Larry Ellison: How His Wealth Strategy Goes Against Traditional Strategies

Larry Ellison, co-founder and chairman of Oracle, has amassed around $365 billion—a feat that, by conventional wealth-management standards, defies almost every rule. While most financial advisors preach diversification, liquidity, and minimizing risk, Ellison has leaned hard into concentration, leverage, and what many would consider bold risk exposure. That approach has yielded astonishing gains, but also carries its own set of dangers.

One of the most striking departures from standard advice is Ellison’s enormous stock concentration in Oracle. He owns roughly 41% of Oracle’s outstanding shares, according to recent filings. Rather than selling significant chunks to diversify or lock in gains, Ellison tends to hold on, letting Oracle’s long-term performance amplify his wealth. This is almost the reverse of what most wealth managers recommend: lightly trimming or hedging concentrated positions to reduce exposure to company-specific risk.

Instead of selling, Ellison often uses his Oracle stock as collateral. He borrows against those shares, sometimes leveraging them heavily, to fund large personal purchases, investments, real estate, or acquisitions, without relinquishing ownership of the shares. That lets him maintain control and benefit from any upside in Oracle’s value while still accessing liquidity. However, this borrowing-against-stock strategy introduces risks not typically found in conventional portfolios: if the stock falls sharply, forced margin calls or collateral losses could cascade.

Ellison has also benefited massively from Oracle’s aggressive stock buyback programs. By reducing the number of outstanding shares, the buybacks increase the value of each remaining share, thereby magnifying the wealth of those holding a large stake. Oracle has significantly reduced its outstanding shares over the past decade, making Ellison’s ownership percentage more commanding, even if his actual number of shares has not increased substantially.

Another rule he bends: the notion that wealth should be made liquid to preserve flexibility. Ellison’s wealth is massively “on paper,” tied up in Oracle stock and other illiquid or semi-liquid assets. While he does hold liquid assets and has sold shares periodically, these sales are relatively small compared to the value of his overall stake. The bulk of his net worth depends on Oracle’s stock price, not dividends or regularly cashed-out gains.

Wealth managers typically caution against relying too heavily on “one-horse” investments. If the single company or sector faces a downturn, profits can reverse dramatically. Indeed, Ellison’s net worth has shown sharp swings—he briefly surpassed Elon Musk’s for the top spot among global billionaires after Oracle’s stock surged, only to see portions of those gains evaporate days later.

Finally, Ellison’s approach also contradicts the typical wealth-management practice of selling shares ahead of tax or estate planning events to reduce liabilities or lock in gains. Ellison appears to allow gains to accumulate and relies more on pledging shares or stock-based mechanisms rather than triggering major tax events. This could be interpreted as a means of preserving capital and leveraging opportunities while deferring tax consequences.

All this isn’t to say Ellison’s path is reckless. He is a founder and visionary in a company that remains relevant, as Oracle has recently gained momentum in cloud infrastructure and AI, securing large contracts and enhancing investor expectations. That has magnified his stake’s value. Additionally, Ellison’s size, influence, and years of experience enable him to obtain leverage, structure deals, and access capital in ways that are unavailable to most people. Boards, lenders, and investors often permit him more latitude precisely because of his track record.

Nevertheless, wisdom rests on averages and risk aversion, with rules meant for those without deep, concentrated control of a high-value asset. Ellison seems to have crossed into a different regime, where rules are bendable, not absolute. For aspiring wealthy individuals, his example is both fascinating and cautionary. His path shows what’s possible when you double down on conviction, but also just how stark the downside risk might be when everything depends on one company and one man’s ability to keep it growing.