A version of this article appeared in CNBC’s Inside Wealth newsletter with Robert Frank, a weekly guide to the high-net-worth investor and consumer. Sign up to receive future editions, straight to your inbox.
Larry Ellison built the world’s second-largest fortune by holding on to his Oracle shares over nearly five decades of ups and downs. At the same time, he’s spent billions to fund his philanthropy, vast real estate holdings, sports investments and his son’s fast-growing media empire.
How does he manage to spend so much while selling so little?
A close look at the Oracle chairman’s finances and shareholdings reveals a fortune built on mountains of leverage and risk, allowing him to borrow against his shares and raise cash without giving up shares or control. At a time when many tech CEOs are following their wealth managers’ prudent advice to “take money off the table” and diversify through share sale programs, Ellison represents a triumph of old-school, go-for-broke wealth creation, even at the age of 81.
“Ellison does seem to stand out, not just for his wealth but for the sheer size of his pledged shares,” said Michael Sury, associate professor of practice in finance and managing director for the Center for Analytics and Transformative Technologies at the University of Texas at Austin.
According to SEC filings, Ellison owned 1.16 billion shares of Oracle stock as of July, representing 41% of the company’s total outstanding shares. His individual share ownership is far and away the largest of any of the top 10 tech billionaires. Elon Musk, for instance, owns less than 20% of Tesla, while Mark Zuckerberg owns about 14% of Meta shares and Jeff Bezos’ stake in Amazon is down to about 8% of shares outstanding after selling more than $18 billion worth in the past two years.
Ellison has sold Oracle shares over the years, but mostly to exercise options and pay taxes. According to Smart Insider, Ellison has net a total of $5.1 billion from selling shares – representing a fraction of his stake, now worth over $350 billion. The sales included $900 million of shares he sold in 2001, right before the stock plunged on a disappointing earnings report, which sparked an insider trading lawsuit and eventual settlement.
Oracle has also done its part to turbocharge Ellison’s equity stake. According to Barron’s, Oracle’s share repurchase program has reduced the number of outstanding shares by 36% over the past 15 years. The drop in outstanding shares has boosted Ellison’s stake from 23% of outstanding shares to 41%, even though his number of shares has remained stable.
Still, Ellison has continued to spend record sums on real estate, sports, collectibles and other assets. His personal empire includes dozens of luxury properties, the Indian Wells tennis tournament, the Hawaiian resort island of Lanai, a collection of vintage fighter jets, a 288-foot mega-yacht and the Eau Palm Beach Resort & Spa in Manalapan, Florida, which he bought for $277 million last year. The purchase came after he paid $173 million for the 62,200-square-foot mansion in Manalapan that marked the highest-ever sale price at the time for Florida real estate.
Ellison has also funded a vast array of private companies. He invested in Elon Musk’s purchase of Twitter, now called X, offering Musk “a billion or whatever you recommend,” according to a text exchange that was later made public. Ellison has also invested in several longevity and tech startups, and he co-founded global sailing league SailGP.
More recently, Ellison has emerged as a behind-the-scenes media magnate. He backed Skydance Media, run by his son David, in its purchase of Paramount for $8 billion, a merger that closed last month. Now, the Ellison family is reportedly backing Paramount’s largely cash bid for Warner Bros. Discovery in what could be a more than $70 billion deal. Oracle is also among the companies teaming up to buy TikTok’s U.S. operations, although it’s unclear whether Ellison himself would personally invest.
Ellison has also given hundreds of millions of dollars to philanthropy and made headlines last year as part of an NIL deal for University of Michigan football recruit Bryce Underwood that was reportedly worth $10 million. A signer of The Giving Pledge, Ellison posted on X in July that he will be “concentrating his resources” on the new Ellison Institute of Technology, a partnership with the University of Oxford to find solutions to climate change, disease and world hunger.
To fund all that spending and still maintain his stake in Oracle, Ellison borrows heavily against his Oracle shares. According to the most recent SEC filing, Ellison has pledged 277 million shares of Oracle common stock as collateral “to secure certain…
Read More: Larry Ellison $365 billion fortune breaks every rule of wealth management