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Joe Leo, Founder @ Def Method | When Breaking Things Is Expensive

2026-04-03

Joe Leo built a Rails consultancy for 12 years — here's what he'd do differently

Mike sits down with Joe Leo, founder of Def Method and co-author of The Well-Grounded Rubyist, to talk about what it really takes to run a software agency long-term — and why niching down, building in public, and falling in love with the work matters more than chasing the big exit.
They get into:

Why Def Method went all-in on Ruby on Rails modernization (and why 2025 is their best quarter in years)
The real reason layoffs aren't about AI efficiency
What agentic security actually looks like — and why we don't have a model for it yet
How multi-agent workflows and docs-driven development are changing the way they ship
Why services businesses may actually be bigger in the age of AI, not smaller

Joe also shares how two years of posting on LinkedIn with zero signal eventually turned into a real pipeline, why he switched from Claude Code to Codex, and the one piece of advice he gives every engineer starting out today.
📚 Book rec: Mindset by Carol Dweck
🎙️ Check out Joe's podcast: Ruby AI Podcast
🔗 Find Joe on LinkedIn: https://www.linkedin.com/in/jleo3/

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