Inside Oracle founder Larry Ellison’s journey from college dropout to world’s 2nd richest man with a luxury lifestyle

At 80, Ellison remains Oracle’s largest shareholder, holding over 40% of the Texas-based software giant, famous for its enterprise databases and growing footprint in cloud computing. He also has a stake in Tesla; a sailing team; the Indian Wells tennis event; and real estate, including Hawaii’s Lanai island, according to The Straits Times.

The tech founder was worth US$251.2 billion (S$322.5 billion) as of July 15, according to the Bloomberg Billionaires Index, putting him behind only Elon Musk.

Born in New York, Ellison grew up without knowing his father.

At just nine months old, his mother sent him to live with his aunt and uncle, Lillian and Louis Ellison, in Chicago. Louis, his adoptive father, was a Russian immigrant who chose the name "Ellison" to honor Ellis Island, the point of his entry into the U.S., according to U.S. magazine Vanity Fair.

It was not until he was 12 that Ellison discovered he had ben adopted. From a young age, he caused his adoptive parents considerable concern due to his penchant for dismantling electronic devices to understand how they worked. This curiosity later laid the foundation for his passion for technology.

He attended the University of Illinois, where he was named science student of the year, but dropped out in his second year after the death of his adoptive mother.

Oracle's founder and world's second richest man, Larry Ellison (with glasses). Photo from Instagram

He briefly attended the University of Chicago but dropped out again after just one semester. Despite his academic struggles, he had already begun learning computer programming in Chicago and soon moved to California, working odd jobs while immersing himself in the tech world.

"I never took a computer science class in my life," he once told the Smithsonian Institution. "I got a job working as a programmer; I was largely self-taught. I just picked up a book and started programming."

In 1976, while other tech giants like Bill Gates and Steve Jobs were already building their empires, Ellison was struggling financially, deep in debt, Chinese newspaper QQ reported. Despite lacking a degree, he secured a job at a software company, where he met two colleagues, Bob Miner and Ed Oates. The three of them quit their jobs in 1977 to start Oracle, a database management company, with an initial capital of just US$2,000, Chinese newspaper Baidu reported.

While his colleagues focused on programming, they recognized that Oracle needed Ellison’s daring vision to succeed. Ellison’s boldness paid off. Within months he convinced the CIA to become Oracle’s first client, followed by contracts with the U.S. Navy and NASA. Despite the initial version of Oracle’s software being dismissed as "garbage" by some in the tech community, Ellison's conviction won over clients, friends, and colleagues.

In 1980 Ellison’s company had just eight employees and revenues under $1 million. However, the following year IBM adopted Oracle for its mainframe systems, and Oracle’s sales doubled every year for the next seven years, according to Ellison’s biography published in the Academy of Achievement.

What began as a million-dollar company quickly transformed into a billion-dollar powerhouse.

In 1986, Oracle went public, and Ellison began acquiring industry competitors, including PeopleSoft for $10.3 billion, Sun Microsystems for $7.4 billion and BEA Systems for $8.5 billion. By spending over $400 billion on 50 acquisitions, he transformed Oracle into a global leader in database software.

Ellison is widely known for his high-profile, jet-setting playboy lifestyle. While many of his peers in tech, like Gates and Jobs, lived relatively simple lives, Ellison’s lifestyle was the epitome of extravagance. He collects cars and private jets, owns his own America’s Cup sailing team, and boasts an impressive real estate portfolio.

This includes a private golf club in Rancho Mirage, California, a $70 million mansion in Silicon Valley, the former summer home of the Astor family in Newport, Rhode Island, a historic garden villa in Kyoto, Japan, and the entire Hawaiian island of Lanai.

His passion for basketball led him to install courts on at least two of his yachts, according to Business Insider. Ellison is also known for his luxury watch collection and yacht racing. Over the years, he has spent lavishly, prompting his accountant, Philip Simon, to once urge him to "budget and plan," Bloomberg once reported.

Billionaire Larry Ellison (R) and a woman identified as Jolin Zhu, his alleged fifth wife, watch Stanislas Wawrinka of Switzerland play against Dominic Thiem of Austria in their quarter final match during day eleven of the BNP Paribas Open at Indian Wells Tennis Garden on March 16, 2017 in Indian Wells, California. Photo handout via AFP

He has been married six times. His first marriage, to historian Adda Quinn in 1967, lasted seven years. Quinn described their marriage as a "roller coaster." Despite earning just $1,600 a month, Ellison spent lavishly, $1,000 on a bike, dining at upscale restaurants, and even borrowing $3,000 to buy a sailboat. Unable to tolerate his impulsive behavior, she filed for divorce.

His second marriage, to Nancy Wheeler Jenkins, lasted just a year. Jenkins gave up any financial claims to Oracle just before the company took off, a decision she likely regretted as Oracle became a tech giant, according to CEO Today.

His third wife, Barbara Boothe, a receptionist at Oracle, divorced him after three years. His fourth marriage, to romance novelist Melanie Craft, was high-profile. The couple wed in 2003, with Steve Jobs serving as their wedding photographer. They divorced in 2010.

His fifth wife, Nikita Kahn, a Ukrainian model and actress, was 47 years younger than him. They met when Kahn was just 19 years old, and they divorced in 2016, finalizing their divorce in 2020.

As of now, he is reportedly remarried to Keren Zhu, a 33-year-old who moved to the U.S. from China to pursue a degree at the University of Michigan.

From a poor, orphaned child to a data empire tycoon, from a notorious playboy to a wealthy businessman in his 80s, Ellison’s life underscores that success is not a straight path, it is about resilience, overcoming failure and never giving up.