How Jeff Bezos Convinced Lyft CEO David Risher To Join The 'Tiny' Amazon In The 90s

David Risher, now CEO of Lyft, made a surprising career move in 1996, leaving his management role at Microsoft, a tech giant with $8.7 billion in annual revenue, to join Amazon, a small online bookstore. In a recent episode of the Fortune Leadership Next podcast, Risher admitted it wasn't a completely rational decision, considering Microsoft's stature and his rising star status.

The CEO shared that his decision was met with scepticism by Bill Gates, who reportedly called it the stupidest decision he'd ever heard and tried to talk him out of it. Gates reminded Risher of his success at Microsoft, where he'd developed the company's first database product, Access. At the time, Gates was the world's wealthiest person, with an estimated net worth of $18 billion, and couldn't understand why Risher would leave for a small internet startup with just $15.7 million in annual revenue.

"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. 

However, Risher was convinced by Jeff Bezos's focus on customer experience and bold vision for Amazon's growth. He joined Amazon in 1997 and played a key role in expanding the company beyond books, as per CNBC.

How David Risher Joined Amazon

David Risher's interest in Amazon was sparked after a 1995 reference check call with Jeff Bezos. Bezos's sharp questions and direct involvement left a strong impression, with Risher impressed that the CEO would take 45 minutes to personally conduct a background check.

By 1996, Risher was convinced to join Amazon, citing Bezos's customer experience obsession as a key factor. He was also drawn to Bezos's bold vision for the company's growth, despite Amazon's relatively small size at the time.

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

Jeff Bezos's confidence in Amazon's potential was a major factor in David Risher's decision to join the company. Bezos envisioned Amazon expanding beyond books to become a massive e-commerce platform, eventually becoming the everything store it is today. Bezos predicted that if they executed everything right, Amazon would be a billion-dollar business by 2000. 

Risher played a key role in Amazon's rapid growth, joining as the 37th employee in 1997. He helped expand the company into new product categories like music, movies, and toys. Amazon's revenue grew from $15.7 million in 1996 to $3.9 billion in 2002, when Risher left to teach at the University of Washington.

Amazon beat Jeff Bezos's prediction, reaching $1.6 billion in revenue in 1999, a year ahead of schedule. Risher, now 60, leads Lyft since 2023 and draws leadership inspiration from Bill Gates and Bezos. He fondly recalls Amazon's early days, describing it as a thrilling experience.

"It was really quite a rocket ship, which is always a fun thing to be on. That building of something that hadn't been built before at that scale was really very exciting," Risher said.