Simon SinekThe Secret Art of Micromanagement with Airbnb CEO Brian Chesky | A Bit of Optimism Podcast
EVERY SPOKEN WORD
50 min read · 10,189 words- 0:00 – 2:46
The difference between founders and CEOs
- SSSimon Sinek
What I'm trying to parse out is somebody who will use your words to justify being a micromanager and, or, or follow your advice incorrectly and become a micromanager by accident.
- BCBrian Chesky
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... I- it's certainly a pejorative. Like, it-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... it's got a negative association.
- SSSimon Sinek
Well, it doesn't feel good when it's happening to us.
- BCBrian Chesky
Potentially.
- SSSimon Sinek
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. But here's the kicker: 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.
- BCBrian Chesky
Oh, thank you so much, Simon. I mean, I think that one of the most important characteristics for a leader, there's many, but 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've 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, like, model for leadership, so everything was, like, just discovering it one foot in front of the other. And I, uh, yeah, 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 non-intuitive, and I think almost nobody is b- born a good CEO. And I think a lot of your instincts are to, like, wanna 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-
- SSSimon Sinek
Mm-hmm
- BCBrian Chesky
... to hopefully a much better CEO.
- SSSimon Sinek
S- and, and you know, you were very good about asking advice, and you're very good about getting outside points
- 2:46 – 6:46
The worst business advice Brian ever followed
- SSSimon Sinek
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, you know, a big deal in, in the business world, and if you got that advice today, you'd be like, "Absolutely not"?
- BCBrian Chesky
I think, you know, in Silicon Valley in particular, there's this whole, like, venture capital industrial complex developed around companies. When I joined Y Combinator, you know, Y Combinator's this, like, famous incubator. They give you a T-shirt, and there's these white letters on 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, they'll tell other people, will grow, and it really focuses your company on 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 down the venture capital industrial complex, what ends up happening is there's this really, like, intense focus on growth. And that, that is within reason good. Like, companies need to grow 'cause growth is like oxygen. You need momentum, and especially a company like Airbnb is a network effect. You need, you know, more people to use it for its 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, you, you've talked about, like, our, our goal is to go north. But where exactly are we going? We wanna go north. We wanna... Or, or our goal is to go 60 miles an hour.
- SSSimon Sinek
Mm.
- BCBrian Chesky
But which way? Well, I, 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 I said, "Well, where are we trying to go?" And I think that what we ended up doing in the, like, 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, I went on, Simon, like, one of the craziest 10-year runs ever in Silicon Valley. You know, the 2010s from 2010 to 2020, it... 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.
- SSSimon Sinek
Mm-hmm. Mm-hmm.
- BCBrian Chesky
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, like, focusing on making hundreds and hundreds of improvements and, 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-
- SSSimon Sinek
Mm
- BCBrian Chesky
... 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.
- SSSimon Sinek
Mm.
- BCBrian Chesky
And so I think that's the key, and so that was probably a big lesson for me.
- SSSimon Sinek
What you're basically articulating... beautifully is what it means to be customer-focused.
- BCBrian Chesky
Yes.
- SSSimon Sinek
Like, I think people overdo or sort of don't really understand what customer focus means, and it's, 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-
- BCBrian Chesky
Totally
- SSSimon Sinek
... than, you know, who- whoever else has skin in the game. And this is the great irony, like we're gonna talk about these things like they sound profound, but it's so stupid the things that we're saying, which is for a business to succeed, somebody has to buy the thing you're selling and then keep buying it. I mean, that's pretty much it. And you run an efficient business so that it's profitable.
- BCBrian Chesky
And, and, you know, it's amazing because, like, people go to business schools, and the business school has a way of, like, 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 wanna work at. It's actually very freaking simple. And everything else are constraints, they're guardrails. But I remember one- somebody once telling me,
- 6:46 – 8:29
Why numbers are not the language of business
- BCBrian Chesky
like, numbers are the language of business, and I remember thinking to myself, "No, they're not." Numbers are just the language of board meetings, and they're the 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 wanna, they wanna, they wanna buy it. And 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.
- SSSimon Sinek
[laughs]
- BCBrian Chesky
Decides to write a, a blog post about it, and he calls it Founder Mode. He basically said there's these two modes of 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 everyone 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 aren't on the battlefield with them. And the other principle is getting the entire company to row in the same direction. You know, I, if I have 1,000 people-
- SSSimon Sinek
Mm
- BCBrian Chesky
... on a, in a, I'd rather have 1,000 people in one ship than 1,000 people in a l- 1,000 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 m- 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, um, and they're trying to make the quarter or the, 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.
- SSSimon Sinek
Mm-hmm.
- 8:29 – 12:32
When to command and when not to
- SSSimon Sinek
Mm-hmm. So when you talk about f- 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? And here's where the question is coming from, which is we don't fully understand military leadership as civilians, right? We think, you know, these officers and NCOs walk around barking orders at everybody, and everybody has, you know, the, "Yes, sir. 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 questioning and asking, and they, and, and, and leaders do get input and feedback from their folks, from their troops, and they then do us- use that information to make decisions. But in chaos, in the cr- 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-
- BCBrian Chesky
Yeah
- SSSimon Sinek
... 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 do, is it, is it situational, and if so, what are those situations?
- BCBrian Chesky
I do think there's more hands-on leadership moments and more hands-off leadership moments. Let me give you an analogy. I'm a pretty bad golfer, but I've taken a couple golf lessons, and one of the worst things you can do if you learn golf is to teach yourself your own swing. And if you teach yourself your own swing, you're gonna teach the wrong swing, and then the more you golf with the wrong swing, if you do get an instructor, they're gonna ha- it's gonna take them longer to fix your swing. So 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, like, 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'd 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, so got very, very hands-on. And I said, "I'm trying to teach a standard. I want to calibrate that standard. But over time, this is gonna become muscle memory, and I won't 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, it be- and the standards become self-reinforcing. And then when I get involved now are 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-
- SSSimon Sinek
Mm-hmm
- BCBrian Chesky
... and that's what now how I can be more selective. And, like, just to, to give you a really specific example, a press release. W- 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 teamWe probably did like 70 edits of the press release. And you think that doesn't justify the few num- the, the few reporters that'll 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, edit my, like, write my quotes, do a little bit of editing because it's real muscle memory. So to me, like, just to summarize-
- SSSimon Sinek
Mm-hmm
- BCBrian Chesky
... uh, you know, rowing in the same direction, being in the details, being small, lean, being long-term, these I think are always on. And there, there, there's something in the military, General McChrystal told me, "Eyes on, hands off" which I think people think you're either hands on, eyes on, or hands off, eyes off.
- SSSimon Sinek
Mm-hmm.
- BCBrian Chesky
And General McChrystal, who actually ran j- Joint Special Operations Command, 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 th- I don't think being eyes on necessarily means you're a micromanager 'cause you're not necessarily hands-on.
- SSSimon Sinek
I wanna push a little
- 12:32 – 15:55
What is micromanagement?
- SSSimon Sinek
bit because I think so often good advice is given, of which this, uh, w- is among, that I think people misinterpret and misunderstand because I still wanna try and understand the nuance of when this becomes micromanagement. Because even, even something like eyes on, hands off feels to some people big brother-y and like you have to show me everything. I'm, I'm not gonna, you know, I'm not gonna be working on it, I'm not gonna write the press release with you, but I wanna see everything before it goes out. And I, 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.
- BCBrian Chesky
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... I- it's certainly a pejorative. Like it-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... it's got a negative association.
- SSSimon Sinek
Well, it doesn't feel good when it's happening to us.
- BCBrian Chesky
Potentially. Um, 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, kinda sees everything, and I operate under a policy of transparency, and I think the shareholders see a whole lot as well. I'm pretty transparent with my employees. So I think people are pretty eyes-on in my job-
- SSSimon Sinek
Mm
- BCBrian Chesky
... and I don't feel micromanaged. Just to give you a quick story about micromanage, um, I, I remember asking Jony Ive this question. Jony Ive was the head of design at Apple.
- SSSimon Sinek
Mm-hmm.
- BCBrian Chesky
And Steve was famously into details. I mean, Steve was, I think, one of the greatest CEOs the last 50 years. And I asked Jony 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 had 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 dis- opportunity to disagree, and often they convince me, "Oh, this is the best way to do it." But the most important thing is this creative partnership, that like, "What about this?" and, "Have you talked to them?" and, "What about these three?" And we're a functional organization, Simon. So like I want- I need to make sure engineering is talking to 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. It's not a... 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 'cause 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, "Is- 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 in standards education 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.
- SSSimon Sinek
Mm-hmm.
- BCBrian Chesky
But now we're partnering together, and I think that to me is the secret.
- 15:55 – 17:52
What bodybuilding taught Brian about leadership
- SSSimon Sinek
Has being a weightlifter made you a better executive?
- BCBrian Chesky
Absolutely. Bodybuilder, for sure. I mean, by the way, you know the old saying, you can-
- SSSimon Sinek
Bodybuilder, sorry. [laughs]
- BCBrian Chesky
Yeah, weightlifter, bodybuilder. Yeah. You know what it is? There's an old saying, like, you can't get in shape in one day, right? And so, like, if you decide one day you wanna 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, like, instill enough, like, so much trauma on your body in one moment. So bodybuilding, I mean, I, I... just as 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 felt like if I could change my body, I could change my life. I was like 16, 17 years old. This is in the '90s. 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, the consistency of one year after the other, after the other, and that you're improving, like, 0.1% every day. But if you compound 0.1% every day consistently and never quit and keep going, that you'll reach the mountaintop. And Airbnb was like a RISD project that we just never stopped. It was like the world's biggest RISD project, like that's where I went to school, and we just never stopped. And 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 and how people, how a company runs, you can potentially change an entire industry.
- SSSimon Sinek
So let's talk about that. You're, you're bodybuilding and you badly rip a muscle. Things happen.
- BCBrian Chesky
Yes.
- SSSimon Sinek
You get an injury. You, I don't know, you go skiing or something and it goes sideways, literally and figuratively. And, you know, you're not sure you'll ever be able to bodybuild again. This was COVID for you, as you said.
- BCBrian Chesky
[laughs] Yes.
- SSSimon Sinek
It was dramatic, sudden, and
- 17:52 – 21:27
How Airbnb survived COVID
- SSSimon Sinek
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.
- BCBrian Chesky
Mm.
- SSSimon Sinek
And yours, superficially, you're in the travel business. You shouldn't be sitting here right now, and, uh, 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, and then how you rebuild it.
- BCBrian Chesky
Yeah, Simon. Um, I'm-- One of our board members, this is an interesting story, is a guy named, um, Ken Chenault. He was the CEO of American Express during 9/11 and the 2008 financial crisis. And Ken Chenault told me before the pandemic, he said, "O- at least once in your career, you're gonna have to deal with a 9/11 or a 2008, and it is going to be, like, y- it's gonna be your defining moment as a leader." Andy Grove had a quote. Andy Grove was, you know, former CEO of Intel. He said, "Bad companies are 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, like, 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, "Remember that whole conversation I had with you about your defining moment as a leader, that you'll have a 9/11 or an, a 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 a crisis was myself, and 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 gonna probably make the wrong decision. I never heard anyone make a good decision out of fear, by the way.
- SSSimon Sinek
Mm.
- BCBrian Chesky
But if you can tell yourself, "This is my defining moment. Well, if it is my defining moment, how do I wanna be remembered? I wanna be remembered for being bold. I wanna be remembered for being courageous. I wanna be remembered for this being my best moment. I wanna be optimistic." I am gonna be optimistic because that mentality is what's gonna create creativity and curiosity, and it's gonna make us brave to actually handle the crisis, and I am gonna model the behavior, and I think that's ultimately what I tried to do. And, you know, um, hopefully most people felt like, you know, 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, like, you know, the world still needs Airbnb. People are asking if we're gonna exist. It's like I had to run into Airbnb, it was a burning house, we were gonna lose half the things, and 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 loved, connecting people together, making them feel like they can belong in any community in the world.
- SSSimon Sinek
That, that's, that's, that's, uh... 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. Like, and I'm very curious-
- BCBrian Chesky
Yes, you had to make a lot of hard d- hard decisions.
- SSSimon Sinek
Like, I'm so, I mean, so curious, you know, you know, h- I... What did, like,
- 21:27 – 25:42
Brian’s first actions during the pandemic
- SSSimon Sinek
what actually happened? Like, what did you actually do to keep it alive?
- BCBrian Chesky
Okay, let's go-
- SSSimon Sinek
And I love that you had the right mindset, but there were some very... Th- those courageous, bold decisions that you wanted to be remembered for, what were they?
- BCBrian Chesky
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 gonna have to make a whole bunch of decisions. I'm not gonna be able to run every decision by you." This is kinda speaking to the crisis. "So let's agree on some principles." So, um, 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 the 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, you know, all-hands meeting every week. Counterintuitively, I answered every question people asked, questions. And, uh, some of the advice was don't do team meetings 'cause 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. Like, w- 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 m- meetings, not quarterly board meetings, 'cause 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 1,000 projects and programs happening in the company, and I said, "This is gonna be the ultimate editing process. The fi- 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 the very difficult decision to lay off 25% of the employees. I tried to make sure that we weren't algorithmic in the way we cut, so I literally looked through every single person. There's no way I made the perfect decision, but I said, "I don't wanna emotionally detach from the decision. I'm gonna be as close to this decision as possible." We got rid of layers of management. You know, we took pay cuts. We did a number of things to really simplify the company. And then I think we, we handled the layoffs with quite a bit of compassion, and, and I wrote in the brightness layoff letter that got quite a bit of attention because I think we really, really went above and beyond to take care of people-
- SSSimon Sinek
Mm
- BCBrian Chesky
... um, 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 healthcare when that was, like, not kinda standard to do that in the United States. So we did a number of things and, and then, um-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.
- SSSimon Sinek
Mm-hmm.
- BCBrian Chesky
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.
- SSSimon Sinek
Mm.
- BCBrian Chesky
And, and those were just like... I mean, I could go down the list. There's like 50 things I could probably mention.
- SSSimon Sinek
Yeah, yeah.
- BCBrian Chesky
But those are some-
- SSSimon Sinek
This is great
- BCBrian Chesky
... of the big principles. But it was, it was about action. I mean, I think the other thing, if, if I said before the first principle is, like, optimism and, like, having the right, like, mentality a- and projecting the right-
- SSSimon Sinek
Right
- BCBrian Chesky
... 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, is 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 and-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... you know, you just, y- th- 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, "Uh, I don't know which way to go," and you, like, hit the divider. And it's 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.
- SSSimon Sinek
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, you know, you started running this unicorn at 26 years old, and, uh, and it's a huge company. It's a significant company. You know, everybody knows what Airbnb is, the entire world. You do know a lot about how to do these things. You've learned, you know, you've got the scars to prove it. And I'm
- 25:42 – 30:35
How to stay humble and growth-minded
- SSSimon Sinek
always curious how you, what is it that you do to s- keep yourself humble and keep yourself open-minded to things you don't know, because you don't know what you don't know?
- BCBrian Chesky
Yeah. It's so, um, it's so fascinating. I'll try to think of a good analogy. I have, um, season tickets to the 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, but 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 gonna win the game, they lose. And then teams that beat themselves up 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, like, you're still a beginner. And the way I try to be still a beginner, you know, somebody asked Steph Curry, "How do you bring all to every game?" And he used to say something I'll never forget. He says, "I find the game within every game."
- SSSimon Sinek
Mm.
- BCBrian Chesky
There's a game within every game. There's always a way to improve. I am obsessive about not doing, like I, 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, I may not, but, like, there's a goal to not do, to do something I've never done before. The goal of the company is to, like, reach, to constantly be reaching beyond its comfort zone, to, like, assume that you're either growing, you're dying. So I think it's about, like, continually, like, 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.
- SSSimon Sinek
Mm-hmm.
- BCBrian Chesky
We're trying to constantly push ourselves to become better. So, like, we're literally doing this right now. Like, and, and maybe this is part of me just being, like, self-critical. On the one hand, I could say, like, Airbnb is this noun, a verb 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 could be doing so much more. We still have people that aren't having great trips. So I, 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. I feel like I haven't made it yet. I feel like we haven't made it yet, and I hope we never quite arrive.
- SSSimon Sinek
There was a study done a million years ago, um, about kids who were in honors classes. They actually, the kids who, 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, right?
- BCBrian Chesky
Yeah.
- SSSimon Sinek
Um, because of what they've achieved. Whereas your more, your more average student, um, is constantly told, "Good effort. Keep improving. You're doing better. Good effort." So they don't perceive a ceiling or a pedestal.
- BCBrian Chesky
I like that.
- SSSimon Sinek
You know? And-
- BCBrian Chesky
Yeah, it's, 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. [laughs] And he probably did me a service. He only rewarded effort.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
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 gonna be afraid to try 'cause they don't wanna disprove you. But if you reward effort, it's easy not to, uh, you know, ef- the only way to fail is to not give it your all. And I think there's something about this. Like, th- 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, like, 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.
- SSSimon Sinek
Mm-hmm.
- BCBrian Chesky
And that can come in saying, "You're great. You're wonderful," but that can also come to say, "I believe you can do more." And it's kind of funny that some of the best coaches in history are ones that didn't even focus on winning. They just focused on doing-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... their best. And I think John Wooden, Bill Walsh, these are just, like, these are numerous coaches espousing the same philosophy.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
That, like, rewarding effort, that, like, we're seeing potential.
- SSSimon Sinek
I'm curious what you've learned about having to adapt-... your leadership style to get that push, to get that drive? Or, or is- are you so public with it that it's f- understood before you walk in the door?
- BCBrian Chesky
I like to think that now it is. Not to overuse, like, a military analogy, but I want people to almost think it is like the Special Forces. And so-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... it's gonna be more difficult, but you're gonna know it's more difficult, and you can opt in or you can opt out. So I think,
- 30:35 – 33:55
Hire according to your values
- BCBrian Chesky
like, when we used to hire people, I think our recruiters were 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. I mean, there was this incredible, um, job ad. You ever, have you ever, um... I might read it to you if you... Have you ever heard the Ernest Shackleton job ad?
- SSSimon Sinek
W- I've written about it.
- BCBrian Chesky
Oh, you have? Okay.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
Well, if I can just for the sake of your-
- SSSimon Sinek
Please, please
- BCBrian Chesky
... viewers read it out loud for a second. Um, I just-
- SSSimon Sinek
Men needed for hazardous journey.
- BCBrian Chesky
Yeah. Yes. It's-
- SSSimon Sinek
Long hours. Bitter cold
- BCBrian Chesky
Well, you basically know it.
- SSSimon Sinek
Survival doubtful.
- BCBrian Chesky
Yes, yes. Recognition. Yes, safe return doubtful. Honor and-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... recognition in case of success. And I think that, that in some ways that's probably the most famous job ad ever.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
And it turned out to be a very honest representation of what the journey was. So-
- SSSimon Sinek
Shackleton went on a journey of the, was it the North Pole?
- BCBrian Chesky
Yeah.
- SSSimon Sinek
North Pole.
- BCBrian Chesky
Yeah, and, like, he had, like, almost-
- SSSimon Sinek
And they, they got, they got shipwrecked for, like, 13 months or something ridiculous.
- BCBrian Chesky
Yeah.
- SSSimon Sinek
And the story is that no one died.
- BCBrian Chesky
Yes.
- SSSimon Sinek
Um, and, and-
- BCBrian Chesky
And he kept them all together, and yeah, that's really great culture
- SSSimon Sinek
... and it's, it's a great example because the reason it worked is because he recruited the right people. He recruited people that liked insurmountable odds.
- BCBrian Chesky
That's basically my philosophy.
- SSSimon Sinek
Yeah.
- 33:55 – 39:18
Strong cultures versus weak cultures
- SSSimon Sinek
interesting.
- BCBrian Chesky
I think culture and values are really important in a company. But I think when people hear, like, culture, they often, like, get a very superficial, um, sense of what culture is. It's the, it's the food. It's the yoga classes. It's the, kind of 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 don't know if, I mean, there are such things as bad cultures, but usually there's, like, strong cultures and weak cultures.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
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 Airbnb 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, like, a lot of leaders aren't like me. And so, like, 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."
- SSSimon Sinek
Yeah. Yeah.
- BCBrian Chesky
Because the point is that every person is different. Every leader comes from a different background. And I'm gonna run Airbnb one way, and don't worry, n- probably no one else will run it quite like that. And every leader should run it the way that is best for, like, 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 wanna run their companies. They try to f- run their company as a midpoint between how they wanna 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, like, half measures, like, don't really appease anyone.
- SSSimon Sinek
That's a brilliant insight, that a lot of leaders lead, I'm gonna say it again, a lot of leaders lead as a combination of the way they want to lead and the w- and combining the way other people want, want to be led versus saying, "This is how I lead," and attracting the people who want to be led that way.
- BCBrian Chesky
Exactly. And the problem is, like-
- SSSimon Sinek
It's a very nuanced and f- and very good insight.
- BCBrian Chesky
Yeah. And I think it's really important that, like, people, like, spend a lot of time asking, like, "Well, how do you wanna lead? What's important to you?"
- SSSimon Sinek
Yeah.
- BCBrian Chesky
Being deeply introspective, and then being clear with people and, and then getting their input. Like, maybe some of your theories are wrong, but, like, really working through that.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
And then getting everyone aligned and saying, "We're going this way." 'Cause if you don't do that, if you hire people from 10 companies, they're gonna each bring their way.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
And you're gonna basically be the compromise of 10 different ways of doing things.
- SSSimon Sinek
I just had this conversation literally right before I got on with you, where somebody asked me the question, uh, like, "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 motivate or that inspires, or they didn't filter the people they should be hiring. If that's the question-
- BCBrian Chesky
100%
- SSSimon Sinek
... at this point, you know, not everybody's gonna believe in, in Airbnb and your vision, but I hope your senior executives do. Like, that's the minimum standard.
- BCBrian Chesky
I mean, 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-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... 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-
- SSSimon Sinek
Mm
- BCBrian Chesky
... then you're totally right. It's probably t- two steps. Kind of 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 to you, Simon, I've hired many leaders. I've hired many execs that didn't believe in what we were doing, and I think 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, you know how it manifests? It's more like you're selling the person.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
And you're like, you're trying to, like, convince somebody to do something-
- SSSimon Sinek
Yeah
- BCBrian Chesky
... um, rather than filtering. Like, Ernest Shackleton wasn't trying to sell people to join his mission.
- SSSimon Sinek
Quite, quite the opposite.
- BCBrian Chesky
Quite the opposite.
- 39:18 – 41:42
A new vision for Airbnb
- SSSimon Sinek
you know, Airbnb, you still see it as, you know, you haven't succeeded yet. What is the vision that is so big that you feel you still have so much work to do?
- BCBrian Chesky
Um, you know, when people see Airbnb, they see a marketplace for short-term rentals, for stays, but I think that there's something so much bigger. And Simon, you and I have worked on this together. We've talked about, like, what's our why. Like, why do we exist? I think I go back to the first weekend when Airbnb was started, and, you know, Joe and I inflated three air mattresses, and we called it Air Bed and Breakfast for a design conference. Three designers stayed with us. And 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 could have this way of ex- they could experience San Francisco 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 could belong. You could 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, like, p- like, lonelier than ever, and I think we really are seeking genuine connection. And I think the most genuine connection is not gonna be on the internet. It's gonna be in the physical world face to face.
- SSSimon Sinek
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-
- BCBrian Chesky
Yeah
- SSSimon Sinek
... their house and with their stuff, and you, uh, to your point, it was a connective experience.
- BCBrian Chesky
Yeah.
- SSSimon Sinek
And as the business has matured and the market has sort of, uh, uh, matured with it-
- BCBrian Chesky
I think it's become less about connection
- SSSimon Sinek
You don't really stay in somebody's real house anymore, you know?
- BCBrian Chesky
I think, I think it's less about connection between the guest and host temporarily.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
I think there is more con- It's more group travel and family travel.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
So there is, uh, the house is a vessel for people connecting as groups, and our group size are getting bigger and bigger and bigger. And often people wanna 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-
- SSSimon Sinek
Mm
- BCBrian Chesky
... 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, and 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 wanna
- 41:42 – 46:44
Brian’s succession plan
- BCBrian Chesky
go.
- SSSimon Sinek
One of the challenges that you don't have yet but you will have is succession.
- BCBrian Chesky
Mm.
- SSSimon Sinek
You've been the only CEO at the company, and we've seen it happen time and time again. Uh, these great sort of visionary CEOs who are not driven by the numbers, um, 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 'cause you still got a few years left in you. You're very public about rejecting, you know, sort of the traditional ways businesses are run, that, you know, that the people come first, the numbers come second. You're in the, the, one of the new breeds of CEOs rejecting the old Jack Welch sort of Milton Friedman ways. You were 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.
- BCBrian Chesky
Yeah, probably, um, I'll just... Yeah, I'll, I'll, I'll make three points. The first point is hopefully this is a long time from now. I'm- started this company when I 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, and the only reason I probably, um, you know, uh, 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, you know, 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, and it was, uh, 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, um, by another company. And I think there's something about the longer the founder runs the company, the... In a weird way, I, I think this is 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, who's done a pretty good job, like a really good job, it's, it's still pretty strong. It's not quite what it is with, uh, 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, let's think the actual mechanics of, um, of, of succession planning. And for that, uh, yeah, who... I, I haven't gotten there yet. But, um, I-
- SSSimon Sinek
[laughs] I was just curious-
- BCBrian Chesky
I think-
- SSSimon Sinek
... 'cause-
- BCBrian Chesky
Yeah, I-
- SSSimon Sinek
... because you do think differently.
- BCBrian Chesky
I do think people... I hope I have the, like, courage whenever that day comes to appoint someone that is not necessarily a complement to me. What, 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 b- but that's the safe move. Because you know what, you know what's the awkward thing? People generally, like, 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 'cause 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 40s because these people in their 50s and 60s. You know, there's gonna be this like weird dynamic where you're not a big enough company person. But that person who's a little younger, who's a little more visionary might be the person with the vision and the spirit to remake the company, and I think we're gonna need to stay young. We're gonna need somebody to remake the company. So I think we're gonna need somebody that, like, you really want somebody that's got 10 to 15 years runway who is visionary 'cause I, I, I do not think the, the vision dies with the founder. I, I think if the vision dies with the founder, then you become a heritage brand. And you, if you're a heritage brand in technology, that's a big problem 'cause technology is a synonym for the word change.
- SSSimon Sinek
Yeah.
- BCBrian Chesky
So that would be what I would think. I would not think that you'd wanna hand it over to, like, a, like, grown-up, you know, 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.
- SSSimon Sinek
Well, I wish more companies followed your lead. Brian, always a pleasure. I always learn something new.
- BCBrian Chesky
Well, thank you.
- SSSimon Sinek
Thank you. Thanks for taking the time. I really appreciate it.
- BCBrian Chesky
I love talking to you.
- SSSimon Sinek
And I look forward to seeing where Airbnb goes.
- BCBrian Chesky
Well, g- stay tuned. [laughs]
- SSSimon Sinek
[laughs] 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, simonsinek.com, for classes, videos, and more. Until then, take care of yourself, take care of each other.
Episode duration: 46:45
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