by Isaac, Mike
After some time around celebrities, Kalanick mused with Michael about how they needed a “big star” to join Uber’s board of directors. A hot startup, they believed, needed a heavy hitter to turn heads in Hollywood.
Oprah Winfrey was the prize. Kalanick met Winfrey in Ibiza and became fixated on the idea of her becoming a board member. Everyone in Silicon Valley wanted Oprah on their board. She was a self-made, entrepreneurial black woman with millions of adoring followers and a global empire. Many sought access via Gayle King, the CBS This Morning co-host, and Whitney’s longtime friend. But few had made any progress. Pishevar tried to throw a dinner for King to soften her up. Kalanick dispatched Gabi Holzwarth to sweet-talk her. They pulled out all the stops, but King didn’t bite, and Oprah was never really interested.
Kalanick did better with Shawn Carter, also known as the hip-hop mogul Jay-Z. Carter was an early investor in Uber, as was his wife, Beyoncé Knowles. Carter and Knowles had the foresight to know Uber was going to be big. During one venture capital round, Carter once wired more money to Uber’s bank account than he was supposed to, an attempt to increase his equity stake. Kalanick and Michael, together during the moment, were thrilled at the idea of rebuffing the “Big Pimpin’ ” star Jay-Z. They let Carter down gently, and wired some of the money back, saying they already had too many interested investors.
Parties at strip clubs became regular occurrences, often expensed on the company’s corporate account. A few execs would usually bill the evening as client entertainment, or business development—and one or two other executives would sign off on it, as was the case for an incident in South Korea in 2014, something that would come back to haunt the company later. They had a pet phrase to describe expensing strip clubs to the corporate card: “Tits on Travis.”
The tone of Uber’s culture was being set from the top. Kalanick knew what he wanted in his employees—who were mostly white, male, and in their twenties—and made his hiring decisions based on that instinct. The result was a workforce that largely reflected Kalanick himself.
Every global office was unique. Kalanick wanted to empower his workers—“let builders build,” according to the Uber company value—and urged employees to be responsible for their own fiefdoms. Yet still, because Uber had hired thousands of Kalanick clones, many satellite offices had flickers of similarity.
Southeast Asia, for instance, was a hotbed of partying for Uber operations employees and managers. Cocaine and booze were common, as was harassment—and even worse.
One female employee in Uber’s Malaysian office was heading home from work one evening in 2015, when she noticed a group of men following her. It was a local gang, she realized, and began frantically texting people for help. One of those people was her boss, the local Uber general manager. She said that she needed help, and that she was scared she was going to be raped.
As her ride home continued, her manager responded: “Don’t worry, Uber has great health care,” he texted. “We will pay for your medical bills.”
The Thailand office at the time was perhaps even worse, a toxic workplace where drug use and visits from sex workers were not unheard of. No one from Uber kept the behavior in check.
One particularly raucous evening, a bunch of Uber Thailand employees were up late drinking and snorting coke, a semiregular occurrence at that office. One female Uber employee with the group had decided she didn’t want to do drugs with her colleagues, and tried to abstain. Before she could leave, her manager grabbed the woman and shook her, bruising her. Then he grabbed the back of her head and shoved her face-first into the pile of cocaine on the table, forcing her to snort the drugs in front of them.
The New York office was largely defined by its machismo, sexism, and aggression. São Paolo saw angry managers throwing coffee cups across the room or screaming at employees when they weren’t happy with results. It wasn’t unheard of for managers to sleep with subordinates.
These dark events rarely led to consequences for management, and other employees—if they knew about the wrongdoing—either ignored the problems or squashed their concerns. But for many, the drawbacks did not outweigh the excitement. Even if they had to white-knuckle it through bad times, there was a pervasive feeling that Uber, the world’s preeminent ride-hailing service, would soon become a global behemoth on the order of Google, Amazon, or Apple. Uber had billions in the bank, was poaching top talent from companies across the Valley, and had its sights set on conquering international markets. When employees’ restricted shares vested, they would earn an absurdly sweet payday.
Kalanick’s fortieth brithday was a bash he wouldn’t forget—a multi-yacht party in the Aegean sea featuring top shelf booze and a group of models flown in for good measure. By the end of 2016, life was good for Travis Kalanick. He was rich and powerful, and his empire was growing further by the day.
As 2017 began, a young woman was just beginning her job at Stripe, a payments startup based in San Francisco. It had been two months since she had left her job at Uber, and she hadn’t told anyone in much detail why she departed such a hot startup. Every time she reflected on her year at Uber she felt disgust, sadness, anger. Working for Uber wasn’t anything like she thought it would be.
Friends and family wouldn’t stop asking her why she left, but she had never found the words. By February, however, she had managed to take stock of her experience, and began to describe her time at Uber in a post on her 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.”
Chapter 19 notes
****** Billionaire on paper, that is. Kalanick was still living off money he made from the sale of Red Swoosh. He didn’t sell a single share of Uber stock during the entire time he ran the company.
†††††† One founder, Oren Michels, cut Kalanick a check for $5,000 early on in Uber’s history. By the end of 2017, that $5,000 had multiplied in value 3,300 times, worth somewhere close to $20 million. Mr. Michels made more off his $5,000 Uber investment than he did when Intel purchased his entire startup in 2013.
PART Ⅳ
Chapter 20
THREE MONTHS PRIOR
Three and a half months before Susan Fowler hit “publish” on her blog post, the tech world had been thrown for a loop.
Since the dot-com crash of the early 2000s, and certainly throughout the smartphone era, the press had largely flattered the American technology sector. Headlines in the Wall Street Journal, the New York Times, and other major publications admired the progress achieved by tech’s boy geniuses. Mark Zuckerberg was a visionary whose social network connected friends and family worldwide. Twitter had enabled democracy to flourish in the Middle East. Google wunderkinds had built beautiful maps that made life easier, and given everyone a free email account. Elon Musk’s ambitions were transcendent: he would save the world with electric Teslas and conquer the stars with SpaceX.
Though many had written about the negative aspects of tech, the American press and public often overlooked Facebook’s towering monopoly on social media, Amazon’s takeover of internet infrastructure, the disappearance of privacy enabled by Google’s advertising technology, the noxious, racist trolls enabled by Twitter, and the outlandish and harmful theories fed to users by YouTube’s automated algorithms—the earth is flat, vaccinations cause autism, 9/11 was an inside job. That generous view of technology would curdle on the night of November 8, 2016, when Donald Trump unexpectedly won the US presidential election.
But while the election cast a pall over tech in general, the night also served as the turning point for Uber in particular
. The company’s troubles did not stem from the election, of course, nor did they cause the result, but they were soon caught up in the chaos that followed. The maelstrom marked the beginning of one of the worst twelve-month periods in American corporate history.
When the tech workers awoke on the morning after the election, their mental image of themselves—as bastions of youth and democratic idealism, helping to create a more efficient, healthier, more connected country—had been shattered.
Donald John Trump was the president of the United States. The thrice-married real estate mogul who spent the last decade taking birther-conspiracy potshots at Barack Obama on Twitter was now the commander in chief. Silicon Valley had donated millions to the Clinton campaign; techies were eyeing jobs in the Clinton administration.
Now the public was pointing fingers. 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.
“The most obvious way in which Facebook enabled a Trump victory has been its inability (or refusal) to address the problem of hoax or fake news,” a report from New York magazine claimed. The headline expressed the creeping sentiment that “Donald Trump Won Because of Facebook.” That doubt and worry began spilling over into the minds of tech workers, too. Even inside of Facebook, the most zealous of the true believers began to question the world-shaping power of the platform they had built.
Twitter, too, came in for condemnation. They had given a platform to a billionaire troll, which he leveraged into maximum, round-the-clock exposure. Trump had banked more than $2 billion in “earned media,” that is, free attention—far surpassing that of any other candidate. Now, each tweet was a presidential proclamation.
Where once the public and media had adored Big Tech—Facebook and Twitter gave people a voice, while Uber and Lyft gave anyone a ride—now the public devoured stories of state-sponsored hackers using vast databases of personal information to influence the election. Suddenly, nefarious forces in Silicon Valley had led the country off a cliff, and Big Tech was profiting from the strife.
Travis Kalanick had spent the past two years steeling Uber for a Clinton presidency.
He spun up teams of lobbyists in every market that mattered. He wanted them ready to deal with an incoming administration that was a friend to unions and an enemy to companies that relied on contract workers. Clinton hadn’t come after Big Tech quite yet; she was closely tied to major donors in the Valley, including Facebook’s Sheryl Sandberg, John Doerr of Kleiner Perkins, and Marc Benioff of Salesforce. But if there was a company a Clinton presidency might come after, it could be the most hated startup in the country: Uber.
But Trump’s upset victory caught everyone at Uber off guard. Most of the rank and file, a largely Democratic- and Libertarian-leaning force, were tearing their hair out at the thought of a Trump presidency. (Even many of the Republicans of Uber’s ranks found the idea ludicrous.) Thuan Pham, Uber’s chief technical officer, wrote an internal letter blasting Trump’s election as “a huge step backward,” calling the new president an “ignoramus” and comparing his win to the ascendancy of ruthless dictators like Chairman Mao Zedong in China.
But as Trump’s victory became inevitable on election night, Travis Kalanick was beginning to see the silver lining. A Republican administration was less likely to come after Uber, especially if he positioned his company as one of the largest job-creating startups in history. Anyone who owned a car could be put to work, and Kalanick could take credit for that. Perhaps the next four years wouldn’t be so bad.
Besides, he had enough headaches to deal with. After two years and billions of dollars in losses and fraud, Kalanick’s investors demanded he abandon China. No American tech company had been able to crack the country, and Uber wasn’t going to be the first. Despite Kalanick’s efforts, the Chinese government had chosen to support DiDi, a Chinese company, and remained hostile to Uber.
Kalanick was loath to concede. He had hoped to twist the knife; the Strategic Services Group attempted to photograph Jean Liu, the president of DiDi, when the New York Times pushed out the news of Uber’s $3.5-billion funding round from the Saudis.
But while Kalanick may have had the stomach for a further battle, his backers did not.
Bill Gurley, the “Chicken Little” of Uber’s board, was chafing at the burn rate in China. Another of Kalanick’s antagonists on the board, David Bonderman, was starting to make noise, too. Kalanick brought on Bonderman, a giant of private equity at TPG Capital, back during a funding round in 2013. But now Bonderman was criticizing the way Kalanick was funding the losing fight in China.
Some of Uber’s institutional shareholders held calls with DiDi’s biggest investors about settling the conflict. Kalanick was pissed, yet unsurprised; investors, he had maintained, will always screw you in the end. On August 1, Uber conceded the fight; DiDi would take over Uber’s business, and Uber would suspend operations in China.
For investors, it was a win. No more enormous cash drain, no squandering the profits from booming markets. And to sweeten the deal, Uber received a 17.7 percent equity stake in DiDi, something that would grow in value and could prove immensely lucrative when DiDi decided to go public. Emil Michael negotiated the deal hard, and considered it one of his crowning achievements at the company. But for Kalanick, the defeat was more bitter than sweet. He would not outdo Page, or Dorsey, or even Zuckerberg and become the first American tech CEO to conquer the Chinese market.
He had something else on his mind. With Trump as the victor, a business-friendly Republican administration might end the vilification of tech and cut labor and transportation regulations. But they would need to act fast. President-elect Trump had already began putting together a handful of policy councils stacked with some of tech’s biggest leaders, and Travis wanted to be on it. He and his team pulled strings to make sure he had a seat at the table. One month after the election, top tech CEOs were called to attend a technology summit with Trump during the transition. Kalanick was stuck in India and missed the photo opportunity, but a direct line to Trump was something Kalanick was happy to have.
His employees disagreed. Grumbles traveled the hallways of 1455 Market Street, as many Uber employees wondered why their boss needed to embrace a man they considered xenophobic, ignorant, and racist. At internal all-hands meetings, they urged their boss to reconsider and step away from the council.
Kalanick defended his decision, figuring it was better to have a seat at the table than not have one at all. He could manage a little frustration in the ranks.
Chapter 21
#DELETEUBER
As Travis fought his way onto the Trump business advisory council, a Chicago tech worker named Dan O’Sullivan still believed Donald Trump was full of shit.
The president spent his entire first week arguing with the press over the size of his inauguration crowd. (“The biggest ever inauguration audience!” Trump’s press office announced, an obviously false statement.) Trump was a buffoon, O’Sullivan thought, an idiot foisted upon the office by an electorate poisoned by Fox News. By the time he left office, O’Sullivan prayed, Trump would be thwarted by his advisors and accomplish little of what he promised on the stump in 2016.
The Long Island–born son of a nurse and an Irish telephone lineman, Dan O’Sullivan grew up worlds away from Trump’s gold-plated tower in Manhattan. He was proud of his blue-collar background. His great-great-uncle, Mike Quill, co-founded the Transport Workers Union in New York City back in 1934. Quill’s ties to the Communist Party earned him the nickname “Red Mike.” On the night of his sister’s birth, O’Sullivan’s f
ather was out on strike with fellow linemen in the Communication Workers Union.
After kicking around schools in Long Island and Maine, Dan O’Sullivan landed in Chicago, a place he liked though knew little about. At six-foot-three and pushing 220 pounds, O’Sullivan looked like a different kind of lineman—more Chicago Bear than Bell Atlantic like his father. He picked up a Chicago accent quickly, cutting short his “U’s” and “A’s.” His nasally vowels gave many the mistaken impression he was a native Chicagoan.
O’Sullivan dreamed of being a writer, and started freelancing political pieces for Gawker, Jacobin, and other left-leaning outlets. To pay the bills, he landed in a call center at a tech company, a lower-level peon answering angry customer support questions. The work was depressing, but he spent his off-hours pursuing his passion, hustling for opportunities to write.
More vivid than his dreary call center job was O’Sullivan’s digital life on Twitter. He mostly used it to follow political accounts and news and to connect with other writers. He started chatting with other leftists and joking around with people who began as anonymous avatars in his Twitter feed, then slowly grew to become his online friends. Even as Dan despaired at Trump’s popularity and success, at least he could make fun of Trump’s buffoonery with his friends on Twitter.
O’Sullivan cherished his digital anonymity. He was opinionated and crass on Twitter, and knew his obscenities towards Trump might not please his employer. And if he had to find a new job, some of the esoteric, vulgar in-jokes he shared with Twitter friends wouldn’t thrill a recruiter.
Still, Twitter was worth it. He chose a handle for himself, a pun his online friends could remember him by: @Bro_Pair.
The order came as night fell on Friday, January 27, a week after Trump took the oath of office. Effective immediately, Trump was closing the nation’s borders. Singling out predominantly Muslim countries, he barred refugees from places like Syria, which was in the midst of a violent civil war that was driving thousands to seek asylum from potential slaughter.