A Bit of Optimism - The Secret Art of Micromanagement with Airbnb CEO Brian Chesky

Episode Date: February 11, 2025

People aren’t born great leaders. They learn to become great leaders.For Brian Chesky, the learning never stops. As the co-founder of Airbnb, he had to transition from an impassioned entrepreneur with a brilliant idea into a CEO responsible for thousands of employees. To make the hard decisions necessary for Airbnb to survive the COVID pandemic, a cataclysmic event for the travel industry, Brian had to lean into the skills and thinking he’d learned and practiced for over a decade of leadership.I’ve watched Brian grow as a leader for years, and so I was delighted to sit down with him for a conversation on what people get wrong about great leadership. He shares with me the difference between micromanagement and “eyes on” leadership, why leaders should fight the instinct to be liked, and why an existential crisis is the best thing to put a company’s values to the test.This…is A Bit of Optimism.For more on Brian and his work, check out:airbnb.com

Has being a weightlifter made you a better executive? Absolutely. Bodybuilding taught me that you build your life one repetition at a time. That it's all about consistency. That there's not one moment that you get into shape. Leadership isn't something innate. It's something we have to learn and practice. I got to meet Brian Chesky, the CEO

and one of the founders of Airbnb a whole bunch of years ago. And unlike other leaders I've met, I had the chance to watch him grow as a leader. What started as air mattresses in their living room, literally an air bed and breakfast, to a company now worth $80 billion, Brian has navigated countless challenges, all with vision and resilience.

Brian doesn't believe that Airbnb has reached its peak, and he doesn't think he's hit his full potential as a leader either. It's a powerful reminder that leadership is a continuous journey and not a final destination. This is a bit of optimism. I have seen who you've become in the world of leadership, and I love listening to people tell me that they got information, direction, inspiration from you. It's been great to watch the journey. Oh, thank you so much, Simon.

I mean, one of the most important characteristics for a leader, I think it's curiosity and the ability to learn. Because like when I started Airbnb, I was like 26, and I don't think most people would have hired me to be their intern. And so how do you go from that to leading thousands of people running a public company? My parents are social workers. I had no real model for leadership. So everything was like just discovering it one foot in front of the other. And I'm a student, I feel like I'm still a beginner, still learning. And I think that like, being a founder, I felt like was very intuitive. Like I was pretty good the first time I was a founder. I think being a leader and a CEO is

not intuitive. And I think almost nobody is born a good CEO. And I think a lot of your instincts are to like want to be liked and do things to be liked and avoid conflict. And so I think your instincts sometimes aren't always correct and you have to really learn it. And it was a very long journey to go from being a good founder to a not good CEO to hopefully a much better CEO. You know, you were very good about asking advice and you're very good about getting outside points of view. What advice did you blindly follow in the early days because the person you were asking advice from was highly regarded or famous or a big deal in the business world?

And if you got that advice today, you'd be like, absolutely not. I think in Silicon Valley, in particular, there's this whole like venture capital industrial complex developed around companies. When I joined Y Combinator, Y Combinator is like famous incubator, they give you a t-shirt and there's these white letters and the front of the gray t-shirt and it says, make something people want. It's like the best mantra for like starting a company. It's very simple. If you make something people want or even love, the best mantra for like starting a company. It's very simple. If you make something people want or even love, they'll tell other people will grow.

And it really focuses your company in the most important thing. We are a company. We live to make a product or service and we should make it really great. But then once you go to an adventure capital industrial complex, what ends up happening is there's this really like intense focus on growth. And that is within reason good, like companies need to grow because growth is like oxygen, you need momentum. And especially it comes like Airbnb is a network effect. You need more people to use it for the utility to grow and there's gonna be competition and you wanna,

it's kind of a race a little bit. But I think there was like this temple of growth that you worship. And the problem is, and we've talked about this, it's like you've talked about like our goal is to go north, but where exactly are we going? We wanna go north or our goal is to go 60 miles an hour. But which way?

I don't know, but we have to go 60 miles an hour because investors like cars that are going fast. We gotta go at the speed limit. And so where are we trying to go? But I think that what we ended up doing in the hyper growth era is we focused so much on growth that I think we really traded both profitability and efficiency, but more importantly, quality of the service.

And I learned the hard way because when the pandemic hit, I went on Simon like one of the craziest 10 year runs ever in Silicon Valley. 2010s from 2010, 2020, we went from a like $70 million company to a $30 million company. It's only happened a few times before. It was a rocket ship. We got to the pandemic, then we lose 80% of our business in eight weeks.

People start asking, is this the end of Airbnb? Will Airbnb exist? This is around the time I went on your podcast the last time. And I felt like our business flashed before our eyes. And it's almost like you have this near-death experience. We had a near-death business experience. And in that moment, it became so clear to me that the way out of this crisis is get back to the basics, to get back to making something people want. And so we got back to focusing on making hundreds and hundreds of improvements. And that's kind of me undoing a lot of the advice that I got.

I don't blame anyone for listening to their advice, but everyone is telling people to grow. And I think the best thing you can do is focus on creating something great. And if you do, customers will follow you. No one cares how fast you're growing. No one cares that your company is succeeding. They care about themselves

and if you're enriching their life. And so I think that's the key. And so that was probably a big lesson for me. What you're basically articulating beautifully is what it means to be customer focused. Like I think people overdo or sort of don't really understand what customer focus means. And it is a very simple idea was, as you said, which is make something people want, which might be different than what your venture capitalists want, which might be different than whoever else has skin in the game want. And this is the great irony. We're going to talk about these things like they sound profound, but it's so stupid, the things that we're saying, which is for business succeed, somebody has to buy the thing you're

selling and then keep buying it. That's pretty much it. And you run an efficient business so that it's profitable. It's amazing because people go to business schools and the business school has a way of making the business sound so complicated that you lose sight of the fundamentals. You need to make something people want and you need to build a company people want to work at. It's actually very freaking simple and everything else are constraints, they're guardrails.

But I remember somebody once telling me like numbers the language of business and I remember thinking to myself, no, they're not. Numbers are just the language of board meetings and their language of shareholders. But that doesn't mean it's the language of a business. The language of a business is if people actually love your product and they want to buy it. The other thing, Simon, is like, I'm a designer by training. And so I started looking at like how are companies designed? And I did a talk.

It was supposed to be an off the record talk at Y Combinator, but Paul Graham was sitting in the audience, decides to write a blog post about it. And he calls it founder mode. He basically said there's these two modes running a company, one with a manager mindset, one's a founder mindset. I never coined it that but I basically had a few principles. And I think the most important principles were if you're a leader, you should be in the details. And being in the details doesn't mean you tell her what to do. You can still trust people, but you're in the details like if you're like a general, you're on the battlefield with them. Now, you might trust them, but you can't support them and help them if you are on the battlefield with them. And the other principle is getting the entire company to row in the same direction. If I have a thousand people, I'd rather a thousand people in one ship than a

thousand people in a thousand little boats going in different directions. This may sound obvious to people listening. This sound might sound like the way everyone does it. This is not how almost any fortune 500 company runs. Almost every fortune 500 company, they manage the company through numbers. They divisionalize the company. The CEO is often not in the details, they are not rowing in the same direction. And they're trying to make the quarter or to make the plan. This has become the the

kind of conventional way companies are run. And I think that there's a different way of doing it. So when you talk about founder mode, what I'm curious about, is it something that is constantly on? Or is it something that you turn on when you need it? mode, what I'm curious about, is it something that is constantly on or is it something that you turn on when you need it? And here's where the question is coming from, which is we don't fully understand military leadership as civilians, right? We think these officers and NCOs walk around barking orders at everybody and everybody has, yes, sir, yes, sir, yes, ma'am, yes, ma'am, and sort of just follow blindly. And that command and control

is necessary, but it's not always on. So like in peacetime or in training, there is question and asking and leaders do get input and feedback from their folks, from their troops. And they then use that information to make decisions. But in the chaos of warfare, a good leader turns on the switch of command and control does bark orders, does not want to hear your opinion, but trust has been built already because of all of the interaction prior, so that now they follow the orders blindly, not purely because of the authority structure, but because they trust their leader. And they know that their leader wouldn't put them in harm's way unnecessarily, even if mistakes are made. But when they leave the chaos of combat, that switch is turned off. And I think a lot of CEOs have this sort of like

either command and control or micromanagement because they think that's what works best. Is that what founder mode is? Is it something that you always have? Or is it is it situational? And if so, what are those situations? I do think there's more hands on leadership moments and more hands off leadership moments. Let hands-off leadership moments. Let me give you an analogy. I'm a pretty bad golfer, but I've taken a couple golf lessons.

One of the worst things you can do if you learn golf is to teach yourself your own swing. If you teach yourself your own swing, you're going to teach the wrong swing. Then the more you golf with the wrong swing, if you do get an instructor, it's going to take them longer to fix your swing. You really need the instructor to teach you the swing, and you really don't wanna swing without the instructor for a while, but eventually, hopefully, you're able to swing a club without an instructor there,

and they're only occasionally checking up on you. To me, that was the analogy for how I had to get Airbnb. I wanted Airbnb to be the most creative place on Earth, an incredible execution company, some of the best people of our generation. And I really wanted to establish a standard of excellence. So what I did is five years, I got very, very hands-on. And I said, I'm trying to teach a standard.

I wanna calibrate that standard, but over time, this is gonna become muscle memory and I will have to be as involved and I'll be more selective in where I'm hands-on and where I'm involved. So I reviewed every single thing we shipped. Over time, I've been able to let go and the standards become self-reinforcing.

And then when I get involved now, new teams that need new standards, if I need to increase the standards or I need to change direction of the company, like we need to do something different. And that's now how I can be more selective. To give you a really specific example, a press release. When I first really took back the reins of the company, I said, I want

to do everything perfectly. So our first press releases, I was editing with the team. We probably did like 70 edits of the press release. And you think that doesn't justify the few reporters that ever read it. But I wanted us to learn how to be perfect about something and like really establish a standard of excellence. And over time, each press release, I would do fewer and fewer edits where now I just look at it, write my quotes, do a little bit of editing

because that's real muscle memory. So to me, just to summarize, rowing in the same direction, being in the details, being small lean, being long-term, these I think are always on. There's something in the military, General McChrystal, being long-term, these, I think, are always on. There's something in the military General McChrystal told me, eyes on, hands off. People think you're either hands on, eyes on, or hands off, eyes off. And General McChrystal,

who actually ran Joint Special Operations Command and JSOC with the special operations reported to and famously gave them a lot of autonomy, did say there was a leadership principle of eyes on, hands off, but you're still eyes on. And I think that I don't think being eyes on necessarily means we're a micromanager because you're not actually hands on. I want to push a little bit because I think so often good advice is given of which this is among that I think people misinterpret and misunderstand because I still want to try and understand the nuance of when this becomes micromanagement. Because even something like Eyes On Hands Off feels to some people big brothery. And you have to show me everything.

I'm not going to be working on it. I'm not going to write the press release with you, but I want to see everything before it goes out. And I understand what you're saying and understand that there is a difference. But what I'm trying to parse out is somebody who will use your words to justify being a micromanager or follow your advice incorrectly and become a micromanager by accident. Yeah, yeah. I mean, like you're having, we're having like the crux of the conversation.

What is a micromanager and is it even bad? And I don't even know if it's ever been properly defined. So I don't know if I can argue whether it's, it's certainly a pejorative. Like it's got a negative association. It doesn't feel good when it's happening to us. Potentially. I will tell you as a CEO of a public company, like I don't feel micromanaged, but I do feel like the board like kind of sees everything and I operate under a policy of transparency.

I think the shareholders see a whole lot as well. I'm pretty transparent in my employees. So I think people are pretty eyes on in my job and I don't feel micromanaged. Just to give you a quick story about micromanage. I remember asking Johnny Ive this question. Johnny Ive was the head of design at Apple and Steve was famously in the details. I mean, Steve was, I think one of the greatest CEOs

last 50 years. And I asked Johnny Ive, I said, did you ever feel micromanaged by Steve Jobs? And he said, no. And I said, why? And he said, because he was partnering with me. And so to me, this is the nuance. I have an executive once said, is this your job or is this my job? I remember saying to them, it should never be either. To me, that's the secret. You don't do your job. I don't do my job. We do the job together. We're on the field together.

We're on the field together. And so if I'm not in the details, if I'm not there with you, I can't help you. And if I can't help you, I'm not adding any value. And so how can I help you? It's not about telling you what to do. I don't really tell a lot of employees what to do. I do set standards. I'll tell them if I like something or don't like something, but they have a opportunity to disagree. And often they convince me that this is the best way to do it. But the most important thing is this creative partnership. They're like, what about this? And have you talk to them? And what about these three?

And we're a functional organization, Simon. So I need to make sure engineering is talking design, is talking to marketing, is talking to sales, is talking to the creative team, is talking to the lawyers, talking to policy. So it's kind of a way of synthesizing things together. But I think that's the nuance. I mean, by the way, in a functional organization,

I can't really tell people exactly what to do. Like I'm not an engineer, so I can't really tell the engineers exactly what to do because I don't even know engineering as well as they do. I can't tell the lawyers how to do their job. But what I can tell them is the outcome I want. And I can say, are we really at the edge of what's possible? And have you talked to them? And what if we did this? So it's really this like partnership. And that's what I think great leadership can be. It's actually a resource and a partnership. And then the question is, why can't be everywhere all at once?

So there are gonna be teams where they only need me episodically. And there are gonna be teams where I'm on the field a lot more. But I think there's a shift that goes from teaching to actual partnership where like, I'm not the expert teaching you. I have held you to a standard where it's now muscle memory,

but now we're partnering together. And I think that to me is the secret. Has being a weightlifter made you a better executive? Absolutely. Bodybuilder for sure. I mean, by the way, you know, the old saying- Bodybuilder, sorry. Yeah, weightlifter, bodybuilder. Yeah. You know what it is? There's an old saying, like, you can't get in shape in one day. And so like, if you decide one day you want to get in really good shape, going to the gym for 10 hours isn't gonna help you.

In fact, it's gonna be counterproductive. You can only instill so much trauma on your body in one moment. I mean, this is a side note, but I was 16 years old. I was the skinniest person probably in my high school. And I said, I wanna be one of the most muscular teenagers in the country. And I wanna, I felt like if I could change my body,

I could change my life. I was like 16, 17 years old. This is in the country. And I want to, I felt like if I could change my body, I could change my life. I was like 16, 17 years old. This is the nineties. I taught myself weightlifting, taught myself bodybuilding and bodybuilding taught me that you basically like you build your life one repetition at a time. That it's all about consistency, that there's not one moment that you get into shape. That you actually, it's about the discipline and consistency of one year after the other after the other, and that you're improving like point 1% every day. But if

you compound point 1% every day, consistently and never quit and keep going, that you'll reach the mountaintop in Airbnb was like a RISD project that we just never stopped. It was like the world's biggest RISD project, like this is where I went to school, and we just never stopped in 17 years later of consistency. You know, just like if you can like change your body, you can change your life, the same thing with Airbnb. If you can change a company, how a company runs, you can potentially change the entire industry. So let's talk about that. You're bodybuilding and you badly rip a muscle, things happen, you get an injury, you, I don't know,

you go skiing or something and it goes sideways, literally and figuratively. You're not sure you'll ever be able to bodybuild again. This was COVID for you, as you said, it was traumatic, sudden. And I'm so curious, how many companies went out of business because of the shock of COVID and how many companies went out of business

because they didn't know how to manage through the shock of COVID. And yours, superficially, you're in the travel business, you shouldn't be sitting here right now. And I'm very curious how you took a company that got smashed in the face, kept the lights on long enough that you could sort of limp through and then how you rebuild it. Yes, Simon. One of our board members, this is an interesting story, is a guy named Ken Chenal. He was the CEO of American Express during 9-11 and the 2008 financial crisis. And Ken Chenal told me before the pandemic, he said, at least once in your career, you're going to have to deal with a 9-11 or 2008.

It's going to be your defining moment as a leader. Andy Grove had a quote. Andy Grove was former CEO of Intel. He said, bad companies destroyed by a crisis. Good companies survive a crisis. But great companies are defined by a crisis. So I always had in my mind that I would have a defining moment, and I didn't know what it was.

And then the pandemic broke out. The world had shut down, and Ken called me. And he said pandemic broke out. The world had shut down and Ken called me and he said, remember the whole conversation I had with you about your defining moment as leader that you'll have in 9-11 or in 2008? He said, this is not like 9-11. This is like 10 9-11s at once. I think you learn a lot about people in a crisis.

And the thing I learned most about in the crisis was myself. And I think the hardest thing to manage in a crisis is your own psychology. Because I think the hardest thing to manage in a crisis is your own psychology. Because I think the psychology of the leader becomes the psychology of the organization. And I think it really matters. And I think if you ask, why me?

Why is this happening? Oh my God. And if you look to the employees to reassure you, then I think that's gonna be a mentality that's gonna like permeate the organization. If you're paralyzed, you can't make decisions. If you make decisions out of fear, not hope and love, then you're going to probably make the wrong decision. I never heard anyone make a good decision out of fear, by the way. But if you can tell yourself, this is my

defining moment. Well, if it is my defining moment, how do I be remembered? I'm remembered for being bold. I'll be remembered for being courageous. I'll be remembered for this being my best moment. I want to be optimistic. I am going to be optimistic because that mentality is what's going to create creativity and curiosity, and it's going to make us brave to actually handle the crisis. And I am going to model the behavior. And I think that's ultimately what I tried to do.

And hopefully, most people felt like a whole bunch of us were in the foxhole. And I'm one of those people that, like I'm actually like calmer in a crisis. I don't know what it is. It's almost like my mind and body find equilibrium. And I'm one of those people that when everything speeds up, I slow down. And I just became very, very clear.

And I realized the world still needs Airbnb. People are asking if we're going to exist. It was a burning house. We were going to lose half the things. You have to ask yourself, well, what's most important? And to us, what was most important was getting back to the basics, back to the roots of Airbnb, back to building that community, back to doing what was most important to build the service that people love, connecting people together, making them feel like they can belong in any community in the world.

That's all I agree. And that's all fine and good and absolutely with the mindset. But you still had the reality that there was no money coming in and nobody was using the service. And I'm very curious. Yes, you had to make a lot of hard decisions. What actually happened? What did you actually do to keep it alive? Those courageous, bold decisions that you wanted to be remembered for, what were they?

Yeah. So I had a board meeting. The first thing I said is I wrote down a bunch of principles and I said, hey, listen, I'm going to have to make a whole bunch of decisions. I'm not going to be able to run every decision by you. This is kind of speaking to the crisis. So let's agree on some principles. The first one was act decisively. The second was preserve as much cash as possible. The third was try to be heroes, not villains of a crisis. The fourth was, let's prepare to win the following travel season. We're gonna be on offense.

So the first thing I did was I increased communication amongst my board and employees. I had a all hands meeting every week, counter intuitively. I answered every question people ask. And some of the advice was, don't do team meetings because you might get asked if there's gonna be a layoff and you don't wanna have to answer the awkward question. And I just said, all things are on the table. We're looking at it.

And I just tried to be as honest as possible. I spoke to every board member every week. We had weekly board meetings, not quarterly board meetings because I felt like we had to communicate. That's the first thing. The second thing we had to do was we had to simplify the company. So we audited all the projects in the company. There were over a thousand projects and programs happening in the company. I said, this is going to be the ultimate editing process. The house is on fire, you can't do everything. We probably cut 70 to 80% of the projects. It was a mass exercise in prioritization.

Then we looked at organization. We said, we do have too many people. We need to preserve, you know, like we're a ship. We need to preserve the supplies because this storm might go on longer than ever. We made a very difficult decision to lay off 25% of employees. I tried to make sure that we weren't algorithmic in the way we cut. So I literally look through every single person.

There's no way I made the perfect decision. But I said, I don't want to emotionally detach from the decision. I'm going to be as close to this decision as possible. We got rid of layers of management. We took pay cuts. We did a number of things to really simplify the company. And I think we handled the layoffs with quite a bit of compassion. And I remember writing this layoff letter that got quite a bit of attention

because I think we really, really went above and beyond to take care of people that were affected. We even created an outplacement agency to find other positions for them. We created this alumni directory. We gave people like a year of health care when that was like not kind of standard to do that in the United States. So we did a number of things. And then once we were smaller, we're nimble, we don't have a lot of projects, we have this newfound sense of urgency. I told people this is our defining moment. Then I really focused on my leadership team. And I gathered like the few dozen top people in the company together and said,

I really need you guys. I need you all. Like, this is our defining moment. And everyone just rallied together. And those were just like, I mean, I could go down the list. There's like 50 things I could probably mention, but those are some of the big principles. But it was about action.

I mean, I think the other thing, if I said before, the first principle was like optimism, having the right mentality and projecting the right mentality. The other is action. And I think that like so many people, and this is the problem with people that rely too much on data, they struggle in times of change and crisis because the data is murky or they have to rely on their intuition. And they like start making pros and cons lists. These things are generally not the best decision-making framework for a crisis.

And so we were all about making fast, decisive, bold actions. And it's like, if you're on a highway and you're not sure if you should get off the exit, the worst thing you can do is kind of like, I don't know which way to go. And you hit the divider. You have to have this like intensity of decision making. And I think that's very, very hard for people. I think it's not natural. How do you maintain a beginner's mindset

when you're working at an extremely high level, you've been working at that level for quite a while. I mean, you said, you started running this unicorn at 26 years old and it's a huge company. It's a significant company. Everybody knows what Airbnb is the entire world. You do know a lot about how to do these things. You've got the scars to prove it. What is it that you do to keep yourself humble and keep yourself open minded to things you don't know because you don't know what you don't know? Yeah, it's so fascinating. I'll try to think of a good analogy. I have season tickets to Golden State Warriors, and I'm fortunate enough to sit close to the bench.

And so I got to see like, the right kind of mindset to win a championship. And I also got to watch them when they weren't winning championships. And there's some fine line where you need to have confidence, you can't be so confident that you phone it in. You start becoming complacent. You see like teams that get complacent. They think they're going to win the game. They lose. And then teams that beat themselves off and they don't have confidence, they also lose. And so there's this really interesting thing where you're like confident, but you're still a beginner. And the way I try to be still a beginner, somebody asked Steph Curry, how do you bring all to every game? And he used to say something on the free game. He says, I find the game within

every game. There's a game within every game. There's always a way to improve. I am obsessive about not doing, I don't want to just do what I've done before. I want to try to say something I've never said before. And I may not, but like, there's a goal to do something I've never done before. The goal of the company is to reach, to constantly be reaching beyond its comfort zone, to assume that you're the growing, you're dying. So I think it's about continually trying to be in this constant state of self-improvement

every minute of every hour of every day. And we're constantly in a state of reinvention. We're trying to constantly push ourselves to become better. So like, we're literally doing this right now. And maybe this is part of me just being like self-critical. And the one thing I can say, Airbnb is this noun that we've used all over the world. We do over $80 billion of sales.

Everyone knows Airbnb. Other hand, I'm like, man, we haven't really fundamentally changed who we are in 17 years. We can be doing so much more. We still have people that aren't having great trips. So I think it really comes down to like staying grounded, talking to your customers, being in the field, being in the community, and continually reaching for that ideal that is always a little bit out of grasp. I feel like we haven't made

it yet. And I hope we never quite arrive. You know, there was a study done a million years ago about kids who were in honors classes. Average students in high school actually outperform the honors kids because the honors kids are always told growing up, you're so wonderful, you're so amazing, you're so fantastic, you're so smart. And they're on a pedestal and they're very afraid of falling off because of what they've achieved.

Whereas your more average student is constantly told, good effort, keep improving, you're doing better, good effort, so they don't perceive a ceiling or a pedestal. I like that. You know, it's funny, my dad raised me like that, and I never realized at the time, but my dad never told me I was talented or smart. And he probably didn't mean a service,

he only rewarded effort. And I think there's a lot of studies about the growth mindset that if you reward a child for being intrinsically good, they're going to be afraid to try because they don't want to disprove you. that if you reward a child for being intrinsically good, they're going to be afraid to try because they don't want to disprove you. But if you reward effort, the only way to fail is to not give it your all. And I think there's something about this. Like there's a basketball coach from UCLA named John Wooden. He was the winningest basketball coach in NCAA history. And somebody once asked him, like, what is your secret to success? And

he said, the secret to success is all I asked my players to do was do their very best. And somebody asked him like, do your very best. That sounds kind of like what parents say about kids who lose. And he goes, well, here's the secret. I saw potential in people that they didn't see in themselves. And so I was always trying to get people to reach beyond their potential. I think the role of a leader is to just get everyone to do their best, but not participation trophy best. I'm talking about better than you ever think you could. If I tell somebody you could do better,

I'm not saying you're not good enough. I'm saying I see potential in you that you may not see in yourself. And I know that we can do more. And I think so much of leadership is believing. I think the biggest gift a leader can give to a person is to believe in them. And that can come in saying, you're great, you're wonderful. But I can also come to say, I believe we can do more. And it's kind of funny that some of the best coaches in history are ones that These are numerous coaches espousing the same philosophy, rewarding effort, seeing potential. I'm curious what you've learned about having to adapt your leadership style to get that push, to get that drive, or are you so public with it that it's understood before you walk in the door? I like to think that now it is,

not to overuse a military analogy, but I want people to almost think it is like the Special Forces, and so it's gonna be more difficult, but you're gonna know it it's more difficult and you can opt in or you can opt out. So I think like when we used to hire people, I think our recruiters are more like salespeople and they were basically trying to sell people on how amazing it is. And they were selling people on the experience of working here. There was this incredible job ad. Have you ever heard the Ernest Shackleton job ad? I've written about it. Oh, you have? Okay.

Men needed for hazardous journey. Yeah. Long hours, bitter cold, survival doubtful. Yes. Safe return doubtful, honor and recognition, and case of success. And I think that in some ways that's probably the most famous job ad ever. And it turned out to be a very honest representation of what the journey was. Shackleton went on a journey of the, was it the North Pole? Yeah.

South Pole. They got shipwrecked for like 13 months or something ridiculous. And the story is that no one died. The reason it worked is because he recruited the right people. He recruited people that liked insurmountable odds. That's basically my philosophy. I want to recruit people that like to do the impossible, that want to push themselves beyond their limits. I don't think this is for everyone. I don't manage the host community this way.

I don't think five million hosts want to be pushed the extent of our employees. Although I do try to hold the host to a higher standard than others websites. I just think it's really important that you're honest. And I do also think it makes a difference, Simon, that people understand your motivations. I may push people harder than they've ever been pushing their life. Sometimes they won't like that. But I think it's also important they understand where I'm coming from. And where I'm coming from is like, I want Airbnb to reach its potential. And it's only possible if you do too. And I'll never try to ask you to do something that you can't do. I might get wrong. I might overestimate what people can do. And my expectations could be unrealistic. But I do think I have not had challenges,

but I think it's those two things. It's recruiting the right kind of people, your motivations, not being Pollyanna's and selling something is unrealistic. And then the second thing is just telling people where you come from. Why am I doing this? Yeah. It's very Steve jobs, right? People talk about those days that it was so hard to work there, but the people who didn't want to be pushed didn't go work there. I got a tour from the Apple historian. He was telling me they get all these fancy engineers and folks coming in from Google and Facebook and wherever they came from that they were hiring. And they'd walk around like

that they're the bee's knees. And they would say in a meeting, do you know what I've done? And maybe they invented some famous who knows what at some other company. And invariably, somebody would look up and say, we don't care what you've done. We care what you're going to do. And it's so ingrained in the culture, this is being said years after Jobs died. It's so ingrained in the culture that you come here to be pushed. The people who want to be pushed to do the best work of their lives go work there. Otherwise, it's OK if you don't.

This is kind of the thing. People ask me about Amazon all the time. So much has been written about what a difficult culture and even the people who like it there only survive two years kind of thing. And my answer is always the same, which is they didn't lie. It's out in the open. If you kind of like that, then give it a try. And if you don't like that, then don't go there. Like, could they do better? Of course, every company can do better, but they didn't lie. And I think that's really interesting. Culture and values are really important in a company. But I think when people hear culture, they often get a very superficial sense of what culture is. It's the food, it's the yoga

classes, it's the amenities. I think culture is the unique way that you do things that distinguish you from everyone else. I think it's really important that you have a strong culture. I mean, there are such things as bad cultures, but usually there's strong cultures and weak cultures, and the weak cultures are where there isn't really a shared way of doing something. I think it's really important that like we have our way, the Arabian B way, and we're open, we're honest, and people that feel like they're part of that tribe opt in, and people that feel like it's not for them, well, the good thing is a lot of leaders aren't like me. And so if anyone's listening, like, well, I wouldn't want everyone to run their company like you, I say, well, you don't have to worry about that.

Because the point is that every person is different. Every leader comes from a different background. And I'm going to run Airbnb one way. And don't worry. Probably no one else will run it quite like that. And every leader should run it quite like that. And every leader should run it the way that is best for their company, their market, and what is most natural to them. And I think it's really important that you're open. But I think a lot of people apologize

for how they want to run their companies. They try to run their company as a midpoint between how they want to run it and how the people want to be led. And what often ends up happening is that midpoint makes nobody happy because it's a compromised way of leading. It's like all these half measures don't really appease anyone. That's a brilliant insight. I'm gonna say it again, a lot of leaders lead as a combination of the way they want to lead

and combining the way other people want to be led, versus saying, this is how I lead and attracting the people who want to be led that way. Very good insight. Yeah, and I think it's really important that people spend a lot of time asking, how do you want to lead? What's important to you? Being deeply introspective and then being clear with people and then getting their input. Like maybe some of your theories are wrong, but like really working through that and then getting everyone aligned and saying we're going this way. Because if you don't do that,

if you hire people from 10 companies, they're gonna each bring their way and you're gonna basically be the compromise of 10 different ways of doing things. I just had this conversation literally right before I got on with you, where somebody asked me the question, what do I do? I don't think my senior executives believe in the cause.

It seems like either the leader's failing to articulate some sort of higher cause that inspires, or they didn't fill to the people they should be hiring. If that's the question at this point, you know, not everybody's going to believe in Airbnb in your vision, but I hope your senior executives do. Like that's the minimum standard. The senior executives have to believe because like somebody once said, leadership is the upper bounds of how much people care. And people generally aren't gonna care more than the leaders. And if they do, that's a bad sign. The leaders have to be the standard

and they have to be the standard for passion, for belief, for why you're doing what you're doing. And if you have a team where you feel like there's a gut feel and you always can feel in your gut that the team doesn't believe in what you're doing, then you're totally right. It's probably two steps. Clearly articulate the

vision and seek total buy-in commitment. And the second part is a choice. The second part is people might not be able to totally buy in, but it's really, really important that you don't avoid, I think, those hard conversations. And if I'm honest with you, Simon, I've hired many leaders. I've hired many execs that didn't believe in what we're doing. It was a little bit of like probably on both of us. I probably at times, wasn't clear about what we're doing. You know what you know how it manifests. It's more like you're selling the person. And you're like you're trying to like convince somebody to do something, rather than

filtering like Ernest Shackleton wasn't trying to sell people to join his mission quite the opposite. Quite the opposite. And it's a weird thing as you sell people too hard, they feel sold to and they lose their sense of agency. And even if you do convince them, you might convince them to do the right thing for the wrong reasons, which is still the wrong thing. So I think it's really, really important. I think this is especially problematic for really hot companies because people could

join you for the wrong reasons, which is you're cool, you're hot, you're growing, and that might always be true, and then they won't be with you. So yeah, I think this is a really important thing. Like your values should be a filter. Like your values should be things that people disagree with. If you have values and a vision and a culture, and everyone agrees with it, it probably doesn't stand for very much. So I do think it should be a filter for the right kinds of people. The best definition of culture I ever heard was culture equals values plus behavior. Oh, I like that. And so to have a strong culture, you have to have clearly articulated values and you hold people's behavior accountable to those values and you hire to those values, etc, etc. And if you have a weak culture, it's because you either don't have values or you don't hold

people accountable to them. Yes, I think that's exactly right. And so that's kind of like the job of a leader. You asked me relationships to weightlifting. And the thing that is consistent is leadership is presence, not absence. That leadership is about enforcing the standards of quality and behaviors day after day after day after day. And eventually, yes, you can let go and you can trust people, but it's really, really important that those standards are enforced, that the values are consistent. You said Airbnb, you still see it as you haven't succeeded yet. What is the vision that is so big that you feel you still have so much work to do? When people see Airbnb, they see a marketplace for short-term rentals, for stays, but I think

that there's something so much bigger. Simon, you and I have worked on this together. We've talked about what's our why, why do we exist? I think I go back to the first weekend when Airbnb was started. Joe and I inflated three air mattresses, and we called it Air Bed and Breakfast for a design conference, three designers stayed with us. It really wasn't just about a place to stay. It was about connection.

It was about the idea that these designers can stay in our house, walk in our shoes. We can have this way of experience ever since we go like a designer. I think at some fundamental level, when Airbnb works, the reason people are emotionally connected to it is because it's really about human connection. It's about this feeling that you can go to any community

and you can feel like you can belong. You can belong anywhere. And that is the basic idea. I think that's a fundamental need that everyone has. And I think post pandemic, I think people have that need more than ever. I think people feel disconnected, they feel divided, they feel lonelier than ever.

And I think we really are seeking genuine connection. I think the most genuine connection is not gonna be on the internet. It's gonna be in the physical world face to face. How has that promise changed? Because in the early days of Airbnb, you literally stayed in someone's house. You know, sometimes they were in the other room and sometimes they had left the house for a week, but you were in their house and with their stuff. And to your point, it was a connective experience. And as the business has matured and the market has sort of matured with it, you don't really

stay into somebody's real house anymore, you know? I think it's less about connection between the guest and host temporarily. It's more group travel and family travel. The house is a vessel for people connecting as groups and our group size are getting bigger and bigger and bigger and often people want to connect with each other. But I don't think Airbnb is doing enough today currently around bringing people together. I think we're on this earth to help bring people together in communities all over the world.

And so if we are successful, if we achieve our vision, what we become is a community, not a marketplace, but a community where you can travel, you can live anywhere in the world. And one day you could wake up, you can go to a different city, and you could feel like you've been there your entire life. That would be the vision of where we want to go. One of the challenges that you don't have yet, but you will have, is succession. You've been the only CEO at the company.

We've seen it happen time and time again. Visionary CEOs who are not driven by the numbers have to replace themselves. The board tends to push the CFO or the COO CEOs who are not driven by the numbers have to replace themselves. The board tends to push the CFO or the COO to replace the CEO, which is a different skill set. And we see great companies become short-termist and myopic over and over and over again. Maybe it's too soon because you still got a few years left in you.

You're very public about rejecting the traditional ways businesses are run, that the people come first, the numbers come second. You're one of the new breeds of CEOs rejecting the old Jack Welch sort of Milton Friedman ways. You're one of the guys on the list. So I'm curious how you think about succession and if it's different than the way that it's traditionally or currently done. That's the reason for the question.

Yeah, probably. I'll make three points. The first point is, hopefully, this is a long time from now. I started this company was 26. I'm 43. I hope to be doing this through my 50s, maybe into my 60s. We'll see. So hopefully, this becomes a multi decade question, bearing good health. So bearing good health, I think I'll be doing this for decades. So hopefully this is a theoretical question

for a long time. The second point is Walt Disney. So for example, Walt Disney was a famously difficult succession plan. Walt Disney died in 1966 and the company for a while was paralyzed. They asked, what would Walt do? And it was very difficult

and the company almost got taken over. And then Michael Eisner came and he kind of helped save the company. And Bob Iger took it to the next level. But that was a really big problem. The one thing I'll say about Disney is I think that Disney has had much more staying power than Paramount or Warner Brothers or MGM. I mean, MGM is now owned by another company. And I think there's something about the longer the founder runs the company.

In a weird way, I think it's paradoxical. I think the easier it is to hand it off because the culture gets very fervent. It gets very ingrained. There becomes a really set way of doing something like so say when Steve Jobs died the Apple culture, even though they hand it over to a CEO Tim Cook is not like a really good job. It's still pretty strong. It's not quite what it is with a Steve, but it's a very, very strong culture. So I think you wanna like create a very strong

institutionalized founder culture where it's almost like muscle memory, like where you don't have to check and it's almost like you're always there, even when you're not there. And then the third thing is the actual mechanics of succession planning. And for that, yeah, I haven't gotten there yet. But I hope I

have the courage, whenever that day comes, to appoint someone that is not necessarily a complement to me. And people end up doing is they're like the visionary founder, and they get like the operator, or the finance person. And I think that can be quite risky, but that's the safe move because you know what, you know what's the awkward thing? There's a little bit of a social taboo to like work for people younger than you, unless you're the founder. So like I'm afforded the ability to hire people

older than me because I'm the founder, but there's this kind of notion, like whoever the successor is at Apple, they're not gonna give it to somebody in their forties because these people in their fifties and sixties, you know, there's gonna be this, weird dynamic where you're not a big enough company person, but that person is a little younger, who's a little more visionary might be the person with the vision, the spirit to remake the company.

And I think we're going to need to stay young, we need somebody to remake the company. So I think we're going to need somebody that like you really want somebody that's got 10 to 15 years runway, who is visionary, because I do not think the vision dies of the founder. I think if the vision dies of the founder, then you become a heritage brand. And if you're a heritage brand in technology, that's a big problem, because technology is a synonym for the word change. So that would be what I would think. I would not think that you'd want to hand it over to a grown-up safe pair of hands. And if you do, to me, that's a transitional leader.

That leader is transitioning for the visionary. The vision should not die with the founder. It must live on with somebody new, somebody probably with a long runway ahead of them. I wish more companies followed your lead. Brian, always a pleasure. I always learn something new. Thank you. Thanks for taking the time.

I really appreciate it. I love talking to you. And I look forward to seeing where B&B goes. Stay tuned. If you enjoyed this podcast and would like to hear more, please subscribe wherever you like to listen to podcasts. And if you'd like even more optimism, check out my website, simonsenic.com, for classes, videos, and more. Until then, take care of yourself, take care of each other.

A Bit of Optimism is a production of The Optimism Company. It's produced and edited by Lindsay Garbenius, David Jha, and Devin Johnson. Our executive producers are Henrietta Conrad and Greg Rudershan.