Five Years as a Tech Executive: What I Actually Learned
Five lessons from five years of hiring, firing, building, and occasionally breaking things.
Field notes on software, systems, and making AI do real work. Written from the seat, not the comfortable distance.
Five lessons from five years of hiring, firing, building, and occasionally breaking things.
The ones that quietly determine whether a codebase is healthy at year three.
Not a career advice post. A map of how the dots actually connected.
The workflow. The guardrails. The moments it goes wrong.
On building with LLMs where it counts, and where it breaks.
Field reports from running models on real data, not benchmarks.
Notes from the CTO seat, mostly on how small teams stay small.
Founding, fundraising, scaling, and the decisions you only make once.
Year reviews, conversations with founders, and early-career lessons that still apply.
The full archive, if you prefer chronology over topic.