Most fascinating problems with Uber CEO

When Travis Kalanick started Uber in 2009, he was already a millionaire and on his third startup company. He adopted the mantra “growth above all else,” and that has both helped launch Uber into the marquee ride-sharing service and global juggernaut valued at nearly $70 billion, and pushed Kalanick, now 40, to step into legal gray areas and even incur the potentially Uber-killing wrath of Apple, says Mike Isaac in The New York Times, basing his Icarus-like profile of Kalanick on interviews with “more than 50 current and former Uber employees, investors, and others with whom the executive had personal relationships.” The entire article is full of amazing details. Here are six of the most fascinating: 1. Kalanick violated users’ privacy and Apple’s policies, and blocked Apple from finding out In early 2015, Apple CEO Tim Cook called Kalanick into his office to give him an ultimatum: If he didn’t stop breaking Apple’s rules, Cook would kick Uber out of the iPhone App Store, “essentially destroying the ride-hailing company’s business,” Isaac reports. In 2014, Kalanick had ordered Uber to start tagging customers’ iPhones with a unique ID that would let the company identify iPhones even if the user deleted the Uber app and wiped the phone. So Apple wouldn’t find out Uber was violating its terms of service, Kalanick had his engineers “geofence” Apple headquarters, feeding fake Uber code to engineers inside the virtual fence, Isaac reports. “The ruse did not last. Apple engineers outside of Cupertino caught on to Uber’s methods,” and so Kalanick, “sporting his favorite pair of bright red sneakers and hot-pink socks,” faced Cook and agreed to stop fingerprinting iPhones. 2. Kalanick tried to win over Oprah and refused Jay Z’s money As Uber’s fortunes started to rise, Kalanick was initiated into the Los Angeles celebrity scene. “Hollywood stars were eager to buy into Uber, which they had started using to get around,” Isaac reports, with actors like Olivia Munn, Edward Norton, and Sophia Bush taking small stakes. Isaac continues:

Mr. Kalanick and a top lieutenant, Emil Michael, sometimes hung out with Leonardo DiCaprio, who is also an investor, and Jay Z, whose wife, Beyoncé, performed for Uber employees at a poolside party in Las Vegas in 2015. Jay Z once wired money to Mr. Michael in an attempt to invest even more in Uber. Mr. Michael and Mr. Kalanick, giddy at rebuffing a celebrity, wired some of the money back, saying they already had too many interested investors.

At another point, Kalanick tried to persuade Oprah Winfrey to join Uber’s board, Isaac reports, which is something Uber executives believed could happen after Mr. Kalanick met Ms. Winfrey at a party on the Spanish island of Ibiza,” but the idea never came to fruition. 3. Kalanick is technically brilliant but ’emotionally unintelligent’ The spotlight wasn’t a natural fit for Kalanick, Isaac recounts, sharing an anecdote he heard about one night a few years ago when the Uber CEO went to a strip club with a married couple: “Kalanick, who was single, pulled out a laptop to work on a spreadsheet, crunching Uber’s numbers while friends watched the dancers onstage.” At the same time, in 2014, Kalanick told GQ his business success had improved his love life, calling Uber “boob-er.” Kalanick “is described by friends as more at ease with data and numbers (some consider him a math savant) than with people,” Isaac says. “Several described him as ’emotionally unintelligent.'” 4. He once registered to run for governor of California Kalanick has proved adept at trouncing city governments, describing his battle to break into new markets as a political campaign pitting Uber against taxi companies. But he actually considered a run for public office in 2003, registering a website to run for governor of California and picking up registration papers. He never followed through, but his competitive streak can be seen not just in Uber’s aggressive tactics but also in his distinction as onetime runner-up champion in the Nintendo Wii Tennis game. 5. Kalanick apparently considers Uber a competitor of Lyft — and McDonald’s Uber had made a cottage industry of trying to sink competitor Lyft, using sometimes ethically dubious means like buying email data of Lyft customers to get a sense of how the smaller rival was faring in various markets. But Uber has also aggressively tried to poach Lyft drivers, especially as Uber’s driver turnover increased. “According to an internal slide deck on driver income levels viewed by The New York Times, Uber considered Lyft and McDonald’s its main competition for attracting new drivers,” Isaac reports. 6. He once withheld employee taxes from the IRS to stave off bankruptcy Kalanick’s first startup was a Napster-like peer-to-peer file-sharing service, and after that company declared bankruptcy in 2000, he founded Red Swoosh, which facilitated the online transfer of large files. “When the company struggled, Mr. Kalanick and a partner took the tax dollars from employee paychecks — which are supposed to be withheld and sent to the Internal Revenue Service — and reinvested the money into the start-up, even as friends and advisers warned him the action was potentially illegal,” Isaac recounts. Kalanick also moved back into his parent’s house to lower costs and keep his company afloat, then raised money. “The wayward tax dollars eventually went to the IRS,” Isaac said, and Kalanick eventually sold Red Swoosh for about $19 million.