing you need to do is be data-driven.

429

Keep a laser focus on your numbers.


Even Paul Graham a brilliant guy who I have nothing but admiration and respect
for suggests the same:

Its beautifully put and a great way to simplify growth, but in my experience, thats
exactly the problem: things are never that simple.

First, an Admission
I completely appreciate the irony of writing a blog post criticizing metrics, when
we work so hard to be data-driven at Groove.
We track numbers obsessively, run A/B tests constantly and set aggressive goals
for growth.
Hell, this entire blog is built around our journey toward a very specific metric.

But that only tells half of the story.


430

Where Performance Metrics and


KPIs Fall Short
Several months ago, we were growing at a steady clip, and then we had a single
week where things seemed to screech to a halt.

Yikes.

We hit a wall, and signed up only five customers over the entire week.
We had no idea what caused it, and digging into our metrics didnt help. But I
definitely lost sleep trying.
The following week, things were more or less back to normal.
Growth charts are rarely as smooth as the ones you see from runaway success
stories.
While weve grown consistently since reaching product/market fit, there have
been peaks and valleys.
And those valleys crippling troughs so deep they left us wondering if the
company was even worth pursuing wouldve killed us if we let them.

431

Not that common.

Grooves growth

Its important to track your metrics, but theres an important point that I think
most data-obsessives miss:
432

Never tie your value as a team and an entrepreneur to those numbers. You are
not your metrics.

You are not your metrics

Thinking that metrics are the only thing that matters in a startup will absolutely
crush you. That sort of approach works for robots, but were humans. We think
and feel, and when the metrics dont look good, we think were failing and we feel
terrible about it.
Takeaway: Metrics are important, but they arent everything. Dont tie your value
as an entrepreneur to your numbers, because itll destroy you emotionally.

The Dangers of a Laser Focus on


Key Performance Indicators
When youre at a peak, everything is great. Youll never be more confident in your
chances of becoming a massive success story.
But when you drop into a valley, your perspective can get pretty bleak.
There have been weeks, especially in the early days of Groove, when things felt
pretty miserable.
Our obsession with the numbers caused us to do some desperate things.
We discounted our product, and hurt the company in the process. We built way
too many features, trying to be everything to everyone. Instead of digging in and

433

talking to our customers and getting qualitative feedback, we I simply made


bad decisions because I was stressed that the numbers werent looking so good.

Bad Data-Driven Decisions

We learned a lot from those early fails.


After that, when we hit valleys, we would step back, ignore the numbers a bit, and
look at how the team was doing.
Were we unhappy?
Were there productivity issues?
Were we all burning out, and needed to take a break?
If human factors were responsible for the dip, then numbers dont really matter.

434

You cant A/B test your way out of an unhappy team.


Fluctuations are normal, and its important to understand and internalize that fact
so that instead of letting the valleys kill you, you know that you can fight through
that and live to fight another day.

Normal

Coming to terms with the fact that metrics arent the only thing that matters has
made a big impact on the way we run Groove.
Takeaway: Human factors are just as important as data. Dont ignore one at the
expense of the other.

Finding the Right Balance


Dont take this to say that being data-driven isnt important.
It absolutely is, and if you dont end up hitting your goals, you may very well fail.
But being too focused on core metrics can also lead to failure, because you end up
ignoring the human factors that are so important to your health as an effective
team.
Beyond our core metrics, Ive found that a focus on more vague measures like the
mood and happiness of your team has made a big difference in keeping us

435

growing, and the time we started to focus on that correlates closely to when our
growth curve startup looking up.
One thing that helps?
Vanity metrics.
You know, those pointless numbers that die-hard data heads love to scoff at.
Stats like social media mentions, pageviews and shares.

Vanity Metrics

Heres the thing: while those metrics might not correlate to your bottom line, they
sure feel good to get excited about. And in a startup where morale can be the
difference between calling it quits and keeping up the fight, thats really
important.
Takeaway: Theres still value in pointless metrics. The morale boost that they
create can be very valuable to your team.

How to Apply This to Your Business


Dont take this post to be a departure from our focus on data-driven growth.
Its not.
Were still working hard to drive up our core metrics; those core metrics, which
youll be reading a lot more about on this blog, are one of the most important ways
436

we gauge the health and growth of our business.


But theyre not the only way.
With so much metrics worship being plastered around the internet, I think its an
important reminder to all of us that theres more to business than the numbers.
And growth isnt always a hockey stick.
Growth can be messy, especially in the early years. And it can take you into deep
plunges along the way. You dont always get out of those plunges by simply
focusing on numbers.
Recognize that, and use it to your advantage to build a healthy, happy and
effective team.
I know I find it useful to remember from time to time, and I hope you do too.

437

How We Choose, Build and Launch


Partner Integrations to Grow Our
Business
October 30, 2014

This month, we released our biggest


partner integration yet. Heres how we
did it
Its a tough decision.
For any small software company, integrations are a painful balancing act.
On the one hand, there could be a huge potential upside from the partnership,
and your customers may be begging for you to integrate with the other products
they use.
On the other, youve got your own damn product to focus on.
Every hour your team spends building integrations with other services is an hour
theyre not spending fixing bugs or improving your core product.
Weve built nearly a dozen integrations in the last three years at Groove, but the
last several Olark, SnapEngage, HipChat and Slack have easily been the most
successful, both in terms of user engagement and new user acquisition.
438

Our approach to choosing partners and executing on the integrations may not be
as refined as some of the companies out there who have launched dozens or
hundreds of them, but weve learned quite a bit along the way, including a few
important strategic elements that have helped us launch bigger, convert better
and get more out of our investment into integrations.

Why Partner Integrations Are an Important


Part of Our Strategy
One of the major elements of our 12-month growth strategy is building
integrations with key partners. Heres why:

1) It Makes Groove More Valuable to New and Existing Customers


A few years ago when we first launched Groove (before the birth of this blog), our
customers were already asking for integrations with the other products they used.

Integration request

It makes sense: no business app exists in a silo.


We use nearly two dozen apps at Groove alone. If were choosing between
competing apps and one of them already has built-in functionality to work well
with our other products, thats a big win for us.
It means that we either dont have to spend development resources connecting
the apps in the background, or that we simply get a value-add that wasnt there
before.
For example, I love Hello Bars integration with Campaign Monitor that makes it
easy to add new subscribers to the right lists without doing any custom coding.

439

Integrations make both products more valuable

That makes less work for us, and it makes HelloBar a no-brainer. Thats the same
effect were trying to achieve with our own integrations.

2) It Gives Us an Audience That We Didnt Have Before


Slack has more than 11,500 business customers.
Sure, some of them probably read this blog. But Id be willing to bet that many, if
not most, have either never been here, or have stopped by and never come back.
When Slack announced the integration, it gave Groove exposure to an entirely
new audience of ridiculously qualified leads who already use a product that we
integrate seamlessly with that couldnt match our target personas more exactly.

Slack announcement

Today, were seeing more and more of them become Groove customers (more on
that later).

440

3) It Boosts Non-Quantifiable X-Factors


There are a number of benefits that dont necessarily fall into the trackable ROI
bucket, but that I have no doubt bring Groove new customers every day.
Building relationships with key people at other companies as you do when
youre working on an integration with their product has been an invaluable asset
to me. Its helped us launch big industry initiatives like the Small Business Stack
and secure standing open invitations to guest post on influential blogs, among
other opportunities.

The value of partnerships

It also helps to change the perception of Groove; when people see our name next
to huge players like HipChat and Slack, they make an association in their minds
that puts us in the same league as those much bigger, more successful companies.
Thats an instant win for establishing credibility and trust with new prospects.

441

How We Figure Out Whether an Integration


Is Worth Pursuing
With thousands of SaaS apps on the market, picking the best ones to build
integrations for isnt exactly easy.
The process isnt a cheap one: it takes many hours of developer time to build and
test, many hours of marketing time to prepare and execute on the launch, many
hours of support time to help customers who have questions about the
integration, and many hours of my own time to work on our relationship with the
partner and manage the project.

Key responsibilities

When all is said and done, its easy to run up a five-figure cost for a single
integration. Thats why maximizing the upside is absolutely critical.
Here are the three basic questions we start with:

1) Would It Significantly Increase the Value of Groove to Our


Customers?
Far and away the most important point. Would the new integration make Groove
much more valuable to new and existing customers?
Off the bat, this eliminates 95% of the possible integrations we could consider.
There are many products that our customers use that theyd never get value from
connecting to Groove.
442

On the other hand, there are product integrations that make both products much
more valuable for our customers.
Slack is a great example: weve often heard from customers that theyd like
desktop notifications for Groove messages. The Slack integration which pushes
notifications about new Groove activity to a users Slack room, makes that
possible.

Desktop notifications

And on the Slack side, many users spend their entire day in Slack. Theyve built a
habit of doing much of their communication in the app, so being able to get their
support emails in Slack and not having to always be logged in to Groove is a
big bonus for them.
Thats the sort of symbiotic value-add we look for as we build our integration
roadmap.

2) Do Our Customers Actually Want It?


We track customer requests closely so that we can make the best decisions about
our roadmap, and integrations are no exception.
When I spend time talking to customers, I make it a point to ask what other
products and services theyre using. Whenever we get an email requesting a
particular integration or feature, we log it in Trello with a link to the request.

443

And weve even been tipped off to customer interest by looking at what our
customers search for in our knowledge base.

Knowledge Base searches

Ultimately, we dont want to build anything that our customers dont want.

3) Are the Products, Brands and Markets Complimentary?


Theres a ton of overlap between the personas that Groove is right for and the
ones that Slack is right for.
Small and growing teams, often startups, SaaS and eCommerce companies, are a
big part of Slacks user base, and Grooves as well.
In contrast, there could be a lot of value-add for both products if we integrated
with an enterprise-level CRM like SAPs, but it wouldnt be all that useful to our
customers, who are way outside of that market.
Shared values is another important condition. As fluffy and meaningless as it
sounds, it has plenty of marketing value; Slack markets itself as a tool to make
work life simpler, more pleasant and more productive.

Slacks values

444

Our positioning is quite similar, and that overlap makes an integration much more
appealing to our shared customers.

4) Does the Company Want to Build a Relationship With Us?


Some companies are much easier to work with than others.
A company that puts effort into building an open API (a priority for us right now)
makes it easier and more inviting to build an integration with.
And a company thats willing to bring it and work with us to build and promote
the partnership is much more interesting than a company who will never mention
Groove to their customers.
In both of our big integration launches this year (HipChat and Slack), the
companies were incredibly cooperative and helpful in spreading the word;
something we discussed and agreed on before we started the work on our end.

Helping us promote

How We Handle Integration Launches


So far, weve followed a simple and straightforward approach thats similar to how
we launch new features, and its been working well for us:

445

1) Start With a Small Test Group


When our Slack integration was ready to roll out, I invited the users who had
specifically requested it in the past to be part of our initial test group.

This helped us not only kick the tires, but build a small team of evangelists who
would later promote the integration.

446

2) Execute the Real Launch


After a couple of weeks of testing, we felt confident releasing the integration to all
of our users.
We built a targeted landing page that would explain the integration to our
customers and why it would be valuable to them.

Landing page for Groove customers

And to drive traffic to it, we sent emails to our customers

447

Deployed an in-app announcement via Intercom

In-app announcement

And announced it on Twitter

Twitter announcement

3) Create Resources for the Integration Partner and Coordinate the


Launch
While we worked on our own targeted landing page, we built a similar page for
Slack users, explaining Groove and why the integration would be useful to them.

448

We also worked with the team at Slack to coordinate the promotion efforts, and
their Twitter announcement drove a couple hundred clicks.

Landing page for Slack customers

While Slack already has dozens of integration partners, they couldnt have been
more helpful and supportive for our launch.

4) Track Everything
Especially since were still new at launching integrations, we wanted to make
sure that we tracked our metrics as closely as we could to improve our strategy
and processes.
The early results have been promising.
The landing page for Slack users, while the traffic hasnt been heavy, has
converted visitors to trial users pretty well at 5.8%.

449

Slack page conversions

And from tracking our funnels in KISSmetrics, we know that visitors who click on
the Slack integration page link on our marketing site are 15% more likely to sign
up for a Groove trial.

Conversion rate for visitors who viewed Slack page

Were also seeing the effects of the integration as we ask new customers why they
signed up for Groove.

450

Why did you sign up?

Well continue to track our performance to help us evaluate future plans.

Our Next Steps


While weve gotten our first two big integrations under our belt, we still have a
lot of work left to do.

1) Evaluate Our Next Integrations


While we have a roadmap with possible integrations, were doubling down on
gathering customer input to inform our decisions. Next week, we're deploying a
survey to our customers asking them which integrations theyd like to see next.

2) Build a Zapier Integration


Zapier is a platform that makes it easy for users to build their own integrations
betweens the apps they use. They already support more than 300 SaaS apps, and
adding Groove to the list would help us point customers to an easy solution,
especially when theyre requesting integrations that dont have enough upside to
make sense for us to spend time on.

3) Build Grooves API


We want to give other companies the opportunity to integrate with Groove and
help us deliver more value to our own customers. Thats why building an open API
is high on our list of priorities. Weve just hired two new developers, and Im
excited to see that tackling that project is finally within reach.

451

How to Apply This to Your Business


Partner integrations are only a small part of our growth strategy, but theyre an
important one. Weve seen great benefits from building bridges from Groove to
other complementary products.
Our strategy is far from perfect, and its certainly not final. But its done well for
us so far.
I hope that this look into how we approach and execute on integrations will help
you make better decisions for your own roadmap and business.

452

How We Increased Our Net Promoter


Score by 45%
November 6, 2014

A couple of months ago, we sent out our


second NPS survey. Heres what
happened
Just this week, I got an email asking for a quote to include in another startups
blog post.
Whats your biggest piece of advice to budding entrepreneurs?
My answer to that question has evolved quite a bit over time.
At various points in Grooves growth, I mightve said something about finding the
right team, doing content marketing, keeping work/life balance or one of a dozen
or so other topics that I think about every single day.
Those are all very important issues.
But my answer now and Im more convinced about the value of this than I have
been about any of my other responses before is this:
If you havent spent at least as much time talking to your customers
as you have building your prototype, stop and go have as many
453

conversations as you possibly can. Ask open-ended questions about


peoples experiences and challenges and listen very carefully to the
words they use.
Youll get more game-changing insights about your product,
messaging, positioning and sales strategy than you could ever learn
from reading business books.
Weve gotten more value from collecting customer feedback than from any other
sales or development effort. Its changed our product, our marketing and our
business in huge ways.
As of a few months ago, one of the methods we use for gathering feedback is Net
Promoter Score surveys. We deployed our first one in June, and were thrilled with
how helpful it was.
In September, we sent our second NPS survey. Today, Im sharing the results,
along with lessons learned and tips to get more out of your own NPS efforts.

Net Promoter Score: A Refresher on


Our First Survey
In case you missed our June post about our first Net Promoter Score survey,
heres a quick bit of background on what NPS is
NPS measures customer loyalty and sentiment about your business by asking two
simple questions:

454

Results from the first question tell us how many of our customers are promoters
(those who respond with a 9 or 10), passives (7 or 8) and detractors (0 to 6) of
Groove.
Results from the second question tell us why.
If youre a regular reader, you know that were fanatics when it comes to gathering
customer feedback, which is why we gave NPS a shot in the first place.
The first time we did it, we got some fascinating feedback from Promoters about
what they loved about Groove

Promoter Feedback June 2014

Some even more valuable feedback from Passives about what it would take to get
them from like to love

Passive Feedback June 2014

And some helpful notes on what needed major improvements

Detractor Feedback June 2014

455

Extracting trends from the qualitative feedback gave us a top-down view of what
people loved most about Groove.

What Customers Love Most June 2014

That extraction would end up being a valuable benchmarking exercise for us in


our second go-around.
When all was said and done, we ended up with an overall score of 11.
Takeaway: The Net Promoter Score survey is a popular way for brands to measure
customer loyalty. Our first survey taught us a lot about what our customers were
thinking, so we were excited to make NPS a regular part of our performance
measurement.

NPS Round Two: Results


After our first survey, we committed to monitoring our NPS on a regular basis.
So four months later, we sent out our second survey.
456

A note on tools: in June, we used Promoter.io for our NPS survey, which is
an app that handles the deployment of the survey and collection/analysis
of the responses.
Having done a ton of qualitative feedback collection outside of NPS,
keeping the data organized and mapping out trends can be a huge
challenge when youre working with hundreds of customers, so it was a nobrainer to use Promoter again. Having all of our NPS surveys in one place is
really helpful, too.

In the interest of full disclosure, Promoter is a Groove customer (and thats


how I learned about it in the first place), but Im not getting anything for
mentioning the app here, I just really loved using it.
With that said, you could certainly make do with a SurveyMonkey/
spreadsheet combo of your own.

We were hoping for some movement since our first survey, and the results didnt
disappoint.
Again, we got everything from high praise that we can use to inform our
messaging

Promoter Feedback September 2014

To suggestions and feature requests to make Groove better

457

Passive Feedback September 2014

Along with bigger concerns that were threatening to cost us customers (or, more
likely, already have).

Detractor Feedback September 2014

Again, we found all of the feedback we got to be valuable, but it wasnt until we
looked at the trends in the qualitative responses that we got a much better sense
of the changes between this survey and our first

458

Weve spent many hours discussing the results on our team, and have come up
with a few big takeaways:

Win: UX/Simplicity Up by 15%

More than anything else, weve set out to build the simplest help desk software out
there.
The fact that weve been able to move the needle on our customers recognizing
that as being the defining aspect of our app tells me that were going in the right
direction.
A huge focus of ours in the last few months has been tackling some long-standing
bugs that have been hurting the user experience for some groups of our
customers, as well as putting a lot more general polish on our app.
I see these results as a win, though Id love to see that number go even higher in
the future.

Win: Active Development Up by 33%


One of the loudest complaints and frankly, most difficult to hear the last time
we did this survey was that we werent doing enough to move the app forward.
459

That really alarmed me.


Here we were, head-down in development mode day in and day out, but it didnt
really matter.
Many of the changes we shipped were mostly invisible to the majority of our
customers, and it lead to the perception that we werent making much progress.
Soon after that, I set out to add more engineers to our team to accelerate our
development, and started prioritizing customer-facing fixes and updates to ship
more frequently.

Based on this NPS win, and lots of other feedback from our customers, my feeling
is that its paying off.

Win: Price GONE


No, we havent changed our price.
But in our last survey, 5% of customers noted our price as the thing they loved
most about Groove. This time, less than 1% said the same.
Why do I see this as a win?

460

Because we dont want to compete on price.


Competing on price is a race to the bottom, and Id rather our users focus on what
makes our product better (things like UX/Simplicity and Active Development).

So to see Price eliminated as a major contender while the other factors rise in
significance suggests to me that fewer customers see Groove as a commodity
helpdesk and more customers are choosing us for features, functionality and
service.

Fail: Knowledge Base Issues Appear


Our Knowledge Base app has always been one of the most-used features of
Groove. In our first survey, less than 1% of our customers noted the knowledge
base as something theyd like to see improved.
This time, that number jumped by nearly 400%!
After digging into our feedback and reaching out to customers for follow-ups, the
best explanation we have for that jump is this: many of the customers who
complained about the knowledge base complained about other bugs (mainly an
email parsing issue) that we were having around the time of the first NPS survey.

461

With that issue fixed, knowledge base improvements became their next biggest
desire.

While it sucks to see complaints about a feature go up, I interpret it more as a nod
of where to focus our development efforts than a disheartening knock on our
product.

Fail: Participation Rate Down by 18%

The participation rate (the number of people who completed our NPS survey
462

divided by the number of people we sent it to) went from 18% in our first survey to
13% in our second.
While the industry average hovers around 10-15% and were still well within that
range, thats not a great trend.
I suspect that it has a lot to do with the fact that I was doing intensive customer
development trying to chat with every single one of our customers at around
the same time, and many of the customers who participated in my interviews
didnt see the need to respond to our NPS survey.
Its an important lesson learned for next time: one survey at a time.

Win: NPS Up by 46%

Going from a Net Promoter Score of 11 to 16 is a big, big win. While there are many
companies with far higher scores, we made a big jump in an important customer
loyalty benchmark.

The Power of NPS Follow-Ups


If theres one tactic you take away from this post for your own NPS surveys, I hope
its this one: do not neglect to follow up with your customers after the survey.
The feedback we got opened a lot of doors for conversations with our customers
we might not have otherwise had. In some cases, it helped us dig in and get to the
bottom of tough product issues that our customers were facing. And in many
463

cases, it strengthened our relationships and made customers happier.


In many cases, customers were having issues that we already had fixes or features
for. For example, one customer mentioned that theyd like to see integrated live
chat. We had released our Olark integration the week prior, and we reached out to
let them know.

Great feedback for us, and an easy win for the customer.

How to Apply This to Your Business


NPS surveys are not the only way to get feedback from your customers, and you
shouldnt treat them as such.
Pound for pound, actually going out and talking to your customers one-on-one
will yield far more valuable, business-changing results, and you need to be doing
that.
But customer development is incredibly time-consuming, and NPS surveys give
you a great way to collect feedback on a regular basis with only a few clicks.
Plus, NPS gives you a valuable benchmark to measure your growth against, and it
helps you spot trends in your customers feedback.
As part of a larger customer development strategy to get closer to our customers,
weve found Net Promoter Score surveys to be really valuable, and I hope you will,
too.

464

Why I Walked Away From a $12M


Acquisition Offer 18 Months After Our
Startups Launch
November 13, 2014

As a founder, some decisions come


naturally to me. This was one of the
hardest Ive ever had to make
To some readers, this post is going to seem self-indulgent.
Like Im congratulating myself for not giving in to temptation.
Truthfully, the fear of coming across that way was almost enough to keep me from
sharing this story.
But I sent a draft to a founder friend of mine, and within a few minutes he shot
back:

465

Many founders who persist for long enough do have to deal with something like
this at one point or another.
So in the hopes that this ends up helping another founder going through a similar
decision and because Ive worked hard to make a habit of sharing everything, no
matter how uncomfortable, on this blog today Im sharing one of the most
difficult decisions Ive had to make as an entrepreneur.

The Offer
In early summer of this year, I was approached by a business development
executive at a big software company.
He and his team were tremendously supportive of our business, and gave us lots
of great insight into growth that their employer used to become successful.
This isnt the first time Ive been approached by someone in that position. In the
past, weve had conversations about Groove, our growth and our goals, and it
usually ends there. Ive never expressed interest in selling the company.
On the other hand, I almost always try to steer the conversation toward
partnership opportunities; our product partnerships have been big wins for our
customers, and theyre a big part of our growth strategy.
This time, it was different.
Its not a company that would be a natural product partner for us. And its not a
company I would expect to want to add customer service software to their
offering, so I wasnt quite sure what to expect.
I wish I could say, for the sake of story, that there was a dramatic offer moment
where a number was written on a piece of paper and slid across the table. That
wouldve made for a much better post.
But in reality, the situation unfolded over a few months of discussions. We had a
handful of meetings with their business development team and executive teams,
and their engineering team did a thorough technology review of Groove.
Finally, I got the call that I knew was coming: they wanted to acquire Groove.
Details and due diligence would have to be sorted out, but the number was just
under $12 million. Our whole team would stay onboard.
At the time, I was floored.
Our monthly revenue was around $70K at the time, making $11.8M a 14x multiple
466

on our annual revenue. Even in SaaS, thats on the very high end of the norm, and
a multiple generally reserved for highly profitable companies (or ones with
massive user bases).

It was certainly far more than I expected.

Considering the Offer


Over the next several days, I spent a lot of time talking to my team, mentors,
advisors and family.
The most compelling argument for taking the offer? Id be an idiot not to.
With my owning more than 50% of the company, the money would, without a
doubt, be life-changing.
Theres not a whole lot that that kind of money wouldnt buy you.

467

I love what I do every day, but theres no doubt that there are days when it
absolutely sucks.
The money would also be business-changing.
Our product roadmap is aggressive, and having the backing of a large benefactor
would let us hit our targets much faster. It would let us build an even better
product and spend more on marketing to reach even more customers.
But thats precisely where the benefits begin to unravel (more on that in a bit).
Almost a week later, I picked up the phone.
And then I put it down.
I picked it up again.
And put it down.
I went through this cycle three or four times before I took a break and went for a
walk.
It was a call I really didnt want to make.
I wandered for an hour before coming home. Angry at myself for stalling, I gritted
my teeth, dialed the number and forced myself to hit Call.
It went to voicemail.
Shit.
Asking him to call back, I settled in for an agonizing hour while I waited, fidgeting
and completely incapable of doing any work.
Finally, the call came.
Slowly, painfully and with as much certainty as I could fake, I somehow managed
to get it out: I cant tell you how much I appreciate the offer, but its not the right
move for us right now.

Why I Said No
A serial entrepreneur friend once said something thats stuck with me:
First-time founders care most about their exit. Every time after that,
you focus on legacy.
468

Im not sure that he was the first to say it, and I have no doubt that it doesnt apply
to everyone, but I like to think it rings true for me.
After my last company got acquired, I didnt set out to build something I could sell.
I started Groove to build something that would make something that was a
massive pain for me managing customer support better for the millions of
businesses that I knew it was a pain for, too.
Weve come a long way toward doing that, but the amount of ground we havent
covered dwarfs how far weve come by many, many multiples.
Ive seen what happens to customer service companies that get acquired by giants
or take in many millions of dollars in funding.
Products that founders swore they built to be simple got bloated, overdeveloped
and lost sight of their vision.
I see customers coming to Groove every single day from these companies
precisely because of what happened after our competitors got so big.
Nearly everyone who gets acquired sends an email to customers along the lines of:
Everything will stay the same, were just going to have more resources to make
things better for you.
Everyone whos used apps built by these acquired companies know that sooner or
later, that promise almost always turns out to be bullshit.
I cant risk Groove becoming part of the problem, the enemy of what we set out to
create.
We may be successful in some ways, but were still young, and were still fragile.
Theres too much at stake.
The time may come when an acquisition makes sense, when Im certain that our
customers and our product can still win if ultimate control of the company
changes hands.
But that time isnt now.

The Big Picture


I know what some readers are thinking here:
This is BS. Everyone has a price, and if the offer were big enough, none of those soft
reasons wouldve mattered.

469

And while I disagree that the other factors wouldnt have mattered, lets talk about
price.
At the time of the offer, our monthly recurring revenue was around $70,000. A
$12M acquisition would be a 14x multiple on annual revenue.

However, wed been growing very steadily and predictably at around 10% per
month.
After $100K, most companies see that growth rate to begin to drop incrementally.
Still, its reasonable to assume that, even at an average growth rate of 6%, our MRR
could be close to $200K at this time next year.
At a 10x multiple (still high but lower than what weve been offered), thats an
acquisition price of $24,000,000. Double what the company would have sold for
this year.

One year from now

470

A year after that (assuming growth rate levels off at around 5%), MRR would be
closer to $359K. At a 10x multiple, thats $43,080,000.

Two years from now

Even if the other shareholders and I choose to take a dividend on the companys
profits a very likely scenario, and one thats a lot more appealing to me rather
than selling the company, wed still fare better in a year than by taking $12M today.
Obviously the math here is far from black and white.
There are hundreds of intangibles at play, and hoping to time the market properly
has shown itself to be a suckers bet for founders many, many times.
But its hard to deny that the upside in a year looks much, much better than it
does right now.

471

The 5 Ultimate Questions


In retrospect, for me, the decision ended up coming down to five big questions:

1) Would It Be a Win for Existing Customers?


To me, this was a clear no.
Weve spent three years and a lot of sweat building relationships with customers
who trust us to make sure that they have a great customer service product.
The risk of letting them down before weve achieved our product goals would be
more of a personal failure than I can accept.

2) Would It Be a Win for Future Customers?


Maybe. Additional marketing resources would definitely help us reach more future
customers.
But unless we maintain the strength of the existing product, that doesnt mean
much.

3) Would It Be a Win for the Team?


Financially, yes. Everyone who has a stake in Grooves success would win
handsomely, and our whole team would be working for a stable, well-known
company.

472

This was probably the hardest win for me to reconcile, as the Groove team has
worked their asses off to get us to where we are. But in open, honest
conversations, we agreed that the upside would be bigger to keep our heads down
and keep building.
And beyond the upside, one of our employees noted that he didnt want a prison
sentence. He came onboard to work at a growing, fast-paced startup, not a
bigger, slower enterprise. Others agreed.

4) Would It Be a Win for Investors?


Somewhat. This wouldve made our investors much more than whole.
But after talking to them about how I felt about the offer, and considering how
dramatically their upside could improve if we waited and kept working, they
supported my decision.

5) Would It Be a Win for Me?


Theres no doubt the money would make a huge impact on my life.
But in the end, it simply wasnt the kind of win I wanted. If our customers, our
team, our investors and our legacy dont win, then neither do I.
With this framework, and without five clear yess, the decision became a lot easier.

How to Apply This to Your Business


To be completely honest, if a founder came to me in the same position and asked
for advice, Id probably tell them to take the money.
But for Groove (and our goals), I feel confident that we made the right choice.
I also recognize that most businesses wont deal with this problem.
But MANY businesses, once they reach a certain point, get offers for acquisitions,
acqui-hires, big investments and partnerships.
While each of this is a drastically different scenario, I hope that the framework I
used will be helpful to you as you make one of the most difficult decisions of your
entrepreneurial life.

473

How We Created a Product Explainer


Video That Actually Got People to Buy
November 20, 2014

Product demo videos are hard to do


right. Heres how we made one that
worked
Our first attempt at a product video was less than stellar.
Thats not to say that it looked bad; a friend of mine shot and edited it, and I think
it turned out great.
But we created it when we were still young and immature as a company. Before
we really took the time to understand our customers as deeply as we do today.
And it showed.
It was, essentially, a feature-packed all about us video press release.
And much to our chagrin, in all of our customer development, not a single
customer has used the terms hassle-free ticket management, smart
automation or intuitive self-help tools, which is why watching that video now
makes me cringe.
Weve come a long way since then. Were a little bit bigger, a little bit smarter, and
474

armed with a lot more data and feedback to help us tell the right story.

Old Video

We swapped out the old video with a testimonial video a while ago, but we were
missing anything that truly showed our product in detail to the people that
wanted to see it.
So when we redesigned our marketing site a few months ago, we decided to take a
new look at our video.

How to Pick a Video Production Agency


In this area, we were lucky.
We already had a great relationship with Allan Branch and the team at
Less Everything, the company behind Less Accounting and video agency
Less Films.
We had the Less folks produce a great testimonial video for us earlier this year, so
it was a no-brainer to pick them for this project.
Note: Less Accounting is a Groove customer, but were getting absolutely nothing for
mentioning any of the companys brands here, and a blog post was never part of our
discussions with them. They didnt even know this mention was coming until
yesterday when we reached out to confirm a few points in the post for accuracy.

475

The biggest reason I mention them is because we keep getting emails like this one:

With that said, we have gone through this process before when we took earlier
stabs at making demo videos.
Ive asked a lot of different questions of potential video partners, but really, any
good agency can answer most of them correctly.
By far, the best screening question (that actually made a clear separation between
agencies we wanted to work with and those that we didnt) was:
How will you approach creating this video?
This question is designed to make sure that your goals are aligned with those of
the agency.
If the answer doesnt include critical elements like getting a deep understanding of
our potential customers and their wants, needs and objections, along with what
makes them want to buy, thats an instant red flag.
Weve done the work and can supply this information, but if the agency isnt
prioritizing that over fluffier things like creativity, then our goals arent aligned.
This also helps you get a feel for whether the agencys project management
workflow fits with yours (e.g., do they use tools that youre familiar and
comfortable with?), as well as a more general sense of what the team will be like to
work with.
Eric at Less Films also pointed out a great technical question that we should be
asking:
Do we get to keep all of the assets/illustrations from the video?
As a startup, our product is constantly evolving and improving, and we want to
show off new developments.
We also want to be able to make changes to the video if we think that parts of it
could be working better.

476

Its possible, however, that we wouldnt want to engage the same agency for that
work, especially if we didnt have a great time working with them.
If its something we can do much cheaper and just as well, for minor changes
in-house, itd be a poor business move to outsource it.
Plus, theres no guarantee that whatever agency you work with will be around
when you need to revise your video, so its important to ensure that youll always
have access and ownership of those assets.
With a partner picked, it was time to get started.

Writing the Product Video Script


While many agencies offer scriptwriting as part of their services, it was important
to our team that we wrote the initial script ourselves.
We didnt just want to show off the product; we wanted the core of the script to
focus on what we already knew from our customer development efforts: what our
customers burning pains are, whats most important to them about solving those
pains, and what key points about Groove actually trigger them to sign up.
Do not start this process until youve done the upfront work to figure out
what your customers biggest pains are (in their own words), and exactly
how your solution can solve that pain for them.

Video Script Flow

477

Once we had that, wed feel comfortable handing the script off to the agency for
them to apply their storytelling expertise to it.
The approach that we took was similar to our approach to writing website copy.
We took the exact language that we heard from customers in our conversations
with them, and applied it to a simple flow: What we ended up with was a 90second initial script, which we would change several times throughout the
process.

Script

I cant stress enough how important customer development was to this project,
just as it has been to every marketing project weve done.
478

Once we were satisfied with the script, we were ready to move on to production.

The 5-Step Product Video Production


Process
Armed with a script, we walked through our ideas with Eric, and he had some
great feedback for us on how to make the story more compelling. The way a story
comes across in video is completely different than the way the same story might
come across in print, so the agencys expertise is vital here.
We agreed on a general direction, and Eric was off to work.

1) Storyboard
A few days later, he sent us a rough storyboard of his vision for the video (click on
the image below to see the full storyboard).

To make things easier, Eric sent an audio walkthrough of the storyboard, which
was incredibly helpful.
One lesson Ive learned from working on a number of products with agencies is
that rough means exactly that. A lot of folks Ive talked to about this feel timid
about giving tons of feedback, even early on, thinking that it might offend the
agency.
This couldnt be further from the truth, and if your agency doesnt take feedback
well, run.
The process is a collaboration, and you wont get to where you need to be without
both parties being deeply involved.
479

Len and I had a lot of feedback on the first storyboard. And the Less team was
happy to get it.

Initial Storyboard Revisions

After a few days of back and forth, we had a storyboard that we were happy to
move forward with (click on the image below to see the full storyboard).
480

Storyboard: Version 5 (Final)

2) Visuals
We agreed that we liked the illustrated look that Eric came up with, and it was
time to work on visuals.
Eric focused on building illustrations that evoked the simplicity and emotions that
we felt represented Groove, while we focused on picking in-app screenshots for
the features that are more interesting to Groove prospects.
We took lots of extra screenshots to make sure that Eric had plenty of options to
work with.

Collecting Screenshots

481

The heaviest lift of this whole project, on Erics side, would be to put the images
together and animate them, so it was important to get final sign-off on the images
before the animation started.

3) Voiceover and Music


While Eric worked on the visuals, he had a few voiceover artists from Voices.com
read our script and send us auditions.
Of the eight options, we picked our favorite, though we still had notes for
revisions.

VO Revisions

One non-obvious thing we did which has proven to be very valuable down the
line:
Have the VO artist record alternate lines that you might use in the future.
For example, we had them record lines that included future integrations
we had planned, as well as alternate free trial lengths so that we could A/B
test them later on. This saves time and money having to track down the
artist to record again.

The process for picking music was much the same. Eric sent us seven options
from Audio Jungle, made a recommendation, and we picked our favorite.
I wish that we could say we had some scientific, data-driven process for the audio,
but really we just went with our gut on which voice and music we felt sounded
most like Groove.

4) Putting It All Together: Rough Cut


About a month after we started, we had a rough cut of our product video to
review.

482

Rough Cut

It was amazing to see the video come together from our early script. Of course,
though, there were plenty of notes:

Rough Cut Notes

But we were close, and we could feel it. After a couple of final revisions, we had
our video.

5) The Final Video


To say that we were happy with the video would be a big understatement.
483

Final Product Video

We finally had a video that represented everything we had learned from and about
our customers as our company grew up.
Unfortunately, the fact that we loved it didnt really matter. The only way to gauge
the success of the project would be to test the video in the field.

The Results
We A/B tested the new video on our homepage against the existing testimonial
video that was on there previously.
After a few days, the results were clear:

484

A .6% boost nets out to an 11% increase over our previous conversion rate!
Beyond that, we get some great insights from the first email that we send to every
Groove customer.

Youre In Email

Weve gotten more than a few responses just like this one:

Re: Youre In

In all, we spent in the neighborhood of $5-$8K on this project, and over time, the
results look like theyll more than pay for it.

485

How to Apply This to Your Business


Video may not be the best medium to sell every product.
But for us, its boosted our conversion rate and helped us tell the Groove story to a
lot of customers who mightve otherwise not read our copy or tried our app.
If youre considering building a product video, I hope that our experiences help
you make the right choices along the way, and that you end up with a video that
actually does what it needs to: gets people to buy.

486

How Gratitude Has Made Me a Better


Founder
November 25, 2014

This week, many of us are thinking about


what were thankful for. Heres my take
An entrepreneur is all Ive ever wanted to be.
And since college, its all Ive been.
Some days when things are going well the role makes me indescribably happy.
And some days when things really suck the role drags me into lows lower than
I thought possible.
When Im in a valley, everything and everyone around me suffers. If my decisionmaking is impacted by my emotions (and of course it is), that has consequences
for the entire company.
So at the end of the day, I have two jobs: Im responsible for the success of the
company, and Im responsible for my own personal growth and well-being. The
two roles feed each other.
I dont think this is unique to founders.

487

I think we all have an ultimate responsibility to look after ourselves, because


meeting that responsibility helps us meet our other responsibilities to our
coworkers, our families and everyone else we come across.
One of the ways Ive worked on preserving and promoting my own well-being as a
founder is by practicing patience. Another is by taking time off.
And another way, particularly appropriate for this week, is by actively practicing
gratitude.

The Importance of Gratitude


The idea of gratitude has probably been diluted over the years by fluffy
motivational posters.
And that sucks, because as a concept, its damn powerful.
I loved Tim Ferriss podcast interview with Tony Robbins (the two parts are an
hour long each, but both are well worth listening to).
In it, Robbins talks about the importance of gratitude in his morning routine: each
day, he recites three things that hes grateful for. One of those, he says, must be
something ridiculously simple and non-material: the feeling of the wind on his
face, for example.
He notes that the reason some of the wealthy, successful people he works with are
unfulfilled and unhappy is because they base their lives off of expectations, rather
than appreciation, and that reversing the two can cause a monumental shift in
happiness.
Whatever your thoughts on Robbins I know that some arent fans its hard to
deny the truth in that perspective, especially after youve tried to put it into
practice.

How I Practice Gratitude


Im not a monk, and I dont respond to every situation with a calm, confident
smile.
I lose my cool, I make bad decisions and I disappoint myself from time to time.
But Ive found that practicing gratitude, just like working out, improves my mental
fitness over time.

488

And just like working out, theres an important caveat:


Its ridiculously easy to be grateful when things are going well. But its a
thousand times more important to practice gratitude when they arent.

Other than that, practicing gratitude really is as simple as it sounds: each day, no
matter how things are going, simply list things that youre grateful for.

9 Things Im Grateful for


Here are a few of the things that constantly come up when Ive thought about
gratitude lately. Ive randomized the order because I think its helpful to think
about everything were grateful for, rather than what were most grateful for.

My View

This is what I look at from my desk in Newport. I never get tired of it.

My Customers
This isnt my attempt at a canned Thanksgiving thank you. I feel deep, burning
gratitude every single time I think about the fact that someone trusts what weve
built enough to let us handle every support email that their loyal customers send.
489

That trust keeps us all going, and it certainly makes me appreciate my relationship
with every last one of our customers.

My Dog

Honey Badger keeps me company at work, and gets me out of the house to play
often enough to keep me sane.

My Team
From the start, I knew that Grooves success could only happen if I surrounded
myself with smart, talented and ridiculously dedicated people. Even though were
spread around the world, weve grown close and every single person has had a
major impact on not only Grooves growth, but on my own growth as an
entrepreneur.

My Wife and Family


I got married this year to the woman I love, and that in itself gives me enough to
be grateful for to last a lifetime.

490

My Board

My surf board is my biggest source of stress relief.

My Readers
This blog was started as a marketing channel, theres no doubt about that. But I
was hoping to share our experiences and write the content that I wished existed
the first time that I started a business, and I expected a handful of people to end
up following us and giving Groove a try. A year later, more than 20,000 of you have
invited us into your inboxes, and tens of thousands more come to visit every week.
It boggles my mind. Im immensely grateful for every read, share and comment
that we get.

My Company
Groove has been doing well lately. Were closing in on our $100K/month goal (and
will have an exciting announcement about that soon. For those who have been
asking, no, theres no way this blog is going away), and weve been extremely
fortunate in our growth the last several months. Its low-hanging fruit, but its hard
not to be incredibly grateful for that.

My Friends
Especially in the early days of Groove when things always felt like they were at a
stall, being able to lean on my friends was a huge source of much-needed stability.
I value my friendships dearly, and while I dont really say that to my friends too
often, I think it constantly.

491

Your Turn: What Are You Grateful For?


Gratitude has made me a better founder and a more rounded, happy person.
I hope this post has convinced you to give the practice a try, and I challenge you
to start right now: think about 3 things youre grateful for, and use the Tony
Robbins principle: one of them must be simple and abundant, even when things at
work or home arent going so well.
Happy Thanksgiving to all who celebrate, and a huge, heartfelt thank you to all of
you.

492

Lessons Learned Growing a Startup


From Zero to $100k/month in 2 Years
December 4, 2014

Faster than we expected, weve hit a


huge business goal. Heres what happens
next
Wow.
Fourteen months ago, we published the very first post on this blog about our
Journey to $100K.
I had no idea, expectation or belief that wed be publishing todays post this soon.
If you asked me then, I wouldve told you that we were years away.
But over the last several turning point months, it started to become clear that I
wouldve been wrong.
Last Tuesday, November 25th was a huge day for our team. At 2:14PM EST, we
recorded the trial-to-customer conversion that put us over $100,000 in monthly
revenue.
I knew the day before that it would likely happen on Tuesday, but I still managed
to forget to check our numbers until the end of the day, by which point we were a
few customers past that mark.
493

Still, I was obviously elated. It was a day that we had been waiting a long time for.
And because of this blog, it was a day a lot of people had been waiting a long time
for.
And while my thoughts on the milestone and what it means have evolved over the
last year, Im excited to write this post.
Im excited because in that first post, I said:
This is the blog I wish I had read the first time I started a company.
Its going to cover the lessons we learn from our own experiences,
including our tests, our wins and our fails, backed up with real
numbers. Everything from design, development, strategy, marketing,
sales, growth hacking, hiring, fundraising, culture, customer support
and more.
And Im happy that, as I look back at the 50+ posts weve written, thats still true.
The amount Ive learned over the last 14 months has been incredible, and it makes
me happy that others have been able to learn from our experiences, wins and fails
too.
Today, Im going to share the biggest lessons we learned on our journey so far, as
well as what comes next.
For the hundreds who have already commented and emailed to ask: no, the blog isnt
going away. Not by a long shot. More on that at the end of the post.

The 4 Biggest Lessons Learned Growing


From $30,000 to $100,000 in MRR in 14
Months
One thing thats struck me is that the more we mature as a company, the fewer
things there are that we see as critical to our success.
When we hit $30,000 in MRR, I published a post about the lessons we learned,
including the importance of activation emails and referral hacks.
Then, when we hit $50,000 in MRR, I published another post about our takeaways,
focusing on customer development and messaging, among other things.
Looking back, as a company, we matured a lot in the space between $30,000 and
$50,000. Probably even more than we matured in the time from $50,000 to
$100,000.

494

Early on, our focus was on tactics. We turned a corner when we shifted that focus
to strategy.
Now that weve had a chance to test all of the lessons weve learned along the way,
the most important factors in our growth become very, very clear.

1) Theres Literally NOTHING More Important Than Deeply


Understanding Your Customers
Chances are high that you dont know your customers as well as you need to.
We certainly dont; customer development is an intensive, ongoing process for us,
and were learning new things every single day.
Add to that pursuit the fact that our customers are constantly changing, and its
easy to see why customer development is not a task or a project, but a way of
running a business that never gets put on the back-burner.
Nearly every mistake we made early on can be attributed to not understanding
our customers well enough.
Spent $50K building the wrong site and the wrong product?

As much as it hurts to write now, one day of asking questions and intently
495

listening to our prospective customers wouldve avoided that.


Lost $12,000 by discounting and as a result, reducing the perceived value of
our product?

A few dozen conversations wouldve made it clear that price wasnt even in the top
five things that customers were concerned about when it came to choosing
Groove.
Again and again, we made screwups that would never have happened if we had
known what we know now: in business, conversations with your customers and
prospects are the most valuable assets you have

We do customer development in a number of different ways:

Youre In Email
Probably the only hack that were still using $100,000 later, sending an email to
every customer asking them why they signed up has been one of the most
powerful data-collection tools weve ever tried (and weve tried some expensive
tools).

496

This email has singlehandedly given us deep insights into the triggers that cause
people to sign up for Groove, and weve been able to apply those to our marketing
with tremendous results.
Customer Service
Theres a reason that I, as a CEO, spend more than half of my time doing customer
support: its that valuable.
Getting to see exactly what our customers are thinking and feeling about our app
is a huge advantage when it comes to thinking strategically about what to build,
fix and upgrade next.
All businesses have to do customer service, but weve made it a crucial part of our
customer development flow: recurring support requests get logged in our
marketing spreadsheets just as often as they get logged in Pivotal Tracker.
Net Promoter Score Surveys
In June of this year, we began doing Net Promoter Score surveys to gauge
customer loyalty and, more importantly, collect qualitative feedback from our
customers.
To say that we learned a lot would be a big understatement. We were able to an
accurate view of exactly what people liked and disliked about Groove.
497

Weve continued to do NPS surveys, most recently increasing our score by 45%.
We have no plans to stop doing these.
The Old-Fashioned Way
With all of the hacks and tools out there, Ive found that theres still no substitute
for one-on-one conversations with customers.
Pound for pound, these will give you more deep insights and raw, unfiltered
feedback than any other method.
Its why I make it a point to talk to every single Groove customer.

Customer Interviews

If I knew then what I know now, I would have been doing this from day one.

2) Dont Underestimate the Power of Messaging, Positioning and


Copy
In our earliest days, Groove was a design-first company when it came to our
marketing site.

498

We built what we thought would be beautiful (a mistake to begin with, as we now


know that form follows function in effective design), and then figured out what
copy would fit within those parameters.

Over the years, our approach has changed completely.

499

While weve redesigned our site a number of times, one thing that has remained
constant in our growth has been the massive difference that testing messaging,
positioning and copy makes.
But heres the thing: you cant have good copy without first doing the work to
understand your customers. Much of the copy on our site now came directly from
our customers mouths in our conversations with them, and thats why it converts:
because it speaks their language, not ours.
And dont forget to test.
Better Homes & Gardens tests their magazine cover blurbs not the main
headlines, but the tiny blurbs along the sides of the cover with tens of
thousands of non-subscribers before they go to print, to see which blurbs make
folks more likely to pick the magazine up off of the newsstand.
If one of the most successful and long-standing magazine publishers still doesnt
know enough to write persuasive, final copy without testing, what hope do we
have?
Thats why we test everything with Optimizely.

3) Content Marketing Is Ridiculously Effective (If You Do It Right)


Ive said this a number of times on this blog and elsewhere, but it bears repeating
over and over again: content marketing has been the single biggest driver of
growth for our company.
Not advertising (which we dont do).
Not affiliate marketing (which we probably wont do).
And not referrals (which we do but need to do better).
Content.
This blog.
Guest blogging.
Our new customer service blog.
Our content efforts have carried the growth of this company, and the ROI of
blogging is not to be ignored.
Heres what our growth chart has looked like:

500

Like many of these lessons, if I had known better, I wouldve done this from day
one.
But its also important to understand that the results of your content marketing,
like any strategy, depend completely on setting the right goals and executing the
right way.
If your goal is have a blog and you execute by writing blog posts, then thats all
youve accomplished.
But if your goal is to build your business through content, theres more to
consider. Its not difficult and literally anybody can do it. Here are the two things I
wish I knew when I started:
Take the Time to Create Good Content
Anyone can write B content. Most people do.
Thats why A content gets shared and consumed so much. By taking a few extra
hours on each post, you can exponentially increase the effect of your content.
Over time, you learn what your respond best to, from topics to format and
structure, but the key is not to half-ass it. Invest in good, thoughtful content that
solves real problems for people.

501

Promote the Absolute Hell Out of It


Within a few weeks of launching the blog, we had thousands of subscribers.
That wasnt just because the content resonated with people.
It was because the hundreds of hours we spent behind the scenes building
relationships with people, doing influencer engagement and promotion.
When we hit publish, the work was only half done.

Outreach Email

Good content is useless to your business without relentless promotion.


And if, like many people, you feel spammy promoting your content, consider two
things: first, if your content is truly valuable, then you owe it to people to get it in
front of as many eyeballs as possible. And second, influencers are influencers
because they add value to their audience. If your content adds value to their
audience, theyre happy to share it.

4) There Will NEVER Come a Point When You Know Enough


Im an entrepreneur, but Im not an expert.
I wouldnt consider myself an expert in any of the things that Groove is good at:

502

customer development, messaging and content marketing among them.


I might know a lot about some of those things, but the amount I dont know will,
for the foreseeable future, dwarf what I do know.

Knowing what you dont know is more useful than being


brilliant.
Charlie Munger

Understanding that non-expert status is the reason weve been able to do so well
in those areas: because our execution always starts with learning, rather than
doing.
Whenever we try something new, we dig into what the real experts say about it.
Sometimes, what they say helps us. Other times, it doesnt and we have to carve
our own path.
But its always valuable to put in the effort to research, read and learn about the
strategies you try before you try them. That way, when something doesnt work,
you understand why and what you need to do adjust.
Most recently, this became clear in my total about-face on SEO: I thought it was
spammy because I didnt understand it at all.
By taking the time to learn about SEO and by talking to and working with people
who know more about it than I do - I came to realize how powerful it can actually
be, and how, when done right, it can actually help you deliver more value to
readers.
Some of the resources I found invaluable were:
Neil Patels SEO: A Comprehensive Guide for Beginners.
David Zhengs guest post on OkDork, How We Grew OkDork 200%
With These Exact SEO Tips.
Brian Clarks How To Create Compelling Content That Ranks Well In
Search Engines.
The Adaptive SEO Approach by Yomar Lopez on the Unbounce blog.

By knowing and appreciating how much you dont know, and realizing how much
value it can have for your business to learn from the best, it no longer seems like a
waste of time to spend an entire work day reading about SEO, content marketing
or any other growth-related topic.

503

The Future of the Journey to $100K Blog


Over the past couple of months, people have noticed that we were getting close to
our goal. Weve gotten quite a few comments like this one.

For a long time, especially early on, I didnt really know the answer to that. This
blog was built around the narrative of our journey to $100,000 in monthly
revenue. So if that narrative concludes, what happens to the blog?
Over the last year, Ive come to look at our journey very differently.
$100,000 is a milestone. A big one, for sure.
But its not a finish line.
And frankly, theres no number that represents a finish line for us. Were in this
to grow Groove into the best customer service software company on the planet
though not necessarily the biggest and revenue is only a small part of that.
At the same time, the monthly revenue number represents a benchmark that
helps us chart our path, and its something that weve become known for through
the blog.
So with that said, heres how weve decided to move forward: the blog isnt going
away, and the story isnt over. Not by a long shot.

A New Goal: $500K in Monthly Revenue

504

While I no longer believe that monthly revenue is the most important marker of
the health of a business, I believe deeply in the power of tangible goals to help a
business grow. So now, were setting our sights on $500,000.
Theres no timeline for this: I expect our growth rate to slow down a bit, as it
generally does once a business reaches various thresholds. Its not realistic to
expect 10% monthly growth forever, or even for a long time.
But were going to get there, and were going to continue sharing everything we
learn along the way.

A Lot of Things Have Been Left Unsaid


This blog is entering its 60th week.
Over the last year, weve done, tested and learned a lot more than 60 things.
The Trello board that holds our topic ideas runs into the hundreds.

Theres still a lot we havent shared, only because we havent gotten a chance to
yet.
Insights from a year ago, six months ago and even a week ago that I think will be
just as valuable to growing businesses as the lessons we have shared on the blog.
Some examples:
How we increased trial-to-paid conversions 30% by testing free trial lengths

505

The email that convinces 20% of abandoning customers to stay with Groove
How we come up with 10 new blog post ideas every week
Im looking forward to sharing those untold stories along with everything new that
we do.

Bringing in New Voices


The voice of this blog mine is very distinct. Its the only one thats appeared
here for the last year.
However, there are a lot of very brilliant people who can share some valuable
insights and add color to our own experiences. Entrepreneurs, advisors and
investors that Ive built relationships with over the past few years that I continue
to learn from every day.
Ill be testing featuring some of those voices, and their compelling lessons, on the
blog from time to time.
Im only going to feature guest posts that meet the standards we set for ourselves
here.
Additionally, an update Im especially excited about: well be interviewing other
founders on lessons theyve learned on their own journeys to their first $100,000
in monthly revenue, and featuring them here.
The first interview were publishing will be with an entrepreneur Ive learned a
tremendous amount from: Hiten Shah, co-founder of KISSmetrics.

Finally, and importantly: this doesnt mean Im slowing down on content. Im still
going to be publishing every single week.
But reaching a milestone gives us an opportunity to make improvements to this
blog that didnt necessarily fit with the old narrative, and Im excited to do even
more to deliver value to our readers.

506

I hope youll stay along for the ride.


To every single one of you who has read, commented and shared our posts: I
appreciate you more than you can know.

507

S-ar putea să vă placă și