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This is a segment from The Breakdown newsletter. To read more editions, subscribe “Winning. That’s my idea of fun.” ― Larry Ellison Larry Ellison will never be featured in a habits-of-billionaires listicle. In the 2000s, while running one of the most important companies in the world, he typically strolled into the office at 1:30 in the afternoon. When he did arrive, he wasn’t always fully engaged. “He had a reputation for being easily bored by the process of running a business,” according to his biographer. He was often absent for long stretches, “leaving the shop to senior colleagues.” On earnings calls, Wall Street analysts asked how much time he’d spend on boats in the coming quarter. In short, he was the antithesis of the young tech founders profiled in The Wall Street Journal this morning — so devoted to work they barely take time to eat, let alone pursue an outside interest or go on a date. Ellison, by contrast, devoted years to competitive sailing, learned to pilot airplanes, bought an island, designed Japanese-inspired homes, regularly played tennis with Rafa Nadal and did enough dating to be married five times. All while running one of the world’s most important companies. When his first marriage ended in divorce in 1978, Ellison’s ex-wife thought so little of his prospects as a founder that she sold him her claim to the one-year-old Oracle for $500. (In three subsequent divorces, he again somehow managed to avoid surrendering any part of Oracle.) And yet, Ellison passed Elon Musk to become the world’s richest man this week — for the second time. The first time was in 2000, when he briefly passed Bill Gates near the height of the dotcom bubble. By then, Oracle’s ubiquitous databases had made the company one of the three main characters in…

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Filed under: News - @ September 12, 2025 9:30 pm