As the company prepares for its I.P.O. moment on the stock exchange, Kalanick wanted to ring the bell. “That current management won’t let him do that has deeply upset him.”
Over the years, journalists have picked a lot of fights with a lot of people in tech. In my experience, they tend to take it on the chin and move on with their jobs. As one communications director at a major tech company told me after I had written a scathing piece about them, “If the story was wrong, we’d ask for a correction, if it’s right, we just have to take our lumps.” But Travis Kalanick, the former C.E.O. of Uber, takes a different approach.
In late February, I was at the Vanity Fair Oscar Party in Los Angeles, in tuxedo and black bow tie, dutifully saying hello to guests, shaking hands, asking what they thought of the show—the usual schmoozing. At around 11 P.M., I was squeezing through a big crowd of people in tuxes and gowns, trying to make it to the bar, when I ran into Kalanick. Now, I’ve known Kalanick—mostly professionally but also socially—for almost a decade, so while I hadn’t seen him in a year or so, I automatically reached out my hand to say hello. What does he do? He looks me in the eye with an are-you-fucking-kidding-me look and says, “I’m not shaking your hand, homey.” And then keeps walking.
At first I was genuinely impressed by Kalanick’s reaction. Good for him, I thought, for not pretending to like me. But when I bumped into an investor who knows Kalanick a few minutes later and told him what had happened, the friend had a different take. “Are you kidding me?” the investor said, “Travis is worth, what, $10, $11 billion, and he’s mad because of some articles you wrote about him a year ago? He needs to grow some thicker skin.” When I messaged an executive at Uber who had worked with Kalanick and recounted the story, the response was similar. “If he feels that way about you, I can’t imagine how he’d react to me,” the executive said. “Also, that’s so Travis to use the word ‘homey.’”
It slowly dawned on me that these people were right. If you’re still mad at a reporter who wrote a few stories about you, how must you feel about all the employees, board members, and investors who ousted you from the company you co-founded? (I imagine Kalanick lying in bed at night like Arya Stark right before she goes to sleep, reciting the names of all the people that have wronged him. In place of the “the Hound, Meryn Trant, Cersei Lannister,” maybe he whispers to himself, “Wayne Ting, Susan Fowler, Matt Cohler, Mike Isaac . . .”)
As Uber prepares to go public on Friday, after a decade of inconceivable growth and internal conflicts, at an estimated $80 billion to $90 billion valuation, potential investors should be asking two important questions: What kinds of grudges is Kalanick still nursing? And what might he do about them? While Uber has never turned a profit (and notes in its S-1, may never be profitable) its current leadership under Dara Khosrowshahi is hoping to move on from the bro culture of its past, and into a new era where Uber is known for driverless cars, and not infighting. The problem is, Kalanick might not want that to happen. He might have been powerless when, as Mike Isaac reported for The New York Times, Khosrowshahi rejected his request to help ring the bell at the Stock Exchange on Friday. But as anyone who has interacted with Kalanick knows, for better and for worse, he doesn’t take no lightly.
“There’s certainly a part of him that wants to be there to take it across the finish line at the I.P.O. He never actually wanted to take Uber public—he was proud to say this both inside and outside the company—but now that the day has actually come, he damn sure wants to be on the balcony, ringing the bell,” Isaac, the author of the forthcoming Super Pumped: The Battle for Uber, told me in an interview. “That current management won’t let him do that has deeply upset him.”
Will Kalanick find a way to take his revenge, despite being relegated to a single seat on Uber’s board? The theory I’ve heard floating around upper management at Uber for a while is that Kalanick might one day stage a coup to try to return to the company. “Steve Jobs did it, Jack Dorsey did it (twice),” the Uber executive told me. “I can absolutely 1,000 percent see Travis do it.”
In late-2016, a forensic psychologist conducted a study of 261 C-suite executives in the United States, and found that 21 percent of those people had clinically significant levels of psychopathic traits. In other words, one in five C.E.O.s in the U.S. could be a psychopath. (Compare that to about one in 100 in the general population.) It’s impossible to tell which C.E.O.s could be that one in five, but one thing that I’ve noticed all C.E.O.s and very successful founders in Silicon Valley have in common is an ability to obsess over the company they created, and a tendency to see the world only from the perspective of their start-up. Kalanick had that problem, and still has it. As Isaac said to me: “I think there’s a part of him that won’t ever be able to let Uber go. He’s still on the board, obviously. But the guy spent all day, every day for eight years working to build Uber into what it has become—for better or worse. It’s hard for me to see him walk away entirely. It’s still his baby.”
Which brings us back to the public offering. On Friday, Uber may be in a different, much more positive place than it was in a couple of years ago when Susan Fowler, a whistleblower at the company, first wrote a blog post detailing the toxic culture there. But the company can’t really escape the damage that has been done, and the damage still to be done. First, there’s the reality that all the turmoil (and soul-searching) that Fowler helped unleash isn’t over at Uber. The company has remade itself, internally and externally, in a number of important ways, but the Kalanick era continues to echo into the future. Amid all the chaos at Uber, the company’s driverless-car research all but came to a screeching stop and is just now getting back up to speed. Uber has always known that it would one day need to replace real drivers with self-driving software, in order to justify its obscene valuation, but the company is still playing catch-up to competitors like Google. Between the time lost to boardroom squabbling, resources squandered chasing unrealistic goals, and more prosaic technological setbacks, Uber appears to be on an unsustainable course.
As I’ve noted before, what made Uber such a valuable company back in 2009, and why every investor in Silicon Valley wanted a piece of it, was that Kalanick and his cohorts figured out a new way to connect drivers and passengers more efficiently (using a smartphone app) than taxi dispatchers (who used telephones) ever had in the history of the taxi industry. The next phase of their plan for world domination—cutting out the human driver—was even more profound. But it also set Uber up for potential failure: if someone beats Kalanick and Khosrowshahi to the punch, and many are already doing just that, then the company ceases to be as important as it is today.
Then there’s Kalanick’s list of people he won’t shake hands with. You don’t take on an entire industry, and win, without that ultra-obsessive personality that Kalanick clearly has. (He used to refer to his competitors as the “enemy.”) And yet, it appears that same personality trait has been tuned to obsessive grudges—and, potentially, score-settling. Kalanick could take his billions and change an entire other industry, or join the ranks of other billionaires and start building spaceships with the goal of starting a new civilization on Mars. But many people think his primary objective, eventually, is to come back and take over Uber in the same way that Jack Dorsey did at Twitter. “I could absolutely see [Travis] wanting to run Uber again, and he’s very, very clever at engineering ways to climb back to power,” Isaac told me. “I wouldn’t put it past him.”