
My personal Substack
| Platform | Pricing | Only free issues | Publishes | Weekly | |
|---|---|---|---|---|---|
| Issues | 14 | Founded | 3 months ago | Last Issue | 4 days ago |
| Active | |||||

There’s a kind of debt nobody puts on the board.
Not technical debt — most teams at least know that exists, even if they don’t pay it down. This one is quieter. It accumulates in the gaps between what your system does and what anyone can e...
I didn’t set out to build a team. I set out to stop context-switching so much.
Financial planning in one window, codebase in another, email in a third. All of it requiring the same brain at different altitudes. The AI was supposed to help...
The systems still standing after thirty years didn’t survive because they were perfect. They survived because they were fit.
The first eligibility file we ever received had a person with the last name Null.
I thought it was funny....
The problem isn’t that AI gives bad opinions. The problem is that it gives agreeable ones.
Ask AI to review your plan. It reviews it. Identifies a few concerns. Frames them carefully. Suggests one or two improvements. If the plan is solid,...
There’s a version of the AI story where experience is a liability.
You’ve been doing this for twenty, thirty years. You have instincts built from a thousand decisions, a thousand failures, a thousand systems that worked until they didn’t....
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