I agree with what you are saying, another thought I have, which could be incorrect, is that there is a reason that so many second startup attempts by founders a

I agree with what you are saying, another thought I have, which could be incorrect, is that there is a reason that so many second startup attempts by founders are successful. I think it has to do with general experience and many other things but one of the big ones is that a first startup that does "modestly" well or has a decent exit can setup a founder in a place where they have more breathing room financially for the next, a 20k chunk of cash gives a lot of breathing room for savings/disaster that takes stress off. I almost had it with my talent booking agency (which was bootstrapped over nearly 4 years), and then the money we were making went to a co-founders head and he blew up the company after developing a coke/sex addiction that unhinged his mental health, he couldn't handle the money and the access it gave him and that was at ~50k mrr.... it was like a whole world opened briefly opened up for me before getting crushed. For me personally I experienced that having an income source not dependent on personal labor has a very strong benefit for being able to focus on execution and setting the company up strategically, it also let me hire devs who I trusted and had a compounding effect on speed of development. I like to think I am a good dev, but I'm not as good as 3-4 good devs, I can't afford that hiring in my current state. For the homelessness thing in particular, well funded also means well connected, it means you have buy in and backers and vested people going to bat for you. It means I don't have to do all the dev on my own. That's my current thinking at least.