The V.F. Interview

Can Uber Fend Off Its Roiling Drama?

Nick Bilton speaks to Brad Stone, author of The Upstarts.
Image may contain Human Person Car Vehicle Transportation Automobile Tire Wheel Machine Spoke and Alloy Wheel
Travis Kalanick en route to the Sydney Opera House in an Uber, November 2012.By Jack Atley/The New York Times/Redux.

All featured products are independently selected by our editors. However, when you buy something through our retail links, Vanity Fair may earn an affiliate commission.

It has been a pretty rough month for Uber. C.E.O. Travis Kalanick was forced to step down from his seat on President Steven Bannon . . ., oops, I mean President Donald Trump’s, economic advisory council. Then, in a scandal that seems to have gone nuclear, a former female employee said she was sexually harassed and Uber did nothing to fix the problem, which prompted Kalanick to launch an “urgent investigation” with the help of Eric Holder. Each scandal has resulted in a new hashtag denouncing Uber and urging customers to delete the app, including #DeleteUber, #DeleteDeleteUber, and, after the latest brouhaha, a #DeleteDeleteDeleteUber.

In the wake of this roiling controversy, I sat down with Brad Stone, author of the new book The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World, to find out why these start-ups keep finding themselves in trouble, and if Uber’s latest skirmishes will have any implications for the $68 billion dollar company’s investors.

Nick Bilton: First, I guess we should talk about the big, giant, massive, gargantuan, neon-pink elephant in the room: the controversy around Uber this past weekend. A former employee came out and said she was subjected to sexual harassment and that she then experienced a pretty pathetic response from Uber’s H.R department. When I read her story after reading your book, I couldn’t help wondering why Uber always seem to be caught up in some sort of turmoil.

Brad Stone: Yes, controversy has tailgated Uber almost since the beginning. I’d say in many cases that the company and its pugnacious C.E.O., Travis Kalanick, invited it; sassing regulators, criticizing customers who complained about surge pricing, cavalierly talking about driverless cars and the likely impact on human labor. That was the old Uber, and Travis has matured in the way he talks publicly, and now he presents himself more humbly. But some early public perceptions about Uber have endured.

Now, to its current imbroglio. The behavior alleged in Susan Fowler’s blog post is deplorable and pretty mystifying. But a few obvious points: Uber does not have a monopoly on anything, least of all boorish behavior in the workplace. And I’m unprepared to draw broad conclusions about the character of its culture based on anecdotes. For example, it’s unfair to call it a frat-boy culture, because there are women in senior leadership positions there. That said, Uber should be publishing diversity reports like other Silicon Valley companies (Travis has pledged this), and we have to hold the company responsible for improving its numbers.

You may be the first person in history to use the word “humble” and “Uber” in the same sentence. (Bonus points for sticking “Travis” in there!) I get that there is a lot of competition out there, and that with all of the industries these start-ups are disrupting, they must go full bore to have an impact. But do you think Uber (and Airbnb) could have grown as quickly as they have and been a bit nicer? Part of me wishes you’d answer “yes.”

I have a chapter in the book about the companies that were nicer. They didn’t get very far. Even though they preceded Uber and Airbnb, you will not recognize their names: Taxi Magic. Cabulous. Couchsurfing. They tried to work within the framework of the established rules. Living up to its high-minded ideals, Couchsurfing even registered as a nonprofit in the state of New Hampshire. It didn’t get very far. So I do think a bit of ruthlessness and rule-breaking was required in these markets, and of course that had its own severe side-effects, many of which we are still living with.

In your last book, The Everything Store, about the rise of Amazon, you document an astounding moment during your reporting where you actually found Jeff Bezos’s biological father in a small bike shop in Glendale, Arizona, and went so far as to explain who Bezos was to his own father. Did you have any similar “Holy shit!” moments when you were writing about Uber and Airbnb?

There are smaller moments that I hope will surprise and delight even close observers of these companies. The time when Travis tried to get Lyft ruled illegal in California, for example; or when Travis accused Brian Chesky, Airbnb’s co-founder and C.E.O., of plotting to buy Lyft; or early in the history of Airbnb, when Chesky and his co-founders propped up a scammy hotelier and party planner operating thousands of illegal properties in New York City. But as for something on par with tracking down Jeff Bezos’s biological father and telling him that his long-lost son is still alive—that was a pretty unique situation.

There’s another book out now about Airbnb, and from what I’ve read, it could easily have been written by the company’s P.R. department. As someone who has written books about these gargantuan tech companies, how do you separate the fluff from the real story?

I haven’t read the other book about Airbnb, but I hear that it’s solid. I do think in tech journalism we are all challenged to extricate ourselves from the gravitational pull of the official, carefully crafted story. You’re an expert at this yourself; you start by discarding the official version of events and then talking to everyone, particularly the exiled founders and ex-employees, and triangulating the various accounts. Somewhere in the muddle of mythology is the truth.

In your book you mention driverless cars a lot, even citing the technology as one of the reasons Uber and Didi decided to quash their war with each other. You also end the book with a discussion with Kalanick about automation. I personally see driverless cars as an existential threat to Uber, and if someone beats them to it, the company could fall to earth as quickly. Knowing what you know about the future, would you invest in Uber?

I agree with you. Uber has to appear competitive on driverless cars, even if the impact of the technology is a decade away. Investors need to feel confident that Uber can chart its own future. But right now—at least this week—I don’t see how anyone can feel comfortable investing in Uber. There’s too much ambiguity and controversy around its internal culture, the lawsuit by Alphabet, and the furious domestic competition with a rapidly expanding Lyft. Next week everything might change, of course. Or, more shoes could drop and there could be pressure on the board to make changes in Uber’s leadership team. For now, if I’m an investor, I’m watching and waiting.