Super Pumped: The Battle for Uber

by Mike Isaac

You must know there are two ways of contesting, the one by the law, the other by force; the first method is proper to men, the second to beasts; but because the first is frequently not sufficient, it is necessary to have recourse to the second. —NICCOLÒ MACHIAVELLI, 1513

They worked for the Portland Bureau of Transportation and had a mandate: Find and stop anyone driving for Uber, the fast-growing ride-hailing startup. After months of trying to work with city officials to make the service legal in the city, Uber had thrown negotiations out the window. The service was launching that evening, without the bureau’s approval.

Uber’s nice-guy approach hadn’t worked. But it wasn’t designed to. Over the previous five years, the company had grown from a startup employing a couple of techies in a San Francisco apartment to a burgeoning global behemoth operating in hundreds of cities across the world. It had done so by systematically moving from city to city, sending a strike team of employees to recruit hundreds of drivers, blitz smartphone users with coupons for free rides, and create a marketplace where drivers were picking up passengers faster than the blindsided local authorities could possibly track or control. This was the plan for Portland as well, no matter what the mayor and his enforcer had to say. And Travis Kalanick was tired of waiting.

The problem wasn’t Uber’s black car service, which functioned well in a number of cities because it adhered to standard livery and limousine service regulations. The problem was UberX, an ambitious, low-cost model that turned nearly anyone on the road who had a well-conditioned car and could pass a rudimentary background check into a driver for the company. Allowing random citizens to drive other people around for money opened up a slew of problems, most notably that no one had any idea whether or not it was legal. At Uber, no one really cared. Kalanick didn’t think much of the nice-guy approach to dealing with cities. He believed that politicians, when it came down to it, would always act the same way: they would protect the established order. It didn’t matter that Uber was transformational, a way for people to catch a ride from a stranger with just a few taps on their iPhone. The new model pissed off the taxi and transit unions, and those people would flood the mayor’s office with angry phone calls and emails. Uber, meanwhile, would happily rake in the cash, and do so with a groundswell of public support from locals who loved the ease and simplicity of the service.

What England didn’t know was that Uber’s general managers, engineers, and security professionals had developed a sophisticated system, perfected over months, designed to help every city strike team—including the one in Portland—identify would-be regulators, surveil them, and secretly prohibit them from ordering and catching Ubers by deploying a line of code in the app. The effect: Uber’s drivers would evade capture as they carried out their duties. Officers like England could not “see” the shady activity, and could never prove it was happening.

Behind the scenes, Uber was hardly innocent. Recruiting ex-CIA, NSA, and FBI employees, the company had amassed a high-functioning corporate espionage force. Uber security personnel spied on government officials, looked deep into their digital lives, and at times followed them to their houses. After zeroing in on problematic individuals, the company would deploy one of its most effective weapons: Greyball. Greyball was a snippet of code affixed to a user’s Uber account, a tag that identified that person as a threat to the company. It could be a police officer, a legislative aide or, in England’s case, a transportation official. Having been Greyballed, England and his fellow officers were served up a fake version of the Uber app, populated with ghost cars. They had no chance of ever capturing the rogue drivers. They might not even know if drivers were operating at all. For the next three years, Uber operated with impunity in Portland. It wasn’t until 2017 when the New York Times broke the story of how Uber used Greyball to evade the authorities that Portland officials fully understood just how Uber had carried out its subterfuge. But by 2017 it was too late. Uber was up and running in Portland—legally, even—a fixture of the city, in regular use by citizens who praised its convenience. Kalanick and his team had violated local transportation laws, and instead of being exiled, they had found enormous, game-changing success.

Greyball

Greyball was consistent with one of Uber’s fourteen company values: Principled Confrontation. Uber was protecting its drivers while confronting what they saw as a “corrupt” taxi industry that had been protected by bureaucracy and outdated regulations. Concepts like “breaking the law” weren’t applicable, they believed, when the laws were bullshit in the first place. Kalanick was convinced that once everyone used the service, it would click—they’d understand that the old way was inefficient and expensive, and his way was the right way.

As a Bay Area resident and professional journalist during the past decade, I saw Uber rise to power right in front of me. I witnessed how quickly a transformative idea can change the urban fabric of a city, and how strong personalities can have an outsized effect on shaping the way a startup operates.

He went on to advise his staff not to throw large kegs off of tall buildings, and mandate no interoffice sex unless co-workers explicitly stated “YES! I will have sex with you” to one another.

But for every WIRED cover story of a boy genius striking it rich with a smartphone app, there was a mess of secondary effects left in his wake. Many of the next generation of apps catered to the needs and whims of the white, upwardly mobile twentysomething males of Silicon Valley. The press gave significantly less ink to the latent misogyny bubbling up inside of tech companies, and the libertarian view that enabled tech figureheads to unwittingly enable these same biases. The divide between tech’s most talented, and the class who waited tables and served them coffee only grew starker by the day. Fast-rising rents pushed wage earners out of San Francisco, while landlords flipped those former apartments to new, wealthier tenants. The “gig economy” unleashed by companies like Uber, Instacart, TaskRabbit, and DoorDash spurred an entirely new class of workers—the blue-collar techno-laborer.

“There are forces all around you when you run a company, . . . ready to take you out,” Kalanick said. “The [CEOs] that survive are the ones that are supposed to be there.”

Amazon Web Services powers cloud computing services for coders and entrepreneurs who can’t afford to build their own infrastructure or server farms on their own. If a startup is a house, AWS is the electric company, the foundation and the plumbing combined. It keeps the business up and running while the company founders can spend their time focusing on more important things like, say, getting people to come to their house in the first place.

Garrett Camp was pissed off. It was 2008—the twenty-first century—in one of the richest, most forward-thinking cities in the entire world, and he couldn’t catch a taxi in under a half hour. At only seven-by-seven square miles, San Francisco was small enough that one could survive without owning a car, but still large enough for a person to be annoyed they didn’t have one. He could always bike across the city, though a six-speed didn’t work so well climbing up steep hills like those on Divisadero Street. And a bike wasn’t going to help him get home from a bar at two o’clock in the morning—at least, not without a DUI or a head injury. There was always BART—Bay Area Rapid Transit—San Francisco’s wheezing commuter rail system. But BART was gross, a patchwork of dirty cloth seats and crowded cars, nowhere near large enough for the influx of twentysomethings who had invaded the Bay Area in recent years. And BART didn’t run past midnight. Not ideal for a young man pursuing the nightlife.

Garrett Camp still couldn’t get the idea out of his head. The cabs in his city were shit. Worse, since he’d been blackballed from most of the services, he had begun resorting to black car services, and had collected a laundry list of the best private drivers in San Francisco, repeatedly pinging them whenever he needed a ride for a night out. But even that was imperfect. The money, the complexity of arranging pickups, the confusion of sharing rides with friends. It was too messy. He needed the best kind of cab—one he or any of his friends could hail directly from their iPhones. He needed an ÜberCab. That became the working title—along with a few other options like “BestCab”—for the imaginary app he had designed in his head. Eventually, he’d drop the umlaut; it was too confusing for American audiences. But Camp wouldn’t let the idea go, and brought it up with nearly all of his friends, including one budding entrepreneur and angel investor, fresh off a recent company sale: Travis Kalanick.

Camp couldn’t leave out the best part. They’d market UberCab to professionals in dense cities—people like themselves—and try to make it feel exclusive, almost like a club. You’ve got to be a member to use it, guaranteeing a “respectable clientele,” and they’d only accept top-of-the-line luxury vehicles. The kind you’d want to be seen in riding around town: Mercedes, BMW, Lincoln. Best-case scenario, Camp believed, is that he created a market leader in private transportation, with the possibility of hundreds of millions in annual revenue. At worst, he’d create a small black car service for executives in San Francisco; basically, an upscale transportation service for himself and all of his friends. Even if he lost, he would win. He wasn’t subtle about pushing the idea. “Uber” replaced “great” in his vocabulary, a way to call things great. Things were “uber” this and “uber” that. That car? Uber cool. Tasty pizza for dinner? Uber slice. He wanted Uber to become something more than a German preposition, a noun synonymous with cool. Both Camp and Kalanick loved the idea. The problem was, neither Camp nor Kalanick wanted to run it. The thirty-two-year-old Kalanick was still trying to embrace his role as The Wolf, a “funding shepherd,” after years of nonstop work at Red Swoosh.

The first version of UberCab was not an app. Users logged in to a desktop computer browser, navigated to UberCab.com, requested a black car and, in theory, would receive a ride within ten minutes or less for only one and a half times the price of a yellow cab. It was more expensive, yes, but the idea was people would pay more for the reliability and convenience of on-demand service. Soon enough, the company farmed out development, and contract programmers hacked together a rudimentary version of an UberCab iPhone app. It was buggy and slow, but it worked. Camp, a sucker for luxury, focused on branding. He was fixated on maintaining a fleet of high-end black cars like Lincolns, Suburbans, and Escalades. Even the initial launch motto—“Everyone’s Private Driver”—was supposed to convey a sense of exclusivity, an upscale way to get around town. Camp believed everything about the brand should exude coolness. In the early days, that meant cold-calling hundreds of limo drivers around San Francisco and convincing them they should drive for the new service. That grunt work largely fell to Graves, who would Google black car services across San Francisco, show up to their garages, and pitch the bemused fleet staff on driving for UberCab.

For instance, often when people called for a traditional taxi, they didn’t know whether it’d be there in a matter of minutes or if it wouldn’t show up at all. When a user ordered an UberCab, she could watch the car’s journey, pixel by pixel, across the map on the screen of their iPhone. San Francisco’s aging taxicabs were grimy, their seats sticky and torn. UberCab’s private black cars would show up spotless, with slick black leather interiors and comfortable air conditioning, replete with wintergreen breath mints and chilled bottles of Aquafina. One of the most important parts of the UberCab experience was paying for the ride. Kalanick was insistent that payment was something people shouldn’t even have to think about. With UberCab, the ride would simply be charged to a credit card stored on your account. Ending the trip was as simple as opening the door and stepping out onto the curb. No tips, no change, no hassles.

Uber in two paragraphs

If your consumer-tech iPhone app doesn’t flourish in San Francisco, you might as well pack up and go home. Twenty-four-year-old Austin Geidt was tasked with figuring this out.

“We ignore it,” Kalanick repeated. “We’ll drop ‘Cab’ from our name,” he said, something his lawyers claimed gave the company greater legal exposure to false advertising claims. UberCab was now known as “Uber,” and it was staying open for business.

Now, with Uber, Kalanick was selling a winning product that was landing at an ideal time. Above all else, Kalanick was in complete control. Everything about Uber—from the design of the app to the raucous, take-no-prisoners culture—was his. He saw himself locked in an existential battle with corrupt, entrenched taxi operators and the politicians they paid to protect them. Kalanick was the general on the front lines.

“There’s been so much corruption and so much cronyism in the taxi industry and so much regulatory capture that if you ask for permission upfront for something that’s already legal, you’ll never get it,” Kalanick once told a reporter. Kalanick evidently believed there was no way Uber could win if it played by the rules—his competition certainly wouldn’t. The founder’s instinct proved correct. Uber’s guerilla tactics far outmatched the resources and technical acumen of government workers or taxi operators. In Seattle, for instance, Austin Geidt dropped in like a paratrooper, quickly hiring ground support staff to drum up interest from riders and drivers. Ryan Graves then swooped in and made the pitch to town car companies: “We’re giving your drivers a way to earn extra money.” In a matter of weeks, Uber was able to grow its ridership before the city even knew what had happened. By the time regulators had arrived, Uber was too popular with citizens to try and shut it down. Once Uber hit critical mass, transportation authorities lacked the manpower to stop the fleet. To Kalanick, Uber wasn’t doing anything wrong. After all, these were official limo and town car drivers, operating well-maintained, insured vehicles and using Uber’s service to make extra money during inefficient downtime. Everyone working for Uber was a licensed, professional driver—period. (This was before UberX allowed anyone with a car to become a driver.) As Uber’s footprint spread across the United States—Se...

Zimride focused mostly on long-distance carpooling between college campuses, something co-founder Logan Green had been obsessed with since his days at UC Santa Barbara. But despite working long hours with his partner, John Zimmer, Zimride was mired in the doldrums. Peer-to-peer sharing—the kind Sunil Paul was pursuing at Sidecar—presented an interesting opportunity. Kalanick was growing nervous. Across town at Uber’s headquarters, he had heard about Zimride’s plans, and he had heard whispers about Sunil Paul’s escapades, too. Kalanick considered Mark Zuckerberg a friend—or at least a familiar acquaintance—and the Facebook CEO had given Kalanick a heads up. Facebook employees were going crazy for Sidecar, Zuckerberg told him. Zuckerberg warned Kalanick that he might want to keep an eye on the company. Soon after, Green and Zimmer announced their pivot. Zimride would abandon its long-distance carpooling program and launch a new service called Lyft; the plan was to make casual ride-sharing a fun, friendly experience, asking passengers to ride shotgun next to their drivers and strike up friendships while joyriding to their destination. The cherry on top was a cutesy pink mustache. Lyft sent all of its drivers giant, whimsical, plush hood ornaments to affix to the front of their cars.* It was an instant hit. Kalanick sprang into action. He told his lieutenants, Ryan Graves and Austin Geidt, to take care of Lyft before it grew into a real threat. Graves, Geidt, and especially Ka...

Lyft gets serious and Uber tries to knee-cap them

Uber had discovered a winning formula to expansion. But each new city required capital, an upfront investment to kickstart what they called the demand “flywheel.” Drivers wouldn’t work for Uber unless there was enough demand from riders. And new riders wouldn’t sign up or return unless there was a critical mass of available drivers. It was a classic chicken-and-egg problem. “Uber solved that problem by straight-up buying the chicken,” Ilya Abyzov, an early Uber manager in San Francisco, told friends of the strategy. Uber began torching hundreds of thousands of dollars, giving away the money as driver subsidies. They paid bonus cash when a driver completed a certain number of rides or drove for a certain number of days. Uber would also flood the rider side of the market with cash, doling out thousands of dollars in free rides to new customers. Their theory was, if we can get people to use our service, they’ll see how amazing it is and won’t want to stop. And they were right. Once Uber hit a new city, word of mouth spread quickly; customers loved the novelty of seeing their ride wind its way towards their location on the app. People loved how shockingly cheap the (subsidized) rides were. They enjoyed not fumbling for cash, or having to tip drivers when they left the car. Uber appeared out of nowhere, and it was magical.

Uber had what was called “negative churn”—a term often used to describe software as a service, or SaaS, companies. Having negative churn meant that once customers used the product, they were more likely to keep using it regularly thereafter. “It means that customer accounts are like high-yield savings accounts,” a venture capitalist once wrote of the term. “Every month, more money comes in, without much effort.”

Taxi owners knew they had to stop Uber. In some major cities, taxi owners had paid hundreds of thousands of dollars to purchase “medallions,” taxi-service permits required by the local government. Medallions could be absurdly expensive, upwards of a million dollars in peak markets like New York City. Drivers and dispatchers took out huge mortgages to buy them. The limited number of medallions created an artificially constrained market, which meant cab drivers and taxi company owners could charge enough to earn a decent living (and pay for the medallion.) Then Uber showed up. The medallion system—a market based entirely on scarcity and exclusivity—was threatened to its core.

The taxi market explained

Taxi drivers who didn’t give in to despair, however, fought back. Some tried to beat Uber at its own game by forming taxi alliances and creating their own apps like iRide, Arro, Curb, and others. But taxi operators soon found the best way to fight back wasn’t to compete with an app. It was to protect the turf they already had. When Uber launched in a new city, taxi operators would often lean on their local transit agencies and taxi authorities, who would dispatch an official to Uber’s local headquarters. Armed with a thick rulebook and a scowl, officials in New York, Nevada, Oregon, Illinois, Pennsylvania, and other states would point out the rules and laws the company was breaking. The “Weights and Measures” book was supposed to tabulate the cost of a ride, they would say, not some complicated algorithm inside the Uber app. When that didn’t work, local legislators were known to dispatch city and state agencies to shut Uber down. If none of these things worked, there was always good old-fashioned skull cracking. Taxi cartels in areas like Las Vegas and elsewhere had deep ties to organized crime, which meant serious and sometimes violent retaliation. Cars were stolen. Sometimes taxi owners would assault drivers and set their cars aflame. In Italy, Benedetta Lucini faced pushback from local taxi thugs. As general manager of Uber’s Milan office, she worked overtime to convince Uber drivers to stay on the road, even as taxi operators would hail Ubers to their location, pull dr...

Uber made it as easy as possible for drivers to sign up. The company used a background check system that moved new recruits through the system quickly. Taxi and livery services used fingerprint testing, which offers a thorough history of a driver’s past, but often took weeks to complete. Uber used an outside firm, Hirease, which boasted an average turnaround time of “less than 36 hours.” Hirease did not require fingerprint tests. Waiting weeks for a background check was intolerable for Uber. A week was a year; a month was eternity. After perfecting the quick background check process, Uber’s political machine went to work. In states where fingerprint-based background checks were legally required, Uber hired lobbyists to get laws rewritten that mandated drivers undergo the traditional checks.

Fingerprints checks for taxis

Uber hired Ben Metcalfe, a caustic, outspoken British engineer who described his job on LinkedIn as building “custom tools to support citizen engagement across legislative matters” to drive “social good and social change.” Metcalfe and his team built automated tools that the company used to spam lawmakers and rally users. With easy, in-app buttons, users could send emails, texts, and phone calls to elected officials whenever an important legislative matter was up for debate. By 2015, more than half a million drivers and riders had signed petitions supporting the company across dozens of states. After Uber sent out a mass text message asking for support, petitions began gaining new signatures rapidly, in some cases as many as seven per second.

If you were bold enough to challenge Kalanick, you had better back up your arguments with cold, hard data. Kalanick wouldn’t listen to anything else. For years, general managers begged Kalanick to let them build a tipping function into the app so that riders could toss a few extra dollars to drivers at the end of a ride. It was a simple gesture that would earn the company significant goodwill with their driver base; besides, Lyft offered it. Yet Kalanick remained staunchly against tipping. Kalanick felt Uber worked so well because of the frictionless payment experience. A passenger could exit the vehicle without even thinking of money; adding a tipping function would require the rider to open the app again, needlessly, in Kalanick’s mind. He never understood—or never cared—how much tipping could improve Uber drivers’ livelihoods.

Eight days after the first story broke, Quentin’s team was hit with a bombshell. As scrutiny intensified in the wake of Uber’s recent scandals, an enterprising young hacker in Arizona named Joe Giron had decoded Uber’s Android application and found the list of data access permissions Uber’s app requested upon installation. The litany went far beyond what most Uber users expected: phone book, camera access, text message conversation logs, access to Wi-Fi connections. These were permissions that were suspect for any app to request, much less a taxi service. Why would a ride-hailing app need access to their customers’ text messages or camera? It was seen as a broad overreach into users’ privacy. Not only was Uber willing to go after journalists, but the company also wanted to know everything about you and your phone.

Cue hammered Kalanick from the start. “We want you to walk us through exactly what happened here, from the beginning how we ended up in this room today.” Kalanick stammered, shaken, but started from the beginning. He walked Cue and Schiller through the massive fraud across the platform, through the ingenious solutions scammers had and the problems Apple’s iOS updates had created for halting fraud. Emil Michael, the point person for dealing with Cue and the Apple blowup, had prepped Kalanick well. Kalanick was trying on a new face for this meeting, one of conciliatory regret. He knew he could get away with telling the government and city authorities to kiss his ass. However, on rare occasions, he could sense he needed to humble himself. It almost never happened. But here, at Apple HQ, in front of its top brass—he kissed the ring. “We want to hear you commit to us,” Cue said to Kalanick, as the group wrapped up the long, tense meeting. “We want to know you will never, ever do this again. Make this promise, or you’re gone, you’re out.” Cue meant business. He had brought the matter to his boss, Tim Cook, and both of them considered this a serious infraction. No one, no matter how successful the app or company, could lie to Apple and get away with it. For Cook, there was no greater sin than breaching the privacy of his users. Cook would later fight the FBI in public, refusing to unlock the smartphone of a mass murderer in San Bernardino, and would slam Facebook at public events...

there were severe safety issues. The India rape scandal was just the tip of the iceberg. Unbeknownst to outsiders, Uber operations teams dealt with thousands of misconduct cases every year, including increasing instances of sexual assault. As the service grew, millions and ultimately billions of rides were taken. The power of large numbers meant that assaults and sex crimes were probably inevitable. But Uber had so lowered the bar to become a driver that people who might have been prevented from driving in the official taxi industry could easily join Uber. The problem became so significant that later, the company would create its own taxonomy of twenty-one different classifications of sexual misconduct and assault in order to properly organize the sheer number of annual incidents reported.

Whether it was hackers in Romania running massive fraud schemes or blackmailers bilking innocent women, Joe Sullivan was good at finding people on the internet, and keeping people safe. It was the reason he had been recruited to Uber. And it was why Sullivan ultimately said yes to the job. He looked at Uber and saw a rat’s nest of problems: widespread fraud, competitors across four continents, hackers laying siege to the company’s valuable stockpile of personal information. Plus, Uber offered him the chance to be more than an internet cop; the very nature of Uber’s service meant dealing with things that can go wrong in the physical world, with millions of Uber riders in actual cars every single day.

Larry Page—a transportation obsessive—had invested more than a billion dollars and tens of thousands of employee hours into the problem by the time he and Sergey felt comfortable enough to show their egg-shaped car to the world. No one was more determined to bring robot cars to life than Larry Page. No one except, perhaps, for Anthony Levandowski. The lanky, cantankerous engineer was still working on “Project Chauffeur,” the company’s pet name for autonomous vehicle research. But his position was growing tenuous. For one, Levandowski was a poor leader. He would get in constant fights with colleagues over the speed—or lack thereof—at which Google was willing to work on the self-driving project. But Page liked the fact that Levandowski didn’t always play by the rules. Men like Levandowski, Page believed, would bring Google to the next phase of autonomous vehicle research.

personal blog, susanjfowler.com. The entry clocked in at more than three thousand words, the length of a magazine article. She was nervous when she scanned the title: “Reflecting On One Very, Very Strange Year At Uber.” Would anyone actually read this? Would anyone actually care? “It’s a strange, fascinating, and slightly horrifying story that deserves to be told while it is still fresh in my mind,” Susan Fowler wrote in the introductory paragraph of her blog post. “So here we go.”

His thinking on keeping his seat on the council didn’t last long. In the span of a week, more than 500,000 people deleted their Uber accounts entirely, not counting the incalculable others who simply deleted the app from their phones. Uber’s all-important ridership growth curves—for years always hockey-sticking up and to the right—started turning downward. Kalanick began to sweat. Lyft, at that point running out of money and on the verge of surrender, benefitted enormously from the backlash. People began to ditch Uber and switch over to Lyft. (Protest felt good, but people still needed to be able to call a car sometimes.) Lyft’s executives then pulled a well-executed PR stunt, publicly donating $1 million to the American Civil Liberties Union over four years, making themselves look like white knights while Uber was groveling before Trump. The resultant surge in ridership brought Lyft back from the brink of failure. At last showing positive signs of growth, Lyft soon attracted investment from Kohlberg Kravis Roberts, the private equity firm, buoying the ride-hailing company with more than a half-billion dollars in additional capital. Lyft’s fundraising sunk Kalanick’s spirits. He had spent the entire summer trying, and failing, to defeat his largest competitor in China. And now, just as the new year began, his chance to kill his strongest American opponent had slipped away as well. He was so close to rubbing John Zimmer’s nose in defeat. No longer.

How Lyft survived

Susan Fowler gave one last look at the words on the screen. “Reflecting On One Very, Very Strange Year At Uber,” the title of the post read. She took a breath.

Travis Kalanick woke up to an iPhone on nuclear meltdown. Within hours, the link to Susan Fowler’s blog post had been shared internally, across private messages and chat rooms hundreds of times. Uber employees were buzzing with ire, excitement, confusion. It was raining in San Francisco that Sunday morning, but Kalanick was in Los Angeles. Groggy, he began returning the flood of calls that had come in from Uber’s top executives about Fowler’s whistleblowing memo. Fowler had never ranked high enough in the company to cross his radar. And yet this one woman—a single engineer in Uber’s sprawling workforce—was rattling the entire organization. Press calls began flooding into the public relations department, seeking comment on Fowler’s post. Fowler herself had gone dark, leaving reporters’ calls unanswered, saying nothing beyond what she had written on her blog.

Whereas over the course of 2014 through 2016, Uber was hiring thousands of Google employees away, now Google began rehiring Uber’s conscience-stricken workforce in droves; Airbnb, Facebook, even Lyft started to pick off Uber employees. Uber needed to fix its morale problem. Fowler’s blog post had only made it worse.

Rachel Whetstone, Kalanick’s senior vice president of communications and public policy, was nervous. She was an operator, a longtime communications and policy executive who had worked for Google for nearly a decade, rising to the top of the comms food chain, before coming to Uber. Thin and anxious, with wisps of long, strawberry blonde hair and a posh British accent, Whetstone came from the cutthroat world of Conservative British politics before diving headlong into the tech sector. She was a natural strategist, had a knack for seeing around corners, figuring out where the press was going to strike next, and bracing for impact. She earned her seat at the table by discussing long-term policy decisions with executives as a peer, not a subordinate. After kicking upstairs David Plouffe—who was better suited to schmoozing politicians and composing speeches than running a daily press shop—Kalanick promoted Whetstone to take his place.

My reporter trick is to play dumb and friendly; dumb and friendly is always more approachable than eager and prodding.

It didn’t matter to Kalanick that drivers were logging more trips and picking up more people—basically doing twice the work—to make the same amount of money. It didn’t matter that drivers were commuting absurd distances to busy cities like San Francisco—often from places two hours away, but occasionally as many as six hours away—sleeping in their cars overnight on side streets and empty parking lots for the chance at more rides per hour. It didn’t matter that San Francisco lacked sufficient public bathrooms for drivers, forcing them to find coffee shop bathrooms, or, more often, make do elsewhere. And it certainly didn’t matter that drivers pulling dayslong shifts were overworked and under-slept. Kalanick had no sympathy for drivers and their bills—vehicle wear and tear, medical insurance, among many others—and classified them all as 1099 freelance workers. The entire business model was based on Uber minimizing the company’s responsibility over its drivers.

Uber business model

“I wanted to make a few comments just to put all of this in perspective,” Gurley began, his towering frame always at odds onstage with the awkwardness of his personality. “This company is undoubtedly the most successful startup in the history of Silicon Valley. It grew faster, bigger, it touched more people customers, countries cities faster than ever before. “But I want to bring up a phrase you hear pretty often but I think is applicable,” Gurley continued, his tone turning grave. “With great success comes great responsibility. We are no longer considered a startup by the outside world. We are considered one of the largest, most important companies in the world. And our behavior, our corporate behavior, has to begin to equal and parallel that expectation or we’re gonna continue to have problems.”

Khosrowshahi’s first job was to repair relationships with its hundreds of thousands of regular drivers after years of abuse and neglect. By the time Khosrowshahi was voted in, Uber was halfway through its “180 days of change” campaign to improve relations. Led by two executives from Kalanick’s reign—Rachel Holt and Aaron Schildkrout—the campaign involved an extended listening tour and apology, as well as new features and improvements drivers had been requesting for years. One of the most meaningful changes was something Kalanick had personally prevented: the ability to tip drivers. After Kalanick was ousted, the feature was implemented, earning the company an enormous amount of goodwill.

For the first time in its nine-year history, Uber had installed proper corporate governance—mechanisms and officers that Bill Gurley had long desired.

Uber’s self-driving division, one of the biggest drains on Uber’s finances and once considered an “existential” area of development for the company, is in limbo at the time of this writing.

Everyone has a motivation to speak with a reporter, but many of my best sources felt they were doing the right thing by coming forward and telling their story in hopes it would help people to better understand the story of Uber. I want to express my thanks to all of you here: I truly could not have done it without you.