Having money is more than your checking account balance. If you ran out of money, did that mean foreclosure? repossession? homelessness? starvation? If not, then you weren't broke. Obviously I can't speak to your situation, and if you're a true bootstrapper, then kudos. However, I think you can agree there's a ton of 19 years old running around driving the cars mommy and/or daddy bought, with the iPhone and MBP also purchased by their parents. They can totally go for gold and fail, and still have somewhere to live and try again.