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Find and stop anyone driving for Uber, the fast-growing ride-hailing startup.
The service was launching that evening, without the bureau’s approval.
Travis Kalanick,
David Plouffe,
Charlie Hales,
“We’re really trying to provide a service to your citizens here,”
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.
“You’ll have to excuse me, I just gotta get up and move around,” Kalanick would say, already out of his chair. Then he would continue the conversation, full of kinetic energy.
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.
Kalanick was done waiting. It was time to go. He gave the word and Uber general managers on the ground in the Pacific Northwest got the message: Protect the drivers, trick the cops, and unleash Uber in Portland.
Whenever it entered a new city, the company used the same, reliable approach. 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.
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.
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.
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.
More than once, investors and employees worried that the entire future of the company was at stake.
I feel lucky to have been along for the ride.
It was an Uber tradition for Travis Kalanick to take the company on the road after hitting growth targets.
He also noted that any puking on hotel grounds would result in a $200 fine. The email set the tone for the rest of the retreat.
The ten billion revenue figure was special. Everyone appreciated the significance of such a big, round number, and Kalanick in particular had an affinity for the mathematics of exponential growth.
They loved how Kalanick brought a hacker-like mentality to the way he built and ran his company. No one wanted to miss their shot at entering the next Google or Facebook on the ground floor.
Rachel Whetstone,
A Los Angeles general manager was fired in 2015 for groping the breasts of one of his team members.
But the crown jewel was the final musical guest. As Uberettos lined the venue inside the Palms hotel, the house lights went dark and the stage filled with smoke.
Employees began screaming as the singer stepped into the spotlight. They realized what Kalanick had done: He got Beyoncé.
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.
“make a dent in the universe.”
This was the height of tech utopianism. And though Kalanick would have no way of knowing it until years later, Uber’s company trajectory would closely map that of the tech industry more broadly. Both were surging faster, higher than anyone could have anticipated.
“Is this a joke?”
“Is this still part of the whole professor act?”
Ryan Graves,
“always be hustlin’,”
“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,”
Bill Gurley, a former financial analyst turned legendary Silicon Valley venture capitalist, would prove to be instrumental in Uber’s entire arc of success.
Uber employees were always sprinting. They kept working even after they went home, terrified of both their competitors and their bosses.
Travis Cordell Kalanick was born on August 6, 1976, in Northridge Hospital to Donald and Bonnie Kalanick, an average, white, middle-class couple who built a comfortable life for themselves in California.
“She wore her heart on her sleeves,” Travis later said of her. “And when she walked into a room, her warmth, her smile and her joy would instantly fill it.”
One friend described him as a pit bull that spent its life getting kicked by its owners—no matter how beaten down Travis was, he never, ever gave up.
“Success in athletics doesn’t happen by accident; it requires hard work and discipline,”
What Kalanick was describing, without realizing it, was a proto-version of Napster, the iconic file-sharing network co-founded by Sean Parker, an internet entrepreneur and, later, an early advisor to Mark Zuckerberg at Facebook.
“We were running out of money, our server costs were going up, our traffic was going through the roof,”
Ron Burkle
Michael Ovitz,
They wanted to send a message: Any entrepreneurs thinking of building their own file-sharing companies would be sued into oblivion.
He had dropped out of college, forgone a real salary, moved back in with his parents, and abandoned the idea of a romantic relationship.
Some companies were indeed good bets. Amazon, eBay, Priceline, Adobe—a number of the startups formed in the ’90s outlived the dot-com era. These companies were able to do something many of their contemporaries weren’t: build a sustainable underlying business.
For a starting price of $25,000, employees at Startups.com would help new companies find an office, pick their furniture, even figure out their payroll software.
That company was called Red Swoosh. “We basically took our expertise in peer-to-peer technology, took those thirty-three litigants, and turned them into customers,” Kalanick said.
“Tumbleweeds blowing through,”
From the start, the team didn’t love Kalanick’s leadership.
