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

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.”

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.

Bezos’ pitch: Customer obsession and billion-dollar vision

Risher first spoke to Bezos in 1995 during a reference check call. Impressed by Bezos’s direct involvement and sharp questions, Risher began considering a role at Amazon. What convinced him, he said, were two things: Bezos’s obsession with customer experience and his bold prediction that Amazon would become a billion-dollar business by 2000.

“The idea that you, personally, can improve the lives of millions of customers if you take the responsibility seriously is very powerful,” Risher told journalist Danielle Newnham in a 2015 interview.

Amazon, then focused solely on books, had a clear roadmap to expand into other categories. Risher joined in 1997 as the company’s 37th employee and helped launch music, movies, and toys.

Rocket ship growth and lasting influence

Amazon beat Bezos’ forecast by a year, hitting $1.6 billion in revenue in 1999. By the time Risher left in 2002 to teach at the University of Washington, the company had reached $3.9 billion. CNBC Make It reported.

Now 60, Risher still draws leadership lessons from Gates and Bezos. “That building of something that hadn’t been built before at that scale was really very exciting,” he said. “It was really quite a rocket ship.”