Lucky for him, his company specializes in providing temporary lodging. So he decided to explore firsthand how good his product is.
Brian Chesky is kicking back in the room he found on hid company's own website -- www.airbnb.com.
"Why not eat my own dog food, use my own product, get to know our community all over the city. So I'm staying in places for the next six months, I will probably stay in 50, for about three nights each and really get to know the users," he said.
His old bedroom will soon to be a conference room, his old living room is now company work space until October when the company will move to a larger facility
And until then, Chesky will be exploring. For example, he found out that for $89 per night he can get a room in a house with five other guys he'd never met before -- guys including Matthias Hensen from Germany who found out on airbnb dot com what $15 per night can get you.
"I got a couch but still, I get a bunch of really cool people to hang with, so we've been exploring the town, they've given me a lot of advice and it's really helped me explore San Francisco," he said.
"Any type of traveler that's looking for a local experience in travel or for an affordable alternative to a hotel, or for a more social experience to traveling benefits from this," Chesky said.
And those who rent out the rooms and houses benefit too of course.
"So I rent out my room for about five to six nights a month, brings my rent down I rent it for $90 a night, so brings my rent down to $500 a month. So I can afford a room with a Jacuzzi, fireplace and it also pays my traveling," Andrew Kitchell said.
The company gets its name from when Chesky was trying to make extra money years ago. He created a bed and breakfast of sorts by offering an air mattress for rent on the floor of his apartment
Now his company can book you place for a night, a week a month -- all kinds of places in 5,000 cities in 145 countries.Airbnb.com makes money by keeping 10 percent of the payment and it works like Craigslistwith a few big safety differences.
"We handle all payments through the site, so you don't have to deal with cash. You book a room on our site, just like you would on hotels.com , we have user profiles so you know who is staying with you, we have a trust system that's built," Chesky said.
And rentals range from $15 dollars for a couch to how about a few nights sleeping inside an airplane in the Netherlands, or maybe enjoying a longneck in Kenya.
"You are eating breakfast in the morning and a giraffe just pops his head out," said.
And just to think that all of this started with an air mattress, a little extra space and a big imagination.