In 1996, David Risher told Bill Gates that he had left the executive role at Microsoft, but later took on a job at a “small, small bookstore” called Amazon, one of the world’s largest companies with annual revenues of nearly $8.7 billion.
“It wasn’t a completely reasonable move,” said Risher, now CEO of Lyft, who was confirmed on an episode of the Fortune Leadershing Next podcast, which aired on September 30th. Risher served as Senior Vice President of Amazon between 1997 and 2002 as Senior Vice President of US Retail.
In fact, Bill Gates tried to speak with Risher from the move, he said on the podcast. He recalled that Risher was “success” at the big company that developed Microsoft’s first database product called Access.
Gates, the world’s wealthiest with a net worth estimated at $18 billion by Forbes in September 1996, was surprised that he wanted to leave Richer for an internet startup that reported an annual revenue of just $15.7 million in 1996, just two years after Jeff Bezos founded the company.
“‘Things are going well (here). I’m going to say you’re leaving this company for a small, small internet bookstore that no one has ever heard of…it has to be the stupidest decision I’ve ever heard,” a Gates spokesman didn’t respond to CNBC immediately.
Risher said he understood the inherent risk of leaving the established tech giant for a smaller, unproven startup that created a compelling case.
“We will be a billion dollar business by 2000.”
Risher first met Bezos over the phone a year before he actually joined Amazon. The founder had called him to check for another new employee’s job reference.
“We had a great conversation. I was really impressed by the question he asked. It would take 45 minutes for the Amazon CEO to personally do a background check,” Richer told journalist Daniel Newnham in a 2015 interview.
By 1996, Risher was very impressed with Bezos and Amazon and began interviewing for his job at a young startup. There were two things about Bezos that made Risher the right decision, he said. The first was Bezos’ obsession with the customer experience.
“Personally, the idea that if you take serious responsibility, you can improve the lives of millions of customers is very strong,” he told Newnum.
Another part of Bezos’ pitch that beat Risher was the entrepreneurial confidence that Amazon could become the next huge tech company.
At the time, Amazon had a “relatively small and medium-sized business” and initially focused on book sales. But Bezos had a clear vision to expand into more product categories, starting with a book and eventually until Amazon became the “all store” it is today.
“I think by the time we’re in 2000, if we’re all right, we’re going to be a billion dollar business,” Bezos said.
“Very attractive” opportunity
Risher has been clearly acquired by Bezos’ vision for Amazon. He said he found the opportunity to be on the forefront of such a large and rapid growth “very convincing.”
“I thought to myself: ‘How often can you get there often to go out at this tech and culture, this crazy intersection of all these different things and build something that could become a billion-dollar company?” he told Fortune.
Amazon broke Bezos’ forecasts for a year in 1999, earning $1.6 billion in annual revenue over the course of 1999. Risher was a big part of its growth, joining Amazon as the company’s 37th employee. Risher’s role included expanding Amazon into a variety of new product categories, including music, movies, and toys.
When Risher left the company in 2002 to become a business professor at the University of Washington, Amazon had $3.9 billion in annual revenue.
Currently 60 years old, Risher has been leading Lyft since 2023, and he is led by former boss, billionaire gate, Bezos, often says, Risher. He also fondly remembers the excitement of the early days of Amazon.
“It was really a pretty rocket ship, and this is always fun,” Risher said. “Building something that hadn’t been built previously on that scale was very exciting.”
Do you want to be your own boss? CNBC’s new online course, how to get started: Sign up for first-time founders. From testing ideas to increasing revenue, find step-by-step guidance for starting your first business.
Additionally, we request that you sign up for CNBC to connect with experts and peers in our newsletter, money, and life to get tips and tricks for success in the workplace.

