What Happened When Uber’s CEO Started Driving for Uber

Using the alias “Dave K” and a gray Tesla Model Y that he purchased secondhand, the chief executive made dozens of trips as a ride-share driver in the following months ferrying people around the hills of San Francisco.

While taking a customer to the airport one evening, he had to ignore frantic phone calls from his chief legal officer who was trying to alert him that a hacker had breached Uber’s network. Another trip took him across the Bay Bridge to Oakland—and he swore never to do it again after getting stuck in rush-hour traffic back to the city.

It was the latest experiment in the CEO’s yearslong journey to reinvent driving on Uber. Along the way, he struggled to sign up as a driver, saw firsthand something called tip baiting and was punished by the app for rejecting trips. Surprisingly hard to take was the rudeness of some Uber riders.