Never been homeless, but I've had many times lately where I had $0 to my name. Went from a broke programmer at 18 to making a couple million a year at 21 after discovering Blackhat marketing. I made so many stupid decisions which cost me my business I had built up, and now, 6 years later I'm a couple months away from filing bankruptcy with almost a million in debt. I've lost every single thing I own of value. The downward slide has been downright rough but it's made me a better person.. My outlook on life and money has totally changed, and I know that if I keep working hard and putting myself in a position to succeed I will be able to duplicate my success even in a WH business.
As of right now, I haven't made anything in about 7 months, but I've been coding 6-7 days a week, many times 10+ hours a day during that time. Maybe I was too ambitious, and hopefully this damn project won't sink me (i.e. make me homeless) before I can get it completed and making money. But I do know one thing, I've never been homeless before and I always seem to pull something out of my ass in the nick of time.
Being at your lowest point motivates you fight that much harder to pull yourself back up, just like when those people laughed at you sleeping in your car. Damn, I can only imagine how that felt.