Before David Risher was tasked with scripting a “comeback story” for ride-sharing company Lyft, he made a career move so audacious that it prompted a direct, and blunt, intervention from Microsoft co-founder Bill Gates. In a recent appearance on Fortune‘s Leadership Next podcast, Risher shared the moment Gates told him he was making “the stupidest decision I’ve ever heard anyone made.”
The year was 1996, and Risher was enjoying a successful career at Microsoft during the heyday of Windows. In fact, Risher noted he and his wife just had their 30th wedding anniversary, having met “on the first day” at Microsoft. He said it was a very formative time for him and his career at a very competitive company.
But he had been in talks with a man named Jeff Bezos, who was running a brand-new startup called Amazon. When Risher decided to leave the tech giant to join the fledgling online retailer, Gates himself sent an email and called him into his office.
“He says, ‘Hold on for a second. 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 recalled.
While Risher admitted the move wasn’t “entirely rational,” he said he was drawn to the opportunity. He had first connected with Bezos a year earlier, when the Amazon founder was conducting a reference check. What ultimately convinced Risher to take the leap was Bezos’s intense focus on the customer. “He was very customer-obsessed,” Risher said, noting Bezos’s logic that on the internet, “everyone is one click away from somebody else, so you have to create a great customer experience.” (In fact, Bezos’s management style stressed to Amazonians that they should approach every day from a “day one” mindset.)
Bezos also laid out a compellingly ambitious vision: to grow the then-$15.6 million business into a billion-dollar company by the year 2000. Risher, an avid reader, was captivated by the chance to build something new at the “crazy intersection of technology and culture.” He joined Amazon as its 37th employee, tasked with helping build the “everything store” by adding music, video, and toy categories. The company hit its billion-dollar target a year early, in 1999. The move paid off so well that a “Thank You” letter from Bezos to Risher, dated February 2002, remains on Amazon’s website to this day.
One of the great comebacks
Now, as CEO of Lyft, Risher is applying that same foundational principle of customer obsession to engineer what he hopes will be “one of the world’s great comeback stories.” He said when he took the job in 2023, the company had “lost its way” a little bit, as it was losing market share, and it wasn’t profitable. (Lyft stock is down roughly 20% over the last five years, but has risen 60% year-to-date.) Risher’s strategy has been to return to the basics: understanding what customers actually want.
To achieve this, he famously works “undercover” as a Lyft driver in Napa Valley and San Francisco to learn firsthand about the rider and driver experience. A conversation with a passenger stressed by variable pricing led directly to the creation of Lyft’s “Price Lock” feature. He insists on viewing drivers as customers, too, which led to a 70% earnings guarantee—ensuring drivers always receive at least 70% of what riders pay, a move that has given Lyft a 19-point advantage in driver preference over competitors.
This obsessive focus on improving the service is part of Risher’s fight against what he calls “enshittification,” borrowing the phrase from Cory Doctorow that was named the “word of the year” by both an Australian dictionary and the American Dialect Society for how it summed up widespread frustration with the tech sector, even with modern life. Risher described it as the gravitational pull that makes services worse over time due to profit and investor pressures. By breaking down problems piece by piece, his team has drastically improved the user experience, cutting the driver cancellation rate from a “super irritating” 15% down to below 5%.
From receiving a stark warning from a tech titan to earning a permanent thank-you from another, Risher’s unconventional career has been defined by taking on ambitious challenges. Now, he’s betting that the same customer-first philosophy that turned a small online bookstore into a global empire can drive Lyft’s next chapter of growth.
For this story, Fortune used generative AI to help with an initial draft. An editor verified the accuracy of the information before publishing.