Mark Cuban and his cofounder Todd Wagner sold their video portal, Broadcast.com, to Yahoo for $5.7 billion in stock in 1999. He has spent the last decade and a half doing just about anything he wants. His latest antics include starring as the president of the U.S. in the movie "Sharknado 3: Oh Hell No!" and selling Dallas Mavericks merchandise with an image of his likeness using a urinal. Cuban has played with the idea of running for the real presidency.