I believe Adam Neumann was ambitious, with a "unique leadership style".

I get the feeling some older VCs are playing out their mid-life crises by vicariously enjoying the lifestyles of their "crazier" founders. Perhaps it would be better for the world if they just bought that motorbike or sports car instead.

It's hard to do when the VC next door just bought a super-yacht that can launch its own mini-yacht, yo.

It might also be a simple cases of selecting the in-group for funding rounds. That is, "they're like me, so I'll give 'em cash".

Can't get any more ambitious than Elizabeth Holmes and Theranos.

If only ambition correlated with competence.

I'd argue that you can hire employees for intelligence and other assorted skills but without an ambitious founder few startups would succeed.

It's more that the less ambitious founders would be willing to "settle" for decent-but-not-unicorn outcomes for their companies, which are not the outcomes that VCs are looking for.

The VC-funded startup model will gladly have 99 out of 100 founders go bankrupt as long as the 100th starts a unicorn. Investors will push companies to take existential risks to achieve growth at all costs. Obviously, most founders are not OK with these odds and only the most delusional (if you want to spin it negatively) or ambitious (if you want to spin it positively) will go for it.