HomeNewsTrendsCEO reveals how Jeff Bezos convinced him to quit Microsoft for 'tiny' Amazon in the 90s

CEO reveals how Jeff Bezos convinced him to quit Microsoft for 'tiny' Amazon in the 90s

David Risher, now CEO of Lyft, recalled that Bill Gates had the tried to talk him out of quitting Microsoft for Amazon. Gates reportedly called it the 'stupidest decision' he ever saw anybody make.

October 05, 2025 / 09:22 IST
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Lyft CEO David Risher, now 60, says he still draws leadership lessons from Bill Gates and Jeff Bezos. (Image credit: LinkedIn)
Lyft CEO David Risher, now 60, says he still draws leadership lessons from Bill Gates and Jeff Bezos. (Image credit: LinkedIn)

In 1996, David Risher quit his management role at Microsoft—then one of the world’s largest tech companies with annual revenue of nearly $8.7 billion—to join Amazon, a fledgling online bookstore with just $15.7 million in revenue, CNBC Make It reported.

Risher, now CEO of Lyft, recalled the moment on Fortune’s Leadership Next podcast and said, “It wasn’t an entirely rational move.” At the time, Bill Gates tried to talk him out of it, reportedly telling Risher: “You’re leaving this company for some tiny, little internet bookstore that nobody’s ever heard of… that has got to be the stupidest decision I’ve ever heard anyone make.”

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Gates, then the world’s richest person with an estimated net worth of $18 billion, had reason to be surprised. Risher had developed Microsoft Access, the company’s first database product, and was considered a rising star.

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