Mike Isaac's lengthy look at Uber CEO Travis Kalanick, the result of interviews with more than 50 people who are or have been professionally or personally close to him, isn't entirely without compliment. "Some consider him a math savant," Isaac writes for the New York Times. But the profile is mostly cutting beyond that. Isaac opens with an until-now-unreported 2015 meeting between Kalanick and Apple honcho Tim Cook, in which Kalanick had to answer for an egregious violation of Apple's privacy guidelines: "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." After a scolding from Cook, Kalanick reversed course in order to avoid getting the boot from Apple's App Store.
In Isaac's view, it wasn't an anomaly, but a regular flouting of rules and norms that's becoming characteristic of Uber but traces back to Kalanick—and his earliest days. The California native dropped out of UCLA in 1998 to form a Napster-like start-up; it filed for bankruptcy two years later (allowing it to sidestep a $250 billion copyright infringement lawsuit). Next was data transfer startup Red Swoosh. Isaac reports that Kalanick and a Red Swoosh partner illegally took employee tax withholdings that were supposed to go to the IRS and put the money back into the floundering company (the IRS eventually got its money). Read Isaac's piece in full here; it includes an anecdote about Kalanick refusing some of Jay Z's money, details about the various and aggressive ways Uber has tried to eat away at rival Lyft, and more on how the Apple violation came to be. (Read more Travis Kalanick stories.)