How to Grow Your Business: Lessons from Zero to $100k/month in 2 Years

Faster than we expected, we’ve hit a huge business goal. Here’s 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 we’d be publishing today’s post this soon. If you asked me then, I would’ve told you that we were years away.

But over the last several turning point months, it started to become clear that I would’ve 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.

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, I’m excited to write this post.

I’m excited because in that first post, I said:

This is the blog I wish I had read the first time I started a company. It’s 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 I’m happy that, as I look back at the 50+ posts we’ve written, that’s still true. The amount I’ve 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, I’m 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 isn’t 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 that’s 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.

Early on, our focus was on tactics. We turned a corner when we shifted that focus to strategy.

Now that we’ve had a chance to test all of the lessons we’ve learned along the way, the most important factors in our growth become very, very clear.

1) There’s Literally NOTHING More Important Than Deeply Understanding Your Customers

Chances are high that you don’t know your customers as well as you need to.

We certainly don’t; customer development is an intensive, ongoing process for us, and we’re learning new things every single day. Add to that pursuit the fact that our customers are constantly changing, and it’s 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 listening to our prospective customers would’ve avoided that.

Lost $12,000 by discounting — and as a result, reducing the perceived value of — our product?

A few dozen conversations would’ve made it clear that price wasn’t 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:

“You’re In” Email

Probably the only “hack” that we’re 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 we’ve ever tried (and we’ve tried some expensive tools).

This email has singlehandedly given us deep insights into the triggers that cause people to sign up for Groove, and we’ve been able to apply those to our marketing with tremendous results.

Customer Service

There’s a reason that I, as a CEO, spend more than half of my time doing customer support: it’s 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 we’ve 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.

We’ve 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, I’ve found that there’s 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.

It’s why I make it a point to talk to every single Groove customer.

If I knew then what I know now, I would have been doing this from day one.

2) Don’t 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.

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.

While we’ve 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 here’s the thing: you can’t 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 that’s why it converts: because it speaks their language, not ours.

And don’t 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 doesn’t know enough to write persuasive, final copy without testing, what hope do we have?

That’s why we test everything with Optimizely.

3) Content Marketing Is Ridiculously Effective (If You Do It Right)

I’ve 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 don’t do).

Not affiliate marketing (which we probably won’t 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.

Here’s what our growth chart has looked like:

Like many of these lessons, if I had known better, I would’ve done this from day one.

But it’s 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 that’s all you’ve accomplished.

But if your goal is to build your business through content, there’s more to consider. It’s 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.

That’s 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.

Promote the Absolute Hell Out of It

Within a few weeks of launching the blog, we had thousands of subscribers.

That wasn’t 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.

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, they’re happy to share it.

4) There Will NEVER Come a Point When You Know Enough

I’m an entrepreneur, but I’m not an expert.

I wouldn’t consider myself an expert in any of the things that Groove is good at: customer development, messaging and content marketing among them.

I might know a lot about some of those things, but the amount I don’t know will, for the foreseeable future, dwarf what I do know.

Understanding that non–expert status is the reason we’ve 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 doesn’t and we have to carve our own path.

But it’s 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 doesn’t 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 didn’t 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.

By knowing and appreciating how much you don’t 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.

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. We’ve gotten quite a few comments like this one.

For a long time, especially early on, I didn’t 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, I’ve come to look at our journey very differently.

$100,000 is a milestone. A big one, for sure.

But it’s not a finish line.

And frankly, there’s no “number” that represents a finish line for us. We’re 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 it’s something that we’ve become known for through the blog.

So with that said, here’s how we’ve decided to move forward: the blog isn’t going away, and the story isn’t over. Not by a long shot.

A New Goal: $500K in Monthly Revenue

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, we’re setting our sights on $500,000.

There’s no timeline for this: I expect our growth rate to slow down a bit, as it generally does once a business reaches various thresholds. It’s not realistic to expect 10% monthly growth forever, or even for a long time.

But we’re going to get there, and we’re 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, we’ve done, tested and learned a lot more than 60 things.

The Trello board that holds our topic ideas runs into the hundreds.

There’s still a lot we haven’t shared, only because we haven’t 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
• The email that convinces 20% of abandoning customers to stay with Groove
• How we come up with 15+ new blog post ideas every week

I’m 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. It’s the only one that’s 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 I’ve built relationships with over the past few years that I continue to learn from every day.

I’ll be testing featuring some of those voices, and their compelling lessons, on the blog from time to time.

I’m only going to feature guest posts that meet the standards we set for ourselves here.

Additionally, an update I’m especially excited about: we’ll be interviewing other founders on lessons they’ve learned on their own journeys to their first $100,000 in monthly revenue, and featuring them here.

The first interview we’re publishing will be with an entrepreneur I’ve learned a tremendous amount from: Hiten Shah, co-founder of KISSmetrics.

Finally, and importantly: this doesn’t mean I’m slowing down on content. I’m still going to be publishing every single week.

But reaching a milestone gives us an opportunity to make improvements to this blog that didn’t necessarily fit with the old narrative, and I’m excited to do even more to deliver value to our readers.

I hope you’ll 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.