Writing on software design, AI and startups.

All of my long-form thoughts on programming, leadership, product design, and more, collected in chronological order.

Ruby on Rails is Dead (2026 Edition)

Part 1 of a structural critique of Rails in 2026: the magic that made Rails dominant also became an architectural cage for the stateful, real-time web.

Dear Codebase: A Letter From Your Coding Agent

Ten requests from an agent to the codebase it works in — local reasoning, visible boundaries, one way of doing things. None of them are new. All of them matter more now.