Episode
I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)
- Podcast
- How I AI
- Published
- Aug 24, 2026
- Duration seconds
- 2653
- Processing state
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Summary
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 goal, and what to optimize for instead — Brought to you by: WorkOS —Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Jira AI SDLC —Get your tokens’ worth with Jira — In this episode, we cover: (00:00) Introduction to Ryan Carson (02:55) Ryan’s update: Untangle, the divorce PMF pivot, and B2B growth (07:35) Ryan’s current Devin stack: folders, P0 threads, and the paper list (16:29) Watchdog playbook: account monitoring across every firm (18:09) Managing agent decision fatigue: Ryan’s method vs. Claire’s (20:32) Producing more output does not make a better product (22:47) Using cloud a…