What risks would you take if you knew you had nothing to lose?

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