If Barney Stinson had a tech industry idol, I’m pretty sure it would be Larry Ellison. The Oracle CEO/playboy/ship captain/fighter pilot/ego has been a legend in the world of willfully wasteful and awesome for decades. The man earns it like Steve Jobs, and he burns it like Steve McQueen, and he puts all the other partyboy pretenders to shame.
Why He’s a Geek: He’s managed to retain interest in what is really the least sexy segment of the technology industry.
Why we envy him:
- He won the America’s Cup and is bringing it to San Francisco.
- He once owned a 456-foot yacht that was too large to dock at most ports.
- He recreated a traditional Japanese estate in Northern Calif., because he could.
- When his private jet got boring, Ellison bought a MIG-29 Russian fighter (though the ATF said he couldn’t bring it to the U.S.).
- He gives $100,000 Acuras as gifts.
- He dropped $40 million on a neighbor’s house because he didn’t want it to obstruct his view.
- Not to be outdone by Richard Branson, Johnny Depp, and other celebs with small private islands, Ellison is buying a big one. He’s grabbing a 98% stake in the Hawaiian island of Lana'i, which is more than six times the size of Manhattan. Yup. The whole island.