Ruby on Rails Lost Its Superpower
Rails gave me a career. But the users and programmers it was designed for have changed, and other stacks now offer the same head start.
Writing on software design, AI and startups.
All of my long-form thoughts on programming, leadership, product design, and more, collected in chronological order.
The Token Compression Illusion: Why I'm Skeptical of RTK
RTK promises dramatic token savings for coding agents, but raw terminal compression is not the same as cheaper, safer, or more accurate software engineering.
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.
Why I Open-Sourced My Hardened *arr Stack (and What Most Compose Files Get Wrong)
Most self-hosted *arr compose files are ticking time bombs: flat networks, fake kill switches, no health checks. Here is how I built one that actually holds up.