Michael Dell vs. Larry Ellison

Dell got his start at 19 selling computers out of his University of Texas dorm room, grossing $80,000 by the end of his freshman year. Dell's MSD Capital owns the Four Seasons Maui, plus indirect stakes in Applebees, IHOP, Calvin Klein and reportedly Grand Central Station.

Ellison never finished college. He started out building databases for the CIA. Daughter Megan has financed films such as Zero Dark Thirty and American Hustle; son David produced mainstream movies like The Terminator and Mission: Impossible".