If you have nothing left to lose, then you have nothing to risk and the question is moot.

Last year, I quit my very stable job in academia to join a brand new company as the employee number 1. I think that is as far as I can go even in this hypothetical scenario.

Go hunt some bad guys around the world?

You can only imagine.

I've put it all on the line even when there was a great likelihood of losing it all.

nothing to lose => your dead => cant take risks