Vince started out in a pretty good place because of his dad. He made some good decisions and made more money, but he was also put in a place where he could make those decisions. When things he had done failed (XFL, World Bodybuilding Federation, etc) he always had the business that his family built and that he took over to fall back on. When people are rich they can afford to do things that will fail or not make money because the losses from it won't really hurt them in the long run. It's the equivalent of me buying a lottery ticket. If I win, great. If I don't, those few dollars won't really set me back. It's just on such a large scale that it's insane.