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Inside Airbnb’s Cuban Revolution


While Airbnb has faced headwinds from legislators and unions stateside, the homesharing behemoth is staging a major coup in Cuba, rapidly expanding to the country and whipping up massive PR victories on the island.

The company has made Cuba a top priority, jumping through legal hoops and web-access hurdles to bring what CEO Brian Chesky calls  “person-to-person diplomacy” to the paradise—raising flags that the timing of Chesky’s trip to Cuba, hand-in-hand with President Obama’s, was no coincidence.

And Airbnb’s narrative parallels the President’s. The company lets Cubans become small-time entrepreneurs, raking in $250/booking, at a time when the President is promoting the American Dream to the Cuban people.


“As we’ve seen in America, businesses that start small—even in a garage—can grow into some of the world’s most successful companies,” the President said to a beer brewery full of Cuban entrepreneurs.

That stands in contrast to Airbnb’s battles with NY and S.F. legislators back home, along with its recent breakdown of negotiations with one of the nation’s largest unions.

The jury is still out as to how much business (if any) Airbnb steals from the lodging industry, but American hoteliers will be sad to see the company overtaking their potential market—13,000 Americans have booked Airbnb’s on the island, making Cuba the fastest-growing market Airbnb has ever launched. [Fortune]