Brian Chesky's new playbook

A lot of founders spend their time based on reacting. So people will email them and they'll wake up and they'll respond to emails, and suddenly their email sets the agenda.

People were describing working 80 hours and getting 20 hours of productive work done, which is just a crazy ratio a week.

There's this negative term called micromanagement. I think there's a difference between micromanagement, which is like telling people exactly what to do, and being in the details. Being in the details is what every responsible company's board does to the CEO.

The role of a leader is to see potential in people that they may not even see themselves.

If we do an AB test, there has to be a hypothesis. If we don't have a hypothesis and A is better than B, then we're stuck with B. And that's a really, really big problem, but we can never change it.

Way too many founders apologize for how they want to run the company. They find some midpoint between how they want to run a company and how the people they lead want to run the company. That's a good way to make everyone miserable. Because what everyone really wants is clarity. And what everyone really wants is to be able to row in the same direction really quickly.

There should be no people managers in the entire company. And when I say people managers, meaning your only responsibility is people, not the work or not the domain.

I think the CEO should be basically the chief product officer of a product or tech company. If the CEO is not the chief product officer then I don't know if they're a product or tech led company.

You can't delegate understanding. If you're going to do AB experiments or measure data, you have to understand what it means.

We wanted a company where a thousand people could work, but it'll look like 10 people did it.

If you want to improve the speed of a company, then make faster decisions. And fast decisions come from a bias of action.

The bigger I get, the more a beginner I tend to feel. It's a weird feeling. I think when I first took off, I think I thought I knew everything or I knew more than I certainly did. But then you get past some peak or you go into this trough where you realize, oh my God, the moment you get to some frontier of knowledge, you start to become a beginner again and everything is new.

Don't feel ashamed to reach out to something for help. It gives a lot of them great honor. The biggest honor most people get in their lives, or one of the biggest honor is when other people ask them for help. Because we all just want to feel useful.

Why don't we just have the best writers do everything? Why is UX writing a separate function? Because actually the emails, the app, the ads should all be one voice.

Don't feel ashamed to reach out to something for help. It gives a lot of them great honor. The biggest honor most people get in their lives, or one of the biggest honor is when other people ask them for help. Because we all just want to feel useful.

Brian Chesky is reflecting on his realization that Airbnb's product had stagnated due to fragmented team approaches rather than cohesive system thinking.

You have to think about the whole cohesive system. And I started realizing that. I asked one person on your team, somebody you know well, and I asked him, I said, 'I feel like I open our app and the product hasn't changed and four years.'

I think the three things are your health, your relationships, and your work. Those are probably the three most important things.

If my life were to end in a year or in 10 years or some time horizon that's shorter than I expected, who are the people I would've wanted to make sure I spent time with?

If there's only one thing I said in this interview today, actually I'm not sure what it would be, but I think a good candidate is try to get everyone to row together in the same direction. Otherwise, why the hell are you all in the same company?

Brian is discussing work-life balance strategies after explaining how getting deeply involved in details initially created more work but eventually freed up his time.

Sometimes you need... Let's say an artist, you have to step away from the painting. And you actually start getting more derivatives, slower and slower.

In this football analogy, "passes" represent big strategic bets or major product changes, while "running" represents incremental optimization and testing.

Think of conversion and growth optimization as like running a football down a field and think of these big leaps as passes. You should probably be doing 80% passes, 20% running the ball down the field, and a lot of companies that do 80% running down the ball down the field and 20% passes.

Instead of one team doing three things, three teams should do one thing.

There's a great saying that the best way to slow a project down is add more people to it.

Five teams should do one thing rather than one team do five things.

The health of an organization, one simple heuristic is how close is engineering and marketing?

You can't build a product unless you know how to talk about the product. You can't be an expert in making the product unless you're also an expert in the market of it.

Chesky uses "semi assembly" to mean a working prototype or demo build, similar to how car companies create partial vehicle prototypes during development.

Every week I would try to see the equivalent of at least a semi assembly of the entire new product we were working on, which allowed me to identify with teams the different bottlenecks happening in the company.

Metrics are going to be subordinate to the calendar. So we're going to have a roadmap. It's going to be a two-year roadmap.

You can't ship something unless it's on the roadmap. So every single thing in the company, with the exception of some infrastructure projects have to be on the roadmap.

A design leader's job should be managing the design first, the people second. How do you manage the people without managing their work? How do you give them development if you're not in the details with them on the work?