ConvertKit
Est. 2014Nathan Barry almost killed ConvertKit at $1,337 a month — then saved it by hand-emailing bloggers and migrating their email lists for free, one copy-paste at a time.
▶ CONVERTKIT · 2014
CONVERTKIT · 2026 ◀Drag the handle — ConvertKit, 2014 → 2026.
“If you've got $100 in MRR then spending five hours to get to $200 MRR is absolutely worth it! You should be willing to do basically anything to get that initial traction.”— Nathan Barry, founder of ConvertKit
The ugly part. After about 18 months ConvertKit's revenue had slid to $1,337 a month, and Nathan Barry was ready to shut it down. A mentor told him to either kill it or fully commit. He committed — to the least scalable sales process imaginable.
What he did that didn't scale. He sent personal cold emails to authors and bloggers, tracked every lead across the columns of a Trello board, and offered to migrate them off MailChimp for free — literally copy-pasting subscribers between two browser windows, '$5-an-hour work,' to remove the one reason not to switch.
Now. In about a year that hand-work took ConvertKit from $1,337 to roughly $98,000 in monthly recurring revenue, and it kept compounding into a bootstrapped, multi-million-dollar business — now called Kit.