Ellison wants to be dominant in everything he does. On Oracle's competing with Microsoft to be the number-one software company, Ellison told 60 Minutes in 2004, "We're in second place. We're trying to catch them. They're not making it easy ... They have a monopoly. We don't. Darn it."
Source: 60 Minutes
Ellison obsessed over beating Gates for years. Former Microsoft CTO Nathan Myhrvold told Vanity Fair in 1997: "I mean, the guy’s got six billion bucks. You'd think he wouldn’t be so dramatically obsessed that one guy in the Northwest is more successful. [With Larry] it’s just a mania."
Source: Vanity Fair
He led huge changes in the America's Cup sailing competition, moving away from standard catamarans to expensive, futuristic AC72s. The boats are 13 stories tall and reach speeds of up to 50 mph.
Source: Business Insider
Team Oracle has now won America's Cup twice. Before his second victory in 2013, a thrilling, come-from-behind win, Ellison was penalized for altering a practice boat without approval. "I'm addicted to winning," he told 60 Minutes.
Source: 60 Minutes
Now Ellison has turned his efforts to another sport: tennis. In 2009, he paid $100 million to own the BNP Paribas Open and its facilities at the Indian Wells Tennis Garden.
Source: Bloomberg
Since then, he's invested some $100 million to make Indian Wells the biggest tennis event of the season. More than 438,000 people attended the most recent edition of the tournament.
Source: Bloomberg, BNP Paribas Open
In 2010, Ellison lost a bid to buy his hometown basketball team, the Golden State Warriors. "I know for a fact there was concern that I was a person who wanted to win all the time and that I would raise the prices for coaches and facilities and all sorts of other things and make it much more expensive for all the other teams to compete," he told Bloomberg.
Source: Bloomberg
Some wealthy tech executives buy vacation homes or tropical getaways. Ellison, on the other hand, owns 98% of the Hawaiian island of Lanai, which he purchased for $300 million in 2012. He plans to transform the 140-square-mile island into a model of eco-friendly living.
His main residence is a sprawling, Japanese-inspired retreat in Woodside, California. It reportedly took 10 years and more than $100 million to complete. Ellison hired a Zen priest and a team of researchers who took multiple trips to Japan before construction could start. "The rocks are supposed to look like they were placed here by the hand of God over the last million years," Ellison told 60 Minutes.
Ellison has been called "the nation's most avid trophy-home buyer" and has all but taken over entire neighborhoods in Malibu's Carbon Beach area.
Ellison owns several private planes, including a Marchetti private jet. Ellison once won a sailing race from Miami to Montego, then got in his private jet and dove down close enough to buzz the boats of his competitors. "It was an incredibly adolescent and immature thing to do," he told Vanity Fair in 1997, "and I highly recommend it."
Source: Vanity Fair
It's also been rumored that Ellison flew one of his fighter jets under the Golden Gate Bridge in the middle of the night, a perilous feat that only professional stunt pilots would attempt.
Ellison's favorite saying is a phrase from legendary warrior Genghis Khan: "It's not sufficient I succeed. Everyone else must fail." Ellison has an extensive collection of Japanese artifacts, including this set of armor that was put on display at San Francisco's Asian Art Museum.
I suppose you can say to anyone who wants to win so badly, who am I winning for? Am I winning for Oracle shareholders or is this simply a matter of personal vanity? I admit to it, mea culpa. An awful lot of it is personal vanity," Ellison said to 60 Minutes in 2004. "I think we are curious about ourselves.
Source: 60 Minutes
