Leadership Transformation

The Upstarts is the definitive story of two new titans of business and a dawning age of tenacity, conflict and wealth. In Brad Stone’s riveting account of the most radical companies of the new Silicon Valley, we discover how it all happened and what it took to change the world. The following excerpt gives you a glimpse into how Brad got two of today’s most innovative leaders to share their stories.

THE UPSTARTS by Brad Stone. Copyright © 2017 by Brad Stone. Reprinted with permission of Little, Brown and Company.

I met Brian Chesky at his company headquarters at 888 Brannon Street in San Francisco, a lavishly renovated former battery factory. The entrance to the building is majestic, with a five-story open atrium that is both striking and impractical; one three-story stretch of wall is furnished with a variety of plants that need almost constant care. Airbnb occupies several floors that have inspirational sayings etched on the walls and conference rooms decorated to look like exotic home rentals on the site.

I met Chesky in the Founders’ Den, a wood- paneled holdover from a previous tenant, a paper-distribution company. Four brown leather armchairs surrounded a circular coffee table that sat on an oriental rug. It was an anachronism from the 1950s amid the splendor and excess of San Francisco’s twenty-first-century internet boom. Across the street, cranes were assembling new high- priced condominiums.

Chesky is five foot nine and fit from a regular workout regime. He spoke quickly, with spasms of tension occasionally passing over his mouth, and related the history of his company’s meteoric rise in terms of the moments of its most dramatic adversity.

Early in Airbnb’s history, he said, “It felt like the world was against us and everyone was laughing at us.” The startup persevered through widespread rejection by investors, battled a ruthless European rival, and survived a deluge of negative publicity around the early destruction of one of its hosts’ homes by an unruly guest. “No one believed in us. We were insecure and had no idea what we were doing,” he told me.

More recently, the primary adversaries have become regulators and housing activists. Some of them are looking to score political points by vilifying a high-Profile target; others are legitimately worried about Airbnb’s impact on housing affordability. Unlike his friend Travis Kalanick, Chesky presents himself as a sympathetic ally of those in the latter category. “We want to enrich cities. We don’t want to be an enemy of affordable housing,” he said. “I think we can be on the right side of the argument. We let many of our users stay in their own homes. This is why we were founded. If I didn’t need the money to pay rent, we wouldn’t have started the company.”

As for the book project, he was game. Over the ensuing year, I spoke to Chesky, his co‑founders, and top Airbnb executives. The company’s PR representatives were helpful though understandably nervous about the outcome, soliciting questions for interviews ahead of time, sitting in on conversations, and taking copious notes.

Then there was the monumental challenge of obtaining the cooperation of the famously combative Travis Kalanick, known as a contrarian who advocated fiercely for his company’s interests. He did not disappoint. “I came to this meeting out of respect for you and your work,” he said when we met for dinner in March 2015 at the Burritt Room and Tavern in San Francisco’s Mystic Hotel. “But I’m going into it thinking, There’s no way in hell I’m cooperating with a book about Uber right now.”

Kalanick had endured a year of negative press over Uber’s tactics toward rivals, its ambiguous impact on cities, and its tense relationship with drivers. David Plouffe, Obama’s former campaign manager and at the time Kalanick’s chief of media relations, came along for the dinner and wore the bemused smile of someone witnessing a journalist’s suicide mission.

Despite the inauspicious start, Kalanick seemed willing to listen. He asked what he had to gain by cooperating. “If you want people to embrace a radical future in which they give up their cars,” I argued, “you have to allow journalists to explain and demystify your story. If you want to change the way cities work, Uber must be understood.”

It didn’t work. “You have to inspire me!” he said. “Tell me what we have to gain!” He was forthright and transactional; in other words, Travis being Travis.

At some point during the rye whiskey cocktails and flat- iron steaks with garlic-paprika fries, he seemed to warm briefly to the cinematic potential. “You’d start this story with a city council meeting,” he mused. “The city council people are sitting up in front of the room and they are misinformed. They are thinking mostly about where their next campaign contribution comes from. There’s an Uber rep there, but he is basically alone, trying to describe an unfamiliar and strange technology to people who have no understanding of it.

“The Uber guy has a lobbyist, but the lobbyist is also working for the other guys on the side. Finally, you have the big taxi guys there, and they have the city council locked up and paid for.

“Then, meanwhile, you’d cut to the taxi guys at the airport. They are all waiting there for hours, playing cards or whatever, for the chance to pick up one fare. And there’s an Uber recruiter there, and he is surrounded, explaining this new system to the drivers . . .” Kalanick caught himself and trailed off. “Anyway, that’s how you’d start the movie.”

On the street after dinner, he said again, “You have to inspire me,” as if I hadn’t just spent two hours laying out my best arguments. Then he and Plouffe took off on foot, back to the office.

Six months passed, and despite my repeated entreaties, I didn’t hear anything. But then, after I’d talked to dozens of regulators, competitors, and current and former Uber employees, a new Uber PR executive somehow convinced Kalanick to cooperate. I eventually spoke with two dozen different Uber executives from all periods of the company’s brief history and had another few hours of Kalanick’s time to complement several interviews I had conducted with him over the course of my five years as a writer for Bloomberg Businessweek.

The result is this book. It is not a comprehensive account of either company, since their extraordinary stories are still unfolding. It is instead a book about a pivotal moment in the century-long emergence of a technological society. It’s about a crucial era during which old regimes fell, new leaders emerged, new social contracts were forged between strangers, the topography of cities changed, and the upstarts roamed the earth.

May 9, 2017


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