And he's poured at least as much money into yacht racing – trying to win sailing's Super Bowl, the America's Cup.
The only problem is that Ellison's boat finished second in last year's race. And his company is currently the world's second biggest software maker.
Now, you may not care if you were second and had $18 billion. But Ellison does care, which may be why some people consider him to be the most competitive man in the world. Correspondent Charlie Rose reports.
It's a perfect day on San Francisco Bay, and Ellison's boat is the USA-76. His opponent is named Alinghi, and it's the boat that beat him in the America's Cup.
Ellison invited 60 Minutes along for the race, and we wondered just how much he'd spent so far chasing the cup. The answer: $100 million.
Is it worth that much to him to bring home the America's Cup? "It's not worth that much to lose the America's Cup," says Ellison, whose boat will be the main challenger at the next America's Cup – three years away.
But for now, the boats battle in a series of exhibition races. And in this race held in San Francisco, Ellison was out to win.
"I'm addicted to winning. The more you win, the more you want to win," says Ellison.
In Silicon Valley, Oracle's glass towers are called "Larryland." And the 59-year-old founder built his empire on software that manages data and information for business and government.
The software is something like a giant brain, allowing the CIA, which was Oracle's first customer, to sift through intelligence gathered from all over the world. A company like Ford uses it to retrieve and analyze data on anything from car sales to employee benefits. And you've probably used Oracle software yourself at your bank's ATM, or booking a plane ticket, or buying a book over the Internet.
It's a huge business that has made Ellison very rich. In fact, briefly, for just a month, he was even the world's richest man. "That was one hell of a month," he says, laughing.
And he revels in it, because Ellison becoming No. 1 meant that somebody else had to be No. 2. And that somebody was Bill Gates, whose Microsoft towers over all the competition, including Oracle.
"It's an exciting game that's going on right now. And it to some degree ,it is a game. Microsoft's in first place. We're in second place. We're trying to catch them. They're not making it easy," says Ellison.
"They're an extraordinary company. They're the most important company on earth … We're far behind. They're three times bigger than we are. They have a monopoly. We don't. Darn it."
Ellison has the reputation of being a fun-loving playboy. He's been divorced three times, has two kids, and recently married a fourth time to romance novelist Melanie Kraft.
Ellison admits that personal relationships were never his highest priority while growing up on Chicago's South Side: "When I was a kid, my sister walked into my room and said, 'Larry, which is more important to you – to be admired or be loved?' And I said, 'Well, for me personally? To be admired.' She looks at me, smiles, 'Wrong,' and walks out. It took me a little while to realize that all of us want to be loved. Being loved is more important than being admired. It's something we have a hard time accepting."
While growing up, Ellison would say he never felt loved by his own dad. He remembers the time when he was 12, and his father surprised him with the news that he was adopted: "It was shocking that I just put it away and thought about it for years, without really confronting all and realizing all of the implications."
But what was perhaps most shocking was that the adoption was all in the family. He discovered that his birth mother had given him up as a baby, and that the woman he'd known as his mother was really his aunt. His adopted father, Louis Ellison, was mainly dismissive and Ellison recalls being told that he'd "never amount to anything."
"It was an alternative greeting as opposed to, 'Hi, how are you?' or, 'How did it go at school today,'" recalls Ellison, laughing. "I think, because I was constantly questioning authority, that he felt that would continuously get me in trouble as it had in school -- as it had in the Boy Scouts, as it had on athletic teams."
Is there any part of him now that says, 'It gave me a drive that I might not have had otherwise?"
"Oh yeah. I had all the disadvantages required for success," says Ellison.
Ellison was a college dropout, working at various jobs in the computer business, when he read a report by IBM's research department that described software that could analyze data.
IBM's management had not acted on the idea.
"I said, 'Oh my God, this is exactly what we need to do. We can beat IBM to market with IBM's own technology,'" recalls Ellison. "Because IBM didn't believe in their own idea."
From that, Oracle was born.
And now, the kid who'd never amount to anything is creating a home unlike any other in America. It's really a Japanese village, with more than a dozen houses surrounding a man-made lake. He calls it "Sanbashi," and it is inspired by the ancient city of Kyoto. It sits on 33 acres in Woodside, Calif.
"Not a single nail on the property," says Ellison, who brought craftsmen over from Japan to do the work. "It's all assembled in the traditional Japanese way."
Construction started 10 years ago and has cost over $100 million. The lake was made earthquake-proof by pouring three separate layers of concrete. Thousands of rocks on the property were each handpicked by a Japanese artist.
"The garden is really a piece of sculpture. And the rocks are supposed to look like they were placed here by the hand of God over the last million years," says Ellison.
Japanese culture fascinates Ellison, who owns a priceless collection of 16th century Samurai armor -- fitting for a businessman whose favorite saying comes from the warrior Genghis Khan: "It's not sufficient I succeed. Everyone else must fail."
"That quote I actually got when I was working in Japan," adds Ellison. "And a Japanese executive was describing a competition in Japan and how they take competition in Japan and the pursuit of market share. And this guy said, 'Anything less than a 100, you know, a 100 percent market share was not enough. Every time we lose a deal, we feel that rice is being taken out of the mouths of our children.'"
That killer philosophy, however, can make him a tough man to work for.
Ray Lane was second-in-command at Oracle for eight years and was pushed out by Ellison when they clashed over the direction of the company.
"I knew I couldn't change the culture at Oracle as long as the inventor was still there," says Lane. "Culture is win at any cost. It wasn't good enough for a salesman to make their quota. They had to make 200 percent of their quota. It was the top 10 percent get rewarded millions. And everybody else, you know, falls by the way – they're weak soldiers. Shoot 'em."
Ellison has also been accused of gunning down the competition. Right now, he's in the midst of a hostile takeover of a smaller rival, Peoplesoft, which will potentially put thousands of people out of work. And he's doing this all to make Oracle the No. 1 software company in the world.
"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. I think we are curious about ourselves," says Ellison.
"We're curious about our own limits and we try to discover our own limits. And a lot of what keeps me going and keeps my drive is I'm curious as to how far I can go, how far Oracle can go. They're inextricably linked."
But does Ellison sometimes go too far? For instance, he flies his own planes, and sometimes, as the story goes, without good judgment. There is a story that he once flew a plane under the Golden Gate Bridge – but Ellison wouldn't acknowledge if he actually did it.
"That would be against aviation rules," he said. "So, of course not."
However, he admitted that – if he had done it – he would have taken one of his fighter planes out for the ride.
Whether the story is true or not, what is true is that Ellison sees it all as a game. In that exhibition race that 60 Minutes II went along for in San Francisco Bay, Ellison made it first across the start line.
Nearly 10 miles later, he finished first against the current America's Cup champion -- just one satisfying moment for a man whose life is a never-ending race.