Kalanick knew he had made some unforced errors. In the midst of the GQ profile, he let it slip that his newfound tech celebrity, and the attendant riches, made attracting women much easier now than it was when, say, he was living with his parents while building Red Swoosh. On-demand woman, he joked, wasn’t that far off.
“We call that boob-er,” Kalanick told the reporter.
Suddenly, Kalanick wasn’t just a grown man-child in readers’ eyes, he was a blatant misogynist. One particularly cringe-worthy paragraph in the GQ story had Kalanick quoting the infamous Charlie Sheen, describing Uber’s potential success as “hashtag winning.” He name-dropped boutique hotels in Miami like the Shore Club and SLS as places he’d rather be than hustling at Uber. He was trying to be honest—and perhaps a little bit cool—but to the public he sounded like an enormous douchebag.
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