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Travis Kalanick, the fall and spectacular rise of the man behind Uber

The rise and rise of the transport service is sparking social change from Chicago to Chengdu and the man behind it all, Travis Kalanick, is only just getting started, writes Max Chafkin.

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Travis Kalanick. Photo: Sam Tsang

Jordan Kretchmer remembers what Travis Kalanick was like before Uber was Uber. Kretchmer was a 25-year-old college dropout with a lot of ideas, and Kalanick had even more. He was in his early 30s, an engineer who talked like a sales guy, smart as hell and high on life. He wore a cowboy hat and referred to himself as the Wolf, after the cold-blooded, coolly rational fixer played by Harvey Keitel in Pulp Fiction. He was tireless - always on the move, always thirsty.

They met in 2009 at a music festival and bonded at an all-night "jam session" about the future of the internet. That night in Austin, in the American state of Texas, was a sort of satellite version of the round-the-clock ideas salon Kalanick routinely held at his three-bedroom house in San Francisco. These gatherings were full of young people like Kretchmer who had come up through the wreckage of the first dotcom bust, before jobs in tech were thrown around like free T-shirts at a launch party, before venture capitalists regularly talked about start-ups as if they were mythical creatures. They were entrepreneurs who knew about hustle, who saw opportunity even in the muck of a desperate economy and were going to take advantage. This is what drew them to Kalanick, and vice versa.

Kalanick had made enough on his last start-up, peer-to-peer file-sharing service Red Swoosh, to buy a house and do a bit of angel investing. Uber, the transport app he cofounded with Garrett Camp in 2009, was still more or less a toy, a personal limo service for the founders and their friends in San Francisco. When Camp asked Kalanick to run Uber full-time, Kalanick said no. Uber was "supercrazy freakin' small", Kalanick tells me when we meet.

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Jordan Kretchmer
Jordan Kretchmer

"I was not ready to get in the game and give 100 per cent or 150 per cent," he says.

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Back in those days, if Kalanick liked you, he'd invest in your company, and if he thought your idea was big enough, he'd show up at your office one or two days a week and work for free. Kretchmer hadn't mustered enough courage to pitch to Kalanick that night in Austin, but he met Kalanick later that year to share his ideas. The one he was most excited about was called Tweetbios, and it basically gave Twitter users an expanded homepage.

"That's a small-time idea," Kalanick told Kretchmer. "Small-time, man."

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