The epic 30-year love-hate relationship of billionaire CEOs Larry Ellison and Marc Benioff (ORCL)

Mike Nudelman/Business Insider

Oracle CEO Larry Ellison and Salesforce CEO Marc Benioff’s on and off relationship makes for one of the most interesting storylines in Silicon Valley.

Ellison took Benioff under his wing and turned him into a star executive by the age of 26. But after spending 13 years at Oracle, Benioff launched his own company called Salesforce in 1999, becoming one of Oracle’s biggest rivals in the cloud software space.

The two love to trash talk each other’s company, often getting into public feuds over their businesses. But some argue they’re still good friends, and have great respect for each other.

Ellison is the fifth richest man in the world with a net worth of over $54 billion. Benioff is worth about $3.6 billion.

Here’s a summary of the epic 30-year love-hate relationship between the two business titans:

Benioff started working at Oracle at age 23. He left a strong impression immediately, winning Oracle's Rookie of the Year award that year.Thomson Reuters

Three years later, Benioff became Oracle's youngest VP at the age of 26. By then, he was already a star executive, making over $300,000 a year.Kenneth Yeung - www.thelettertwo.com

During his 13 years at Oracle, Benioff became one of Ellison’s closest friends and most trusted lieutenant. Carlye Adler writes in Fortune, “They sailed to the Mediterranean on Ellison's yacht, visited Japan during cherry blossom season, spent Thanksgiving together, and even double-dated.”Reuters/Robert Galbraith

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In many ways, Benioff was similar to Ellison: tall, charismatic, technologically savvy, and a gifted speaker. As former Oracle president Ray Lane once said, "Marc would get people believing in his vision and supporting whatever project he wanted to do…That’s Larry…Marc’s one of Larry’s favorite children.”Michael Bradley/Getty Images)

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In fact, the two were so close that there were all kinds of rumors about their relationship. "It's weird…People said I was related to Larry Ellison...that I was his nephew, or that Larry was my babysitter, or he mowed my parents' lawn,” Benioff told Fortune. NetSuite’s Zach Nelson said, “We heard that [Benioff] washed Larry’s car as a child.”Ezra Shaw/Getty Images

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