What he wouldn't easily admit was how this successful business was his sixth try, having blown what, to me, seemed like a small fortune on each of his previous attempts. He always had a rich family to fall back on, living off of them while he dreamed up his next attempt to "add value." Finally (inevitably), one of them stuck, so obviously this is proof that he's self-made and his success was due entirely to his own "hard work".
If you grow up poor without a fallback, you pretty much have one shot, if you're even able to save up for that one. You mess up, and you're pretty much hosed. On the other hand, with an infinite money cushion, you get to keep shooting until you hit the target. What's the saying? Going from $0 to $1M is almost impossible--going from $1M to $2M is almost inevitable.