The Indian city of Gurugram, which in Hindi means “village of the guru,” is a technology-and-business hub twenty miles south of New Delhi, reached by highways filled with auto-rickshaws, exhaust-spewing buses, and the occasional immovable cow. The city’s glass high-rises contain dozens of multinational corporations, including Pepsi, Google, and Microsoft. On a recent morning, a white S.U.V. pulled up in front of the building housing the largest Indian office of the ride-hailing company Uber, and out climbed Dara Khosrowshahi, the company’s new C.E.O.
In Uber’s minimalist lobby, Khosrowshahi was greeted by two local staff members, who led him through a traditional Hindu lamplighting ceremony called an aarti. The ceremony, which banishes negativity and invites in light and optimism, is intended to mark an auspicious beginning. Khosrowshahi smiled as he lit ghee-soaked wicks on a bronze lamp surrounded by rose and dahlia petals. A female Uber employee dabbed a red tilak dot on his forehead and handed him a bouquet of flowers. In a black blazer, white dress shirt, and slim-fitting jeans, he looked like a corporate executive who had just escaped from a New Age retreat.
A few minutes later, Khosrowshahi was ushered into the cafeteria to meet with a group of Uber’s India-based employees. He seemed weary. He had been in India a little more than twenty-four hours, and had flown in directly from a two-day trip to Japan, where he visited Toyota plants and lobbied government officials to let Uber expand in the country. Although Uber is losing money in India, it is growing rapidly, and Khosrowshahi’s frenetic schedule involved numerous meetings with Indian politicians and regulators, including one that evening with the Prime Minister, Narendra Modi. Local policy experts had been briefing Khosrowshahi on his talking points. He was advised to refer to Uber’s drivers as “micro-entrepreneurs”—a term that, as Uber India’s chief business officer put it, “warms a politician’s heart.”
In the cafeteria, the president of Uber India asked Khosrowshahi a series of parlor-game questions:
“If you could go back in time, what would you tell your twenty-two-year-old self?”
“To get the hell out of investment banking sooner,” Khosrowshahi said.
“What’s the last book you read?”
“Oof, it was, uh . . . I can’t believe I’m saying this. It was ‘Fire and Fury,’ the Donald Trump book.” People laughed.
“This is my first time in India,” Khosrowshahi, who is forty-eight, remarked when it was his turn to address the crowd. He had been denied a visa when he was the C.E.O. of the online travel company Expedia—because, he theorized, of his Iranian heritage and Muslim name. Clearly, he said, “Uber has more pull.” There was enthusiastic applause.
Khosrowshahi talked about Uber’s future, including its plans to go public in 2019 and its goal of growing to between twenty and thirty times its current size. Then his voice became sombre. “The company brought me on board because of a lot of things that happened in the past,” he said. “We were probably trading off doing the right thing for growth, and thinking about competition maybe a bit too aggressively, and some of those things were mistakes.” He didn’t need to list the mistakes, many of which had been widely publicized. “Mistakes themselves are not a bad thing,” he went on. “The question is, do you learn from those mistakes? 2017 has been a really tough year, but this is going to result in us being a better company.”
Last August, when Khosrowshahi accepted the C.E.O. job, he inherited one of the most successful, and most scandal-plagued, companies in Silicon Valley. Uber had been expanding aggressively, in part by treating obstacles—whether competing ride-hailing companies or government regulations—as inconveniences to be bulldozed over. In many respects, the strategy worked. Just seven years after Uber offered its first black-car ride, in San Francisco, it had become one of the world’s best-known brands, and one of the largest privately held companies, valued by investors at seventy-two billion dollars. Uber now has eighteen thousand employees and currently operates in seventy-three countries. In addition to its ride-hailing service, it offers takeout food delivery (Uber Eats), and its engineers are developing vertical-liftoff aircraft (Uber Elevate) as well as driverless cars—a project that is consuming vast resources, and that encountered a major setback in March, when a pedestrian in Arizona was killed by one of Uber’s autonomous vehicles.
Since joining the company, Khosrowshahi has played the role of flatterer, diplomat, negotiator, and salesman. He was selected by Uber’s board in part because of his personality: agreeable, unthreatening, comfortable with the kind of corporate talk that investors find reassuring. Uber’s previous C.E.O., Travis Kalanick, had built the company into an extraordinary success. Under his leadership, it also acquired a terrible reputation, as the embodiment of a strain of Silicon Valley culture that values results above all else. Khosrowshahi’s visit to New Delhi was, among other things, a visit to the scene of one of the worst episodes in Uber’s history. In 2014, a female passenger accused her Uber driver of rape. Afterward, Kalanick reportedly speculated that the assault was staged by a rival Indian car-hailing service called Ola, and an Uber manager obtained the victim’s confidential medical records. (The manager was subsequently fired, and Kalanick denies the reports.) It turned out that the driver had been reported for inappropriate behavior several times, and Uber had failed to do anything.
Last summer, a group of investors pushed Kalanick out of the C.E.O. role. Uber is under federal investigation, with five different lines of inquiry. Numerous civil lawsuits have also been filed against the company, involving gender discrimination, complaints from drivers, and a large data breach in 2016, which the company concealed. The dramatic decline of Uber’s reputation has shaken Silicon Valley, which likes to think of itself as a force for good, even when confronted with evidence to the contrary. Nick Beim, a partner at the venture-capital firm Venrock, told me, “This particular company was so far out on the spectrum. It has cast such a shadow over Silicon Valley.” At the same time, Uber’s continued financial success has reinforced the idea that ruthlessness will be rewarded. “Is it O.K. to condone unethical behavior if you make a lot of money?” Beim asked. “It shouldn’t be, but that’s the looming question Silicon Valley needs to take a stand on.”
Uber’s board hopes that Khosrowshahi will be able to repair the company’s image. “He is a relationship guy,” David Krane, the managing partner of GV, formerly Google Ventures, which invested in Uber, told me. “He is much more patient.” Arianna Huffington, who is on Uber’s board, brought up Marcus Aurelius, the Roman emperor: “He dealt with plagues and invasions and betrayals, and he always managed to remain imperturbable.” She has joked with Khosrowshahi that he shares the same qualities.
Khosrowshahi is now tasked with transforming this unwieldy, ambitious enterprise into a more traditional company, without sacrificing the attributes that made it successful in the first place. An Uber investor told me, “One of the words that was common parlance at Uber was ‘fierce.’ I love that word. But it can absolutely be taken too far.” The question, he said, is “How does Dara preserve the positive aspects of the culture and change the aspects that are in desperate need of changing while still competing fiercely?”
The idea for Uber originated with a few young tech entrepreneurs who wanted a more efficient way to hail taxis in San Francisco. In 2008, a Canadian software programmer named Garrett Camp began working on the concept of using a smartphone to summon a town car, and he went into business with his friend Kalanick, who had co-founded two file-sharing startups. (The first, called Scour, which facilitated file-sharing of movies and music, was sued for copyright infringement and went bankrupt.) Uber initially focussed on black-car limo service, but Kalanick soon adopted the model of the company’s chief competitor, Lyft, allowing drivers to use their own vehicles to transport passengers.
From the start, Uber’s business was predicated on breaking rules. Taxi service in most cities was tightly controlled, and the company, instead of attempting to persuade regulators to let it operate, chose to ignore many of the regulations. As a result, Uber was in a combative stance at all times. (Kalanick once said, “We’re in a political campaign, and the candidate is Uber and the opponent is an asshole named Taxi.”) On the day, in 2010, when Kalanick was named C.E.O. of the company, which was initially called UberCab, a cease-and-desist letter arrived from San Francisco’s transit authority and the California Public Utilities Commission, claiming that the new company was clearly a taxi service and therefore fell under their jurisdiction. According to Brad Stone’s book “The Upstarts,” Kalanick simply dropped the word “Cab” from the company name and otherwise dismissed the letter.
As the company expanded to other locations, including New York, Seattle, Chicago, Boston, and Washington, D.C., it employed the same strategy: avoiding contact with local authorities until after the service had launched. Guerrilla teams were sent into foreign cities, beginning with Paris, in 2011, and London, in 2012, where they followed a similar script. In many places, users greeted Uber enthusiastically. But the company’s arrival also prompted street protests from taxi-drivers, lawsuits from regulators, and accusations of tax avoidance. Uber was fined and banned around the world. In France, its executives were arrested for running an illegal service. In Seoul, Kalanick was indicted in absentia.
In spite of the controversies, Uber was admired by investors in Silicon Valley and on Wall Street, many of whom thought the business exemplified industry disruption. In February, 2011, the venture-capital firm Benchmark became Uber’s lead investor, providing twelve million dollars in financing, at a company valuation of sixty million dollars, and a Benchmark partner named Bill Gurley joined Uber’s board. Two years later, the valuation, at least on paper, had increased to $3.5 billion. Rarely has a stake in a private company increased in value so quickly, and other investors took note. Over time, TPG, Menlo Ventures, First Round Capital, Lowercase Capital, Goldman Sachs, Fidelity, and SoftBank vied to become Uber investors. Kalanick pitted potential investors against one another and, when taking money, dictated transaction terms that gave him an unusual amount of influence, including effective control of a majority vote on the board. A dynamic formed in which the co-founder had leverage over the people providing him financing, meaning that Uber had nearly unlimited access to capital and relatively few constraints on its actions.
In September, 2015, Kalanick arranged a corporate retreat in Las Vegas. Employees were treated to parties and musical performances by Beyoncé and the d.j. David Guetta. The centerpiece of the retreat was a whimsical presentation in which Kalanick, dressed in a lab coat, introduced fourteen cultural values that he had developed with Jeff Holden, Uber’s chief product officer, who had joined the company after a long tenure at Amazon. According to one attendee, Kalanick offered lengthy disquisitions on the values, which included such phrases as “superpumped” (one of Kalanick’s favorite words), “meritocracy and toe-stepping” (the best ideas should win, and people shouldn’t be held back by concerns about offending their colleagues), “let builders build” (don’t try to restrain high performers), and “always be hustlin’.”
January of 2017 marked the beginning of an awful year for Uber. The company had grown preposterously fast. Eric Meyhofer, the head of Uber’s Advanced Technologies Group, told me, “We went from zero to seventy billion dollars in seven years. Ford went from zero to seventy billion in seventy years.” (He described working at the company as akin to riding “a lit rocket with your head out of the window.”) Yet Uber lacked the infrastructure of an established business. There was no chief financial officer or chief operating officer, which was unusual for a firm of such size operating in a heavily regulated industry. On January 27th, the company found itself in the midst of a public-relations disaster after President Trump issued a sweeping immigration ban, which prompted spontaneous protests across the country, including one at John F. Kennedy International Airport, in New York. A taxi union announced that, in solidarity with the protesters, its cabs would not pick up passengers at the airport. Uber told riders that it would suspend surge pricing, which increases fares during times of high demand. The public interpreted the move as an attempt to undermine the taxi strike. (Uber insists that this was a misunderstanding.) A “Delete Uber” campaign started on social media, and two hundred thousand people wiped the app from their phones.
Around the same time, Uber hired a new head of human resources, Liane Hornsey, who came from Google. Hornsey said that when she informed professional contacts about her new position, she “got this really weird vibe back.” People told her that Uber had a bad reputation, and said, “Oh, they really need you.” Hornsey’s initial impression was that many employees seemed anxious and overworked. Kalanick had promoted the idea of internal competition, with different teams battling against one another on the same project, which led to secrecy, lack of coöperation, and animosity among employees. “There was no sense of trust, no sense of ‘We’re building this together,’ ” Hornsey said.
Problems of gender discrimination weren’t as immediately obvious. “There was some stuff in the data that said it was laddish,” Hornsey said. “But it didn’t punch me on the nose.” Then, on February 19th, a former Uber engineer named Susan Fowler posted a memo online, alleging a disturbing pattern of sexual harassment that Uber’s human-resources department had failed to address. The memo came out on a Sunday, and Hornsey was in the car with her husband when she first read it. She was stunned. An emergency meeting was convened, during which Kalanick and the most senior women at the company—Hornsey; Rachel Holt, Uber’s head of North America; and Rachel Whetstone, the head of public and government relations—discussed what to do. Huffington, the only woman on the board, participated by phone.
The tone of the meeting was grave. “I didn’t hear any question of ‘Should we fight this, is this wrong, is this not true?’ ” Hornsey said. “I just heard, ‘Bloody hell, if this is true, we need to get serious.’ ” The company hired Eric Holder, the former U.S. Attorney General, who is now a partner at Covington & Burling, to lead an external investigation into Uber’s culture. Another law firm, Perkins Coie, was retained to investigate the Fowler allegations and other accusations of misconduct. Two days later, Huffington, who was acting as a sort of in-house corporate therapist, proposed an addition to Uber’s cultural values: “No brilliant jerks allowed.”
The negative news continued to accumulate. On February 23rd, Waymo, the autonomous-driving unit founded by Google, filed a lawsuit against Uber, alleging that it had stolen confidential information pertaining to lidar, a laser-based scanning technology. On February 26th, a high-ranking Uber employee was dismissed after the company discovered that he had left his previous job, at Google, over a sexual-harassment claim. Two days later, just as Uber was preparing to announce measures intended to repair its relationship with drivers, Bloomberg posted a dashboard video that showed Kalanick riding in the back of a luxury Uber black car, partying with two young women. In the video, Kalanick gets into an argument with the driver after he complains about Uber cutting rates and making it hard to earn a living. The argument escalates, and Kalanick angrily tells the driver, “Some people don’t like to take responsibility for their own shit. They blame everything in their life on somebody else!” Three days later, the Times reported on a secret internal Uber program called Greyball, which gave law-enforcement agents and government officials a fake version of the Uber app to impede investigations of the service. Then reports emerged about another covert program, called Hell, which Uber had used to identify drivers who were working for Lyft and lure them away.
Lyft’s corporate image, including its puffy pink logo, was more welcoming than Uber’s, and the company was notably scandal-free. As riders defected from Uber, Lyft went from underdog to formidable competitor, raising $1.7 billion and growing its share of the American market to more than thirty per cent. Morale among Uber employees, meanwhile, was low. Wayne Ting, a former general manager of Uber in San Francisco, who is now Khosrowshahi’s chief of staff, told me, “I think in 2017 a lot of us were learning about some of the stuff that was happening from the media. It was shocking, it was inexcusable.” Ting described the year leading up to Kalanick’s departure as an “out-of-body experience.” “It prompted a lot of reflection,” he said. “Do I want to stay? What are the things I need to see change in order for me to want to stay?”
One former Uber employee told me that people in the San Francisco office were concerned—but not for the reasons the headlines implied. “The elephant in the room was whether the business model even works,” he said. Uber was spending billions of dollars to subsidize rides in order to keep rates low and passengers coming back. Its competitors were doing the same thing. The only way Uber could become profitable was to both increase the volume of rides and raise the price of each one. But as long as Lyft or another rival was offering discounts, increasing fares was impossible, because consumers would simply switch to the cheaper app. And as long as venture capital continued to flow into ride-hailing, Uber’s rivals would continue to offer discounted rides. “How do they reduce the subsidies for the rides and not lose volume is the big math puzzle,” the former employee told me. In 2017, Uber grew substantially, but it also reported $4.47 billion in losses.
In early June, Uber announced the results of the two investigations into workplace misconduct. The company had fired twenty employees and placed thirty-one others in training or counselling. On June 11th, the Uber board, including Kalanick, gathered to hear a presentation on the findings of Holder’s team, which had reviewed three million documents and interviewed two hundred current and former employees. The report painted a harsh picture of the company and recommended forty-seven changes, including restructuring the board of directors to make it more independent and restricting alcohol and drug use at company events. A compliance consultant described the report as “one of the most remarkable discussions of a complete workplace culture disaster that has ever been rendered for a multi-billion business. If you changed some of the business and legal language, you might well think you were reading a report on Animal House.”
The week before the board meeting, Kalanick’s parents had been in a boating accident. His mother had died and his father had been seriously injured, and Kalanick was grief-stricken. The board discussed whether Kalanick should take a leave of absence, to mourn as well as to relieve the barrage of negative publicity. According to a person familiar with the meeting, at one point David Bonderman, a board member and a co-founder of the investment firm TPG, told Kalanick, “Travis, frankly, I cannot imagine this company without you, and I cannot imagine this company with you.” The board asked Kalanick to take an open-ended leave. In the meantime, the company would be managed by a committee of sixteen executives. Nine days later, two partners from Benchmark surprised Kalanick by handing him a letter from a group of investors asking him to resign immediately and threatening to publicly campaign against him if he did not. It wasn’t clear what had changed since the board meeting, but Kalanick complied and stepped down.
Khosrowshahi sometimes wears a T-shirt with the words “We Are All Dreamers” printed across the front. He often speaks of his experience finding asylum in America after his family fled Iran, in 1978. When Trump issued his executive order on immigration, Expedia joined other technology companies in a declaration of support for a lawsuit that the State of Washington had filed against the ban. Since then, Khosrowshahi has made his contempt for the President’s policies clear. In August, amid controversy over Trump’s response to violent protests in Charlottesville, Khosrowshahi wrote on Twitter, “I keep waiting for the moment when our Prez will rise to the expectations of his office and he fails, repeatedly.”
Khosrowshahi’s family led a prosperous upper-class life in Tehran until the Iranian Revolution threw the country into chaos. A wealthy uncle lived in New York, and the Khosrowshahis, after escaping temporarily to the South of France, where the family had vacationed in the past, immigrated to the United States and moved into a three-bedroom condominium in Tarrytown. Shortly after they arrived in the U.S., fifty-two American diplomats were taken hostage in Tehran, a crisis that lasted more than a year and created a surge of anti-Iranian sentiment in America. The family watched from across an ocean as their manufacturing business, which produced consumer and pharmaceutical goods under brands licensed from Western countries, was nationalized by the new Islamic government.
Khosrowshahi’s parents put their remaining resources into their children’s education, enrolling Khosrowshahi and his two brothers at Hackley, the prep school that their cousins attended. Khosrowshahi was in the fifth grade, and spoke less than perfect English. “It was a tough adjustment at first,” he told me. “But we knew how to play soccer. My brothers were total soccer gods within the school. And that was our in to being socially accepted.” Khosrowshahi was drawn to the sciences, and his father encouraged him to become a doctor. In Iran, Khosrowshahi explained, “the heroes of the world were the engineers or the doctors.” When he was in his early teens, his father returned to Iran to take care of his own father, who was ill. He was arrested by the government and detained for six years. Khosrowshahi’s mother, left to care for three teen-age boys, took a job as a salesperson at a high-end women’s-clothing boutique in Manhattan—the sort of store she had previously frequented as a client. “I think there was this undercurrent within my family, which was that we had lost everything,” Khosrowshahi told me. In his first address to Uber employees, in August, he put it more bluntly: “There’s this chip you have on your shoulder as an immigrant that drives you.”
Herb Allen III, the president of the investment bank Allen & Co., was a classmate of Khosrowshahi’s and used to join the family for dinners—warm, boisterous affairs that often ended with board games or charades. “They were the most family-oriented family I ever met,” Allen said. “It wasn’t just that you had to live up to your own potential. You were wearing the jersey of the whole family, and you were expected to behave in a certain way. You had to make the most of yourself.”
Khosrowshahi attended Brown University, where he studied bioelectrical engineering and immersed himself in Dungeons & Dragons, the role-playing game. “I was this odd combination of geek squad and at the same time hanging out with the jocks,” he said. He joined a fraternity of water-polo players and got so tired of hearing people mispronounce his name—“Dara What?”—that he began introducing himself as Darren K. “It sounds like a porn star, I know,” he said.
After graduating, Khosrowshahi took a job as a junior investment banker at Allen & Co., where one of his brothers was also working. At the end of Khosrowshahi’s first year, he received a twenty-thousand-dollar bonus and an all-expenses-paid African safari. Allen & Co. was known for its expertise in advising big media companies, and Khosrowshahi soon began working with Barry Diller, who was running QVC and attempting a hostile takeover of Paramount. The deal never went through, but Diller was impressed by Khosrowshahi and recruited him to work for IAC, Diller’s holding company. Seven years later, in 2005, Diller’s company Expedia was competing with a second generation of online travel businesses and looking for a new chief executive, and Diller asked Khosrowshahi to take the position. “He’s the quintessential example of someone who we immediately saw had talent—raw talent,” Diller told me. “We believe in throwing people into the water, and hopefully having them sink a little. And that process is a kind of window into their real character. He had no experience of any kind operating anything, and we threw him into that water. And he more than mastered the job.”
Expedia grew significantly while Khosrowshahi was running it, going from $2.1 billion in revenue in 2005 to $10.1 billion in 2017. (Its main competitor, Priceline, grew much more during the same period.) Khosrowshahi was well liked—the words “nice” and “wholesome” came up a lot in reference to him—and the company was regarded as a stable and satisfying place to work, with a high percentage of women and other underrepresented groups on staff.
In August, 2017, when Khosrowshahi called Diller to tell him that he was pursuing the Uber job, Diller tried to talk him out of it. Diller and his wife, Diane von Fürstenberg, were friends with Kalanick, and Diller knew that the situation at Uber was fraught. “I said, ‘Oh, my God, Dara, you must be out of your mind,’ ” Diller told me. “ ‘That’s a very dangerous place.’ ” In the end, he advised Khosrowshahi during the three weeks of negotiations.
On August 10th, Benchmark took the remarkable step of suing Kalanick, in effect cannibalizing its own investment. The lawsuit accused him of committing fraud to “entrench himself on Uber’s Board of Directors and increase his power over Uber for his own selfish ends,” and of secretly clearing the way for his return. The Uber board was divided into pro- and anti-Kalanick factions, and this split was reflected in the C.E.O. search. The search had converged on two candidates, Jeffrey Immelt, a former C.E.O. of General Electric, and Meg Whitman, the C.E.O. of Hewlett-Packard. Both were celebrity chief executives who had run sprawling corporations. Kalanick and his allies favored Immelt, who had expressed respect for tech-company founders and indicated that he would want Kalanick to remain deeply involved. The other group, led by Benchmark, was pushing for Whitman, with whom the venture-capital firm had a long relationship. There was no faction lobbying for Khosrowshahi. He told me that he saw his candidacy as “a bit of a lark—I was always the third, unknown candidate.”
One of the most pressing questions for the candidates was whether Kalanick would try to continue running Uber from the shadows. At the end of August, when Khosrowshahi gave a formal presentation before the Uber board in San Francisco, Kalanick was seated directly across from him. Khosrowshahi had made a set of PowerPoint slides, and, when he came to the slides addressingquestions of governance, the atmosphere grew tense. A slide about Kalanick read “There cannot be two C.E.O.s.” “I was very clear that we needed separation, that if I came in I’d need to be recognized as a leader. We’d have to push Travis away,” Khosrowshahi told me. “Travis is not active with the company at all anymore.” (At the end of March, Kalanick announced that he had bought the real-estate startup City Storage Systems and would join the company as C.E.O. He remains a member of Uber’s board.)
The following morning, Immelt inexplicably announced that he was dropping out. Suddenly, Khosrowshahi was a contender, if for no other reason than that the anti-Whitman votes needed a candidate. The board members gathered again, in a meeting room in the San Francisco Four Seasons Hotel, and began voting in a secret-ballot process that involved texting their decisions to a corporate headhunter. After the first round, the results were evenly split, with four votes for Whitman and four for Khosrowshahi. The voting dragged on through much of the day. Two of the board members were overseas, dialing in from remote time zones. The rest were stuck in a single room, like deadlocked jurors. Eventually, Benchmark said that it would be open to dropping its lawsuit against Kalanick if Whitman became C.E.O. Some of the board members reacted unfavorably to the pressure tactic and changed their votes. Huffington convinced the group that, whatever the results, it should announce a unanimous verdict for the winning candidate.
Khosrowshahi and Diller spoke several times as they waited for the results. Rumors had started to circulate that Whitman had been selected. Diller tried to console Khosrowshahi, and the two were on the phone when Diller received an e-mail. It was from Kara Swisher, the executive editor of the tech Web site Recode. The e-mail read “It’s Dara.” Diller asked Khosrowshahi, “Are you sure no one’s called you?”
Forty minutes later, Khosrowshahi was in his car on the way to buy groceries for dinner when he got a call from Huffington. “I have some good news and I have some bad news,” Huffington said. “Which do you want first?” Khosrowshahi told her he wanted the good news.
“The good news is, we picked you to be the next C.E.O. of Uber,” she said.
“What’s the bad news?” Khosrowshahi asked.
“It’s leaked already.”
n a rainy afternoon, I joined Khosrowshahi, his wife, Sydney Shapiro, and their five-year-old twin boys at their weekend home on Whidbey Island, forty-five minutes north of Seattle. (Khosrowshahi also has a teen-age daughter and son from a previous marriage.) The three-bedroom retreat, surrounded by giant fir trees and situated on twenty-three acres overlooking Puget Sound, is decorated in a style that Shapiro describes as “eighty-year-old grandma rock star,” filled with oil portraits and taxidermy and flickering candles. Uber board members have cited Khosrowshahi’s status as a family man as one element of his appeal, and a welcome contrast to Kalanick’s good-time-bachelor persona. Khosrowshahi has been commuting every week to San Francisco from the family’s primary home, in Seattle, and admits that it’s been a challenge. During an interview for CNBC in New Delhi, a young man asked him how he balances work and family, and he laughed. “Right now, work is winning, unfortunately,” he said. “My family is not that happy about it.”
As we sat down to a meal of roast chicken and vegetable soup at a long table in the kitchen—the boys ate pasta with butter—Shapiro told me that when they met, ten years ago, on a blind date, Khosrowshahi arrived wearing a suit and driving a rented Volvo. “I was, like, he’s the C.E.O. of Expedia, he’s going to be this arrogant, egocentric, just . . . douche,” Shapiro said. She had been working as a preschool teacher, and was wary of the fact that Khosrowshahi had just gone through a divorce. Shapiro, who is tall and graceful and wears ripped jeans and concert T-shirts, said that Khosrowshahi surprised her. “He had so many questions for me, and he was funny,” she said. She told me that, when the Uber job came up, she immediately knew Khosrowshahi was right for it, even though he was skeptical about his chances. She started looking at California real estate while he was still interviewing. She also encouraged him to dress in a more tech-friendly style, which today generally consists of jeans and a sweater.
“I wore a suit in Brazil,” Khosrowshahi acknowledged. He had recently visited the country, Uber’s second-largest market, to persuade Brazilian lawmakers not to pass legislation that would have imposed substantial new regulatory requirements. “I’ll wear one if we really have to apologize,” he said. Khosrowshahi has had to do a lot of apologizing since taking the job. Last September, he issued an open apology to the city of London, which had declined to renew the company’s license after finding it “unfit” to run a taxi service. In November, he apologized to the public after revealing that Uber hadn’t disclosed the 2016 hack, which had compromised the personal information of fifty-seven million riders and drivers.
One of Khosrowshahi’s first acts as C.E.O. was to create a new list of cultural values, which he developed by soliciting ideas from employees. (The endorsement of “toe-stepping,” he wrote on LinkedIn, was too often “used as an excuse for being an asshole.”) No. 4 now reads “We Do the Right Thing. Period.” He announced that in 2018 the company would focus on improving driver and rider safety. He’s hired experienced executives, including Barney Harford, the former C.E.O. of Orbitz, and Tony West, a former Justice Department official and chief legal officer of Pepsi.
Khosrowshahi is also trying to position Uber to go public, in part by making more careful decisions about which ideas to pursue. In late March, the company agreed to sell its business in Southeast Asia to Grab, a local competitor, in order to free up resources for Uber’s other divisions. The news was not welcomed in certain corners of the company, where employees worry that Khosrowshahi may lack the drive necessary to achieve Uber’s most ambitious goals. Khosrowshahi is set to make a hundred and twenty million dollars if he meets certain objectives, including taking the company public in 2019 at a valuation of a hundred and twenty billion dollars. One former employee, who expressed admiration for Khosrowshahi, told me, “If I’m Dara, my performance metrics are: Fix the board problems, fill out the executive ranks, bring liquidity to the investors by moving toward an I.P.O., and grow the company.” He continued, “Now, that’s a lot. But I think Travis’s mission was, like, let’s make this a five-hundred-billion-dollar company. Let’s invest in flying cars, let’s change how people eat, let’s change how people get around. They might sound the same, but those are very different things.”
A former Uber executive pointed out that, after eight years of existence, Facebook had killed off most other social networks and Google had built a near-monopoly in online searches. Uber, on the other hand, eight years after launching, “hasn’t won yet.” Under Kalanick, Uber sold its businesses in China and Russia. Many European countries, meanwhile, are seen as too hamstrung by regulations to be profitable. And Uber India, the former executive told me, “is in a dogfight with the local competitor.” That leaves Uber fully operational mainly in North and South America. “We’re in a highly competitive business,” he said. “It’s not time to change the culture to the point where people will start complaining about the snacks in the kitchen. It’s time to keep the aggression on.”
The fear that Silicon Valley companies will be overtaken by foreign competitors is part of a larger debate in the industry. In January, Michael Moritz, a partner at the venture firm Sequoia Capital, published a controversial editorial in the Financial Times, arguing that American businesses, in their eagerness to offer work-life balance, are at risk of losing out to Chinese tech firms, where “the pace of work is furious,” the offices are spartan, and “nobody complains about missing a Little League game or skipping a basketball outing with friends.” The Indian Minister of State for Civil Aviation made a similar argument to Khosrowshahi during a meeting in New Delhi, suggesting that Uber build an engineering center in India. Local engineers, he said, worked for less than engineers in San Francisco, and they wouldn’t complain about putting in long hours or demand on-site massages and organic food.
After the dinner on Whidbey Island, Khosrowshahi stacked the dishes in the sink while Shapiro took the boys upstairs for a bath. Then we wandered down the hall to a cozy library with a stuffed white peacock in the corner and a rosewood table where Khosrowshahi works on the weekends. He stretched out on a velvet sofa and talked about one of his most painful professional experiences—in 2008, after the financial crisis hit, he was forced to hold a town-hall meeting at Expedia to announce layoffs. “It was a really emotional moment for me, personally,” Khosrowshahi said, as the family’s cat, Moshe, gnawed on his foot. “Even though I was the one responsible for the firings, the company saw that it hurt.” He felt that showing vulnerability had made the process easier. “Management is about a contract, which is, you manage me because you’re higher up on the level and you pay me and do my review,” he said. “Leadership is about the heart.”
Like many technology companies, Uber has been sued by a group of female engineers claiming that they were paid less than their male counterparts. (On March 27th, the company agreed to settle the case.) At Expedia, Khosrowshahi made a point of hiring executives who “didn’t look like me,” and developed programs to increase the number of women. “I’m way too early at Uber to really start driving this,” he said. “But we’ll get to it.”
Silicon Valley has a reverent attitude toward founders, who still lead many of the industry’s largest businesses, including Amazon and Facebook. Simon Rothman, a partner at the venture firm Greylock Partners, told me that the culture of a company often reflects the personality of its founder. “Here’s an analogy: If you have parents, their DNA is in you,” he said. “If someone else raises you, you’ll be different, but you won’t be radically different. I think the longer a founder stays at a company, the longer it will take to change the culture at that company.”
According to the founder-as-culture theory, changing Uber is going to be a lot more complicated than simply switching out some of its slogans. When I asked Khosrowshahi about his impression of Uber’s culture before he took the job, he said, “I thought it was completely effed up. I was amazed at how one bad thing could come to light after another.” But, he added, the staff was eager to change. “I believe that, if you have a great product, a lot else can take care of itself,” he said.
Technology venture capitalists tend to fall into two groups: those who invested in Uber, and those who didn’t and are bitter about it. All are acutely aware of the cautionary tale of Apple, which pushed out its co-founder Steve Jobs in favor of John Sculley, a professional C.E.O. who ran it with little distinction until Jobs returned to rebuild the company. Many told me that somebody—a board member or an investor—should have taken a more active role in guiding Uber as it adjusted to the responsibilities of a large enterprise. One name came up often: that of Bill Gurley, the board member and Benchmark partner.
Gurley is six feet nine inches tall, and his outsized proportions contribute to his reputation as an eminent figure in Silicon Valley. He has a deep, bearish voice and a Texas accent, and he seems to collapse himself like a telescope when he comes through a doorway. (He testified in court recently in the Waymo suit against Uber, and the judge joked that he was the tallest witness who had ever been in the courtroom.) When I sat down with Gurley to talk about what had happened at Uber, he said, “The two questions my firm gets the most that relate to this subject are ‘I can’t believe you did this’ and ‘Why didn’t you do it sooner?’ ”
Gurley said that he spent months encouraging Kalanick to hire an experienced C.F.O. He likes to tell startup founders, “You’re not gonna win by having a more innovative finance program, you’re not gonna win by having a more innovative legal program, you’re not gonna win by reinventing H.R. They’re areas where experience carries a lot of weight.” Uber was weak in all three, and Kalanick never found his “Sheryl,” the grownup in the room exemplified by Sheryl Sandberg, whom Mark Zuckerberg brought in four years after starting Facebook. Gurley jumped up and started scribbling on a whiteboard to show the “cacophony of events” that led to the coup against Kalanick. Two other Silicon Valley success stories—the software company Zenefits and the blood-testing venture Theranos—had recently experienced public scandals and looked likely to go out of business, and, in the spring of 2017, Gurley became worried that Uber could meet a similar fate. Benchmark had invested twelve million dollars in Uber, and that stake had grown to be worth approximately $8.5 billion. It was a lot to potentially lose. Gurley also received an e-mail from the founder of another company he’d backed—Katrina Lake, of Stitch Fix, the online clothing retailer that recently had a successful I.P.O. Gurley recalled, “It basically said, ‘I really enjoy working with you, but I can’t stand the fact that you’re associated with that guy.’ ”
Gurley told me that Silicon Valley investors, even ostensibly powerful ones, can no longer rein in the young, mostly male tech founders, who often have voting control over their companies. “Venture capitalists that serve on boards have gotten more and more deferential and, I would say, have become more cheerleaders than actors,” he said. He attributed the change to “a phenomenon that was absent from the rest of recorded history: access to unlimited capital.” Benchmark’s competitors had been using its role in the coup to criticize the firm to other startup founders. “ ‘You don’t want to take their money, look what they did to the founder of Uber,’ ” Gurley said. “I bet that conversation has happened a hundred times.” Although Kalanick’s ouster had created “a lot of broken glass,” Gurley didn’t regret it. “I’m confident that history will look kindly upon what we did,” he said.
Every day, Uber interacts with millions of customers and millions of drivers, and a visit to the company’s thirty-thousand-square-foot driver center in Queens gives a sense of how byzantine the logistics of these interactions are. Hundreds of people, many of them immigrants, arrive each morning to register to drive for Uber. They take out auto loans, sign up for medical exams, and get help with New York’s onerous licensing system. The street outside is clogged with black cars double- and triple-parked, and a Doughnut Plant on the ground floor advertises a chai-and-samosa-doughnut special for eight dollars.
Uber has been criticized for taking advantage of its drivers, who work without job security or benefits, and whose commissions the company has reduced more than once. Shortly before Kalanick’s departure, Uber realized that this was a strategic mistake—the company needed to attract drivers, rather than repel them, if it wanted to continue to grow. Many riders, meanwhile, felt increasingly uncomfortable using the app, which had come to symbolize gig-economy exploitation. Courting drivers is now a priority at the company, which refers to them as “driver partners.”
During his trip to India, where drivers have periodically gone on strike for days to protest falling wages, Khosrowshahi met with a small group of drivers to solicit feedback. Several complained that Uber’s maps of Delhi failed to reflect the spontaneous detours that spring up on local roads. A portly driver in a white dress shirt suggested that the company offer a voice-only interface, sincemany people in India can’t read or write. Finally, a driver said, “For partners who’ve spent a long time with Uber, is there a way to help them save money and plan for old age? Some way we can be incentivized for being the longest-term drivers, just like you have for employees?” Khosrowshahi nodded in agreement. “This is a theme not just in India but everywhere in the world,” he replied. “We’ve been thinking too short-term.”
In fact, Uber’s long-term plan is one in which drivers, with their costs and complications, will have a diminished role. The company has been running autonomous-vehicle pilot programs in four cities and also testing driverless long-haul trucks. Several companies, including Google and General Motors, are racing to develop their own autonomous-driving technology. Uber’s program, the Advanced Technologies Group, which began in 2015, was one of the first to launch, and this year its vehicles reached a milestone of three million miles driven autonomously. The division now has more than fifteen hundred employees, most of whom work in a former factory on the waterfront in downtown Pittsburgh. The space was lavishly retrofitted with an eighty-foot glass wall, reclaimed-wood tables, ceiling-mounted fireplaces, and seventy kinds of modernist chairs. Each room has a name drawn from Formula One racing.
To Kalanick, the autonomous-driving unit was the jewel of the company. When Khosrowshahi took over, he considered closing the program, since it could potentially cost billions of dollars. He decided not to close it after talking to Eric Meyhofer, the head of the division. “If you walk around here—this isn’t five people in a garage building some little robot car,” Meyhofer, who co-founded Carnegie Robotics, at Carnegie Mellon, before joining Uber, told me. “This is all about building autonomous ride-sharing, at scale, as a product. This is our future.” The question now, Meyhofer said, isn’t whether the company can make a self-driving vehicle but whether it can make one quickly and cheaply enough to solve Uber’s revenue problems.
On a damp, unseasonably warm day in January, I climbed into the back of a Volvo XC 90 at the Advanced Technologies Group headquarters. The vehicle was one of Volvo’s luxury models, with supple leather interiors. It was equipped with a ninety-thousand-dollar lidar unit on the roof, sixty-four lasers, eight cameras, and a stack of liquid-cooled computer hard drives in the trunk, which emitted a gentle hum. My autonomous-vehicle operator, who raced motorcycles in his spare time and spoke with the calm, even tones of a kindergarten teacher, told me, “Once you see what the car can do, you’ll be absolutely amazed.” His job was to sit with his hands hovering under the steering wheel, ready to take control if anything went wrong. “You’re driving the car in your mind,” he said. “You’re just not using your hands.” He and the other operators had been tested on a racetrack to see if they could handle emergency maneuvers, such as making a sharp turn at sixty miles an hour.
He summoned a route on a dashboard iPad—the cars drive on preprogrammed maps, effectively following virtual tracks like trains—and pushed a silver button on the dashboard to snap the car into autonomous mode. The vehicle took over, moving smoothly forward. “Now I literally have to do nothing,” the operator commented while waiting to turn at a red light. “But, if this idiot here decides to pull out in front of us, then I may take over.” There was a white Toyota in the opposing lane, and, sure enough, it jumped forward to make a left turn in front of us just as the light turned green. “That’s what’s called a Pittsburgh Left,” the operator said. He explained that the car collected information about every aspect of the ride and sent the data back to Uber’s engineers. “Let’s say we got into an accident. We would have complete video evidence of everything,” he said. “The car doesn’t get tired, it doesn’t get angry, it doesn’t drink . . . it’s just always going to do the right thing.”
Each time a pedestrian appeared in front of us, he or she showed up in blue on the iPad, which reflected what the car was “seeing.” The vehicle could monitor hundreds of pedestrians at a time, the operator said, and had been programmed to be extra cautious around them. As we moved through Pittsburgh’s construction-filled streets, however, the operator jumped in with surprising frequency, taking over when a person in a parked car unexpectedly opened a door, or when passing through school safety zones, where the vehicle automatically slowed to fifteen miles an hour. The operator told me that the car sometimes got into awkward situations, such as when other drivers motioned for it to go ahead, and the car couldn’t pick up on the signal. At one point, a node in the trunk’s hardware stack crashed, and we had to pull over to reboot. Such occurrences, my operator assured me, were rare.
On March 19th, Uber’s entire self-driving pilot program was put on hold after a test vehicle in Tempe, Arizona, killed a forty-nine-year-old woman named Elaine Herzberg. The next day, Arizona police released a video of the collision. The eerie nighttime footage showed the car gliding into Herzberg at around forty miles an hour as she walked across the street with her bike. The vehicle operator, who was visible in part of the video, glanced down for a few seconds, possibly at the dashboard iPad, and then looked up too late. The operator’s face twisted into an expression of shock. When I reached Khosrowshahi by phone shortly afterward, he seemed disheartened, and disarmed by the intense scrutiny that comes with his new job. He told me that the autonomous division had been working toward offering driverless-car service by the end of the year, and that there would inevitably be “bumps and bruises” along the way. “What happened last week was truly tragic,” he said. “We’ve clearly taken a very, very big step back.” He is closely reëxamining Uber’s work in autonomous vehicles.
While I was in Pittsburgh, Meyhofer told me that, like other parts of Uber, the autonomous-vehicle group was under immense pressure. Getting to the technology early was a matter of survival for the business, he said—something that Kalanick, in his obsession with rivalries and short-term results, understood intuitively. Even though a lot had changed, the pressure was still there, in part because so much had been invested already. “The problem is, if someone builds this technology and puts it on a ride-sharing network, their cost competitiveness will be stronger than ours. And if someone else does that, and we don’t have it, how long can we survive?” Meyhofer said. “So you’re racing this ghost. And no matter what you do it’s not enough. Dara doesn’t impose pressure like that, but he doesn’t need to. It’s the reality of the business we’re in.”
~this story will be in the April 9th issue of The New Yorker