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Journalism of Courage
David Risher shocked the tech world when he left a high-level position at Microsoft –– a dominant force generating nearly $8.7 billion in annual revenue –– to join Amazon in 1996, a small online bookstore bringing in just $15.7 million. The move seemed risky, especially for someone considered a rising star in one of the world’s most powerful companies.
“It wasn’t an entirely rational move,” Risher, now Lyft CEO, admitted on Fortune’s Leadership Next podcast. Even Microsoft co-founder Bill Gates, the world’s richest man at the time with an estimated $18 billion net worth, tried to dissuade him. Gates reportedly told 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.”
Risher had strong credentials; he had led the development of Microsoft Access, the company’s first database product, and was seen as a leader on the rise. But his interest was piqued after a reference check call with Jeff Bezos in 1995. Bezos’s sharp questions and direct involvement left a strong impression on Risher.
What ultimately convinced Risher to leap were two things: Bezos’s focus on customer experience and his bold forecast that Amazon would grow into a billion-dollar business by the year 2000, he shared during the podcast.
“The idea that you, personally, can improve the lives of millions of customers if you take the responsibility seriously is very powerful,” Risher shared in a 2015 interview with journalist Danielle Newnham.
At the time, Amazon sold only books but had a clear plan to expand. Risher joined in 1997 as the company’s 37th employee and played a key role in launching new product categories like music, movies, and toys.
Amazon hit $1.6 billion in revenue by 1999, a year ahead of schedule. When Risher left in 2002 to teach at the University of Washington, Amazon had grown to $3.9 billion in annual revenue, according to CNBC Make It.
Now CEO of Lyft and 60 years old, Risher still reflects on the leadership lessons he learned from both 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,” he said.
