A Lofty Plan: The Story of Airbnb

It must have sounded like a crazy idea at the time but it’s since become the stuff of legend. Back in 2008, Brian Chesky and Joe Gebbia were two ambitious entrepreneurs living in an expensive loft in San Francisco’s South of Market neighborhood. While hunting for their big break, they decided to supplement their income by renting out their living room to overnight lodgers. The duo got their hands on a few air mattresses and tossed in a complimentary breakfast to anyone willing to take them up on their offer.

Given the price of the average hotel room in The City by the Bay, it should come as no surprise that many people did just that. Chesky and Gebbia knew they were on to something and called in Harvard grad Nathan Blecharczyk to help them expand the concept into something bigger and better. After raising $30,000 by selling politically-themed breakfast cereals (of all things), they launched Airbedandbreakfast.com that August.


From there, the whole thing took off like a wildfire. The following spring, after shortening the company’s name to the far more catchy Airbnb, an ever increasing number of users flocked to the website to create listings for their properties. The variety of rentable spaces also became increasingly diverse and outlandish. While many were eager to rent out an extra bedroom or a vacation home, others posted listings for everything from tree houses and tugboats to igloos and private islands.

As the website grew, so did the company itself, which Chesky and Gebbia initially housed inside their loft. At one point, Chesky gave up his own bedroom to make space for their employees. He opted to live in various Airbnb properties until the duo could track down a proper office.




Growing pains

It’s an amazing success story but this isn’t to say that Airbnb hasn’t endured its fair share of growing pains. The company has sparked an ongoing series of debates over lodging legalities and tax assessments in several cities around the world. More than a few hotel operators would also like to see it put out of business for plenty of reasons that need not be mentioned here.

As Airbnb looks to open a new operational headquarters in Portland, Oregon’s historic Old Town neighborhood this summer, it faces a bright, but possibly bumpy, future. In the meantime, the website remains a godsend for thrifty travellers and those searching for lodgings that are a bit more interesting than what the average Marriott has to offer.


[This story was originally published in April, 2015]