Naveen Mandava
8 min readMay 26, 2017

13 must-read insights from Brian Chesky’s handcrafted building experience for AirBnB

If Steve Blank saida startup is an organization formed to search for a repeatable and scalable business model” then Brian Chesky’s conversation with Reid Hoffman gives a visceral narrative of that search phase. Here are the top 13 insights:

1. “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 huge and we have 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.”

2. 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. And I’m like, “Well what if I did this, what if I did this, what if I did this?” From those questions, a handcrafted experience is born.

3. 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 as, the roadmap often exists in the minds of the users you’re designing things for.

4. 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. CHESKY: We’d ask these questions like, “What can we do to surprise you? What can we do, not to make this better, but to make you tell everyone about it?” And that answer is different. If I say, “What can 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?” You start to ask these questions and it really helps you think through this problem.

5. 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?

6. There’s really two stages of a startup’s product. The first is design a perfect experience and then you scale that experience. That’s it.

7. 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. “What would a six star experience be?” So what would a ten star check in be? The point of the 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 and reasonable? It’s actually kind of crazy logistically, but this is the kind of stuff that creates great experience.

8. We had a saying that you would do everything by hand until it was painful. So Joe and I would photograph homes until it was painful, then we get other photographers. Then we’d manage them with spreadsheets until it was painful. And then we’d automate the tools to make her more efficient. Note how they gradually worked out a solution. They didn’t guess at what users wanted. They reacted to what users asked for. Then they met the demand through a piecemeal process. And here we come to the true art of doing things that don’t scale.

9. it’s worth dwelling on these early days of handcrafted work, because most entrepreneurs tend to have a funny reaction to these experiences. They may laugh about it later. They may call the work unglamorous. They may celebrate the day they could hire a helping hand or automate these chores out of existence. But thoughtful founders will never say, “What a complete waste of time.” They’ll often look back on this period as one of the most creative phases of their careers.

10. The transition from the handcrafted phase to the massive scale phase is a challenging one. And I want to dispel any illusions that you can switch from one to the other with ease. In fact, it requires two opposing mindsets. You have to fully empathize with a single user. At the same time, you have to worry about everyone. I like the way that Brian describes the difference. Brian — The designing of experience is a different part of your brain than the scaling your experience. It’s a different skill set. The scaling experience is a highly analytical, operations oriented, and technology oriented problem. The designing of experience is a more intuition based human, empathetic, end-to-end experience. One parallel might be writing and editing. So the handcrafted phase tends to be more like writing: It’s a more inventive and creative process. Whereas the scaling phase tends to be more analytical. It’s more like being an editor. At that point you tend to do more pruning. You realize: “Well this whole thing is magical. But if we focus on this 20 percent, we get 80 percent of the magic.” So you prune. You compact. You distill. And you architect, so it can now run at a rocketship rate. You’re transitioning the product or service over to a scale organization that can now run it. The organization needs a simple plan with very few errors and very little improvisation.

11. I would argue that the sharpest founders never fully abandon the mindset, no matter how big their company gets. The organization will start having antibodies against new handcrafted things. It’s a response that protects organizational efficiency. It says: “Look, this new thing? We can’t get it to scale. It won’t operationalize. It won’t fit within our process.” The reason that scaled companies have a hard time with this handcrafted process is all in the list of objections about why this won’t work, why this shouldn’t be integrated as part of the company. And so what you need to do as a founder is to be extremely choiceful of which handcrafted innovation you choose, and how you protect it organizationally. You need to protect it because the natural reaction of the scale organization will be to kill it. He wanted to reinvent the industry again, and he knew he had more to learn about the travel experience in order to do it. So he turned to Hollywood for help. CHESKY: I often find that to reinvent an industry, you do not take inspiration directly from that industry, you need to look at orthogonal industries. For us the orthogonal industry for travel was cinema. The best trips you’ve ever seen are the trips that characters in movies have and we would provide that analogy in real life. I actually literally hired a storyboard artist from Pixar. We had him storyboard the perfect Airbnb experience. When we did that we realized there was this two hour movie and only 20- minutes were in the home. There was all this leading up to the home, getting the airport, going around, going to dinner, or hanging out with friends out and about. Most of the trip was not in the home. We realized at that point, we need to be the end-to-end business of travel. So the same way that we did things that don’t scale, we called it “magical trips.” We decided let’s find one traveler and create the perfect trip for them.

12. What are the essential ingredients that make a vacation truly memorable? It’s a question Brian can’t even begin to answer until he delivers that experience to at least one person. You’re about to get a master class in handcrafting. CHESKY: 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 him while he was just travelling in © 2017 Wait What LLC, All Rights Reserved 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, there are all the services. He went on these dinner parties, we got him the best seats at restaurants. We took him on this midnight mystery bike tour. Sixty riders go on it and nobody but the leader knows where it will end up. There was this crazy magical world. 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’s better than anything they’ve ever experienced. The question is: Can we develop a technology that scales and do it 100 million times? HOFFMAN: Notice here how quickly Brian switches back to the analytical mindset. He can extrapolate from a single journey to a list of essential ingredients.

13. Dream big. And act small. Pay passionate attention to your users. Handcraft the core service for them. Create a magical experience. And then figure out what part of that magical handcrafted thing can scale.

By now you would have guessed that the whole piece is worth listening/reading for every startup!

Listen or Read Handcrafted — with AirBnB’s Brian Chesky