When Bill Gates Questioned Lyft CEO Risher’s Move To Jeff Bezos’ ‘Tiny, Little Internet Bo

October 2, 2025

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David Risher, the current CEO of Lyft Inc. (NASDAQ:LYFT), recently shared a bold career move he made in 1996 that earned him a scathing rebuke from Microsoft Corp. (NASDAQ:MSFT) co-founder Bill Gates.

In a recent episode of Fortune’s Leadership Next podcast, Risher recounted a conversation with Gates in 1996. At that time, Risher was a successful employee at Microsoft when he decided to leave for a new startup called Amazon.com Inc. (NASDAQ:AMZN).

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Gates was not shy about expressing his opinion on Risher’s decision. “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 made,” Risher quoted Gates as saying.

Despite Gates’ strong words, Risher was drawn to the opportunity at Amazon. Reflecting on the decision, Risher admitted it wasn’t “entirely rational,” but it marked a significant turning point in his career. Today, he is tasked with scripting a “comeback story” for ride-sharing company, Lyft Inc. (NASDAQ:LYFT).

Lyft CEO Risher, who took over in 2023, is focusing on a customer-first approach to revive the company, which had lost market share and profitability. He works undercover as a driver to understand rider and driver experiences, leading to innovations like the “Price Lock” feature and a 70% earnings guarantee for drivers, boosting driver preference over competitors.

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Risher’s leap to Amazon came at a time when the company was still a startup. His decision was influenced by Bezos’s customer-focused approach, a principle that has been a cornerstone of Amazon’s success. Bezos’s philosophy of obsessing over customers and thinking long-term has helped Amazon grow into a $2.3 trillion company today.

Interestingly, both Gates and Bezos have shown interest in the robotics startup FieldAI. This shared interest suggests that despite their differences, both tech moguls recognize the potential of emerging technologies.

Photo courtesy: Alexandros Michailidis on Shutterstock

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This article When Bill Gates Questioned Lyft CEO Risher’s Move To Jeff Bezos’ ‘Tiny, Little Internet Bookstore’—’Stupidest Decision’ Ever originally appeared on Benzinga.com

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