Nathan Barry grew up in Boise, Idaho, dropped out of college, and started building websites. When the 2008 financial crisis killed his freelance work, he took a contractor job at a software company. By 2012, he had pivoted to self-publishing. His first ebook, The App Design Handbook, launched to an email list of 800 subscribers and earned $12,000 on day one. Two more books followed. By the end of 2013, he had made $256,000, with nearly $200,000 coming from his three books. He was 23. And the dominant sales channel was email, not social media.
On January 1, 2013, Nathan publicly announced "The Web App Challenge" on his blog. The rules: build a SaaS from scratch, reach $5,000 MRR in 6 months, invest no more than $5,000 of his own money, and spend no more than 20 hours per week. The idea: an email marketing tool for bloggers and authors. He was frustrated fighting MailChimp to implement content upgrades and follow-up sequences, so he decided to build a tool with those best practices baked in.
The challenge was technically a failure. After 6 months, ConvertKit had only $2,480 MRR. He didn't hit $5K MRR for 26 months, not 6. And he invested $55,000, not $5,000. But Nathan called it "a massive success" because it forced him to ship and find real customers.
By mid-2014, about 15 months in, ConvertKit had stalled. Nathan was still earning $250,000 per year from ebooks and was giving ConvertKit only part-time attention. MRR flatlined around $2,000, then began declining. By October 2014, it hit $1,207. His friend Hiten Shah (co-founder of Crazy Egg) told him bluntly: either focus full-time or shut it down. Another friend directly advised him to kill the company.
Nathan chose to double down. He shut down his profitable ebook business entirely. "I'm not good at doing two things at once." He invested $50,000 of personal savings and hired a developer and a support person. Then he did something nobody expected: he started personally emailing bloggers, one by one. Not pitching ConvertKit. Asking what frustrated them about their current email tool. He went hyper-specific: not "bloggers," but paleo recipe bloggers, then paleo recipe blogs run by women. The logic: the smaller the circle, the more likely prospects know each other. Get one, and word of mouth does the rest.
Most conversations ended with "sounds great, but switching is too much work." So ConvertKit started doing free concierge migrations. They moved subscriber lists, tags, automations, everything. This removed the biggest barrier. MRR grew from $1,207 in October 2014 to $5,020 by March 2015.
The real inflection came from Pat Flynn of SmartPassiveIncome.com. Flynn joined as an advisor when revenue was under $500K/year. His promotion alone drove $5,000 MRR in a single month. Between 2015 and 2017, Flynn earned $350,000 through ConvertKit's 30% recurring affiliate program. Then in 2016, ConvertKit ran 150+ webinars in a single year. Same presentation, over and over, 20-30 per month. The Pat Flynn webinar alone drove 1,000 signups in 24 hours. This single channel drove MRR from $98K to $625K in 12 months.
In 2021, Spotify offered to buy ConvertKit for hundreds of millions. Nathan said no. In 2024, he rebranded to Kit. Today, Kit serves 600,000+ creators including Tim Ferriss, James Clear, and Andrew Huberman, processes $2 billion+ in creator earnings, and generates $43M+ ARR. Still bootstrapped. Zero VC. Built on Rails, MySQL, and personal emails to paleo bloggers.
In 2021, Spotify reached out to buy @ConvertKit for hundreds of millions. I said no. Here's what we did instead: