The same year, Mr. Kalanick discussed how Uber had boosted his desirability with women in an interview with GQ, calling the company “boob-er.”
And just days after a former employee published a blog post in February detailing sexual harassment at Uber, Mr. Kalanick
attended Vanity Fair’s Academy Awards party in Hollywood, stunning some colleagues with his perceived insensitivity.
According to interviews with more than 50 current and former Uber employees, investors and others with whom the executive had personal relationships, Mr. Kalanick, 40, is driven to the point
that he must win at whatever he puts his mind to and at whatever cost — a trait that has now plunged Uber into its most sustained set of crises since its founding in 2009.
In 2015 when New York’s mayor, Bill de Blasio, tried capping the number of Uber cars, Uber added a “de Blasio”
tab in its app to show lengthy waiting times for rides if legislation against Uber was allowed to go forward.