What the CEOs of Uber and Airbnb learned about negotiating from having dinner with each other

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Uber and Airbnb have much in common. Both VC-backed startups are stars of Silicon Valley and evangelists of the new sharing economy. Both have survived bruising fights with entrenched, heavily regulated industries—facing violent protests against Uber in Paris, for example, and politicians hostile to Airbnb in New York.

But their approach to those battles have been quite different. Uber is known for its hard-nosed, take-no-prisoners approach, while Airbnb has tried to be friendlier and more collaborative.

It turns out the two companies learned to modify their approach to negotiating through a series of informal dinners between their CEOs, according to Brad Stone, the author of The Everything Store on the growth of Amazon and of a new book, excerpted in Bloomberg Businessweek, about Uber and Airbnb.

Travis Kalanick, CEO of Uber, and Brian Chesky, CEO of Airbnb, would return from the dinners inspired to change their companies. “Brian would come back saying, ‘We have to be tougher!’ and Travis would come back saying, ‘We have to be nicer!’ ” according to one Airbnb employee.

The men would meet for dinner every few months in San Francisco as their companies grew. Initially, it was just the pair, then later they were joined by their girlfriends and other entrepreneurs. “I think we learned a lot by watching each other,” Chesky told Stone.

While Uber didn’t get much nicer, Airbnb got tougher in its dealings with the cities and states standing in the way of its expansion, Stone says. While it once tried a gentler approach, it eventually learned to get tough—and battle it out like Uber.