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When Bill Gates Questioned Lyft CEO Risher's Move To Jeff Bezos' 'Tiny, Little Internet Bookstore'—'Stupidest Decision' Ever

Author: Namrata Sen | October 02, 2025 04:44am

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.

Gates Questions Risher’s Unconventional Move To Amazon

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).

Check the latest price of LYFT stock here

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.

Risher's Bold Choices Fuel Lyft's Comeback With Customer Focus

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.

On a year-to-date basis, Lyft stock surged 59.85%.

Benzinga's Edge Rankings place Lyft in the 57th percentile for growth and the 90st percentile for momentum, reflecting average performance in both areas. Check the detailed report here

Gates-Bezos Come Together For Robotics

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.

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Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.

Photo courtesy: Alexandros Michailidis on Shutterstock

Posted In: AMZN LYFT MSFT

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