Brian Chesky, Joe Gebbia, and Nathan Blecharczyk could not make rent. It was 2007, and a design conference was coming to San Francisco with no hotel rooms available. They put three air mattresses on the floor of their apartment, set up a basic website called AirBed & Breakfast, and charged visitors $80 a night. Three strangers slept on their floor. That was the beginning.
Leigh Gallagher, an editor at Fortune, traces the company from that moment through its growth into the largest accommodation provider in the world, with a valuation that surpassed Hilton before the company ever went public. The book covers the mechanics of how they scaled: the Obama O’s cereal boxes they sold to keep the lights on, the Y Combinator batch that taught them to do things that don’t scale, Chesky’s decision to personally visit hosts and photograph their homes.
But Gallagher does not write a hagiography. The second half of the book deals with the parts Airbnb’s marketing prefers to skip. Cities from Barcelona to New York passing regulations to limit short-term rentals. Neighborhoods losing long-term rental stock as landlords convert apartments to Airbnb listings. Incidents of discrimination by hosts. Safety problems in unregulated properties. The tension between what Airbnb says it is (a community platform connecting travelers with locals) and what it sometimes functions as (a machine for converting residential housing into hotel inventory) gets honest treatment.
The profile of Chesky is the most interesting thread running through the book. Gallagher had extensive access and describes a CEO who is genuinely obsessed with design, community, and the guest experience, but who also had to learn on the job how to manage a company growing faster than anyone, including him, expected. He comes across as earnest to a degree that occasionally annoys even his admirers.
The book was published in 2017, before Airbnb’s IPO and before the pandemic temporarily devastated the travel industry and then sent demand for remote-work-friendly rentals through the roof. Some of the regulatory battles described have since been resolved, others have intensified. The core story, how three people with no hospitality experience rearranged a $500 billion industry, holds up regardless.
Reid Hoffman called it a fast-paced and fun dive. Charles Duhigg praised its treatment of entrepreneurial audacity. It is the standard reference on the Airbnb origin story.
