The Book Report: Mike Isaac’s “Super Pumped: The Battle for Uber”

John Paul Rollert: Steve Jobs famously said that the type of people who wanted to work for Apple were those who long to make a dent in the universe. Jobs was speaking metaphorically, of course, which is a good thing, for the closest thing to an actual dent in the universe is a black hole, a region in space where the gravitational pull is so strong that nothing, not even light, can escape it. Such immense power to shape the world around us, and the dangers therein, are the subject of Mike Isaac’s new book, Super Pumped: The Battle for Uber. In it, Isaac tells the story of Travis Kalanick, the would-be tech titan who aimed to bend the universe but ended up falling from grace. It’s a remarkable story. And that’s why, with the support of the Harry L. Davis Center for Leadership and the Stigler Center for the Study of the Economy and the State, I’m pleased to have Mike here with us at the University of Chicago Booth School of Business for this episode of The Book Report. Welcome, Mike.

Mike Isaac: Hey, thanks for having me. (chuckles) (audience applauds)

John Paul Rollert: Mike, I’d like to begin with the epigraph—

Mike Isaac: Yeah.

John Paul Rollert: —you used for the book. You have two provocative and very different quotes. And I was hoping you could read them for us and tell us why you chose them to frame the book.

Mike Isaac: (chuckles) OK. So an epigraph is the quotes that sort of frame the beginning of the book. The first one is from Niccolò Machiavelli in 1513. And it says, “You must know there are two ways of contesting, the one by the law, the other by force. The first method is proper to men, the second to beasts. But because the first is frequently not sufficient, it is necessary to have recourse to the second.” And then the second one is from Travis Kalanick in 2015, 500 years later. “Being super pumped gives us super powers, turning the hardest problems into amazing opportunities to do something great.” (laughs)

John Paul Rollert: Why these quotes?

Mike Isaac: OK, so the Machiavelli: you know, everyone I talked to—I talked to probably 150, 200 people doing this book, reporting it out over the past five, six years, reporting on Uber—there were probably three different folks that people invoked when they talked about Travis. And probably the No. 1 was Machiavelli, just his sense of winning at all costs and whatever that took, whether it meant going through the most cutthroat tactics possible. And the other two were, I’m not sure if—. There was one that was Sun Tzu, but I’m not sure if that was self-aware or ironically.

John Paul Rollert: He’s the author of The Art of War.

Mike Isaac: Correct, the author of The Art of War. I almost went with a Sun Tzu quote, actually. And then the other one was President Trump, who creates this sort of reality around himself. Or people said that Travis, like Trump, creates a sort of reality around himself that becomes at once compelling and also sort of very forceful in his leadership. And so—. And then Travis’s second quote was the inspiration for the book, the title, Super Pumped, which (sighs) is probably like the most unself-aware version of how to deal with corporate culture, I would say. The company has 14 company values, like a lot of companies do. They have these mission statements on what they want their values to be. It was in the vein of Jeff Bezos at Amazon. He put forth 14 company values in the beginning—customer obsession being the first one— and a bunch of others after that. And Travis had this obsession with Amazon. So he took 14 company values, or abstracted values, and kind of ran them through a bro-speak translation engine, and then it came out with a bunch of different values, one of which was being “super pumped.” And employees were evaluated on their level of “super pumpedness,” and how pumped they were to come to their job. So it’s just sort of this idea of, I don’t know, just maybe an unself-aware CEO trying his hardest to embody what he thinks it is to be a CEO but also injecting a lot of himself into it.

John Paul Rollert: So we’ll talk a little bit more about what it, in fact, means to be super pumped as we go forward. But what’s interesting to me is that Machiavelli’s book is, of course, a manual for a young prince.

Mike Isaac: Yup.

John Paul Rollert: And in many respects, your book is a study of a young prince, a young prince at least in the tech industry, Travis Kalanick. And in the book, you talk a lot about Travis’s childhood, the origin story of Travis. I was hoping you’d say a little bit about his youth and what it was about his experience that helped give you a sense of the type of person he would end up becoming.

Mike Isaac: I think—I’ve been writing about tech for 10 years, and I think probably mainstream tech press has been for the past 15 or 20 years. So there’s a lot of mythology around how founders are created and formed and the things they do. Travis was interesting to me because he was a serial entrepreneur, right? Uber was not his first company. It was his third company. The first two he had, one was called Scour, which was kind of a protoversion of Napster. You could search for movies, or music, or whatever. It was like Google meets Napster, basically, if you remember Napster. And that was run out of town because it was sued into oblivion, basically. The RIAA and MPAA sued Scour for a quarter of a billion dollars, I think it was. And they never got off the ground, and there’s reasons behind that. 

And then his second startup was this company called Red Swoosh, which was decidedly less sexy. It was about a file transfer software and how to efficiently move data from one server to another. And that was a middling success, I would say. He sold it for a couple million dollars, which made him Silicon Valley poor, but rich anywhere else in the country. And then Uber was his third one. But I think the way he experienced VCs and his backers early on probably was the reason I got into his early days, and was what really informed what would shape his mentality later on, I think.

John Paul Rollert: Yeah, you tell this—I was hoping you’d share this wonderful story about Michael Ovitz, one of the VCs, also a superagent in Hollywood, who invested in his first startup, Scour. And he had a couple of bruising episodes with Ovitz. I would hope you would share.

Mike Isaac: Yeah, no, yeah.

John Paul Rollert: Because it seemed formative for the way he thought about, frankly, his approach to Uber later on.

Mike Isaac: I think the Ovitz—. So Michael Ovitz is—was, I guess I would say—a superagent in Hollywood. He formed one of the biggest talent agencies out there. And he was the early days of—or the early ’90s, I guess I would say—of what it meant to be a talent agency and scout for movie stars. And so he, with all his success and money, decided to get into the tech game because tech was blowing up in the ’90s and later 2000s. And so he invested in Scour, which was Travis’s startup. But as soon as they got sued, Ovitz couldn’t be seen, kind of, connected to this company that was basically making its bread and butter off of ripping off the content creators that created the whole industry that he started to begin with. So he immediately was like, I have to distance myself from this company. And he puts out a quote, or I think he attributes to someone, someone close to him puts out a quote distancing him from the press, from the company, in the Wall Street Journal. Basically, he knifes his own people, his own startup, when they’re in their most dire straits. And I think Travis, from that point on—. People I talked to that are around Travis were saying, “Look, this was the moment where I realized VCs, venture capitalists, are not there to support you. They’re out to make a buck and support their investment if they can. But if it’s gonna endanger them, then they’ll throw you under the bus when it’s possible.” And I really think he internalized that for the rest of his career, which would play out later at Uber.

John Paul Rollert: He clearly internalized it in terms of how he viewed VCs. Do you think he also internalized it in terms of how he understood how he ought to be running his own startup? Were there lessons he took from Ovitz, both either directly or inadvertently, that shaped the way he thought about his own leadership?

Mike Isaac: It definitely shaped how, and this is kinda wonky, but it definitely shaped how he dealt with governance, and cap tables, and shareholder agreements, and the level of control that he wanted to maintain for himself. One of the other things that later became popularized with Zuckerberg and Larry Page and Sergey Brin is this idea of dual-class voting structures in companies, which basically means—I have a room full of business students so I probably don’t need to tell you—but it’s basically: you can have a minority of shares, which represent an outsize level of power. And the one CEO basically can’t be removed no matter how bad things get at the company. And that has—. It was made popular in the Valley, I would say, with Sergey and Larry, and then Zuckerberg and Evan Spiegel. And now we’re seeing the worst of that, I would say, with the—. Travis later on sort of took this and held it very strongly. And then the ongoing amazing saga that is WeWork that’s playing out right now is the thing that will not, that’s been, by the way, that’s the gift that keeps on giving in terms of (audience laughs) how to deal with business ethics. I’m sure you’re teaching a whole course on that at some point. (chuckles)

John Paul Rollert: At some point, right? (Mike laughs) We’ll have to wait for the full flower of what’s going on with WeWork. So thinking about Travis’s early life, you have this experience of his first startup in Southern California.

Mike Isaac: Yup.

John Paul Rollert: And then he moves north, right? Goes to Northern California, founded his second startup. And one of the things to me that was really quite arresting was the way in which you described the culture of Northern California, and particularly Silicon Valley. So you describe it as a marriage of “antiestablishment counterculture,” and on the other hand, “ideas about the efficiency of individual greed and the gospel of creative destruction.”

Mike Isaac: Yeah.

John Paul Rollert: Given that was the earth in which Travis founded his second startup and also Uber, tell us a little bit more about that particular culture and how it formed him.

Mike Isaac: Well, I think if you go back, the San Francisco Bay Area was the roots for counterculture in the ’60s and the ’70s. This was ground zero for where the hippies were pushing back against the establishment. And I think that really translated into how people were thinking of software and building computers and building these companies early on. The sexy mythology around Apple was that Steve and Woz built these first computers in their garage in Cupertino, and later built that into a great computing business that changed the world. 

But the main point of that was that we’re not the incumbents. We are bucking the establishment. We’re trying to, sort of, turn things over and do business, do computing, give people more of a voice. And I really do think that folks in the Valley believed and probably still believe that to some degree. The unself-aware part is that they eventually become the incumbents, right? They eventually become the monopolists. And now we’re going through that sort of part with some of the companies now, and it seems to kinda repeat that. 

But in the beginning, that played out with startups flourishing, and coming up, and the idea that you can take, either be bootstraps or more likely take venture capital from folks, create a small business, and scale it to global levels with the scale of the internet, which was really the thing that changed the game for the Valley, in my opinion. It was game-changing for a lot of would-be entrepreneurs, right? And what I think, my guess or my thesis was: eventually we get to a point where the ubiquity of the iPhone, the ubiquity of Amazon Web Services, and the sort of flood of capital in the Valley make it really like a ripe time for a bunch of different people to grow startups that hadn’t been there in a while.

John Paul Rollert: Well, one of the peculiar qualities of this culture is the founder ideal.

Mike Isaac: Yeah.

John Paul Rollert: Which I wanna talk a little bit about. I was hoping that you’d read a passage.

Mike Isaac: Oh, yeah.

John Paul Rollert: From your book, page 74, actually.

Mike Isaac: Certainly.

John Paul Rollert: You talk about this founder ideal, and how it is very particular to Silicon Valley and informs the way in which people like Travis Kalanick think about their mission as entrepreneurs. So I’d hoped you’d read this particular passage and talk a little bit about it.

Mike Isaac: Yeah, so the thing that, I did not create the term, but the term that really resonated with me the most was this idea of being in a cult, right, and this cult-like mentality of worshiping founders in the Valley, right? And so what I wanted to describe is what people think of founders, or at least most people in VC think of founders. (reads) 

The most vaunted title in Silicon Valley is, has been, and ever will be founder. It’s less of a title than a statement. “I made this,” the founder proclaims. “I invented it out of nothing. I conjured it into being.” 

Travis Kalanick frequently compared building a startup to parenting a young child. A good founder lives and breathes the startup. As Mark Zuckerberg said, a founder moves fast and breaks things. The founder embraces the spirit of “the hacker way”; he is captain of the pirate ship. A good founder will work harder tomorrow than he did today. A good founder will sleep when he is dead (or after returning from a week at Burning Man). 

(audience laughs) 

Like Kalanick at Red Swoosh, a good founder shepherds his company through difficult funding environments but chooses his benefactors wisely. A good founder takes credit for his companies successes and faces the blame for its shortcomings. A good idea for a company, even if it lands at the right time and in the right place, is still only as good as the founder who runs it. Most of all, there can only ever be one real founder. 

And so I think I really—. The thing that I wanted to get out in this book is that I think there’s actually a lot of credit probably due to founders. And it’s funny, I talked to a lot of Uber employees who were kinda surprised at me giving—(disruption in audience)

That’s Uber right now. (audience laughs) giving a more evenhanded approach to this than they thought I would. But I think that founders have a really tough job, right? You’re creating a small business, essentially, out of nothing, and everything is pretty much stacked against you. You have to deal with Facebook either cloning you or buying you if you’re lucky, right? You have to deal with trying to have enough money to even promote your product so that anyone would even be able to find it in the App Store before or after the early days. There’s no way that people can even discover this stuff. So I do think it’s a very difficult job, and it’s not something that I envy. That said, I think it became sort of a religion (chuckles) in the Valley, you know? And that’s why I use the world cult. And I think even now, if you attack or critique, I would say, founder culture and this idea that maybe the young men—and it’s usually young men—the young men that are running these companies are not all-seeing, all-knowing geniuses, or have blind spots that we should think about. Or maybe if they are, again, predominantly white, young men, that they’re probably not building products that encompass the entire body of people that they serve. Like Facebook, for example, would probably be the best example. If it serves 2.7 billion people, how representative of that are the people that are building it? And so I really think this founder culture was created in a moment and mythologized by Valley folks as well as the press. And this is a weird, sort of, self-searching part: the press that covered the Valley in the original days, where the attractive story was talking about the guy in the hoodie in his dorm room building the next billion-dollar app.

John Paul Rollert: Well, you use the term cult.

Mike Isaac: Yeah. (laughs)

John Paul Rollert: So let’s follow that for a second because any good cult leader needs a series of articles of faith for the followers, right?

Mike Isaac: Oh, man.

John Paul Rollert: And you said actually in a talk a few weeks ago to the Commonwealth Club that the value systems that founders and tech companies put out is something striking to you because it isn’t something you necessarily see across American capitalism. And I’ll give the quote that you gave. You say, “They,” of these founders, “They have to form a value system that guides the company in what they’re doing."

Mike Isaac: Yup.

John Paul Rollert: And you distinguish that from similar figures in finance. You don’t find the same type of tendency to give necessarily these guiding values. And I’m curious about that distinction you see between finance on the one hand and Silicon Valley on the other.

Mike Isaac: I think if you were to, say, ask Mark Zuckerberg or Jeff Bezos or whatever if their ultimate goal was maximizing shareholder value, they would probably disagree with you strongly, right? Their goal is changing the world or being the best. Mark Zuckerberg’s literally connecting the world. It’s very messianic in its visions, and I think that is baked into how these companies operate in the beginning. And then I think it creates a system of role models that pass that down to the next generation of young entrepreneurs, whereas in finance, I think that the end goals are pretty clear, right? You’re delivering returns, and you make your picks in investments, and it’s pretty clear-cut. And whether you agree with it or not, it’s kinda straightforward. I am suspicious of some of the motivations of the folks in tech, or maybe it’s that some of these companies have—. I can’t decide if they sometimes like to rewrite their own history over time. Mark Zuckerberg gave a speech at Georgetown a few weeks ago in which he was talking about when he first created Facebook. It was kind of in response to the Iraq War, which I think was a very strong misreading of his own life. (chuckles) (audience laughs) But I get it. I get why you think you wanna do these things. And I do think that that becomes a sort of self-fulfilling and self-enforcing prophecy in the Valley, like you need to build the next big app that’s world-changing, and those are the folks that will perpetuate. I like to look at Y Combinator, which is a—there’s probably a whole book on the cult-like mentality of Y Combinator—but it’s a startup incubator in the Valley that’s very strongly self-reinforcing on probably largely libertarian, probably largely composed of young, white men. Although, they’ve been trying to do some more diversity stuff. But I don’t know. It’s a very insular culture that sometimes I’m not sure how self-aware they are, if they understand, if they believe their own stuff or not, if that makes sense.

John Paul Rollert: So you think—. You don’t know if they actually believe what it is they’re saying—

Mike Isaac: Well, that’s a thing I grapple with.

John Paul Rollert: Or how much, yeah—

Mike Isaac: I do think they believe it, but later on, we’re in a really interesting moment right now because I think we’re in a crisis of that belief. For the first time, that’s being actually shaken. And in the book, I say it’s 2016 for Facebook. Facebook was the first tech company to really get blasted for—at least for a lot of folks in California and a lot of folks on the Left—the election of Trump, and this idea that, oh, perhaps, even if it’s not necessarily true, we don’t have empirical evidence that Facebook made the election go one way or the other, but the thought was implanted into people’s heads that perhaps tech has a more outsize influence on how we operate in the world than we had suspected before. And perhaps we shouldn’t be treating it through the lens of, again, profiling the next young whiz kid on the cover of WIRED, or whatever, and I could say that ’cause I worked for WIRED, but on the cover of whatever magazine. Maybe we should be treating it as we treat reporting on Wall Street or reporting on the White House like we’re doing now. I think it’s a new power center. Anyway, I’m digressing. But I think they did believe it for a very long period of time. I think that belief is getting shaken right now. But I think it’s a very hard moment for a lot of folks in tech because they feel like they wanted to do the right thing, and so now they’re trying to figure out what the way forward is, if that makes sense.

John Paul Rollert: Well, let’s talk a little bit about the value system that Travis Kalanick trotted out. I think at the first time, at the X to the X event in the fall of 2015, which you give an account of here, if I remember correctly, a $25 million party in Las Vegas featuring Beyoncé, (Mike chuckles) among other things.

Mike Isaac: Literally Beyoncé.

John Paul Rollert: Literally Beyoncé, not the metaphorical Beyoncé, (Mike laughs) which would be great, too, but the actual Beyoncé is even better. And Travis, during this party, trots out this kinda philosophy of work and these 14 principles. You referred to them a little bit earlier. They include things like meritocracy and toe-stepping, principled confrontation, and, of course, super pumped. And you describe them, as a philosophy of work, as “Ayn Rand meets The Wolf of Wall Street,” (Mike chuckles) which, I will say for the crowd, is not meant as a compliment. (audience laughs) Can you say a little bit about this particular ethic, what strikes you about it, and how it captures how Travis was thinking about the way in which he was running Uber as this entity that might bend the universe?

Mike Isaac: So the 14 values are perfect because that’s his entire worldview but morphed into platitudes that were kinda cheesy and digestible by his employees. Half the people—he rolled them out at this $25 million Beyoncé extravaganza in Las Vegas, and the company was at a point where I think half the audience was on board with it and the other half was like, is this guy for real? Right? Actually people who didn’t believe in it. 

But I think the way he believed tech companies would thrive is creating this—the other part of that quote—is this Hobbesian environment where it’s just sort of kill or be killed, and the best will rise to the top, and pitting different parts of the organization against each other. And the theory was the best will come out on top, and we will create the best types of products internally because of that. I think, in reality, that just went totally in the wrong direction. And there were instances of, I don’t know, entire orgs sort of pitting each other against each other, or young, essentially, young kids having access to millions of dollars on the balance sheet to spend how they wanted in different cities based on little more than a gut reaction. And it was profligate spending that ultimately in retrospect was just like setting money on fire. And venture capitalists, the VCs, and the firms who contributed this money didn’t know where that was going. But I don’t know. And that would be, like, the least bad part of how it ended up. The worst part about it was the culture stuff, which was the very poor treatment of a lot of women in the company, or physical violence or assault against other employees. And the idea was as long as you were hitting your numbers and sort of making those growth—I would say it represented probably the worst of capitalism—as long as you were hitting the numbers, as long as you were growing your user base, as long as your city was doing well, you could turn a blind eye to that because you were a top performer. And that eventually caught up to them, but his idea was we’d sorta sort that out later on down the line.

John Paul Rollert: The financial ends would always justify the means.

Mike Isaac: Yeah, that’s right. At the basest level, I think the ends justify the means is a theme throughout the entire company, whether that was how they pushed into cities or how their valuation was growing, so don’t worry about how we got there.

John Paul Rollert: One of the qualities about those values that’s striking to me, and it’s also a theme that you see throughout the book, is a concern of being a victim, or victimhood. If you look, say for example, they created a manager scorecard where they took these 14 values and they would evaluate managers. I don’t know if they still do this, according to those 14 values.

Mike Isaac: Probably not.

John Paul Rollert: Probably not. (Mike laughs) Probably not today.

Mike Isaac: Yeah. Well, they changed the values—

John Paul Rollert: They have changed the values.

Mike Isaac: Yeah, on the press tour, trying to make sure it’s not the same company anymore.

John Paul Rollert: But if you look at this original set. So I’ll give one example. One of the values is: be an owner, not a renter. And the way in which that’s explained below is “not a victim,” right?

Mike Isaac: Right, yeah.

John Paul Rollert: This concern for victimhood, which seems as though it’s something that Travis himself comes back to constantly, why is that something of such importance? Why is that sense of maybe grievance connected into it as well too?

Mike Isaac: That’s a really good, yeah.

John Paul Rollert: Why is that such a theme for Travis?

Mike Isaac: I think that’s a very good insight. I think he had these moments where he probably, I mean this is the thing that I think goes to his deeper psychology is a lack of empathy in some regards. A lot of the way that he saw the world, I think, goes back to his—probably a lot of the way that we all see the world—goes back to his experiences in his younger days. And he was wronged by the people that were supposed to be supporting him. And instead of becoming a victim, or instead of just sort of setting up shop or closing up shop and saying I’m not gonna do this anymore ’cause it’s unfair, he pushed ahead and continued to work to try to raise the next round or try to make his company successful. 

And whatever, more power to him, he did that, and he ultimately ended up in Uber there. But I think he took that and imprinted it on the entire company and how it would work. And that’s just not a framework that works in every situation, especially when one of his big fears was becoming a big company. And I think there’s some logic to this, right? You don’t wanna become a Cisco or some bloated old tech company. HP, I think, was another example they used, or eBay. A less fast-moving company who can’t be as agile and would take hours to get, hours, if you’re lucky, to get a decision made on anything. 

And so his way of dealing with that was to not create basic systems that a company with 15,000 employees might need, like an HR system, for example, right? So if you have systematic sexual harassment internally, they can’t even report it correctly because that didn’t really exist. So I understood some of why he was doing it, but I think the ways that—. If he were a better CEO, or if he were able to mature as a CEO in time, before ultimately getting ousted, I think he would’ve tried different things to do that.

John Paul Rollert: Well, one of the things that your book does, which I think is really kind of captivating and harrowing, is it captures actual victims by virtue of their practices, right? So you give this catalog of consistent rule-breaking, sexual harassment, violation of all types of domestic laws, putting drivers in harm’s way overseas, committing privacy violations, which are deeply problematic. There’s almost a scofflaw sensibility that you see throughout the company during Travis’s reign. And I guess to a certain extent, if you’re looking into his mind and the very people at the top of Uber, how do they see the warrant for that? Do they try to justify that? And what is the justification?

Mike Isaac: I think it goes back to, again, let’s go to the messianic complex thing, right? If the system is unjust, one of the quotes I have is like, “The laws were BS, so we don’t need to abide by them,” right? And to some extent, I can kind of see that because let’s say Big Taxi—was what they called the taxi cartels—were involved in local government, lobbying government for a very long time. And you could argue that the incumbent had sort of sidled up to how regulations worked, and it was not exactly an open territory to challengers to that throne. And so I get that. And I think Uber’s reaction to that was to build new and creative ways to subvert how the law worked, right? Or at least how the system worked. And Greyball is one example of that, which I can explain if we wanna get into that, but it’s—

John Paul Rollert: Yeah, maybe. Greyball is perhaps the most extravagant example of law-breaking domestically, so why don’t you share a little bit about that?

Mike Isaac: Yeah, so I don’t know how familiar everyone is with the Greyball thing. But so I was covering Uber for the Times from 2015 to 2019. And if you remember in 2017, it was just nonstop scandal after scandal breaking at the company. It was like some managers were getting pushed out for God knows what and on a regular basis. And I wrote a story that sort of dug into the culture stuff. And I get a call from a new source that I had not spoken to. And they basically were like, “I have (chuckles) a cache of documents to show you about this one practice that was going on that you should find out about.” And I met this person, and it’s very clandestine, in this dingy pizza parlor. I describe it in here. And everyone was freaked out. All the people who talked to me also made sure I would never use the app to go meet them because they had hired all sorts of very impressive ex-CIA and NSA and FBI folks on the security team.

John Paul Rollert: Surveillance and privacy violation, yeah, yeah.

Mike Isaac: Yeah, yeah, exactly, yeah. Some very intense surveillance measures. And so essentially, you have to remember back in 2014, when Uber would push into cities, there was no framework around how any of ridesharing worked, right? And cities would generally resist when Uber just was like, I’m gonna set up shop and start offering Uber. And so Portland, I think, was probably the best example where Portland regulators essentially said, we will shut you down. We will hail your car, hail cars, and ticket or impound the vehicles once they get to our city if you try to do this. So Uber’s creative response to this was to use its software to—. Well, first they would dispatch some teams of these investigators to target who the transportation authorities and law officers were, tag them with this piece of software called Greyball, and make sure that it would turn their apps, essentially make their apps unusable. So they would sometimes look up their credit-card account numbers or go to their houses to sort of figure out who was using the apps, and then use this little snippet of code that was initially developed for not nefarious purposes, called Greyball, to keep them in the dark. And essentially, when they would try to hail the app, hail the car, they wouldn’t show up. So I found out about this. The technologist I talked to thought it was a really creative solution to a problem. The lawyers I talked to thought it was probably obstruction of justice. (audience laughs) You all can come down on whatever end of that you want to, but eventually, the Department of Justice ended up looking into it. And so I think the greater point was, though, the rules were stacked against them in a number of these cities. And so if those laws and rules were unjust, then it behooves us to try to find ways around them. And the company, when I finally approached them, their response was, essentially, there was no legal writing around how ridesharing is supposed to operate. So we’re not breaking the laws because they don’t exist.

John Paul Rollert: Does this point to a broader problem we have in Silicon Valley of a glibness about the idea of moving fast and breaking things, right? So in a business-school environment, we’ll often talk about creative destruction. And people love the creative side and discount the element of destruction.

Mike Isaac: (laughs) The destruction side, yeah.

John Paul Rollert: Right. But destruction you ought to really take seriously in this case. If you think, say for example with Facebook, move fast and break things ended up arguably breaking the American electoral system in 2016.

Mike Isaac: (laughs) Right, right.

John Paul Rollert: And you can be glib about that if you’re Uber, if you’re not the lives of, say, those drivers who were killed in certain parts of the world, people whose privacy was violated. To what degree do you think people like Travis, if not then, now, are grappling with the destructive side of creative destruction? Because obviously, a lot of them are sitting on millions of dollars, and so they have time for that type of reflection. (Mike laughs) But should we be taking that more seriously? We can laugh about this, but we’re now reckoning with the damage of that destruction.

Mike Isaac: 100 percent. I think, first, I’ll be fair to them. I don’t think anyone could have foreseen—. It’s hard to tell what some of these innovations are gonna do once you unleash them upon the world, right? And so it would be hard for me to have imagined that in Brazil, for example, when Uber sort of jumps into a socioeconomic climate that’s completely intense, right? Incredibly high rates of unemployment and economic upheaval. And then you add this, essentially, like a system in there where basically a bunch of the drivers were getting murdered because of the way they were, they didn’t do proper identity checks on people using the app. You don’t know what these tools are gonna do, right? And you don’t know how people are gonna use them, and that sorta plays out in real time. 

The other easy example is Facebook and the Rohingya Muslims being just sort of killed en masse in Myanmar, right? This is the thing that the internet has done, which is just put change, being able to change things in real time much faster than I think we’ve ever seen before, and being able to do that from basically anywhere in the world. Like a couple thousand people, now it’s like 30,000 people in Menlo Park can create these messaging apps or these social networking apps. Or in Uber’s case, transportation apps that totally change the social fabric of countries that the founders have never been in in the first place, right? So I think that’s the one, the defense of them, I would say, is they’re not familiar with that. But on the other hand, I think the mentality really is, and I get in a lot of arguments about this, is that this is a better way. We essentially are creating a better way. And kinda similar to the—. We can compartmentalize the destructive part or the negative part of this because what we’re creating is overwhelmingly going to be resoundingly positive, right? 

And there’s a real tension because I think now we are in a moment, I think a shared cultural moment, where we’re actually questioning that, where people, normal people, are actually questioning that thesis, and perhaps, or at least paying more attention to the people who are losing in some of this, right? Whether it’s the workers, the drivers who don’t feel that they’re getting a fair shake from Uber, or the Amazon workers who are not able to go to the bathroom because they can’t get their packages done on time, or whatever. I think now we’re collectively looking at that, and I think it’s worth looking at. But the mentality to sorta push ahead with this is that we’re pushing toward something greater and that you should trust us ’cause we know better, essentially.

John Paul Rollert: Well, I’m curious if the public is now forcing tech companies and individuals like Travis to reckon with the destruction side of creative destruction. One of the things interesting about your book is that Uber comes of age at this interesting inflection point where tech companies go from being unapologetically lauded.

Mike Isaac: Yep.

John Paul Rollert: Right? Even to a hagiographic quality in a lot of the business press, to now, to a certain extent, being bad guys, going from being these heroic buccaneers to scofflaws. And I’m curious to what degree that has changed, for companies like Uber, how they understand themselves, and what it says about the larger story of the development of Silicon Valley.

Mike Isaac: So I write about Facebook a lot. I write about Uber, obviously. Basically, all of these companies are going through a similar reckoning right now. The other thing, too, is that I think it happens so fast that all the employees inside have a real whiplash around it. We were the good guys, right? The whole reason I signed up for Facebook is because, this is them talking, because I wanted to provide storefronts to someone in Nairobi who can sell their stuff on their Facebook page online or whatever, or bring connectivity to different parts of India, which was another initiative that failed miserably. But they have these sort of far-flung ideas of why they wanna do it. 

And I get it. I get that this is the mission that you were sold on. And I think even if you look at, I look at DC as an interesting barometer for a lot of this stuff. Right now, I see senators, and both sides of the aisle, right? You can go look at Josh Hawley, who’s hammering tech on a daily basis, or you can look at Warren, who’s using Zuckerberg for a punching bag, right? Apolitically, it’s very popular to beat up on tech, and I think that means something. I think that it speaks to how people are feeling about some of these services. 

On the flip side of that, we all continue to use them at record paces. And the company’s user numbers are growing, and the revenues continue to grow. And it’s sort of, I don’t wanna go as far as to say it is addicting, but it’s just sort of, they have invaded into our, made themselves a part of our lives in deeper ways than we could’ve really seen. So there’s a tension there. I think we’ll probably get to a balance of people being more vocal about what they are OK with the companies doing with the products that they use. I do think that a lot of these services can provide, a lot of them are valuable products that provide services that I use. I took an Uber from the airport. I think they’re not going away. And I don’t know if the end result is to have all of this go away. But I think that when consumers can say, “This is what I am and am not OK with,” that’s what the companies are kinda dealing with and grappling with right now.

John Paul Rollert: As part of that reckoning, do you also think the business and tech press has rethought about the way in which they cover these companies?

Mike Isaac: Oh, my God, yeah. And I’ve had to do soul-searching on the articles that I’ve written, or have I been critical enough, or have we been critical enough? I really do think it’s a pendulum right now where if it was a long period of not being critical enough, now it’s probably a, I don’t wanna say overcorrection, but a hypercorrection, where the media’s just going all in on tech, like maybe it did hammering finance, basically, after the crisis. And it’ll probably get to some sort of equilibrium. Not to say that it’ll ease up or let them off the hook, but more just figure out what we want tech to look like in our lives. Because I don’t think the end result is Luddism or going to a point where we don’t use any of these services because I think we’re kinda too far gone for that. But I think it’s figuring out what we’re OK with there. But I think the press plays a very large role in that. And I hope we’re being responsible in how we cover the companies in the future. I hope I am.

John Paul Rollert: Well, with respect to Travis himself, as a way of closing the loop on him—

Mike Isaac: Yeah.

John Paul Rollert: He had this outsize ambition. He formed this extraordinary company. And a lot of what your book chronicles is how he found himself ultimately pushed out of that company.

Mike Isaac: Yup.

John Paul Rollert: And so he’s had time for reflection, right? A lot of what we’ve been indulging here the last few minutes is a reflection on the fate of tech over the last decade. To what degree do you think he’s also engaged in that type of reflection? (Mike laughs) Not only about tech more broadly, but Uber specifically. One would like to think that part of the responsibility of being this tech mogul, right, this larger-than-life figure, is that you not just have a public profile, but you take seriously the responsibilities that come with it. Is there any sense that there’s a greater depth to Travis in the way he thinks about the fate that you chronicle here in this book?

Mike Isaac: (sighs) I would like to have said he’s a totally changed person. I don’t think that’s the case. So he immediately jumped into another business, which is also really interesting, actually. It’s this virtual kitchen, ghost kitchens, which you should look into if you don’t know. It’s basically based on delivery apps and attached to Uber. But I’ve talked to folks who have said he’s amassed just as much shareholder control, amassed as much control on how the governance works and working his people 18- to 20-hour, or working his people overtime is what I would say. He’s hired a number of folks that were terminated from Uber as a result of the Holder report, which went through the company’s history of bad behavior, I guess I would say. 

So I don’t know, it’s hard for me to know if he has learned a whole lot, but he’s definitely learned to keep a lower profile, at least. He’s not out there and doing a bunch of press—or any press. And he’s still going to the Met Gala and doing that sorta thing, and he’s investing. That’s what lessons have we, or he, or anyone learned here is, he hasn’t really been—. The people that were involved in this weren’t completely ejected from polite society, right? This is still sort of turning. But I do think that younger founders are starting to think more about the types of companies that they wanna build, and maybe that’s the net positive.

John Paul Rollert: The young people who are entering Silicon Valley as Travis did 10 years ago or so have a greater sense of self-awareness about not just the possibilities for creation but the dangers of destruction from their creations?

Mike Isaac: I don’t think any founder wants to grow up to be an Adam Neumann, right? Or even necessarily a Travis Kalanick, right? You don’t wanna be the guy who’s filthy rich but also has to, I mean, we wrote a story a night or two ago on how WeWork is about to lay off 4,000 or 5,000 people this week, right? And they’re turning the custodial staff, they’re firing all of them, then rehiring them as contract workers because it’s a way to bring down their costs, which, I guess it makes sense on paper, but it’s a horrible thing to do to like thousands of people, right? So I just don’t think that this next generation of founders wanna be like that. I think there’s a more ethical version of capitalism that they’re aiming for. Because I still do think they believe in capitalism, but I don’t think they want it to be this sort of brazen Hobbesian environment that at least Travis had sort of espoused.

John Paul Rollert: Well, then by way of a closing question, one of the things I love about your book is it’s a wonderful study on leadership. And there are a lot of positive but many negative lessons in leadership one can derive from it. And so to the degree of an audience of young business leaders, I was curious, do you have a single takeaway lesson or maybe a couple of lessons from the book that maybe are both in the book, or perhaps one in writing it that you came to that you might communicate?

Mike Isaac: Yeah, I think one classic CEO mistake, and I see current successful CEOs in the Valley doing this, too, was just Travis surrounded himself with people who only agreed with him and never challenged him, right? And he was willing to ice out people who ended up pushing back a little too hard. And I’m seeing that happening at some big tech companies now, and it can be just dangerous ’cause you need to have people you can disagree with and that you’ll actually listen to and not just push out. I think that’s really important. 

And the other thin,g I do think, I think the ray of hope, too, is—. I’ve been doing a book tour and going and talking to, a lot of the cool part is a lot of young founders or would-be entrepreneurs are coming up. And this one kid on the first night of my tour, he came up and was like, “Sign my book, saying, ‘Don’t build your company like this,’” right? Meaning Uber. 

And I think the thing that is heartening is that, or the thing that I hope happens more is thinking about the type of culture you want from the very beginning instead of having to rewrite that years later or rewrite what the actual history is, do this sort of revisionist history that I think is never a good thing. Founders are such a part of the company. I also think that the reason there’s only one founder is because the founder’s DNA kind of stays with the company for years on, even after they might’ve been departed. So I think it’s really a good thing to think about what that culture is from the very beginning.

John Paul Rollert: The book is Super Pumped: The Battle for Uber. Mike Isaac, thank you for joining us here at Booth.

Mike Isaac: Thanks for having me. (audience applauds) (Mike chuckles)