What it seemed like to me reading over the stories of Mark Cuban was that he realized (with the help of some frugal advisors) that he just made a ton of money on paper and didn't want to lose out transferring that into real actual dollars in the bank. It just seemed he had different goals than everyone else: everyone around him wanted to get as rich as possible, Cuban seemed to want to have as much money in his bank account as possible. Two very different things.