Uber’s CEO Seems To Have Ticked Off Everybody, Including Apple

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Uber has been in a lot of trouble lately. Half a million people dumped the company in the wake of its refusal to go along with a token traffic strike. Several high profile executives have left the company, some under a cloud as the company’s sexual harassment scandal has unfolded. And in a new profile in the New York Times, it all seems to come down to one man: Uber’s CEO and controlling force, Travis Kalanick.

It’s been well known that Kalanick has personal flaws for years, to the point where normally fawning tech sites will run scathing profiles for him. The portrait that’s emerged of Kalanick over the years is almost a caricature of the Silicon Valley mogul, with a better grasp of numbers than people and a better grasp of what’s legal than what’s right. But the New York Times piece opens with a juicy anecdote about how Uber nearly got booted off the Apple Store for tracking users who deleted the app, and gets worse from there:

…when Mr. Kalanick arrived at the midafternoon meeting sporting his favorite pair of bright red sneakers and hot-pink socks, Mr. Cook was prepared. “So, I’ve heard you’ve been breaking some of our rules,” Mr. Cook said in his calm, Southern tone. Stop the trickery, Mr. Cook then demanded, or Uber’s app would be kicked out of Apple’s App Store.

For Mr. Kalanick, the moment was fraught with tension. If Uber’s app was yanked from the App Store, it would lose access to millions of iPhone customers — essentially destroying the ride-hailing company’s business. So Mr. Kalanick acceded.

The portrait that emerges of Kalanick is unflattering, to say the least, as the Time explores his past as a file-sharing mogul, his obsession with efficiency above all else, and his tendency to bulldoze anything, or anybody, he views as an obstacle. Among other anecdotes, it’s mentioned Kalanick “reinvested” the tax money withheld from employee paychecks from Red Swoosh, one of his previous ventures, back into the company, which put his employees at risk of legal trouble with the IRS. Along the way, you’ve got unfriendly quotes like this:

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