Brad Stone On The Past, Present, And Future Of Uber And Airbnb

April 17, 2017
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by Peter High, published on Forbes


Brad Stone has written multiple bestselling books that have chronicled leading technology companies and the leaders behind them. His book, The Everything Store: Jeff Bezos and the Age of Amazon highlighted Amazon’s rise from online bookseller to a digital channel through which you can purchase almost anything. Along the way, he highlights Jeff Bezos role in setting a high- achieving though at times abrasive culture that has allowed the company to thrive for more than two decades even though it has reached a scale that might seem unwieldy.

Stone’s latest book is The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World. In the era of the unicorn (venture funded private companies with valuations over a billion dollars), Uber and Airbnb have captured the public’s imagination (as well as the ire of regulators) more than most. Stone highlights the remarkable similarities between the companies. They were founded within months of each other in San Francisco. Each faced long odds and tough competition, but through a combination of idealism and ruthlessness (an essential combination for start-ups to balance correctly according to Stone) emerged as leaders in their respective spaces. The story is also a fascinating account of the founders and leaders of each company, each of whom have molded the companies into their own images in many ways.

Stone finds fascinating stories to tell, but his telling is especially artful. These books are great primers for aspiring entrepreneurs as well as those who are simply interested in what makes entrepreneurs successful.

Peter High: Congratulations on a terrific book,The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World. Early in your book, you describe the process of getting Airbnb and Uber executives to speak on the record, which must have been difficult. Can you describe how you made both companies and their executives comfortable speaking with you for the book?

Brad Stone: Executives are rarely comfortable speaking on the record, particularly in secretive Silicon Valley companies. They are never excited about opening the kimono and talking about their companies’ history beyond the self-styled mythology they have created. I learned that with my book about Amazon a couple of years ago. The inevitability of the project is a large part of getting executives to speak on the record. You are asking for access, but the book will proceed regardless.

When I went to Uber and Airbnb for The Upstarts, the responses were characteristic of the organizations. Airbnb is a company with values around hospitality. They welcomed me in, they were nice hosts, and they expressed enthusiasm. I immediately sat down with Brian Chesky, their CEO, and ultimately the organization gave me quite a bit of access. Of course, they managed that heavily and tried, as all companies would, to shape their message aggressively. By and large, my Airbnb experience was smooth. Uber, on the other hand, is more of a combative company. After a couple of months of asking to pitch this project, Travis Kalanick went to dinner with me. He forcefully told me there was no way he would cooperate with a book right now. I had expected that, and I chipped away for another couple of months. Eventually, when Uber saw that I was proceeding with the book, and it was going to happen, Travis started cooperating and gave me a couple of interviews and access to members of the senior team. When you are facing a project like my book, it is smart and tactical for companies to share their perspective. In the cases of Uber and Airbnb, they both have plenty of critics, plenty of competitors, plenty of enemies, they need to aggressively share their story.

High: In The Upstarts, the differences between Chesky and Kalanick are stark. You write about how the shared experiences created a bond between the two and they would meet to discuss similar challenges and concerns. However, after their meetings, Chesky would go back to Airbnb and say, “We have to be tougher,” Kalanick would go back to his team and say, “We have to be nicer.” Given the accomplishments of both organizations in disrupting industries, what can you draw from the different cultures at each company, in terms of similarities and differences, and what importance do you give to those elements of their cultures?

Stone: Both companies rode the same fundamental wave of technology. They extended the digital world into the physical one. They marshaled the movement of people around cities; Airbnb putting people into homes, Uber putting people in their cars. They both ran headlong into city regulations, local politicians, unions, and pretty entrenched companies. Since the companies followed a similar path, they experienced similar challenges. They saw the opportunity to look at each other and learn from each other. To some extent, they were jealous of each other. Uber because Airbnb, for the first couple of years in most parts of the world, was able to fly under the radar of local regulators. That is no longer true, now we see pushback against Airbnb in many cities. For a while though, probably everywhere other than New York City, Airbnb almost got a free pass. Whereas Uber was in a fight from the beginning. Three months after it launched in San Francisco it got a cease and desist order. They had to battle and marshal their customers together to persuade regulators to change the law, or to clarify the law. Airbnb was impressed that Uber created a powerful force out of their customers, and they were able to use that to pressure lawmakers. Airbnb was never able to do that as successfully because half of their customers are out of town or traveling around the cities they are visiting. The other half, the host community members, will not always speak publicly because their actions may bend the law or alienate neighbors.

While the challenges faced by the two companies were similar, and they did learn from each other, their dispositions are different. Uber is an attack dog, which served it well –until somewhat recently. Airbnb puts a nice little shine on everything. They talk about the regulatory brand, wanting to be in the room with regulators and talk with them. They think if they are there, they will be liked. Uber does not care about being liked. In my book I describe how Travis would go into meetings with regulators and position his chair so his back was toward them.

High: You write about the number of companies that at one point competed right alongside Uber and Airbnb, but ultimately failed. In some cases these were companies that even beat Airbnb or Uber to the transformative or disruptive ideas. What are some of the differentiators that allowed Airbnb and Uber to succeed where others did not?

To read the full article, please visit Forbes

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