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Brian Chesky
Co-Founder, Chief Executive Officer, Head of Community & Chairman of the Board, Airbnb Inc

#326: Reid Hoffman of LinkedIn, Brian Chesky of Airbnb, and How to Scale to 100M+ Users

📅 Jul 24, 2026 BlackNova Productions 38 MIN 58 SEGMENTS · 6 SPEAKERS
"In order to scale, you have to do things that don't scale." — Reid Hoffman This episode is a showcase from Masters of Scale (https://mastersofscale.com/) , one of the few podcasts I recommend repeatedly to entrepreneurs. It's a conversation between LinkedIn co-founder Reid Hoffman (@reidhoffman (  / reidhoffman  ) ) and Airbnb co-founder Brian Chesky (@bchesky (  / bchesky  ) ), and it focuses on how you can scale your company by, paradoxically, doing things that don't scale. This is, in some ways, part two of my conversation with Airbnb's co-founder Joe Gebbia (which you can check out he...

What Brian Chesky said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Brian Chesky, co-founder and CEO of Airbnb, discussed the company's early struggles and the principle of doing things that don't scale. He described being $25,000 in credit card debt and creating Obama O's and Captain McCain's cereal, selling 1,000 boxes at $40 each to raise $40,000. Chesky recounted Paul Graham's advice to go to users in New York, leading to door-to-door visits and a professional photography service. He explained how user feedback shaped features like profiles and the peer review system. Chesky detailed the star-rating exercise for designing a perfect experience, from a six-star welcome gift to an 11-star trip to space. He discussed scaling challenges, including a 2011 incident where a woman's home was trashed, and the need for 24/7 support and trust and safety teams. He described hiring a Pixar storyboard artist and creating a perfect trip for a traveler named Ricardo, which became the blueprint for Airbnb Trips. Chesky advised entrepreneurs to dream big but act small, as the biggest leaps happen when small.

Key takeaways

  1. Chesky said the biggest innovative leaps happen when a company is small, and entrepreneurs should take advantage of that subscale.
  2. Chesky described creating Obama O's and Captain McCain's cereal, selling 1,000 boxes at $40 each to raise $40,000.
  3. Chesky said Paul Graham told him to go to his users in New York, which led to door-to-door visits and a photography service.
  4. Chesky said a 2011 incident where a woman's home was trashed forced Airbnb to build 24/7 support and a trust and safety team.
  5. Chesky said he hired a storyboard artist from Pixar to design the perfect Airbnb experience, leading to Airbnb Trips.

Numbers and commitments

FigureWhat it refers toTypeAt
$25,000 Chesky's credit card debt at Airbnb's early stage metric 5:16
50 people a day Daily website visitors in early Airbnb days metric 5:57
10 to 20 bookings a day Daily bookings in early Airbnb days metric 5:57
1,000 boxes Boxes of collectible breakfast cereal made and sold metric 1:24
$40 a box Price of the collectible breakfast cereal price 6:25
$40,000 Revenue from cereal sales metric 6:25
7% of global GDP Travel industry size as share of global GDP metric 10:25
5 and 7 trillion Travel industry market size in dollars metric 26:15
500 trip packages Number of trip packages unveiled in November 2016 metric 32:56
12 cities Number of cities with trip packages in November 2016 metric 32:56

Chapters

  1. 0:00Early struggles and cereal fundraising
  2. 10:56Paul Graham's advice and user visits
  3. 12:34Designing with empathy and user feedback
  4. 15:51Star-rating exercise for perfect experience
  5. 20:03Handcrafted work and scaling transition
  6. 26:15Scaling challenges and organizational growth
  7. 28:33Reinventing travel with storyboarding
  8. 29:58Creating the perfect trip for Ricardo
  9. 31:56Airbnb Trips and scaling the experience
  10. 33:13Advice for small entrepreneurs

Questions asked in this interview

7
  1. 0:24I usually drink it in the mornings and frequently take their travel packs with me on the road. So, what is AG1?
  2. 1:24So, with much further ado, much further ado. What?
  3. 13:02Was there a particular experience that has really stuck in your mind?
  4. 14:54So you need to exercise judgment in discerning will this particular user and particular feedback lead me to the mass market or is it an edge case?
  5. 17:34So, what would a 10-star check-in be?
  6. 18:39And then I need to design the elements that get me into the totally doable thing.' So, how does Brian decide on the doable thing?
  7. 29:24What are the essential ingredients that make a vacation truly memorable?
Tim Ferriss 0:00 ↗
Optimal minimal. At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question? Now, it is a perfect time. I'm a cybernetic organism living this year over metal endoskeleton.
This episode is brought to you by AG1, the daily foundational nutritional supplement that supports whole body health. I do get asked a lot what I would take if I could only take one supplement. And the true answer is invariably AG1. It simply covers a ton of bases. I usually drink it in the mornings and frequently take their travel packs with me on the road. So, what is AG1? AG1 is a science-driven formulation of vitamins, probiotics, and whole food sourced nutrients. In a single scoop, AG1 gives you support for the brain, gut, and immune system. So, take ownership of your health and try AG1 today. You will get a free 1-year supply of vitamin D and five free AG1 travel packs with your first subscription purchase. So, learn more, check it out. Go to drinkag1.com/tim. That's drinkag1.com/tim. Last time drinkag1.com/tim. Check it out.
Well, hello. Hello. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss Show, where it is my job normally to deconstruct world-class performers through interviews, whether they're from business, sports, entertainment, military, otherwise to tease out the habits, routines, favorite books, and so on that you can use. In this episode, I'm going to let someone else do the heavy lifting. And he's very, very qualified. Reid Hoffman on LinkedIn and Twitter as Reid Hoffman. REI is a frequent flyer of sorts on this show. He is often referred to as the Oracle of Silicon Valley by tech insiders who look at his company building and investing track record with awe. The companies include Facebook, Airbnb, Zynga, Flickr, and many, many, many others. Reid is well known as the co-founder of LinkedIn, which has more than 300 million users and sold to Microsoft for 26.2 billion. Prior to that, he was exec vice president at PayPal, which was purchased by eBay for 1.5 billion. And at PayPal, he was nicknamed firefighter chief by the then CEO Peter Thiel, who's also been on the podcast. And Reid is widely considered one of the most successful angel investors of the past decade. He is now a partner at Greylock Partners, a top tier venture capital firm. And on my phone, there are very few podcasts that I listen to multiple times. There are very few podcasts that I recommend over and over and over again to other people, especially entrepreneurs. And what I'm going to showcase in this episode is a conversation between Reid and Brian Chesky, who is a co-founder and CEO of Airbnb. And there are a couple of other cameos, and I'm doing this for a number of reasons. Number one, if you want to learn how to scale your company from whatever the number might be to 100 million, 200 million users, paradoxically, you can increase the likelihood of success by doing things that do not scale. And this is a really critical concept to understand and it's best done through examples. And that is why I want to showcase this discussion which is from the first season of Masters of Scale and I really, really hope you enjoy it. I loved it and Joe Gebbia, co-founder of Airbnb has been on this podcast before and we covered his development as a designer and an entrepreneur leading up to the original development of the business model for Airbnb. That was part one and I promised a part two. So this is in some ways that part two exactly and Masters of Scale is a great show if you haven't seen it. It showcases famous founders and innovative leaders and so on sharing their lessons for success and there is a brand new season out right now. The new season includes episodes with founders of Spotify, Instagram, TaskRabbit, Shake Shack and Glossier among many, many others. You can subscribe to Masters of Scale on Apple Podcasts or learn more at mastersofscale.com. So without further ado, please enjoy this short episode with Reid Hoffman, Brian Chesky, and many others. And if you've heard me recommend 1,000 True Fans to you many, many times before as the article you should read if you're only going to read one article on marketing, which is by Kevin Kelly. You can find it on kk.org. This is the audio complement to that. So, with much further ado, much further ado. What? Much further ado, please enjoy.
Brian Chesky 5:16 ↗
Joe and I are broke. We're losing weight and I don't have a lot of weight to lose. You know those binders that you put baseball cards in? We put credit cards in them. At this point, I am $25,000 in credit card debt. Joe is tens of thousands of dollars in credit card debt. So, this is like make or break. We need a lifeline.
Reid Hoffman 5:35 ↗
That entrepreneur in need of a lifeline, that's Brian Chesky, co-founder and CEO of Airbnb, a service that lets you rent a couch for the night or a cabin or a castle. Today, Airbnb is valued at $30 billion. 8 years ago, a very different picture.
Brian Chesky 5:57 ↗
We have this website and maybe 50 people a day are visiting it and we're probably getting like 10 to 20 bookings a day. So, and by the way, we've been working out for a year and a half. So, for anyone who's worried your company doesn't have traction, that was our traction.
Reid Hoffman 6:09 ↗
It was 2008, an election year in the United States. Barack Obama is running against John McCain. You needed a tax cut. Brian was at the Democratic National Convention hatching a PR campaign for Airbnb, one that could rescue the company and their credit card bills.
Brian Chesky 6:25 ↗
Joe and I look at each other and we said, 'We're Airbed and Breakfast. The air beds aren't going so well. Maybe breakfast will.' As we thought, what if we could sell breakfast? Maybe we can make some money. What's a non-perishable breakfast? Cereal. And so we thought, the presidential campaign's coming up. We just launched with the DNC. What if we created a Barack Obama themed breakfast cereal? And we thought, what would a Barack Obama themed breakfast cereal be called? Obama O's like Cheerios, the breakfast of change. We thought, well, we want to be a nonpartisan website, so we'd also have to need a John McCain themed cereal. And that's a no-brainer. John McCain was a captain in the Navy. And so we came up with Captain McCain's like Captain Crunch, a maverick in every bite. We ended up making a thousand boxes of collectible breakfast cereal. We sold them for $40 a box. That's $40,000. Not bad for pocket change. And it got them through a cash crunch, but it came at a cost. We had to physically make the breakfast cereal ourselves. Meaning, we get a printed poster board and we had to fold it and hot glue it. No one told me I had to hot glue breakfast cereal. And they should call it burn glue because every time you get on you, you burn you. And I had a perfect 1:1 ratio of burn to box. And so I literally had to hot glue a thousand boxes of cereal. At one point in the middle of the night, I remember reading, 'I wonder if when Mark Zuckerberg started Facebook, he had to hot glue breakfast cereal.' The answer was no. And this was not a good sign.
Reid Hoffman 7:51 ↗
But what was a good sign was Brian's willingness to work with his hands, burns and all. I'd argue that painstaking handcrafted labor is actually the foundation of his success. In order to scale, you have to do things that don't scale.
This is Masters of Scale. I'm Reid Hoffman, co-founder of LinkedIn, partner at Greylock, and your host. On this episode, I'll make the case that the only way an organization can truly scale is to first do things that don't scale at all. I'll try to prove that theory through stories from some of the smartest entrepreneurs I know. Over the last 20 years, I've worked on or invested in many companies that scaled to 100 million users or more. But here's the thing, you don't start with 100 million users. You start with a few. So stop thinking big and start thinking small. Hand serve your customers. Win them over one by one. Now this may sound like odd advice if you're an entrepreneur with global ambitions. Mark Zuckerberg didn't personally invite 1.8 billion people to Facebook. He built a great product and the users just poured in. Right. Not exactly. On this show, I'll dispel that myth by talking to founders who fought to win their users. I'm starting with Brian Chesky, CEO of Airbnb, because he epitomizes the idea of handcrafting the user experience before you start to scale. It's a principle he first absorbed in design school.
Brian Chesky 9:47 ↗
I was doing medical design once. I had designed a children's ventilator. I had to sit in the shoes of the child and so I had to like imagine being a child, get in like the operating table and like you have to put yourself in the shoes of the patient or the person using your product. And if you're only doing A/B tests, like you're never designing with empathy.
Reid Hoffman 10:06 ↗
But a funny thing happened to Brian when he moved to Silicon Valley. He sort of forgot about designing with empathy for a single user. It's a common mistake amongst entrepreneurs with global ambitions. They have to promise investors the world. Tens of millions of customers, billions in revenue. It's intoxicating. Just listen to Brian go.
Brian Chesky 10:25 ↗
This is a travel industry that is something like 7% of global GDP. Somewhere between five and 7 trillion, 10 times the market size of Google's market size.
Reid Hoffman 10:35 ↗
And Brian might have stayed in the stratosphere if not for a fateful meeting with Paul Graham, the co-founder of Y Combinator. Y Combinator is a startup incubator which cultivates and invests in early stage companies. Brian was admitted to Y Combinator in 2009 and his first meeting with Paul was confounding. Paul tends to stump people with deceptively simple questions.
Brian Chesky 10:56 ↗
And he asked us, 'Where's your business?' And I go, 'What do you mean? Like, where's your traction?' I go, 'Well, we don't have a lot of traction.' He goes, 'Well, people must be using it.' I said, 'There's a few people in New York using it.' And he said something I'll never forget. He said, 'So, your users are in New York and you're still in Mountain View.' I said, 'Yeah.' He said, 'What are you still doing here?' And I go, 'What do you mean?' He said, 'Go to your users, get to know them, get your customers one by one.' And I said, 'But that won't scale. If we're hugely millions of customers, we can't meet every customer.' And he said, 'That's exactly why you should do it now because this is the only time you'll ever be small enough that you can meet all your customers, get to know them, and make something directly for them.'
Reid Hoffman 11:32 ↗
Brian and his co-founders followed his advice to the letter.
Brian Chesky 11:36 ↗
We literally commuted to New York from Mountain View. So, we would be in Y Combinator for was it Tuesday night dinners, and then Wednesday, Joe and I would go to New York. We literally would knock on the doors of all of our hosts and we had their addresses and we say knock knock. Hello. Hey, this is Brian and Joe. We're founders. We just want to meet you. It's a little creepy just to knock on the door unannounced. We needed excuses to get in their home. So, they came up with an offer that the host couldn't refuse. We'd send a professional photographer to your home and photograph your home. Of course, we didn't have any money and we couldn't employ photographers. So, Joe and I, we'd show up at their door and they're like, 'Wow, this company's pretty small.'
Reid Hoffman 12:11 ↗
These home visits became Airbnb's secret weapon. It's how they learned what people loved.
Brian Chesky 12:18 ↗
It's really hard to get even 10 people to love anything. But it's not hard if you spend a ton of time with them. So if I want to make something amazing, I just spend time with you. And I'm like, well, what if I did this? What if I did this? What if I did this?
Reid Hoffman 12:29 ↗
From those questions, a handcrafted experience is born.
Brian Chesky 12:34 ↗
We'd find out, hey, I don't feel comfortable with the guest. I don't know who they are. Well, what if we added profiles? Great. Well, what do you want in your profile? Do I want a photo? Great. What else? I want to know where they work, where they went to school. Okay, so you add that stuff and then you literally start designing touch point by touch point. The creation of the peer review system, customer support, all these things came from us. Literally, we didn't just meet our users, we lived with them. And I used to joke that when you bought an iPhone, Steve Jobs didn't come sleep on your couch, but I did.
Reid Hoffman 13:02 ↗
Yes. Was there a particular experience that has really stuck in your mind?
Brian Chesky 13:05 ↗
I remember we met with a couple hosts and it's winter. It's snowing outside and we're like in snow boots and we walk up to the apartment and we went there to photograph the home and we're like, 'Hey, I'll upload your photos to the website. Do you have any other feedback?' And he comes back with a book. It's like a binder and he's got like dozens of pages of notes and he ends up creating like a product roadmap for us like we should have this, this, this, this, and this. And we're like, 'Oh my god, this is our roadmap.' Because he's the customer. And I think that always stuck in our mind as the roadmap often exists in the minds of the users you're designing things for.
Reid Hoffman 13:45 ↗
It is typical to get very detailed feedback from some of your early users. And if you're not getting some people who say, 'This is super important to me. I love this. I really need this to work well,' it usually means you're off track. Passionate feedback is a clue that your product really matters to someone. And one passionate user can turn into many if you listen to them carefully. It's essential to get this kind of feedback early while you're still defining the product. It's like setting a foundation as an architect. You wouldn't build a skyscraper before you've built a solid foundation. User feedback ensures you won't build a dozen floors on an unstable swamp. Brian has a simple method for extracting detailed feedback from users. He doesn't ask about the product he already built. He asks about the product of their dreams.
Brian Chesky 14:33 ↗
We'd ask these questions like, 'What could we do to surprise you?' like what could we do not to make this better but to make you tell everyone about it and the answer is different. If I say what could I do to make this better they'll say something small. If I were to say Reid what would it take for me to design something that you would literally tell every single person you've ever encountered. So you start to ask these questions and it really helps you think through this problem.
Reid Hoffman 14:54 ↗
It's essential to seek out and listen to user feedback. But the caveat is you have to figure out which users to listen to. You're gonna have different kinds of users giving you feedback and some of it will take you in the wrong direction. So you need to exercise judgment in discerning will this particular user and particular feedback lead me to the mass market or is it an edge case? For example, at LinkedIn we had one group of users who invent a name for themselves. They called themselves LIONs, which is LinkedIn Open Networkers, because their theory of the world was that everyone wants to directly connect to everyone else in the world because that's the way they wanted it. But they're actually not the majority case. A lot of people who are very busy, who have access to resources, who have some celebrity status do not want that. And if we followed their feedback, LinkedIn would not be where it is today. We had to steer away from a bunch of passionate users who told us very explicitly that we were fools for not following their advice.
Brian Chesky 15:51 ↗
If you want to build something that's truly viral, you have to create a total like mind experience that you tell everyone about. And so we basically took one part of our product and we extrapolated what would a five-star experience be and we went crazy. So a one, two or three star experience is you get to your Airbnb and no one's there. So you knock on the door, they don't open, that's a one star, you know, or maybe it's a three star. If they don't open, you have to wait 20 minutes. And if they never show up and you're pissed and you need to get your money back, that's one star. You're never using those again. So a five-star experience is you knock on the door, they open the door, they let you in. Great. That's not a big deal. You're not going to tell every friend about it. You might say, I used Airbnb, it worked. So we thought, what would a six-star experience be? A six-star experience. Knock on the door, the host opens. Hey, I'm Reid. Welcome to my house. You're the host in this case. And you would show them around and on the table would be a welcome gift. It would be a bottle of wine, maybe some candy. You'd open the fridge, there's water, you go to the bathroom, there's toiletries, and the whole thing is great. That's a six-star experience. And you'd say, 'Wow, I love this more than a hotel. I'm definitely going to use Airbnb again. It worked better than I expected.' What's a seven-star experience? Knock on the door. Reid Hoffman opens. Get in. Welcome. Here's my full kitchen. I know you like surfing. There's a surfboard waiting for you. I've booked lessons for you. It's going to be an amazing experience. And by the way, here's my car. You can use my car. And you know, I also want to surprise you, but I got you there's the best restaurant in the city of San Francisco. I got you a table there. You're like, whoa. Like, this is way beyond.
Reid Hoffman 17:34 ↗
Adding stars clearly excites Brian. It took some time to run through this mental exercise. We'll skip ahead to the 10-star experience. So, what would a 10-star check-in be?
Brian Chesky 17:42 ↗
A 10-star check-in would be the Beatles check-in in 1964. I'd get off the plane and there'd be 5,000 high school kids cheering my name with cars welcoming me to the country. I'd get to the front yard of your house and there'd be a press conference for me and I would be just a mind experience. So, what would an 11-star experience be? I would show up to the airport and you would be there with Elon Musk and you're saying you're going to space. The point of the process is that maybe 9, 10, 11 are not feasible. But if you go through the crazy exercise of keep going, there's some sweet spot between they showed up and they opened the door and I went to space. That's a sweet spot. And you have to almost design the extreme to come backwards suddenly. Doesn't just like having like knowing my preferences and having a surfboard in the house seem like not crazy and reasonable. It's actually kind of crazy logistically, but this is the kind of stuff that creates great experience.
Reid Hoffman 18:39 ↗
But how far do you go toward the 11-star experience to create the Nirvana product? All successful entrepreneurs at some point have to come back down to earth. There's really two stages of a startup's product. The first design a perfect experience and then you scale that experience and that's it. But which part of the perfect experience do you scale? So the most ambitious entrepreneurs, let's call them the Elons after my friend Elon Musk, probably get there through raw energy because they're convinced they need to solve a problem. And the unscalable thing is one step that they have to push through on the way. The Elons say, 'I'm going to Mars, but first I've got to solve this problem right in front of me. First, I need to get that rocket launched, and I need to have a business model for that first rocket, and that looks like satellites.' Okay, I'm going to try satellite launches. And how do I get my first rocket? I need to create a scalable rocket platform, but unless I get the first rocket up, it doesn't matter. And you kind of work back to that. Then you've got folks like Brian who say, 'I realize that to get this awesome experience, I have to ratchet back to something that still seems like magic, but is totally doable. And then I need to design the elements that get me into the totally doable thing.' So, how does Brian decide on the doable thing? He settled on a service with the appropriate level of magic and started building it. And here's the next thing to notice. They didn't launch perfectly scaled services. They built everything by hand.

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APA

Chesky, B. (2026, July 24). #326: Reid Hoffman of LinkedIn, Brian Chesky of Airbnb, and How to Scale to 100M+ Users [Interview transcript]. BlackNova Productions. CEOInterviews.AI. https://ceointerviews.ai/interview/1128562/

MLA

Brian Chesky. "#326: Reid Hoffman of LinkedIn, Brian Chesky of Airbnb, and How to Scale to 100M+ Users." BlackNova Productions, 24 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/1128562/.

BibTeX
@misc{chesky2026_1128562,
  author       = {Brian Chesky},
  title        = {#326: Reid Hoffman of LinkedIn, Brian Chesky of Airbnb, and How to Scale to 100M+ Users},
  howpublished = {Interview transcript, BlackNova Productions. CEOInterviews.AI},
  year         = {2026},
  month        = {jul},
  url          = {https://ceointerviews.ai/interview/1128562/},
  note         = {Speaker-attributed transcript with timestamps}
}