[throwaway74829]

Have you gone down this route?

I think the biggest issue deep generalists fall into is that they can be above average in the entire stack, but not exceptional enough to make the cut for a specialized role in any single thing (i.e the vast majority of publicly advertised roles).

Going down “specialized in boot-strapping startups” route is an interesting remedy. I would imagine the only way to find these opportunities is word of mouth.

[tyurok]

I didn't go through, but have seen quite a few. It's indeed a less advertised position since it might be more common in smaller companies (less money/reach) and it might be a founding opportunity (less pay, higher risk), so it goes under the radar compared to very specialized positions.