The Industry

“He Wants to Be a Cool Startup Founder”

Travis Kalanick built Uber in his bro-y, win-at-all-costs image. Mike Isaac chronicles how it all fell apart.

Travis Kalanick in red and blue triangles.
Photo illustration by Slate. Photo by Justin Sullivan/Getty Images.

Uber told investors last month that it had lost $5.2 billion in the second quarter, a record loss for a company that has never been profitable even as its ride-hail app has reshaped how many cities work. As it ballooned into a unicorn while bringing millions of riders and drivers onto its platform, Uber became embroiled in just about every kind of scandal possible in today’s tech industry: privacy invasions, sexual harassment, a toxic bro culture, intellectual property lawsuits, mistreatment of gig workers. In 2017, co-founder Travis Kalanick was finally ousted as CEO.

The new book Super Pumped: The Battle for Uber, by New York Times technology reporter Mike Isaac, chronicles this pileup of scandals in rubbernecking detail. It’s an account of the company’s founding, its rapid rise, and the careening troubles that led to an investor-led putsch against Kalanick. I interviewed Isaac for this week’s episode of Slate’s technology podcast If Then. In our conversation, which has been edited and condensed for clarity, we discussed Uber’s growth-at-all-costs mentality, the perils of founder worship in Silicon Valley, and the precautions Isaac took to report on one of the most paranoid companies in the industry.

Aaron Mak: I wanted to first get into the title, Super Pumped, which is this kind of bro-y term that people in the book keep throwing around. Why did you go with Super Pumped?

Mike Isaac: I needed something to really capture the vibe inside of Uber, at least during the reign of Travis Kalanick. He came up with this list of 14 maxims or rules, similar to how Amazon has like 14 principles for their company, and one of the big ones was the level of “super pumped-ness” that employees at Uber have. Part of how they used to evaluate employees when Travis was CEO was by how super pumped one was and how much zeal they brought to the job. So it’s semi-cheesy, but I really think this is the stereotypical Uber worker under Travis that he was looking for—someone who’s ready to attack the day and attack their job and not be super self-aware when they’re doing it, either.

You write a pretty intimate profile of Travis Kalanick. You even describe his reputation in middle school. Can you talk about how you thought about portraying him in the book?

Uber had a gnarly 2017, and most folks’ introduction to Uber, at least more recently, was just “scandal-ridden, bad company, bad culture, blah, blah, blah.” I think Travis is a compelling figure to me because he has these deep issues—some would say problems—that ended up taking him out in the end, but I think he also is sort of this tragic figure, because a lot of what built Uber into this enormous company is what makes Travis such a compelling CEO. From a very young age, he never accepted anything less than winning whatever he did, whether it was selling hundreds of knives over the summer and being Cutco’s top salesman or beating all of his friends and running up the ranks of Wii Tennis in his off-hours. He’s this sort of a dogged competitor, but also I think it belies this kind of nerdy wish to be cool, and at the end of the day, when he’s pushing his black-car-baller image, making it rain at the club with Beyoncé, I think he just wants to be cool. He wants to be a cool startup founder. I think that drives a lot of how companies position themselves in Silicon Valley today.

It seems like you almost have some measure of sympathy for him. Do you think he largely deserved or lived up to this kind of bullying, man-child reputation?

At the end of the day, he was not able to scale back the assets that turned into liabilities, and a more mature founder or someone who was able to better grow with the company that they were behind or that they had created maybe would still be there. Maybe he would still be there if he was able to change in time, but I think 10 years is a long time for any sort of startup with that much capital in it to be a private company. So 10 years of just baggage ended up catching up with him by 2017 and getting him pushed out of the company. I do think it was important to me to make him less of a caricature than he turned out to be just in initial coverage, just because he’s a person and there are a lot of different things going on in there. But in the end he wasn’t able to change, in time at least.

What struck me was just how lonely this guy seemed to be. His girlfriend and his parents were his main social life outside of work. I guess, at that point, that’s what you have to kind of live with. You write a lot about the idea of the cult of the founder. What do you think Silicon Valley learned about founders from Kalanick?

I think there’s two ways to go with this. On the one hand, we’re in this 2019 era of the techlash, right? Where, post–Trump’s election, the fall of Facebook—at least in Zuckerberg and Sandberg’s less glamorous image in the public eye—folks are starting to wonder if maybe founder worship and praising the genius of a twentysomething is not the way to go anymore. Maybe we should be more conscious in how we build these companies. Maybe startups should really try to have more foresight and build more ethical guidelines into their DNA from the outset, and that’s a potentially hopeful version of maybe post-2019 Silicon Valley. On the other hand, Travis is a billionaire five times over. Anyone who got into Uber at an early point is doing very well financially, and there’s a case to be made that maybe no one really learned a whole lot, and we’ll see what companies look like going after.

Travis had this kind of growth-at-all-costs approach to running Uber, and it made the company really successful, but at what point do you think it started actively hurting the company?

There are a number of parts in the book about them going into different countries. I think they did a really good job early on in the United States parachuting into places and setting up on the ground and just getting Uber out as fast as possible. Their whole thesis was: Once someone tries Uber a handful of times, they become a customer for life, and that ended up bearing out in the data because Uber became an indispensable product for people who really connected with it. But I think the other part of that, and this is really an indictment of technology at large, is when you parachute into different parts of the world in which you have no cultural or social context for what you’re doing, you can really kick up some disturbing things, right?

In 2016, I believe it was, Uber was really growing fast in South America, especially Brazil. They were in one of the worst economic climates in the country’s history. Unemployment was skyrocketing. They introduced Uber where these drivers were taking cash as payments, and they essentially became sort of like rolling ATMs to be robbed by burglars in the area. This growth of the service in Brazil without proper checks on identities of riders ended up resulting in the deaths of more than a dozen people in the country, and it was really a brutal and violent time for Uber, growing in places where they didn’t know how they would even operate or what the effect would be. But they sort of pushed headlong and tried to keep pushing through it.

Another country you write a lot about is China. Kalanick had this obsession with breaking into the Chinese market, but even the biggest companies, like Facebook and Google, have failed there. Why did Uber think they could succeed where others hadn’t?

I think Travis in particular relies on his charm. He’s a very charming guy in person. He’s got this boyish thing going on and puppy-dog eyes and grin and whatever. He has a charisma that I don’t think Mark Zuckerberg or Larry Page or even maybe Jeff Bezos has in real life. Maybe a little bit closer to Steve Jobs in that regard, that he can charm people in real life. And I think he really believed that he would be able to get close to the Chinese government. He did a lot of his face time with [Chinese President] Xi Jinping and other officials in the party, and Uber’s not a content company that needs to have censorship over it, right? It doesn’t face the same challenges that Twitter or Facebook does, where the party is worried that Western democratic ideals are going to infiltrate the discourse over there and they’d need to censor it. So his whole point was, “Look, I don’t want to be a Facebook or a Twitter. I just want to provide rides in the country.”

So he thought that would work, but ultimately, it did not. The Chinese like to back Chinese companies, and Didi won out over Uber in that case.

You write that Uber was one of the most “masculine” companies in Silicon Valley. I’m curious what exactly you mean by this and if you think this was to its benefit or detriment.

Besides the literal version where there are just a lot of men, I think dominance and being alpha inside of the company tended to win. Folks would take this kill-or-be-killed mentality to internal competition in how they would protect their areas or grow their regions or tick up their numbers. If they weren’t making their numbers, then managers would be screaming and yelling at underlings, so it was definitely one in which this barbaric urge to conquer seemed to thrive more often than not.

Why do you think they never really managed to completely demolish Lyft? Was it because of the #DeleteUber hashtag?

This is a funny thing I don’t think people really realize. Lyft was actually at death’s door toward the end of 2016 and the beginning of 2017. They were having problems raising further funding, they were running out of money, ridership was just going downhill, and they were closer than ever to closing up shop. And then 2017 happened and Uber got the wind knocked out of it by scandal after scandal, whether it was harassment or this really bro-ish, toxic culture, or this one random guy on Twitter starting a hashtag, #DeleteUber—that ended up spreading to more than a half a million account deletions on the service.

It really gave Lyft the second wind that it needed in order to go and raise money and ultimately become a public company. And it’s really crazy to think of what a world without Lyft now would have been. It would have just been Uber conquering the U.S. market.

I wanted to move on to Susan Fowler’s whistleblowing on sexual harassment. You write that “of all the scandals Uber had suffered to date, the Fowler memo struck the company the hardest.” Compared with everything that was going on, why was this scandal so impactful?

At the point that she writes the memo, she’s an ex-employee, she’s out of the company, but it really sort of put into words all the problems that women inside of the company had had with the culture to date. There weren’t official HR processes, it was a huge company, there were more than 10,000 employees, and yet some basic big-company things weren’t in effect. You couldn’t really take complaints about harassment or other things to managers, and people who felt marginalized inside the company, it really resonated with them. Companies have to deal with external crises often, but when you’re really in trouble is when your own people are starting to revolt. That was the turning point when things got bad inside and folks were starting to leave more frequently.

So leaking was a big indicator, it seems like. Were there any other indicators that this seemed like a turning point internally?

Yeah, I think attrition was a huge problem too. One thing I read about was the cocktail-party test. You want to be able to go to a cocktail party in Silicon Valley and be proud of the company you work for or be able to wear a T-shirt that says “I work for Uber,” and that started becoming a point of shame, not a point of pride for a lot of people. I talked to recruiters who were just going gangbusters trying to pick people off from Uber as they were bleeding talent like crazy. So it’s definitely this internal morale thing, and then people jumping ship who were folks at the top. And then numbers going down. For a long time, they would say, “Look, we have all these problems, but people still love our service and the business.” But after #DeleteUber, that was actually … the numbers started going in the opposite direction, and that was way bad.

Another big scandal you write about in the book was Greyball, the program that Uber used to basically hide from authorities. To the extent that you can, can you talk a bit about how you broke that story?

You know, in reporting, stories just lead to other stories, right? Once you write one thing, then it might resonate with some folks. So I wrote something on Uber’s culture that was a pretty rough story for them, and someone who was reading it, who was connected to the company, had told me that they read it and said, “Hey, I want to meet you and I want to talk about this program that Uber had at one point.” So we met—I detail that in the book, the process of that, and then the lengths we had to go to stay quiet and private. Greyball was essentially a program that some thought was obstruction of justice, and it was a way for Uber to move into cities, hide their app from transportation officials or law enforcement officials, and evade capture or the impounding of their vehicles while keeping the service up and running for normal customers to use. It was very smart and ethically questionable.

I don’t want to give it all away, but you write about how the leaker basically had to meet you at this really dingy pizza place. Is that how leaks usually work at Uber? Are you meeting people at these really covert locations?

I think it’s all over the place. I think one thing that I feel has helped me, weirdly enough, is just putting myself out there a lot. Reporters get scoops as we write about the companies themselves, right? So the fact that I was writing about Uber for a few years probably helped me, but also I like to keep a running dialogue on Twitter—the hell site of choice for a lot of journalists—and kind of just talk through what I’m thinking about at any given moment. And folks have reached out to me through there. There have been all sorts of people coming through intermediaries. It’s very different every time, but it’s probably not smart to go to the Battery, which is a swanky, upscale San Francisco club for techies, if you’re trying to meet a private source. You want to go somewhere you’re not going to find a lot of tech people, and usually that’s a crappy pizza parlor.

The way you describe it made me deeply paranoid—I want to delete my Uber app now. So as a reporter covering Uber, were you ever worried that the company was just really aggressively surveilling you?

A number of my sources told me, “OK, do two things. One, you need to delete all your contacts from Uber’s servers.” Because there’s a feature they use, in which you can split rides with people or share your location with people, that requires your contact list. So they wanted me to delete that from their servers and then just delete the app from my phone entirely and never use it. Also, “always take public transportation to meet someone.” Look, these companies create the most sophisticated tracking devices and ways of measuring how their users move and interact with the world, so if you already have a company that’s built this amazing surveillance apparatus, it’s best to go to great lengths to try to avoid it, especially when you’re meeting people and talking about sensitive things.

Something else that struck me about the book was the way you talk about the press. There’s this motif of Uber executives saying stupid things to the press. What about the company do you think made them so prone to these unforced errors?

I don’t know. Maybe Travis or Emil [Michael] felt more comfortable with the press than they should have early on. Maybe they were used to an era of press coverage … I mean, I make a distinction of coverage of tech companies in the early days versus more recent days, and now it’s a more oppositional relationship, I would argue. But earlier on, it was just definitely this image of whiz-kid founders in hoodies making millions of dollars, so maybe they made the mistake of thinking that the press was on their side or going to write nice things about them. And some people did. Some people covered them very well. I just remember when most of the story for me was about writing how much money that they raised, and that was a really fascinating part of it just because they kept raising obscene amounts of money. They weren’t as careful as they should have been, I guess, or at least they let the veil slip more than they needed to. It’s weird because every time they tried to do a profile—usually if you give an access profile to some journalist, it might be a nice fawning piece—they never got a nice fawning piece out of it. They couldn’t help themselves, I guess.

Throughout the book, they’re just getting so much bad press, and you’re someone who’s broken a lot of big stories about Uber—I’m thinking the X to the X Party [Uber’s 2015 celebration in Las Vegas] in particular. Do you ever think about how you’ve shaped the public’s perceptions of the company?

Yeah, totally. That’s a good question. I’m obsessed with trying to be fair about this. Have I been really hard on the company? Yes, absolutely. Have I done pieces that I think have shaped the public’s perception negatively? Probably, but I think it’s also I’m just putting out there what they haven’t wanted people to know about. The press officer specifically told all of the company to not advertise that they were at Uber for this huge party, this $25 million party that they threw in celebration in 2015, right? So my thing is, look, I’ll put out the good and the bad, but you’re going to be judged on your own merits, and if you’re comfortable with how you act at the end of the day, then that shouldn’t be a problem.

Zooming out, Travis always had this vision to eventually compete with Amazon side by side. Do you think that Uber could still get to that point, where they’re massive and battling Amazon, or are the dynamics just too out of their favor?

I do wonder what Uber’s future will look like. It’s still pushing really hard this idea that it’s a transportation platform, so they’re going to be moving around people, or things, or your burritos, or whatever, right? The future is theirs, whether it’s by car or by scooter or by hot lunch plate. I don’t count them out. Look, I think they’re making investments in important areas. I think it’s going to cost a lot of money to get to where they want to be. To go with that analogy, Amazon lost money for a number of years too, to get to the dominant place that they are right now. It’s just really difficult because Uber has a lot of well-financed competitors in regions across the world, whereas Amazon I don’t think had as much intense competition as they did compared to Uber today. If Uber can execute and maybe pull the right levers, and maybe they have to concede some defeats but win in other areas, then perhaps it’s not crazy to think they could be at least some form of Amazon for transportation.

Do you think [current CEO] Dara Khosrowshahi could be the person that takes them there? Does he have the hustle, for lack of a better word?

Hustle, hustle, hustle. That’s funny. No, you’re right. Hustle is what defined Uber. I think it’s still TBD. I think he’s absolutely been this calming force in the ranks that Uber probably needed in 2017 after the building was on fire for months on end, and I think folks are happy internally that they’re not getting just gnarly negative headlines every other week under Travis. I think there’s still a question mark as to whether he can push folks the same way that Travis did. That’s one thing that people really do appreciate Travis for: his early role in the company and for building it into what it is, so that’s still a question mark. I don’t know. I think it’s been two years since Dara took over, and probably we should give him at least another year or so to check back in on his report card.

Listen to this week’s If Then episode via Apple Podcasts, or the player below: