Writing on how mid-sized businesses make technology decisions — what to build, what to buy, what to drop, and how to think about the next 18 months.
Founders carry the roadmap in their heads. The team executes against guesses. Three months in, everyone is doing slightly different work toward slightly different goals.
The technology debt you can see is the easy kind. The dangerous kind is hidden in vendor relationships, license assumptions, and the dependency you stopped reading the changelog for.
The build-vs-buy debate is usually a vibes argument. A simple framework — three questions — keeps it from going in circles.
In a slow-growth year, the wrong things get cut: the operational layer that keeps the business alive, while the optimistic projects that aren't earning their keep stay funded.
