Connecting people has always been a passion of Brian's, whether it was rallying students at RISD for NADs hockey game, or developing a platform to share spare rooms and couches.
That interest, coupled with a smart sense for business, pointed Brian along the path of entrepreneurship where he went on to co-found Airbnb, a marketplace for unique spaces.
In this interview, he talks about life before Airbnb, when he was just beginning to find out what he enjoyed doing most and how he was able to make that his work.
See more of his work:
WHY HE MAKES
Carly: What's the first thing you made that you were proud of, whether at school or before college at RISD?
Brian Chesky: The first thing?
C: The first thing you were proud of that you made.
BC: So, growing up, I created a lot of artwork. I don't remember what maybe is the first thing, but I remember when I was like five, six, seven, eight years old, there were pieces that for the first time I realized this exhilarating feeling of what it felt like to create something. I have the control to create something that I pride myself in.
It was the ability to take something that was inside me, and then essentially put it on a piece of paper. So it would've been like maybe… I can't even think of what the artwork would've been, but it would've been something like in my sketchbook. I used to carry a sketchbook everywhere, so yeah. It would've been like in grade school.
C: Was there a moment when you knew that you wanted to go to college to make things?
BC: When I was in high school... I think when I was in eighth grade, ninth grade, I started to realize things that I'm probably going to be an artist, so I didn't know exactly what was up next. I went to a public high school. I went to a private school and then I had to transfer to a public high school and from there I remember it was around tenth grade. I started making these different pieces of artwork in maybe eleventh grade and it was by that point that I started to realize that this is what I was going to do.
I did a summer program at Skidmore when I was, I think, fifteen. And I went to Pratt when I was sixteen. I never did RISD's precollege, but I did the other ones. And they got me further and further immersed in it, and at some point, by the end of my junior year, I transferred to a public high school.
Our teacher, my art teacher at the time—I always remember her name—Ms. Williams, she basically told me that I should consider going to art school. She thought my work was really special or special enough to do that. It hadn't really occurred to me up until that point, so kind of late junior year into my senior year she entered me into a couple competitions, art competitions. One, where I won this award where I was recognized nationally. I had my work in the capitol building in the gallery of Washington DC, and I started becoming known around my town or my area as an artist.
That started becoming my identity in all I did. I remember being really inspired by Norman Rockwell. I really loved him, and he was someone I looked up to. Growing up, my parents used to drop me off at the Norman Rockwell Museum. I'd spent the day there. And I loved him because he felt like he was certainly an artist, even though he was kind of an illustrator. So I don't know. That was kind of what I did.
C: Is there any experience at RISD that really stood out out to you and let you know that this is what you wanted to be doing, or some particular teacher who had a huge influence?
BC: Oh, yeah. Yeah, there were tons of teachers and tons of people who had a lot of impact on me. I remember we had some crazy projects. There were so many projects where they really unleashed my creativity. Freshmen year, I was somewhat impacted by at. I think it wasn't until I got to enter my department there that it really, really challenged me, and we would have... Let's see. I'm trying to think of some projects we had..
I took, for instance, I did the MIT program with Matt Kressey and that had a pretty profound impact on me. I also... Like, even within the RISD ID department, I helped put together the Industrial Design show, the senior show. We used to do these day projects, like challenges. I think those were really, really cool and interesting.
I was very involved. I have to totally jog my memory of all of this, of the times of my days at RISD now. I ran the NADS hockey team.
And I was the co-creator of the mascot, Scrotie.
BC: That was my greatest creation yet. For us at the time he was the symbol of self expression.
C: Can you tell me more about that? I've always been curious about how Scrotie came into existence.
BC: How did that come to be..? I helped run the NADS Hockey Team. My two friends and I took over the hockey team part of our way through our freshman year. And the team wasn't doing really well. We were kind of on the verge of being cancelled. It was just not organized at all. We created the uniforms that I think they still have today, the pucks, and the stick and that logo. We created that logo.
BC: We tried to turn it into a real brand, you know. We really wanted to build a real brand, and we wanted to build the kind of thing where people all over campus would come to. We really wanted to raise awareness for the team, and we felt we needed to get cheerleaders. So that's when we came up with the 'Jockstraps,' so they support the NADs.
BC: We felt like the cheerleaders without a mascot, it didn't make any sense. We really felt like this team needed a mascot, somebody to represent them. And we wanted somebody or something that would be the spirit of RISD.
It was almost a little bit of a mocking of the sport, but not completely. It was just a fun play, like, completely rethinking of every part of the team. We felt like the mascot had to be bold and take a creative challenge to the next level. We wanted something that might just surprise people, shock them. I think when we came up with Scrotie, I think we achieved those goals.
Even 10 years later, he seems kind of shocking. I can tell you 10 years ago, or 12, 13 years ago when we came up with it, I mean, I thought it was going to get us kicked out of school. It's a testament to RISD that they didn't kick me out of school for it, but I wasn't sure.
I thought either it was going to be the greatest thing that RISD ever did or a huge embarrassment, and I couldn't tell which one it was.
I was pretty sure it was a really good thing because it literally was not making fun of our program, but it was a statement on every other athletic program in the country and college sports. I thought it was really funny, and we wanted to take the NADS, turn them into essentially entertainment and a collective way to capture the spirit of RISD and bring everyone together.
I guess that was, for me, another one of my forays into entrepreneurship, bringing people together. We had a huge marketing challenge of trying to get designers to come work for us because that's typically not their interest. For me, that was something in particular and, oddly enough, that I'm pretty proud of that I got to work on. Actually, I'd say that taught me as much as anything I ever did at RISD, maybe more.
C: That's excellent.
BC: MIT was the other thing that was really, really amazing. It was a great program. My project was a sugar dispenser. I had to redesign a sugar dispenser and we created a sugar dispenser. That program for me had a big impact on me and my life.
C: In what way?
BC: Just like the NADS, it made me—I was entrepreneurial. I just didn't know I was being an entrepreneur. Does that make sense? I was just kind of doing things and the MIT course really reminded me, "No, I actually am an entrepreneur." They actually called it like an entrepreneurship program. It was one of the first times I really worked closely with engineers and I got to actually build a product—everything from idea to building a product and thinking about how that product would go into the market.
As soon as I did it, I felt like I really excelled in that class and I felt like I had discovered, between that and the NADS, I discovered what I wanted to do with my life. I was really obsessed with creating.
I think an artist is in many ways an entrepreneur.
Entrepreneurs and artists—they both have control. An entrepreneur's meeting with the business and an artist is meeting with the piece of work they're creating, but they can both serve the same goals, and they became very interchangeable to me. I had to realize there was a fine line between being an artist and entrepreneur.
They're kind of the same thing, especially because the MIT and the NADS thing. They were organizations and I started realizing that my canvas didn't really have to be a piece of paper or an actual piece of canvas. My canvas could be a community of people or a physical product. With the NADS, it was a community, an idea, the movement, which is kind of what entrepreneurship is.
It was, to me, a sense of personal self expression. It was really an important thing. We did a lot of crazy things. And that's how I met Joe Gebbia because Joe, my co-founder, was running the basketball team, the Balls. So we were like, you know, kind of two entrepreneurs on campus.
C: So what other lessons do you think could you relate from either the MIT studio or working on the NADS that you use every day at Airbnb?
BC: Very, very good question. I would say that, with the NADS it was this notion of having a vision. It was crazy, but had a vision for what it could be, what the team could be, and what it meant for the campus. The NADS went from being a barely organized hockey team to something where we would have thousands of people in front of this tiny arena
It really taught me a lot about bringing people together and then telling them an inspiring story or vision. I really learned the value of storytelling and the value of having a very clear vision about what you want and being able to very succinctly, effectively tell that story to other people. I worked on a number of other things that impacted me. The NADS was a really important one, and then MIT for me, I was able to practice that into a real business.
I was able to ask how does this translate to a real business? How do I actually make and manufacture something and turn it into a real business? And it really gave me the confidence to realize that I actually could be an entrepreneur and learned to write a business plan and a bit more about how to run a business because the project we worked on I actually pursued. I entered an MIT entrepreneurship competition after I submitted and I thought it could be a pretty compelling product.
C: How did the competition go?
BC: You know, we did fine. We weren't competitive. We had a redesigned sugar dispenser, and people who entered the competition were like new patents or new ideas for like drugs or new technology.
Airbnb would've actually done better if we had entered and back then. But a sugar dispenser company was not compelling by MIT standards.
It taught me the power of presenting, especially in my department. I have done tons of presenting. And, by the way, the amount of presenting and storytelling I do today, so much of that came from RISD. It really taught me how to do that. I also took a public speaking class, which profoundly effected on me. [Scott Club], he was an English teacher. I don't know if he's still there. He had a big effect on me. Some of my friends and then the NADS team. These are just some of the people that I remember. There were others as well, of course. He was one of the ones that I remember.
C: And what's the last thing you made?
BC: The last thing I made... So depends on how you define that because I'm still making things. So if you mean, like, the last thing that I made as an individual contributor or last thing I collaborated on?
C: Last thing you worked on.
BC: So I would say the last thing I worked on was... I have so many things. The last thing that's public would be the Neighborhoods Project, and I was just a contributor on that. I'm working on a ton of new things now, but that was probably the last public thing I worked on. I spent a good amount of time with the team trying to get that product to be really simple. We wanted to tell the story.
Of course, I by no means deserve even a minority of the credit, but I worked on that with the team and spent a lot of time on it. Our vision was: what if we could tell the story of a neighborhood? Just simply tell the story of it. A neighborhood story. I think every person has a story. Tell their story. Tell it and show it, rather than tell it.
RISD taught me the value of showing, not just telling.
I really learned the value of storytelling and the value of having a very clear vision about what you want and being able to very succinctly, effectively tell that story to other people.
I think an artist is in many ways an entrepreneur.