(Portrait by Jamie Tanaka)

It was a snowy night in Paris in 2008, when Garrett Camp and his friend Travis Kalanick struggled to get a cab. Most would simply moan about the inconvenience and continue shivering in the cold, but Camp and Kalanick instead started dreaming up ways to fix the problem. It wasn’t idle dreaming; the pair were flush with cash after selling startups and were actively searching for their next idea. A year earlier, baby-faced Camp sold StumbleUpon, a web-curating service he and two fellow grad students at the University of Calgary built from the ground up, to eBay for US$75 million. Kalanick, meanwhile, had just sold his second startup, Red Swoosh, a content-delivery company, for $20 million to Akamai Technologies.