Joanna Coles and Brian Chesky at Hearst HQ.


Airbnb cofounder and chief executive officer Brian Chesky talked about starting a business, the nature of travel, making strangers into friends and the company’s big Super Bowl ad during a Q&A on Monday with Hearst Magazines chief content officer Joanna Coles at the company’s Manhattan headquarters.

“I’m sure many of us have had a moment in our lives where we make a decision. And almost every other decision was a consequence of that first decision,” Chesky said. “Well, that happened to me.”

Coles, who is currently in charge of Hearst’s joint venture with Airbnb on a forthcoming magazine venture, which is slated for a May debut, mostly sat back as Chesky launched into the origin story of Airbnb, the wildly successful room-booking company that started back in 2007 when two industrial designers with RISD degrees realized that renting out air mattresses in their San Francisco apartment during a design conference would pay their rent. And, eventually, much more.

Airbnb began to catch on during the 2008 Democratic Convention in Denver (“Remember Obama?” Chesky said,) and really began to take off as a company in 2009, when the foreclosure crisis made more people embrace the sharing economic. It eventually morphed into a start-up that, was, last summer, valued at $30 billion.

The affable-seeming Chesky spoke in the way of successful entrepreneurs, whose ordinary statements turn into almost metaphysical proclamations:

  • “If you start a company, one of the most important questions a person can ask you is what unique insight do you have that nobody in this world has? If you have no answer to that question, then what business do you have starting that company?”
  • “What if you could travel somewhere and feel like you live there? What if you could actually do what people who live there do — be part of a community?”
  • “People love homes, that’s why they live in them.”
  • “I think travel has never really been about where you go. Travel is really about who you want to become.”
  • “People want to do, they don’t want to see. They want to experience and make friends. They want to talk to people who don’t call them ma’am and sir.”
  • “People want experiences, not stuff.”
  • “They want to not just look at art, but experience art.”
  • “When people travel, they want to experience culture. Culture is created through people.”
  • “You see, nobody is a stranger if you add an identity to them.”
  • “When you remove the idea of stranger, you unlock all this equity in the world.”

Speaking of equity….

When investors are looking to invest, Chesky explained, they are looking for a large total available market) a metric used to determine the revenue opportunities in a given industry.

“Here at Hearst, I guess your TAM is advertising. That’s where you get a lot of money. Advertising is, I don’t know, I heard maybe $700 million,” he said. In the early days of Airbnb, a lot of investors didn’t think that travel was a big enough industry. But, Chersky said in hindsight that was ludicrous considering that, at “somewhere between $2 and $6 billion,” it is close in size to the oil industry.

“Travel is huge, and it’s booming,” he said, explaining that the emerging middle class in China, India, Brazil and Russia is creating a huge wave of new travelers.

Chesky recounted the story of how he and his fellow cofounders rushed to put together a Super Bowl ad, which promoted the idea of acceptance, directly in response to President Donald Trump’s executive order that restricted travel from seven predominately Muslim countries.

When asked about the tension between the lofty concepts like erasing borders and breaking barriers espoused by Airbnb and the rightward swing exhibited by the victory of Trump and Brexit, Chesky sounded optimistic.

“Often social progress is two steps forward, one step backward. The future is young people, and they are going to want to live in a more connected world,” he explained.

“I believe that a child, growing up today, is not going to want to have walls around them. They are not going to have this sense of the other. They are going to be part of their nation, and their community. But also of the world,” Chesky said. “And anyone that is betting against the way that kids want to live is going to be on the wrong side of history.”

If there’s anyone who should give advice on betting on the way kids want to live, it’s probably an Airbnb founder.

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