How I built a $30M company


Hi Reader,

10 years ago, I started a web app challenge where I set out to create a startup that would generate recurring revenue.

That startup ended up being ConvertKit.

But ConvertKit wasn’t always what it is today. There were a lot of ups and downs—not just within the company: with me personally.

The team approached me with the idea of making a documentary about my story.

I said no.

Part of the reason I didn’t want to make a documentary is I don’t like being in the spotlight. The other reason I gave was that I don’t want it to seem like ConvertKit is all about me (because it isn’t).

But deeper down, the real reason I didn’t want to make this documentary is I knew I’d have to talk about what was really going on behind the scenes. I couldn’t hide behind a fluffy creator story. I knew I would have to get real.

And getting real meant telling stories I didn’t want to tell.

video preview

Watch documentary »

Let me know what your takeaways are.

—Nathan

Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

Read more from Nathan Barry
video preview

Hey Reader, A lot of the rules we built our work habits around made sense before AI. Some of them held up for decades. Right now, in early 2026, I think it's worth asking which ones still do. Here are five things I think are worth throwing out: 1. Detailed mid-level planning Knowing where you're going is still important. But the master plan that used to live between the destination and the work itself is mostly just a way to delay starting. Before, mapping out how all the systems connect just...

Stack of balanced stones on a rocky shore

Hey Reader, If I say something dumb, I'm probably still replaying it in my head 11 years later. Just me? It’s an exhausting feeling. You're not really solving anything, you're just reliving the moment over and over. And when you're building a business, there's always something new to add to the pile. After a while, it gets hard to tell which things actually need your attention and which ones you've just been dragging around. Start by writing everything down. When a worry stays in your head,...

Hey Reader, Attending a conference is one of the highest-leverage things you can do as a creator. Three days in person will accelerate a relationship more than six months of talking online. The people you meet at events can often become your business partners, collaborators, and even some of your closest friends. But only if you know how to use the time. Here are my top 10 tips for getting the most out of conferences: 1. Choose the right conference Not every conference is worth your time. The...