Feb 28, 2014 · 2 minutes

Great news for Dave Morin! His Vanity Fair profile is no longer the most ill-judged piece of PR ever to appear in a glossy magazine.

In his just-published story on Uber and its CEO Travis Kalanick, GQ writer Mickey Rapkin wonders out loud why some people think Uber is a douchey company.

"[T]here seemed to be something vaguely, well, douchey about the way people talked about Uber... Last summer, the company experimented with helicopter rides on demand to the Hamptons; it was a stunt, but one that seemed to speak volumes about its ambitions."
Yep, that could be it. Or maybe people talk about Uber in a douchey way because, when talking to journalists, the CEO of Uber says things that make him sound like a tremendous, unapologetic douche.

Throughout the interview, perhaps mistaking GQ for Playboy, Kalanack unleashed his inner brogrammer, ranging from sexism to Jersey Shorism, to Charlie Sheen. Here are the highlights...

(Reminder: This is the CEO of a company with $307 million in venture and a reported $213 million a year in revenue and a $3+ billion valuation.)

1) "Boob-er."

Not to make assumptions, but Kalanick probably wasn't the first kid in his class to lose his virginity. But the way he talks now—which is large—he's surely making up for lost time. When I tease him about his skyrocketing desirability, he deflects with a wisecrack about women on demand: “Yeah, we call that Boob-er.”
2) "Somehow liable"
There was also a PR misfire in September when a political organizer claimed (via Twitter and a post on Uber's website) that her Uber driver choked her. Police were at the scene, but no charges were filed. The story might have ended there, except that Kalanick's callous directive about how to handle the fallout—he blamed the media for suggesting Uber was “somehow liable for these incidents that aren't even real in the first place”—was accidentally made public. When asked about it now, he repeats flatly that the incident “just didn't happen” and passes on the chance to walk back his remarks.
3)  "I would much rather be at the Shore Club."
Uber's nearly vertical growth hasn't been seamless. After big victories last fall in D.C., Denver, and Dallas, it's turned its energies toward a bitter war with taxicab owners and county commissioners in Miami, where Uber is currently illegal. Without getting too far into the weeds, it's currently against the law for a black car to be dispatched in under an hour. This surely protects limo drivers, who've invested in medallions. But it's also crazy. Says Kalanick: “I'm spending a lot of time with city officials in Miami when I would much rather be at the Shore Club. Or the SLS.” (Those are swanky boutique hotels in South Beach, by the way. I had to Google them.)
4) "Hashtag winning"
Still, Kalanick acknowledges that Uber will have to absorb some hits on customer service—for now at least—in order to deliver on its promise of cars in a hurry. He points out that the rating system is meant to keep subpar drivers off the road. And anyway, he's betting—correctly, so far—that customers are willing to accept the risk. “If you can get a Prius for cheaper than a taxi, you just changed 100,000 people's lives in a city. If you can get it reliably? Holy shit.” Kalanick pauses to sum up the experience, then says unabashedly: “That's hashtag winning.”
Hashtag maybe next time bring a PR person with you.

[Image courtesy Silicon Prairie News]