How to Scale a Magical Experience: 4 Lessons from Airbnb’s Brian Chesky

Reid Hoffman
7 min readMay 22, 2018

Over the last 20 years, I’ve worked on or invested in many companies that scaled to 100 million users or more. And just about every entrepreneur I meet with has that ambition as they get started. But here’s the thing: You don’t start with 100 million users. You start with a few. And in many ways, the best way to begin is to stop thinking big, and start thinking small. Hand serve your customers. Win them over, one by one. And don’t stop until you know exactly what they want.

That’s what Brian Chesky did. As co-founder and CEO of Airbnb, Brian’s early work was more akin to a traveling salesman. He went door-to-door, meeting Airbnb hosts in person, taking photographs of their space, and learning what they did and didn’t like about his product.

Now this may sound inefficient if you’re an entrepreneur with global ambitions. But I’d argue that painstaking, handcrafted labor is actually the foundation of Brian’s success.

In order to scale, you have to first do things that don’t scale at all.

Today, Airbnb is valued at $31 billion. Eight years ago? A very different picture.

“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,” Brian says, reflecting on Airbnb’s first year and a half.

That was in 2008. Since then, he’s learned a lot about winning over customers. Here are 4 lessons from Brian Chesky from our conversation on Masters of Scale. You can listen to the entire episode here, or subscribe on iTunes, Stitcher, or Google Play.

Lesson #1: Pay passionate attention to your user

“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. If I want to make something amazing, I just spend time with you…. Early on, Joe Gebbia and I literally commuted to New York from Mountain View [to visit our Airbnb hosts in person]. We literally would knock on the doors of all of our hosts. We had their addresses and we say, “Knock knock. Hello. Hey, this is Brian, Joe, we’re founders and we just want to meet you.”

We’d find out ‘Hey, I don’t feel comfortable with the guest. I don’t know who they are.’ Well what if we had profiles? ‘Great!’ Well what do you want in your profile? ‘Well I want a photo.’ Great. What else? ‘I want to know where they work, where they went to school.’ OK.

So you add that stuff. And then you literally start designing touchpoint by touchpoint. The creation of the peer review system, customer support, all these things came from — 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.

I remember we met with a couple hosts…. We walk up to the apartment and we went there to photograph the home. And we’re like, ‘I’ll upload your photos to the website. Do you have any other feedback?’ He comes back with a book, it’s a binder, and he’s got dozens of pages of notes. He ends up creating a product roadmap for us: ‘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.’ I think that always stuck in our mind: The roadmap often exists in the minds of the users you’re designing things for.

Lesson #2: Design an 11-star experience

“If you want to build something that’s truly viral you have to create a total mindf**k experience that you tell everyone about. If I say, ‘What can I do to make this [product] better?’ you’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?’ You start to ask these questions and it really helps you think through the problem.

We basically took one part of our product and we extrapolated: what would a 5-star experience be? Then we went crazy. A 5-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 6-star experience be?’

A 6-star experience: You knock on the door, the host opens and shows you 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 6-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 7-star experience? You knock on the door. The host 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. 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 10-star check in be? 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 it would be just a mindf**k 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 the process is that maybe 9, 10, 11 are not feasible. But if you go through the crazy exercise, 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 and reasonable? It’s actually kind of crazy logistically, but this is the kind of stuff that creates great experience.”

Lesson #3: Create a magical experience… and then figure out what part of that magical thing can scale

“We put up these flyers anonymously saying, ‘Seeking a traveler. We’ll photograph your trip to San Francisco if you let us follow you.’ This guy Ricardo replied. He was from London. We sent a photographer around with him while he was just travelling in San Francisco. What we learned was his trip was awful. He’d show up, he’d go to Alcatraz by himself, put on the headset, and then he’d go to Bubba Gump Shrimp. He’d stay in a budget hotel. He’d go to a hotel bar by himself, sitting with a bunch of dudes at the bar but he doesn’t talk to anyone because he was introverted.

We call him back. We said, ‘Ricardo, we want to create the perfect trip to San Francisco for you.’ We fly him back. We had the team storyboard the perfect experience for Airbnb. We had a driver pick him up at the airport. We took him to the perfect Airbnb. He went to these dinner parties. We got him the best seats at restaurants. We took him on this midnight mystery bike tour.

I see him at the end of the trip. I say, ‘How was your trip?’ He says, ‘It was amazing.’ And then I walk away. He yells at me. ‘Brian, one more thing.’ He starts crying. He breaks down. He says, ‘Thank you. This is the best trip I’ve ever had.’ I was like, ‘Oh my God. I guess it worked. It really moved him.’

I don’t think anyone ever tried to design an end-to-end experience for somebody like they’re in a movie before and we did it. That became a blueprint. We said we are confident on an unscalable basis that we know how to create a trip that deeply moved somebody — that was better than anything they’ve ever experienced. The question is: Can we develop a technology that scales and do it 100 million times?

This is the narrative of every movie you’ve ever seen: A main character starts in an ordinary world. They leave their ordinary world. They cross the threshold to a new, magical world where all these obstacles happen and they overcome something. They call it the hero’s journey. We applied this to trips, built a small team, and we spent the last couple of years figuring out how to scale this. And this has led to what we have today which we call Airbnb Trips.”

Lesson # 4: Take advantage of the time before you scale

“I tell a lot of entrepreneurs who don’t have traction, I miss those times. Yes, it’s exciting to have traction, to have a company that has huge scale. But the biggest leaps you ever get are when you’re small. Another way of saying it is: Your product changes less the bigger you get because there’s more customers, more blowback, more systems, more legacy.

The most innovative leaps you’ll ever make, especially if you’re a network, are going to be when you’re really, really small. You can change the product entirely in a week. Try doing that at LinkedIn or Airbnb today. That would be a huge disaster. So I think taking advantage of that subscale — designing the perfect experience, asking yourself what you can do — is amazing.”

Like These Lessons?

Hear the entire Masters of Scale episode with Brian Chesky; it talks in detail about the theory: that in order to scale, you have to do things that don’t scale at all.