Newsletter

Lessons from 15 years of engineering leadership

What I've learned building and leading remote teams at Square, DoorDash, Mudflap, and startups before that.

Every couple of weeks, I share a practical take on something I'm working through—shipping, team dynamics, AI-assisted workflows, agentic coding. Most AI advice for engineering teams is wrong. I write about what I'm seeing work in practice.

Most teams are using AI wrong

The teams getting real leverage from AI aren't the ones with the best tools. They're the ones who rethought how work gets done.

JAN 29, 2026

The alignment problem isn't technical

Most alignment failures aren't disagreements. They're translations that never happened. Everyone agreed on words, not on meaning.

JAN 15, 2026

Smaller teams, faster learning

AI made your team faster. So why does everything feel more chaotic? The answer isn't more process — it's restructuring the unit of execution.