Unlike many startup kids in Silicon Valley, Kalanick isn't much of a kid. Since dropping out of UCLA in 1998, the 37-year-old has managed multiple companies with varying success, none of them as valuable, popular, or controversial as Uber. His first startup ended because of legal actions from media companies; he sold his next startup for $15 million, chump change in Silicon Valley. Uber is his great success.
If Kalanick has learned one thing from managing failed companies, he told the Financial Times, it's that great ideas can only get you so far. "In my last company, where I wasn’t making a salary for the first four years, you learn the lesson hard of being too early. Holy cow, you feel it. So then you get really good at timing," he said. Other (now) successful entrepreneurs can empathize: Bonobos founder Andy Dunn recently wrote about the early, lean years of his clothing company, when he was perpetually a month away from insolvency. He was so broke he once found himself stranded on a first date at a cash-only restaurant when his ATM receipt came back with "two of the most dreaded words on the planet: Insufficient Funds."
Having the right timing has worked out very well for Uber, which weaseled its way into our iPhones just as mobile, the sharing economy, and on-demand services all started taking off. Even in the face of resistance from federal and municipal governments and entrenched taxi-driver unions, the company has seen 20% revenue growth per month, according to the Financial Times. Although other car sharing services are popping up, Kalanick says Uber is miles ahead of its major competitor, Lyft. "In the U.S., in many ways, the table is set. We’re 10 times bigger," he said.