‘I’ve Never Seen a Cast of Characters That Willing to Kill Each Other’: Mike Isaac on Chaos at Uber

Travis Kalanick Photo: David Paul Morris/Bloomberg via Getty Images

It seems like every large tech company has had a rough couple of years, but it’s easy to argue that no company has had a worse year than Uber did in 2017. It began with the #DeleteUber controversy, then rolled right into a number of scandals regarding sexual harassment and inappropriate workplace conduct. Together they further solidified Uber’s already dicey reputation as a start-up willing to push past boundaries, particularly legal ones, and burn billions of dollars in VC cash as it brute-forced its way to ubiquity.

By mid-2017, Travis Kalanick, the CEO who masterminded Uber’s success and who oversaw the company’s aggressive strategy and corporate culture, was out. He was forced out by a phalanx of investors who saw his continued involvement as an extreme liability to the company. In Super Pumped: The Battle for Uber, New York Times reporter Mike Isaac recounts Uber’s rise and Kalanick’s fall, surrounded by a cast of assholes and opportunists, like famed venture-capital investor Bill Gurley and celebrity ally Arianna Huffington. In one passage, the CEO writhes around on the ground in anguish. It is perhaps the most complete picture of how the bulletproof founder was brought down from inside his own company. Isaac (who is, full disclosure, a friend) took some time to talk about where Uber’s been and where it might be headed.

In the lead-up to this book’s publication, you were very paranoid about information from it leaking out. Now that it’s on shelves, can you say what some of the biggest scoops in it are and describe them in as much detail as possible?
I don’t know if I should tell you every scoop. I think that’s probably bad for an interview. One thing that I am kinda proud of is, I actually got ahold of a document that Travis writes that is trying to essentially save his own ass before he gets ousted from the company. It’s an internal memo, it’s probably like a couple thousand words, and it really underscores the issues that he had as a leader and that he created problematically inside of Uber. It really was the first tacit admission of his faults as CEO. And it was very impressive for me to read it and be like, “Maybe this guy gets it.” But ultimately he was not able to ever send that memo. I don’t think anyone inside has seen it because he was ousted by his board and investors before he was able to send it.

I get into detail about a few incidents in Southeast Asia that underscore the depravity in at least some of the offices in this company. Like managers smashing a girl’s face into a pile of cocaine. In another incident, this other woman feared getting raped and her manager texted her, “Don’t worry, we will pay all your medical bills.” I go through story after story of disturbing things, but I think the point of it for me was to show that company culture is important from the very beginning and things can get gnarly and out of hand if you don’t pay attention to that. And it multiplied in dozens of cities around the world.

Did you talk to Travis Kalanick for this book?
I can’t really get into who I did and didn’t talk to, but I will say Travis did not cooperate for the book and has not commented or anything. So I’m curious to see what he thinks about it.

The book often flips back and forth between talking about Uber as this great, revolutionary product, and then also Uber as this really rotten company. Do you think that the end result justifies the sorts of tactics Kalanick and his company used?
I get asked a lot about whether this company could have been what it is without Travis at the head, or without the tactics that they deployed in order to get there. I think you can be aggressive in business without being a dick. And there are probably many examples of respectable folks that take audacious moves without this really rotten cultural component. The other thing, too, is that though I really recognize how Uber has changed the way the world operates, I think there just are a lot of costs that come with it. The gig economy is now omnipresent in a jillion different start-ups, and it’s essentially created an entirely new class of workers that have eroded labor rights that have taken decades to build up. There are definitely these negative externalities that have appeared as a result of this company. I guess I’m just saying I don’t think you have to be an asshole to build a great company. That said, I do wonder if you have to be a jerk in order to build Uber, and I wonder if they could’ve done it without Travis at the helm.

I haven’t read too many start-up histories but Super Pumped is the only one I’ve read that has a significant amount of violence. Uber drivers are pressured to keep driving in adversarial conditions and subsequently murdered. Medallion owners whose prices are undercut by Uber regularly commit suicide. On rare occasions, passengers are assaulted by drivers who slipped through Uber’s lax background checks. Do you think it’s fair to say that Travis Kalanick has a body count?
I don’t know if I want to tag him with that, but what I will say is that Uber is one of the first start-ups that really crashed into the real world in a very different way than Facebook or Snapchat or whatever. That said, you know, you could argue Facebook has a body count, too: People spread anti-vaxx information, for instance. Uber literally changed how cities work and in a very short period of time. Deep, quick cultural change can often come with pushback, and violent pushback. Brazil is a key reflection of that. Uber parachuted into Brazil at one of the country’s worst economic points in its history. They’re in the middle of this deep recession, unemployment is skyrocketing, and folks would resort to committing violence in order to stay afloat. Add drivers in Uber cars with a bunch of cash, because it’s a cash-based economy, and in a lot of ways, you have a recipe for disaster. One of the big criticism I do have of Kalanick and some of his top staff, they probably should have acted a lot sooner than they did to fix some of those identity problems and safety issues. It was only until much later, under the new CEO, that they started to fix some of those problems.

Reading the book is very frustrating in that everyone in it is terrible, and now they’re all rich. That might be me editorializing.
No, I don’t think there are many redeeming characters in it, and I think that’s by design. It was hard to write because a typical narrative has a hero and a villain. I don’t think there’s any obvious heroes, or maybe there are too many obvious villains here. That said, I did try to humanize and make Travis less one-dimensional than he’s mostly made out to be.

To that end, I was wondering what your read on Bill Gurley is. By the end of the book, he comes across as the adult in the room, a guy trying to permanently exorcise Kalanick from the company. But he’s also Uber’s first big investor who maybe turned a blind eye to all this shit. Do you think he really has plausible deniability about the bad things Uber did, internally and externally?
I think Gurley in the end believed he was doing the ouster for the right reasons, and something they would even repeat to each other is, “We wanted to do the right thing.” Everyone at Benchmark, the VC firm that Gurley belongs to, believed that they were doing the right thing in pushing Travis out. That said, Bill’s an aggressive guy and had at least some indication of what the company was doing early on and some of the moves that it was making. It’s hard to credibly throw up one’s hands in the end and say, “Oh my God, what is going on here?!”

To be fair, I don’t think he knew about all the deep cultural issues like the trip to the escort bar [that Travis and regional managers took in South Korea] and the stuff about Susan Fowler [whose blog post blew the lid off Uber’s toxic culture]; there’s a lot of stuff that’s not in his purview. But yeah, I think it is an entirely valid question to be like, “How much of a blind eye did some of the folks turn?” It’s very convenient later on, not just Gurley, to say, “Oh my God, I can’t believe this is happening.”

There’s this detail in the book that Kalanick would not share internal information with investors, information that normally major investors would be privy to. Do you think post-Uber that anyone could pull off that level of withholding again?
I think the balance of power between investors and founders goes back and forth depending on the economic conditions of the moment. I get into the period of lean times after the dot-com bust, where Travis was begging for VC meetings and couldn’t get them, and when they did invest, they imposed onerous terms. And then we swing back to the times when money is flooding into the sector and VCs have to sort of just shut up and take whatever they can get to get in on these hot companies.

One concept I also get into is founder worship. The founder of a company is almost this man-god on the earth and what they do is worthy of bowing down. To be fair, they do a lot of hard stuff and it’s very difficult to build a business, and I totally respect that, but also Travis might represent the platonic ideal, or inverse, of what happens when you let a founder retain complete control and then have to resort to really drastic measures to deal with them.

Kalanick, and I guess Uber’s leadership in general, seems to really treat both enemies and allies with contempt. I was wondering whether you think a nonwhite or non-male CEO could get away with what he did professionally?
Since there’s such a dearth of nonwhite, non-male CEOs in Silicon Valley, it’s largely theoretical. But I think you’re right; a lot of what Travis and his leadership team did probably would not have been given the benefit of the doubt for folks who already have enough hardship in trying to raise venture capital, to be trusted as CEO, to build successful businesses. Empirically it’s already been shown that the odds are stacked against them. I’ve talked to female entrepreneurs and people of color who are trying to build companies and they just have an inherently difficult time raising money in the first place from a largely white, largely male environment. It’s not impossible, but it’s incredibly difficult to carry out [Kalanick’s] playbook.

In the course of recounting Uber’s story, were you worried about a sort of “Wolf of Wall Street” effect? I mean that the main players are self-evidently bad and not to be emulated, but bro-ey douchebags end up missing the point and idolizing them anyway.
I mean, if this book creates an entire class of shitty founders, you’re welcome to call me up in a year and tell me that I failed. I hope that’s not the case. In general, I like to give young founders a little more credit. I have a lot of criticisms of the Valley, but I think people generally recognize what went wrong inside of Uber now, and have a sense of wariness around how they want their own company to grow. Uber is a case study in going totally off the rails. I hope folks learned from that and I think that’s already kind of happening. I don’t see folks holding up Uber as the ideal. There are some Kool-Aid drinkers that were early in Uber that still fiercely defend everything that they did, and I think it’s going to be harder for them to defend that as time goes on.

In the section at the end of the book, when the stakeholders are trying to force Kalanick out, you end up as a character and are used as a part of their leverage. If Kalanick doesn’t resign, they’ll leak info to you. How does it feel to be treated as a pawn by a bunch of millionaires?
To make it clear, at the time, I had no idea that was how it was happening. I get into this in the book, but I am unaware that I’m a figure in the story and do not become aware until much later on when people decided to tell me that they used me as sort of a hostage negotiation. I don’t think that that view of the press as a weapon or something to be harnessed is uncommon out here. It was definitely a shock when I heard how it went down and why. I don’t like being used in a capacity that I’m not aware of. But I have to approach every situation with a level of skepticism. You have to just figure out what’s going on to the best of your ability and go from there. I will say, I’ve never reported a story like Uber, where everyone is lying and trying to advance their own agenda.

This sort of leads me to my next question: Why is everyone in Uber’s upper echelon a leaky psychopath?
I think it’s really indicative of the state of the company. It was a knife party, man. Everyone was constantly fearing their execution, and their evisceration in the press, or someone was trying to go after them so they would have to go to someone else. This is how a lot of investigative reporting works: There’s a dysfunction and that’s when leaks start to occur. It’s like Facebook — once the election happened there were leaks like crazy because people were just disturbed about what was going on. But I’ve never encountered a cast of characters that willing to kill each other.

The book ends with new CEO Dara Khosrowshahi’s installment. Has Uber changed since then?
This company’s done a very good job of saying, “We’re a new Uber! Uber 2.0! Blah, blah, blah, blah, blah, blah.” A lot of old-timers have left, but a lot of old-timers are still there. A lot of people who were there in the beginning who are waiting to cash out. And there are a number of folks who still really believe in Uber and Travis and what they do, so I don’t think you can just completely say, “We’re new and everything that happened before is over.” But I think more important than that: Company DNA is very crucial and it’s hard to change that over time, no matter who you install or who comes later on. Twitter is a good example of this. It was a mess from the beginning and it continued to be a mess through most of its life and multiple CEOs. Do I think that Uber is a complete garbage-fire mess like it was in 2017? No. Do I want to say that it’s an entirely different company? No.

Is there any way in hell that Uber or its competitors can achieve profitability?
Initially, Uber was conceived in a time when they were the only game in town and they could raise money insanely easily. That environment has passed and now there’s billions of dollars from companies like SoftBank going into the sector, ride-hailing is a commodity business so it’s easily replicable in countries across the world and Uber has to fight on every front, and not only that, they have the food-delivery business that’s another cash suck. Uber’s CEO has admitted that they don’t expect to be profitable in the near future. We have not been given any indication that Uber is a profitable business model.

Do you have any sense of when investors will stop throwing cash at this industry?
Everyone who invested in Uber early thinks it’s like a grand slam. The problem is all the value was captured by investors who got in early. Schmucks like you and me who might be retail investors on Wall Street (I should be clear, I don’t invest in any companies) are fucked because since day one of the IPO, Uber’s value has only gone down. One could argue that much of Uber’s value has been captured long before it ever became available to retail investors.

I noticed that you’re constantly talking about how tall people are in the book. What’s the deal with that?
Oh no. One of my early readers, a friend of mine, B.J., gave me a specific note on how tallness is something that I talk about a lot. I’m six feet tall, so I’m not like obsessed with height or short or anything. It’s not an obsession of mine. I feel like it’s like the physical attribute of people you just notice. It’s something that I was really into with Bill Gurley; he’s like the tallest man in venture capital. He’s like six-foot-eight or nine. Just this imposing figure, and a weird and awkward dude, and not exactly aggressive. I don’t know. The point of writing it the way I did was I wanted readers to feel like they got a sense of the characters, and I unconsciously thought that height was an important way at getting at that. But now that you mention that, I’m embarrassed.

I’m reminded of the stat that tall people are disproportionately represented in corporate leadership roles. Maybe it reflects some sort of unconscious bias.
That’s a really interesting point. I think people definitely discriminate based on height. Folks that aren’t as tall have insecurities about it. It’s an interesting thought to play out in terms of hiring and leadership roles. I was at this press conference yesterday [regarding the recent charges against former Uber employee Anthony Levandowski] with the new U.S. attorney in San Francisco, who is literally part of the Department of Justice, and that dude is huge. Probably six-foot-four or something like that. Maybe there is a reason I’m obsessed with it.

That’s a good question. That wasn’t as weird as I thought it was gonna be — like, “Is Waluigi a prominent figure in your mind when you write?” — but it was good.

I mean, is he?
Um … no Nintendo characters informed the writing of this book.

So with Uber now in reform mode, what’s the worst start-up in the tech industry?
I don’t know if I’d get in trouble by saying this is the worst one, but I can say that some of the tactics I’ve seen at certain companies have proved questionable. I think that DoorDash has gotten away with some sleight of hand with how they pay their drivers for a very long time. They did this system where they use tips to supplement wages. Their line around that was, “This is the way that we get to pay drivers the most.” And now they’re changing it after enough uproar; their new line is, “Our new way of doing this is the way that we can pay drivers the most.” It seems like a lot of bullshit. I don’t know how the math works out.

I probably shouldn’t say this, giving away a line of reporting, but a lot of early Uber employees have gone over to Lime, the scooter company. And they seem to have some issues there. I was talking to a source the other day who had some grievances with culture and behavior. I might have to start digging into them at some point. I really shouldn’t say that.

Well, you did. Fuck, marry, kill: Travis Kalanick, Garrett Camp, Ryan Graves [Uber’s first three principals].
Oh my God! I can’t answer that. I will get fired from my job as a New York Times employee. But I appreciate the question.

Fair enough. You can tell me off the record afterward.
Yeah, I will. Wait, no I won’t. No, I won’t.

Can you make your best attempt at describing Uber in doge-speak?
Wait, is that — This is where I’m 34 but I feel like I’m 54. Is this when it’s like, “So much wow”? I would be like, “OMG … subsidies, so much … net losses …” I’m so lame, but yeah, that would be my try.

Now can you describe your book in doge-speak?
Ugh, God I hate myself. Like, “OMG page-turner(?) Such Pulitzer.” Promoting a book is the worst.

Mike Isaac on Travis Kalanick’s Downfall and Uber’s Legacy