The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World Kindle Edition

Brad Stone has pulled off a rare feat: he’s written the definitive story of two very different companies, Uber and Airbnb, in one book. By interlacing, comparing, and contrasting the two giants of the sharing economy, our insight is heightened and the narrative never drags.

The book works on multiple levels: a detailed and fascinating behind the scenes revelations of how of the two biggest, most transformative companies started, grew, and operated; as a business book sure to be appreciated by entrepreneurs and managers of all stripes; as a partial champion and partially careful critique of the tech culture and nascent sharing economy; and as a ripping good yarn that anyone who likes a good story can appreciate.

What sets this book apart from others is that Stone is a real reporter, highly respected and renowned in the tech industry, with a long career of success, including his last best seller, The Everything Store about Jeff Bezos and amazon. Unlike some other books about these companies — including one solely on Airbnb that is about to be released and for which i read an excerpt in Fortune — Stone’s book isn’t pure hagiography or a trifling puff piece that feels like it was written by the P.R. departments of Uber or Airbnb. There is real, nuanced, and sometimes critical reporting being done here.

Perhaps, too, that leads to the one critique of this otherwise superb book: Stone is so careful and measured in his tone and approach — never allowing his opinions to overshadow the known facts — that sometimes I wished he was more daring in speculating about what it all means, and the possibly dystopian ways it could all shake out down the road. But of course, in this dark day and age, there’s something to be said for a media member who is careful in his approach, so it’s hard to ding him too hard for sticking to the known facts and allowing the reader to draw some of our own conclusions.

That said, if you are interested in these two companies, starting or growing a company of your own, the tech industry in specific or business in general, the ins and outs of the new sharing economy, or just some compelling human interest, this is surely the new must-read book on the subject.

Many Americans, not to mention millions of people in other countries around the world, may find it difficult to imagine a world without Uber or Airbnb. Yet Uber was founded only in 2009 and Airbnb a year earlier. (Neither company’s success—or, for that matter, the sharing economy as a whole—would have been possible without the iPhone, which Apple introduced in 2007.) As the cover graphic suggests on Brad Stone’s captivating new book, The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World, these two iconic companies have been riding the wave of new and ever-improving technology.

Is this the sharing economy?

“Airbnb and Uber didn’t spawn ‘the sharing economy,'” Stone writes, “. . . so much as usher in a new trust economy, helping regular folks to negotiate transportation and accommodations in the age of ubiquitous internet access.” Even before going public, the two companies together were valued at close to $100 billion. There is no evidence that their principals have shared any appreciable portion of that wealth. Nor does it seem consistent with a gentle label such as “the sharing economy” for Uber to resist every effort to classify its drivers as employees and provide them with benefits.

Stone contends that “Together, these companies have come to embody a new business code that has forced local governments to question their faithfulness to the regulatory regimes of the past.” In the course of doing so, both companies have engaged in bare-knuckle fights with local governments around the world. For the most part, they’ve won. But not always. Stone tells the fascinating story, blow by blow.

The five men behind the two companies’ rise

Stone’s book is tightly focused on Uber and Airbnb, with digressions about the many companies that have tried to compete with them, with only meager success for the most part. In fact, in a sense, the book is about the two companies’ cofounders, and especially the two young men who have emerged as CEOs. Travis Kalanick runs Uber. Brian Chesky is at the helm at Airbnb. However, the two companies’ success may well be due as much to the contributions of their cofounders: Garrett Camp in the case of Uber, and Joe Gebbia and Nathan Blecharczyk in the case of Airbnb. All are featured in Stone’s account. They’re all billionaires now, many times over.

The trouble with Uber and Airbnb

Stone makes clear that many of the problems that have surfaced in the news media about Uber have been caused by its CEO. “Chronically combative” (and sometimes abusive), Travis Kalanick continues to generate negative publicity, seemingly on almost a daily basis. Here’s one recent example that emerged in The Guardian—an article about Kalanick’s abusive treatment of one of his company’s drivers. And here’s an even more recent report about the company’s use of software to evade police in at least five American cities and six other countries. These are not isolated instances of controversy surrounding the company: trouble seems to follow Uber with disturbing regularity.

Many of these reports reflect Kalanick’s combative personality, but there are other problems as well. For instance, Anna Weiner wrote in the Feb. 28, 2017 New Yorker about recent reports of sexual harassment at the company: “Uber is, in some ways, a model villain. The company has long inspired Schadenfreude. It has been accused of mishandling customer reports of sexual harassment by drivers.”

A shared reputation for aggression

As a result of the frequent, high-profile accounts of Uber’s misbehavior, Airbnb tends to be regarded more highly. But Stone argues that CEO Brian Chesky is frequently as aggressive as Kalanick. Neither has shied away from blatantly breaking local laws or confronting local officials. “Reflecting on the years 2011 through 2013,” Stone notes, “a person might find it difficult to conclude that one company was the more ethical operator . . . Both CEOs seized the tremendous opportunities before them with steely determination, pausing just long enough to turn around the repair some of the carnage they left in their wake.” Stone adds, “in the end, there emerged an unavoidable fact: Chesky was every bit the warrior Travis Kalanick was. He believed so much in the promise of his company that he was going to fight for every inch of territory.” Both companies racked up so many victories against local officials because their services had come to be regarded as essential by so many residents—and the high-priced lobbyists they both hired managed to mobilize so much support that local officials were forced to back down.

A final assessment

After cataloguing a litany of offenses by both companies, Stone relents in the end. “Both Travis Kalanick and Brian Chesky had made big promises: to eliminate traffic, improve the livability of our cities, and give people more time and more authentic experiences. If these promises are kept, the results might well be worth the mishaps and mistakes that occurred during their journeys; perhaps they’ll even be worth the enormous price paid by the disrupted.” Not to mention that $100 billion the two companies’ founders and investors have amassed.

About the author

Brad Stone is a senior executive at Bloomberg News in San Francisco. The Upstarts is his third nonfiction book. The second was the bestseller The Everything Store about founder Jeff Bezos and the rise of Amazon.com.