Larry Ellison, the 82-year-old co-founder of Oracle, has shown that even billionaires struggle with liquidity. Oracle disclosed that Ellison planned to sell 50mn shares, valued at over $7bn, between June and October, but the plan was cancelled without explanation.

Ellison's need for cash likely stems from supporting his son David Ellison's media ambitions. He is part of a group funding a $110bn takeover of Warner Bros Discovery and previously helped David buy Paramount for over $20bn. Oracle generates $2bn in annual dividends for him, and nearly a third of his shares are pledged as collateral for personal debt.

However, selling such a large stake is tricky. It can signal bearishness and depress the share price. Elon Musk's Tesla stock sale in 2022 to fund Twitter saw Tesla shares fall by two-thirds that year. Oracle's equity has already halved in the past year amid AI infrastructure concerns and over $150bn in debt.

Ellison's media side quests add risk for Oracle shareholders, as the Paramount-WBD tie-up faces legal challenges and will be highly leveraged. Any missteps could force further share sales.