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The Smartest Bro in the Room

Ellen Cushing | November 18, 2014 | Story Tech World National

Travis Kalanick is trying really hard to sit still. You can tell by the way that he clasps and unclasps his hands under the table, and by the unnervingly intense eye contact that he makes as he speaks. Despite the sophisticated setting—a wood-paneled conference room in the mid-Market headquarters of the company he founded, the international ridesharing behemoth Uber—conversing with Kalanick is a bit like talking to a restless child as he poses for a school picture.

Uber’s head of PR, who sits in on our interview, had warned me that Kalanick “gets up and paces around a lot,” but during our hour together, the CEO suppresses the urge. He remains seated. His talking points are well honed, his cadence slow and deliberate, his demeanor completely inoffensive: polite, thoughtful, friendly even. He drinks ice water infused with watermelon and plum. He smiles a lot. In a rumpled purple sweater and normcore jeans, Kalanick, 38, is dressed not like the slick cutthroat capitalist that many claim him to be, but like a dad, and not a particularly cool one at that. He tells me that his Uber passenger rating, which all company customers receive from their drivers, is a just-shy-of-perfect 4.9. (“I was at a 5 for a long time, then I had a string of 4 stars. I don’t know what happened. I think what happened was I was a little stressed at work. I was not as courteous as I should have been.”)

It’s hard to reconcile this version of Kalanick with the man who gleefully Instagrams cease-and-desist letters from taxicab companies; who is repeatedly, and not necessarily unkindly, described by friends and colleagues as “douchey”; who wisecracks to GQ that he can score women as easily as he can call a car (“yeah, we call that Boob-er”); who has been widely characterized as petulant and prickly and quick to confrontation (“‘Loose cannon’ is accurate,” one associate tells me); who has gained a reputation for bottomless coffers, ceaseless ambition, and a willingness to do anything to win.

No, this Travis is not that Travis. And the Uber that you think you know—the one that magically summons a car to your location with a few taps of an app button and charges your credit card automatically—is not the one that is rapidly emerging. Just five years old and valued at more than $18 billion, Uber has had the kind of outsize, overnight success that Silicon Valley myths are made of. “Uber is going to have a bigger impact than almost anybody realizes,” says Naval Ravikant, an early investor who now heads up another rapidly growing startup, AngelList. “It’s almost the perfect tech company, insofar as it allocates resources in the physical world and corrects some real inefficiencies.”

Kalanick and his inner circle of true believers predict a future in which all commercial vehicles are “Uberized”: a time when it’s not just your car service that appears on demand using Uber's smartphone app and software—it's your Chinese delivery and your UPS packages, too. Even now, it’s easy enough to see the contours of such a vision: The company has already expanded beyond its original mission, offering lunch delivery in Los Angeles through its UberFresh program; corner-store basics in D.C. through UberEssentials, and courier service in New York through UberRush. “We always say that we deliver people in five minutes or less,” says Emil Michael, Uber’s senior vice president of business. “Well, there are a lot of other things you can deliver in five minutes or less. This is the beginning of an on-demand lifestyle we’re bringing to people.”

Ravikant believes that Uber is well on its way to being “a Google-size company,” but you don’t need a financial stake in the business to see the writing on the wall: Uber has now set up shop in more than 230 cities and 45 countries; in the United States, the company claims to cover 55 percent of the population with its network. Kalanick has said that Uber is adding upwards of 50,000 drivers (independent contractors, all) per month. According to numbers leaked to and verified by the tech gossip blog Valleywag, Uber makes up to $20 million every week—and that estimate was made almost a year (and dozens of cities) ago. Just before this article went to press, several tech blogs reported that Uber was seeking another $1 billion in funding, with a valuation of $25 billion. The company’s growth isn’t a straight diagonal line or even the fabled hockey stick that venture capitalists salivate over—it’s a lowercase “j.”

Uber is moving so breathtakingly fast that it is conceivably breaking more eggs than any tech company before it. As a matter of course, it routinely and aggressively sidesteps the law and regulation; violates industry norms; ignores ethical boundaries; and tramples on competitive relationships. In this and many other ways, San Francisco’s most controversial startup has become a symbol of the place that birthed it, a small city that is rapidly—and at times clumsily—growing into a world power. Like its hometown (or at least like certain members of the tech elite who have increasingly come to define this place), Uber is hell-bent on challenging the status quo; sheltered in a cultural echo chamber; confident in the righteousness of its ideals; and willing to make an unholy mess to achieve them.

Not surprisingly, traits like these can lead to outcomes that are unpredictable, dangerous, and at times ugly to behold. A few days before my interview with Kalanick, the company made international headlines when one of its San Francisco drivers allegedly assaulted a passenger with a hammer. A few weeks before that, the technology news site the Verge revealed details of the company’s SLOG (Supplying Long-term Operations Growth) program, in which Uber hired hundreds of independent contractors to siphon drivers and riders away from rival Lyft by way of burner phone–assisted cold calls. On New Year’s Eve of last year, a San Francisco Uber driver allegedly hit and killed six-year-old Sophia Liu and injured two members of her family. A few weeks after our interview, France’s Uber Lyon introduced a promotion that offered to pair riders with avions de chasse—rough translation: “hot chicks”—as drivers. (The gimmick was canceled after an Internet outcry.)

This parade of tragic events and embarrassing PR gaffes has been accompanied by an escalating crescendo of more fundamental complaints—from drivers angered by worsening terms of service and unsustainably low wages; from governments worried about public safety and shortfalls in insurance; from customers peeved by what some have called the price-gouging nature of the company’s supply and demand–based “surge pricing” model; and from a taxi industry that has watched in horror as it is inexorably dismantled.

So, yes. Kalanick is on his best behavior. And yes, he’s working hard to manage the message in this interview. But it’s tough to control the story when it’s being spun—and respun and re-respun—at Internet speed.

Uber’s origin story has been revised many times: In some versions, the company emerged on a mystical snowy night in Paris during an entrepreneurial jam session with cofounder Garrett Camp. But if you ask Kalanick—at least, if San Francisco asks Kalanick—it was this city that served as the company’s true inspiration. “The problem we were solving was a very San Francisco problem, on the ground and in the streets of San Francisco,” he says. “Because if you’re here and it’s before 2010, you drive everywhere, even if it’s 10 minutes away. It’s a city, and you have to drive everywhere. New York has 13,200 cabs or thereabouts, and S.F. has 1,500. If you were here before 2010, you could not get a cab. Kind of weird.”

Kalanick’s numbers are rough (San Francisco actually has 1,891 cabs), but his point stands: It’s hard to imagine Uber being founded in any other American city, if for no other reason than that no other city offers both a business climate hospitable to a startup like Uber and a transportation system broken enough to justify its existence. Anyone who has tried to hail a cab here understands intuitively that we’ve long had a serious supply-and-demand problem, but the trouble runs deeper. A couple of years ago, a Bay Citizen investigation revealed that passengers had logged some 1,733 complaints—nearly one per cab—between July 2011 and June 2012, the very period during which Uber began experiencing meteoric growth. And the town car industry wasn’t much better off, beset as it was by restrictions on, for example, reserving cars less than an hour in advance and picking up patrons at restaurants or hotels. “In the cold light of day, it’s very obvious that the taxicab system is completely broken and that rules that protect these companies shouldn’t be on the books,” says Bill Gurley, whose Benchmark Capital has invested more than $20 million in Uber. “It was just a clear abuse of regulatory power.”

And so it was that Kalanick, along with Camp, began working on Uber. In 1997, Kalanick—a whiz kid developer who had purportedly learned to code in the sixth grade—had founded a file-sharing service, a sort of proto-Napster, while still a computer science undergrad at UCLA. That company eventually filed for bankruptcy, collapsing under the weight of lawsuits from a number of corporations that weren’t wild about consumers sharing their content for free. Kalanick then founded Red Swoosh, a networking-software company that enabled users to share bandwidth. “Red Swoosh was one of those companies that was always touch and go,” says Ravikant, who knew Kalanick at the time. But Kalanick is nothing if not tenacious, and despite the post-9/11 market crash, the firm’s internal strife, and a run-in with the IRS for failing to withhold taxes (the company eventually paid the government in full), Red Swoosh was ultimately acquired by the Massachusetts-based cloud-computing company Akamai for a respectable $15 million.

In 2009, Kalanick found himself a millionaire and living in a house in San Francisco that he’d nicknamed the JamPad. (Kalanick described the scene in a blog post from that year as a place where “entrepreneurs regularly [come] to hang out, to rap on ideas, to jam with other entrepreneurs, to play Wii Tennis and Gears of War, and to have fantastic healthy gourmet meals made by the JamPad’s in-house chef.”) During this time, Kalanick fell in with a number of investors and founders, including Camp, who had previously founded StumbleUpon. Both men were flush with cash and hungry for their next project. After that fabled snowy night in Paris and a few fits and starts, Uber—then called UberCab—launched with a handful of cars in early 2010.

Despite the current popularity of UberX—Uber’s lower-cost rideshare arm that connects passengers with amateur drivers and now makes up the majority of its business—the original incarnation of Uber was intended not as an everyday transit option for everyday people, but as a luxury service for fancy people. (Or at least people who want to play at fancy for an evening. As Kalanick told an audience at an early Uber event, “You get that experience of like...‘I pushed a button, and a car showed up, and now I’m a pimp.’”)

It’s a cliché that tech startups exist to solve their founders’ problems, but in this case, the cliché seems to be true: Uber used splashy black town cars because Kalanick wanted to ride in them. “Travis is very, very aspirational,” says an acquaintance. “He wants to feel like a baller.” But the company’s original iteration as a de facto chauffeur service was also ruled by pragmatism. Town car services are governed by a different set of rules and regulatory bodies than cab companies, meaning that while entering the taxicab market would have meant wading into a thicket of complex regulatory issues, entering the private-car market was relatively painless. Supposedly.

“We started just with black car,” Kalanick says of his company’s early days. Then came competitor Lyft, which, with its goofy branding, fist-bumping drivers, and pink mustache–emblazoned cars, positioned itself as a cheaper, more down-to-earth alternative to the Uber fleet. “They came in and did the lower-end stuff,” says Kalanick, “and we stayed on the sidelines because it felt risky from a regulation perspective.” At first, Uber was conscientious—almost reverent— about following the rules. As Kalanick wrote drily in one 2012 blog post, “Uber is fundamentally different than the [person-to-person] transportation companies Lyft and Sidecar, which do not require providers to be properly licensed with the Public Utilities Commission.” Someone who knows Kalanick well recalls that “in the early days, Travis and his team were obsessed with being fully legal. It was amazing to see all of these startup guys research taxi law inside and out.”

But soon enough, regulators came knocking. In the fall of 2010, both the San Francisco Municipal Transportation Agency and the PUC served the infant company with cease-and-desist orders, largely based on the company’s use of the word “cab” in its name, which was quickly dropped. The city then started ticketing black car drivers, according to people who were present during the company’s early days. “There were a number of instances where regulators would have one rule on the books,” says Gurley, “yet their enforcement would say something different.”

“That,” says an acquaintance of Kalanick, “is when semi-crazy Travis came into the mix. If you want to get some insight into why Uber has the reputation for being above the law or being fed up with bureaucracy, there you have it. San Francisco created that. For fuck’s sake, this is a city where Gavin Newsom is considered a rightist.”

The suggestion is that San Francisco didn’t just birth Uber—it also birthed the antiregulatory philosophy that would come to dominate the company’s worldview. The city’s bureaucracy, in this reading, turned Kalanick from a largely apolitical observer who had happily shelled out for President Barack Obama’s first inauguration into a regulatory renegade who until only recently had as his Twitter avatar a detail from a cover of the libertarian bible The Fountainhead.

“Even the most progressive among us were so deeply offended by the way these dirty regulators would operate,” says Kalanick’s acquaintance. “You’ve got this company that was playing entirely by the rules and getting punished nonetheless. That sets up a company where the CEO feels emboldened to say, ‘Why the fuck should I pay attention to any of these rules, then?’ That’s what created the beast.”

Whether the decision to expand into Lyft and Sidecar’s ridesharing territory was motivated by revenge or by a long-standing desire to offer services at various price points, as Kalanick and others have later claimed, there’s no doubt that it changed Uber’s trajectory forever. “That was the real inflection point for Uber,” says Ravikant. “It really changed everything. That took Uber from being a special-occasion product, something that 5 percent of the population is gonna use, to something that 25 or 30 percent is gonna use.”

Indeed, this is the brilliance of Uber: The company didn’t just take over an already existing market by replacing cabs—it helped create an entirely new one. Today, the number of Ubers taken per day in San Francisco vastly outstrips the total number of daily cab trips taken when the company was founded in 2009. “It was really off to the races after that,” says Gurley. In 2011, the company received almost $50 million in funding from various venture firms; that same year, it expanded to New York and then Chicago. The company now has 1,700 corporate employees (700 in San Francisco) and hundreds of thousands of drivers worldwide. In September, Uber announced that it had outgrown its offices for the eighth time in five years and would soon be developing a 10-story, 423,000-square-foot Mission Bay space with room for 2,000 employees. It has become a San Francisco colossus.

To get anyone to talk about life at Uber HQ is roughly as easy as hailing a Yellow Cab in downtown San Francisco—in the rain, on New Year’s Eve. Employee nondisclosure agreements and blanket proscriptions on talking to the press are standard among image-conscious tech companies—indeed, Uber requires visitors to its office to sign a two-page, fine-print contract. But after weeks of reporting this story, it becomes clear to me that Uber has created an almost Apple-esque apparatus of secrecy. All of the half-dozen-plus current and former employees who agree to speak with me do so only under the condition of complete anonymity. Two of them won’t even allow me to take notes. One refuses to discuss the piece in writing whatsoever, even in personal text messages and email. But those to whom I do speak—even employees who are or were generally happy to work there—independently describe a work culture of rapid-fire promotions and demotions, of high stakes and high rewards and even higher levels of fear, of lots of pressure and little emotional support. “It’s definitely aggressive and competitive,” says one former staffer. “It’s not a place you should work if you don’t want to be on call 24-7.” Indeed, employees report that it’s not uncommon to see company chat rooms running at 3 or 4 in the morning or to be called in for a 9 p.m. meeting (though, in classic Kalanick jargon, they’re typically called “jam sessions”).

Gurley recalls an episode from the company’s early days: An employee sent an email to Kalanick raising some issue and mentioning that he didn’t want to hurt a fellow employee’s feelings. “Travis called an all-hands meeting to talk about it,” Gurley says. “Not that people’s feelings don’t matter, but he didn’t want the company making decisions for that purpose. He made it clear that we need to be looking for the right answers and not let [personal] politics get in the way.”

“How was he?” an employee asks me when I mention that I’ve interviewed Kalanick. I tell him the truth, which is that his boss seemed like a nice, if odd, guy.

“That’s because you haven’t fucked up,” the person says, laughing.

Uber’s hard-charging culture trickles down to the company’s hundreds of thousands of drivers, who are automatically fired for earning an average rating below 4.7 stars, according to some drivers (all drivers are rated by every passenger they drive), and can be disciplined or booted for any number of infractions. These conditions add kindling to driver complaints about ever-decreasing pay—in the last year or so, the company has both slashed fares and increased its per-ride commission to between 20 and 28 percent, depending on the car type. As contractors, Uber drivers pay out of pocket for all costs they incur, including gas and maintenance; they’re also paid per ride, meaning that the work is unpredictable. The way that many drivers see it, they’re casualties of a brutal race to the bottom between Uber and its competitors. This summer and fall, drivers around the world staged protests and work stoppages (though their efforts appear to have fallen on deaf ears). Though Uber often repeats the claim that its drivers can make a median of $74,000 a year in San Francisco, numerous reports indicate that this figure is rosy at best, willfully misleading at worst: Some cursory arithmetic based on numbers from Uber’s blog reveals that to make that much, drivers would need to complete 3.4 full rides an hour—or work a lot more than 40 hours per week. Further, the $74,000-a-year figure is gross pay, which doesn’t account for the cost of gas, car maintenance, and the like.

“You get in the habit of not identifying yourself as an Uber employee when you’re a passenger, that’s for sure,” a former corporate staffer tells me. “A lot of people say they work at another company in the building when getting picked up or dropped off at HQ.”

The take-no-prisoners ethos extends to the company’s dealings with local government. In every city where the company bumps up against regulation—which is most of them—Uber’s armies of staffers launch a vast and complex offensive, a combination of behind-the-scenes deal making and very public PR overtures. In Washington, D.C., the company enlisted would-be users to barrage local government with more than 50,000 emails pleading its case. In Denver, it held a rally of several hundred people. And nearly everywhere, the company’s model has been to set up shop first and wait for regulation to follow. “Uber is so well funded, profitable, and powerful in the marketplace that there’s not a whole lot of incentive to play nice,” says a former employee. All told, it’s not just that Uber has adopted the business school maxim “Don’t ask for permission; ask for forgiveness”—it has instituted a policy of asking for neither.

All along, this brazen approach has been matched by Kalanick’s rhetoric. “We’re in this political campaign, and the candidate is Uber, and the opponent is an asshole named Taxi,” Kalanick told the audience at a tech conference earlier this year. “Nobody likes him, he’s not a nice character, but he’s so woven into the political fabric and machinery that a lot of people owe him favors. We have to bring out the truth about how dark and dangerous and evil the taxi side is.” (Locally, at least, the strategy is working: According to the SFMTA, between January 2012 and July 2014, the number of monthly trips per cab plummeted from 1,424 to 504, a decrease that the agency attributes largely to the rise of Uber and its competitors.)

In his more off-the-cuff days, Kalanick made repeated references to “destroying” the cab industry. After the company raised the ire of some customers for charging several times normal rates as part of its “surge pricing” model, he posted a screenshot of an email from an irate customer to his Facebook page, imploring his friends to “get some popcorn and scroll down.” Recently, the company launched an anti-Lyft ad campaign with the cheekily violent tagline #shavethestache, proving that even the toned-down version of Kalanick is still a fighter through and through. “Travis has a severe underdog mentality,” says Ravikant. “He’s scrappy. He can’t turn it off. Maybe he should turn it off. It really is like, only the paranoid survive.” Even these days, handled as he is, it’s hard to imagine Kalanick claiming purity of purpose or positivity of intent with a straight face the way that so many other Valley CEOs do.

Indeed, when I press Kalanick about his larger-order motivations, he discusses his work in terms that are less about addressing global problems than they are about solving relatively small-scale intellectual puzzles. “Why do I wake up in the morning?” he asks. “For me, it’s one of these moments I get once or twice or three times a day, solving some really interesting problem. And there’s a breakthrough, and something really fun and interesting comes out of it. That’s what’s so awesome about this job. Imagine having that moment two times a day with a set of people around the table who you deeply respect. That’s pretty cool.”

At this point, Kalanick has learned enough from his public stumbles to emphasize the company’s positive impact on the world: He argues, convincingly, that Uber has reduced drunk driving, made car ownership less necessary, lowered greenhouse gas emissions, and generated tens of thousands of jobs. When he says, as he often does, that his company is “changing the way cities operate,” it’s impossible to disagree with him.

However, it’s clear that on an emotional level, he is driven by a purpose not quite as high as his handlers might hope. This is Kalanick at his essential, pragmatic core. According to Gurley, Kalanick is fond of the Valley idiom “one truth”—that is, “he’s always pushing the organization to identify the exact right answer.” He has become an avowed enemy of cabs not because of any ethical outrage over the industry’s failings, but because they’re a staggeringly inefficient way to get the “one truth” of transportation: a fast, safe, and reliable path from here to there.

“There’s been a growing trend of entrepreneurs who are very product-centric,” says Gurley, “who I think almost dislike the business side of things. I think [Facebook’s Mark] Zuckerberg has some of that. A lot of these touchy-feely, product-oriented founders don’t think of building the business side of the house nearly as much.” Kalanick, on the other hand, “is different. He loves business. We went to the Ford headquarters, and he had a huge smile on his face the whole time.”

Like its founder, Uber is a deeply rational, entirely bottom line–oriented entity. “I call us grounded,” says Kalanick, “but that makes sense given what we do: Rubber meets the road...on the ground. There’s a pragmatism that’s necessary to do what we do right and do it well.” According to employees, the internal rhetoric is less about blandly upbeat enlightenment than it is about concrete problem-solving. “There isn’t any overlay about saving the world,” says a former employee.

All of which points to a truth that’s crucial to understanding this company, and how it sees itself: There’s a counterintuitive, almost discomfiting way in which Uber is actually more trustworthy than most companies coming out of Silicon Valley these days. In an industry so obsessed with euphemism and obfuscation and pious abstraction that it’s become a trope worthy of HBO satire, the baldness of Uber’s ambition is bracing. There’s something perversely satisfying about a CEO saying, as Kalanick did at a Y Combinator event in 2012, “When I’m having a bad day, I just go [look at] our revenue graph.”

It’s instructive, for example, to compare Uber’s rhetoric with that of Lyft, which describes itself as “your friend with a car,” conveniently glossing over the fact that we don’t typically pay our friends per mile for rides. Or consider Airbnb, another sharing-economy behemoth that is disrupting a deeply entrenched system and is thus often mentioned in the same breath as Uber. Where the short-term-rental broker couches its quest to eviscerate the hotel industry in pastel colors and candy-coated declarations (as a recent spate of much-derided New York City subway ads chirped, “Airbnb helps local businesses in our neighborhoods and strengthens our community”), Uber makes few such promises.

Uber is not claiming, as Google famously did, to not be evil, nor is it purporting to be an earnest attempt at fostering connections and building community. It’s never really pitched itself as a company that does much beyond building an exceptional product, rolling it out as quickly and efficiently and cheaply as possible, and, of course, minting money by the billions.

Not that everyone appreciates this kind of radical emotional honesty coming from a corporation. “Sure, Uber is authentic to their core ideals,” the venture capitalist turned author Peter Sims tells me one afternoon in October. “But let’s consider what Uber’s core ideals are. I’ve met hundreds of founders and been to thousands of companies. Uber is the most arrogant company I’ve encountered, and the most unethical. I don’t say that lightly.”

For Sims, the last straw came in 2011, when he received a text message from an acquaintance in Chicago while in New York, asking if he was in an Uber; he later discovered that the company was broadcasting his car’s location as part of a live demonstration at a Windy City launch event. “Much as I am impressed with the product design and many aspects of the user experience,” he later wrote in a now widely circulated post on the web publisher Medium, “I’ve given up on being able to trust the company.”

Sims’s post came amid a raft of anti-Uber press earlier this year. “There’s little doubt that Uber is the closest thing we’ve got today to the living, breathing essence of unrestrained capitalism,” Andrew Leonard (a contributor to San Francisco) wrote in a blog post for Salon bluntly titled “Why Uber Must Be Stopped,” published after the SLOG revelations. “This is how robber barons play. From top to bottom, the company flaunts a street-fighter ethos.”

Even super-investor Peter Thiel, who is famed in the Valley and beyond for his ultracompetitive spirit and hatred of regulation (and who is, perhaps not incidentally, a Lyft backer), objected to the company’s ethos: “There’s always a question, you know,” he said on CNBC in September, “of how intensely you’re allowed to compete, and Uber is right at the line.”

“Employees lose track of the bad press because it happens so much,” says a former Uber staffer. “Every morning you get a rundown of all the press mentions, good and bad, in your in-box, and most people don’t even read it.”

Kalanick bristles visibly when I bring up the company’s media coverage. It’s clear that he feels victimized by a tech press that he believes has rushed to judgment. “Imagine if you put many, many years of your life into something and were passionate about it,” he says plaintively, “and you spent every waking moment putting love into it and trying to make it better, and people didn’t understand that. You’d want them to.”

The way Kalanick tells it, Uber’s bad press has less to do with the substance of the problems themselves than with the way they have been spun to the public: “We’re just technologists. We haven’t always been able to get the sort of positive parts of Uber out there.” When I ask him for specifics, he ticks off a list of appealing qualities with the facility of a very smart person who has memorized a script. “We haven’t been great at talking about how tens of thousands of jobs in a single city are being created, how this is reducing congestion in the city, how many cars are off the road because of this, how good this is for the environment,” he says. “We have to do a better job of telling this very—I don’t want to say obvious—but the very clear stories about the good things that are happening.”

To correct this deficiency, earlier this summer, Kalanick did a very Kalanick thing: He hired former Obama campaign mastermind David Plouffe to be what he calls “Uber’s campaign manager” (this is the HR equivalent of ordering a super-stretch limo over a basic taxi). The hire is as indicative of the new world order that Uber represents—in which corporations interact with governments so intimately that they become para-municipal organizations themselves—as it is of Uber’s newfound interest in public appeasement. Kalanick’s mild manner during our interview was but one example of a concerted media effort to evoke what TechCrunch has described as a “kinder, gentler Uber.” Quietly but clearly, the CEO has launched something of an apology tour—tamping down the aggro “asshole named Taxi” rhetoric just a little, appearing contrite at conferences and industry events. (The story that you’re reading is in fact part of the company’s charm offensive: At the photo shoot for our cover, Kalanick repeatedly expressed concern about looking like an “asshole.”)

This is a difficult line for Kalanick to walk: Uber, like so many other start-ups, is a company that was created in its founder’s image. “There’s no one else I can imagine doing this,” says Michael, Uber’s business lead. “I cannot imagine another person who could take on this battle and win.” This is a polite way of saying what many others would only tell me anonymously: that Uber owes much of its success to the megalomania of its CEO. After all, broken as the taxi system may be, it’s a powerful lobby, and it takes a truly passionate, determined, even arrogant person to willingly go up against it.

Now Uber—or at least the unfortunate souls in its PR department—is faced with the delicate work of de-jerking the CEO without completely lobotomizing him. “I would guess,” says Ravikant, “that you’re gonna see Travis tone it down a bit in the future.” A wise strategy, it’s safe to say. Unlike, for instance, Oracle—to whose mercurial, occasionally alienating erstwhile CEO, Larry Ellison, Kalanick is often compared—Uber is wholly dependent on its base of customers having positive associations with it. As Sims argues, “Uber is, ultimately, a consumer brand.”

But, counters a former employee, “consumers aren’t necessarily reading TechCrunch or PandoDaily. Consumers are trying to get from Point A to Point B.” It’s crucial, the former employee says, to remember that “this is an engineering- and business-driven company. These people are looking at numbers—they’re not looking at how people feel. And when they see the numbers, let me tell you, they have a big smile on their face.”

This, in the end, is what’s so vexing about Uber: It is, undeniably, a great San Francisco company—and may turn out to be the most useful and lasting of the hundreds conceived during the current boom. After years of following Uber’s rise with a mixture of awe and terror, I will cop now to using the service several times a week. As a legally blind resident of the relatively sprawling city of Oakland whose disability prevents her from driving, I myself represent precisely the kind of person whose life Uber has made demonstrably better. No matter how conflicted I feel when a shiny Prius pulls up to the curb in front of me, driven by my underpaid “private driver,” I can’t pretend that the company hasn’t empowered me to do things and go places that I wouldn’t have been able to four years ago. And clearly, the feeling is widespread: You don’t get millions of users with a subpar product. As one UberX driver recently told me, “No one ever gets in my car and says, ‘Gee, I wish I were taking a cab.’”

Ultimately, says someone who knows Kalanick well, the moral of the story of tech’s most ruthlessly hyper-capitalistic company may be that the free market really does take care of itself. “With Uber, I’m like, what am I gonna cringe about next?” the person says. “But you know, you can’t argue with somebody who’s printing money. That might be the lesson here: Build a good product, and it doesn’t fucking matter.”

Originally published in the December issue of San Francisco

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