Uber’s CEO seen as playing with fire
SAN FRANCISCO — Travis Kalanick, the chief executive of Uber, visited Apple’s headquarters in early 2015 to meet with Tim Cook, who runs the iPhone maker.
For months, Mr. Kalanick had pulled a fast one on Apple by directing his employees to help camouflage the ride-hailing app from Apple’s engineers. The reason? So Apple would not find out that Uber had been secretly identifying and tagging iPhones even after its app had been deleted and the devices erased — a fraud detection maneuver that violated Apple’s privacy guidelines.
But Apple was on to the deception. “So, I’ve heard you’ve been breaking some of our rules,” Mr. Cook said. Stop the trickery, Mr. Cook said, or Uber’s app would be kicked out of Apple’s App Store.
If Uber’s app was yanked from the App Store, it would lose access to millions of iPhone customers — essentially destroying the ridehailing company’s business. So Mr. Kalanick acceded.
Mr. Kalanick has been seen as openly disregarding many rules and norms, backing down only when caught or cornered. He has flouted transportation and safety regulations, bucked against entrenched competitors and capitalized on legal loopholes and gray areas. In the process, Uber has spread to more than 70 countries and gaining a valuation of nearly $70 billion, and its business continues to grow.
But the previously unreported encounter with Mr. Cook showed how Mr. Kalanick was also responsible for risk-taking that pushed Uber beyond the pale.
According to interviews with more than 50 current and former Uber employees, investors and others, 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.
A blindness to boundaries has been viewed as leading Mr. Kalanick to a pattern of repeatedly going too far at Uber, sabotaging competitors and allowing the company to use a secret tool called Greyball to trick some law enforcement agencies.
Uber has been reeling from allegations of a machismo-fueled workplace where managers overstepped verbally, physically and sometimes sexually with employees. Detractors have started a grass-roots campaign with the hashtag #deleteUber. Executives have streamed out. Some Uber investors have openly criticized the company.