Steve Ballmer vs. Michael Dell

Ballmer and Microsoft cofounder Bill Gates were classmates at Harvard. Ballmer created a website called USAFacts.org for people to look up and understand where the government is spending money.

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.