Nathan Blecharczyk: The Raw Truth of Scaling Airbnb to a $75B Empire | E122

Summary

Leap Academy with Ilana Golan

Episode 122: Nathan Blecharczyk – The Raw Truth of Scaling Airbnb to a $75B Empire

Date: August 26, 2025
Host: Ilana Golan
Guest: Nathan Blecharczyk, Co-founder Airbnb

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Episode Overview

In this candid and inspiring conversation, Ilana Golan sits down with Nathan Blecharczyk, co-founder of Airbnb, to explore the unfiltered journey of building one of the world’s most iconic companies. Nathan shares his early adventures in entrepreneurship, the raw realities and setbacks of Airbnb’s first years, game-changing inflection points, strategic decisions during crises like Covid-19, and lessons learned on scaling a global brand. Packed with practical insights for entrepreneurs and leaders, Nathan opens up about risk, resilience, failure, partnership, and the art of “creating your own luck.”

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Key Discussion Points & Insights

1. Nathan’s Early Entrepreneurial Roots

[01:29–05:44]

• At 12, Nathan taught himself programming from his father’s engineering books.
• Started selling his software online, landing his first $1,000 contract at age 14.

  “My dad said, ‘Son, nobody from the Internet’s gonna pay you $1,000.’...But sure enough, 30 days later, I got paid.” — Nathan [03:09]

• Built a high-school business, almost earning a million dollars in sales licenses, which “gave [him] the confidence to learn anything and deliver value at a young age.”

2. Early Career Decisions & Lessons

[06:04–10:12]

• Paused business to focus on the college experience at Harvard.
• His first corporate job was unfulfilling, illustrating the importance of pursuing roles that challenge and develop you:

  “If you’re no longer learning and growing, it’s time to move on.” — Nathan [08:31]

3. Move to Silicon Valley & “Everything Not To Do” in a Startup

[10:12–13:34]

• Nathan moved west for a more entrepreneurial environment, joining a failing startup:

  “I learned everything not to do when starting a company…like being overly confident in your outcome.” — Nathan [10:39]

• Gained experience in leadership, product distillation, and hiring—skills later invaluable for Airbnb.

4. The Craigslist Connection & Airbnb's Genesis

[13:34–17:51]

• Nathan became roommates with Joe Gebbia via Craigslist; their synergy of skills (design and engineering) spurred their partnership.
• The iconic “air bed and breakfast” idea was born from rent struggles and a design conference in San Francisco.

  “Instead of calling it a bed and breakfast, he calls it an air bed and breakfast.” — Nathan [14:22]

5. Not Obvious from the Start: Ideation & Initial Skepticism

[17:51–21:52]

• Nathan highlights how Airbnb wasn’t an immediate, obvious path; the team brainstormed for months before recognizing their unique story.
• Early investor and public skepticism:

  “Honestly, when investors heard the idea, they would have almost a visceral reaction…like, a scary idea that was almost revolting.” — Nathan [22:11]

6. Facing Rejection and Embracing Scrappiness

[22:11–25:56]

• Airbnb endured a year of rejections, with no funding and struggling revenue.
• Emblematic “Obama O’s” and “Cap’n McCain’s” cereal boxes were conceived as a PR stunt that unexpectedly generated $30,000 (more than Airbnb made in a year up to that point).

  “If only there was a presidential election every week, we could just be making cereals!” — Nathan [26:53]

• Yet, as Nathan admits, this was “exciting, but clearly not a repeatable strategy.”

7. When to Quit, or Double Down — The Y Combinator Story

[31:21–36:10]

• The founders made a pact: if Y Combinator didn’t materially improve the business in 12 weeks, they’d all walk away together, amicably.
• Y Combinator almost passed, but the Obama O’s cereal impressed Paul Graham, who admitted them:

  “You’re not being picked for your idea. The ideas can change. It’s about your tenacity, your perseverance.” — Nathan [35:38]

8. Transformational Mentorship & Product-Market Fit

[36:44–40:40]

• Paul Graham’s pivotal advice: “It’s better to have 100 users that love you than a million that kind of like you.”
• The team traveled to New York City, personally helped hosts photograph listings, built rapport, and sparked word-of-mouth growth.

  “We rode the media wave…you can’t make the wave, but you can ride the wave. So you just gotta identify the wave and make yourself relevant.” — Nathan [25:56]

9. Unlocking Growth: From Near-Failure to Rocket Ship

[40:47–44:17]

• After relentless iteration, their revenue increased from $200/week to $4,200/week during Y Combinator.
• Secured $600,000 from Sequoia Capital at a $3 million valuation (“paltry by today’s standards, but we were stoked!”).

10. International Expansion and Facing Competition

[44:17–51:13]

• Strategic decision-making when Europe-based Rocket Internet launched a clone.
• Relied on mentors and Sequoia’s advice to bet on localizing Airbnb across Europe, resisting easy acquisition offers.

  “We viewed ourselves as missionaries... our competitors were out to make a quick buck. That didn’t appeal to us.” — Nathan [46:12–46:51]

• Fast-tracked international hiring, opened eight to twelve new country offices.

11. Cracking the Code on Global Adoption

[51:13–52:08]

• Success in China and skepticism in every market (“People everywhere said, ‘that might work where you’re from, but not here.’ But it always worked!”).
• Over two billion guests worldwide have now stayed with Airbnb hosts.

12. Crisis Mode: Navigating Covid-19

[53:07–59:19]

• Covid-19 dropped Airbnb’s business by 80% in eight weeks as IPO plans evaporated.
• The company executed fast layoffs (1,800+ employees), raised bridge capital on tough terms, and pivoted to focus on domestic, local travel.

  “There’s a quote from Andy Grove…‘Bad companies are destroyed by crisis, good companies survive, and great companies come out stronger.’” — Nathan [57:12]

• Within months, Airbnb stabilized, grew again, and pulled off a successful IPO by year-end 2020.

13. The Future: Experiences, Services, and Community

[59:57–63:42]

• Pandemic forced focus on core business, but now Airbnb is doubling down on Experiences (authentic localized activities) and Services (amenities and personal touches traditionally found in hotels).

  “We always think, ‘what can Airbnb uniquely do?’ And how can we leverage our host community…to empower people to provide travel services in new ways?” — Nathan [61:27]

• Belief that the future of travel is powered by community, connection, inspiration, and unique, trust-based experiences.

14. Reflections and Lessons for Aspiring Entrepreneurs

[63:42–67:36]

• Don’t get paralyzed by opportunity cost:

  “As long as it’s challenging and you’re learning, it’s just one step in your journey…there are many right paths.” — Nathan [64:09]

• On luck and opportunity:

  “I think you can train yourself to notice opportunity that is right before you. We’re all surrounded by opportunities; we just fail to notice it.” — Nathan [66:08]

• On creating your own luck and being resilient, adaptable, and observant.

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Notable Quotes & Memorable Moments

• On Focused Growth:

  “It’s better to have 100 users that love you than a million that kind of like you…you need evangelists.”
  — Nathan [00:35, repeated at 37:05]

• On Handling Advice:

  “Advice is a stimulus…every time we engaged someone, we came away with new thoughts.”
  — Nathan [37:30]

• On Crisis Leadership:

  “A crisis is a terrible thing to waste.”
  — Nathan [58:02]

• On Opportunity Cost & Career Decisions:

  “There are many right paths…as long as you’re learning, you’re building your skill set for that ultimate thing.”
  — Nathan [64:09]

• On Global Adoption:

  “Everywhere we went, people said…‘this will never work in my country,’ and it was so amazing to see that not true.”
  — Nathan [51:13]

• On Creating Luck:

  “You can train yourself to notice opportunity that is right before you.”
  — Nathan [66:08]

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Timeline of Important Segments

• Nathan’s first paid software gig: ~[03:09]
• Starting & pausing his first business: [05:44–06:04]
• First engineering job, lessons learned: [06:04–08:31]
• Craigslist roommate: Joe Gebbia, Airbnb’s spark: [13:34–14:22]
• Early investor rejections & “Obama O's” cereal: [22:11–26:53]
• Y Combinator interview & admission story: [31:32–36:10]
• Transformational advice from Paul Graham: [36:44–37:30]
• Hypergrowth after finding product/market fit: [40:47–44:17]
• Turning down European acquisition, rapid expansion: [46:11–50:10]
• Scaling in China & proof of global appeal: [51:13–52:08]
• Covid-19 crisis, layoffs, rebound, IPO: [53:07–59:19]
• Vision for Airbnb’s future & Experiences: [59:57–63:42]
• Closing advice for future entrepreneurs: [63:42–67:36]

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Takeaways for Listeners

• Big ideas often seem crazy at first—don’t ignore the “obvious in retrospect.”
• Building something new requires evangelists (not just users), relentless experimentation, and personal connection with your first customers.
• Resilience and scrappiness, especially in the face of repeated rejection or crisis, are what separate winners from quitters.
• Strategic partnership, seeking diverse perspectives, and learning from mentors are critical for scaling.
• Even once-successful products or models may need to be rapidly reinvented in crisis, with extreme focus on core value.
• Create your own luck—be attuned to opportunities, be willing to take risks, learn from every endeavor, and move when you stop learning.

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This episode is a masterclass in entrepreneurial grit, leadership through uncertainty, and the power of community in building iconic, world-changing companies.

Transcript

[A]

Wow. This show is going to be incredible. So buckle up and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast track to leadership land, dream roles, jump to entrepreneurship, or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success. So subscribe and download so you never miss it. Plus, it really, really helps me continue to bring amazing guests. Okay, so let's dive in.

[B]

It's better to have a hundred users that love you than a million users that kind of like you, right? Like you need to have evangelists, people who feel really passionate about what you do.

[A]

Nathan Bletervicek is the co founder of Airbnb, which is a platform that redefined how we travel, how we connect, the way we create experiences, how we experience the world. With millions of hosts and guests across 200 countries valued at around $75 billion.

[B]

Today, a whole year has gone by. Our actual business isn't making any money. It's not growing. Despite all the work we're doing, we are having trouble paying our rent again. You know, when do you quit?

[A]

When do you quit? Why continue?

[B]

So we made an agreement, and this in itself is a pretty interesting story and a lesson.

[A]

So take us back in time. You've been like, tinkering with code, building things from a very young age. How did that shape you take us back in time? A little bit.

[B]

Yeah. I got started at a very young age. Like, you know, many young people, I was into playing computer games and such. And one day at the age of 12, I was homesick from school and my dad is an electrical engineer and he had books about computers. This is like the mid-90s right now. So, you know, computers are still kind of newish. Internet's definitely new. Anyways, I start looking through his books and start learning how to write simple scripts based on these books. And I was interested in that because it was relevant for playing my games. Out of that, though, that Christmas, I asked for a programming book and I got one that was basically how to program in 21 days. And it's a 500 page book. I actually managed to complete it in about 30 days while also going to school and doing other things. So I devoured the book and from there on I just kept going to the bookstore at that time, Barnes and Noble, and buying more computer books. Oftentimes you know, 500 page books, reference books that were probably not meant to be read from front to back, probably not by a kid. But I was just super curious and hungry. So I was teaching myself how to code. It became a hobby of mine. I was posting my work on the Internet. I said, if you like my work, please send me $5. Nobody ever sent me $5. But better yet, at the age of 14, I got a phone call. So a couple years later, I got a phone call. It was a guy who said, I saw your work on the Internet, and I would like to pay you $1,000 to make something similar for me. So I'm excited. I tell my dad, hey, somebody from the Internet wants to pay me a thousand dollars. And he's like, son, nobody from the Internet's gonna pay you $1,000. I mean, this is the mid-90s, so this is all very novel.

[A]

It's weird. It sounds like a fraud.

[B]

It sounds like a scam, right? Totally. It still sounds like a scam. It sounded like one back then too, but I said, like, whatever, dad. Like, this is my hobby. I'll do it just for fun, and we'll see what happens. So I did the work, and sure enough, 30 days later, I got paid, which is pretty cool. But better yet, I got introductions to other people who needed similar things made. And so this began kind of like a consulting business where I was writing code for contract, and then I kind of had an aha moment where I said, you know, I. It feels like people are asking me to write the same thing for them. Like, instead of creating a bespoke product for each person and reinventing the wheel, like, why don't I just create a software product and sell licenses to it? And so this began a business that I ran throughout high school for about four or five years before that.

[A]

Nathan, were you exposed to entrepreneurship? Like, as far as I'm concerned, I was in intel at the time, and entrepreneurship, even the word didn't exist. Like, how did you. Were you exposed to that? Were you inspired by anything?

[B]

Yeah, I think ultimately my parents, and my dad in particular, like, kind of instilled the key ingredients. You know, it wasn't by the name of entrepreneurship, but, you know, he taught me definitely a few things. I mentioned he was electrical engineers. Electrical engineer. But he one taught me to be curious. Like, he was always bringing home stuff from work for me to take apart and tinker with. And, you know, he's very much about, like, you can teach yourself anything. You can just go to the library, get A book. He never hired anyone in his life, I think, to do anything for him. He's a very, you know, handyman.

[A]

That's amazing.

[B]

And, yeah, I think just kind of, you know, a work ethic as well, you know, work hard. So, yeah, I think, I think this kind of, you know, led. Led me towards the entrepreneurship journey.

[A]

So then you have a consulting at age as a teen. So where. Where did that go, Nathan?

[B]

Right. So I started off as consulting, became a software business, selling licenses to products. Made almost a million dollars based in high school. And it was just me, really. I didn't have any employees. I had a few software products I was selling. More important, though, than the money was kind of the lessons that. That imparted. One, I taught myself all the skills, so that gave me confidence that I could just, you know, learn whatever I needed to know on my own. And then second was simply that I could do things that other people valued, you know, and I'm like a teenager. So, like, you know, you don't necessarily think of yourself as an adult or capable of that. And yet I was doing it, and I was getting a lot of positive feedback. And so that was just fuel for the fire. And out of that, I think, came my. My love for entrepreneurship. The satisfaction of building something for someone gave me a taste of entrepreneurship. And that's when I bec, you know, effectively a lifelong entrepreneur.

[A]

Which is interesting because also as a teen, when you make so much money, you could also decide that maybe you want to get lazy. But it sounds like that was not in your books. But. But tell me, so what happened next? So you, you have this, like, business. How did you get into Airbnb and how did that start?

[B]

A few things happened there. So, like, I started this in high school, then I went to college. I went to Harvard. The first year was actually pretty easy, but my second year got pretty hard. And in the second year, I made a decision to shut down my business. Actually, I know some people drop out of school and pursue the business. Many of my peers have done that. But for me, I thought, you know what? Like, this is an experience I want to have. It's a period of my life. I'm going to do this. And, you know, there'll always be other entrepreneurial opportunities in the future. And so I actually shut down my business, focused on having the college experience for those four years. And then it was a question of like, well, what. What do I do after. After college? And I ended up getting kind of what I'll call a normal software engineering job. At like a mid sized company. That might sound surprising given my entrepreneurial activity. You know, they had come recruiting on campus and the kind of work they were doing fit some of my academic interests. So I thought it was cool and interesting and so I went with it. And I thought, you know, this will give me like just another perspective that will presumably be valuable. I don't have to do it forever. Well, I ended up being very short lived. I only stayed there for about seven months. By the time I showed up, which was like five months after I interviewed, a few months after graduating. By the time I showed up, they needed me to do something completely different than what they had sold me on. So that was a little disappointing. And it turned out that the pace of what they were doing was very slow. And I just found myself, you know, being bored and not really engaged with it. It wasn't stimulating for me. And you know, I went to quit and my boss said, oh, you can't quit, you're our most productive engineer. And that was really funny slash alarming to me because actually what was happening was I had an office all to myself and I only had one meeting a week. So for the most part nobody knew what I was doing in the office. You know, my routine was I'd come in and I'd code the first half of the day. The second half of the day I'd be like trading stocks, reading blogs, you know, not working effectively. And then to be told that you're the most productive engineer, that's scary for a high achiever. I think it reinforced the point that I was not being challenged, I was not growing, I wasn't gaining skills that I thought was going to further my career or my entrepreneurial ambitions. And so I quickly made the choice to leave. And I think that's a really important, just general lesson. I don't think there's any wrong career choice as long as you learn in the process and you're being stimulated and that you make the decision when it stops becoming challenging, it stops becoming interesting. That's when you move on. And so that's what I did next.

[A]

But that's also very brave, Nathan. Right? Because I mean, I don't know, I mean you're, you're young but you're, you still have a salary. Was it scary?

[B]

I had just a lot of confidence in my, my ability. So I always knew that I could always get a job, you know, if and when I needed one. And I could also do consulting. I had also saved a bunch of my money from my high school Business. I did not go and spend much of it at all. I had some cushion there to allow me to take risk. And then I also just had confidence too.

[A]

So you quit? Yeah. What happened?

[B]

I quit. And at this point, I had grown up in Boston. I went to this job that was in the greater Washington, D.C. area. So I'd been on the east coast exclusively. And I made the decision that it was, it was time to go west. It was time to go find other people like myself. Because especially back then, I found not a lot of people like me, not a lot of entrepreneurial tech people in Boston or even D.C. at that time. It's different now, but back then I really felt alone. You know, all my friends from Harvard were going off to medical school, law school, business school, getting high paying jobs. You know, they'd ask, hey, Nate, what are you doing? And I'd say, I'm working on my projects. And they'd be like, you know, you just kind of get it, kind of like be a dead conversation, you know, they didn't understand that. And so you felt a little out of place.

[A]

And Silicon Valley definitely had that. Yeah, definitely had this.

[B]

But it's the opposite. You know, there everybody's an entrepreneur, which means they're quitting their jobs and pursuing their passion. And that's like, you know, that's the cool thing to do. It's not to go down a more traditional path.

[A]

Yeah.

[B]

And so I went to the west coast to try to, you know, find people like myself.

[A]

What year was that?

[B]

This is 2007. Okay, 2007. And so through a friend of a friend, I got connected to a startup opportunity. This is not Airbnb. This is something else I like to say. From this opportunity, I learned everything not to do when starting a company, which is actually super valuable experience. I mean, it was definitely stressful, but it was super, super valuable. You know what happened?

[A]

Give me an example. What were like a lesson that you decided to take with you.

[B]

Well, I think the most obvious thing is being overly confident in your, in your business outcome. Right. This, this was a company that they just were so confident that they were going to make $7 million in their first year that they could therefore afford to spend any sum of money in order to just move faster. And of course, you know, I, I know of very few, if any, people who in the span of 12 months made $7 million when starting a company from scratch.

[A]

Right.

[B]

That doesn't, that's not how it works. It takes longer. And so, you know, they just ultimately ran out of Runway. But when I joined, I was joining as an engineer. As soon as I joined, the two lead engineers quit. That probably should have been a warning sign. They had already seen enough. But it ended up being a really great opportunity for me nonetheless, because I got to step in and work with the founders to take their big vision, distill it down into a product specification, hire an engineering team, and go build it all in the span of 11 months. So it was a highly concentrated learning experience that didn't end the way that I had hoped, but also didn't necessarily negatively impact me, minus, you know, the sense that I had put a lot of effort in.

[A]

But it's also the first kind of management role that you had, right? I mean, it's kind of like it. When were you.

[B]

There was a lot of responsibility. There was a lot of responsibility, and it included hiring people, for sure. And I learned a lot of skills that were then relevant to Airbnb, which is what comes next at this point. So when I moved to San Francisco in 2007, I of course need a place to live. So I go on Craigslist and I find a roommate, and through Craigslist, I find Joe Gebbia, you know, who later became one of the co founders. But he was had a apartment in south of Market, San Francisco, that looked nice. So I applied and showed up and I actually got a call the next day and he said, oh, you know, sorry, but we gave it to somebody else. There was another designer that we really liked, and so we're sorry, we can't offer you the room. So I was bummed. But actually then a few days go by and the person they had chosen, that Joe had chosen fell through and backed out. And so Joe called me back and said, hey, would you like the room? I said, oh, yes, I'm still interested. So he and I became roommates, living in San Francisco together for quite a few months. And during this time, we made some important observations about each other. One, after working on the weekends, we would come home and work on our passion projects. We had a lot of things we were into, and we would just work hard on them late into the night. And so we saw in each other a passion and a shared work ethic. And then second, we realized we had complimentary skill sets. Joe is a designer by background, I'm an engineer by background, software engineer. So we started helping each other with our projects because we had complimentary skill sets. I was building websites for him, he was building UIs and marketing material for me. We saw the power of Putting different skill sets together and what we could build when you do that.

[A]

Right.

[B]

So, you know, those were two observations that really led to the creation of the company because.

[A]

And maybe I'll jump in when you say observations that work ethics is, you know, basically like working your asses off, like you guys worked all day, all night. Am I understanding correctly?

[B]

Yeah, exactly, exactly.

[A]

Okay.

[B]

But I think, you know, choosing your co founders or business partners is such a high risk thing. It's a professional marriage. And so many companies fall apart because the founding team breaks up. We had the opportunity to be friends, be roommates, observe each other's habits before getting serious about doing a business venture together. And so, yeah, I think it gave us a lot of confidence that we'd make a good team.

[A]

When are we starting?

[B]

The aha moment, right. Is leading up to October 2007, the rent on our apartment is raised 25%. And they say, that's too expensive. I'm moving out. And another one of the roommates moved out. But Joe wanted to stay in the apartment. But he had quit his job to become an entrepreneur, also known as unemployed. So he didn't have the money to pay the increased rent either, but he wanted to stay. He calls up Brian, our other co founder and CEO. And Brian and Joe had gone to Rhode Island School of Design together. So they were good friends from back then. Brian had been living in Los Angeles, working a more traditional job, and Joe gives him a pep talk about quitting his job to become an entrepreneur and joining him in San Francisco for an adventure of entrepreneurship. So Brian gets inspired, quits his job, moves to San Francisco. I think without asking the cost of the rent, that whole part was, was, I think not spoken about until he showed up. And now there's two of them and they're realizing they still don't have the money to pay the rent. And so they're both designers by background. And they noticed that an international design conference was coming to San Francisco, and they noticed that all the hotels were sold out. And so they had this idea, why not take the extra bedroom, the bedroom that I had vacated, and rent it to designers who might need a place to stay that one weekend as a way to make some extra money. Now this room is completely empty. It doesn't even have a bed. But Joe sets up an air bed, and instead of calling it a bed and breakfast, he calls it an air bed and breakfast. So airbnb is short for air bed and breakfast. They create a simple blog advertising the room and the air bed, and they're expecting guys like themselves, so 25 year old male probably, and instead they get a father of four from Utah, a man from India and a 35 year old women from, from Boston. So like eclectic group. These guests get an affordable place to stay when hotels are otherwise sold out. And Joe and Brian make I think like $80 a night, you know, times I think three or maybe four nights times three people. So almost a thousand bucks. And they all go to the conference together, have a really great time, and Joe and Brian introduce them to their friends and they get meals. So it's, you know, it's really actually a whole experience that created immense connection and it was really just meant to be a one weekend way to raise a couple extra bucks. But you know, one of the guests a month later checked in and said like, hey, you know, that was so much fun, like what are you doing next with air bed and breakfast? And they're like, well nothing. Like there was just a one time thing. And he's like no, no, no, no. That was too cool to walk away from. You should do something more there. In parallel to this, the three of us had been brainstorming. At this point, I had now quit my job. So now three of us are unemployed, all wanting to be entrepreneurs, all wanting to work together. And for two months we were brainstorming ideas of what we could do together. And we had some ideas around like a roommate matching service or something like that that seemed relevant to what we had just recently gone through trying to find roommates. We went for two months brainstorming ideas without ever talking about the story that I just shared with you. That's like how it's like so obvious in retrospect that like one thing led to another, but in the moment, you know, it was sitting underneath our noses. And for two months, you know, we didn't even realize it. It wasn't until we got that call from the guests encouraging Joe and Brian to kind of take the idea forward that they then shared it with me. And the three of us got enthused to go make it possible to book a home just as easy as a hotel all around the world. And that's what we set off to do in early 2008.

[A]

And that's incredible, Nathan. So first of all, I love that you shared the story story that it wasn't as obvious, right? Because I think sometimes we especially the high achievers are driven. We want to tick all the boxes, we want all the evidence up front. The evidence is not there because you, you didn't get there Yet. Right. So I. I love that you share that. But from that moment, like, you get this idea, but initially everybody thinks it's crazy. And I was in Silicon Valley at that time. Like, everybody was just like, there's no way on earth that somebody will stay with a stranger in the house or let a stranger in the house. Like, it's just absolutely not possible. So what made you continue to try? Right, like, because you guys go to investors. Tell us a little bit about that beginning.

[B]

Yeah, well, a few things, I think. One, we knew the three of us wanted to work together on something, right? And then this happened to be the idea, and the story was, you know, pretty, pretty awesome. And so it seemed like a cool enough thing to work on. Now, I, at the time, did not think this was going to be a big idea. I actually famously, like, wrote a, like, end of year note, which I would do every year to all my friends, and I described all the things I was working on. And this was like, in the footnote as, like, as something that was, like, kind of fun, but probably not a big deal, you know, Much to the chagrin of Joan, Brian, who also got the letter, did not appreciate that characterization of our serious effort. I have to be honest, I was also a little cautious about jumping in at this point because I felt like I had a lot of opportunities as an engineer. I had, like, skills that were very much in demand. So there's, like, a high opportunity cost with what else could I be doing? And it's very easy to be tempted. Like, you know, should I go work for this company, get paid a lot of money, or I have, like, three other ideas I'm working on. Like, where do you focus and what do you double down on? I was partnering with two designers, and on the one hand, they had complementary skills, so that was compelling. You know, on the other hand, I felt a little outnumbered. Right. I felt like I was the only engineer, and these guys could probably dream up things faster than I could go build them. You know, I was hesitant, but, you know, ultimately, a couple things I think, you know, one, you know, we were able to come up with a kind of scoped down version of the vision that was manageable. So in the span of, you know, I think five weeks, we built our first iteration of the product. And it's different, a little bit different than what you see today. But, you know, very quickly we were able to get something and put it out there, you know. Second, it did kind of come down to having somebody to work with because, you know, I had some Other ideas. I was also working on just myself. And I remember building something that I was frankly, more excited about. And I was so excited to, like, launch it. And when I launched it, I realized that this was just the beginning of building a business. Like, I built a technical thing, but that's not a business. That's just, like, a product or a proof of concept. And there's so much more that needs to happen in order to turn into a business. I need, like, employees or business partners. And so suddenly I felt kind of very lonely, and I valued that. With airbed and breakfast, I had Joe and Brian, you know, people who are equally excited and passionate and, you know, willing to work. That was part of what propelled us, you know, in that first year. You know, even aside from the fact that the idea was crazy, this is what kind of set it apart from, you know, other things that were also on my mind that I was also excited about. Now, you know, you point out, like, how did we have confidence in this idea when it was, in fact, so counterintuitive at the time? You know, how can you trust a stranger? In other words? And, you know, it was based on the firsthand experiences that we were having. I mean, of course, that story I just shared from October 2007 is very compelling. But we had other experiences, you know, shortly thereafter as we launched the product. We didn't have many people use it, but when they did use it, you know, magic did happen quite a lot. And those stories were really powerful. And so it can work. The question is just how to help more people take the leap, you know, and embrace meeting somebody new and having this kind of value exchange. That makes a lot of sense. That's what we understood that, you know, nobody on the outside really did.

[A]

Right. And again, you had a level of conviction that allowed you to basically go to investors, hear a lot of no's, and continue. What, like designing cereal boxes? Like, tell me a little bit. Like, I mean, you had enough stamina to continue.

[B]

Honestly, when investors heard heard the idea, they would have, like, almost a visceral reaction. Like, it wasn't just that, like, it was a bad idea. It was like a scary idea that was almost revolting. Like, they honestly didn't see themselves as customers. Right? They're investors. They probably have a fair amount of money. They were not looking to, you know, necessarily save money on a hotel and stay in someone's extra bedroom, at least not at that time. So, yeah, they would have a pretty strong reaction. Over that first year, no one was willing to invest. No one would even give us a second meeting, and then give me a.

[A]

Second, take me there for you. Because, again, you have other options. I mean, this is. You know, anybody that is at your caliber can go anywhere at this phase. Why did you decide to continue and how did you guys together take those rejections? Because that's not easy.

[B]

Yeah, and there was other stuff going on that was not easy. You know, for one, actually, during this time, I had moved from San Francisco back to Boston. So suddenly I was working remotely with my. My co founders, and that was to be with my. My then girlfriend, who I'd been dating, you know, for a long time, who is now my wife. We've been together for, you know, a couple decades now. But, you know, it was time to get serious and. And spend some time together. And so I went back to Boston to be with her. But that obviously strained my ability to work with Joe and Brian and also led to some funny dynamics about just how to handle rejection. Because as the engineer who had a lot of other opportunities, I was very busy with the coding, and I was not going to all the investor pitches. They were doing that out on the west coast while I was on the east coast working. So I would be eager to hear how the meetings went. And they would always kind of frame it in more positive terms than it was probably the actual reality. They were like, oh, they thought it was interesting and curious and they'll get back to us and they need a little more time. They didn't tell me the part that they were like, the investment.

[A]

Kicking you out.

[B]

Kicking us out. Yeah. And so I also remember one time I was in San Francisco during one of these meetings, and we were practicing the night before the pitch deck, and we come to this slide that is basically, how much revenue will we be generating three years from now? And the number was 200 million. And I did some quick sanding checks, and I said, there's no way we can ramp to 200 million from zero. It just makes no sense. 20 million is more realistic. Why don't we put 20 million on the slide? And so Brian's like, yeah, okay, sure. And then the next day, we're in the investor meeting, and we covered this slide, and the slides was not 200 million, not 20 million, but it says 2 billion. So instead of decreasing it, he increased. Was at that moment in time where the investor totally just, like, looked out the window and stopped paying attention. And so, you know, afterwards I asked Ryan, like, why? Why did you change it? And we had talked about 20 million, and now you changed it to 2 billion. Why'd you do that? He said, oh, well, you know, I was. Was talking with Sam Altman, you know, OpenAI Sam Altman. So we knew him way back then. He had been a Y combinator and kind of in our network. And so we got some advice from Sam Altman that investors don't want M's. They want bees, baby. Meaning investors don't want to invest in million dollar opportunities. They want to invest in billion dollar opportunities. And so it's a prerequisite that you have to sell a big idea, which is actually, of course, true. The problem is in our pitch, we didn't really connect the dots between what we were doing and it being a billion dollar idea. So I think, you know, both perspectives were, has some validity to it. But bottom line is the pitch did not go well. And I got to see that firsthand and was definitely very alarmed by that.

[A]

Out. So tell me the story about designing cereal boxes with Obamas and Captain McCain's. Is that true?

[B]

Yeah, no, it's very true. And so, like, what led up to that was it's now summer 2008, and we're going to launch the company officially at the Democratic National Convention. This is the event that took place in Denver where Barack Obama received the nomination of his party to be the presidential candidate. A historic event. First African American presidential candidate. The stadium where it's going to be held holds 80,000 people. And we know Denver only has 17,000 people, so we know there's going to be a need for alternative accommodations. And so that's why we made a whole goal of being ready to launch two weeks before then. And, you know, sure enough, it was a big success. Like, locals were looking to get out of town. They were putting their stuff up on Craigslist and ultimately then on Airbnb. And we ended up hosting hundreds of people for this event. And also the newspapers and blogs and TV were doing stories about the event, of course. And of course, one of the storylines was historic event, but people have no place to stay. They're like camping out in parks. So, you know, we wrote to the reporters and said, hey, actually, we have 800 confirmed available homes on our platform still available. And they would say, oh, that's an interesting story. I'm going to feature you. Because we rode the media wave, right? We didn't create the story. The story was out there already about the event. And we made ourselves, we made our product relevant to that event. And so that was a great. That's a great strategy in general for Getting media attention, right? Like, you can't make the wave, but you can ride the wave. So you just got to identify the wave and make yourself relevant to it. So that's what we did very successfully. And we were on CNN and just getting amazing coverage, and we sold hundreds of bookings. Now a week later, the convention's over and nobody cares about us anymore, right? There's zero business. And so this got us thinking. We had met all these reporters during the previous week, and now they didn't care about us anymore. But how could we get back in touch with them and make ourselves relevant to them and get featured again? Because that was so amazing. So I don't know how it happened, but basically, Joe and Brian got this idea to create a presidentially themed breakfast cereal. And it was partially because the name of our company was Airbed and Breakfast. And so obviously the product is Airbeds. But they thought it'd be funny to do something with the breakfast concept that was also part of the name at the time. We weren't Airbnb yet. We were still Airbed and Breakfast. And they said we should create a presidentially themed breakfast cereal, and then we should mail these physical boxes to all the reporters. And if they get a box of our presidential cereal, they'll be so curious. They'll call us back and we'll start talking to them again. They come and tell me the story, and I just think it's ridiculous. And I said, guys, do whatever you want, but just promise me that you won't spend any money. I was like, heads down writing code, and I had a backlog of things I needed to do. And I said, you guys can spend your time doing that, but just don't spend any money. To their credit, they were super scrappy. They didn't spend any money. They got friends and people in their network to help print off the boxes. And being artists themselves, they were able to create amazing artwork for these boxes and super witty concepts and hot glued all these boxes together and stuffed them with cereal. So they're super scrappy. And they made it, you know, in the span of like a month and a half, they made presidentially themed breakfast cereal. Obama owes tagline was Hope in every bowl and Captain McCain's the Maverick in every bite. And so the first 100 of each of these boxes, they mailed in the physical mail to the reporters. And then the extra boxes that they had had printed, they decided to label as a limited edition collector's item. So they numbered each one 1, 2, 3, 4, all the way up to 400. And we made a little website to sell them on. So anyways, the reporters get these boxes, and sure enough, this is in the lead up to the election. So there's obviously a whole hysteria about the election and excitement and people doing wacky things. And so we're an example of a wacky thing that's going on. So sure enough, we get back on CNN and Good Morning America talking about the breakfast cereal, talking about airbed and breakfast, what this is all about. And that day, we become the number one political video of the day on CNN. And we sell a $40 box of our cereal, the limited edition collector's item on our website. $40 a box. We sold a box of cereal every three minutes until we sold out. So that week we made, like, over $30,000. We sold out of Obama O's. We never sold out of Captain McCain. So I guess we could have predicted the election. It was so exciting. And, like, we made more money that week than we had all year in our core business. And we thought, well, if only there was a presidential election every, every week, you know, we could just be making cereals. But clearly that wasn't a repeatable strategy. And, you know, once that passed, we were kind of, once again, kind of back at square one with, like, making no money. A whole year has gone by, and we're asking ourselves, when do you quit? You know, 12 months in May. No money. Except this, you know, kind of hoax. Not hoax, but, you know, like, fad thing, you know, PR stunt. But our actual business isn't making any money. It's not growing, despite all the work we're doing. And, you know, we are having trouble paying our rent again, you know, when do you quit? When do you quit?

[A]

And so when do you quit, Nathan? Because again, this is when, you know, you actually went to Y Combinator and things started changing. When do you quit? Why? Why continue?

[B]

Yeah, well, I mentioned, you know, earlier, like, you know, starting a business with other people is kind of like a professional marriage. And, like, they often fall apart. And so, you know, choosing your founders is really important. And also part of that is making sure you're kind of like, in the same stage of life, too, right? We are obviously young guys. You know, I had a girlfriend, but a serious one, but we didn't have kids yet. And, you know, we were able to take risk. And so, you know, we had made it this far, and that was pretty great. But, you know, we were all getting a little desperate and because we were all friends with one another before doing this, you know, we really didn't want to quit and leave the other, other guys hanging. You know, like, we kind of needed to decide this together. You know, no one person wanted to jump ship. So we made an agreement. We said, you know, we've worked really hard this year. We need to give it one more shot and we need to give it our, our absolute all. The truth is, like, I had been doing some consulting on the side, I had been in Boston. Like they had also some side projects. So we weren't completely focused and we agreed that we were going to apply to Y Combinator, which is a well known accelerator program even back then, and that if we got in, we would do it, of course. And the thing about Y Combinator is it's about a 12 week program and so it's very finite. And we said, we're going to do Y Combinator. If we get in, you know, at the end of the 12 weeks, if the company is in a better, materially better place, we'll all quit together and not have any hard feelings about it. Like, we'll just pre agree up front that that's the condition for quitting. We'll see how it goes. But, you know, before we could do Y Combinator, we had to get into Y Combinator. And this in itself is a pretty interesting story and a lesson known accelerator program even back then. And that if we got very selective. Y Combinator. Oh yeah, even back then. So we did a lot of practicing and rehearsing and like, practice, like stressful interviews, like where, you know, we were shouting questions at each other and like throwing phone books around the room and, you know, just trying to like, make sure that we could stay on point, you know, even in a stressful situation. So we did a lot of preparation and we go to the interview and the interview's only five minutes. It's super fast. Two minutes into the interview, Paul Graham is like, what strangers staying in other people's houses. He's like, I would never do that. You know, like he had the same reaction that everyone else did. He did not like the idea. He was almost like angry about the idea. And at that point the conversation goes sideways and he kind of says, you know what, I really don't like that idea. But you are handling payments between guests and hosts, and so maybe you should become a payments company. So he basically takes the next three minutes to try to convince us to do a different idea, which sounded a lot like what stripe eventually became actually, which is kind of funny. We're five minutes is up and we're walking out of the room realizing we had blown it, right? We completely went off the rails here. And as we're going out, Joe takes out of his bag a box of the Obama Os. And it's funny because before we had left for the interview, I saw Joe putting the Obamas in his bag. And I said, joe, don't bring that to the interview, because for me, the Obama O's and that whole serial story I just told you about, to me, it represented a distraction. Although it was, like, super clever and made 30,000 bucks, it obviously did nothing to drive our core business. And it took about, like, a month and a half of, like, Joe Brian's time. And so I felt like that did not really communicate that we were, like a serious tech company and focused. But Joe brought the Obama O's anyways. And as we're walking out, he takes it out of his bag and gives it to Paul Graham. Paul Graham says, yeah, yeah, But Paul Graham looks at it and he says, what is this? Did you buy. Buy me a gift? What is this? And Joe said, no, we made this. And Paul Graham's looking at it. He's like, I don't understand. You made this? He's like, come back in and tell me how you made this. So we sit down and we get five more minutes with PG and we tell him how we made the cereal. And later that day, we got a call saying that we were accepted into Y Combinator. And later on, Paul Graham told us that we were accepted not because he liked our idea, he hated our idea, but he knows that the ideas can change. And instead, he's really, you know, choosing people based on, you know, the founders and who he thinks will have the tenacity, the perseverance, and the ability to create and build. And so from that story, what he saw was that these are guys who would not give up. They would be very resourceful and scrappy and figure out a way to do things. And so, you know, that met his criteria for admitting us. And I think, you know, it's also just a lesson for anybody when it comes to pitching yourself. You know, the idea is one part of it, but it's also, you know, all about you and your character.

[A]

I absolutely love this story because again, at the end of the day, the ups and downs are insane, especially the downs. So being able to continue, I think that's the big thing that White Combinator is trying to figure out, right? Like, are you going to be the founders that will continue? And. And I think they also gave you some ideas around being closer to your customers. Right. Like eventually in Y Combinator and going more towards New York. Can you share a little bit about, like, some of these big learnings that you had in Y Combinator and how did that shape Airbnb as a whole?

[B]

We heard a lot of advice, you know, during Y Combinator and from other people too, but especially during Y Combinator and from Paul Graham. He always has interesting things to say. And, you know, the thing I'll say about advice is obviously not all advice is good advice. Like, there's all kinds of advice and. But advice is thought provoking. Amongst all this advice we were getting, there were some real nuggets that we latched onto and thought about.

[A]

Actually, let's go there just for a second. Just for a second. Because I think with advice, it's actually really complicated because the grass sometimes always looks greener on the other side. And if somebody really smart tells you go this route, like, you might find yourself. And I see founders do that, right? Like, they just start going all around, how did you continue your North Star and know what to take from which advice?

[B]

I think it's not about, like, necessarily following advice, because some of it's good, some of it's bad. It's about reflecting. At the end of the day, you know, advice causes you to reflect. Is this true? Is it not? Is this a good idea? Is it not? You know, it's a stimulus. It's an outside stimulus. It sparks creativity. And this is important because when you're starting something, you know, so many people are secretive about what they're doing, you know, they don't want someone to steal their idea, you know, and so it leads you to, like, not share. And I think it's a missed opportunity because it's important to hear different perspectives, get different, you know, reactions, and then reflect on that. And it just. I felt that every time we engaged someone about what we're working on, we came away with new thoughts that we wouldn't have otherwise had. And we made a point to go to every single office hours that Y Combinator held. And we were always the first ones there. Spent the most time with Paul Graham just because, you know, we. We wanted to hear his reactions. You know, even though he didn't necessarily like our idea at first, you know, we still wanted to talk with him and understand that and unpack that and get, you know, new ideas. So anyways, you know, one of the things that gets said is that it's better to have 100 users that love you than A million users that kind of like you, right? Like, you need to have evangelists, people who feel really passionate about what you do and then also like to do that. You know, you kind of need to meet your users, right? Like, you need to deeply understand their needs and how they're using your product. And both those things are a little counterintuitive, at least for us at the time, because we thought we were building an Internet company. And, you know, Internet companies are built for scale. And if you're doing scale, of course you can't go meet your users individually. And it's all about bigger numbers. And so these ideas kind of led us to think more about product, market fit, and actually spent time meeting users. And so that's what we did based on that feedback. And Paul Graham said, well, where are your users? Why aren't you meeting them? We said, well, our platform people are based all around the world, and there's not many here in San Francisco. Actually, most of them are in New York. He's like, well, why don't you go to New York? We're like, well, we're here doing Y Combinator. We don't have any money. He's like, I don't care. Go to New York. And so Joe and Brian, back then, when you did Y Combinator, you got twenty thousand dollars. That's wasn't like a hundred thousand or two hundred thousand like they do now. Like they do big numbers now. But back then it was 20,000 bucks. So we used much of the 20,000 bucks going to New York for a few different weekends. And when we went to New York, we realized that a lot of people had photos of their homes, or some had no photos and others had photos, but they were poorly lit. They were poor resolution, especially back then. You know, camera phones weren't very, very good. And how do you meet your users when you're an Internet company? We would call them up and we'd say, hey, you know, we saw that you put your apartment on. On Airbnb. Would you like a professional photographer to come to your house and, like, you know, take some professional photos of it for your listing or whatever other purpose you might like? And I think people were a little surprised to get this, like, offer out of the blue. But a lot of them said yes to that offer. They were curious, and they, fine, yeah, sure, that's a great deal. Free. So, you know, knock, knock on the door, and it was actually Joe and Ryan themselves showing up.

[A]

Did they know that it's the CEO that is coming to take photos not.

[B]

Until they showed up. And, you know, we didn't have any money. They didn't own an expensive camera, but they would actually rent a camera on the weekends just for this purpose. And they'd go and they take the photos. But while they're with the host, they would also sit down at the computer and like, watch them use the product and get ideas from them, give them tutorials, and then also invite them to get a beer later on. And so we get a few hosts together later on for beer. And, you know, over beers, we would tell them our entrepreneurial journey, the stories that I'm sharing now. And you know, people do love those stories. They love a good story. And this was a way in which we started to build rapport with our early community and develop a following of people who loved Airbnb. You know, at this point now in New York, we have good photos on the properties. We've met the host and built a rapport. And with that rapport, we're able to call them up and say, you know what, that price you set, would you mind lowering it? You know, if you get too much interest, you can always increase it. But we think like, starting at $100 a night feels a little too high at this point. You know, you don't have any reviews yet, so could you start it low and raise it up later? And you know, if you had asked someone out of the blue to do that, they would say like, you know, who are you to suggest that? And no, but because they had met us and they liked us, they said, yeah, sure, we'd love to help you out. And so, you know, now we have well photographed properties at attractive prices in New York City, a place that people all around the world want to go to. But it's, you know, really expensive. And these properties start getting bookings, the hosts start making money and they tell their friends and their friends come to the site and they see the effort that the other hosts have put in and they look to emulate that because that's the recipe for success. And so we get more and more hosts in New York. Meanwhile, these guests from around the world who are coming to New York are flying back home and they're thinking to themselves, hey, that's cool, maybe I could be a host in my own home city, in Paris, in Berlin. And so very quickly there's a cross pollination happening. And, you know, this is when things started to take off. And like I mentioned earlier, Y Combinator was about 12 or 13 week program. And we had agreed at the start of it that if things didn't materially improve, we would quit at the end of 13 weeks. So before Y Combinator, we were making $200 a week in revenue and that had been true for five months. Nothing we did seemed to increase it. Our goal during Y Combinator was to get to get to a thousand dollars a week. And literally in the span of 13 weeks, we got to $4,200 a week. So past our goal, quite a lot more than $200 a week. We are also during this time introduced to Sequoia Capital, one of the best investors in the world. And we ended that 13 week period not only with a great ramp in revenue, but Sequoia Capital investing $600,000 in our seed round, leading that round at a paltry $3 million post money valuation. Which is funny and it doesn't even seem real by today's standards. But back then, this was during the recession, the financial recession in 2009. So this is the kind of valuations that were out there. But we were stoked. Now we had our first investor and before every investor had basically laughed at us and not taken a second meeting. And now here's Sequoia Capital, one of the best names in the world, investing in us. So that was a huge boost in confidence and it meant we never had to have that conversation about quitting. And you know, from there forward, it was a rocket ship. So from, you know, March, April 2009 onwards, you know, began that more positive part of the story because that first year was so, so painful.

[A]

And at that point, are you trying basically, I mean, you as, you know, CTO and then chief strategy officer, then you're leading international expansion, Is that kind of when you're starting to move from New York, only starting to expand because you also expanded to really complicated markets like China. And like, is that kind of when this is starting to happen? I mean, after it stabilized, I mean.

[B]

A lot of years, you know, in between 2009.

[A]

Yeah.

[B]

So there's a sequencing to it. Right. So 2009 was really defined by our growth in New York City and then also just starting to build a team. Right. So it was still just the three of us. And you know, I was the only engineer until basically August of 2009. So that's now 18 months after having started. At this point, the company's doing really, really well. It's I think making like $12,000 a week by August. So continue to ramp. We hire our first engineer besides myself. That's August 2009. By 2010, we are now growing in, like, let's say, Paris, Los Angeles, let's say four or five cities are now, you know, thriving. So still small. And then comes 2011. 2011 was another inflection point where just everything happened all at once. So what kicked it off was competition. Up until that point, we had been very quiet about our success. And even when we fundraised money, we didn't announce our fundraisings because we didn't want to tip off other people that this was a good idea. And so we kept it to ourselves and we would share it, but we basically staggered the news by four or five months. By the start of 2011, or let's say late 2010, word of our Series A funding, which had happened in April 2010, had gotten out. So by the end of 2010, that happened. So it was like, five months staggered, and our Series A funding was a $7 million raise at, like, roughly, I think, a $72 million post money valuation. Something like that.

[A]

That is so close. Yeah.

[B]

That got the attention of people, and specifically some serial entrepreneurs based in Europe who are well known for cloning successful Silicon Valley companies, including the Samoa brothers, who have a company called Rocket Internet that famously cloned Groupon and attempted to clone Facebook. And basically every company they try to clone, and they decided to try to clone Airbnb and become the Airbnb of Europe, as does another serial entrepreneur based in Europe. So suddenly we see competition. We know that travel's inherently global. We know that to be a. A relevant travel company, you kind of need to. You need to be in Europe, too. That's, like, a very important part of the travel jigsaw puzzle. So, you know, we become determined to be, you know, just as local as these guys. I guess before we do that, though, like, they. They come to us and say, you know, look, if we work together, if you acquire us, like, we can combine our strengths and our skill sets and, like, you know, definitely be a global company. We entertained it. We had to. I mean, we had a fiduciary duty to at least consider this, this. This offer. And it was. It was totally shocking because at this point, we have 40 employees and remember, flying to Berlin, touring their offices, and they have, like, 200 employees in their office, and they had just started. And, you know, partially that's because they. They had, like, a pool of people, you know, working at other companies that they could pull from and, you know, basically bootstrap this new company overnight. But it's super intimidating to see all those people so many more than we Had. Ultimately though, we realized like, these guys are a little bit kind of like mercenaries is what we call them. Like, and we viewed ourselves as missionaries. Like, we really loved the business. We were, and we were really attached to it. We lived the product and, you know, we felt that our competitors were out to make a quick buck and so that didn't appeal to us. And so we declined the offer. But we realized we needed a plan B. We needed, we needed to get into growth mode and go from like, what I'll call peacetime to wartime. Like, you know, not just like going along the lazy river, but like really start sprinting. We need to be more local than these European companies.

[A]

How do you make those decisions? Like, you're. This is a new type of decisions for you. I guess everything is new for you. But I mean, these are type of like, these are big decisions. Who helps to. Is that Sequoia, Is that someone else? Like, how do you make those decisions?

[B]

They're big decisions. And we definitely, you know, going back to like the idea of getting advice, you know, we would always reach out to different mentors to get their perspective and call other founders and get their perspective. But you know, specifically in this case, yes, you're right. Like our, our partner at Sequoia, the original partner, his name was Greg McAdoo, you know, we would at that time get brunch with him every two weeks and just tell him what was going on with the company. So he was like, you know, spending a lot of time with us just being a thought partner.

[A]

Amazing.

[B]

But, you know, for this, for this trip, he came with us, you know, he saw everything we saw and we had conversations about it and, you know, together we made the decision of like, we're actually going to turn down this offer that, you know, on the one hand felt like it would lead to obvious success because these guys were so experienced operationally and they had so many people and they had Europe to going it alone, which felt very risky. But we made that big decision and quickly through our network, started reaching out to people who had helped other companies to scale internationally and in the span of a couple months, hired country managers for eight to 12 countries and opened offices in those countries and hired local teams. You know, when I say local teams, you know, maybe a dozen people to basically, you know, bootstrap the market and get super hands on and meet the host, like I told you before we did in New York and photograph the properties and all this hands on stuff that is necessary when attracting your first users and building your initial credibility.

[A]

Unbelievable. So you guys are starting to expand all over Europe and again, other countries then at this point, including complicated ones. I don't know if we're going to go into exactly how, but, I mean, some places like China are a whole different gambit of things. Right. Because a lot of things are just not allowed there. I don't know if you want to go over a little bit, but then I do want to go to 2020 at some point.

[B]

So, yeah, I mean, there's a sequencing here. So, like, this competition kind of kicks off in 2011. And I say 2011, 2012 was really defined by this race to win, Europe specifically. And we were also starting to plant the seeds in Asia too, simultaneously. But Europe was the initial focus. But by 2014, 2015, having managed to have success in most of the other markets, if not all the other markets, we also started to explore China, which, you know, was. Was a whole adventure in itself.

[A]

Probably a show of its own. Yeah, yeah.

[B]

You know, a very unique market because of how big the ecosystem is and because of the government and all these different things. But we are incredibly popular in. In China amongst travelers. You know, we used to think like, will this only work in New York? Will this only work in North America? Everywhere we went, people said, okay, that might work where you're coming from, but this will never work in mine, my country, you know, and it was just so amazing to see that not true. And to see. To see it actually work in every country of the world, all around the world, people have a curiosity to meet people from other places, especially other countries, and see how other people live. And so we tapped into that in a way that was also affordable. And so, yeah, I think it's been remarkable to me to see how, you know, we are now ubiquitous for home sharing in every country of the world. It works in every country of the world where we're allowed to operate. And, you know, more than 2 billion people have now stayed in other people's homes. So, like, this idea of strangers is, Is.

[A]

Is no longer long gone. But it's interesting because we got to know you guys roughly around 2007. 2007. My son was born after that, you know, my. My daughter. And at that point, it's like, I'm not going to have two babies in a second room or in a hotel. And, you know, I think at that 2010 or whatever, we started staying in Airbnbs. You know, I mean, it's like it was a must for families. Like, I actually don't know what families do without it. Like If I'm being really honest. So we were very, very early. So I could see which countries are already on Airbnb, which are not, because we were big travelers. And. And, you know, it was. It was really interesting as a family. Like, I literally don't know what families do, which is kind of a whole different story. So take me back in time to 2020. What did that look like again? These. Are you guys in the, like, exactly where the hospitality is. Travel is like, you're right there in Covid hits.

[B]

Right? Well, going into 2020, you know, we're now coming on, like, at that point, 12 years of growth and building the business and had tons of success. And we were planning for our IPO in early 2020. And so, you know, in 2019 already we had written, you know, the draft S1 and done all this preparation. 2020 comes and we're, you know, planning to do this. And then. And then Covid happens, you know, and in early March, who declares, you know, a pandemic, and our business drops 80% in just eight weeks. I mean, it just. It just disappears. That's super scary because, like, at this point, we have, I think 8,000 employees, maybe a little more. We're a big ship, you know, we have a big, expensive burn rate. The costs don't stop, you know, the revenue stop, but the costs are there. And so.

[A]

And probably people are asking for refunds or I don't know, like, how did you cope with that? Like, take me there.

[B]

A lot was happening all at once, right? Like, obviously travel was deeply impacted. That's why no more new bookings were coming in. But also we had existing bookings. Guests were wanting to cancel, and, you know, that might not have been acceptable by the host cancellation policy. So there's billions of dollars of bookings, you know, that had to be sorted out, terms of whether to honor the booking or not and how to navigate that. So that's complicated. There's just a burn rate situation. And the issue there is not just that there's no money coming in, but we don't know how long this is going to go on for. Right. Like, is this a two week thing? A two month thing? A two.

[A]

Nobody knew anything. Yeah.

[B]

Right. So, like, in terms of planning how much, how long your bank account's going to last, you know, we had no idea. We knew we had to raise some money quick. But of course, this is exactly when the market basically froze up and no one was willing to give you money.

[A]

At this point because nobody knew anything. Right. I mean, it's like, right, everybody need.

[B]

Money all of a sudden?

[A]

Yeah, yeah.

[B]

And so it's a terrible time to raise money and we have to make basically a bunch of choices. And I think a couple of things. One is, you know, we realized right away it's a crisis. This was not like something to be managed away or kind of like not by a little time. Like we said, we're going to treat the super serious like from the get go. We're going to be bold. We're not going to take half measures. So, you know, we had to first. Right. Size the ship a little bit into financially. We did a layoff relatively quickly. One of the worst days that, you know, I've had to experience. We lost 1800 employees. But it was necessary to, To. To do that quickly or else everything was in jeopardy.

[A]

Right.

[B]

And we did that with a lot of humanity, too. You know, we found ways to help employees. Like, on the one hand, you know, we needed to help the company. The company was in jeopardy. But we also understood, you know, people also were going through their own situations during this pandemic. And so, you know, we found creative ways to help people find new jobs at other tech companies. We created a whole directory that people could opt into, and we shipped off those names to other companies that were hiring because, you know, some companies were actually doing well during the pandemic. You know, we help people transition and find new jobs. But we also went out and we raised some more money on, you know, terms that were tough, but. But ultimately, you know, necessary and, you know, great.

[A]

Can I take you to a personal question? Like at that point when you go to sleep at night, do you know it's going to be okay, or are you terrified? Like, where is it taking you?

[B]

It's definitely a scary thing for sure, because there's so much uncertainty and there's so much at stake and, you know, everything you thought you had accomplished, you know, is suddenly poof, like gone faster than you thought was possible or, you know, feeling like it could be gone. And so, you know, super scary. You know, at the same time, you know, I think we all got into kind of the wartime mentality, which is like, we're going to buckle down and get super focused, super disciplined. We're going to operate differently, right? We're not going to operate the way we were weeks ago. You know, we're going to meet as an executive team every single day to discuss the status of everything. You know, we're going to get really clear on tracks of work ownership. We're going to make Decisions quickly, we're going to act with boldness. You know, we came up with principles that were going to kind of guide our decision making. We moved incredibly fast to deal with the situation. And then, you know, something we've learned along the way is that a crisis is a terrible thing to waste. There's a quote from Andy Grove, the former intel CEO, that we really liked, which is, like, bad companies are destroyed by crisis, good companies survive them, and great companies effectively thrive or come out stronger from a crisis. And so we had experienced this before in earlier years, where what started off as a crisis was actually a little bit of a call to action that we ultimately not only survived, but came out stronger because of and came out as a better company. And so as we quickly identified that this was a crisis, we were also trying to understand, how can we come out stronger as a result?

[A]

What is the lesson?

[B]

You know, as we were having to cut down on our projects because we had fewer people, you know, we got really clear about, like, what was important in the long term and not to sacrifice those things. And we also thought to ourselves, like, in this pandemic, you know, it turns out people still wanted to travel. They couldn't get on airplanes, they couldn't go to other countries, but they wanted to go out to the countryside, and they wanted to have a home where they could socially isolate, maybe with some other family members and make a little bubble or whatnot. So we realized that the desire was still there. It's now just taking a different form. And so we became very agile in adapting our product to help people find these opportunities and travel in this new way. And so, actually, very quickly, within, let's say, two or four months, we stabilized our business and started growing again by meeting some of these new consumer behaviors through our agility. And actually, by the end of 2020, we completed our IPO. So the IPO that was supposed to happen in, let's say, March instead of pandemic happened instead. We thought the company was about to implode. We stabilized it, returned to growth, and then followed through on the IPO by the end of the year quite successfully. And so it was a remarkable turnaround in the span of, you know, 12 months.

[A]

It's absolutely incredible. Like, I remember even thinking, like, how is it possible that Airbnb, not only that it's not sinking with this crisis? Like, it's actually like ipo? I mean, it was just incredible. And I think a lot of the experiences and the services that you have now, you know, kind of started flourishing. If I'M not mistaken during this time. Right. And again, right now, you're expanding into Experiences and doing all these things in such a bigger way. Was that kind of the accelerator and how is that these offerings starting to evaluate, you know, kind of shaping the future of travel, you think, right now?

[B]

Yeah. So, you know, we've gotten to a place now, you know, it's 2025. It's, you know, five years after the start of the pandemic, and, you know, certainly three years since, you know, the pandemic was dominating our attention. And the pandemic caused us to put a lot of things on hold because we had to get more focused. We had to get focused on our core business again. And, you know, so a lot of things that we believed in, you know, were paused. And, you know, one of those things that we had at the time was experiences. And it's not that we stopped offering them, but we weren't leaning into it as much during the pandemic because, I mean, look, people were socially isolating. They weren't getting together in person. So that product offering kind of, I don't want to say stalled, but, you know, it grew more slowly during the pandemic and subsequent. And, you know, we recently relaunched Experiences and also added to it with something we call Services. And services are basically thinking about all the conveniences that you can find in a hotel and making sure that those things are available to you when you rent a home. So, you know, if you want a personal trainer or a spa or a chef, how can we connect you to one of those people who can do that for you in your home, even when you're in a foreign city, for example, and you don't know who to call and don't speak the language? And how can we make this just as easy to book as a home all through the app? And so we relaunched Experiences and we launched Services with our completely new app integration. And that's been really exciting to be in a place where we can start to innovate and expand into other aspects of travel. Incredible, because I think there's so much more we can do. And as we think about growing our business, we always think about, well, what can Airbnb uniquely do? And how can we leverage our host community and work with our host community to empower people to provide travel services in new ways? And so I think Experience is a great embodiment of that.

[A]

Amazing. What do you think the travel of the future holds? Is it a lot around community and experiences? Is that kind of the big focus you think or is it something else?

[B]

I think since the beginning, we realized that the magic is in the people, right? Like that story from October 2007, when Joe and Brian hosted those three in their apartment. Like, it wasn't just about the affordable place to stay. Obviously, it started with that, right? But it ended with friendship. It ended with, like, Joan Bryan being invited to this guy from India, his wedding, you know, like, two years later, you know, so it was pretty powerful. On a personal level, you know, I think travel at its best, you know, transforms your perspective and makes the world a smaller place and makes. Creates friendships that cross borders. That's the future and vision we're excited about trying to create. And we do that through a product that, you know, creates, you know, first trust. You know, it's a framework for how you can establish trust with someone you don't know, you know, through their reputation, through how we handle the money, you know, through the various protections. But I also think about inspiration, too. And, you know, we have a lot of inspiring spaces that are super fun, and, you know, like, you never knew these things existed, and suddenly you realize on Airbnb they do, and that's inspiring. But, you know, I think likewise with the experiences product, right? Like, it's a whole new travel offering that's, you know, very different from, let's say, the tourist bus that, you know, has traditionally been available to show you around town. And so I think we think there's so many different ways in which we can reinvent the travel offering and open up new destinations that weren't previously on the map. Maybe because they had no infrastructure, maybe they had no hotels, but I think, you know, through the lens of a local, you can really unlock what's special about the place and make something into an experience that wasn't previously. And so, yeah, this is what excites us. And we think there's a lot of new ways to continue to do that.

[A]

Amazing. And so, I mean, based on everything, you know now, Nathan and you guys built, like, such an extraordinary company and unbelievable value across, you know, so many countries. What would you want to tell yourself when you were younger? Like, based on everything that you know now, what. What were some of the biggest lesson or things that you wish somebody told you?

[B]

You know, I. I was often preoccupied with opportunity costs. I mentioned it earlier a little bit, but, like, this idea that there's so many opportunities, and, like, you know, what if I miss out on. On an opportunity, it can be a little paralyzing, you know, like, which direction do I go in? And, you know, I shared a little bit of the criteria and there's some more things too. You know, one is, I think as long as each experience or direction you go in is challenging and you learn, then it's just one step in a journey. It's not necessarily your final outcome. It's building your skill set for that ultimate thing that you do. And so I did a lot of things that were frankly not successful, like a lot of side projects. I didn't mention them here, but, you know, in retrospect, all those things that I did that were ended up being, from one perspective, a waste of time because they didn't work out as it anticipated, were actually super valuable, like skill building opportunities. So that's one. And you know, a funny vignette is like, I went. I was at Harvard, and Mark Zuckerberg is a year younger than me. He was at Harvard too. And I remember he, that first summer when he started the Facebook, put an ad out on the computer science solicitor saying, you know, who wants to join me and go to Palo Alto to work on this thing? And I was like, I told my roommate, that sounds kind of cool, maybe I'll apply. And my roommate was like, no, that sounds stupid. Don't do that. I was like, yeah, you're right, that sounds like, not like a serious thing. So I did it. And so then, you know, a year or two goes by and I'm like, really kicking myself. Like, oh, I could have been like one of the Facebook co founders, you know, had I gone to Palo Alto and not listen to my roommate, you know. And then, you know, fast forward a few years and I have some friends working at Facebook and they invite me to lunch and tell me what they're working on a little bit and try to convince me to join. And like, at this point, they have like 40 engineers. And I'm like, I don't know, you guys are so big already. Like, already you're using all the colleges and high schools. Like, what, what, what more is there to do? You know, like, you guys are done, you're mature as a company. And obviously that was not the case. They were still just getting started. And so again, I was catching myself for not going down that path. And yet, you know, had I gone down that path, I wouldn't have done Airbnb. And so I think, look, there's many right paths. I think the important thing, you can always course correct. And as long as you're learning on whatever path you're on, you're building your skill set to that ultimate thing. There's this article in the New York Times I read a number of years ago about, like, the nature of luck. And, you know, what it says is, like, you know, luck is, like, two things. I mean, there's, of course, some serendipity to it, but, you know, it's also happening. Like, there's opportunity around you all the time. You just have to notice it. Right, Right. And so, yes, of course, there's serendipity, like me finding Joe on Craigslist. There is some serendipity there. Or the other roommate following through. That's some serendipity. But, you know, there's also moments where we saw opportunity, for example, like applying to Y Combinator and getting the serial out. Like, you know, Joe recognized a moment to make an impression right at the right moment. And so I think you can train yourself to notice opportunity that is right before you. And I think. I think we're all surrounded by opportunities. We just fail to notice it. And so I think that's a really kind of important lesson that would have put me at ease as a younger person when I was, like, so preoccupied with, like, how do I become successful? Like, which. Which is the right path. It's like, just, you know, don't worry. Like, actually, any of these can be right paths. Just do one thing at a time. Learn, you know, move on when you stop learning. And be observant. You know, be observant to what's happening around you so that you're ready to pounce when. When you know, the right one comes across your. Your desk or in front of you.

[A]

And create your own luck, which you guys are doing again and again. Again, which is so beautiful. Yeah. Oh, my God, Nathan, this is so good. I can talk to you probably for many, many more hours about leadership or whatever. But seriously, thank you for everything you guys are doing and for changing the world and, you know, just this incredible episode that I know is just pure gold. Thank you.

[B]

It's a lot of fun for me, too. So thanks for taking the time to have me on your program. I really enjoyed it.

[A]

Amazing.

[B]

Across your desk, here in front of.

[A]

You, and create your own luck, which you guys are doing again and again and again, which is so beautiful. Yeah. Oh, my God, Nathan, this is so good. I can talk to you probably for many, many more hours about leadership or whatever. But seriously, thank you for everything you guys are doing and for changing the world and, you know, just this incredible episode that I know is just pure gold. Thank you.

[B]

It's a lot of fun for me. Too. So thanks for taking the time to have me on your program. I really enjoyed it.

[A]

Amazing. I hope you enjoyed this as much as I did. If you did, please share it with friends now. Also, if you're feeling stuck or simply want more from your own career, watch this 30 minute free [e-mail] training. That's leapacademy.com training. See you in the next episode of the Leap Academy with Ilana Golan Show.