Oracle Corp co-founder Larry Ellison once said a disagreement over buying a sailboat ended his marriage.

From Medical School Dreams To Discontent

In his 2016 commencement speech at the University of Southern California, Ellison reflected on his early years growing up on the South Side of Chicago, where becoming a doctor was seen as the ultimate measure of success.

He said that dream, reinforced by family, teachers and his girlfriend, gradually became his own — even though it never truly fit.

Ellison recalled struggling through pre-med courses and realizing he had little interest in the path laid out for him.

“I was unable to make myself into the person that I thought I should be,” he said, adding that he eventually dropped out of college at age 21 and moved to California.

Finding Purpose — And Conflict — In California

After settling in Berkeley during the 1960s, Ellison immersed himself in environmental causes, working as a river guide and rock-climbing instructor in Yosemite while programming computers part-time to pay the bills.

He described this period as one of personal discovery and relative happiness.

His wife, however, did not share that view. Ellison said she wanted stability — a full-time programming job or a return to college. The tension came to a head when he decided he wanted to buy a sailboat after taking a sailing class.

“My wife said this was the single stupidest idea she had ever heard in her entire life. She accused me of being irresponsible, and she told me I lacked ambition,” Ellison said.

The disagreement led to him being kicked out of their home and ultimately divorced. Ellison called it a “pivotal moment” in his life.

Ellison Spoke About Choosing His Own Dreams

The Oracle co-founder said the divorce forced him to confront a recurring theme: living up to other people’s expectations.

This time, however, he felt no disappointment in himself. “Their dreams and my dreams were different,” he said. “I would never confuse the two of them again.”

He went on to live on the sailboat with his cat and continued exploring different jobs and interests, eventually gravitating toward Silicon Valley startups.

From A Personal Choice To A Tech Giant

Ellison said his original goal was modest — to create a job he loved by founding a small company. That company became Oracle Corp.

“When people start telling you that you’re crazy, you just might be on to the most important innovation in your life. Of course, the other possibility is you’re crazy,” Ellison said.

From Budget Warnings To A $235 Billion Fortune

According to the Bloomberg Billionaire Index, Ellison currently has a net worth of $235 billion, ranking him sixth on the index. His company, Oracle, has a market cap of $524.17 billion.

The software billionaire is known for his extravagant lifestyle.

In a 2002 email, his accountant Philip Simon reportedly advised him to “budget and plan,” warning that his spending was becoming increasingly hard to sustain, reported Forbes, citing a January 2006 San Francisco Chronicle report.

Photo: Jay Hirano/Shutterstock

Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.