05-09-2026
Founder Psychology
A post I wrote a while back did more numbers than almost anything else I've published.
The one about AI making execution cheap and choice expensive. Roadmap of 47 items, co-founder asking whether to double down on agentic workflows, founder stuck not on building but on deciding.
A lot of people read that as a productivity problem. Ship less, focus more, the usual advice.
It isn't a productivity problem. It's that nobody on the team can say which of those 47 items is load-bearing.
Load-bearing means this: if the assumption underneath it is wrong, the company doesn't just lose a feature, it loses the round, the roadmap, or the runway.
Most items on a 47-item list aren't load-bearing. They're comfortable. Easy to build, easy to argue for, safe to be wrong about.
The one or two that actually matter are usually the ones nobody wants to name, because naming them means admitting how much rests on a guess.
I map thirteen categories of exactly this, untested assumptions a founder is carrying without knowing which ones are fatal if wrong.
Market, pricing, procurement timeline, regulatory exposure, platform dependency, and more. The roadmap doesn't get shorter by working harder. It gets shorter by finding out which item on it is actually holding the building up.
The thirteen categories, and a two minute tool that shows you your own exposure, are here: https://lnkd.in/gZgRmHgu