In the fall of 2007, T.J. Clark sat down with three former colleagues from Hotwire.com to assess business opportunities in the travel industry. One jumped out at him. “Those last few miles of the trip were way behind the times,” he says. “We couldn’t figure out why nobody had modernized the experience in the town-car category.”
Deep into the internet era, town-car and limo services still worked pretty much the same way they had in the age of Donkey Kong. If you were a regular business customer, you probably had a service to go to the airport and back, and you knew the driver like you did your barber or dentist. But establishing a relationship beyond your home base was an ad hoc process. It involved scoring leads from friends or colleagues, dealing with scraps of paper with phone numbers and scrawled first names, then getting a suspicious voice at the other end of your cold call. It felt more like finding a bookie than planning business logistics.