Portfolio April 8, 2011

The Entrepreneur Questionnaire: Brian Chesky, Co-Founder and CEO of Airbnb


Brian Chesky is Co-Founder and CEO of Airbnb, an online community and marketplace for unique spaces. Airbnb, a Greylock-backed company, connects people who have space to spare with those who are looking for a place to stay. The site has helped people book more than 1 million nights in more than 9,000 cities in 176 countries around the world.

Describe your business in 10 words or fewer.

Community marketplace that connects people through unique spaces around the world.

What is the big idea behind your business?

For the first time ever with a single click of the button you have access to places, people and experiences to which you never had access before. It’s as easy as booking a hotel but with a local, authentic experience.

How did you come up with the idea for Airbnb?

Joe [Gebbia] and I had just moved to San Francisco and become roommates in 2007. Neither of us had a job and we needed money for rent. We were both designers and we knew the International Design Conference was coming to San Francisco in October, yet all the hotels were sold out. We thought we could make some money if we rented out our place and turned it into a bed and breakfast. We got three airbeds and created a Web site called “Air Bed and Breakfast.” People signed up to rent the airbeds and we cooked them breakfast every morning and acted like tour guides. We didn’t mean to start a business. It just sort of happened. There was no flash of genius. In the beginning, we didn’t realize that this would be the big idea. It was the thing that would pay the rent until we thought of the big idea. Gradually it became obvious that this was the big idea. Eventually we expanded beyond our apartment and our three airbeds and shortened the company name to Airbnb.

Why are you excited about the future for this company?

We are creating a new economy. We are giving consumers access to millions of people, unique spaces and experiences around the world. Airbnb turns online connections into real world meetings. It’s a new way of life, a new way to meet people, a new way to make money and a new way to travel. We also bring liquidity to a new marketplace that previously didn’t exist. In the next few years we will do for space what eBay did in the late 1990s. Some of our customers call it a revolution; some call it a movement. We’re living in a peer-to-peer, collaborative consumption era and Airbnb is helping to propel that forward.

Why did you become an entrepreneur?

I always was an entrepreneur. I grew up as an artist, which is similar to an entrepreneur in that you have a vision and you have the freedom to create it. Being an entrepreneur, you also have access to resources and people who can take your vision and help you bring it to the world. One of the tenets of industrial design is that you can be in service to the world and improve things in a meaningful way. To change the way millions of people live around the world is very compelling.

What was the most difficult lesson you have learned as an entrepreneur?

One of the lessons I learned from Paul Graham was to do important things that don’t scale. Frequently advisers tell you not to do things that can’t be done for millions of users at a time. Paul encouraged us to knock on doors to meet our users face-to-face. You obviously can’t do that for millions of people, but even on a small scale, it helps to build loyalty among your customer base and the information helps you improve on your product.

Another important lesson I learned is that as an entrepreneur, you have to be able to tell your story well—and frequently. It’s remarkable how much time you spend telling your story, whether to potential investors, employees, partners or the media. You need to seek out people with leverage and ask for their help in telling your story, as well.

What has surprised you about being an entrepreneur?

When I first started out, I took for granted the overall speed at which I thought things should happen. It turns out things happen slower in the short term and faster in the long term. As an entrepreneur, you are believer and so you tend to think your idea will be obvious and immediately transformative. But nothing happens at first, and not for a long time. You get 90% of the results in the last 10% of time. You spend so much time thinking about getting to the goal that you forget to think about what to do once you get there. You need to think 30 steps ahead.

What five adjectives would you use to describe yourself?

Passionate. Driven. Creative. Imaginative. Inspiring.

What values are important to you as an entrepreneur?

Devotion. A sense of possibility and an open mind. Resilience. Be yourself. Don’t try to be a clone of someone else.

What is the best business advice you’ve ever heard?

“Build the machine.” It means that in addition to focusing on building the product, you have to build the machine that builds the product. The machine is the human capital and the core values of the culture.

What is your motto?

As a kid I wore a couple of shirts in hockey camp. Both of them are relevant to what I do today. The first is a Wayne Gretzky quote: “Skate to where the puck is going not to where it’s been.” The other was “100% or nothing.”

Which living person do you most admire?

Steve Jobs. He changed the rules. He showed that someone with a liberal arts background can run a technology company and become a leader. That is what I want to do.

What are you passionate about?

Two things: Design and turning Airbnb into a movement.

What motivates you?

Achieving. Moving toward my personal vision of the future. What motivates you to walk is the place you are walking toward. What motivates to build a company is what you want the company to become. I would love it if someday people forget what life was like before Airbnb.

What was your first paying job?

Selling artwork as an illustrator when I was in school.

What do you like most about being an entrepreneur?

The freedom to change the world.

What do you like least about being an entrepreneur?

The dozens of things that threaten to sidetrack you from your goals each day. As an entrepreneur, you just want to move forward.

If you could change one thing about yourself, what would it be?

I would like to be more patient. Once I make a decision I want to go but often times you need to explain how you came to your conclusions in order to get buy in from other people. You want to say, “Trust me!” but you do need to communicate to bring other people on board with your plan.

What do you consider your greatest achievement?

Starting Airbnb.

What is the last book you read?

I’m currently reading The Innovator’s Dilemma.

What advice would you give other entrepreneurs on how to build a great business?

Choose a good co-founder. Develop deep, personal relationships with people who share your values and yet also have a lot of the skills you don’t have.

“Some of our customers call it a revolution; some call it a movement. We’re living in a peer-to-peer, collaborative consumption era and Airbnb is helping to propel that forward.”