Larry Ellison, co-founder and chairman of Oracle, plans to sell up to $7.5 billion of Oracle stock, equivalent to fifteen years of cumulative sales compressed into a single transaction. This sale marks a departure from his historical « buy, borrow, die » strategy, which involved holding shares and using them as collateral for personal loans to avoid capital gains taxes. Ellison owns approximately 1.16 billion shares, representing 40 to 41 percent of Oracle, and has already pledged between 277 and 346 million Oracle shares as loan collateral. He has also made personal guarantees supporting media deals totaling over $40 billion, which may explain this need for liquidity. For Oracle shareholders, the primary concern is whether the founder knows something they do not, although Ellison’s historical discipline around sales suggests a controlled execution.
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