The Million Dollar Tweet: 8 Lessons to Grow a Successful Business

Nathan Barry bootstrapped ConvertKit to $1 million monthly recurring revenue in a little over five years. Here are 8 critical lessons he learned along the way.

Nathan Barry is the founder of ConvertKit, and a good friend of mine. Just the other day he tweeted:

Yesterday @ConvertKit hit $1m MRR. Thank you so much to everyone who has helped along this journey! We’ve now got an incredible team of 34 supporting 18,872 customers.

— Nathan Barry (@nathanbarry) March 19, 2018

This is a huge milestone, and I want to give huge kudos to Nathan and his team for achieving it!

[Full disclosure as we dive in to this post: I am both an affiliate and an advisor for ConvertKit, and I do earn a commission if you choose to use my affiliate link (the links back to ConvertKit on this page) and stay on after the free trial. I’m proud to be an advisor, so if you have any questions about the product, please let me know!]

Now, if you don’t know what MRR is, it’s monthly recurring revenue. That means ConvertKit is now making one million dollars per month, and it took them exactly 1,902 days to get there.

After sharing this exciting tweet, Nathan followed up on Twitter with some thank-you messages for the people who helped him and ConvertKit reach this milestone. In these tweets, he talked about the eight specific lessons he learned from these folks that have helped his business grow and succeed.

In today’s post, I wanted to share those eight lessons Nathan and ConvertKit followed to reach this amazing milestone. These lessons are ones you can also take with you as you build your business, no matter what kind of business it is.

Lesson 1: Go All In

One of the people Nathan credited for the success of ConvertKit is Hiten Shah, the amazingly successful entrepreneur who’s founded companies like KISSmetrics, Crazy Egg, and Hello Bar.

About a year and a half into ConvertKit, Nathan was at a conference in Las Vegas, where he was having dinner with Hiten and a few other people. He and Hiten were walking and talking on the way back from dinner when Hiten stopped, looked at Nathan, and said, “You know, Nathan, I’ve been thinking. You should shut down ConvertKit. You’re a year and a half in. You’re still at $2,000 a month in revenue. It hasn’t taken off, and you’re going to be successful at other things. So you should shut it down and move on.”

Nathan was stunned. But Hiten continued, “Or you can give it the time, money, and attention it deserves and build it into a real business. But right now you’re trying to run a few different side projects, and the focus isn’t working for you. So you need to either go all in, or shut it down.”

Nathan thought about this for the next few months, then finally decided that ConvertKit wasn’t going to go anywhere unless he made it go somewhere. That’s when he made the decision to go all in. At the time he had another business,, where he sold books and courses. He stopped working on, then took all his savings and put it into ConvertKit. He hired a full-time team, and started doing more direct sales. The other big thing he did was pick a niche for ConvertKit, focusing on providing email marketing for professional bloggers. (Remember, the riches are in the niches!)

From that point on, ConvertKit has only looked up. It was a lack of single-minded focus that was holding the company back from reaching its full potential, but once Nathan made the decision to focus only on ConvertKit, the sky became the limit. If you want your business to reach the next level, you need to be willing to go all in.

Lesson 2: Build a Great Product

Nathan also credits ConvertKit co-founder David Wheeler for helping ConvertKit become a great product. This is another one of the biggest reasons why ConvertKit has been so successful. You can have all the pieces in place to sell and support your product—the tactics, the strategies, the team, the influencers to promote it—but if that product isn’t great to begin with, it’s not going to be successful.

Thankfully, ConvertKit is a great product. What drew me to ConvertKit in the first place was the fact that it’s a product that just works. It’s easy to use and reliable, and most importantly, it fits into everything I’m doing in my business too. It’s why I recommend ConvertKit as an affiliate, and why I’m an advisor for the company.

So make sure, as much as anything, you build a great product.

Lesson 3: Get Feedback

Early on in the process of creating ConvertKit, Nathan sought feedback from a number of influencers on how to build the product the right way. Nathan called out two people—Ryan Delk and myself—as key influencers, people he connected with early on to get direct feedback on how to build his product the right way. Since I was already in the blogging space when Nathan reached out to me, I was able to contribute a lot of valuable feedback about what would make this product successful. And Ryan, having so much experience in the startup world, was able to do just the same.

So the big lesson here is that you cannot do this alone. And because of that fact, you need to connect with the right people who can give you honest feedback that’ll help make your product the best it can be.

Lesson 4: Be Transparent

Another key lesson Nathan has applied since the beginning is the idea of being transparent. Much like I do on Smart Passive Income with my income reports, Nathan does the exact same thing—just with a software company. He’s connected ConvertKit’s metrics to a site called Baremetrics, where anyone can track the company’s income growth, all the way back to the beginning. You can even see new customers signing up in real time.

When you do business with other people online, whether it’s with individuals or other companies, trust is a crucial factor, and there’s no better way to build that trust than to be fully upfront and transparent. That’s exactly what Nathan has done with ConvertKit.

Lesson 5: Focus on Sales

The next big lesson is that you need to really focus on sales if you want to grow. Nathan credits Darrell Vesterfelt, who he hired back when ConvertKit was starting to focus heavily on sales. By putting a lot of time, effort, and money into building an effective sales team and process, Darrell was able to bring the company from $100,000 to $500,000 in MRR.

Now, sometimes when you’re starting a business, you just don’t have the resources to do that. In that case, the most important thing is to focus your resources wisely so you can land your first big customer. This is why Nathan also thanks Joel Runyon, who was that “first big customer” for ConvertKit.

Focusing on sales also means not just finding customers, but influencers who can help bring your product to a wider audience. Not to toot my own horn too much, but I also helped push ConvertKit out there in a big way as an affiliate. I know that with my large audience and the trust I’ve built with them, if I promote a product I really believe in—like ConvertKit—it’s going to help that company grow. So, Nathan very strategically had coffee with me one day a number of years ago. He showed me the product and how great it was, and helped me actually get started with it. It became obvious to me at that point that ConvertKit was something I needed to push out to my audience too.

So, focus on sales, both by finding new customers directly and via influencers who can help you do the same.

Lesson 6: Build a Great Team

When ConvertKit started out, the company had a really small team. As Nathan has grown and scaled the company, it’s grown to thirty-four people. I’ve gotten to know a lot of the ConvertKit team well at events, and they all say nothing but amazing things about being a part of this company. They absolutely love what they do. A lot of them get to work remotely, they go on retreats, and do a lot of fun things together. And most importantly, they’ve all told me that they feel like they’re a part of the ConvertKit family.

So the big lesson is, as you’re building a team, make sure you’re also building the company for the team. Create a culture and an environment that people will love to be a part of, because that will really amplify your mission.

Lesson 7: Care About Your Customers

ConvertKit does an excellent job of educating their subscribers along the way as they’re learning to use the product so that they’ll find success with the product. But this support and care starts right after the moment of purchase—and it’s something you can do in your business too.

One thing I’ve always loved about ConvertKit is they don’t just have people sign up then forget about them after that point of purchase. In fact, right after the purchase is when the fun starts with ConvertKit. Right after you sign up, a member of the ConvertKit records and sends a custom, personalized video greeting, using an app called Bonjoro, welcoming you to ConvertKit and letting you know they’re there to support you as you’re getting started. It’s an incredible way to welcome someone to the fold and make them feel like part of the family. And it takes just thirty seconds to do.

How has creating these individualized onboarding videos helped the company’s metrics? It’s actually helped decrease churn in the company—people who don’t continue their subscription—by a whopping 16 percent.

Lesson 8: Be Grateful

Gratitude—being appreciative of the journey and how far you’ve come—is a really important factor in your success as a business owner. One thing that’s been apparent since the beginning is the fact that Nathan is grateful for his experience—for the people who he’s worked with, and most importantly, for his customers.

It’s really tough when you’re in the trenches, grinding away on your business, and easy to forget why you’re doing this in the first place. But when you remember why you started, and can appreciate the journey and the small wins that eventually lead up to bigger ones, it can make a huge difference.

I hope this post has pushed you to continue moving forward in your business, no matter where you’re at with it. Very few businesses become overnight successes, and ConvertKit under Nathan Barry definitely wasn’t one. But by applying these eight lessons, Nathan has been able to create a great company with a great team, a great product, and great customers. And so can you.

By the way, if you’re interested in checking out ConvertKit as a tool to manage your emails, here’s a demonstration below.

Also, be sure to click here to get a 30-day free trial to ConvertKit to try it out!

Please note that I am an affiliate for ConvertKit and do earn a commission if you choose to use this link and stay on after the free trial. I’m also an advisor for the company, so if you have any questions, please let me know!

Share this post

  • Pat Flynn

    Hi, I’m Pat, founder of SPI and host of the Smart Passive Income Podcast. Let’s continue the conversation over in our communities.

Get Unstuck in just 5 minutes, for free

Our weekly Unstuck newsletter helps online entrepreneurs break through mental blocks, blind spots, and skill gaps. It’s the best 5-minute read you’ll find in your inbox.

Free newsletter. Unsubscribe anytime.

Join 135k+