Core Insights - Larry Ellison has maintained a significant stake in Oracle, owning 1.16 billion shares, which is 41% of the company's total outstanding shares, the largest among top tech billionaires [6][4] - Ellison's wealth management strategy involves leveraging his Oracle shares to fund personal investments and philanthropy while retaining control over his holdings [4][14] - Oracle's share repurchase program has contributed to increasing Ellison's ownership percentage from 23% to 41% over the past 15 years, despite his stable number of shares [9] Financial Strategy - Ellison has sold Oracle shares primarily to exercise options and pay taxes, netting $5.1 billion from sales, which is a small fraction of his stake valued over $350 billion [8] - He borrows heavily against his Oracle shares, pledging 277 million shares as collateral for personal loans, valued at over $82 billion [14][15] - Unlike many tech executives, Ellison's approach to borrowing against shares is seen as acceptable due to his wealth and influence, which provides lenders with confidence [16][15] Investments and Philanthropy - Ellison has invested in various sectors, including real estate, sports, and media, with notable purchases like the Eau Palm Beach Resort for $277 million and backing for Skydance Media's acquisition of Paramount for $8 billion [10][12] - He has committed hundreds of millions to philanthropy and is focusing resources on the Ellison Institute of Technology, partnering with the University of Oxford to address global challenges [13] - Ellison's investments also include funding for Elon Musk's Twitter acquisition and several tech startups, showcasing his active role in the tech industry [11] Comparison with Peers - Ellison's strategy contrasts with Oracle CEO Safra Catz, who has sold $2.5 billion in options this year, maintaining a smaller stake in the company [18] - The article highlights differing approaches among tech founders regarding stock management, with many preferring to hold onto their shares to maximize wealth [19] - Wealth advisors note that borrowing against shares can be a form of diversification if used for investments, although it carries risks of over-leverage [20]