A corollary of this is that internal tools that require developers to do unpleasant work or learn a non-career-advancing skill are more promising candidates for

A corollary of this is that internal tools that require developers to do unpleasant work or learn a non-career-advancing skill are more promising candidates for startups. Integrating with existing systems, especially legacy ones, is a nice example of work developers hate doing The first issue I see is that you don't know if you hate it until you're neck deep in the mud. So your selling point is probably further than where the decision will be made.