The Endless Ambition of Brian Chesky

Building the $95+ Billion Airbnb Behemoth

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On to today’s piece!

Brian Chesky

Brian Chesky, Co-founder and CEO of Airbnb, created a world-changing company that as of this writing is valued at more than $95 billion.

But it’s been quite the journey to get to this point, overcoming problem after problem after problem.

And yet, Airbnb, along with Uber, which I wrote about two weeks ago, became one of the defining companies of a generation.

The story of how Brian and his co-founders built it?

It’s one for the ages.

Let’s get to it.

Early Days

Brian was born in upstate New York and both of his parents were social workers with their main desire for Brian career-wise being for him to have a job that paid him more than they made.

Growing up, Brian never even thought about being an entrepreneur - he wanted to be an artist.

Attending the Rhode Island School of Design (RISD), he’d study industrial design, later mentioning that he was probably born 100 years too late to actually be an artist.

At RISD, Brian competed as a bodybuilder and was even in the 2001 NPC Teen National Championships.

He also got a peculiar assignment that stood out to him years later.

For the assignment, he had to create a self-portrait, something that took him about a week to finish.

After Brian and his classmates completed their assignment, their teacher gave them all another one - create 200 self-portraits.

Clearly, there were not enough hours in the week to complete this seemingly impossible task, and that was the point, as Brian would later mention:

With creativity you can always find a way.

You can design the world around you.

You can live in a world of your own design.

Brian Chesky

At RISD, Brian also became friends with Joe Gebbia. While Brian was leading the ice hockey team, Joe was leading the basketball team, and they both tried to grow the fanbase for sports at an art school - no easy task.

But if they thought that was a challenge, they’d have plenty more years later.

Let’s not get ahead of ourselves though.

After graduating RISD, Brian moved to Los Angeles with a few of his friends and got a job working at a design agency.

While at RISD he was told he could “design the world” and “live in a world of your own design,” in the workplace this wasn’t exactly his reality - He just sat there and did his work.

At 23 years old, disillusioned with the real world, he thought, “This is it?”

He was working a job he didn’t particularly like.

He was commuting an hour and a half each day on the 405 freeway in LA.

He was kinda miserable in LA.

Meanwhile, Joe Gebbia, who was working at Chronicle Books at the time and had his CritBuns product featured in Wired in March 2007, continually tried to convince Brian to move to SF so they could start a company together.

After visiting Joe in August 2007, Brian was finally convinced. He quit his job, and in September drove his Honda Civic with his $1,000 of savings and moved to SF.

Only one problem.

The same week, the landlord raised their rent by 20% and Joe and Brian didn’t have enough money to pay it.

But with creativity, they found a way.

Airbed & Breakfast

Within days of having their rent raised, Brian and Joe found a solution.

A major design conference was going to be in San Franciso in October and they found out that most of the hotels were booked.

They thought, “Why not rent out the extra space in their apartment to make money for rent?”

They had an airbed and they thought they could cook their special guests breakfast in the morning, so they’d call it Airbed & Breakfast.

Joe actually emailed Brian the name:

From: Joe Gebbia

Date: September 26, 2007

To: Brian Chesky

Subject: conference


i came up with a name for turning the house into a place to stay…

airbed & breakfast

ha! will be a simple 4 page site or so.

then it occurred to me that it could be a place for other designer people in san francisco to list a room (or airbed) in their own houses specifically for the conference. and if we hurry we could ping the idsa to put some of their ubiquitous Connecting ’07 ads on it…for a fee, of course.

the ideas never end.


Since Brian and Joe knew some basic HTML, they built the website in 3 days.

They then emailed some design blogs and websites and were mentioned as a place to stay due to the hotel shortage.

They ended up hosting a 35-year-old woman from Boston, a 45-year-old father of 5 from Utah, and a 30-year-old from India.

It was a life-changing experience for them.

It was also the start of something much, much bigger.

From their initial idea, they actually first thought about creating a roommate-matching website, working on it for a number of weeks until they realized they were wasting their time.


Because already existed and they hadn’t even thought to look up competition at that time.

But they quickly evolved.

By February 2008, Nate Blecharczyk, a Harvard computer science graduate who saw an ad for Joe’s apartment on Craigslist, became the third co-founder and roommate.

Moving on from their roommate matching idea, Brian and his co-founders decided to focus on building a platform to provide airbeds for guests attending conferences.

At the time, they thought this idea would pay the rent so they could think of and build the big idea later. Funny how things can evolve.

One of their first launches for Airbed & Breakfast was at SXSW in March 2008.

This turned out to be an important event for them.

At SXSW they met Michael Seibel who founded Socialcam and before joining Y Combinator in 2013.

Why was he important to them?

Because he’d be the one who would introduce them to investors, even though, as you’re about to find out, that wouldn’t go well. More on that in a second.

By the Summer of 2008, Brian and his co-founders had the final version of the product. It was simple and took only three clicks to get to the “book it” button.

Here’s how they thought about the product early on:

It seemed insane that you would actually be able to pay somebody else and be able to book something with them, and you would get a reputation system.

We decided, let's just do it. And at the time we're like, "This is a little too crazy. It's a little too scary. I don't know if we're allowed to do this. I'm not sure if it will work." We decided to do it anyway.

Brian Chesky

Adding payments was just one of the iterations they made.

Early customers asked them a number of questions, but two stood out:

  1. Why does it have to be airbeds?

  2. Why does it have to be around conferences?

Clearly, the niche of airbeds in apartments for guests to stay at during conferences was too small.

So Brian and his co-founders adapted.

With the platform built and an article in TechCrunch in August 2008, they were ready to raise capital.

Raising Capital

In the summer of 2008, Brian and his co-founders go out to raise capital.

They made a 15-slide pitch deck based on Sequoia’s template at the time and included their market size of $30 million, a laughably small amount for what venture capitalists would invest in.

But they didn’t know that.

At one point, they meet Sam Altman, who suggested they change their M’s to B’s in their deck. $30 million market? No, too small, make it a $30 billion market.

But their initial fundraising didn’t go well, even with some introductions made by Michael Seibel:

At this point, I get introduced to a whole bunch of investors. Probably 15 angel investors. We were raising $100,000 to $150,000 at a $1.5 million valuation. We were at $1 million and eventually someone convinced us we'd get a $1.5 million valuation with an extra $50,000.

So we were trying to sell 10% of the company for about $150,000 and of the 15 people we got introduced to, we got introduced over email, I think about six, seven or eight of 'em didn't even reply to the email so we never heard from 'em again. About seven or eight replied, of those, half of them said, "This doesn't fit my investment thesis." Which is weird, 'cause their investment thesis was like consumer internet companies, we were consumer internet, so I assumed that we fit their thesis, but we didn't. Or they said the market wasn't big enough.

One person said, "I'm just not excited about travel as a category," so we're like, "Okay," and then we ended up meeting a few more investors and they all passed on us. The low point was, we ended up launching in August 2008, we meet with the angel, Mike Maples, and we decided, I was so cocky I said, "I'm not even bringing a deck. I'm just gonna show him the live website."

We launched that day on TechCrunch. We had 10,000 people visit our website. I go there without a deck. I have a website, I type in the website, it doesn't work. So I basically sat in front of him for like an hour, and I didn't know what to say. I'm trying to explain to him this concept, and he's like, "I have no idea what you're talking about."

Brian Chesky

One investor, who they met at University Cafe, was drinking a smoothie the whole time, barely looked at them, got up halfway through the pitch, and never came back.


They actually took a photo of the smoothie to remember that moment.

Even worse?

Growth wasn’t happening with the company, even after getting press at the DNC in August:

Barack Obama was coming to Denver. There were 80,000 people coming or there was an 80,000 seat football stadium and they had 27,000 hotel rooms. We thought, "Wow! There's an opportunity here." Plus, it's very grassroots. And we contacted New York Times, CNN and they thought, "What are you talking about? This is crazy. No one's ever gonna stay with other people."

So we ended up just reaching out to the local newspapers. They ignored us, and we had this idea, “Why don't we just start by getting anyone to write about us?”

We felt like if some people write about us, other people would refer to them. So we literally started with bloggers. I wouldn't be surprised if some middle-school student wrote about us for the school paper. But, if we literally got bloggers to write about us, then people would Google "DNC," they would see us come up, 'cause all these bloggers wrote about us. Then the local newspapers would write about us and eventually we worked our way up until CNN, New York Times got it. It started getting traction, but we were still in debt.

Brian Chesky

They got about 80 bookings at the DNC in August 2008 after getting some major press.

But then they only had one or two bookings during the RNC.

And the next week?

Zero bookings.

This was one of Brian’s lowest moments:

So, this is now almost a year into the business. We're tens of thousands of dollars in credit card debt, every investor said no to us, we've launched three times, we've got national press, and we have almost no customers every single day.

And now one of my co-founders decides he's moving to Boston, he's getting engaged, and his fiancé's maybe not interested in living in the west coast and it was unclear if we were gonna stay together as a founding team.

Everyone hits rock bottom, for me this was rock bottom.

Brian Chesky

Brian personally had about $30,000 in credit card debt at this point. Joe had tens of thousands of dollars of credit card debt.

They’ve maxed our card after card until they couldn’t get any more credit cards.

But, they still don’t give up.

Here’s why:

One of the things that kept me going is I remember the worst days at Airbnb were better than my very best days at the job I had before that.

And I said my worst day here is still better than the job I had before because I’m doing what I love and even if I’m failing at what I love, I’m doing it, and there’s something incredibly powerful and special about just the pursuit.

Brian Chesky

So with all of the buzz about the presidential race at the time, they decide to use their creativity and hustle to make enough money to survive.

Here’s the story of how it went down:

We called General Mills, they were like, "What are you talking about? You seriously think we're gonna make unlicensed presidential-themed cereal?" We're like, "Okay, I guess you won't."

And so then, we called these medium-sized cereal companies. They're like, "Great, just send us a non-refundable check for $200,000." I'm like, "OK, that's not gonna work."

So we found this guy in Berkley. He was an alumni of RISD. He says, "I can't print you 100,000 boxes of cereal, but here's what I'll do. I'll print you 1,000 boxes of cereal for free, just give me a royalty." We're like, "Thank you!"

One day, Joe comes back with 1,000 pieces of giant cardboard. I'm like, "What the hell is that?" He's like, "These are the cereal boxes." They were just pieces of cardboard we had to fold and glue into boxes. No one told me that. So, to fund the company we basically folded, like giant origami, 1,000 boxes of collectible breakfast cereal, had to pack cereal in them, and we sold them for $40 a box. We thought, “Who was going to pay $40 a box?” But they were limited edition, so we hand-numbered every one. We called it limited edition. And we ended up selling $30,000 of cereal. And that's actually how we funded the company.

Brian Chesky

They actually created two different boxes of cereal - Obama O’s: Hope In Every Bowl and Cap’n McCain’s: A Maverick In Every Bite.

In October 2008, there was even a TechCrunch article published describing it, which fueled sales:

This week’s award for best marketing promotion related to the election goes to AirBed & Breakfast, the peer-to-peer pad crashing site for travelers. (You list how much per night you want for travelers to stay on your floor, and they book through the site).

Today, I received a package from AirBed & Breakfast containing the two boxes of cereal pictured above: Obama O’s and Cap’n McCain’s. In addition to the physical boxes of cereal, there are two catchy jingles for each cereal (embedded below), and a Webpage where you can vote for the cereal you prefer.


Such a creative and genius move on the part of Brian and his co-founders.

But the cereal money only got them back to zero.

They were still broke.

Luckily, because there were many boxes of cereal left over, they at least had food, though Brian mentions how he lost 20 pounds the first year of building Airbed & Breakfast.

So, they have food, they don’t have any money, and people close to them are very concerned:

I told one mentor of mine about this business. He said, "Brian, I hope that's not the only idea you're working on."

My mom said, "If you need money, you don't need to have strangers stay in your home. Let me send you money."

So people were very worried. And you start wondering about the decisions you've made in life to get here. So I could tell you, I didn't feel successful or smart, or talented at this moment. I felt like the world was against me. I'd go to sleep, my heart pounding every night. I'd wake up like wide awake, like, “What am I gonna do? How am I gonna get through the day? We have no money.”

Brian Chesky

They have one more shot at it, so, finally taking the advice of friends, they make a crucial decision - applying to the startup accelerator Y Combinator.

Y Combinator & Sequoia

Brian and Joe are convinced at a dinner with the founders of in November of 2008 to apply to Y Combinator.

It was a last-minute thing.

The deadline had actually passed the night before, but Justin Khan from called Paul Graham for them, the Co-founder of YC, asking if he could extend the deadline.

He did, by one day.

So Brian worked on the application that night and Joe called Nate, who was still in Boston at the time, to convince him to agree to come to SF if they got in.

They got invited for an interview with YC, and here’s how it went down:

So we meet with Paul Graham at Y Combinator. And he thought the idea was absolutely terrible. In fact he said, "People are actually doing this?" And I said, "Yeah." And the second question was, "What's wrong with them?" And I said, "Oh shit!"

So I thought this was a really bad interview, but by the end of the interview, Joe hands him a box of Obama O's. And Paul Graham thought that we just bought this stupid box of cereal. And he's like, "No, this is how we funded the company." And Paul Graham said, "If you can convince people to pay $40 for a $4 box of cereal, maybe you can get strangers to stay in other strangers homes."

And he also liked us 'cause he said we were cockroaches. And he said, "It's an investment nuclear winter and the only people that will survive are cockroaches, and you're a cockroach."

And so I'm like, "Thank you!" It was actually the nicest thing. For six months, that was the only compliment I got, was I was a cockroach. And I remember calling my mom like, "Mom! I'm a cockroach. I got in!"

Brian Chesky

They got a $20k investment from YC, at a time when Paul Graham actually asked them if they wanted to defer to a later batch because he couldn’t promise them that any investors would show up to demo day at the end of the program because it was during the financial crisis.

Crazy times.

But the experience ended up being a turning point for the Airbed & Breakfast team, which changed its name to Airbnb by the end of the program in March 2009.

Why was the program so impactful?

Two reasons.

First, Brian and his co-founders finally had structure:

The first thing Y Combinator did was, it basically created a structure for us to work on it full time, and live together.

So in other words, we were all kind of working on it, but it was like everyone had other things going on in their life. And I think the enemy of a start-up is everyone else's life. It's true. You have a life and you have vacations and you have conferences and you go away and you do other stuff and it's like, that's the enemy of start-up.

You know, Paul Graham used to say, "Start-ups don't die, they just fade away."

And so, you know, we basically decided, for three months, Nate would move from Boston to San Francisco and we'd wake up at 8:00. We'd go to bed at midnight, seven days a week, and we'd work from eight to midnight, every single day. And seven days a week, we'd get a full night's sleep, but that was it. And we would, in that dedication for three to four months, created this real serious rhythm where we weren't doing other things. We were totally focused.

Brian Chesky

Second, Brian learned from Paul Graham some of the best advice he got:

“It’s better to have 100 people that love you than a million customers that just sorta like you.”

Hearing this was a game-changer:

So Paul Graham said, "All you have to do is get 100 people to love you. Don't worry about millions of people." That was totally freeing. 'Cause until then I was like, "How the hell am I "gonna get a million people to do this if I can't even get my mom or my sister to do it?" But I can find 100 people.

And so we literally decided, do things that don't scale. If all you need to do is get 100 people to love you, do things that don't scale. It turns out, 100 people that love you is really hard, 'cause it's easy, 100 people to like you, 100 people to love you means you need to meet them. You need to understand their problem. And so we literally would fly, during Y Combinator, from Mountain View, we commuted from Mountain View to New York.

Joe and I would go to New York, and we'd go door to door, 'cause New York was where most of our community was. And we would meet with every one of our hosts. And we'd live with them. We literally would live with them, we'd write their first reviews for the places. And in fact, I would go there and I would be like, "Wow, the photos are terrible! This is actually a really nice house." And the host was like, "Well, I can't figure out how to get photos onto my computer." This is before really the iPhone and high quality camera. This was like people had to plug a camera into their laptop.

So we thought, "What if you just clicked a button and a photographer next day would magically show up and photograph your home?" And we thought that would be amazing.

And so I went home with Joe and we borrowed a camera from one of our friends in Brooklyn who was a photographer, and we knocked on the door and they're like, "Hello?" Yes, I'm here, the photographer. And they're like, "Wow, this is a small company, the founders also photographing my home."

I used to also carry a bank ledger in my backpack. And if you need to get paid, I'd just write you out the check and knock on your door hand you a check. So, that was also a reminder of how small we were. But the point was that doing things that don't scale.

Brian Chesky

By April 2009, they had hundreds of people who loved them.

Their hard work also paid off, with Sequoia Capital investing $600,000 into Airbnb valuing them at $3 million.

The crazy part?

In a 3-month time period, Brian and his co-founders went from being untouchable to raising money from arguably the best venture capital firm.

Three months.

But they were just getting started and many challenges were ahead of them.

Early Growth, Struggles, and Competition

How did Airbnb grow beyond that initial community in NYC?

Events, PR, and word of mouth, often doing things that didn’t scale:

On Airbnb, the hosts were in New York but the travelers came from all over the world. So people from all over the world would hear about and discover homes in New York. They would travel to New York, and they'd also travel to San Francisco, and then they'd go back to their city and they'd spread the idea.

The other thing is they would go from a guest to a host. And so the network naturally grew. But we also targeted events, so... We targeted the Democratic National Convention. We built D.C. through the inauguration 2009. We focused on music festivals and concerts. The World Cup, the Olympics, these are early, not the most recent one, but the one before. So events and PR were probably the main ways that we bootstrapped.

And then we built this one-click post-to-Craigslist tool, that Craigslist allowed us to do until they shut it off a couple years into it. But, we allowed hosts to basically, with the single click of a button, click and distribute their post to Craigslist to get more distribution. And so the listings would get re-listed onto Craigslist and they would feed back.

We started a little bit of Google advertising. But the main way it grew was through word of mouth and PR. And PR, we used to promote the events. We didn't have any partnerships. We tried to partner with event companies. We tried to partner with, partnerships in your early stage company I found never work, 'cause there's so much red tape and paper that by the time you ever get done, you're dead.

And so, but PR is super. If you've got an idea that's noteworthy, people will talk about it. And almost the more absurd the idea, in some ways, the better, because it's worth writing about. Like, it was absurd people were doing this so they couldn't stop writing about it. And so that was actually a good thing. Being kind of a provocative idea was good to get the word out.

And then we thought, "if we just get enough people to use it, "they'll tell everyone else about it." And so this idea primarily grew through word of mouth.

And then we would go to cities and then we would educate the host. We would do these meet-ups. So we'd go to a city, and we called it turning on a market. We would do a meet-up. We would meet the 10 or 20 hosts, we'd educate them.

Brian Chesky

Throughout this, they kept getting press and people kept hearing about them and telling their friends.

Airbnb raises a $7.2 million Series A led by Sequoia Capital and Greylock Partners in November 2010.

The Airbnb team was also growing, eventually having 17 people working out of their 3-bedroom apartment, so Brian decided to spend about 10 months staying in different Airbnbs in San Francisco, staying in each place for 3-5 days.

Not only did it show his team just how passionate he was about the business, but it also helped Brian meet more hosts and continue to learn from them.

This community building paid off when in June of 2011, the Samwer brothers, creators of Rocket Internet, and notorious for cloning high-growth U.S.-based startups, building them in non-English speaking markets, and trying to sell them back to the originators, launched Wimdu, an Airbnb clone, with $90 million of funding.

It was a huge threat to Airbnb.

And the Samwer brothers didn’t exactly play nice.

An email from Airbnb to their hosts outlined some of the tactics being deployed against them. There were a few:

  • They falsely claim to be affiliated with Airbnb or be the “international version” of Airbnb.

  • They claim that they are part of eBay and/or Groupon. We’ve confirmed that this is not the case.

  • Their employees pretend to be Airbnb travelers in order to give you a sales pitch in your home.

  • They are duplicating personal profiles, descriptions, and photos of your Airbnb listing without your permission.

But Brian wasn’t going to allow them to play their typical game and get a fat payday for selling to Airbnb a few years later.

He took a different approach:

I didn't say this to Oliver Samwer, but my view was, my biggest punishment, my biggest revenge on you is, I'm gonna make you run this company long term. So you had the baby, now you gotta raise the child. And you're stuck with it for 18 years. 'Cause I knew he wanted to sell the company, I'm like, "No, no. You're running this company."

And I knew he maybe could move faster than me for a year, but he wasn't gonna keep doing it. And so that was our strategy. And we built the company long term. The ultimate way we won is, we had a better community. He couldn't understand community. I think we had a better product. It was a do-or-die time.

We ended up flying to Europe, we hired bunch of country managers, we flew them all to San Francisco and we basically trained them for a month or two. We said now go to your countries, hire your team, here's how you open a market, here's how you open cities and we opened, I think like 8 or 10 offices in like three months. It was actually totally insane. We hired hundreds of people and the whole speed of the company picked up at that point. And a couple years later, obviously, it was game over.

Brian Chesky

The month after Wimdu launched, a woman’s apartment was ransacked with her writing a blog post detailing the horrors of what she came home to.

It was terrible, but Brian took ownership of their errors in response.

At the time, Airbnb had just raised $112 million and was valued at more than a billion dollars, but just 10 months before, they were only 10-12 people working out of a 3-bedroom apartment. Their customer support was run by one intern. This is important for context, not an excuse.

Because of the apartment ransacking, they had to build more infrastructure.

Brian led the charge.

A Fast Company article mentioned his approach:

For a long time, Chesky’s relentlessness meant he was running the company like a rhinoceros: Point him in the right direction and he’d put his head down and hammer out a solution.

When a guest ransacked a host’s apartment in 2011, he managed the potentially crippling PR nightmare with such fierce attention that it actually led to features that improved the service’s professionalism and trust, including 24/7 customer service and comprehensive insurance coverage.

Fast Company

The lesson Brian learned?

Don’t fall behind in operations or hiring.

The same year, they hire Belinda Johnson as their first legal officer. She’d eventually become COO and she was the one who, when Airbnb was battling city officials to make Airbnb legal, encouraged Brian to meet the people who disliked him.

She said that it was hard to hate you up close, once they had a better understanding.

So Brian did.

And he had to treat every city personally, something he would deal with for years, and something Airbnb still deals with today.

Project Snow White

By January 2012, Airbnb had its 5 millionth booking on the platform.

Though Brian and his team have always been focused on designing a great experience for guests and hosts, they take things up another notch at this time, with a special initiative: Project Snow White.

Inspired by reading a section from a biography of Walt Disney about the production of Snow White, with Walt using storyboards to map out the entire film, Brian decided that was just what Airbnb needed to create the perfect end-to-end experience for guests and hosts.

He actually hired a Pixar animator to help storyboard the entire customer experience.

And designing this experience, an 11-star experience more specifically, is something Brian would famously describe:

If you want to build something that’s truly viral you have to create a total mindfuck experience that you tell everyone about. We basically took one part of our product and we extrapolated: What would a five-star experience be? Then we went crazy.

So a one-, two-, or three-star experience is, you get to your Airbnb, and no one’s there. You knock on the door. They don’t open. That’s a one star. Maybe it’s a three star if they don’t open, you have to wait 20 minutes. If they never show up, and you’re pissed and you need to get your money back, that’s a one-star experience. You’re never using us 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: You knock on the door, the host opens. “Hey, I’m Reid. Welcome to my house.” You’re the host in this case. You would show them around. 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. The whole thing is great. That’s a six-star experience. 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? You knock on the door. Reid Hoffman opens, [you] 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. By the way, here’s my car. You can use my car. And I also want to surprise you. There’s this best restaurant in the city of San Francisco. I got you a table there.” And you’re like, “Whoa. This is way beyond…“

So what would a ten-star check-in be? A ten-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 cards 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 it would be just a mindfuck experience.

So what would an 11-star experience be? I would show up at the airport and you’d 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 the sweet spot. You have to almost design the extreme to come backwards. Suddenly, doesn’t knowing my preferences and having a surfboard in the house seem not crazy but reasonable? It’s actually kind of crazy logistically, but this is the kind of stuff that creates great experience.

Brian Chesky

The same year, when Hurricane Sandy hit, Airbnb offered up free rooms to help people.


The reason is simple:

When in doubt, we’re just going to go above and beyond for customers.

Brian Chesky

By June 2012, Airbnb was up to ten million total bookings on the site, and by the end of the year international expansion was in full swing and they made a number of acquisitions to fuel their growth.

The next year, Brian worked his magic to lure another key employee to the company and they’d make some big moves shortly after.

Chip Conley

By 2013, 10% of Airbnb’s business includes sublets, stays 30 days or more, and Brian fully believes fewer people will have one-year leases, instead opting for the flexibility of long-term stays on Airbnb.

The same year, they hire Chip Conley, an innovator in the boutique-hotel aesthetic.

Here’s what led them to Chip:

One of Chesky’s strengths is his humility in recognizing his own deficiencies as a leader, and his willingness to look to others for wisdom. In addition to seeking help from Donahoe and Sandberg, he also spoke to Amazon CEO Jeff Bezos, who recently told him, “This company is going to be massively successful as long as you don’t fuck it up.”

Chesky has consulted with Groupon cofounder Andrew Mason on international expansion, former CIA director George Tenet on corporate culture, and even Apple design SVP Jony Ive on product design.

But none of those heavyweights could give Chesky the deeper education he needed on how to run a hospitality company. He wanted a mentor who could have more impact on Airbnb than on himself.

In early 2013, Chesky and his senior executives met with people from traditional hotel groups. “[They didn’t] inspire us or fit with our culture,” Chesky says. “That’s what led us to Chip.”

Fast Company

But Chip was semiretired at the time.

How did Brian convince him to join Airbnb?

The two stayed in touch last spring, and by June, Chesky had made up his mind: This was the guy. The rhino had a target in sight.

He offered Conley a full-time job, yet Conley declined. He was pretty happy living a sun-kissed life trotting the globe in search of the next Burning Man. But Chesky kept up his charm offensive.

“I’ll never forget it,” recalls Laura Hughes, Airbnb’s global hospitality lead. “Brian was like, ‘I’m going to dinner tonight with Chip, and when I come back, he’s going to be an employee.’”

Chesky had hoped to get Conley to agree to consult eight hours a week. Before dinner was over, he had persuaded him to commit to 15 hours.

Fast Company

So now that Chip was on board, what were some of the changes Brian made?

For starters, they changed their office design, something Brian at the time described as a competitive advantage for them in hiring:

One of the things we decided was, how can we reinvent the office? There were like 100 ideas, but I'll just give you one of 'em.

One of our offices that we had, you walk in the lobby and there were photos of our homes around the world. And so you go to this lobby, and I remember people were just walking in our lobby and lookin' at all of these homes, like, "Oh, these are awesome." And I thought, I couldn't figure it out, but I thought there's gotta be a better way than just showing photos of our homes. And I couldn't figure it out.

One day, I'm walking home, I'm walking from my house to -- I'm walking down the street. And I pass a furniture store and it's late at night and the furniture store was lit up. They light it up at night and it's like, there's a floor-to-ceiling window. And I just look in and it's a showroom. They've basically recreated these rooms. And it was hilarious. I thought it'd be really funny just to have a meeting in the showroom. And in fact, the next day I took somebody to a meeting in the showroom and we were hanging out in the dining room of a furniture store, but you feel like you're in a living room. It was actually kind of fun. It was kind of absurd. You're like having a meeting in Ikea, but it was actually kind of fun.

And suddenly we realize, what if all of our meeting rooms were actually modeled piece by piece after apartments on our website. And we ended up doing that.

And so, I remember one time we emailed somebody. We said, "Hey, do you mind if we recreate your home "in our office?" And they were like, "What?" And I'm like, "Yeah, all I need is an inventory of everything in your home." And so some people did it, and we literally recreated the rooms.

So you go there and our meeting rooms are literally homes you walk into. Like showrooms of our homes. It's a subtle little reinvention. It doesn't cost a lot of money 'cause people's homes, the furniture they put in is actually cheaper than most office furniture. It's really creative and we have tens of thousands of people a year who fly or come to our office to tour our office now and our office has become a huge competitive advantage in hiring. 

Brian Chesky

Wired magazine would call it “The Envy of Silicon Valley.”

And Airbnb was rolling.

In 2013, more than 10 million guests stayed in an Airbnb and the company did more than $250 million in revenue.

The next year, building on that idea of designing an amazing experience, they launch Instant Bookings, with 41,000 properties offering the feature by March.

They also launch a huge redesign of their site and branding, a full-service cleaning service, and a bump to their liability insurance program, providing $1 million worth of protections for hosts and landlords.

Over the next few years, Brian and his team would continue their crazy growth, charging towards an IPO.

Of course, they couldn’t foresee what would happen in 2020.

Managing the Pandemic Drop

When the COVID-19 pandemic hit, Airbnb lost 80% of its revenue in 8 weeks.

80% of their revenue.

8 weeks.

Let that sink in.

Brian had to lay off 25% of his employees.

Right before the pandemic, Airbnb had 10 divisions, growth had slowed, and they were spending lots of money on performance marketing, preparing for a potential IPO coming up.

What did they do after that drop?

They rebuilt from the ground up.

Pay was reduced for all executives, the performance marketing budget was set to zero (Much like what Ooshma Garg of Gobble was forced to do to save her company), and Brian instead did 100 interviews that year to help grow the company.

Brian would later say that COVID completely changed how they ran the company.

They became totally integrated into one roadmap and, counterintuitively, Brian decided they weren’t going to do anything more than what he could focus on.

He would spend his time reviewing work and hiring people and Airbnb would become laser-focused in all regards.

It paid off.

Airbnb would become a public company with its IPO in late 2020.

The year before the pandemic, Airbnb lost a few hundred million dollars, but by the end of 2022, they had $3.4 billion in free cash flow.

How does Brian prioritize, allowing for that focus at Airbnb that drove the turnaround?

It’s a science and an art.

The science:

The first thing we do is we try to just take in all the inputs. So, what are the inputs we get? Inputs are customer service calls. Inputs are social media posts. We do tens of thousands of listening sessions with guests and hosts and then inputs are like basically user behavior right?

You can see what people are clicking. You can see retention. You can see when somebody churns and then if there's a party and we don't handle it right, they churn, they don't come back, and then we see people in their network don't list and you can start to measure that so those are your inputs.

You basically now have an organization of maybe millions of issues and you can bucket them to like say 100 or 200 types of things.

The next thing you do is you look at the frequency and the severity. 

So severity might be like a safety issue, very infrequent, but when it happens is really serious.

A frequent issue is like I'm upset with a refund. Not as severe but very frequent, that happens all the time.

Then you then you start to look at relationships. Like, you know, we notice a lot of hosts are complaining about pricing being confusing, a lot of guests are complaining that hosts are charging too high fees, and then we start to realize, wait a second, if we make it easier for hosts to price and they understand what guests are actually paying they might actually do a better job pricing and guests won't complain as much. So you start to find connections, so that's the science part.

Brian Chesky

And then there’s the art:

The art part now it's actually picking stuff because you have a list, you have some matrix, like severity, frequency, this and that, but the real ability is the art form of a group of 10 or 20 of us deeply understanding the issue so well.

We live the product. We use the product. I host, I've read thousands of things, you just take thousands of inputs you put them in your head and then you just go through and you can't paint by numbers, you can't be purely algorithmic, that's why that's the art, you could, but I think it's never as good as your intuition, but your intuitions form all these data points.

Brian Chesky

The science and the art allow Brian and his team to move the company forward.

And what does part of that include?

The launch of new products, something Airbnb is able to do only when they’ve gotten permission from customers to do so:

I like to tell people we have to have permission by the customer to do something new and we only have permission to do something new if they love what we currently do and if they're complaining on Twitter about upfront pricing, about doing chores when they check out, about customer service taking too long, then we don't have permission.

They don't want us to do something new because they're gonna think we're gonna bring problems to that category, so I told the team, “We have some big ideas, AI is going to unlock so many of them, but we don't have permission to do new things until people love our core service, so we're going to basically create a blueprint of every single thing people are complaining about.

Brian Chesky

15 years in, and they still have a lot more to build.

What’s Next?

A number of things stand out about Brian, but one, in particular, is worth mentioning - he’s a learning machine.

He’s learning from customers, from competitors, from founders in adjacent industries, from history’s greatest founders - it’s nonstop.

Reid Hoffman once mentioned that after speaking with Brian at a conference that the first thing Brian did after getting off stage was ask Reid how he could improve as a speaker.

This quest for knowledge has certainly paid off in the past, but, more importantly, bodes well for Airbnb’s future, of which AI is undoubtedly on Brian’s mind:

Albert Einstein used to have a saying, “The best way to keep your balance on a bicycle is to keep moving,” and I think the best way to keep your balance in the world of AI is to keep moving forward and just adopt the tools don't fight it and see where it takes us but it’s going to be pretty wild…

I think trying to ban AI is like trying to ban electricity, you're going to be on the wrong side of History. The Genie is out of the bottle you can't put it back in the bottle.

Brian Chesky

And what would Airbnb’s role be in the world of AI?

Brian describes it as being more like a travel community, with Airbnb being, “The ultimate AI concierge or the ultimate host,” with the ability to anticipate the needs of their guests and create a more immersive interface and experience with the help of AI.

Should be fun watching what they build next!

Brian’s Wisdom

In each edition of the Just Go Grind newsletter, I like to include a few more quotes at the end from my research into the founder who is featured, sharing their wisdom.

All these really good ideas, or big ideas, often sound like stupid ideas. Somebody once told me in the early days, “Don't worry about anyone stealing your idea. If it's any good, everyone will dismiss it.” And that was exactly the truth.

Brian Chesky

I think that Airbnb before the pandemic probably raised too much money. And we didn't raise as much money as others. I think that in hindsight not having as much money means you have constraints. Constraints means you have to say “no,” you have to make hard decisions.

Brian Chesky

On culture:

So you have to basically be relentlessly doing cultural things every week. And so, I do as many cultural things as I used to do, but now they're no longer person-to-person.

The main leverage points I have now with culture is having people do things on my behalf. You would call it leverage. They're doing it for you.

So in the early days, I did all the interviews. Then I trained people, I hand picked people and I said you should do the interviews and here's what you interview for. So I spent days with them showing them how to interview. So then they started interviewing. Then we had all these people, so I had to create an inner circle that trained those people. I used to meet every single employee and give them a personal orientation.

Then I started doing weekly orientations to groups of people. And now we've recorded it all 'cause we hire people all over the world and so we've institutionalized this whole on-boarding week and we carry all the videos and stories, I do the Sunday night email series, I think you've seen some of the emails.

Every Sunday night, I write an email to the company that's not really a tactical email, but a more, kind of, above the trees, kind of, fairly thought provoking, kind of cultural email. Because I find that, if, on your first day, you say something to somebody, they kind of remember, but then a hundred people said a hundred things after that. So you have to continue to repeat things.

So I think culture is about repetition. It's about repeating over and over and over again the things that really matter at a company. And then, it's about trying to design as many things, like the space, when you check in, there's a key card, and when you check your key card, above it says, "Champion the Mission," it's one of the values and it reminds you every day to do that. So there's a lot of subtle things that we do. And I think it's like that touch point. What is every moment that can be designed to reinforce how you want people to value things. And it all can be designed.

Brian Chesky

On valuations in 2013:

None of our valuations are really that real without liquidity for the value of the company. I try not to let this go to the heads of us or the employees. We’re not successful yet. We’re successful when we’re profitable for a really long time and we’ve truly delivered on our promise for millions of customers all over the world and we’ve created this new economy around sharing that’s all over the world and that’s a lot of years away.

Brian Chesky

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