Q&A: Brian Chesky on Airnbnb, future dreams, Niskayuna memories

A1 Chesky

By Indiana Nash

Gazette Reporter

SCHENECTADY- As Niskayuna families and almost-graduates filed into Proctors for graduation Thursday evening, there was a palpable feeling of excitement.

This year the anticipation wasn’t exclusively for the ceremony itself, but for one guest speaker who has been making headlines: Brian Chesky.

He’s a 1999 graduate of Niskayuna and the co-founder of Airbnb. The company started out in 2008 with a home-sharing business model and has since grown into one of the most powerful companies in the sharing economy. About an hour before the ceremony, at which he would be inducted into the Niskayuna Hall of Fame, Chesky sat down with the Gazette to talk about his business and coming back to Niskayuna.

Q: What’s it like to be back in your hometown?

A: It’s amazing, it’s really nice and it’s really small. I likened it to when you go back to your kindergarten classroom. I remember it was literally half the size. I have memories of being 5 years old and everything was really big, even my house. But it is a really amazing town and I probably took for granted how nice it was here because you go out in the world and not a lot of places are like this. So it’s nicer than I remembered and smaller than I remembered.

Q: Were you surprised when the school told you they wanted to induct you into the Hall of Fame?

A: Yeah, I don’t think you ever expect that. It’s more surreal. What makes it weird is I remember being just a regular student. If a random company asked me to go speak to them and I had no point of reference it wouldn’t be odd. It would be a speaking engagement. For your high school though, it brings back all sorts of memories. When these students were born, I was graduating, and so it’s the midway. Half my life ago, they were born. So I’m going to mention to them this thought: I’m old enough that they should listen to me but not so old that I’m their parents’ age, in which case they definitely won’t listen to me.

Q: Do you remember your own graduation night at Proctors?

A: I definitely do.

Q: Any funny memories?

A: Well, the funniest memory is a lack of memory. As I was writing the speech, I was remembering the person who spoke at my graduation and I thought deeply about it and what I remember from that speech is nothing. So then I thought “Will the students remember anything I say?” And they might not. So I’m going to tell them 10 things and then somebody will remember one of them. That’s my low bar. But I do think that you don’t remember all the words but I remember the feeling I had. It was a feeling of possibility and no one will ever forget that. They’ll never forget how they feel today even if they don’t remember what was said and I think that feeling of possibility is something I can contribute to.

Q: Even from the start, your vision (along with your co-founders) for Airbnb’s future was fluid. While the main idea of a bed and breakfast is still the company’s mainstay, it’s expanded into Trips. Why do you think you’ve always felt the need to grow the business into other services?

A: We have nearly 200 million people in the [Airbnb] community. This company started because we rented our three-bedroom apartment one weekend. You don’t go from there to 200 million people and you don’t usually dream of that. Your dreams are usually the next step in front of you. So it’s like “I dream of having my own company and maybe we’ll even have two or three employees” and you get that. Then you dream a little more. You kinda dream the next step, but maybe the bigger lesson is we started by renting air beds in living rooms but what we were doing was always the same thing: We were offering great experiences to people when they traveled. We just decided as we grew to offer more and more of that trip to more people and in more places.

Q: So what’s the next dream?

A: Basically, right now the vast majority of people still think of Airbnb as a place to sleep and my hope is five years from now people will think of Airbnb as a trip that had a huge impact on their life and maybe even changed their life, every part of it. The world will feel a little more magical because of the places you’ve been on Airbnb. We have hundreds of millions of people using the [Trips] service, so that’s really where we’re going. If all that happens, then we’ve accomplished or get closer to accomplishing why we do all this in the first place. Which is to say, we want you to feel like when you go to a community you should belong in that community. You should be able to belong in this world and not feel like an outsider and not feel unwelcome. We want to bring that to every home, every business and every community.

Q: Uber is often compared with Airbnb. Do you think Airbnb could ever be a competitor or possibly work with Uber in any capacity?

A: I think that we try to partner with a lot of companies in Silicon Valley and I believe we’ve done some things together. Nothing large. But we’re always open to partnering with other companies and I think the broader idea of Airbnb is really the sharing economy. It’s the idea that people can become entrepreneurs. So many companies are doing it and it’s a really special thing.

Q: Across the globe, legislators are trying to regulate the sharing economy. How has the company’s approach to handling legislators changed over the years?

A: Our response has changed because before we had any staff, we didn’t know how to deal with it. I thought when people don’t like you, you should avoid them because they don’t like you. And we hired some executives and they had much better advice for us which is “if they don’t like you, meet with them. Find out why, educate them, listen, learn about their problems.” That created a very collaborative partnership. We now have partnerships with over more than 200 cities around the world. We have teams that travel to hundreds of cities to have meetings, monitor misunderstandings, those sorts of things.

Q: On an emotional level, how have you learned to deal with those obstacles?

A: It can be intimidating when you have a challenge and you don’t know the answer and you can’t Google the answer. No one you know can tell you the answer and in fact oftentimes what you’re dealing with is unprecedented. So what do you do when it’s fairly unprecedented? You learn to trust your instincts. You learn to figure it out and you figure it out one step at a time. If you had to imagine sitting in a room and figuring out the entire problem, oh my god no one could do that. But all you need to do is figure out the next thing to do and that helps.

Q: Where do you think your leadership skills and qualities come from?
A: My mom and dad. They’re co-CEOs of the Chesky household!

Q: Earlier this year, Airbnb began offering free housing to refugees and anyone not allowed in the United States. Why did you decide to offer that? 

A: [At] Airbnb, our mission has always been about belonging and accepting people. To give you one point of reference, on New Year’s Eve we had 2 million people come from nearly every country in the world and live together. Never in the history would that have been possible. The idea of Airbnb is predicated on people being able to travel, people being able to enter each other’s countries and people being able to enter each other’s homes. And the primary idea is that if someone needs housing, our community should be able to provide it. This felt like the ultimate demonstration of it and we were firmly against the travel ban. We spoke out against it and our community was [against it] we were really probably speaking on the behalf of the majority of our community. We had such an outpouring of support. I did this little tweet and it had 200,000 likes and I don’t have a lot of followers so that was kinda crazy. Then thousands of people wanted to offer their homes Then we decided to run a Super Bowl ad, which essentially promoted the idea and we made a commitment to house 100 thousand people that need housing over the next five years. It’s a pretty audacious goal. Not a lot of organizations have done that before.

Q: You frequently quote authors and industry leaders. What is one quote that always comes back to you?
A: I’ll give you two quotes. My high school yearbook quote: “I’m sure I will amount to nothing.”  I remember bringing my yearbook home one day and my dad opens it, sees my name, sees my quote and he yells “Nothing?” He was really upset and  I just thought it was funny because it was ridiculous and he took it much more seriously than I did. But a more serious quote that would be an opposite of that would be Walt Disney: “It’s kinda fun to do the impossible.”

Q: If you’re out in public and someone finds out that you’re one of the brains behind Airbnb, what’s the usual reaction?
A: It depends on whether they had a good experience or not. Usually, they’ve had a really good experience and they’ll tell me about their trip. They’ll say “I host” or “I’ve traveled” and they’ll thank me. Every so often, someone will tell me about something that happened and they’ll ask for travel credit but that’s pretty rare. Often they have an idea. They’ll say “Thank you, Airbnb is awesome but it would be even better if . . .” And actually, I’m pretty shameless about taking the ideas. They’re good ideas.

Q: There has been a lot of back and forth on the company going public. Earlier this year, Fortune reported that you’re in no rush to have the company go public. Does that still stand today?  
A: We certainly haven’t ruled any event out. I think it was more than a year ago, we said it was a two-year project so just to be ready. We’re working so that if it’s in the best interest of the company to do it, then we’ll be ready. But we don’t have anything to announce right now.

Q: What are some places you like to go back to in Niskayuna, Schenectady? 
A: Saratoga. We used to go to the Saratoga race track. We’d go to breakfast at the track and then we’d go to SPAC. I remember it was 1997 and I saw my first Dave Matthews concert. Actually, my first concert, it would have been like 1986 or 87 — I was 5 — I saw Ray Charles. That was a pretty cool first concert. So summer in Saratoga is awesome and I used to go to the Scotia movie theater. Crossgates Mall was where I hung out. I don’t know if kids hang out at malls so much anymore, but back in the ’90s, they were the thing.

Q: I know you’re going to share 10 life lessons with the graduates, but are there some you had to cut out?
A: Other than the 10? Like a secret 11th?

Q: Right. A secret one that you wanted to mention, but you needed to make it an even 10.
A: Yeah! I’ll give you this one: When I went to RISD [Rhode Island School of Design] I had a teacher and he said “Brian, you’re a designer. Things around you were made by other designers.” Basically you can design the world you want to live in. It’s kinda odd because you tend to grow up thinking you’re in other people’s world. No one really tells you that everything around you can change. Of course, it can. But people don’t tell you that growing up, not often enough.