How to Get Away
with Uber

What exactly is it about the controversy-baiting, aggressive, indispensable taxi app that pisses so many people off? (Hint: It’s not the bullying, the bro culture, or the surge pricing.)

By Bobbie Johnson
Photographs by Richard Petrucci


Roberto Chicas doesn’t use Uber anymore. Actually, he doesn’t do much anymore, not since he met Patrick Karajah. It was one night in late September, when Chicas, a bartender in San Francisco, did what many San Franciscans do: He summoned Uber to get him home. Karajah, the on-demand driver who answered his request, picked up Chicas and his two friends. During the journey, the friends say, everyone got into it about which route to take. Eventually, just off I-280, on a scrubby little patch of land between a housing complex and the freeway, Karajah threw them all out of the car, pulled out a hammer and allegedly smashed it, just once, into Chicas’s face. Karajah then climbed back into his car and drove off, leaving Chicas fading in and out of consciousness on the sidewalk with multiple skull fractures. Roberto Chicas has pretty good reasons to hate Uber.

My first Uber wasn’t anything like Chicas’s. It was probably a little bit like yours. We were at a friend’s birthday party, and after a few songs, some inadvisable dancing and even more inadvisable shots, my wife and I stumbled out onto the street and into the rain. Taxis are a precious enough find in most parts of San Francisco, and on damp, foggy evenings they are even more rare. We were stuck and needed to get home and relieve the babysitter, so I grabbed my phone, downloaded the Uber app, added my credit card details, ordered a town car. It turned up in just a couple of minutes, and I can tell you now, it was joyous. I’ve waited longer for a sandwich.

This is exactly what Uber is great at: Supreme, ludicrous, almost ostentatious convenience. It’s a company built to directly service what seems to be the guiding principle of 21st-century urban living. There are so many trying to grab a slice of this on-demand industry — on-demand cleaning, on-demand dry cleaning, on-demand hair-styling, on-demand ice cream, on-demand marijuana— but let’s face it, anyone who knows anything knows this: Uber is The One. It’s more powerful, more convenient, more available, than every other player in the game.

Uber makes everything so easy. And that includes hating it. Not the Roberto Chicas kind of hating it, but something more fluid, more rubbery, harder to pin down.

The company, valued at $18 billion and rising, holds a strange position in the technology industry. Among a legion of highly detested companies, in a highly detested business, it is the thing people hate the most. And the reactions against it are powerful, instinctive, and often hard to articulate.

So why, exactly, do we hate Uber?

Maybe we hate Uber because it has risen astonishingly fast. It started operations just four years ago, and now it’s in 200 cities across 45 countries. This summer it raised $1.2 billion in funding to grow even bigger. For some, that wealth creates anxiety. For others, it means jealousy. In any case, it means Uber has reached the love-hate moment faster than most, and in the past few months there have been organized protests against its labor practices and legal status, and suits filed against it for everything from its gratuity charges to wrongful death.

Maybe we hate Uber for its ultra-competitive, ethics-dodging business tactics. Uber staff have been caught in a variety of ethically compromising positions, including deliberately calling up drivers from competitors like Lyft and then canceling the job at the last minute, or catching the rides and offering rival drivers a pile of cash to switch allegiances right then, right there. It certainly makes them hard to love.

Maybe we hate Uber because of surge pricing. For economists and libertarians, it’s the fantasy of a perfect supply-and-demand pricing system. For riders, it seems like Uber constantly demands that you supply it with all your cash. Just imagine what it’ll be like over Thanksgiving.

Maybe we hate Uber because it chews away at our social fabric. Taxi drivers and local government, two of the company’s favorite targets, are hardly beloved — but the world Uber is creating instead is not exactly a utopia, either. It’s basically advocating for the destruction of thousands of flexible-but-secure jobs in favor of a far greater stream of McJobs, where almost anybody can sign up to drive, but those who do are at risk of being fired if their ratings drop anything below almost-perfect.

Or maybe we hate Uber for its hypocrisy. For a company that rails against the system, Uber certainly plays footsie with it a lot. It lobbies as hard as it competes, trying to influence the politics of the cities it wants to colonize, happily building astroturf campaigns and spending that vast pot of cash. Need more proof? It hired David Plouffe — Obama’s David Plouffe!— as policy chief to try to manage its political strategy.

All of these things make sense, they’re all solid reasons. But they’re also not unique. WalMart, McDonald’s, BP… the list of companies that struggle with the media, manipulate the rules, and lobby politicians is endless. So the question’s still there: Why do we hate Uber so much?

Maybe it’s the boss. Travis Kalanick, who is the face, voice and apparently ever-present super-ego of Uber, is not just a douchebag CEO. He is a caricature of a douchebag CEO. He is brash, unforgiving, constantly yukking it up at the expense of his competitors. His face seems to be eternally contorted into one of those smirks that reminds you of the bad guys in The Karate Kid: He’s beaten you; You know it; He knows it; But he also wants you to know that you both know it, and get it into your fat head that there’s not a fucking thing you can do about it. Unlike most of the moneyed princelings of Silicon Valley, who struggle — at least a little — with the public perception that they’re wacky technocrats or robber barons, Kalanick doesn’t reject a negative perception. He revels in it, or at least he does most of the time.

He is as aggressive as his business, and he’s certainly not afraid to bully his way to getting what he wants. Kalanick calls his rivals out as “evil” at public events, says he’s in a fight with “an asshole called Taxi,” and stands out front in the company’s announcements and says “that’s hashtag winning.” He bros it, and he’s proud.

This plays well with the media, which is always hungry for anyone willing to play the pantomime villain. And in a tech world where, frankly, most CEOs are anonymous repetitions of the same geek-kid stereotype, somebody who is so brazen, so Dickensian, makes for easy copy.

But the reporters who enjoy the spectacular tales of Uber’s arrogance can also be on the sharp end. Uber henchmen regularly take it upon themselves to chide journalists who criticize the company, and sometimes they — and Kalanick himself — go much further. Last year the CEO attacked a Reuters report on a push for new investment as “completely false” and the product of “extremely poor reporting and journalistic ethic.” (Reuters took the story down, but three months later, it emerged that it was really inaccurate only in one sense: It didn’t value the company’s stock high enough.) Others say Kalanick has privately used this episode as an example when threatened with other inconveniently-timed stories even though they were also later proven true. Then came the latest backlash, which started when a senior executive “joked” to BuzzFeed about hiring opposition researchers to expose the personal secrets of a critical reporter, PandoDaily’s Sarah Lacy, in order to stifle criticism. It was dismissed by Kalanick as “not representative in any way of the company approach.” In fact, it’s entirely typical: BuzzFeed has since run documents showing Uber was interviewing opposition researchers with an intent to “weaponize facts” against its competitors.

Kalanick’s brand of ruthlessness is not an accident, it’s more a core character trait. He’s been banging around Silicon Valley since the first boom, a two-time almost-made-it kind of entrepreneur whose desperation to win is tangible. His first start-up, a file-sharing service à la Napster, went bankrupt after it was sued for a quarter of a trillion dollars; his second, which made distributing large files faster, delivered a moderate pile of cash but not very much glory. His desperation to matter seems to be at the center of everything. And maybe we hate Uber because it’s built in that image.

But, then again, the business world is full of wannabes, bros who fist-bump every time they screw over some old lady or make some desperate family homeless. They’re the people who buy their way out of billion-dollar court cases, the ones who control the vampire squid. Even if Kalanick is a gigantic asshole, he’s not alone. So the question’s still there: Why do we hate Uber so much?

Maybe we hate Uber because it’s a typical Silicon Valley startup. It’s not unusual for technology companies to be despised — in fact, it’s much more unusual for them to not tap into vast, unexpected wells of hate as they grow. Every big tech company begins life as a scrappy upstart, working out some kink in the system that makes it useful, and then using that as leverage to build itself into a giant, sprawling service — whereupon it becomes both invaluable and infamous. It’s a rite of passage to really fuck things up somewhere along the way. Yahoo’s exclamation mark didn’t look so fun the moment it started handing over people’s personal details to the Chinese government and getting dissidents thrown in jail. Facebook has freaked everybody out multiple times by trying to redefine basic human concepts — friend, like — to match its commercial goals. Google set its self up early for this particular kind love-hate relationship, thanks to its handy Don’t Be Evil motto, which got harder to live up to as it bought its way into every privacy-invading, terrifying-future scenario imaginable, from street photography to mobile phones to military robotics to glasses that spy on you. Is that where Uber’s at? I asked Uber to explain why it thinks everybody hates it, but sadly the company didn’t respond to my request for comment.

But here’s the other thing about nearly every high-growth internet start-up: They don’t really work… until they work. Start-ups are an attempt to make us believe in magic; to turn the illusion of success into reality. Once something gets big enough — especially if it gets big enough fast enough — it gains its own kind of gravity. At the moment it works, a new market has been made, or an old market has been made obsolete, and that’s when the business effectively gets its license to print money. In the case of a company like Google, the difference was being faster and more comprehensive than the competition: It became big enough because there was no better place to navigate your way around the Web, which meant there was no better place to advertise. Facebook reached the same point by making a photocopy of your social relationships that made it the homepage of choice for hundreds of millions of people, which meant there was no better place to advertise. For a company like Uber, which requires vast amounts of on-the-ground effort to get bigger, that kind of growth is insanely expensive. Yes, the software plays a part, but it’s really a people business. That’s why the company has so many competitors, and it’s why it needs to be so aggressive: Because even if it is pulling in tens of million of dollars every month, its only real competitive advantage is size, and it only maintains that advantage by pushing outward in every way it can.

Constant expansion is so expensive that it has plenty of people worrying about Uber’s long-term prospects. Remember, it’s currently active in more than 200 cities. Crudely, given that it’s taken $1.4 billion in total fund-raising, that’s $7 million per city. It sounds like a lot, and it is. And there is clearly plenty of money coming in from those thousands upon thousands of car rides being taken — documents leaked this week to BusinessInsider showed that even a year ago, the company was already generating tens of millions every month in revenues. But each city presents a huge set of political and logistical challenges, often with plenty of local peculiarities thrown in for good measure. Uber’s success in one place doesn’t necessarily make conquering the next city easier, or cheaper. And because start-ups don’t work until they work, the conundrum is always the same: At which point does the amount Uber is making outstrip the amount it’s spending? At what point does it really work?

“Uber reminds me a lot of Webvan,” tweeted Benedict Evans, a partner at Andreessen Horowitz, Silicon Valley’s hottest venture capital firm, which is an investor in Lyft. “Fascinating city-by-city algebra to make the numbers work, plus massive burn in a play to conquer the world.”

He’s referring to the online delivery service that, at the height of the dot-com boom, promised 30-minute delivery of groceries to users in cities like Chicago, L.A., and Dallas, as well as across Northern and Southern California. It raised hundreds of millions in funding to try and achieve hypergrowth, but in the end it just couldn’t make the numbers work, and went bankrupt in July 2001. Supporters may scoff at the comparison — c’mon, man, it was years ago, the world’s different now, we’ve all learned our lessons — but there are plenty of similarities.

That’s because the math of any city-by-city operation is tough: You spend money to get control of the market in the hope that eventually the numbers come good — but it’s all down to how much cash you have, how much you spend, and how long you wait. Uber has plenty of investment, but the scale is gigantic. Consider Groupon, a shooting star that just a few years ago had the same kind of trajectory, and the same kind of problems, and now is a dot-com also-ran.

But even though all of this might be true, it still doesn’t answer the question of why Uber is so hated. After all, what do we really care if Uber blows up, or collapses in disgrace? The question’s still there.

If you really want to think about why we hate Uber, the best place to start might actually be 20 years and 800 miles away, in the suburbs of Seattle. That’s where Jeff Bezos founded Amazon, the company that is the best single model for understanding what Uber is, and what Uber wants to be.

Amazon also started out with a simple, attractive proposition in a single, focused market. It sold books online! Suddenly, at least theoretically, the sum of all human knowledge could be delivered to your doorstep with a click. Who could argue — I mean really argue — with that? Sure, booksellers could feel the pinch. And publishers got collywobbles about the changing relationship between the producer and the distributor. And Jeff Bezos was a notorious shitbag, who became infamous for upbraiding employees, pushing them to work every waking hour, treating them like dirt. But the reality? It didn’t take long until Amazon seemed indispensable. For every human being who was being trounced behind the scenes, there were many more who started using Amazon and just couldn’t stop. It made everything so easy. A glance, a click, a package delivered right to your door. The pure convenience was an addiction.

Bezos, in between those spittled attacks on his own staff (“Are you lazy or just incompetent?”), masterminded one of the greatest Trojan horse campaigns in business history. Now, of course, Amazon delivers everything: books, toys, video games, kitchen equipment. It delivers media. It makes e-readers, it makes tablets. It makes phones, for God’s sake, even if nobody buys them. Its Web services division builds the infrastructure that helps run many of the sites and services you use every day (including the one you’re reading right now). And you probably never realized all this was happening until it had all happened.

Travis Kalanick certainly knows who his heroes are. He rejects the Amazon comparison, but he’s made no secret of his admiration for Bezos (who was, in fact, an early Uber investor), or his envy of Amazon’s relentless march from a mere supplier of services to a business that maintains a choke hold on modern life (Amazon was, in fact, almost called Relentless.com). “Amazon was just books and then some CDs, and then they’re like, you know what, let’s do frickin’ ladders,” Kalanick told Wired earlier this year. “We feel like we’re still realizing what the potential is… We don’t know yet where that stops.”

Amazon — more than any other company, more than Google, more than Facebook, more than Apple — taps into what people desire in a terrifyingly primal way: We want a thing, fast and preferably cheap. Not much else matters. We know Amazon’s not a nice company, and that the people who work there are treated poorly. We don’t always like it, but there is absolutely, definitively, nothing we will do to stop it. We are happily addicted.

That same feeling is there with Uber, except one thing: We know where Amazon has ended up, more or less, but we don’t know where Uber’s going to stop. Maybe, for Uber, it doesn’t stop at all. For Kalanick and his team, the means are the end. There is no greater mission. There is only hunger.

Raw, pure, unbridled ambition is an uncomfortable thing to look at. It’s not that it’s ugly, necessarily. It’s just brutally, shockingly honest. Uber does not pretend to have a glorious philosophy—it wants to make transport easy, but there is no aspiration as lofty as “organize the world’s information” or “make the world more open and connected.” And perhaps that’s the way it should be. After all, would it be more offensive if Uber had a mission beyond itself? It certainly feels like less of a betrayal to know that it just wants to be as big, as powerful, as necessary, as it can be.

That ambition shows, though, perhaps too often. Uber likes to think of itself as secretive, but rumors slip constantly out of the mother ship. There was the one about it hiring executives away from Google Shopping Express, in a move that could help it build out its delivery network and damage one of its potential rivals in one fell swoop (confirmed earlier this month). Or the one that it’s about to start on-demand booze deliveries. It usually denies these rumors, even though depending on where you live, you can already Uber courier services, groceries, restaurant meals. When these things turn into publicly available services — on-demand weddings, on-demand ice cream — they’re often positioned as stunts. But in reality, they’re all trial balloons, tossed out onto the breeze to float upward, as the company’s ambitions stretch toward the sun.

Yes, it’s hubristic. The company’s rise has fuelled plans for a gigantic new office complex in San Francisco, with 425 parking spots included (ironic for a company that says it will eliminate car ownership). And yes, it’s absurd — at least it is if you think that it’s just a fucking taxi app. But all of these pinpricks point toward an endgame that goes way beyond most of the companies we’ve seen before: They point to Uber as a central service provider for urban living.

It doesn’t want to be just an on-demand transport company, and it doesn’t even really want to be the Amazon of on-demand services. The next step in its ascent is to become the Uber of everything, and then — eventually, Uber wants to be the Everything of Everything.

The dick-swinging, the gluttony, the not-quite-lies and the full-on bullshit… All of these things, and in particular the spectacular combination of all of these things, are enough to dislike a company, and even to hate it. But it’s incredibly popular, too, because, man, if people vote with their feet — or in this case their fingers — then they keep voting, again and again, for Uber.

And that, in the end, is the real reason so many people hate Uber: Because whatever we do, we can’t stop ourselves from making it bigger and more successful and more terrifying and more necessary. Uber makes everything so easy, which means it shows us who, and what, we really are. It shows us how, whatever objections we might say we hold, we don’t actually care very much at all. We have our beliefs, our morals, our instincts. We have our dislike of douchebags, our mistrust of bad behavior. We have all that. But in the end, it turns out that if something’s 10 percent cheaper and 5 percent faster, we’ll give it all up quicker than we can order a sandwich.

A previous version of this story forgot to state that Andreessen Horowitz is an investor in Uber rival Lyft. Matter regrets not spotting the pink mustache.

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