But I can't help but think about the 9 founders of other companies that had the same resolve in the same situation, but things did not work out so well.
All you other people thinking about going for broke need to be ready to hit bottom and build yourself back up afterwards, because 9 times out of 10 that's what will happen. Or, even better, first put yourself into a situation where you don't need to go for broke to give yourself an excellent chance at success.
I think this is why a lot of crazy big startups come from younger people, they can afford to go for broke before they have a family and other obligations, because the worst that can happen is they are left with nothing, then they settle for a high-paying job at a big tech company and 2 months later they can afford a new car.