In 1996, David Risher told Bill Gates he was quitting his management role at Microsoft, then already one of the world’s largest companies with annual revenue of nearly $8.7 billion, to take a job at a “tiny, little bookstore online,” called Amazon.
“It wasn’t an entirely rational move,” Risher, who is now CEO of Lyft, admitted on an episode of the Fortune Leadership Next podcast that aired on Sept. 30. Risher served as Amazon’s senior vice president of U.S. retail between 1997 and 2002.
In fact, Bill Gates tried to talk Risher out of the move, he said on the podcast, reminding him he’d been “successful” at the larger company, where Risher had developed Microsoft’s first database product, called Access.
Gates — then the world’s wealthiest person, with a net worth estimated by Forbes at $18 billion in September 1996 — was surprised Risher would want to leave Microsoft for an internet startup that reported annual revenue of just $15.7 million in 1996, only two years after Jeff Bezos founded the company.
“‘Things are going well [here]. You mean to tell me 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,'” Risher said Gates told him at the time. A spokesperson for Gates did not immediately respond to CNBC Make It’s request for comment.
While Risher understood the inherent risk of leaving an established tech giant for a much smaller, and unproven, startup, Amazon’s founder had made a convincing case, Risher said.
‘We’ll be a billion-dollar business’ by 2000
Risher actually first met Bezos over the phone a year before joining Amazon, when the founder called him to check a work reference for another new employee Bezos was hiring.
“We had a great conversation and I was really impressed by the questions he asked, and that the CEO of Amazon would take 45 minutes to personally do a background check,” Risher told journalist Danielle Newnham in a 2015 interview.
By 1996, Risher had become so impressed with Bezos and Amazon that he began interviewing for a job at the young startup. There were two things about Bezos that convinced Risher he was making the right decision, he said. The first was Bezos’ obsession with the customer experience.
“The idea that you, personally, can improve the lives of millions of customers if you take the responsibility seriously is very powerful,” he told Newnham.
The other part of Bezos’ pitch that won over Risher was the entrepreneur’s confidence that Amazon could be the next huge tech company.
At the time, Amazon had a “relatively small business” that initially only focused on selling books. But, Bezos had a clear vision that would start with books and eventually expand to more and more product categories until Amazon became the “everything store” it is today.
“‘I think if we do everything right, by the time we’re in the year 2000, we’ll be a billion-dollar business,'” Bezos said, according to Risher.
A ‘very compelling’ opportunity
Risher obviously bought into Bezos’ vision for Amazon. He found the opportunity to be at the forefront of that sort of massive, rapid growth to be “very compelling,” he said.
“I thought to myself: ‘How often do you get to be at a company that’s right at this crazy intersection of technology and culture and all these different things, and build something that could be a billion-dollar company?'” he told Fortune.
Amazon ended up beating Bezos’ prediction by one year, hitting $1.6 billion in annual revenue in 1999. Risher was a huge part of that growth, joining Amazon as the company’s 37th employee overall, he said. Risher’s role involved expanding Amazon into a variety of new product categories, including music, movies and toys.
When Risher left the company to become a business professor at the University of Washington in 2002, Amazon’s annual revenue was $3.9 billion.
Now 60 years old, Risher has led Lyft since 2023 and he still takes leadership inspiration from his former bosses, the billionaires Gates and Bezos, Risher often says. He also fondly remembers the excitement of Amazon’s early years.
“It was really quite a rocket ship, which is always a fun thing to be on,” Risher said. “That building of something that hadn’t been built before at that scale was really very exciting.”
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