In early March, Travis Kalanick, the 40-year-old CEO of Uber, was riding in an SUV to Palo Alto for the company’s Technology Day, thinking about how to help Uber survive one of the worst periods a corporation had ever experienced. In January, some 500,000 users had joined a campaign to #DeleteUber from their phones, in response to the company’s perceived lack of support for protests at JFK against the Trump administration’s immigration ban (Kalanick had recently joined Trump’s economic council), which seemed to underscore the long-standing view that Uber didn’t care much for its drivers. The deletions were still coming three weeks later when Susan Fowler, a female engineer who’d left the company, accused it of rampant sexism and sexual harassment. Then, over the next two weeks, Google sued Uber, alleging it had stolen the company’s self-driving-car technology; a video surfaced of Kalanick getting into a profane argument with a driver; and the New York Times revealed that Uber had moved into cities where it was not allowed to operate with the help of a tool called Greyball. (The program showed government officials a fake version of Uber’s app with “ghost cars” so its drivers couldn’t be apprehended.)
When Kalanick got to Palo Alto, he told the assembled engineers that, seven years after the app launched, it was time for “Uber Version 2.0.” Just as Kalanick’s ambition was no longer to become “Everyone’s Private Driver,” as an early slogan suggested, but to change the way people and things move around the world, he said that Uber would become not simply a better place to work but “the most just place to work in the world.” In a blue V-neck sweater over a white undershirt, Kalanick cited Harriet Tubman, Gandhi, and Martin Luther King Jr. as inspirations, said he had spoken to Sheryl Sandberg about unconscious bias, and joked that he hoped to find a way to quantify justice — he just needed to figure out the unit of measurement.
Coming from Kalanick, who is described by even his supporters as an “asshole,” the talk sounded forced (“I talk a lot about justice — I’m just about it”), especially when he put up a photograph on a projector screen of the Fearless Girl statue that had recently been installed in downtown Manhattan, across from the Wall Street bull. “When I saw it, I was inspired,” Kalanick said. He wanted Uber’s employees, especially its women, to “be that fierce girl standing up to the bull,” while adding that he intended to make Uber a place that “doesn’t have bulls all over the freaking place.” He sat back as the crowd applauded.
In its brief history, Uber has morphed from a simple service that allowed users to press a button to summon a car into what is on paper the most valuable start-up of all time. It also spawned an entire category of start-up pitch — Uber, but for doctors, for cookies, for private jets — bent on solving First World problems via app. Uber has created vast theoretical fortunes and helped remake the American economy. Its most recent valuation, of $68 billion in 2015, was the highest ever given to a private company. Silicon Valley’s obsession with “unicorns” — companies valued north of a billion dollars — was very 2012. We had entered the era of the “decacorn.”
Uber itself, however, has lately become a monument not only to the power of technology and confidence in the face of adversarial forces but possibly to the dangers of hubris: When you’re worth that much money on imaginary paper, and buoyed by the belief that you’re on a mission to change the world, it can be easy to sweep aside concerns like “rampant sexual harassment” and “public relations” and “profits.” In the past, Kalanick has said that, on bad days, he found comfort by looking at the company’s revenue graph, which continues to go up and up, even through Uber’s tumultuous 2017. And yet Uber lost at least $2 billion in 2015, a shocking deficit it followed last year with a loss of $2.8 billion — a number that didn’t even include its star-crossed attempt to break into the Chinese market. Much of those losses had come in the form of subsidies: Uber was paying bonuses to drivers to get them on the road and keep them there, while subsidizing rides for users by charging well below the true cost. The idea was to get people so addicted to the Ubering lifestyle that the app would be baked into their lives, to such a degree that no one would much care if and when the subsidies went away and the price went up. Or Uber would simply drown its competitors in cash until the advent of autonomous cars got rid of its biggest cost: drivers.
But should any business have to work as hard, ignore as many laws, and spend as much money as Uber has simply to become a viable business? Conversations with several dozen current and former Uber employees and executives suggested that though there is time to right the ship, and a war chest of venture capital to do so, Silicon Valley has found itself at least preparing for the notion that it mispriced its darling. Uber could be the next MySpace, some say, a company that created a market but was foiled by its own missteps and overtaken by savvier competition. Or the recent PR disasters could be more than just flesh wounds, and instead reveal an aggressiveness that has both created and masked a deeply flawed business model. Either way, a report in April said private Uber shares were trading at a discount.
Earlier this month, while I was riding an elevator up to Uber’s headquarters in downtown San Francisco, a short young woman in a floral-printed dress asked me if I was interviewing for a job, too. As we signed nondisclosure agreements on iPads in the company’s lobby, she said that she had applied for a job as a project manager months ago, but Uber’s series of unfortunate events had led her to put off entreaties from the company’s recruiters. Eventually, she relented and decided she might as well see what it’s like on the inside. “There’s a lot of smart people here,” she said. “So it might not be that bad, right?”
To anyone paying attention, many of the recent problems at the company weren’t entirely shocking. Uber’s workplace had long been considered one of tech’s toughest, it had always flouted governments and regulators — the company’s first cease-and-desist order hangs on a wall at headquarters — and it often seemed to treat drivers with disregard, opposing unionization efforts and denying employee benefits to full-time drivers, who are responsible for about half of the company’s trips. Its reputation was burnished, however, by a cohort of former political operatives, led by David Plouffe, once President Obama’s campaign manager, who successfully lobbied state and local regulators, arguing that the company didn’t just put more fossil-fuel-burning cars on the road; it represented the future of work, offered part-time postrecession employment to those who needed it most, and cut down on DUIs (and would eventually reduce the number of cars on the road, if people were to give up their own cars in favor of ride-sharing). But the real trick was offering a product with undeniable appeal, particularly to young urbanites, which helped reinforce the company’s sense of inevitability. “Uber riders are the most affluent, influential people in their cities,” Kalanick once said. “When we get to a critical mass, it becomes impossible to shut us down.” David Weil, a former Labor Department official tasked with helping to judge whether ride-hailing drivers should be considered full-time employees or independent contractors, told me he had been surprised by the uniformity of support for the company in meetings with young Capitol Hill staffers. “The first question I’d be asked was, ‘Well, what have we got against Uber?’ ” Weil said.
The uproar over Uber’s response to the protests at JFK in January was thus something of a dramatic correction in how the company was perceived. Shortly after New York’s taxi-drivers association announced a strike in support of the protests, Uber tweeted that it would not be turning on surge pricing. The intention was to avoid taking advantage of a delicate situation, as the company had been accused of doing by up-charging users during hurricanes and blizzards, but thanks to the tinderbox quality of the political moment, it was perceived as an attempt to break the strike. “It was 100 percent in the spirit of helpfulness,” one former executive told me. “And it became the poster child for why reputation matters.” Kalanick’s role on President Trump’s economic advisory council only made matters worse, and some at the company suggested that he should attend the council’s upcoming meeting, demand that Trump rescind the ban, and, when he refused, get up and walk out — a plan that was ultimately deemed too brash even for Kalanick, who simply resigned his position.
The company’s image suddenly posed a threat to the bottom line, at a moment when it wasn’t difficult for many users to delete Uber and download Lyft — nevermind that two of Lyft’s biggest investors included Peter Thiel and Carl Icahn, both prominent Trump supporters — without noticing much of a difference. After Bloomberg published a video in which Kalanick ended an argument with an Uber driver who felt the company had unfairly lowered its rates after he leased a new car by saying, “Some people don’t like to take responsibility for their own shit,” an MLB team backed out of a partnership with the company, according to an Uber manager with knowledge of the deal. “Uber used to have this sex appeal,” the manager said. “People would pay to work with us.”
The video had also connected Kalanick to the worst parts of the company’s reputation. In addition to his penchant for working well past midnight and demanding the same of his employees — known internally as “Uberettos” — Kalanick had also displayed the kind of immaturity more associated with Silicon Valley’s barely legal founders. “We call that Boob-er,” he told GQ in 2014, when he was 37, of how Uber had helped his dating life. One executive said that several times in the past year, including in February, when the company was in turmoil, Kalanick had been unreachable in the morning. “We were trying to find him and get him to approve something, but he’d been out late, apparently, and the answer was ‘He’s not up yet,’ ” the executive said.
The company’s rapid growth — it went from 600 employees in 2014 to more than 12,000 today — meant that almost two-thirds of its managers were in positions of authority for the first time, which led to a variety of organizational issues. Kalanick, for one, insisted on being kept aware of anything going on at the company, and had a habit of inserting himself into other people’s jobs: Four different Uber employees told me they had at times found themselves writing something in a Google Doc, only to suddenly realize Kalanick was editing the document at the same time. “He would go in there all the time and say, ‘Stop typing,’ and I’m like, ‘I’m editing your shitty grammar,’ ” one said.
In 2014, Kalanick unveiled a list of 14 company values at a Las Vegas retreat that included “toe-stepping,” “always be hustlin’,” and “super pumped.” There was also “principled confrontation,” which one former manager said was “the one people used as an excuse to just be assholes.” The manager, who recently left Uber, said that he had conducted a survey of his subordinates at his new company, and they had complained that he was “really aggressive,” which he thought was accurate. At Uber, however, “people were telling me I wasn’t aggressive enough.” Several engineers — one who had worked on designing a system to enable users to delete their ride history, “for if you took an Uber to your mistress, basically” — told me that managers sometimes demanded that employees work through holidays and weekends and that they often worked as much as 100 hours a week.
Now the company’s relentless culture, to which many credited its growth, was unraveling, especially after Susan Fowler published her blog post in February detailing blatant sexual harassment and sexism at the company and a lack of responsiveness from the human-resources department. “I’ve rarely seen an organization just so viscerally hit by something that was coming in from outside,” Liane Hornsey, the company’s new head of HR, told me in reference to the reaction to Fowler’s blog post. We were in a conference room on the 15th floor of Uber’s headquarters, where recruiters sit among putting greens that dot the floor. (Uber declined to make Kalanick available for an interview.) To turn around morale, Hornsey and various deputies had conducted 200 listening sessions in recent months and committed to a variety of changes: a promise of equal pay; tweaking the corporate values to give a nod to teamwork.
Still, Uber had continued to lose employees. In March, Jeff Jones, a well-regarded marketing executive who had been brought in to serve as a sort of Sheryl Sandberg figure to Kalanick’s Mark Zuckerberg, left after just seven months, declaring in a statement that “the beliefs and approach to leadership that have guided my career are inconsistent with what I saw and experienced at Uber.” Others who had previously chugged the company Kool-Aid had come to believe Uber would never change. “I’ve never been at a place where it was so clear that people don’t matter — that nothing matters — so long as we can make an extra two cents a trip,” said a manager who left the company in March. “Uber is the most capitalist company on the face of the earth. It’s just the concept of supply and demand embodied.”
And yet, those massive subsidies, so crucial to Uber’s growth, don’t exactly sound like a pure version of capitalism, a problem that is beginning to dawn on observers both inside and outside the building. But there are still true believers in Uber’s promise: Among the former and current employees I spoke to, the most optimistic were its engineers. “This business model and technology is absolutely necessary for the world,” Brian McClendon, the company’s former head of mapping, told me one day in April over barbecue in Kansas City. McClendon had left Uber a few weeks earlier, to lend his 30 years of Silicon Valley experience to politics in his native Kansas. While Uber says it has become profitable in some large cities, where the system is wired into the lives of young users in particular, McClendon admitted that he had not given up his car while living in Silicon Valley, and said that Kansas City was “the least Uber-friendly city in the country,” because it has more highway miles than any other major city. One former Uber manager who oversaw growth in a number of smaller, non-coastal cities where the cost of owning a car is low told me that the business there was almost exclusively taking people to and from bars.
But McClendon argued that for people in urban areas, the cost of Ubering was beginning to make as much financial sense as owning a car, especially if riders were willing to use Uber Pool, a service that matches riders traveling to and from similar locations to share a car and split the cost. Uber says that Pool now makes up a quarter of all rides in New York, and it hopes that Pool will one day become a majority of its business, which is the most winning argument for not only its alleged environmentalism and corporate citizenship — a study by transit expert Bruce Schaller found that Uber and other ride-hailing services accounted for 600 million miles driven in New York City alone last year, likely contributing to the city’s congestion and pollution and sapping resources from public transit — but also its ultimate profitability. If Uber can put more people into a car and pay only one driver, margins go up. Ronak Trivedi, a product manager for Uber Pool, told me the company had devoted “our best data scientists” to figuring out how to make Pool a more convenient service for both drivers and riders. He said Uber had recently started getting feedback from drivers on the product, which it considered a novel idea, but according to Uber the secret to solving carpooling — which Americans have never widely adopted, even in times of high oil prices and public campaigns encouraging the practice — was still in the algorithm.
But more than any technical advantage, the key to Uber’s growth has been its $15 billion of venture-capital funding. The company has long acknowledged that most of its losses come from subsidizing rides. (The most progressive argument for using Uber may be the fact that it has been a considerable redistribution of wealth from investors to working-class drivers.) But even close observers were surprised last November when a transportation-industry analyst named Hubert Horan published an examination on Naked Capitalism of the limited financial information Uber had made public and determined that it was covering around 60 percent of the cost of each Uber ride. Horan’s article expanded into a nine-part series that went as viral as 39,000 words with 89 footnotes on transit economics can. The 60 percent number was widely cited in various prominent outlets, and Uber has never contested Horan’s math.
More worrying to Horan than the losses themselves, which any growing company has to endure, was the fact that it didn’t seem Uber had brought significant efficiencies that would lower the cost of driving people from point A to point B, a difficult business with thin margins. Hailing a car with an app had been a magical experience when it was first released, but to Horan, it hadn’t changed the economics much more than the Domino’s app for ordering a large pepperoni. “You go through this checklist of stuff and the old bullshit meter goes into overdrive,” Horan told me. “They haven’t done anything to solve any underlying problems. It’s all people who have this quasi-religious belief that technology will solve every problem known since the dawn of time.”
To explain its massive losses, Uber and its investors have often cited Amazon, which didn’t turn a year-end profit for ten years as it built out an infrastructure that made the selling of more and more books — and eventually, of everything — cheaper and more efficient the larger it got. But Amazon’s biggest-ever loss was $1.4 billion, half of Uber’s 2016 deficit, and Jeff Bezos responded by cutting 15 percent of his workforce. Plus, Uber’s economics barely resemble Amazon’s. The taxi business doesn’t scale in the same way, and while Uber’s technology is sophisticated, the barriers to entry are relatively low, and Uber has had to fend off various competitors. So far as Horan could tell, there was only one possible path for Uber to meet that $68 billion valuation: eliminate competition.
Uber’s potential aspirations toward monopoly are a sensitive matter — in discussing how Uber Pool became more efficient the more people used it, McClendon referred to Uber’s ideal state as a “monopoly,” before correcting himself to call it “not a monopoly, but a heavily used service” — and while every company dreams of owning its entire market, the question of whether Uber can do so has become murky. One Uber investor told me he no longer sees ride-hailing as winner-take-all but didn’t want to speak for the company; when I put the question to Rachel Holt, Uber’s head of North American operations, she ducked it by praising the value of competition and saying she didn’t have a crystal ball.
Recent events have made a monopoly harder to imagine, to say nothing of how regulators might react. While Uber said its business in the United States was briefly profitable early last year, the company had been forced back into the red by Lyft, which had secured a new round of venture funding and begun offering more subsidies of its own to attract drivers and riders. Uber’s woeful early 2017 had also helped Lyft, which saw ridership increase 137 percent compared to the year prior. And while so far Lyft remains content to focus on the U.S., Uber’s ambitions for a global reach have added further costs. It is now in 75 countries, and faces an array of regional and local operators in each market. Its most formidable rival may actually be Didi Chuxing, a Chinese company that has already clocked more rides than Uber and recently raised $5.5 billion to help it compete in new markets. Uber spent two years, and $2 billion, trying to break into the Chinese market but eventually called a truce last year and agreed to sell its Chinese business to Didi in exchange for a stake in the company.
Meanwhile, in an effort to show potential investors in an IPO that it has multiple revenue streams, Uber has expanded into a variety of industries tangentially related to its core business. In 2015, the company launched Uber Everything, an initiative to figure out how it could move things in addition to people, and when I visited Uber headquarters, the guest Wi-Fi password was a reference to Uber Freight, the company’s attempt to get into trucking. (A former employee said the password often seemed to be a subliminal message encouraging employees to focus on the company’s newest initiatives.) But moving things had its own complications. One former Uber Everything manager said the company had looked at transporting flowers or prescription drugs or laundry but found that the demographic of people who, for example, couldn’t afford a washer and dryer but would pay to have their laundry delivered was a small one. Uber Rush, a delivery service in New York, had become “a nice little business,” the manager said, “but at Uber, you’re looking for a billion-dollar business, not a nice little business.”
It turned out that food delivery was the only area that made much sense, though even that was difficult. In the past year, food-delivery companies SpoonRocket, TinyOwl, Take Eat Easy, and Maple have all ceased operations. Postmates said in 2015 that it could be profitable in 2016, at which point it pushed the date to 2017. Its target is now 2018. “It absolutely does not work as a one-to-one business — picking up a burrito from Chipotle and delivering it,” a former Uber Eats manager said. “It has to be ‘I’m picking up ten orders from Chipotle, and I’m picking up this person next to Chipotle, and I’m gonna drop the burritos off along the way.’ ” Uber Eats has grown significantly, but getting the business up and running had required considerable subsidies, and the manager said it was rumored that a significant portion of the company’s domestic losses were coming from Uber Everything.
Uber’s expansion into an ever-widening gyre of business interests makes sense for a company looking to justify a huge valuation, but it has drawn criticism from some who wonder why the company is moving into so many different markets without becoming profitable in its first one. “It’s a Ponzi scheme of ambition,” Anand Sanwal, a venture-capital analyst, told me. “ ‘We’re gonna raise money on the promise of dominating an industry to come in order to pay for this thing that doesn’t make us money right now.’ ” He had recently conducted an unscientific poll of subscribers to his newsletter asking how many would invest in Uber today, even at a discounted valuation, and 77 percent said they wouldn’t. But the new initiatives have the benefit of keeping everyone excited about the future: In April, Uber held a conference in Dallas to explain why it planned to one day get into flying cars.
Back on land, Kalanick had already discovered perhaps his company’s biggest opportunity and gravest threat: self-driving cars. On the one hand, getting rid of “the other dude in the car,” as Kalanick once callously referred to the drivers on whose backs he built the company, would cut out Uber’s biggest costs. On the other, he realized the technology was “basically existential for us”: If Google, or another tech company, or an automaker, developed a driverless car, there was no guarantee they would offer the cars to Uber’s network rather than develop their own. The company launched its effort to build a self-driving car in February 2015, poaching 40 robotics researchers from Carnegie Mellon University with six-figure bonuses, and set up a research facility in Pittsburgh, but by that point it was already behind. To jump-start Uber’s research, Kalanick began courting Anthony Levandowski, a star engineer from Google’s self-driving program, in whom he found a kindred spirit: While Kalanick had broken up with his girlfriend to work at Uber full time, noting that “I should probably find someone I like at least as much as my job,” Levandowski had once worried that a member of his team wasn’t focusing enough on his work and offered the man’s girlfriend $5,000 to break up with him until the end of the project. (She didn’t; the couple got married.)
Levandowski left Google in January 2016 to work on his own self-driving project, but soon began showing up at Uber’s self-driving facility, where one engineer said Kalanick told everyone to give him a “complete brain dump of everything we’ve done to date.” Levandowski began consulting for the company, and a former Uber engineer said he attended meetings during which Levandowski strategized with Uber on how it could recruit Google engineers. The engineer said he was asked to delete messages discussing any possible collaboration. In August, Uber paid $680 million to acquire Otto, Levandowski’s start-up, and put him in charge of its self-driving program.
Soon after, in Pittsburgh, Uber scored a PR coup by becoming the first U.S. company to pick up a passenger in a self-driving car, with a safety driver there just in case. (While the company does not offer drivers employee status or benefits, a recent job posting for an “Uber Autonomous Vehicle Operator” offered a 401(k) plan, medical coverage, and a steady salary of $20 an hour.) According to one engineer, Levandowski suggested that Uber quickly prepare for a splashy self-driving launch in San Francisco by December. “He said it would be a big bang and a massive fuck-you to all our competitors,” the engineer said.
It turned out to be a disaster. On the first day, one of Uber’s cars ran a red light in front of the Museum of Modern Art. “The San Francisco car was a piece of shit,” the engineer said. “The problem with Anthony is he’s super-focused on building a cool demo, but building a cool demo is contradictory to building good technology.” Several engineers left Uber, many to start their own self-driving competitors, upset by a feeling that Levandowski was pushing the technology too fast in order to close the gap with Uber’s competitors. The company had launched the test without approval from California regulators and was told to cease operations; in Pittsburgh, which had warmly welcomed Uber’s self-driving effort, the company became a political football in the city’s mayoral election as various candidates criticized the company as a bad corporate citizen. Last summer, after a man died in a Tesla that was using the car’s Autopilot system, which allows for autonomous driving on highways, Levandowski told several Uber engineers that they were not pushing aggressively enough. “I’m pissed we didn’t have the first death,” Levandowski said, according to a person familiar with the conversation. (Levandowski denies saying this.)
Uber’s problems got even worse in February, when Google’s driverless program, now called Waymo, filed a lawsuit alleging that Levandowski had stolen files from Google and that Uber had used them in the design of its self-driving car. Shortly before leaving the company, Levandowski had allegedly plugged an external hard drive into a company laptop for eight hours and downloaded 14,000 files. (Levandowski said he needed the files to work from home.)
In court, Google argued Otto had been a front and that Levandowski and Uber had conspired for him to join the company all along. In May, a federal judge issued a partial injunction barring Levandowski from working on the technology in question, clearing the way for a public trial in the fall. The judge also took the unusual step of referring part of the case to the U.S. Attorney for possible criminal prosecution. If Uber is found to have knowingly stolen trade secrets, various executives, including Kalanick, could face criminal charges, and Levandowski, who remains employed at Uber, has already invoked his Fifth Amendment rights, citing the possibility that he could be charged. In the course of a five-hour deposition by Google’s lawyers, he repeated the sentence “On the advice and direction of my counsel, I respectfully decline to answer” 393 times.
Regardless of the case’s outcome, it has hampered Uber’s self-driving efforts at a time when they can scarcely afford to be stalled: Experts predict that self-driving cars will begin picking up passengers without safety drivers in small, geo-fenced areas in the next five years. “We were seven years behind Google when I started,” one former engineer said of the company’s driverless technology. “When I left, I think we closed the gap to five years.” During one week in March, Uber’s cars had to be taken over by human drivers every .8 miles, according to internal documents obtained by Recode. Waymo’s cars, by comparison, drove more than 600,000 miles in 2016 and required human intervention only 124 times. According to one recent report, Uber was just the 16th-most-likely company to develop a driverless car, behind not only Waymo and Tesla but also Ford, General Motors, and other traditional auto manufacturers. In April, Waymo deployed a fleet of driverless cars in Phoenix, with a test group of residents able to order a car at any time through its own proprietary app. “I always thought the biggest threat to Uber was if Google bought Lyft,” one engineer told me in May. A few days later, Waymo announced a partnership with Lyft.
Does all that mean Uber — so synonymous with this tech boom, and with the modern city itself — is going to become a relic of this decade? Will it be an app that you delete less out of protest than simply because your phone gets too crowded? “I don’t think it’s doomed,” Erik Gordon, a business professor at the University of Michigan, told me recently. “But I think it’s stunted. It was within an arm’s length of absolute dominance — of being Microsoft in Microsoft’s best days — but I think it’s going to be a case study we teach in business school of a company that could have crushed all comers but because of their repeated botch-ups, they aren’t in that position and will not be in that position.” The botch-ups have continued. On May 24, Uber announced that it had incorrectly calculated payments to drivers in New York City, to the tune of $45 million — the company quickly apologized and gave individual drivers back pay of as much as $7,000 — an embarrassing admission for a company that proclaimed itself to be built on data. The error came in the wake of a lawsuit brought by a drivers-advocacy group alleging that Uber had engaged in wage theft — one of countless legal issues the company faces, or may face in the future. The European Union’s top court is currently considering whether Uber should be regulated as a traditional taxi service; its classification of drivers as non-employees is likely to undergo further scrutiny; and it faces a Department of Justice investigation into Greyball.
A report on the company’s culture, stemming from Susan Fowler’s blog post and conducted by former attorney general Eric Holder’s law firm, is expected to be released soon, but it’s unclear what will change. Uber’s appointment of Arianna Huffington, a board member, to oversee the report has proved controversial. Huffington considers herself a “close friend” of Kalanick’s and has said in interviews that sexism is not a “systemic problem” at Uber and that she did not expect Kalanick’s resignation to be on the table. “She blew the independence of the investigation from the beginning,” one former executive said. Kalanick is trying to hire a COO to be his No. 2, but some have argued Uber might be better off with a new No. 1. That scenario would likely require Kalanick to step down, given that the makeup of votes on the company’s board is weighted heavily in his favor. According to the tech site the Information, Kalanick recently told an ex-girlfriend that while some of the company’s employees might want him to leave, the majority wanted him to stick around — and he felt an obligation to do so, for the employees’ own well-being. “You’ll know when you’re a mother,” she said he told her.
“So rarely do we stop and give Darth Vader credit,” Chris Messina, a former Uber developer who left the company in January, told me over coffee around the corner from Uber’s San Francisco office. Messina, who previously spent three years at Google and is credited with inventing the hashtag, said that in his view, Kalanick had built a remarkably complex company through smarts and sheer force of will, and that if he had cut a few corners, that was merely the price of progress. If there is good news for Uber, it is the fact that despite its losses, more and more people continue to use its service, and it still claims to have a shocking $7 billion to spend. Messina had heard from people still at the company that Kalanick had been cowed and that the organization was committed to changing, but he suspected that in the end, Uber could only be Uber. “The people there now, it’s like the Spartans in 300,” Messina said. “Everybody’s got their backs to each other, spears out, and they’re yelling, ‘Fuck the world, man. They don’t get it.’ ”
*This article appears in the May 29, 2017, issue of New York Magazine.