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.
“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.
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.
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.
