The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World

by Brad Stone

Wolpert set up Cabulous in San Francisco at a startup incubator called Pivotal Labs, hired a developer, and started working on an app for smartphones. He also started cultivating drivers. The city’s largest taxi fleet, Yellow Cab, had a ten-year technology contract with one of the old-school dispatch companies, and another fleet, Luxor, was using Taxi Magic. But two other taxi companies, DeSoto and SF Green Cab, allowed the startup to pitch its drivers directly. Wolpert remembers long hours sitting in the front seats of cabs, learning the trade and coming to love the city’s grizzled taxi drivers, who had waited years for their medallions and were clinging to a reliable stream of income. “There were so many cool guys,” Wolpert says. “Old Harry Chapins, still driving. Just salt of the earth.” Wolpert was conceiving of a service that empowered those yellow-cab drivers. It would make the traditional taxi businesses more efficient and help drivers boost their earnings. This was his fatal mistake.