Good lord why? There are so many other tech hubs where housing is reasonable. How are you supposed to do your most inspired work if you can't get a decent night's sleep.
Not to say that you shouldn't invest almost everything, and this is a cool hack, but it's not sustainable, at least emotionally.
Are you? Are you really sorry?
Kinda like saying "have a nice day" to somebody who was just rude to you.
The main difference here is that I assume he is making decent money. More than you would expect of someone that is "really" homeless anyway.
So why keep up the charade if you're out of the weather anyway?
And a young person can wind up living in their car despite playing to expectations and not pursuing their dreams. That and short is just the way life is.
Sure, maybe silicon valley is slightly better, but it doesn't look like a particularly compelling advantage, certainly not anything close to the divide between doing theater in NYC and doing it in Milwaukee.
On the internet, nobody knows you're a dog, and few people care where your doghouse is.
/my impression/ is that it's similar when getting VC money, but I don't have direct experience with that like I have with consulting.
People you meet in person, in my experience, are more likely to do business deals with you, and you are going to run into more people of the calibre you want to have partnerships with in this area than anywhere else.