Uber’s C.E.O. Plays With Fire

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UberCab, as it was called at the time, started its service in San Francisco in May 2010. Mr. Camp and Mr. Kalanick picked that name to emphasize the convenience of calling a car on demand from an app. Mr. Kalanick wanted a break from full-time start-up life after running Red Swoosh, so he and Mr. Camp named Ryan Graves, who responded to a call for help on Twitter, as chief executive.

A few months later, Mr. Kalanick changed his mind and took over as UberCab’s chief. He quickly positioned the start-up as an alternative to the taxi industry. At the time, taxi companies had iron grips in many towns. City-by-city regulations required procedures like base stations for cabs, safety measures and other stipulations.

Mr. Kalanick ignored those rules.

“We’re in a political campaign,” he once said at a technology conference, and the candidate is Uber. The opponent is named Taxi, he said, adding a rude descriptive. “Nobody likes him, he’s not a nice character, but he’s so woven into the political machinery and fabric that a lot of people owe him favors.”

Mr. Kalanick carried that same level of intensity into Uber’s headquarters, pacing briskly while working by doing laps around the office. His pacing is so legendary, his father once said, that he wore a hole in the carpeting.

Mr. Kalanick focused on expanding UberCab quickly. The company typically sent a small strike team into a new city — say, Seattle — to aggressively recruit new drivers through Craigslist and other online listings. Then the team marketed UberCab’s app to increase ridership.

That drew attention from regulators. In October 2010, the company shortened its name to Uber after receiving a cease-and-desist letter from San Francisco officials for marketing itself as a taxi company without the proper licenses and permits.

To influence local legislators to accept Uber, Mr. Kalanick took extra steps. In 2014, Uber hired Ben Metcalfe, an 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.”

In practice, Mr. Metcalfe and his team created an email-based system to aid Uber users and drivers to directly contact local legislators to lobby for allowing Uber in their cities. The system was similar to Change.org, a website that pushes social change through online petitions. City and state officials were soon deluged with emails supporting Uber.

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Taxi drivers and others who supported Mr. de Blasio’s efforts to halt Uber’s expansion rallying outside City Hall in Manhattan in 2015. Credit Hiroko Masuike/The New York Times

In some places, Uber employees were also told to create computer programs known as scripts that would automatically vote for the ride-hailing service in city-administered surveys.

Such tactics were effective. In 2015 when New York’s mayor, Bill de Blasio, tried capping the number of Uber cars, Uber added a “de Blasio” tab in its app to show lengthy waiting times for rides if legislation against Uber was allowed to go forward. People could easily send a form email to the mayor and the City Council supporting Uber by pressing a button in the app.

Mr. de Blasio capitulated, and the cap did not take place.

Taking Center Stage

As Uber gained momentum, Mr. Kalanick moved into the spotlight.

It did not come naturally. One friend recalled a night out with a group of married couples at the Gold Club, a San Francisco strip club, a few years ago. Mr. Kalanick, who was single, pulled out a laptop to work on a spreadsheet, crunching Uber’s numbers while friends watched the dancers onstage.

Another friend called Mr. Kalanick a “tech world rock star,” which means something different in Silicon Valley than in the music world.

“To work with and around one requires a different kind of mentality and skill,” said Andy Abramson, an early adviser to Mr. Kalanick. Mr. Abramson likened the chief executive to other idiosyncratic founders like Jeff Bezos of Amazon.

Mr. Kalanick was eventually coaxed more into the limelight by others. Shervin Pishevar, an Uber investor, sometimes took Mr. Kalanick to clubs in Los Angeles on the weekend, providing a car and a change of “club clothes.” Mr. Pishevar, who did not respond to a request for comment, was the Uber chief’s entryway into Los Angeles’s world of celebrity.

Hollywood stars were eager to buy into Uber, which they had started using to get around. Actors like Edward Norton, Olivia Munn and Sophia Bush took small stakes in the company. Mr. Kalanick and a top lieutenant, Emil Michael, sometimes hung out with Leonardo DiCaprio, who is also an investor, and Jay Z, whose wife, Beyoncé, performed for Uber employees at a poolside party in Las Vegas in 2015.

Jay Z once wired money to Mr. Michael in an attempt to invest even more in Uber. Mr. Michael and Mr. Kalanick, giddy at rebuffing a celebrity, wired some of the money back, saying they already had too many interested investors. Representatives for Jay Z did not respond to requests for comment.

Mr. Kalanick also dreamed of luring celebrities into advisory roles at Uber. One aim was persuading Oprah Winfrey to join the board — something Uber executives believed could happen after Mr. Kalanick met Ms. Winfrey at a party on the Spanish island of Ibiza — but the idea never jelled. A spokeswoman for Ms. Winfrey declined to comment.

Mr. Kalanick began mixing with elite business executives. He developed a close relationship with Mr. Cohn, then a top-ranking executive at Goldman Sachs. At one point, the two men spoke on a near daily basis. Mr. Cohn and a White House spokeswoman did not return requests for comment.

Leadership Principles

Inside Uber, Mr. Kalanick began codifying the pillars of the company’s culture. He particularly admired Amazon, the e-commerce company that espouses 14 leadership principles including “learn and be curious” and “insist on the highest standards.” So he created 14 values for Uber, with tenets such as being “super pumped” and “always be hustlin’.”

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Uber employees in San Francisco. The company, which has set growth as its main goal, has suffered a series of setbacks in recent months. Credit Ryan Young for The New York Times

Some employees admired Mr. Kalanick’s deep involvement in Uber. “TK was hands-on and in the product weeds,” said Chris Messina, who left Uber in January, using Mr. Kalanick’s nickname. “He cared deeply about the product and the people building it.”

Mr. Kalanick’s main mantra was “growth above all else.”

That meant Uber’s top performers were often promoted and protected. When one general manager, a title for a city-level chief, threw a coffee mug at a subordinate in a fit of rage, the incident was reported to human resources — but there was no follow-up. At the time, Uber’s business in the general manager’s city was strong.

Other complaints also fell on deaf ears.

After a backlash over Uber’s use of “surge pricing” (raising ride prices when demand is high) amid an East Coast snowstorm in 2013, Mr. Kalanick’s response to upset riders was a torrent of economics and math.

“We did more trips because of our approach, not fewer,” he said in an interview with Wired at the time. “We gave people more options to get around, and that is the whole frickin’ goal.”

Friends and employees told Mr. Kalanick that he should at least pretend to care about how it looked to take such a hostile stance with Uber’s users. Several described him as “emotionally unintelligent.”

Mr. Kalanick made other missteps. In 2014, he and his then-girlfriend, Gabi Holzwarth, went out in South Korea with Mr. Michael and other Uber employees to drink and sing karaoke. The establishment was an escort bar, where customers may pay for the company of women, and some members of the party picked out dates for the evening. The incident, reported by The Information, resulted in a human resources complaint from an employee who attended.

The same year, Mr. Kalanick discussed how Uber had boosted his desirability with women in an interview with GQ, calling the company “boob-er.”

And just days after a former employee published a blog post in February detailing sexual harassment at Uber, Mr. Kalanick attended Vanity Fair’s Academy Awards party in Hollywood, stunning some colleagues with his perceived insensitivity.

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Mr. Kalanick at Vanity Fair’s Oscars party in February. Credit Danny Moloshok/Reuters

His desire for growth also knew few limits. Uber plunged into China in 2013, and Mr. Kalanick spent billions of dollars to outgun the local incumbent Didi Chuxing — only to have to retreat last year, partly because of heavy losses. Mr. Kalanick is now spending heavily in India to win there, even offering to become an Indian citizen if it will help Uber’s prospects. The company has said that it lost $2.8 billion in 2016, excluding China.

For the Win

With Mr. Kalanick setting the tone at Uber, employees acted to ensure the ride-hailing service would win no matter what.

They spent much of their energy one-upping rivals like Lyft. Uber devoted teams to so-called competitive intelligence, purchasing data from an analytics service called Slice Intelligence. Using an email digest service it owns named Unroll.me, Slice collected its customers’ emailed Lyft receipts from their inboxes and sold the anonymized data to Uber. Uber used the data as a proxy for the health of Lyft’s business. (Lyft, too, operates a competitive intelligence team.)

Slice confirmed that it sells anonymized data (meaning that customers’ names are not attached) based on ride receipts from Uber and Lyft, but declined to disclose who buys the information.

Uber also tried to win over Lyft’s drivers. Uber’s “driver satisfaction rating,” an internal metric, has dropped since February 2016, and roughly a quarter of its drivers turn over on average every three months. According to an internal slide deck on driver income levels viewed by The New York Times, Uber considered Lyft and McDonald’s its main competition for attracting new drivers.

To frustrate Lyft drivers, Uber dispatched some employees to order and cancel Lyft rides en masse. Others hailed Lyfts and spent the rides persuading drivers to switch to Uber full time.

After Mr. Kalanick heard that Lyft was working on a car-pooling feature, Uber created and started its own car-pooling option, UberPool, in 2014, two days before Lyft unveiled its project.

That year, Uber came close to buying Lyft. At a meeting at Mr. Kalanick’s house, and over cartons of Chinese food, he and Mr. Michael hosted Lyft’s president, John Zimmer, who asked for 15 percent of Uber in exchange for selling Lyft. Over the next hour, Mr. Kalanick and Mr. Michael repeatedly laughed at Mr. Zimmer’s audacious request. No deal was reached. Lyft declined to comment.

The rivalry remains in force. In 2016, Uber held a summit meeting in Mexico City for some top managers, where it distributed a playbook on how to cut into Lyft’s business and had sessions on how to damage its competitor.

To develop its own business, Uber sidestepped the authorities. Some employees started using a tool called Greyball to deceive officials trying to shut down Uber’s service. The tool, developed to aid driver safety and to trick fraudsters, essentially showed a fake version of Uber’s app to some people to disguise the locations of cars and drivers. It soon became a way for Uber drivers to evade capture by law enforcement in places where the service was deemed illegal.

After The Times reported on Greyball in March, Uber said it would prohibit employees from using the tool against law enforcement.

The idea of fooling Apple, the main distributor of Uber’s app, began in 2014.

At the time, Uber was dealing with widespread account fraud in places like China, where tricksters bought stolen iPhones that were erased and resold. Some Uber drivers there would then create dozens of fake email addresses to sign up for new Uber rider accounts attached to each phone, and request rides from those phones, which they would then accept. Since Uber was handing out incentives to drivers to take more rides, the drivers could earn more money this way.

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To halt the activity, Uber engineers assigned a persistent identity to iPhones with a small piece of code, a practice called “fingerprinting.” Uber could then identify an iPhone and prevent itself from being fooled even after the device was erased of its contents.

There was one problem: Fingerprinting iPhones broke Apple’s rules. Mr. Cook believed that wiping an iPhone should ensure that no trace of the owner’s identity remained on the device.

So Mr. Kalanick told his engineers to “geofence” Apple’s headquarters in Cupertino, Calif., a way to digitally identify people reviewing Uber’s software in a specific location. Uber would then obfuscate its code for people within that geofenced area, essentially drawing a digital lasso around those it wanted to keep in the dark. Apple employees at its headquarters were unable to see Uber’s fingerprinting.

The ruse did not last. Apple engineers outside of Cupertino caught on to Uber’s methods, prompting Mr. Cook to call Mr. Kalanick to his office.

Mr. Kalanick was shaken by Mr. Cook’s scolding, according to a person who saw him after the meeting.

But only momentarily. After all, Mr. Kalanick had faced off against Apple, and Uber had survived. He had lived to fight another day.

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