Not coincidentally, Airbnb.com came about when the lives of its two co-founders, as well as the American economy, were at a crossroads. The way Americans conceptualized vacation was changing, and the idea of “renting from real people” emerged to fill a gaping void between hotel stays and budget travel. With Airbnb.com, vacation doesn’t have to be a financial extravagance (although it certainly can be, as Airbnb.com's offerings extend to spaces that would make The Four Seasons look like a hostel). Whether it’s a spare couch in a studio apartment or a vacant house by the beach, individuals around the world are making money by letting strangers into their homes, and anyone with a computer and a credit card suddenly has access to a space and a culture that they might otherwise never experience. We caught up with Chesky one morning after he arrived at the office, coming straight from the Airbnb.com listing in San Francisco that he called home for the previous week. He spoke about his Industrial Design background, becoming a user experience guru, and the future of work, life, and travel.

How was Airbnb.com born?

I had just quit my job in LA and drove up to San Francisco to live with a friend from RISD [Rhode Island School of Design], Joe Gebbia. I got there, and we basically realized that our rent was more money than we had in our bank accounts. You know, out of necessity, you sometimes become very, very creative. Well, this is one of those cases. We were basically aspiring entrepreneurs, we knew that we wanted to start a company doing something, but we didn’t know what. It turned out that that first weekend I came to San Francisco, there was this international design conference happening, the IDSA. On the conference website, all the hotels were sold out. Joe and I were talking, and we came up with the idea of having a designer bed and breakfast. The idea is that we can just house the designers, get to meet them, and make money to pay our rent. I didn’t have any furniture, but we had an air bed in the closet. We ended up hosting three people. The fact that they were from totally different demographics and from all over the world was the thing that made us start to realize that maybe there was a new idea here. What’s funny is that even after that first week, it still wasn’t clear that Air Bed and Breakfast was going to be the business. We were still brainstorming business ideas. It wasn’t until about six months later, when we launched the website, that we were really committed to the idea of it.

How has Airbnb.com evolved since the “air beds for conferences” days?

As we started growing, it became clear that people wanted more than just Air Beds. They wanted houses, they wanted just space, in the abstract sense. They didn’t just want space for events, they wanted space for vacation, for business trips. We started thinking, why limit it? So it all started with just sharing, well, living rooms. Then it went to bedrooms, then it went to entire homes and apartments. From there, it started going to all sorts of other spaces, like castles, tepee houses, boats, igloos, anything. And that’s where it’s moving towards today. We really think of ourselves as a marketplace now for space.

The people out there renting rooms have driven many of the changes you’ve made to the Airbnb.com concept. What are they asking for now?

People are requesting two things from us. People are requesting that they can book or rent out different types of spaces, and they’re requesting that they can rent them out for a larger window of time. They’d love to rent out their bike, their parking space, their car. They want to be able to rent out a hot air balloon, a pool, things you could never imagine.

You have a background in industrial design. How does that play into your work now?

I think that industrial design is all about user experience. You become a user, you become your own guinea pig, you learn to observe the world. It’s important that you put yourself in the shoes of the user and really use the product. I literally live in Airbnb.com. I gave up my apartment and only live in spaces found on Airbnb.com. The original reason I did it was because we needed space; we turned the bedroom into a meeting room. It’s meant to be a short-term thing, because I needed a place to go. And then I decided, you know, this is actually an industrial designer’s dream. In other words, if you were designing medical equipment, you would want to be in an operating room, observing. You wouldn’t just want to be looking at data at all. And that’s the thing that we think about. We think about user experience. Put ourselves in the shoes of the user, and we view the decisions coming from a design-oriented philosophy.

Tell me about your experience living only in Airbnb.com rooms. How long has this been going on?

It’s been going on for three months so far, and I change spaces about every five nights. It’s been amazing. I’ve stayed in very unique spaces, very social environments. I’ve stayed with one of the top air guitarists in San Francisco, also a guy who is the #2 ranked Ski-Ball champion in the US. I stayed at one architect’s house; he designed his own house, and it was a beautifully furnished, a very open and modern eco-friendly planned space. Originally, I told everyone I was going to do this for the summer. Then I said, what the hell, I’m going to take it all the way through 2010. I do have a personal goal, which is to do it until I’m 30. I’m 29 now, so for another year. As an industrial designer, you just have to consume it, you have to live it. I think what I’m doing is slightly extreme, kind of pushing the boundaries, but I actually think that it’s the future of how a generation of people will live and travel.

What benefits has the experience had for your business?

Understanding nuances and learning how to empathize with our users. Also, improving the UX of site. As an industrial designer, you just have to consume it, you have to live it.

How has your team grown since you guys set up shop in your apartment?

We have close to 20 people working in the office. The culture has a very laid back and fun, informal environment. We’re always sharing ideas and running around; it’s super high energy. We try to give people a lot of autonomy to do their own thing, so they can champion their own ideas. As long as they communicate their vision for our goals and what we’re trying to accomplish, it’s just a matter of then giving people the autonomy to pursue what they think their contribution to the company can be. Everyone who works here gets to travel a lot on Airbnb.com. Half our team did a European tour; we went to Edinburgh, London, Dublin, Copenhagen, Amsterdam - it was a nine-city tour. Every few months we do a big company trip somewhere, and we stay in Airbnb.com listings. We think about the office culture just like we think about the product, it’s something you’ve got to work on, you’ve got to build, you’ve got to create, you’ve got to be creative about it. If you just try to kind of let it happen, it’ll just feel like an office.

What are some of your favorite spaces listed on Airbnb.com?

The next one on my list to stay in is a tepee in the San Francisco area – it has wifi and everything. I’d love to stay in an amazing villa, the White House of Costa Rica. We have a few different vacant airplanes that you can sleep in. Also, the giraffe manor in Kenya. There’s an ancient British castle in Stainmore and a castle in Morocco I’d like to stay in. We actually have Frank Lloyd Wright-designed homes around the country, and I want to stay in at least one of those. There’s this amazing igloo, I believe in Switzerland, it’s only open half a year, when it’s cold out.

What is your daily routine like?

Email olympics in the morning. I spend more than half my day meeting with people; mostly job candidates. I work out at night around 8pm, then head to my Airbnb.com where I work until I pass out. I read about a book a week, and usually use lunch to catch up on reading.

What would you say Airbnb.com’s biggest challenge is right now?

Our biggest challenge is the fact that we are growing internationally. As you have all these different people meeting from different cultures, we have to be able to support their different languages and currencies. There’s also a lot of different expectations between cultures, especially when they’re sharing space. You know, there’s just a lot of uncharted territory there.

Do you have any advice for other young entrepreneurs?

My advice is to solve your own problem, get your smartest, most passionate friend to be your co-founder, and be prepared to do what no one is else is willing to do in order to succeed. -- You can keep up with Brian’s travels on Airbnb.com at Where’s Brian.