Co-Founder, Chief Executive Officer, Head of Community & Chairman of the Board, Airbnb Inc
Lost Early Interview of Brian Chesky & Joe Gebbia on Airbnb’s Early Days (2010)
A rare early Airbnb interview from around 2010, featuring Airbnb founders Brian Chesky and Joe Gebbia in conversation with Jessica Livingston, co-founder of Y Combinator and author of Founders at Work.
They discuss Airbnb’s early startup story, how the company got started, what went wrong, what surprised them, and the lessons from building one of the most important marketplace startups of the internet era.
Guest: Brian Chesky and Joe Gebbia, co-founders of Airbnb
Host: Jessica Livingston, co-founder of Y Combinator
Series: YC Founders at Work
Originally recorded circa 2010
Topics: Airbnb ea...
About Brian Chesky
Brian Chesky, co-founder and CEO of Airbnb, has been discussing the company's expansion beyond home-sharing into a broader travel ecosystem. In a series of interviews and events, including the company's 2026 Summer Release, Chesky announced new in-app services such as grocery delivery, airport pickups, luggage storage, and car rentals. He described the company's goal as composing "the entire end-to-end experience" of a trip, stating that "you don't necessarily always remember the place you stay, but you're going to remember what you do on your vacation." Chesky cited Amazon's model of category expansion as an inspiration, while emphasizing that Airbnb's "organizing principle" remains travel and the trip. Chesky has also highlighted India as a key growth market, saying the company is "playing the long game" there and that he expects India to be "one of the core engines of growth for travel." He noted that Airbnb's largest office outside the U.S. is in India and that domestic travel already accounts for most of its business there. Regarding the upcoming World Cup, Chesky stated it will be "the biggest event in Airbnb history," with over 700,000 guests booked across the three host countries, including 180,000 in Mexico. On the topic of AI, Chesky said he views it as an "accelerating technology" that will "speed every single thing up," and predicted that "pure people managers" who are not hands-on will have less of a role in the future. He also addressed a congressional inquiry, stating that Airbnb is cooperating directly with the committee and that all company data is "vaulted" with no external access.
Transcript (73 segments)
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Jessica Livingston0:00
Hi everyone, I'm Jessica Livingston. I am a partner with Y Combinator and the author of Founders at Work. Lots of people have suggested to me that I do Founders at Work-style interviews but with Y Combinator founders, and this is a great idea but it's so time-consuming that I never really got around to it. So when I was watching Andrew Warner's interviews on Mixergy, this sort of inspired me — what a great idea, this could be the perfect format. So this will hopefully be the first of a series of interviews with Y Combinator founders.
The big problem I was trying to solve with Founders at Work was that there was a whole bunch of information trapped in the heads of founders and I was trying to get that out for the world to see. Now, Y Combinator has funded 172 startups, so each one has an interesting story, and the Y Combinator founders are so great about helping each other out and sharing all kinds of advice and stories for the new groups that come in. So I wanted to try to share that with future startup founders. I just want to thank everyone at Justin.tv for setting me up and giving me the royal treatment, especially Randall Bennett who just went above and beyond the call of duty. So thanks.
So I'm here today with Brian Chesky and Joe Gebbia. They're two of the founders of Airbnb. For those of you who aren't familiar with the site, the easiest way to describe it is as the eBay of space. Using Airbnb, anyone can rent out any space that they have, whether it's an extra bedroom, an entire apartment, or even an air mattress on the living room floor. We funded them about a year ago and they're just doing fabulously. So hi guys, thank you for being my first interviewees.
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Brian Chesky2:01
Hey, how are you?
J
Joe Gebbia2:02
I'm doing well.
J
Jessica Livingston2:05
Before we even get started, tell me about this backdrop that you have. It's fabulous.
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Brian Chesky2:12
Well, the backdrop that you're looking at is the results of a brainstorm that we had — a company-wide brainstorm last week. We brought everybody together and we just started to brainstorm some really fun ideas for certain sections of Airbnb that we're looking to improve. So there's a lot of ideas, a lot of creativity.
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Jessica Livingston2:32
Well, I love it. So how I usually get started with people for Founders at Work is that I ask them to take me back to when their company got started. But for you guys, I'm going to ask you to take me back even further because the story of Airbnb, I know, starts about a year before Airbnb started.
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Brian Chesky2:55
Yep, it did. So it literally all happened in this apartment that we're sitting in. For the people watching this, we're not seeing an office — this is our office, but it's actually a three-bedroom apartment. This is the reason we actually started this business. Joe was living here in San Francisco in this apartment, I was living in Los Angeles. Joe's other roommate here who they met on Craigslist was Nate Blecharczyk, a third co-founder. And the concept hadn't started yet. I literally moved up here from Los Angeles and here we were — we had maybe a month of runway left. We had very little money in the bank and we had to figure out how we were going to make the next rent check.
Our story is a little different than some of the other YC companies because we hadn't been aspiring to start a company or get funded by Y Combinator for a really long time. We were completely independent of that. There was a design conference coming to San Francisco and here we were thinking we need to make money, we need to meet people, because if you don't have a job you better start networking. So we put the two together and decided why not create a little designer bed and breakfast for these people coming to this international design conference. It happened to be that first weekend coming up when Joe and I first moved in together.
We noticed on the conference website that all the hotels were sold out. They had listed like three or four hotels and they all said sold out.
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Joe Gebbia4:22
Big red letters. Sold out. Sold out. Sold.
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Brian Chesky4:24
And that was the light bulb for us. It was like, well, why don't we create a little designer bed and breakfast? We pulled out a couple air beds and we had the original idea: Air Bed and Breakfast. And what we always tell people is we weren't trying to start a business. We were trying to solve our own problem. And we did.
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Joe Gebbia4:40
What happened next, Jess? It was pretty amazing. We learned some lessons early on on how to get press, and we took that little rinky-dink website airbedandbreakfast.com — an 18-character URL — and we sent it out to every design blog that we knew on the internet. When we woke up the next morning, we were posted on Core77, SwissMiss.com, some of these prolific design blogs around the internet. The conference organizers, the IDSA, even endorsed us and emailed all the conference attendees about what we were doing, because the problem was that big — there was actually no place to stay in San Francisco. So the solution that we came up with simply to pay our rent was actually solving the problem for all these other conference attendees coming to town.
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Brian Chesky5:26
And we hosted three people, and the three people that we hosted changed all assumptions about our website. When you're starting a company, anyone can tell you that the users they thought they were starting this business for may not be the users they end up with, because they have certain assumptions. Our assumption was that this was a business that other people like us — other guys early 20s — were willing to use. Backpackers, people with no money, really young people. The idea that somebody over the age of 30, the idea that a woman would stay with a couple guys — I don't know, a lot of our friends didn't think that was going to happen.
The three people stayed with us. The first person was a 35-year-old woman from Boston — immediately broke our assumptions. A woman over 30 — okay, there's maybe a bigger market here. The second guy was a designer from India. He had scoped out our site, he was a huge fan, already a passionate user, and we had just come up with the concept like a day ago, which is amazing. And the third guy was a 45-year-old father of five from Utah. As soon as that happened, we said there's absolutely no — these are three totally different demographics. One time is a fluke, but there's obviously a bigger market here.
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Jessica Livingston6:44
Wow, it's kind of funny because it encapsulates two of the bits of advice we give, which is to make something that solves your own problem, and also you never really know how people are going to use your site until you actually launch it, right?
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Brian Chesky7:01
If you had asked us a month before if we could predict that a guy would pay $80 a night to sleep on our kitchen floor, I would have told you you were crazy.
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Jessica Livingston7:11
Okay, by the way, I need to apologize if I seem a little bit off. It's because I've done tons of tests on this and everything's always been fine, and right now there is this crazy echoing going on and I can barely understand myself. So I apologize if I seem a little bit stiff. But tell me — you launched the site, you have three guests come that weekend. What are the next big turning points for you guys?
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Brian Chesky7:37
So we literally weren't trying to start a business. Created this tiny website, Joe and I, in a couple days, launched it. Here we were — we made close to $1,000. We had an amazing time, these three people that we went around the whole city with, basically created some new friendships. At this point we started reevaluating. Maybe Air Bed and Breakfast wasn't a way to make rent one weekend. Maybe there were other people that would be interested in doing it.
A couple little design blogs had picked it up, other people started saying that's such a cool concept. And the way you know something's good — we'd go home for Christmas, this is a couple months later, and this is how you know something's good: when you go to a party or you're with your relatives or you're with an average person and they ask you what are you up to, and of course it's not just one thing because when you're not doing just one big thing you're doing like three things. So we'd each tell them, 'Oh, we're doing this and we're doing a little consulting, we're doing this.' And then we get to this other thing, Air Bed and Breakfast. They say, 'What? What's that?' It would completely monopolize the conversation. Here you were just trying to tell them a few things we're doing and suddenly the whole dinner table wants to talk about that.
You start to realize maybe that is what we should be spending our time on. If everyone else seems to think it's interesting, they start saying, 'I would do that.' On top of that, Jessica, I remember specifically getting emails from South America, I got an email from London, I got an email from Vancouver, an email from Japan. And these are people who read about us on the internet and they wanted to participate in this idea of airbedandbreakfast.com.
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Joe Gebbia9:13
And I think it was those emails along with what Brian just said that kept us going with the idea — there actually is something bigger here. People want this. They keep writing us about it.
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Brian Chesky9:22
So basically what happened next is we realized we wanted to build a site where you could book a room anywhere around the world. But to start off with, we had this kind of fear — there's a bit of uncertainty. We didn't know if people would be comfortable booking rooms with strangers all over the world. And since we launched at a conference previously, we said why don't we instead create a site where you can book housing for conferences all over the country. So that was the original concept.
We needed to get another person to help us build the site. Nate happened to be Joe's old roommate. I remember looking at Joe and saying who's the most talented engineer that you know? Nate was the person. He happened to be brought together through the proximity of this apartment. We brought Nate on and we basically created the next version of the site to provide housing for South by Southwest. This was in March of 2008.
I remember meeting the guys at Justin.tv and we saw all the success they were having. We figured, oh, we're just going to build this site and a couple months from now we're going to have like the traction that Justin.tv has. We're going to have millions of users, everyone's going to love it because it's such a good idea. And all I can say is that that was the beginning of a very, very long road before we actually started getting a lot of traction.
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Jessica Livingston10:47
So we sometimes refer to this period where you're not getting a lot of traction as the trough of sorrow. Can you tell me a little bit about how it felt and how you kept yourself going through this time? Because a lot of founders would give up.
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Joe Gebbia11:03
The trough of sorrow was a very generous term for this time of Air Bed and Breakfast. Because as Brian mentioned, we thought the market opportunity was housing for conferences, and that's how we labeled the website — Air Bed and Breakfast, housing for conferences. We thought we would target conferences around the country, around the world, and people could post rooms to those conferences and then travelers could book those rooms and we could make a great connection and people could sleep on air beds and save money.
What happens though is that conferences have an end date, and at that end date they're over until the next year. So what we found ourselves doing was marketing in a hamster wheel from conference to conference. We put all this effort into marketing to a specific event, and when the event's over, all those rooms that had been posted to our website were lost. So we found ourselves just kind of overworking ourselves, really just trying to get the website to stick. We totally believed in the idea, we knew that one day people would use this, we just needed to find the right sort of application for it.
And that brings up a great story that Brian has about his trip to South by Southwest, which fundamentally changed the website forever.
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Brian Chesky12:05
Yeah. This is the first time we really used it as travelers, right? Remember, we started the site as hosts to make money. So for South by Southwest in March of 2008, we decided to use it now as a traveler.
And remember at the time — now on Airbnb, you can just put your credit card in and book a room anywhere around the world just like you're booking a room on Orbitz. It's not too much different. But back then it was a bit closer to Craigslist. In other words, we just connect you with people, then you would message them. We didn't even have a robust messaging system, so you'd eventually email them and you'd have to work out the payment. Basically you'd have to show up with money.
So I booked a room with this PhD candidate from University of Texas at Austin named Tiandong. He was this Vietnamese student, a really cool guy. He picked me up at the airport. He and his girlfriend had prepared a traditional Vietnamese dinner for me, they had this nice air bed laid out in their living room, and it was awesome.
But then an inevitable awkward scenario happened. He asked me, 'Okay, where's my money?' And he didn't ask it exactly like that, but it did feel a bit awkward. And I remember telling Joe afterwards, we have to really address this. Of course, looking back now, it's a great business model — handle payments through the site, take 10%, you have a business model from day one. But that wasn't how we were thinking about it back then. We were thinking, man, this is going to be really weird if we end up becoming really big and we have all these users just exchanging cash in person. What value are we really adding?
So we took that experience, Jessica, and two things surfaced to the top. The first was that it's super awkward to exchange money in person, so let's bring it online with a credit card. And the second thing was more emails started to flood in. I remember we got written up on Mashable and some other tech blogs based on our South by Southwest site, and we started to get a flood of emails from people all around the world. People were saying, 'I want to list my room or travel through your website but there's no event taking place. How can I do this?' And so we started to broaden our perspective of what the site could actually be.
We said two things are going to change for the next relaunch. We're going to make it really easy to pay online with a credit card, and we're going to open it up to be a travel website. Events can participate if they want to, but you don't have to have an event in order to travel or host on Air Bed and Breakfast.
I also want to make one random comment — you can't tell because we're not going to move the camera, but where we're sitting right now, we're sitting in an actual bedroom. Part of the company works in this bedroom, this is soundproof. Anyone working on the phone is in this bedroom. Behind us, behind this wall, is a living room, and that's where the rest of the company works.
The reason I bring this up is that this bedroom was the bedroom of our old roommate Phil, and Phil worked for Justin.tv. So you ask us what was our connection to Justin.tv — it was because one day we randomly met a guy on Craigslist that needed a bedroom. And this was separate from Air Bed and Breakfast, this was actually before Air Bed and Breakfast. Joe, this guy Phil, he's working for Justin.tv, he ends up becoming a roommate, and so here independently we start this website.
We find out that Phil is working for this company that is getting a ton of traction. We didn't really know what Y Combinator was at the time, and that was pretty much our introduction to the startup world. We did not come from a background — you know, that was really our background. And I remember at that point we then met up with Justin, Michael, Emmett, and the guys, and it was over the course of that summer that we really got an inside view of what it would be like to have a real startup. I remember we'd go to their offices and they had like 10 or 12 employees at the time — that seemed like a ton of people when you're just two or three guys struggling in your living room.
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Joe Gebbia15:56
And so they were really important to us. Over the course of that summer, we basically said, okay, now we're going to build a site where you can book a room anywhere around the world with three clicks — three clicks to a book button. That was the vision. And so I think everyone thought that was awesome, and the next thing people said is: when we said we're going to build this amazing site, three clicks of booking, it's going to be so easy to use — everyone says that makes sense, but how are you going to get people to use it? In other words, it's a marketplace. Anyone who knows anything about marketplaces knows the hard part is the chicken-and-egg problem. Buyers only want to go where sellers are, sellers only want to go where buyers are. It was a really, really challenging problem.
For a few months we didn't know how to crack it. We're really chopping away at this point. I think my bank account was in the negative zone. We're probably living on credit card debt for months at a time. It was really, really challenging. We just believed so much in this idea that things like that were distractions — we weren't letting that stop us because we knew this opportunity was so big.
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Brian Chesky16:58
I remember one day we're sitting at home and we see this blog post with a photo of Barack Obama in Portland, Oregon. This was during the Democratic primaries and he's speaking in front of 70,000 people. At that time, all the candidates were speaking in front of like 5,000 people. So this is the first big speech he had, so many people. Everyone started saying this is a phenomenon, it's in the beginning stages. And then it became clear he was going to win the nomination.
When it became clear he was going to win the nomination, it also became clear to us: opportunity right here. We started noticing there were news articles — housing crisis in Denver, there are 27,000 hotel rooms. Barack Obama is getting such big crowds that they're moving him from the Pepsi Arena, which is 20,000 people, to this huge 80,000-seat Invesco Field. So the New York Times, CNN, they're all doing these headlines: housing crisis in Denver. At that point we said, that's our chance. What we're going to do is we're going to get a ton of press by having a high-profile answer to a high-profile problem.
It was within a matter of a couple weeks that here we are sitting in a living room with no money, just a tiny little website that no one ever heard of, to a few weeks later sitting in a living room with no money but we were being interviewed by CNN and the New York Times. So it really changed our trajectory.
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Joe Gebbia18:17
Yeah, it was pivotal that we timed the launch specifically with the DNC in Denver. It was a big, big problem as Brian just said, and we ended up getting close to about 800 or 900 people in Denver to list their properties on the website. This is the first time where we actually had serious inventory, serious selection. So people were coming to the website and they could actually find what they were looking for, whether their family was coming to the DNC or an individual traveler. So we got our first taste of what the website would be like if we actually had 800 listings in every city around the world. And that was enough to inspire us to keep going forward.
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Brian Chesky18:56
The wiggles of hope.
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Joe Gebbia18:58
The wiggles of hope. And that was a little wiggle for sure.
J
Jessica Livingston19:03
So the Justin.tv guys told you about Y Combinator, right? Is that — are they the ones who encouraged? How did that happen?
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Joe Gebbia19:12
We have to give them a lot of credit. Yeah, they exposed us to the Y Combinator philosophy, I guess you could say, in the sense that they were so giving. Here we were, two design guys who didn't know too much about starting a web startup, and they really took us under the wing and said, guys, these are all the mistakes you're making. If you want to correct them, you have the option to do these different things. They really just were very giving of their knowledge and very open to meeting with us. And it's very reflective of Y Combinator.
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Jessica Livingston19:48
So you apply and I remember our interview. I remember specifically you showed up with the cereal boxes.
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Brian Chesky19:55
So this leads into — yeah, I think we can transition from the DNC to the start of Y Combinator. And in between the DNC and the start of Y Combinator — yeah. So a lot of companies fail because even though — here's the thing, right? You have this amazing idea, you're working for so long, for so long you have no money. But what keeps you hopeful is that you're going to launch on TechCrunch, you're going to get this huge spike, everyone's going to know about you and you're going to be living happily ever after. Right? That's what keeps you going. The hope.
Very few people — some people never even get to the launch, they quit. But a lot of people get to the launch, they get a ton of press, and then you guys have this famous graph where it goes like — you're struggling, you get this TechCrunch spike, and then you crash, right? And then you find out where your real traffic is and then you've got this really long trough of sorrow. And that's the true trough of sorrow. The one before you launch is just get your product out there, release. And then after that — so here we were, we were so excited at the DNC, we had all these people using it in Denver, and I remember it was so exciting. We were at the Democratic National Convention, we come back to San Francisco and we had no users. Our entire user base — it was back to almost nothing.
So we had to basically figure out, okay, we made a little money for the DNC, we have more rent checks coming up. We hadn't taken any investment at this point, and it was absolutely no business going on. I remember at the time we were talking about for fun what would we do if we could give hosts a little breakfast kit or something that they could give to the travelers coming to the Democratic National Convention. We did the same thing for the Republican National Convention as well. And we decided it would be a non-perishable breakfast. Well, what is a non-perishable breakfast? It's probably cereal. There's not many other things you could do. And the great thing about cereal is if we designed these cereal boxes, it'd be very easy to brand it.
So this was mostly for fun — we weren't thinking this as a huge business opportunity, it was just for fun. We were sitting late at night one night and we were thinking, what would a Barack Obama cereal look like? What would a John McCain cereal look like? And so for Barack Obama, it was just so obvious — Obama O's, right? Barack Obama would be Obama O's, the Breakfast of Change. And Captain John McCain — he was a captain in the Navy, so it would be Captain McCain's, just like Captain Crunch. So we started designing this box, and before we knew it, because we're both design grads, we had this really, really cool design box.
One thing led to another and we ended up collaborating with an illustrator, a photographer, a printer, and we put together the now-famous Obama O's and Captain McCain's cereal box collector's items. And we proceeded to not only sell these on the internet, but we sent these to every major press outlet across the United States. So Jay Leno has a box of these, Oprah has a pair of these boxes, NBC — name a press outlet, they got a pair of these boxes. We thought it would be great exposure for the website. That's why we made the box.
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Joe Gebbia22:58
Yeah, and there's some really cool stories about the box itself. First of all, here's like a secret to getting press: if you want to get press for something, imagine if we just emailed somebody a screenshot of that cereal as compared to somebody in the mail getting this, right? And then you suddenly open this and it's on your desk. Not everyone that we mail these to did we get stories from, but of course TechCrunch picked this up. This went on CNN, it was on the Today Show, it was in Fortune magazine. It was on like 30 or 40 different local news stations all around the country.
And the coolest part about this is that these cereal boxes — we sold them because they're collector's edition, right? They're all individually numbered, and we sold them because they're not just regular cereal boxes, they're really premium boxes and there were very few of them. So we sold them for $40 a box, and we weren't sure if we'd be able to sell very many. But because we couldn't do a big run, we couldn't just sell them for $4 — we're like, you're not going to open these, you're going to save these because we've spent so much time on them. Sure enough, because we got all this press, we end up selling 800 boxes. That's over $30,000. We sold $30,000 of cereal. The cereal actually gave us more funding than Y Combinator when you think about it.
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Brian Chesky24:23
So it's actually pretty funny. I remember at one point my mom asked me — because the business was making really not very much money, the cereal made us all this money — at some point Mom asked, 'Are you guys still a website? Are you a cereal company now?' And at some point there we had to think about it.
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Joe Gebbia24:38
People were very confused at this point — what kind of company are you? We're peddling cereal on the internet and we're trying to get a web startup going. But I think this speaks to the nature of our company, the way it's run. We're extremely frugal because we started with nothing — we literally had our credit cards to run our company off of from the early days. So we've always had to get creative to figure out ways to make money.
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Jessica Livingston25:05
You guys hustle, that is one thing that is very distinctive about you guys. About your art backgrounds — you both graduated from RISD. What have you done in addition to designing these gorgeous cereal boxes? What else have you done from a design standpoint to help make Airbnb so successful?
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Brian Chesky25:24
Well, I think one of the greatest contributions that we make — I think there's maybe two major contributions. One is to the general travel industry, if we can hopefully turn it on its head and make people think about the space differently. I think another big contribution that we can make is to change the perceptions of what the importance of design is to a startup. I've heard — I get this impression from other companies — that sometimes a designer is thought of as a headcount. You hire a designer and they do design. And what they mean by design is making it look pretty or making it look nice. And we don't think of design as something that just makes it look nice. Design isn't how it looks. Design is how it works.
Steve Jobs himself said design is how it works and technology enables that to happen. So when we're coming up with things, I think that's the most important distinction, because two of the three founders are designers. We're really thinking about problems from a design perspective.
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Joe Gebbia26:29
What's really unique, Jessica, is that both Brian and I studied product design or industrial design. And when you focus on industrial design — designing the product — you're really designing an experience, and it just takes the shape in the form of, fill in the blank, a computer mouse, a laptop, a shoe. And I think a lot of those same principles that you're going through your mind as you're designing an experience for somebody as they open a package and pull a product out and turn it on for the first time — the same thing is running through your mind as you're thinking, okay, somebody comes to our website to search for accommodations. What happens next? And you're just in this mindset of: how can I make this experience so easy for them, so simple that they don't have to think about it.
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Brian Chesky27:11
Design allows you — or it trains you — to empathize with your users. You're constantly putting yourself in their shoes, thinking, if I were them, what would I be feeling right now? What would I be doing right now? And so, not to say that we're not analytics-driven or metrics-driven, but we also do a lot of things that designers do. They do a lot of field work — going into the field. So what was our version of that? Well, we told this a little bit on our Mixergy interview, and part of it was inspired by Paul Graham. We generally believed this anyways. We just thought because no one else that we knew in startup culture was meeting their users, wasn't getting their hands dirty. Paul Graham really gave us permission.
What did Paul Graham tell us to do? Paul Graham told us do things that don't scale. It's kind of a designer's philosophy anyways. Our background is in industrial design. I remember one of the things I used to design was medical equipment. So if we were designing medical equipment — this is actual hardware — you would go to the hospital, watch the patients, you would observe and you'd try to empathize. Maybe you'd be lying down on the table. You wouldn't just be giving them five samples and doing A/B testing. You would actually have to put yourself in their shoes.
We decided we had to do that with this company as well. Our version of that was we went to New York City during Y Combinator — this is kind of leading into where Y Combinator started taking off. I remember we're sitting in Mountain View, California, at where probably you are now, and we're meeting with Paul Graham. He asked us, 'Where are all your users?' And at this point after the DNC we didn't have a lot, but the few that we had were in New York City. We said, 'Our users are in New York City.' And we're talking about how our users are meeting in person.
And he says, 'So all your users are in New York City, that's where you're making all your money, but you're here in Mountain View. Why are you still here?' And I kind of almost went over our heads — like, what do you mean why are we still here? It's like, 'Why are you still here? Go to New York.' And of course this is in the context of we told him we went to Washington DC for the inauguration, we told him how we did a party, a meetup, kind of a Yelp-style meetup. We met our users. He said, 'Do the same thing in New York.'
We went to New York and we decided to do one other thing. We wouldn't just have a party, we wouldn't just meet our users. Because we're both designers, we'd take photographs of their place. We knew how to take really great photographs. And the excuse of photography was basically to let you into their homes. And so over that process, you'd be sitting there, they'd tell you about the space, how they were having rent problems. They'd tell you their story. They'd pull up the website, they'd show you them using it, and like all the problems they're having. They were never going to email you this — you can have a big feedback button on your website, you're not going to observe things because they didn't know they were doing those things. You had to observe them. And so that was the fieldwork that we did.
This was again Paul Graham's advice. I remember specifically going into office hours with PG and having 12 really well-thought-out strategies to present to him of how we were going to spend our Y Combinator weeks together. And he basically looked at all 12 of them and said, 'These are crap.' And we looked at each other and we're like, 'Oh crap, what are we going to do?' And he said, 'Go to where your market is, like go to New York.'
So I remember that weekend we booked tickets to New York City. Brian and I, we had this camera equipment, we're trudging around the snow in Manhattan and Brooklyn going door to door to our users' homes, and sometimes you'd end up spending like hours with them. They'd have just so much information and so many good insights on what we were doing wrong with the website. And so we were just soaking it up like a sponge.
We come back to San Francisco literally just in time for the Y Combinator dinners. I remember we'd be the first ones there at Mountain View. We'd run in with our luggage, we'd get dinner, and then head back to San Francisco. And we'd take all that knowledge that we got from New York and we'd start to apply it here in the office. We'd make changes very quickly to the website. We were a three-person team at that point, so we could.
I remember emailing some of our users that we met in New York, and they were so thankful. They couldn't believe that the co-founders of the company flew across the country to meet them, to take photos, to listen to their problems, and then they fixed the problems within like a week. So right away we were starting to get a really passionate, very loyal user base in New York City, and we learned from that. We continued to grow it out.
J
Joe Gebbia31:21
That's another thing — a lot of people, when they have a website, if you ask them — very few people anywhere in the country have met a founder of a website that they use maybe on a daily basis. And so I think we take it for granted living here in Silicon Valley — everyone seems like they run into people that start websites. But even in New York City, and especially if you're just talking about other cities outside of New York and San Francisco, very few people have ever met somebody that started a website that they used on a daily basis. And so that's actually really, really meaningful. You can't take little things like that for granted. And also, your users will do work for you.