No. 2: Larry Ellison
Net Worth: $43 billion
Oracle CEO Larry Ellison likes to fly fighter jets and launch America's Cup sailboat racing campaigns. A native of New York City, Ellison grew up in Chicago and moved to California in the late 1960s. He would later become a close friend of the late Apple co-founder Steve Jobs. Ellison's expensive life-style is well-documented. Ellison owns hundreds of millions of dollars of real estate around the country, including 98% of Lanai, Hawaii's sixth largest island. Ellison also appeared briefly in the film Iron Man 2.