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Riding Shotgun With Uber CEO Travis Kalanick

May 18, 2017

In this exclusive excerpt from Adam Lashinsky’s new book, Wild Ride: Inside Uber’s Quest for World Domination, the author prowls the streets of San Francisco with the startup’s pugnacious CEO and learns how he feeds on adversity.

Love him for his audacious ambition or hate him for his tone-deaf ruthlessness, Travis Kalanick is a headline-grabbing corporate villain for the ages. Uber, the privately held company he runs from his base in San Francisco, has become a global phenomenon in the mere six years since it first began connecting ride-seeking urbanites with drivers via a simple smartphone app. Now operating in 76 countries, Uber booked $20 billion worth of rides worldwide in 2016 and brought in $6.5 billion in revenue. As its business has boomed, the startup’s investors have continued to bet big on Kalanick’s creation. To date the company has raised $17 billion in debt and venture capital, and has been accorded a gargantuan market value of $69 billion. At the same time, Kalanick himself has become infamous—seen by many as a brash, win-at-all-costs entrepreneur who’ll flout any rule to succeed, as well as a bro-in-chief enabler presiding over a sexist corporate culture.

Courtesy of Penguin Random House 

A new book by Fortune executive editor Adam Lashinsky, Wild Ride: Inside Uber’s Quest for World Domination, recounts the company’s stunning rise—and its headlong plunge into controversy. Lashinsky’s quest to tell the Uber story got off to a bumpy start: Kalanick at first threatened to torpedo his project before it started by hiring a competing author to write an authorized account. Over time, Kalanick relented and agreed to cooperate, and Lashinsky conducted hours of interviews with Kalanick and other Uber executives. In the following excerpt, Lashinsky walks the streets of San Francisco with Kalanick as the CEO confronts a nagging concern: Does the public’s perception of him match reality? Is he really an asshole?

I.

It is 7:30 p.m. on a sunny summer evening when I arrive at Uber’s San Francisco headquarters for an extended interview with CEO Travis Kalanick. I’m a bit surprised to see so few people in the office, given Uber’s reputation for long hours. It’s mid-July, so perhaps the young staff is out enjoying itself. But it is also possible the company’s workforce is mellowing—fatigued, by this point in 2016, from more than five years of galloping at breakneck speed.

Kalanick himself sets the pace. He’s just days away from his 40th birthday and still very much leading the young entrepreneur’s caffeine–fueled lifestyle. Over the years he has often had a steady girlfriend, but has remained resolutely unmarried. Multiple friends describe Kalanick as something of a homebody when not working, yet far more committed to Uber than to any other relationship.

A few minutes past the appointed hour, Kalanick arrives at his desk, where I’m waiting. He has a private nook at the far end of one floor, where he keeps some clothes as well as a diorama of Uber’s new headquarters under construction in the Mission Bay section of town. (Scheduled to open in 2019, Uber’s new HQ will be across the street from where the Golden State Warriors basketball team is building a new arena.) But to the extent that Kalanick sits, which isn’t much, it is at an open-plan desk at the edge of the company’s fourth-floor main offices. There’s nothing fancy or “corner office” about it.

After a year of researching Kalanick, his past companies, and Uber, I know enough to be flexible: He likes to play it loose, to at least affect an air of spontaneity. We haven’t discussed our agenda ahead of time other than that we’ll continue the conversation about his career that we began a month before in China. He tells me he has a few things he wants to show me before we start talking—that is, if I’m willing to accept an unconventional suggestion.

“Okay, you’ve got two choices,” he announces. “We can go in that room,” he says, pointing to a nearby conference room, one of many at Uber used for private meetings, “and I’m going to fucking pace back and forth the entire time. Or we can go for a walk.”

Portrait of Uber CEO Travis Kalanick on March 18, 2013. Jeffery Salter — Redux Pictures 

Understanding my true choice to be between “letting Travis be Travis” on the one hand and trying to pry information out of a penned‑in subject on the other, I opt for the walk.

Uber’s story isn’t strictly synonymous with Kalanick’s—the ride-hailing startup wasn’t initially his idea—but he is indisputably its central character. Kalanick supplied the critical insight that transformed someone else’s startup idea from merely interesting to undeniably groundbreaking, by hitting on the idea of enabling freelancers rather than hiring drivers and buying cars. And he has been Uber’s iron-fisted, omnipresent chief executive from the time it first gained traction and began expanding beyond San Francisco. As a result, Uber has become as identified with Kalanick as Microsoft, Apple, and Facebook are with Bill Gates, Steve Jobs, and Mark Zuckerberg, respectively.

Kalanick’s timing with Uber was impeccable. The company perfectly exemplifies the attributes of the information-technology industry’s next wave. It is emphatically a mobile-first business; if there had been no iPhone, there would have been no Uber. And it expanded globally almost from its beginning, far earlier than would have been possible in an era when packaged software and clunky computers were the norm. Uber is also a leader of the so‑called gig economy, cleverly marrying its technology with other people’s assets (their cars) as well as their labor, paying them independent-contractor fees but not costlier employee benefits.

Nicolas Rapp 

Today Uber employs more than 12,000 people full-time, about half in the Bay Area. Because we’ve grabbed our jackets—even clear July nights in San Francisco can be brisk—I assume a walk means we’ll leave the building. And we will. But first Kalanick explains that he wants to give me a tour of Uber’s offices. Like other hands‑on CEOs before him, Kalanick views his company’s offices not only as a reflection of the company’s values and aspirations, but also an extension of his own personality.

Jobs was the same way. Six months before his death he sat down next to me on a couch in his Palo Alto living room and proudly showed me a bound book of architectural drawings for the new Apple corporate campus he wouldn’t live to see. Months later he personally worked with an arborist to pick the apricot trees for the project.

“You know when, like, a city is made from scratch?” says Kalanick. “You’ve got clean lines everywhere. This is like a manufactured city. So this is ‘clean lines.’ We have five brand pillars: grounded, populist, inspiring, highly evolved, and elevated. That’s the personality of Uber.”

We’re standing near his desk, looking out over the nerve center of Uber’s offices, the row after row of adjoining desks a visitor sees after first passing through security. As Kalanick repeats these brand “pillars”—grounded, populist, inspiring, highly evolved, and elevated—I nod my head in acknowledgment. But I never completely understand what they are really about. It’s all a bit squishy to me, no matter how earnestly he explains them.

By “grounded” he generally means practical. Uber is the ultimate in practicality: It uses technology to move people from one place to another. Yet the concept takes on new meaning in the words spoken by the son of a public-works engineer. “Grounded is like tonality,” says ­Kalanick. “It’s functional straight lines, the whole thing. All of the conference rooms are named for cities. They’re in alphabetical order. It’s just very practical.”

I had read of Kalanick’s willingness to devote untold hours to superficial minutiae. Yet I hadn’t personally witnessed his willingness to dive into seemingly arcane and ethereal aspects of such a demanding business.

As an example of Uber’s “elevated” nature, Kalanick points to the acoustically pure ceilings in a conference room. A quiet freak—“I don’t like sound. I don’t do well with lots of noise”—he proudly identifies the building material, K‑13, that pulls off the effect. “When you have 800 people on this floor, the acoustic treatment makes it calm. So I can talk softly,” he says, lowering his voice to an almost awkwardly gentle murmur, “and you can hear me.”

Nearby is a corridor between the desks and an interior wall. Kalanick invites me to look down at the concrete floor, where an intricate pattern is etched with a series of intersecting lines. “Right here is the San Francisco grid,” he says. “I call it the path.” It is here that he paces back and forth throughout the workday, often on his cell phone. “In the daytime you’ll see me here,” he says. “I’ll do 45 miles a week.”

Nicolas Rapp 

The tour proceeds around the fourth floor. Kalanick shows me “New York City,” the conference room where Uber negotiated the deal in which it raised $1.2 billion, just before the company moved into the Market Street offices. “The first billion-dollar deal that blew people’s minds,” he says proudly.

We take an elevator to the 11th floor—one of a handful Uber has in the building—where Kalanick has created an austere setting, a place to mimic the entrepreneurial environment, with exposed drywall and smaller-than-usual desks.

“When you’re an entrepreneur—at least the 99% of entrepreneurs that are not Mark Zuckerberg—you have hard times,” he says. “So this right here is what I call the cave, because when you’re going through hard times you’re in the dark, you’re literally in some dark place. It’s a metaphor.”

Down on the fifth floor are areas with conference rooms named after science-fiction books. Kalanick knows the sci‑fi canon the way a Civil War buff can rattle off important battles. One section is named for Isaac Asimov’s Foundation series, another for The Martian, a third for Ender’s Game. He brands the sci‑fi theme “highly evolved,” by which he means the future. Uber is a company obsessed with the future. Elsewhere there’s a central area meant to evoke an Italian piazza. The hallways leading to it are confusing, by design. In Kalanick’s worldview, disorientation is good. “So if you are a resident you know where everything is,” he says. This is his version of populism. “If you are a guest, you’re lost. So you can tell who’s a resident and who’s a guest.”

II.

We finally leave the building by slipping past Kalanick’s desk to his secret exit and a staircase that leads directly out onto a street around the corner from the entrance to Uber’s office. The plan, he tells me, is to walk down Market Street, the main thoroughfare that cuts through the center of downtown San Francisco, to the Embarcadero along the waterfront. From there we’ll head to the touristy Fisherman’s Wharf area and then toward the Golden Gate Bridge. Despite the brilliant sunset, the temperature is falling.

Kalanick, forever an Angeleno, can’t bear it. “This is the most upsetting thing for somebody from Los Angeles,” he says. “That’s why I sometimes do weekends in L.A. Just to be at the beach.”

Kalanick is in a reflective mood, and as we walk he riffs on all manner of things. I remark, for example, on how little I’ve heard of late about Square, the payments company headed by Twitter founder Jack Dorsey, whose offices, for now, are in the same building as Uber. Although Uber is private and Square (sq) is publicly traded, Square has become decidedly low profile. Muses Kalanick: “We don’t really have that luxury.”

We begin talking about Kalanick’s entrepreneurial history, including his desperate hunt for funding in the early 2000s at his peer-to-peer file-sharing startup, Red Swoosh. By the time we hit the Embarcadero, the curvilinear street that runs along the waterfront between the Bay Bridge and the Golden Gate Bridge, dusk has set in. I wonder aloud if he’ll be recognized during our walk. Not likely, he says, so long as we’re in conversation and outdoors.

Out past Fisherman’s Wharf, we step into an In‑N‑Out Burger, the iconic SoCal fast-food chain and a Kalanick favorite. By now we’re discussing driverless cars and Kalanick suggests big moves are ahead that he can’t yet discuss. He lets on that this six-mile walk, always including the stop at In‑N‑Out Burger, has become a summer-evening routine and that he typically walks it with one person he won’t identify. I later learn his walking partner is Anthony Levandowski, the ex–Google autonomous vehicles engineer who went on to found Otto, a self-driving truck company. Uber will purchase Otto for $680 million just a few weeks after our walk, and Kalanick tells me he used his time with Levandowski to absorb the technology and business plan vision for autonomous vehicles. (Uber and Alphabet are now embroiled in a lawsuit. See our article on “What Could Take Down Uber?”)

Having discussed Kalanick’s entrepreneurial days, I want to know how he views the bigger, more established company Uber has become. His answers betray a reluctance to think of the company that way. He doesn’t know everyone at the company anymore, but he still conducts hours-long interviews with top prospects. Kalanick explains that he likes to simulate what it would be like to work with someone before hiring them.

CHINA-BEIJING-UBER FOUNDER-EVENTS (CN)Kalanick speaking at the Baidu World Congress in Beijing in 2015. Last summer the Uber CEO shocked many observers by admitting defeat in China. Zhu Wei — Xinhua News Agency/Getty Images 

I ask if he likes running a big company. “The way I do it, it doesn’t feel big,” he says, falling back on a favorite trope: that he approaches his day as a series of problems to be solved. He obviously thinks of himself as troubleshooter-in-chief as much as a CEO.

Bigness clearly is scary. “I would say you constantly want to make your company feel small,” he says. “You need to create mechanisms and cultural values so that you feel as small as possible. That’s how you stay innovative and fast. But how you do that at different sizes is different. Like when you’re super small, you go fast by just tribal knowledge. But if you did tribal knowledge when you’re super big it would be chaotic and you’d actually go really slow. So you have to constantly find that line between order and chaos.”

How, I wonder, does he plan to manage the transition out of the pure startup stage, now that the company is no longer composed of a bunch of young, single people with nothing in their lives but work? “I call it the red line,” he says. “In a car, you can go fast. But you have a red line. And everybody has their own personal red lines. You want to push into that red line and see what that engine’s made of. You might find you’ve got more under the hood than you thought. But you can’t sit over the red line for too long. And everybody’s got their own personal red line.”

He points out that already there are many “Uber babies” and that parents tend to be more efficient than childless people with fewer constraints on their time. There are limits, though, to Kalanick’s aspirations for work/life balance for his employees. “Look, if somebody’s producing more, they’re going to rise faster. That just is. There’s no way around that.”

III.

After more than three hours of walking, the night has turned cold and dark—and the conversation turns deeply personal. We discuss the narrative arc of how Uber has progressed from media darling to media villain. Kalanick was an almost willing accomplice in this metamorphosis, often managing to stoke the fire by playing the villain himself. He refers to these actions as his “little moments of arrogance where I say something provocative.”

I ask if he cares what people think. “Yeah,” he says, acknowledging some regrets. “It’s not good for Uber. It’s not good for me. It’s not good for the people that I’m talking to. It’s bad for everybody.”

Part of his problem is that Kalanick seemingly isn’t able to hide his defensiveness or his annoyance. He ascribes his moments of pique to “fierce truth seeking.” Someone willing to say exactly what he thinks, empathy be damned, will be judged harshly. He’s not alone. It’s a trait that has been repeatedly ascribed to Steve Jobs and Jeff Bezos, as well as to Kalanick’s contemporary, Elon Musk. Kalanick is aware of this, referring to the “meme that founder-CEOs have to be assholes to be successful.” He rejects that notion, but he’s obviously just short of obsessed by it.

“I think there’s this question out there,” he says, shifting away from general memes to himself. “ ‘Is he an asshole?’ Since you’ve spent time with me, one of the big questions you’re going to get is, ‘Is he an asshole?’ ”

Engineer that he is, Kalanick wants to believe there is a scientific answer to the question. I suggest the answer is and always will be in the realm of opinion, not fact. He rejects this. “Understanding whether it’s real or not, like do I trigger something in certain people that’s related to something that I didn’t do? Or am I an asshole? I’d love to know.” He continues: “I don’t think I’m an asshole. I’m pretty sure I’m not.”

But I want to know if he cares one way or the other what people think. “What you’re hearing me say is that if you are a truth seeker, you just want the truth. And if you believe that something is not the truth, then you want to keep seeking for truth. That’s just how I’m wired.”

Kalanick is unlikely to ever hear the version of the truth he craves. Weeks after our walk, New York magazine publishes an interview with Bradley Tusk, the political consultant who has worked for Uber on multiple regulatory fights. In discussing his own willingness to take “a few hits” for the right reasons, Tusk compares himself to Kalanick. “He understands to achieve really big things, you’re going to piss a lot of people off,” Tusk says. Then the writer asks Tusk if Kalanick is an asshole and describes his reaction: “He hesitates. ‘Are we off the record?’ I tell him we are not. ‘No, he is not an asshole.’ ”

The “asshole” question was answered for good in the eyes of many early in 2017 when a video of Kalanick berating a driver went viral. Kalanick suggested publicly the incident showed his need to “grow up.” But he made this statement having recently entered his fifth decade. Youthfulness alone can no longer explain his behavior.

Kalanick, who at this point in our walk is cold and tired, offers to continue to the Golden Gate Bridge, likely another half-hour down the trail, or to call a car and head back to the Uber offices. I’m tired and cold too, but I ask him to choose. “I think we’re getting a car,” he says.

He pulls out his smartphone and summons an Uber. It takes the driver just a few minutes of listening to our discussion to realize that the “Travis” he has picked up—all Uber drivers have the first name of their paying passenger—is the company’s CEO.

DRIVER: Are you Travis?

KALANICK: Yeah. How you doing, man?

DRIVER: I never met you.

KALANICK: Yeah, yeah.

DRIVER: How you doing, man?

KALANICK: I’m good. I’m good.

DRIVER: I can’t believe it.

KALANICK: How’d you connect the dots?

DRIVER: I was looking in the rearview mirror a little bit. And you looked so familiar. Damn, I’m with the CEO.

KALANICK: It’s good to meet you, man.

DRIVER: Thanks, man.

KALANICK: How long you been doing the Uber thing?

DRIVER: A year, about a year and two months.

KALANICK: What were you doing before?

DRIVER: I was doing it part-time because I live in San Francisco, so I need more money.

KALANICK: For sure.

DRIVER: And then I got laid off, so I’m doing it full-time now.

The driver explains that he’d recently been laid off after 16 years at AT&T (t), where he worked in tech support. Kalanick asks if he is “pumped” about being able to control his time now as an Uber driver, and the driver says he likes the flexibility, though the money could be better. When Kalanick says that Uber has lots of ways for drivers “to make an extra buck,” the tide turns. “Well, your tech support really sucks,” the driver says. “That’s true, I’m working on it,” says Kalanick, asking for a few months to fix what’s broken.

The driver also complains that he’s not getting emails and text messages informing him of guaranteed hours, an incentive program that is a ­staple for drivers trying to make a living on Uber. He then gives the CEO a lesson on how drivers abuse Uber’s rules. For example, many drivers screen rides to avoid undesirable destinations, like far-out suburbs.

By the time we get out of the car, at the same side entrance where we exited the Uber building hours earlier, it’s nearly 11 p.m. Kalanick promises to follow up with the driver’s concerns. (At 11:07 p.m. he forwards me an internal response from a “senior community operations manager” in Chicago promising to look into them. I ask later if he would have been as responsive if I hadn’t been in the car. “You know how many emails and texts I send from cars, from drivers giving me feedback?” he asks. “Uber product managers are like, ‘Oh man, here we go.’ ”)

IV.

Last August, Kalanick stunned many Uber watchers by admitting defeat in what he had touted as the company’s most important future market: He sold Uber China to Chinese rival Didi. It was perhaps the most painful failure of his career. But even here the full story is more nuanced. Uber was losing a billion dollars a year in China. And by selling to Didi—which made his company Didi’s largest shareholder and brought Didi onto Uber’s board—Kalanick in one fell swoop also achieved one of his greatest triumphs.

All of a sudden he had parlayed a failing $2 billion investment into a stake worth $6 billion in a rising Chinese monopoly. And by eliminating a no‑end‑in‑sight drain on the company’s cash reserves, he shored up Uber’s finances, paving the way for an eventual initial public offering of Uber’s shares in the United States.

Meanwhile, Uber showed it hadn’t lost the appetite to dream big. In late October 2016 its top product executive, Jeff Holden, published a 99-page white paper devoted to Uber’s research into flying cars, of all things. He dubbed the project “Uber Elevate.” The report begins: “Imagine traveling from San Francisco’s Marina to work in downtown San Jose—a drive that would normally occupy the better part of two hours—in only 15 minutes.” It goes on to explain Uber’s vision for a network of cars that take off and land vertically and the infrastructure it would take to build it.

The paper might have seemed like an elaborate prank but for its detailed discussion of “market feasibility barriers” and its 17-person contributor-and-reviewer roster, including scientists from NASA, Georgia Tech, and MIT. One of those reviewers, a 30-year NASA veteran named Mark Moore, joined Uber full time in early 2017 as director of aviation engineering. Whatever Uber’s shortcomings, it’s safe to say it literally considers the sky to be the limit.

For all his professed just-the-facts practicality, Kalanick loves nothing more than to bat around ideas, the zanier the better. In the summer of 2016, I traveled by private jet with Kalanick and several top Uber executives from Beijing, the Chinese capital, to Hangzhou, the coastal city near Shanghai that is home to Alibaba and thus an important hub of the Chinese Internet business.

Before takeoff, Kalanick wonders aloud to Emil Michael, his top dealmaker and fundraiser, if Uber could go public without investment bankers. Michael, a lawyer by training, suggests instead a reverse merger, a somewhat dubious technique whereby a private company buys an inferior public company for its listing. Kalanick suggests using no bankers but giving 3% of the capital raised—the fee bankers would have received—to charity. When I suggest giving that money instead to drivers, Kalanick lights up. He says he wants to give equity to drivers, something upstart Juno has begun doing, but Uber has found the securities-law implications to be complicated.

Once airborne, Kalanick turns positively pensive. He tells me he has long dreamed of being an investigative journalist, having once read an anthology of reporting about the Khmer Rouge in Cambodia. The “dream job,” he says, appeals to his sense of justice. He even has an idea for an investigative project: He and I need to go to Mumbai for six months, he says, and live in the slums and write about the experience. “I’m going to grow out my hair and wear different clothes and go native,” he says.

I learn over time that this is partly how ­Kalanick amuses himself and partly a reflection of his earnest side. He may well be moved by the plight of the Cambodian people under the murderous Khmer Rouge or by the slum dwellers of Mumbai, yet he hasn’t done anything about the homeless in his own city of San Francisco. His ideas are thrilling but also baffling. And he relishes challenges to his flights of fancy.

In one of my last conversations with Kalanick, I bring up the topic of Alexander Hamilton, in part to verify my recollection that Kalanick had been interested in the first U.S. Treasury Secretary long before Lin-Manuel Miranda’s epically successful musical exploded on Broadway. Why, I ask, did Kalanick admire Hamilton so much when he first read Ron Chernow’s biography?

“There’s much to admire about him,” he says. “He was an entrepreneur in his own time. But instead of creating a company he was creating a country. He was right at the center. The U.S. would be a very different place if he wasn’t there. He was a philosopher, but he was also an execution guy. He had a lot of great qualities. I think just so much about how he saw the future. And in many ways America lived that out, and I think we became a prominent country because of his vision.”

Hamilton didn’t know when to keep quiet, and his list of enemies was long. Did Kalanick identify, I wonder, with the extraordinary amount of public abuse Hamilton withstood? “Well, look,” he says, “this guy had a lot of adversity. We have this thing at Uber. We like to say, ‘Know what’s right, fight for it, don’t be a jerk.’ He just did what he thought was right. And when you do that, when you’re doing something really, really different, you’re going to have some naysayers. You just have to get used to that.”

Travis Kalanick, a jerk to many but not to ­himself, very likely will never get used to the naysayers. Adversity, after all, has become part of the journey.

Excerpted from WILD RIDE: Inside Uber’s Quest for World Domination, by Adam Lashinsky, to be published on May 23, 2017, by Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © 2017 by Adam Lashinsky.

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