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Wild Ride Recounts How Uber Exploded (in More Ways Than One)

Photo: Spencer Platt/Getty Images

For most people, Uber exists as one single thing, an app that lets users summon a car to their door in minutes. But behind that is a giant company that — despite its aim to change transportation as we know it — flew by the seat of its pants for most of its early years. In Wild Ride, out later this month, Adam Lashinsky recounts how Travis Kalanick went from reluctant adviser to the CEO of a company worth more than $60 billion, flouting regulations, ignoring public criticism, and charming investors along the way.

What made you want to focus on Uber? Rather than any other Silicon Valley company?
Well, my last book was on Apple. And I wrote that five and a half years ago, and when I did that, I had a conviction it was the most important company, certainly in Silicon Valley, and arguably, in the world. And that wasn’t a terribly controversial assertion. That worked out well for me. I enjoyed that. I got going on this book, actually, something like, four years ago. So Uber was a lot smaller, but it was already this global phenomenon, and I was intrigued by how quickly it became a thing. I sensed it was going to be a big story, and I thought all the elements were in place for a fascinating story. And then when I got going in earnest about a year and a half ago, it obviously had gotten much, much bigger. I had no idea just how complicated and controversial and headline-grabbing it would become, but here we are today.

What I thought was unique about it — I mean, there are a bunch of superlatives associated with it — it is, or was, the world’s most valuable private company, the most valuable start-up. But just the way that it got going, the technological way, I found fascinating — and also, it was a nice continuation from my last book because without the iPhone and without the App Store, there would’ve been no Uber. And their recognition of that is what made the company what it was, or what it would’ve become. And then the second thing being that, you know, once upon a time, a company couldn’t just start in San Francisco and become global in three years. And that’s also completely attributable to the iPhone and the App Store. That infrastructure around the world is what enabled Uber to go global so quickly. It would have been unheard of even 15 years ago.

I guess the big question that I still can’t quite figure out is if Uber’s business is sustainable, given that a lot of money goes into subsidizing car rides and things like that. Yet, they are still able to attract so much investment. I was wondering why that was.
I don’t know the answer either. Their thesis is that in a given market, where they have a large market share and a loyal customer base, they can make money. Period. Full stop. So then the question becomes, can they do that in all their markets, or can they do it in a preponderance of their markets, and can the profit that they make in those markets sustain the investments that they’re making in other things, including self-driving cars, which is hugely expensive? So, I don’t know the answer. I know that that’s what they believe. Interestingly, I think that’s what the new investors in Lyft believe, also. They believe that when the market comes down, in other words — and now we’re just talking about the United States — when both companies stop their subsidy war, they can both make money. I think that’s at least plausible.

It’s interesting that you bring up customer loyalty, if only because this past year has not been a great year for Uber-customer loyalty. In terms of Uber’s PR problems, has the past few months, starting with the #DeleteUber campaign, been particularly bad or just another thing that they ride out?
Again, I think you’re asking the existential question, and right now all we have is anecdotal evidence. We have some evidence that it works, some hundreds of thousands of deletions around the #DeleteUber campaign in late January, after the whole JFK debacle, followed quickly by the Trump council debacle. And certainly, in certain bars and coffeehouses in San Francisco and New York, you would think that Uber was going to go out of business tomorrow. And I don’t mean to minimize that, that negative public perception is real. So then the question becomes, what does the rest of the world think? And I don’t have any data, and if they have data, they’re not releasing it. I have a hunch that there also was a contingent of people, half a step back — there certainly is a contingent of people who have no idea what Uber is, or who only have this vague idea of what Uber is. And we who live in big cities tend to forget that. That’s No. 1. No. 2, I think there’s a contingent of people who aren’t interested in all of this. They’re interested in the cheapest and quickest rides, so, again, I’m not minimizing the public perception they’ve taken. I just think there’s evidence they can overcome if they don’t completely screw it up.

And there’s also been talk about Uber’s corporate culture and how demanding it is. And how problematic it is. I was wondering what you had uncovered over the course of writing this book and what your impression of that was.
Yeah, the corporate culture of Uber comes down to one person and that’s Travis Kalanick. He drives the culture of the company. And you know, in short, everything you hear about him is true. He is the thing that people say about him and so it’s cliché, but I think he’s the company’s biggest asset and its biggest liability. So, the question becomes: Can he grow enough to lead a big, modern, global company? And the jury’s out on that. At the same time, most people believe they wouldn’t have gotten to be where they are without him. So, he’s no fool. What I write in my book is that he’s a complicated guy and he’s not; he’s not completely self-unaware. But he has some eccentricities and some blind spots, and he believes what he believes. The big catch for Uber, and you and I are talking on May 10 — the big catch for Uber, I think, is who they can attract to be this No. 2 to Travis Kalanick. A lot rests on the shoulders of that person and that hire.

I think, in reading about Uber, one of the interesting things about Kalanick is the vocabulary people use to describe him. He’s often referred to as ‘young’ or ‘stubborn’ or ‘misguided’ in some of his actions. Which is interesting because he’s not really inexperienced or young. And I was wondering why people see him that way, or why you might think that he is that sort of person?
Yeah, so it’s an interesting question. True, he is not young. He is 40 years old. The first company [Kalanick helped to start] was this proverbial college-dorm-room start-up that never went anywhere. It was interesting; it had a moment; but it never amounted to anything. The second one basically wasn’t a company for a very long time, and then he was able to pull a rabbit out of the hat and sell it for what Silicon Valley people would call a relatively modest amount of money. And my only point in saying that is, it’s not like he spent seven years at Goldman Sachs or eight years at Procter & Gamble. None of this excuses anything, but I think explains that, No. 1, he’s not young, but he sort of has this 20-something-year-old mind-set. He’s single, and he’s out there on his own, and he’s always hustling and all that. And then in terms of experience, this is his first time doing something this big. Despite his fame and despite the size that Uber has, the previous two companies he was in never did anything close to this. So, I only point that out for the — because you could say, “Well, Zuckerberg didn’t either.” Absolutely right, Zuckerberg never saw anything. So, that’s the contrast between the two of them.

This book is coming out at an interesting time, given the lawsuit between Uber and Waymo. Is there anything you gleaned from writing this book that didn’t make it in, or seems interesting in retrospect?
You know, when I wrote, I had this scene at the end of my book where I take this long walk around San Francisco with Kalanick — and this is one of the ways he unwinds and relaxes, taking these long walks around the Embarcadero and the Waterfront in San Francisco — and he told me on this walk that there’s one person he’d been doing this with regularly, but he couldn’t tell me who. This is before the Otto purchase, the purchase of Anthony Levandowski’s company. Turns out, Anthony Levandowski was the other person he took these long walks with. Depending on where this trial goes, I think Waymo’s lawyers are gonna wanna know what they talked about on these long walks. I certainly didn’t know that was happening.

When you read about what Waymo was alleging Kalanick and Levandowski tried to do, does that read as surprising to you?
When I read Waymo’s allegations of what they did do, if you read my book, this is a guy, and this is a company, that pushes the envelope constantly and has even — people close to him have described him as shifty or sneaky. So, no. After spending a year and a half looking at this company, nothing surprises me.

What was the most surprising thing that you learned in writing it? Even if nothing surprises you.
Toward the very end, Travis Kalanick and I had a bizarre conversation, where he asked me if I think he’s an asshole, and I do what a good journalist would do: I sort of bobbed and weaved and suggested, first of all, it’s not for me to say, and I don’t think that’s a matter of fact. He believes that you can prove these things one way or the other, and I challenged him on that. And then he told me he doesn’t think so, and he’s clearly bothered by this. And I found that surprising and fascinating. You have this image of someone, like him or Steve Jobs or Jeff Bezos, not caring what people think; he does.

I’m curious about your time spent driving as an Uber driver, and what that was like. I think you sort of get right up to it without outright saying that driving for Uber is unsustainable as a full-time job. Is that your take on it?
I don’t want to necessarily say that because I don’t want to be in a position of judging what’s enough for somebody. I’ve talked to enough drivers who appreciate the flexibility for them of the opportunity. That said, it didn’t take me long to find out that I liked my job better than being an Uber driver. And that I didn’t particularly like it as a way of making a living. I thought it would be fun, you know, to drive all over the place and meet people, and I didn’t find it to be that much fun.

What was the sort of typical Uber customer, or did it vary?
Yeah, I usually had two types, like, people in their young 20s going around, or business people coming from the airport or going to the airport. I did not drive on a Saturday night or a Thursday night in downtown San Francisco, which is when a lot of people try to make their money, but it’s also the time that you’re most likely to get drunks in your car, and I didn’t do that.

What sort of obstacles do you see in Uber’s future, aside from lawsuits? Is Lyft still a big problem for them? Is some unseen innovation going to upend them?
Short term, they’ve solved a lot of their regulatory problems in a lot of places, but they’ll continue to have some regulatory issues as time goes on. And, yes, Lyft is a concern in the United States, and Didi is a concern in other places besides China. You know, as you pointed out at the beginning, their own business model is one of their concerns. At some point, they’re going to have to start making money. And then there’s the sort of longer term, and it’s not just a long-term thing, but these further-out challenges; if they don’t learn self-driving cars, something could happen where they just flip the script and they’re not the dominant player anymore. But that’s not something that’s going to happen immediately.

Do you have any insight into how far from viability self-driving cars are for them?
They are considered one of the leaders right now, but there’s a lot of people investing a ton of money and, you know, the saying around self-driving cars right now is that the technology is there, but the consumer acceptance and the regulatory acceptance are complete unknowns. Everyone believes that electric cars are superior to gas combustion-engine cars, but we’ve got decades of capital and investments in the internal combustion engine, and that’s not going away overnight, no matter how good electric cars are, and the same is true for self-driving.

Uber is an interesting company that I have always had a weird relationship with. Because I didn’t want to become reliant on them, in a way that a lot of people seem to have, and I assume those holdouts are going to die out sooner rather than later.
I don’t know. In the U.S., for example, it depends on how well Lyft is funded, or if their business can take hold. Juno put up this fight in New York, and then Gett bought them, and it’s been a time of easy money, so we’ll see over economic cycles. It’s funny, I haven’t heard many people like you say, “Well, most people will probably just give in and start using Uber.” In San Francisco, certainly you often hear people say, “I’ll never, ever, ever take Uber.” We’ll see. It’s a long time.

Wild Ride Recounts How Uber Exploded (in More Ways Than One)