What I Learned Automating Software Development (After 20 Years of Doing It Manually)

In Part 1, I told the story of building OpenLoop — an open-source feedback platform — by emailing an AI agent for 5 days. 160+ emails, $15 in tokens, zero lines of human-written code, and a working product at the end. Now let's talk about what I actually learned. What the AI Was Good At Let's start with the positive, because there's plenty of it. Scaffolding speed is unreal. Within 90 minutes of the first email, the AI had a working Astro + React + Tailwind project, a Supabase schema with six tables and row-level security, a feedback widget, public roadmap and announcements pages, and an admin dashboard skeleton. That's not a weekend project — that's a weekend project done before my coffee got cold. It follows explicit instructions well. "No Next.js, go Astro" — done. "Name is OpenLoop" — rebranded everything. "Widget takes a userId, not email" — refactored. When you're clear about what you want, the AI delivers. The problems start when there's ambiguity, but that's true of any team me