with one stone. Hourdajian bet that if the reporters got to know Kalanick in person, they might realize he wasn’t such a bad guy.
Hourdajian had gone through the same process herself. Hourdajian, a proud Armenian-American who breezed through her government studies at Georgetown and Harvard, came from the world of politics. She was familiar with schmoozers and phony executives. Though she knew her boss had rough edges, she had come to believe that inside, Travis Kalanick was a good person.
Hourdajian worked alongside Kalanick through some of Uber’s earliest, toughest days. He trusted her to build out the communications team from scratch, and then run it. And when Uber was up against its nastiest early opponents—including taxi operators and government officials—Hourdajian and Kalanick fought side by side in the trenches. She knew Kalanick would never change. But perhaps, if she got reporters closer to him, they would see Kalanick the way she did.
Hourdajian set up a meet-and-greet that Friday afternoon with reporters at the Gramercy Park Hotel, a swank destination in Manhattan’s Flatiron District. In a private room, sitting on leather sofas over plates of brie and mini-muffins, Kalanick made the case to reporters that he wasn’t a monster, and suggested that Uber wanted to build a relationship.¶¶¶¶
They had handed off the job of organizing dinner to Ian Osborne, a well-connected British media fixer, whose job it was to pair important members of the business community with equally important members of the press and Hollywood.
Guests were seated in a private room in the back of the Waverly, away from the common dining area. After cocktails, the diners were asked to sit at a long, skinny wood table—almost too skinny to eat over. Guests were uncomfortably close to one another. Kalanick sat at the head, flanked by Arianna Huffington, the media mogul and celebrity who had built influence in politics and publishing. Huffington and Kalanick had grown close in recent years, meeting for the first time at a technology conference in 2012.
Down the table from Huffington was Leigh Gallagher, a senior editor at Fortune who oversaw the “40 Under 40” list of influential leaders in the business world. On Travis’s other side sat Hourdajian, then Osborne, Uber chief business officer Emil Michael, a handful of other influential New York media writers, and Edward Norton, the actor turned Uber investor. Norton, who had become pals with Kalanick, was Uber’s first official rider when the company launched in Los Angeles.
As Kalanick settled in to schmooze with magazine writers at one end of the table, Emil Michael, his deputy, was cozying up to the media writer Michael Wolff on the other end. Wolff had brought along Ben Smith, editor in chief at BuzzFeed.
Smith’s bubbly personality made him a wonderful dinner guest; his affable manner often disarmed the people he reported on. But those qualities belied a pugnacious streak. Smith had become known in Washington DC for never backing down from a fight. As a reporter at Politico he often sparred on Twitter with those he covered and those he competed with for scoops. When he moved to BuzzFeed in 2012, his mandate was to turn the outlet, long famous for its lolcats and list-oriented viral articles, into a respectable, hard-hitting news organization. Smith rebranded his division as BuzzFeed News, and soon built a serious outfit whose reporting standards and aggressive pursuit of scoops rivaled that of the most traditional newsrooms.
Smith was thus shocked when he, a member of the media, found himself sitting across from an Uber executive who was so openly disdainful about Uber’s relationship with the press. As the group dug into seared halibut and ribeye, Emil Michael, thinking he was amongst a room full of Uber sympathizers and friends, had gone off on a rant about how Uber was unfairly targeted by the press, and had been a victim of its own success.
As the dinner progressed, Smith noticed Michael’s arrogance take over. Michael wasn’t used to Smith’s subtle challenges, pushing back on Uber’s claim that it was providing a public good, or that drivers who complained about pay just didn’t understand the math. Michael didn’t notice that Smith was tapping notes onto his phone as the conversation moved into more controversial areas.
“It’s just bullshit,” Michael said, referencing the waves of negative press coverage. “The way we’ve been singled out like we have.” The worst, he noted, was Sarah Lacy.
Lacy wasn’t a universally beloved figure. She and her partner, Paul Carr, would pick fights with other journalists as frequently as they skewered the