The Cuban Family – $3.9 Billion

Without a doubt, there are few names in the investment world bigger than Mark Cuban. After all, how many other investors and entrepreneurs have become Hollywood icons as well? The best part of all? Cuban worked his way up from a working-class family, making his incredible success even more admirable. He once lived in a three-bedroom apartment with eight other roommates, just to make rent!

Early ventures in software put Cuban on the path to success in the 80s and 90s, eventually resulting in his ownership of Broadcast.com, which Yahoo! ultimately bought for $5.7 billion! From there, he founded 2929 Entertainment, which has produced hits like George Clooney’s Good Night, Good Luck, and purchased the Dallas Mavericks basketball team.