Jeff Bezos vs. Michael Dell

Growing up, Bezos worked summers on his grandfather's ranch repairing Caterpillar tractors. Bezos met Google founders Larry Page and Sergey Brin in 1998 and managed to become one of the company's first angel investors, putting in an estimated $250,000.

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.