Last week, Larry Ellison, the founder and chairman of the international giant Oracle, turned 74 years old – and remains one of the most interesting figures in tech.

Whether yacht racing or buying whole Hawaiian islands or trash-talking competitors, it’s always a wonder to see what Ellison will do next. At the time of writing, Forbes pegs his net worth at about $60 billion.

Here’s how he went from two-time college dropout all the way to international playboy:

Lawrence Joseph Ellison was born in the Bronx on August 17, 1944, the son of a single mother named Florence Spellman.

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When he was 9 months old, baby Larry came down with pneumonia. His mom sent him to Chicago to live with his aunt and uncle, Lillian and Louis Ellison.

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Louis, his adoptive father, was a Russian immigrant who took the name “Ellison” in tribute to the place in which he entered the US: Ellis Island.

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Ellison went to high school in Chicago’s middle-class South Side before attending the University of Illinois at Urbana-Champaign.

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When his adoptive mother died during his second year at college, Ellison dropped out. He tried college again later at the University of Chicago but dropped out again after only one semester.

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Finally, in 1966, a 22-year-old Ellison moved to Berkeley, California — near the future Silicon Valley, already the place where the burgeoning tech industry was taking off.

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He made the trip from Chicago to California in a flashy turquoise Thunderbird that he thought would make an impression in his new life.

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Ellison bounced around from job to job, including stints at companies like Wells Fargo and the mainframe manufacturer Amdahl. Along the way, he learned his computer and programming skills.

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The turning point came when Ellison came to work for the electronics company Ampex, which had a contract to build a database for the CIA codenamed “Oracle.”

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In 1977, Ellison and partners Bob Miner and Ed Oates founded a new company, Software Development Laboratories. The company started with $2,000 of funding, $1,200 of which came out of Ellison’s own pocket.

Foto: Cofounders of Oracle.sourceOracle

Ellison and company were inspired by IBM computer scientist Edgar F. Codd’s theories for a so-called relational database — a way for computer systems to store and access information. Nowadays, they’re taken for granted, but in the ’70s they were a revolutionary idea.

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The first version of the Oracle database was version 2 — there was no version 1. In 1979, the company renamed itself Relational Software Inc., and in 1982 it formally became Oracle Systems Corp., after its flagship product.

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As one of the key drivers of the growing computer industry, Oracle grew fast. In 1986, Oracle had its initial public offering, reporting revenue of $55 million.

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Still, in 1990, Oracle had to lay off 10% of its workforce, about 400 people, because of what Ellison later described as “an incredible business mistake.” Oracle allowed its salespeople to book future sales in the current quarter, meaning all its numbers were skewed. It resulted in lawsuits and trouble with regulators.

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It didn’t get the decade off to a great start. After adjusting for that huge error, Oracle was said to be close to bankruptcy. At the same time, rivals like Sybase were eating away at Oracle’s market share.

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It took a few years, but by 1992 Ellison and Oracle managed to right the course with some new blood and the popular Oracle7 database.

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Ellison is known for his willingness to trash-talk competitors. For much of the ’90s, he and Oracle were locked in a public-relations battle with the competitor Informix, which went so far as to place a “Dinosaur Crossing” billboard outside Oracle’s Silicon Valley offices at one point.

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But Oracle just kept steamrolling over the competition. And with Ellison as Oracle’s major shareholder, his millions kept rolling in. He started to indulge some expensive hobbies — including yacht racing. That’s Ellison at the helm during a 1995 race.

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Ellison even managed to turn a potential loss into a big win. In 1999, Ellison’s protégé Marc Benioff left Oracle to work on a new startup called Ellison was an early investor, putting $2 million into his friend’s new venture.

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When Benioff found out that Ellison had Oracle working on a direct competitor to Salesforce’s product, he tried to force his mentor to quit the company’s board. Instead, Ellison forced Benioff to fire him — meaning Ellison kept his shares in Salesforce.

Foto: sourceRobert Galbraith/Reuters

Given that Salesforce is now a $40 billion company, Ellison personally profits even when his competitors do well. It has led to a rocky relationship between the two executives that continues to this day, with the two taking shots at each other in the press.

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In fact, Salesforce aside, the dot-com boom of the late ’90s benefited Oracle, too: All of those new dot-com companies needed databases, and Oracle was there to sell them.

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When Steve Jobs returned to Apple as CEO in 1997, he asked Ellison to sit on the board. Ellison stuck around for a while but felt that he couldn’t devote the time.

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With the coffers overflowing, Ellison was able to lead Oracle through a spending spree once the dot-com boom was over and prices were low. In 2004, for example, Oracle snapped up the HR software provider PeopleSoft for $10.3 billion.

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And in 2009, Oracle bought Sun Microsystems, a server company that started at about the same time as Oracle, in 1982. That acquisition gave Oracle lots of key technology, including control over the popular MySQL database.

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Starting in the 2010s, Ellison started to take more of a backseat, handing more responsibilities to trusted lieutenants, like Mark Hurd and Safra Catz …

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… but his spending didn’t slow down. In 2012, he bought the entire Hawaiian island of Lanai for an estimated $300 million.

Foto: sourceFour Seasons Resorts Lana’i

Ellison has been married and divorced four times. Coupled with his extreme wealth, it’s given him a reputation as an international, jet-setting playboy. He’s said to be dating Nikita Kahn, a model and actress.

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In 2014, Ellison officially stepped down as Oracle CEO, handing control over to Hurd and Katz. At that time, Ellison held the title of fifth-richest person in the world.

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In 2016, Ellison scored a personal coup: Back in 1998 he made a $125 million investment in ex-Oracle exec Evan Goldberg’s startup business-management software firm, NetSuite …

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… which ended up working out, when NetSuite CEO Zach Nelson ended up negotiating the sale of the company to Oracle for $9.3 billion, netting Ellison a cool $3.5 billion in cash for this stake. Netsuite investor T. Rowe Price tried to block the deal, citing Ellison’s conflict of interest, but it closed in November 2016.

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Oracle is slowly but surely transitioning its business to the cloud — giving Larry Ellison plenty of opportunities to take potshots at Amazon Web Services, the leading player in the cloud computing market.

Foto: Larry Ellison at Oracle OpenWorld ’16sourceJulie Bort/Business Insider

So while Ellison is technically not in the top spot, he’s still Oracle’s chairman and CTO, working to navigate the company through these choppy waters. And the rest, as they say, is history.

Foto: sourceAP Photo/Bernat Armangue