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Venture Capital Cities

Brian Chesky’s Big Gamble

Last month, Airbnb launched its second act, called Trips. The service—unveiled on the stage of an ornate Los Angeles theater hosting the startup’s annual festival—is designed to capture the three-quarters of traveler dollars that don’t go to lodging.

A dive into Trips, an effort to make money from all travel services, provides a look at the 35-year-old CEO Brian Chesky’s management as Airbnb tries to live up to the high expectations that come with being the world’s third most valuable startup, valued at $30 billion. Few in Silicon Valley share his background as a graduate of the Rhode Island School of Design who relies on charismatic storytelling to motivate and guide his employees.

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