Michael Bloomberg vs. Michael Dell

In 2018, Bloomberg pledged $1.8 billion to Johns Hopkins University, his undergraduate alma mater, adding $1.5 billion he had already given the school. As a teenager, Bloomberg worked at an electronics company in Cambridge, Massachusetts.

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.