He Moved Fast and Broke Uber

But is the mess at the company all Travis Kalanick’s fault?

Travis Kalanick speaks onstage at TechCrunch Disrupt on Sept. 8, 2014—happier times—in San Francisco.

Steve Jennings/Getty Images for TechCrunch

On Tuesday, Travis Kalanick, the chief executive of Uber, resigned.* To call Kalanick embattled, as so many have, is understating the case: He had been grappling with numerous scandals and controversies before a shareholder revolt eventually forced him out. The move raises questions about Uber’s future, as well as speculation about Kalanick’s own.

To try to understand Kalanick’s rise and fall, and the culture that made Uber’s position simultaneously so envied and precarious, I spoke by phone recently with Adam Lashinsky, executive editor of Fortune, and the author of the new book Wild Ride: Inside Uber’s Quest for World Domination. During the course of our conversation, which has been edited and condensed for clarity, we discussed the importance of self-driving cars to the future of Uber, whether Kalanick, who will remain on Uber’s board, was responsible for the company’s culture, and whether Uber’s problems are unique in Silicon Valley.

Isaac Chotiner: What does Kalanick’s decision mean for Uber, and how much control do you envision him retaining in the company?

Adam Lashinsky: Given everything that’s happened and most specifically, given that they were looking for a chief operating officer, which everybody agrees was a critical hire, him stepping down is going to make certain things a lot easier for the company. Now they’re not looking for a COO; they’re looking for a CEO. Before, if I were interviewing for this job of chief operating officer, I would want to know: What is my real role going to be? Now I think it will be very clear what the CEO’s real role will be. The only thing left to discuss will be the question you raised of “How much control does Kalanick really have?” I think no one can answer that question completely, but his power has been severely diminished in the last week. I think the next person will have considerable leeway to run the company.

How would you define the culture of Uber as different from other tech companies?

I think it’s an extreme example of the break the rules, aggressive, ruthless, doing something new culture that is very prominent in Silicon Valley. It’s like an exaggerated caricature of the Silicon Valley culture.

How much do you think the problems at Uber over the past six months stem from Kalanick and the style he instituted, and how much is the product of Silicon Valley culture more broadly?

You can’t pin everything on him, but he set the tone. He was a very powerful CEO who was involved in all aspects of the company. He defined the culture of the company. I think you can attribute most of the good and the bad of the company to him.

Do you think it was a conscious decision of his to build the culture in that way?

It’s a reflection of who he is and the experiences he had as an entrepreneur. And it’s a reflection of what it was that they were trying to do. They were trying to solve an unusual problem, which was to disrupt an entrenched and problematic industry, namely the taxi industry. Once you started down that road of going up against taxi commissions and taxi companies in multiple cities and the tactics that they use to fight the taxis, I think that defined the culture as much as Travis Kalanick’s entrepreneurial background.

He was involved with two startups in his career before Uber. One was a company called Scour that was an earlier version of Napster and that failed quickly and completely when it was sued by the music industry. The second one was a company called Red Swoosh that tried to use Scour’s technology in a legitimate way and took years to become a modest success. It took so long that there was a point where he was the only employee of the company. These were the sum totals of his experiences. It was hard. It was hard to fundraise. It was hard to get market acceptance and so he established a reputation as a fighter, as a battler and as a stubborn entrepreneur who wouldn’t give up.

What surprised you most about him when you spent time with him for the book?

The public perception of him is largely accurate in the sense that he’s willing to say exactly what’s on his mind. He doesn’t always care if he hurts people’s feelings. He’ll take a strong position on something even if it’s going to be offensive to other people. But you asked me what surprised me. I guess he’s also, for me anyway, quite an enjoyable person to be around. He’s interesting. He’s intelligent. He’s provocative. I found those things to be enjoyable and entertaining in a way that I think in the public’s eye there’s this visceral hatred for him. I personally don’t share that and maybe that says more about me and my ability to like different kinds of people. I don’t know.

His mother was just killed and his father was seriously injured in an accident. How close was he to them?

He was very close with his parents. I didn’t meet his parents, but from my observations he had a loving and respectful relationship with both of them. I’ve heard people tell anecdotes that he was quite sweet and humble around his parents. That doesn’t surprise me. I’ve seen him in quite relaxed situations where he, I don’t know if I would describe him as sweet or humble, but where I would describe him as someone who’s not arrogant and who enjoys talking to people more or less like the rest of us.

Were you shocked when the stories about law-breaking and sexual harassment at the company began popping up?

Well, for the most part they started coming out after I was done with the book and after I was almost done with the revisions. So for example, the Susan Fowler blog post, the blog post that alleged sexual harassment at Uber came out after I was mostly done with my book. I wasn’t surprised because it’s something of an anything goes environment, but I was surprised in the sense that I didn’t personally know of instances of sexual harassment or sexual discrimination at Uber. I interviewed women on the record and off the record at Uber multiple times for my book and the subject didn’t come up. The subject of a brutal work environment, very long hours, extremely demanding, of Travis being unforgiving and even capricious in his decision-making, that all came up. Sexual discrimination did not.

Do you think Kalanick views the issues of the company as him and Uber being picked on, or do you think he is contrite at all about this culture and some of his decisions?

There’s no doubt that up until very recently he believed that he and Uber were being picked on and that they were going to get through this as they had gotten through other cycles of negative publicity in the past. Other than public comments that he’s made recently, I don’t have any insight into whether or not he’s undergone some sort of conversion or whether or not he believes that the company and that he screwed up and that they need to improve.

What do you see as his future and the future of Uber at this point?

I’ll take him first. He’s 40 years old. He’s a bright guy with varied experiences and so there’s any number of paths he could take. I don’t think he’ll take any of them soon, but presumably he’s got a lot of life ahead of him. As you know Americans are … I’m in France talking to you right now. I had this conversation with some Europeans last night. Americans are very, very fond of second acts. In his case it would be a third or a fourth act, but I don’t see why that can’t happen.

I’m going to give you my optimistic version for the company. If they can get the right CEO, that CEO is going to humbly come in and say, “We made a lot of mistakes. That’s not who we are. This is how we’re going to change things. Please give us a chance,” and move forward. I also think there’s a large segment of the customer base who just isn’t interested in all of this. I can’t prove that, but anecdotally that’s what I believe.

That said, the company faces some very serious legal problems right now, in particular, the Waymo case on self-driving cars, the alleged technology theft. That could get quite bad for the company, and it could also get quite bad for Travis Kalanick, so they need to work through that before we can say what the future of the company is.

It seems to me, as an amateur just reading the news, that the Waymo situation—with Uber accused of stealing technology—is the most serious threat to the company. Both because of the legal issues involved and because self-driving cars are so important to the future of the company.

After the need to find a new leader, or let’s say on a parallel track with the need to find a new leader, it’s the most important issue facing the company right now. Uber and others—Google and Tesla and the auto companies—have invested a lot of money in developing technology for self-driving cars because technologists believe that the technology is still good and will eventually become so pervasive that most of us won’t drive cars around anymore. If you’re the company that controls that technology, then you could in theory control the transportation network that runs that technology. So Uber sees a day where it won’t need drivers with cars. It doesn’t want to have to pay somebody else for the technology to make autonomous vehicles happen. That’s why it’s investing a lot of money in its own self-driving car technology. Google’s investing in it. General Motors is investing a lot of money.

Is your sense that culture changes can come from swapping out CEOs? Or is your sense that much deeper things need to be changed in terms of the corporate culture?

Well, when you say swapping out CEOs you make it seem simple.

Oh sorry, that was just a phrase.

Yeah, I know. I’m not criticizing, but I’m driving toward an answer, which is that simply naming a new person will never be sufficient, but these companies can be highly influenced by leadership. It’s not easy, No. 1. No. 2, cultures are deeply ingrained in these companies, but Uber is 7 years old. It’s a baby. And so as deeply ingrained as its culture is now, it’s had a real shock to the system. So I do believe there’s an opportunity for new leadership to have a meaningful impact on the culture of the company. I’m not suggesting it will be easy, but given how young Uber is, I think it’s possible.

*Correction, June 23, 2017: This post originally misstated that Kalanick resigned on Wednesday. (Return.)