The Uber executive team’s long, slow meltdown began, by accident, on November 14, 2014, when someone forgot to tell me that a fancy Manhattan gastropub dinner was off the record.
The occasion was a salon for influencers, an attempt to shape perceptions among tony journalists and other New York figures who might not write about Uber but whose views could filter ineffably through the ecosystem. Arianna Huffington was there, as was the actor Ed Norton.
At the dinner, Emil Michael, the right hand of CEO Travis Kalanick, heatedly complained to me about the press. The company, he told me, could hire a team of opposition researchers to fight fire with fire and attack the media — specifically to smear a female journalist who has criticized the company.
I suggested to him that this plan wouldn’t really work because the story would immediately become a story about Uber behaving like maniacs.
"Nobody would know it was us," Michael responded.
"But you just told me!" I replied.
When Uber realized it couldn’t kill the story, I got a statement from Michael saying his words “do not reflect my actual views.” Then a Kalanick tweetstorm called his comments “terrible” and said “we are up to the challenge to show that Uber is and will continue to be a positive member of the community.”
And that was pretty much it. Instead of making any meaningful changes, Uber simply pressed on for years. It found both continued growth and accumulating scandals. Many of its crises, like those remarks to me, were tinged with misogyny, whether sexual harassment of its engineers or pulling a rape victim’s medical files. After one of those engineers, Susan Fowler, stepped forward with a blog post detailing systemic sexual harassment and discrimination — a post that was followed up by a series of devastating stories by the New York Times, Recode, and others — the company invited former attorney general Eric Holder to lead an internal investigation.
Sunday, the Wall Street Journal reported that Michael is set to resign, and Reuters reported Kalanick will take a leave of absence ahead of what’s expected to be a deeply damning Holder report. (Kalanick is also coping with a family tragedy.)
They will leave having built the most valuable private company in the world. But it is a company whose cultural darkness is inseparable from its place as the icon of the tech boom. Uber — and the boom — have been defined both by massive new conveniences and by a corporate culture that is aggressive, paranoid, and dismissive of, in particular, complaints from women; a culture of enemies lists and cavalier approaches to the law.
Indeed, it is hard to think of a figure from the last five years who has been as successful as Kalanick, save one of course — President Donald Trump. Indeed, Trump and Uber represent the pinnacle of this decade’s American success. They are our defining brands, and their core values of reflexive aggression and casual dishonesty are the decade’s defining values, seven years in.
Uber has sought to steer clear of Trump, but their values are so close that the brands are utterly intertwined in the public imagination. When Uber cut surge pricing for protesters (and thus, wages for drivers) heading for US airports, it found itself apologizing. And Kalanick’s decision to attend a meeting with Trump in order to disagree with him helped prompt the #DeleteUber wave. The Uber founder didn’t endorse Trump or support his policies. But it didn’t seem to matter: Uber may not be pro-Trump, but it is Trumpian.
Michael’s initial suggestion of a guerrilla war on the media, too, seems now to be the distilled core of Trumpism. The company denied any actual plans to dig dirt on journalists, but official denials have never really been worth all that much; that same denial included a demonstrably false claim that they hadn’t used Uber’s data to surveil journalists. A few days later, then-BuzzFeed News reporter Johana Bhuiyan broke the news that Uber been in the market for an opposition researcher, and the company insisted that was an entirely different thing, one aimed at industry foes, not reporters.
As Uber took that pounding in the press back in November of 2014, one voice piped up to cheer Kalanick on. It was Chuck Johnson, who wrote, “Uber's Emil Michael is exactly right about making anti-Uber journalists' personal lives fair game.”
(Johnson eventually got thrown off Twitter after complaints about harassment. He now runs a website whose — reportedly accurate — motto is “President Trump reads us. You should too.”)
Sarah Lacy, the PandoDaily editor Michael discussed smearing, saw the situation a bit differently. It was, she wrote in an email Sunday, emblematic of a moment when “bro culture and cult of the founder and the power of these platforms was starting to spiral out of control.” (Translate that into Washingtonese and you’re talking about Trump, more or less.)
Trump continues to lean on a philosophy of attack, and on a media sphere on Fox and online that is untethered from facts and reporting. Uber, for a time, also thrived with a philosophy of constant attack. As recently as last summer, it was reasonable to argue that the corporate success was worth the human cost.
But Kalanick’s fall, though from a great height, suggests that the laws of gravity still apply. Uber’s besieged PR staff have had no better luck than Sean Spicer at spinning away a torrent of bad facts. The reality that has set in there is that whistleblowers can still hold their bosses to account, that diligent and accurate reporting by dozens of journalists can’t be dismissed or attacked away, and that the independent investigation may ultimately find its target.
If that’s true in the most unreal place of the 21st century, the Silicon Valley boardroom, it might be true in the White House too.