Archive
2026
- Holding the Whole
AI dissolves accidental complexity at speed, but essential complexity — the question of whether it all adds up to something good — remains stubbornly human.
- The Architect's Exit
Kissinger defined a revolutionary power as one that rejects the legitimacy of the order it inhabits — then spent his career building America's. What happens when his framework fits its own architect?
- Soft Landings
I spent almost two decades loyal to one airline alliance — then the program changed its rules, and I started gliding away so quietly they'll never know I left.
- Staying in the Water
What building a bootstrapped company actually feels like after nearly a decade — not the VC default, not the indie hacker fantasy, but the uncomfortable middle where most of the building happens.
- Blast Radius
AI can reproduce substantial software systems. The moat against substitution scales with the blast radius of failure — but the line between what's safe and what's vulnerable keeps moving.
- The Absorption Gap
Four scenarios for how AI gets absorbed into the real world — and why all four are happening at once.
- Writing With Machines
I've always used writing to think. This time I'm using AI to write — not to produce text faster, but to think harder.
- Collapsing Cycles
Cycles are getting shorter everywhere — in careers, in technology, in how organizations work. A decades-old Marine Corps doctrine saw it first, and its insights about coordination under pressure feel uncomfortably relevant to building software with AI.
- The Perpetual Gale
Cloud eliminated the infrastructure barrier. AI is compressing the labor one. The pattern is familiar.