I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)

I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)

August 24, 2026 · 44 min

About this episode

Ryan Carson shares insights from his experience as a solo founder and his use of AI tools in his business.

Ryan Carson is a five-time founder and the current solo founder of Untangle, a B2B SaaS platform for family law firms. Before Untangle, he co-founded Treehouse, an online coding education platform, and has spent the better part of two decades building and leading tech companies. He’s active on X, where he shares his solo founder journey in real time, including what he actually spends on AI tools each month. What you’ll learn: Why Ryan manages 15 concurrent Devin agents with a folder system and a piece of paper, not a dashboard The Watchdog playbook: what he built to replace a customer success team across every law firm account How his LAN PR skill closes the loop on 40 daily PRs without a QA team reviewing a single one Why he moved off local agents almost entirely, and the one situation where he still reaches for Codex The design workflow we’re both using: Claude Design into a Markdown spec, then Codex to build the real thing What he found when he got away from his computer and met a real customer, and why it changed his entire product direction How he’s hiring his first engineer without a single phone screen or interview Why we both think more AI output is actually the wrong…

Sponsors

WorkOS, Jira

More episodes of How I AI

Explore listener stats, chart rankings, contacts and more on the How I AI podcast page.