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“This is not about whether we should have a thoughtful conversation about changing taxi regulations. This is about one company thinking it is above the law.”
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.
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.
Someone from Uber headquarters would travel to a new city and hire a local “general manager”—usually a fired-up twentysomething, or perhaps someone with a scrappy, startup mentality. That manager would spend weeks flooding Craigslist with want ads for drivers, enticing them with sign-up bonuses and thousands of dollars in cash for hitting milestones.
Uber only expected that new field operations staff have ambition, the capacity to work twelve- to fourteen-hour days, and a willingness to evade the rules—even laws—when necessary.
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.
Concepts like “breaking the law” weren’t applicable, they believed, when the laws were bullshit in the first place.
The saga of Uber—which is, essentially, the story of Travis Kalanick—is a tale of hubris and excess set against a technological revolution, with billions of dollars and the future of transportation at stake.
But most of all, it is a story about how blind worship of startup founders can go wildly wrong, and a cautionary tale that ends in spectacular disaster.
The pervasive trope of the “tech bro” was the ire of communications representatives across the Valley; young and moneyed, childless, these engineers and salesmen were unburdened by the daily concerns of the baristas, housekeepers, and wait staff they felt existed to serve them. A tech bro’s greatest worry was whether or not he was working at that year’s hottest “unicorn”—a noun coined in 2013 by a venture capitalist who used it to describe companies valued at more than $1 billion. By the fall of 2015, Uber was the unicorn to end all unicorns; every tech bro had to be there.
At the end of the week, Uber’s finance team added it all up. The entire “X to the x” celebration cost Uber more than $25 million in cash—more than twice the amount of Uber’s Series A round of venture capital funding.
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 “gig economy” unleashed by companies like Uber, Instacart, TaskRabbit, and DoorDash spurred an entirely new class of workers—the blue-collar techno-laborer.
With the rise of Facebook, Google, Instagram, and Snapchat, venture capitalists looked everywhere to fund the next Mark Zuckerberg, Larry Page, or Evan Spiegel—the newest brilliant mind who sought, in the words of Steve Jobs, to “make a dent in the universe.”
the “cult of the founder” meant celebrating the vision of the founder no matter what, a slavish devotion to the CEO of a company simply because he was the CEO.
Twelve-hour workdays and a nonexistent social life became things to be celebrated, the markers of a “hustle culture” that the tech bro founders embodied.
Many believed the founders were remaking the world, making it smarter, more logical, meritocratic, efficient, and beautiful—delivering a new and much improved version: an upgrade on life. This was the height of tech utopianism.
the fourteen core leadership principles posted to Amazon’s website: Customer Obsession Ownership Invent and Simplify Are Right, A Lot Learn and Be Curious Hire and Develop the Best Insist on the Highest Standards Think Big Bias for Action Frugality Earn Trust Dive Deep Have Backbone; Disagree and Commit Deliver Results
“Super pumpedness is all about moving the team forward, working long hours—pretty much a do-whatever-it-takes attitude to move the company in the right direction,”
“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.
Crucially, AWS was relatively inexpensive. For the first time in computing history, any single programmer with a startup idea and a bit of cash could quickly build a company without having to plow tons of money into infrastructure—they could farm that part out to Amazon, and focus on building the app itself.
Throughout his career Gurley had been enamored with what he called “marketplaces,” a category of business that neither made new products nor sold others, but merely matched the desires of one side of a market with the products of the other side, and took a cut as the middleman.
The most vaunted title in Silicon Valley is, has been, and ever will be “founder.”
Founders like him spent every day hustling to keep their companies running. They put their reputations, finances, and well-being on the line. Venture capitalists, on the other hand, only risked OPM—“other people’s money.”
Uber’s guerilla tactics far outmatched the resources and technical acumen of government workers or taxi operators.
Uber had perfected viral growth.
But as one Uber employee competing with Lyft at the time said, “The law isn’t what is written. It’s what is enforced.”
Doug Schifter, a livery driver from Manhattan, faced financial ruin after the rise of Uber wrecked his income driving for traditional car services. Schifter drove to City Hall in Lower Manhattan on a cold Monday morning in February 2018, put a shotgun to his head, and pulled the trigger.
Travis Kalanick couldn’t figure out why everyone hated his guts. Feelings had no place in the business world. Being cutthroat was a quality to be celebrated, not hidden, in a CEO. When it came to describing an executive, “pugnacious” was never meant to be an insult.
A unicorn earned the name by being unspeakably rare. Practically overnight, dozens of consumer startups had been valued well into the billions, many with little revenue to speak of. A hundred unicorns suggested to Gurley that some would turn out to be ponies with papier-mâché horns. “I do think you’ll see some dead unicorns this year,” he told Gladwell.
If Silicon Valley was defined by “the crazy ones, the misfits, the rebels and the troublemakers,” a rising countercultural force of hackers and techno-revolutionaries described in Apple’s “Think Different” advertising campaign, then the post-recession era of the Valley was shaped by a different force: the rise of the MBA grads.
Even during recruiting, prospective employees were treated poorly. The company had designed an algorithm that determined the lowest possible salary a candidate might accept before making an offer to them, a ruthlessly efficient technique that saved Uber millions of dollars in equity grants.
As Uber bled cash by the bucketful in China, Kalanick was breathing down his engineers’ necks to solve the problem. It was a recurring theme at Uber: something went wrong, the boss wanted it taken care of, and he didn’t much care how you got it done. Just get it done.
Apple’s long-espoused principles, specifically an individual’s right to privacy. Steve Jobs had valued consumer privacy, but his successor, Tim Cook, was a fanatic. He believed Apple’s users should have complete control of their private digital lives. And if an Apple customer decided to wipe their iPhone clean of data, no one else—individuals, family members, companies, law enforcement—should be able to find a trace of that data on the device afterwards. Wiping an iPhone was final; the data was gone.
Facebook, Google, Twitter, Reddit, and Instagram had won Trump the election. Cambridge Analytica had manipulated social media—Facebook embedded its own employees in the Trump campaign. Tech had gone from the youth-led leveling force that had brought Obama to the White House to a nefarious, psychological propaganda machine. The public suddenly realized the scope and targeting power of Google’s and Facebook’s advertising engines. Members of Congress, sensing unrest, began singling out the tech companies. So did the media.
