Leaders Playbook: Inside Airbnb 1/28/26

Summary

Squawk Pod – “Leaders Playbook: Inside Airbnb” (Jan 28, 2026)

Overview

This episode of “Leaders Playbook,” hosted by CNBC’s “Squawk Pod,” dives deep into the evolution of Airbnb, focusing on the leadership journey of co-founder and CEO Brian Chesky. Recorded at a luxury Airbnb listing in Beverly Hills, the episode traces Chesky's path from designer to CEO, unveiling pivotal moments that defined Airbnb—from an air mattress startup to a global hospitality disruptor. The discussion centers on leadership during crises, the power of optimism, and the unique impact of a designer’s mindset at the helm of a tech company.

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Key Discussion Points and Insights

The Origin Story and Core Beliefs (01:02–04:36)

• Beginnings in San Francisco: Brian Chesky recalls quitting his job as a designer, moving to San Francisco with $40k–$45k/year, and brainstorming startup ideas with Joe Gebbia. Lack of rent money and a sold-out design conference sparked the idea of “Air Bed & Breakfast.”
• Serendipity and Friendship: Early guests became friends, not just customers. This shaped Chesky’s core belief that “people are basically good. They could trust one another” [01:24].
• Surviving the Financial Crisis & Early Growth: Entering Y Combinator in 2009, the team found a product that filled basic needs in hard times—helping people generate income by sharing their homes. Rapid growth followed, with Airbnb becoming a billion-dollar company before “unicorn” was a common term.

Brian Chesky [01:24]: “I just maybe had this core insight that people are basically good. They could trust one another.”

Finding Leadership in Crisis (04:36–07:27)

• The ‘RIP Airbnb’ Moment: In 2011, a host’s apartment was trashed, leading to public outrage and the #RIPAirbnb hashtag. Chesky describes this as his “moment of truth,” realizing that a leader’s job is to make courageous, principled decisions—not simply follow consensus.
• Transforming a Weakness into a Strength: Airbnb introduced a $50,000 property damage guarantee (now $3 million), using trust as a company pillar.
• Philosophy of Principle-led Decision Making: Chesky acted according to values over business calculation—betting on humanity’s goodness.

Brian Chesky [05:23]: “A leader steps up in times of crisis. They’re decisive. You’re not just seeking consensus. You have to have the courage to make a defining decision that’s going to chart your way forward.”

Navigating the COVID-19 Pandemic (09:03–13:35)

• 80% Revenue Collapse: In March 2020, Airbnb lost 80% of its business in eight weeks while preparing for an IPO.
• Immediate Actions: CFO Ellie Mertz describes deploying company capital to help guests and hosts, rapidly raising cash despite a strong balance sheet, and restructuring the organization to eliminate redundancy.
• ‘Founder Mode’ Leadership: Instead of becoming hands-off, Chesky doubled down on involvement—making swift, detailed decisions, and restructuring Airbnb to function more like its startup roots.

Ellie Mertz [10:07]: “A business that had been growing at approximately 30% was effectively down 80%... we took this horrible exogenous hit to the business as a forcing function to not only move quickly, but also to figure out things that we could do to make ourselves a better company.”

“Founder Mode” vs. Micromanagement (13:35–17:58)

• Defining Founder Mode: Chesky challenges common CEO advice—arguing the founder should stay deep in the details for product and strategy, coining “Founder Mode” (Paul Graham, Y Combinator).
• Not Micromanagement, but Partnership: Drawing on a conversation with Apple’s Jony Ive, Chesky distinguishes being detail-oriented from micromanaging, focusing on “making people better,” not disempowering them.
• Efficient Decision-Making: Structures meetings to include all relevant decision-makers, reducing delay and keeping teams focused and small.

Brian Chesky [16:30]: “Jony Ive said ... Steve Jobs didn’t micromanage me. He partnered with me ... If I’m in the details with somebody, am I making them better or am I disempowering them? And I hope that when people feel like I’m involved in projects ... I am helping them push to think bigger.”

Strategy, Budgeting, and Product Development (17:58–20:32)

• Decoupling Strategy from Budget: Instead of annual, bottom-up planning, Chesky implements a two-year strategy updated every six months, separate from the annual budget. This aims for agility and continuous alignment with the product vision.
• Product Before Finance: Both Chesky and Mertz describe focusing on customer-centered product ideation before financial modeling—seeing financial planning as supporting innovation, not restricting it.

Ellie Mertz [19:57]: “We spend a lot of time thinking about ... what are we trying to design, what are we trying to offer for the customer as opposed to starting with ... what is the incremental dollar you are going to generate. That comes after.”

Scaling a Two-Sided Marketplace (20:32–22:43)

• Trust and Behavior Change: Airbnb’s challenge was changing consumer behavior at scale—convincing people to trust strangers with their homes, and guests to choose homes over hotels.
• Global, High-Stakes, Regulated: Unlike city-based network apps (Uber, DoorDash), Airbnb required global supply and handling across cultures, regulations, and monetary systems.
• Relentless Problem-Solving: Chesky emphasizes tackling problems daily and relying on great people.

Brian Chesky [21:14]: “You have to get buyers and sellers [at] the same time ... these are 2, 3, 4, $500, even $1,000 purchases. So you need a global network effect that is two-sided marketplace that’s high trust, high consideration. It’s highly regulated in a lot of markets.”

The Designer’s Mindset in Leadership (22:43–25:09)

• Optimism as Superpower: Chesky attributes much of his success to imagination, optimism, and a core faith in humanity.
• Designer’s Approach to Leadership: He sees design as deeper than aesthetics; it’s about how things work, creativity, assembling elements, and problem-solving fundamentally.
• Complementary Leadership with CFO: Mertz and Chesky’s different backgrounds (business vs. design) strengthen their teamwork.

Brian Chesky [22:43]: “I have ... a huge imagination for what’s possible ... people are basically good. They could trust one another, and we could bring people together, and people are better when they’re together.”

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Memorable Quotes with Timestamps

• On founding Airbnb:

  “It all started with an airbed.” — Brian Chesky [01:02]

• Core belief in humanity:

  “I just maybe had this core insight that people are basically good. They could trust one another.” — Brian Chesky [01:24]

• Responsibility during crisis:

  “A leader steps up in times of crisis. They’re decisive.” — Brian Chesky [05:23]

• Handling the COVID crisis:

  “A business that had been growing at approximately 30% was effectively down 80%.” — Ellie Mertz [10:07]

• On “Founder Mode”:

  “I was told to hire great people and trust them and get out of the way. I think that is terrible advice for the vast majority of founders.” — Brian Chesky [12:41]

• Partnering vs micromanaging:

  “Steve Jobs didn’t micromanage me. He partnered with me ... If I’m in the details with somebody, am I making them better or am I disempowering them?” — Brian Chesky (quoting Jony Ive) [16:30]

• On optimism and design:

  “One of my superpowers is maybe I’m just an optimist ... I have, like, a huge imagination for what’s possible in the world.” — Brian Chesky [22:43]

• Designer on the CEO path:

  “Very rarely in history have designers been given a bigger canvas than a company as big as Airbnb, and so I think I’m a bit of an experiment. What happens when a designer runs a tech company?” — Brian Chesky [25:09]

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Segment Timestamps

| Segment Topic | Key Speaker | Timestamp | |----------------------------------------------|-------------------|------------| | Intro: Airbnb origin story | Chesky, Narrator | 01:00–04:36| | Leadership amid crises | Chesky | 04:36–07:27| | Surviving the 2020 pandemic | Chesky, Mertz | 09:03–13:35| | Founder Mode, leadership style debate | Chesky | 13:35–17:58| | Approach to strategy & budgeting | Chesky, Mertz | 17:58–20:32| | Scaling trust and disruption | Chesky | 20:32–22:43| | Designer mindset, optimism & collaboration | Chesky, Mertz | 22:43–25:09|

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Conclusion

This “Leaders Playbook” episode offers a rare, candid look at the leadership philosophy and evolution of Brian Chesky and Airbnb. The discussion provides valuable insights for entrepreneurs, business leaders, and anyone interested in how design thinking and optimism can drive transformation, even in the face of crisis. Chesky's journey shows the power of principle-driven decisions, deep involvement from founders, and the value of designing both a product and a company for trust and creativity.

Transcript

[Keith Lansford]

This episode is brought to you by Schwab Market Update, an original podcast from Charles Schwab. Join host Keith Lansford for this information packed daily market Preview delivered in 10 minutes or less, including projected stock updates, monetary policy decisions and key results and statistics that may impact your trading. Download the latest episode and [e-mail] Market Update podcast or find Schwab Market Update wherever you get your podcasts.

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[Brian Chesky]

New followers though at&t business Wireless connecting changes everything.

[Narrator/Interviewer]

On this episode of Leaders Playbook.

[Brian Chesky]

It all started with an airbed.

[Narrator/Interviewer]

Inside Airbnb, the home sharing app that has forever changed the way we travel.

[Brian Chesky]

Airbnb today is now known as a noun verb all over the world.

[Narrator/Interviewer]

Meet the leader who convinced people in hundreds of countries to let total strangers see sleep in their beds.

[Brian Chesky]

I just maybe had this core insight that people are basically good. They could trust one another.

[Narrator/Interviewer]

Find out how an industrial design major turned founder and CEO runs a multi billion dollar company.

[Brian Chesky]

At that moment I realized that's what a leader is.

[Narrator/Interviewer]

Learn how the company's executives led Airbnb through one of its biggest challenges.

[Brian Chesky]

We lost 80% of our business in eight weeks. People are asking is this the end of Airbnb?

[Ellie Mertz]

Our business has effectively evaporated overnight.

[Narrator/Interviewer]

Plus how a major shift in how the CEO approached leadership helped save the company.

[Brian Chesky]

I was told to hire great people and trust them and get out of the way. I think that is terrible advice for the vast majority of founders.

[Narrator/Interviewer]

Leaders Playbook Airbnb starts now. I'm meeting up with Airbnb's co founder and CEO Brian Chesky at this estate in Beverly Hills, a five star listing. He's Airbnb. Chesky was in town to make a big announcement.

[Brian Chesky]

I am so excited.

[Narrator/Interviewer]

Launching Airbnb's super app allowing users to book more than a place to stay.

[Brian Chesky]

If you want to get makeup done for an event, if you want to hire a caterer, if you want to get a massage, you can just go to our app. You can book it. You don't need to be on a trip.

[Narrator/Interviewer]

It's one of the biggest changes he's made to the app in 17 years. I'm here to discover the leadership skills he's developed over nearly two decades as CEO. 2007. You just moved to San Francisco. Take us back to that moment.

[Brian Chesky]

Funny enough, I was living here in Los Angeles. I'm 25 years old, and I'm making like 40,000 or $45,000 a year as a designer. And one day I quit my job. I pack everything in the back of an old Honda Civic, and I drive up to San Francisco thinking I'm gonna start a tech company, but I don't know what kind of tech company I'll start.

[Narrator/Interviewer]

He moves in with Joe Gebbia, a friend he met at Rhode Island School of Design, to a modest apartment on Rauch Street.

[Brian Chesky]

My roommate Joe tells me we have one problem. He said, well, we rent check due, and the landlord raised the rent, so we don't have enough money to pay our rent. It turns out that weekend at International Design Conference was coming to San Francisco. All the hotels are sold out. And we had this idea. We said, well, what if we turned our house into a bed and breakfast for the conference? Joe inflated some air beds, and we called it Air Bed and Breakfast. Now, something unexpected happened.

[Narrator/Interviewer]

We.

[Brian Chesky]

We made enough money to pay our rent. That was probably expected. But the more unexpected thing happened is these guests came as strangers. They stayed with us for a week, and they left us friends. And I think we realize at that moment there's a bigger idea here.

[Narrator/Interviewer]

In early 2008, they bring in a friend, Nate Blajarcek, to help build a website for air bed and Breakfast. Just as people start to use the platform, the markets collapse during the financial crisis.

[Brian Chesky]

Early 2009, we enter Y Combinator, very popular startup incubator. And Paul Graham, who created Y Combinator, said, make something people want. And we realized we weren't just making something people wanted, we were making something people needed because they were losing their homes, they needed extra money. It was a perfect match for the time it was 2011. We started taking off. We became a billion dollar company back when there were so few billion dollar companies. This is like three or four years before even the term unicorn came out.

[Narrator/Interviewer]

And very quickly, Chesky has to learn how to lead a unicorn. As Airbnb's CEO, when did you start to think of yourself as a leader and not a designer, not someone who's just working on this as a side project. When did you shift into CEO mode?

[Brian Chesky]

Summer of 2011, a woman's apartment on Airbnb was trashed, and there was a crisis of confidence in the company. And we didn't at the time have any insurance or any type of protection against damage. And everyone was outraged. And they said, general users, customers. There was a hashtag on Twitter trending. What was RIP Airbnb. People thought, this is the demise of the company. And that moment, I think, was our moment of truth. And I think we stood up. I wrote an open letter to the community. I apologized to the woman who this happened to. We took a lot of responsibility, but we also came up with what was at the time a $50,000 guarantee against property damage that is now a $3 million guarantee against property damage for anything that incurs during your stay. I think suddenly a weakness turned into a strength. We took our Achilles heel and made it a strength. And at that moment, I realized that's what a leader is. A leader steps up in times of crisis. They're decisive. You're not just seeking consensus. You have to have the courage to make a defining decision that's going to chart your way forward. And that was, I think, the moment I really became a CEO.

[Narrator/Interviewer]

How did you know what to do in that situation?

[Brian Chesky]

I didn't initially know what to do. And in fact, my initial response was not to do very much and not to say very much. And the longer I waited or the more things I tried to do, the worse it got. At one point, things got so dark and so dismal that I realized, I don't know how this is going to end. And I just said, I can't make a business to decision. In other words, I can't, like, game theory out how this is going to play out. So I'm going to make a principal decision. And a principal decision is essentially, if I don't know how it's going to play out, how do I be remembered? And I just said, this is what I want to do. I mean, people thought it could bankrupt the company. They said, well, what if, like, there's all these homes that get damaged and people are claiming all these damages and want to be reimbursed, and we've made it retroactive for any damage that happened up to that point. But that was also a really courageous act because we had enough confidence to say, we fundamentally have a faith in humanity. We believe that, you know, people are basically good, that occasionally bad things happen, but they're exceedingly rare.

[Narrator/Interviewer]

By taking that risky bet on his core belief that people are basically good, Chesky managed to restore confidence in Airbnb. Over the next eight years, millions of hosts around the world join the platform, and Airbnb disrupts the hotel industry. By 2019, Airbnb is bringing in billions in revenue. Chesky and his team announced plans to go public.

[Brian Chesky]

Coming up, we lost 80% of our business in eight weeks.

[Narrator/Interviewer]

How an existential threat to Airbnb's business sparks a dramatic shift in Chesky's strategy.

[Brian Chesky]

And later, I think I'm a bit of an experiment. What happens when a designer runs a tech company?

[Narrator/Interviewer]

The pros and cons of running a company with a designer's mindset.

[Keith Lansford]

This episode is brought to you by Schwab Market Update, an original podcast from Charles Schwab. Join host Keith Lansford for this information packed daily market Preview delivered in 10 minutes or less, including projected stock updates, monetary policy decisions and key results and statistics that may impact your trading. Download the latest episode and [e-mail] Market Update podcast or find Schwab Market Update wherever you get your podcasts.

[AT&T Business Wireless Advertiser]

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[Brian Chesky]

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[Narrator/Interviewer]

By the fall of 2019, there are more than 4 million hosts on Airbnb. More than 825 million guests have rented homes. Brian Chesky and his co founders are getting ready to take Airbnb public when a global pandemic brings travel to a.

[Brian Chesky]

Screeching halt on the ides of March, March 15, 2020. That's around the time that the world shut down. We lost 80% of our business in eight weeks. People are asking, is this the end of Airbnb? And this is when we were working on our IPO and we were going to be one of the hottest IPOs in the last few years. I think it was my other defining moment as a CEO and I think we stepped up and we stared into the abyss and we realized people still want this company to exist. We're going to get in a foxhole together, thousands of us, and we're going to work our way out step by step by making bold, decisive moves. I Always think, you know, a crisis brings you clarity.

[Narrator/Interviewer]

Ellie Mertz, Airbnb's chief financial officer, helped Chesky navigate the crisis. At the time, she was Airbnb's VP of finance.

[Ellie Mertz]

A business that had been growing at approximately 30% was effectively down 80%. Brian, if nothing is amazing in a crisis. And so we took this horrible exogenous hit to the business as a forcing function to not only move quickly, but also to figure out things that we could do to make ourselves a better company.

[Narrator/Interviewer]

So what were some of those things that you did to change the company? And how do you think you changed as a leader, working with him through that?

[Ellie Mertz]

We took many actions. The first was to look at the situation of our guests and hosts. We had millions of guests and hosts who were stuck, and we had to resolve that quickly in terms of putting a huge amount of capital, of our own capital to play to try to find a happy medium for those stakeholders. We also knew immediately that we might need more cash. We had approximately $500 million of cash outflows every month. And you played that forward. And despite the strength of our balance sheet at that time, we think we had over $3 billion of liquidity. We recog that if you wanted to ensure the state of the business and that we would emerge intact, we should go out and raise cash. And we did that very, very quickly.

[Narrator/Interviewer]

That means in March of 2020, even with $3 billion in cash on hand, the company was burning through it, and the stakes were high. And at the same time, Mertz and Chesky identified other problems inside Airbnb.

[Ellie Mertz]

One of the big changes that we made to the company at that time was to change the overall structure. We recognized that we had become very diffuse, redundant from the perspective of having lots of teams working on the same things. And the crisis allowed us to reorg to a centralized model.

[Narrator/Interviewer]

For Cesky, it's a defining moment to execute their plans for restructuring. He realized he needed to get back into the details to run Airbnb like a startup rather than a large organization.

[Brian Chesky]

There's a paradox where being in the details sounds like micromanagement. It sounds like it's slowing teams down. But when you're in the details, you can actually help make decisions faster. The number of people in organizations that got to get their managers, managers, manager to manager, to approve something, but then all these leaders have to agree to something. There's a bunch of meetings. Peers can't make fast decisions. Only a leader can make a quick decision in a room. I bring everyone in the room. Everyone makes a recommendation and we can make a really, really fast decision. I think that's the key of a leader, is to make decisions.

[Narrator/Interviewer]

Chesky's leadership strategy has been called Founder Mode, a term coined by Paul Graham, the founder of startup incubator Y Combinator.

[Brian Chesky]

A year ago I went to a Y Combinator alumni event. It was supposed to be an off the record talk and they told me like, no one will ever know about this talk, so don't worry. So I kind of let loose. I talked about my journey, how I felt like I was a really good founder. But then I was CEO and I was told to hire great people and trust them and get out of the way, let them do their job. I think that is terrible advice for the vast majority of founders. Paul Graham coined Founder Mode because he said, you know, professional managers often were never founders. They weren't in the details. So it's not germane to them to be in the details. But it was always a founder's instinct to be in the details. I think the CEO should essentially be the chief product officer, if they can be, because the most important thing a company to is make a great product. To me as a designer, I just thought maybe there was a different way to design a company based on the complaints people had in large companies.

[Narrator/Interviewer]

Coming up, Founder Mode's impact on Airbnb.

[Brian Chesky]

We're gonna have as few people as.

[Narrator/Interviewer]

Possible working on things and later leading with a designer's mindset.

[Brian Chesky]

I think I'm a bit of an experiment. What happens when a designer runs a tech company?

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[Narrator/Interviewer]

What made you confident that you could do something that hadn't been done before? I have no fear of failure. Trailblazing women, changing the game One of my favorite pieces of advice Think about what your boss's boss needs.

[Ellie Mertz]

Leadership can look in many, many different forms. It really does come down to just trusting yourself.

[Narrator/Interviewer]

Life is short and you just gotta.

[Ellie Mertz]

Think big to accomplish big things.

[Narrator/Interviewer]

Julia Boorstin hosts CNBC Changemakers and Power Players New episodes every Tuesday. Wherever you get your podcasts. Despite the challenges facing Airbnb during the pandemic, Chesky and his team take the company public. On December 10, 2020, they couldn't ring the bell at the Nasdaq, so Airbnb released this video in Times Square. By market's close, the home sharing platform was worth 86% billion more than Marriott and Hilton combined. Leading Airbnb through Covid in founder mode worked. So many of the things you described, like being in the room for the decisions, having the leader be involved in all these small decisions. How is this different from micromanaging?

[Brian Chesky]

The best answer to your question was something that Jony I've explained to me. Jony I've was the head of design at Apple because Steve Jobs is notorious for being all the details. You could say he was a micromanager. And I asked Jony Ive I said do you ever feel like Steve Jobs micromanaged you because he was in every detail? And he said no, he didn't micromanage me. He partnered with me. We were working on problems together and I felt like him being the details made me better. So here's the question. If I'm in the details with somebody, am I making them better or am I disempowering them? And I hope that when people feel like I'm involved in projects and they feel like I am helping them push to think bigger.

[Narrator/Interviewer]

How do you avoid having that bottleneck decision making though and slow down the process because you can only be in so many places at once.

[Brian Chesky]

Most of what I do every week is I review projects. Anything a customer will ever see, I review every week, every two weeks, every four weeks, every eight weeks we have a robust program management function. Things come to me, I have the full chain of command in the room. So I have my direct report. Their directs, their directs, their directs. Instead of all of those being separate meetings where someone has a meeting, meeting, they elevate, they elevate, elevate. We all just kind of meet together. So first of all, that actually saves a lot of time. Everyone in the entire company is going to work on the same problem together. We're going to have as few people as possible working on things. People are going to be experts and we're going to operate this way. And it turns out that was the best thing that ever happened to the company.

[Narrator/Interviewer]

Chesky says he's focused on making a great product and thinks about financial planning differently than most CEOs. I've read that you have decoupled strategy and budget. You want your employees to focus on making the best things to serving your customers and to maybe not have the question of budget distracting from that. But in most companies, strategy and budget are hand in hand.

[Brian Chesky]

Most companies, here's what I think they do, they have an annual plan and the annual plan is usually kicked off in September. And the CFO kind of works on a forecast for the year. And then the CEO has 5, 10, 20 teams and they come back to them with plans. And the plans usually are, here's what I want to do next year, their strategy, here's what I need, my resources, my head count, the hires, the amount of, the amount of resources I need. And that rolls up to a budget. So it's essentially a bottoms up plan. So now you have 20 different plans, they're all have to be reconciled. And then you essentially approve it in like November and you kick it off in December. And now you have a 12 month plan. Here's the problem with that. On average it's a six month plan. We thought instead of having a 12 month plan, we're going to have a two year plan and we're going to update it every six months. That is a strategy. It's completely separate from a budget. Our budget is an annual plan. It's done almost entirely by the finance organization working with me. And then any incremental outperformance, like a venture capitalist is essentially invested on an ongoing basis. It's decoupled from the strategic plan. This allows us to essentially have a longer range plan that is updated more frequently. And the other thing is the plan is much more top down. Instead of trying to reconcile all these different teams going in different directions, I work with the team to create an overall plan.

[Narrator/Interviewer]

One of the more radical ideas that Brian has talked about is this idea of decoupling financial planning from product development, which seems like it'd be very challenging for you as a cfo.

[Ellie Mertz]

It's not to say that we don't have financial planning around our product development. I would say there's much more of a ideation phase before we get into the financial modeling. And that would be the, I would say, clear distinction in terms of the concept that Brian is talking about. We spend a lot of time thinking about what are we, what are we trying to design, what are we trying to offer for the, the customer as opposed to starting with the, you know, what is the incremental dollar you are going to generate. That comes after. It's, let's think about the great idea that a consumer is going to love us for and then let's build the financial model behind that.

[Narrator/Interviewer]

You convince people to open up their homes to strangers and not worry about their homes being trashed. And you convince people that instead of going to a hotel, they should stay in someone else's house or apartment with their sheets and towels and not room service and all those things people were used to. You were absolutely shifting consumer behavior. And in the early days there were a lot of naysayers.

[Brian Chesky]

I remember when I was starting Airbnb, it felt like it was easier to imagine living like this on Mars than living differently on this planet. People just could not wrap their head around any social behavior being different.

[Narrator/Interviewer]

So your challenge as a leader was to get both parts of that marketplace to scale. So how did you start off this whole process?

[Brian Chesky]

You have to get buyers and sellers the same time. Now with Airbnb, I think it is even more difficult in some ways than say Uber. If you start like Uber door dash, you got to get riders and drivers in one city. In Airbnb, you know, most people are not looking for homes in their own city. So you have to basically build this global network where you have to basically figure out what are the key destinations around the world that a, a critical mass of people want to travel to. You've got to get all that supply at once. But then it's also a very high intent purchase. These aren't like 20, $30 purchases. These are 2, 3, 4, $500 even thousand dollar purchases. So you need a global network effect that is two sided marketplace that's high trust, high consideration. It's highly regulated in a lot of markets. Handling money across borders with cultures that have often, you know, not really interacted or lived together at a scale before, so there was a lot of problems to work through.

[Narrator/Interviewer]

What was your strategy to approach each.

[Brian Chesky]

Of those challenges one foot in front of the other? You know, it's essentially every day you wake up and you just need to figure out how to get through the day. And I think a lot of it's just having really great people taking a problem, breaking down its components, working through, starting again the next day.

[Narrator/Interviewer]

You're an optimist. You believe in the goodness of people and sort of functionally an important part of the way Airbnb works. Not just the original part of the app, but all these areas you're expanding into as a leader. What do you think your superpower is?

[Brian Chesky]

That's a great question. You know, I went to design school. I remember when I was raising money, somebody said to me, I like everything about you and your idea. They really meant strangers will never trust one another, and designers don't start companies. I think there's a clue in there, and the clue is that one of I think my superpowers is maybe I'm just an optimist. I have, like, a huge imagination for what's possible in the world. And I just maybe had this core insight that people are basically good. They could trust one another, and we could bring people together, and people are better when they're together. I think the second thing is my skill set as a designer. And I think with people who are designer, they assume it means, like, the esthetic, the way something looks. I think design is so much deeper than that. Design is how something works. I think design is about imagination. It's about creativity. It's about assembling something. It's about solving a problem in a deep and fundamental way.

[Narrator/Interviewer]

Brian was told designers don't start companies. Yes, you went to business school. He did not. How do you see his designer mindset impacting the way he leads Airbnb?

[Ellie Mertz]

I think one of the reasons that we work well together is that we both didn't go to business school. We both didn't go to design school and said there's a kind of complimentary leadership style. I think about Brian's key assets around being a designer. It's about thinking many years out as to where's the world going and how can Airbnb contribute to a better world? And from my vantage point of not just the CFO role, but. But obviously being business school graduate and coming from that competency, it's saying, what is that vision? How do we prioritize our actions to make that vision a reality as opposed to merely a dream.

[Narrator/Interviewer]

It's unusual to have a founder like Brian continue to be CEO long after the company has gone public, and to have so much success. It's just a relatively unusual thing in the tech ecosystem, and that makes your role relatively unusual as well. Working with a founder CEO, what's the hardest part of your job?

[Ellie Mertz]

Hardest part is really being a productive compliment. There are often tensions in terms of different points of view, and it's really making sure that we're capturing the dream and the vision.

[Narrator/Interviewer]

Cesky and Mertz's different backgrounds and leadership skills complement each other. Their teamwork enables Cesky's instincts as a designer to power him as a CEO and for Airbnb to experiment and grow.

[Brian Chesky]

Very rarely in history have designers been given a bigger canvas than a company as big as Airbnb, and so I think I'm a bit of an experiment. What happens when a designer runs a tech company? And hopefully the conclusion is that you can build something really special, more valuable.

[Narrator/Interviewer]

Insights from some of the top business minds in the country. On the next episode of Leader's Playbook.

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