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ConvertKit: The Side Project Nathan Barry Almost Shut Down

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ConvertKit: The Side Project Nathan Barry Almost Shut Down

Nathan Barry ran ConvertKit as a side project next to his book business. After 22 months it had fallen to $1,300 a month. Then he went all in and it took off.

Stacks of design books beside a row of paper envelopes moving towards a laptop

Key moments

ConvertKit, now Kit, is an email platform for creators. Nathan Barry started it in January 2013 as a side project next to his book business. After 22 months it had shrunk to about $1,300 a month. He then dropped everything else for it, and it grew to tens of millions in annual revenue.

A designer who wanted out of his job

Barry is a designer and developer from Boise, Idaho. In 2010 he was working at a company called Unity, where his boss put him on a team building an iPad app in time for the iPad’s launch.

He started blogging in 2011 with a clear goal: to make enough money online to quit his job. His first real side income came from an iPhone app he built while learning to code. He quit his job in late 2011.

In 2012 he wrote his first ebook, The App Design Handbook. It made more than $12,000 on launch day and over $20,000 in its first two weeks. A second book, Designing Web Applications, followed. Within a few months, books and courses had become a full-time income.

The Web App Challenge

The books had one weakness. They paid in bursts. Each launch brought in a big day of sales, and then income tapered off until the next one. Barry wanted something that paid every month.

On December 31, 2012, he announced a public experiment on his blog: The Web App Challenge. The goal was to build a software product and grow it to $5,000 in monthly recurring revenue within six months.

In January 2013 he bought the domain convertkit.com for under $10 and started building an email marketing tool for people like himself: authors and bloggers who sell products to an audience.

Six months later, ConvertKit was earning about $2,000 to $2,500 a month. Not the $5,000 he wanted, but a real start.

Two years as a side project

Then it stalled. ConvertKit had always been the side project. The books and courses were still his main business, and they kept doing well. When growing the software got hard, he lost interest and cut back to working on it part time.

Barry later described the problem in plain numbers. The same effort that made $1,000 from books and courses would add maybe $50 a month to ConvertKit’s revenue. Every week, the logical choice was to spend his time on books.

In a March 2015 post, he summed it up: treating ConvertKit as a side project “just wasn’t working.” By October 2014 he had been running it for 22 months. Revenue had fallen from around $2,000 a month to about $1,300, and the product was losing more money each month than ever.

All in or shut it down

A friend told him he had two options: shut ConvertKit down or go all in. Barry chose to go all in. He stopped selling books and courses and let that income drift down on its own.

He also changed how he sold the product. Instead of waiting for creators to find ConvertKit, he went to them directly. He offered to move bloggers’ email lists from their old provider to ConvertKit for free, doing the migration himself. ConvertKit later called these concierge migrations and did them for hundreds of customers.

It worked quickly. By the end of October 2014, monthly revenue had grown 23% to $1,646. By March 2015 it had passed $5,000, the target of the original challenge, about two years late.

From side project to Kit

After that, growth came fast. Within about a year of going all in, ConvertKit reached roughly $1 million in annual recurring revenue. Barry added an affiliate program and webinars with partners, which suited bloggers who wanted a steady income of their own.

The company stayed bootstrapped. Reported figures put its annual recurring revenue at about $36 million in 2023. In October 2024, ConvertKit rebranded as Kit and moved to kit.com.

Barry has kept sharing the company’s numbers publicly, the same way he shared the revenue of his first ebook.

What the ConvertKit story shows

  • A side project can lose to your main income. As long as books paid better per hour, ConvertKit kept getting the leftover time.
  • The decision mattered more than the idea. The product barely changed in 2014. What changed was how much of Barry it got.
  • He built for himself first. ConvertKit was designed for creators who sell to an audience, which is exactly what Barry was doing.
  • Doing things that do not scale got it moving. Free, hand-done migrations brought in the first wave of customers when nothing else had.

More businesses like this one are in SaaS companies that started as side projects, including Gumroad and Plausible Analytics.

Frequently asked questions

Who founded ConvertKit?

Nathan Barry, a designer and author from Boise, Idaho. He started it in January 2013. The company is now called Kit.

Was ConvertKit a side project?

Yes. For its first 22 months it ran alongside Barry’s main business, selling design books and courses. He only went full time on it in October 2014.

How low did ConvertKit’s revenue fall?

To about $1,300 a month in October 2014, down from around $2,000 a month in 2013. It was losing money at that point.

What turned ConvertKit around?

Barry stopped selling books and courses, worked on ConvertKit full time, and moved customers’ email lists over from other providers for free. Revenue passed $5,000 a month by March 2015.

Sources

Noah Reed Avatar