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Founders · 2026-08-31 · 49 min · 9,622 words

#431 How Henry Singleton Worked

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Henry Singleton was a remarkable man with an unusual background for a CEO. A world class mathematician who enjoyed playing chess blindfolded, he had programmed MIT's first computer while earning a doctorate in electrical engineering. During World War II he developed technology that allowed Allied ships to avoid radar detection, and in the nineteen fifties, he created a guidance system that is still in use in most military and commercial aircraft. All of that before he founded the conglomerate Teledyne in the early nineteen sixties, And became one of history's greatest CEOs.

Conglomerates were the internet stocks of the nineteen sixties. A large number of them went public. Singleton, however, ran a very unusual conglomerate. Long before it became popular, he aggressively repurchased his stock, eventually buying over ninety percent of Teledyne's shares. That's nuts. He avoided dividends, emphasized cash flow over reported earnings, ran a famously decentralized organization and never split the company's stock.

He was known as the Sphinx for his reluctance to speak with either analysts or journalists. It turned out he was right to ignore the skeptics. The long term returns are We're generally mediocre.

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