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Welcome back everybody for another deep dive.

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Always fun.

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Today we're gonna be cracking open the world

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of Brian Chesky.

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Oh yeah, Airbnb guy.

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The CEO of Airbnb and we've got this great YouTube interview

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with him from the diary of a CEO.

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It's a good one.

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Yeah, this is really packed with insights so.

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He goes deep.

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Yeah, we're gonna pull out some of those for you guys today.

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So let's just jump right in.

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Okay.

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His childhood honestly is really kind of fascinating

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and it sheds light on so much of his journey so.

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It really does.

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I think you can really see the roots of Airbnb

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in his early life.

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Yeah.

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You know, he was a sensitive kid

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and he used art as an escape.

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Kind of a way to deal with challenges.

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Exactly.

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Yeah.

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Yeah, he would create these new worlds almost like.

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Like he was looking to belong somewhere.

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Yeah, spaces where he belonged.

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Yeah, and I think that's so interesting

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that yearning for connection.

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Right.

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For belonging, it's such a human thing.

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And have you ever felt like an outsider?

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Oh yeah, totally.

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It's amazing how that can be a catalyst

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for some pretty amazing things.

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Absolutely.

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And it's fascinating how his journey

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eventually led him to Airbnb.

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Right.

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But before we get there,

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let's talk about his choice to study industrial design.

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That's not a typical path to tech CEO.

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It's not.

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But when you think about it.

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There's a connection.

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There is.

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Industrial design focuses on, you know,

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creating functional, beautiful products that solve problems

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in the real world.

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And it's not just aesthetics.

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It's about understanding how things work,

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how they impact people's lives.

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Exactly.

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And that's what's so interesting about Airbnb.

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Right.

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They're not just selling rooms.

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Right.

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They're selling experiences.

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They're selling connections.

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Yeah.

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A sense of belonging.

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It's that idea of, you know,

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we talked about conditional love a little bit

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and he talks about that in the interview.

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Yeah, he's got some really interesting things

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to say about that.

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He says a lot of people chase success

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seeking love and validation.

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But that kind of love is never enough.

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Like trying to fill a cup with a hole in the bottom.

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Exactly.

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You're constantly seeking external validation.

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But it never truly satisfies that need for connection.

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You would think somebody who achieved his level of success

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would feel fulfilled.

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You would think.

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But he talks very openly about the loneliness.

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Yeah.

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It's really incredible how candid he is about it.

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As the company grew.

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Yeah.

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And he was never blurring between personal and professional life.

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Yeah.

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And he was surrounded by people, but.

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But felt isolated.

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Yeah.

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He says lonely leaders are probably not the best leaders.

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Right.

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You don't have as much resilience.

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Makes you think, are we sacrificing personal connections

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on the altar of success?

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It's a good reminder.

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It is.

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To check in with ourselves.

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Absolutely.

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Now, you know, what was it like in those early days

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of Airbnb?

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Well, it's interesting because Airbnb,

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it wasn't born out of some grand vision.

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To disrupt the travel industry.

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Right.

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They just needed to pay rent.

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They needed to pay rent.

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So they turned their apartment into a bed and breakfast

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during a design conference.

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And the rest, as they say, is history.

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Yeah.

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So simple, born out of necessity,

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turned into this global phenomenon.

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Right.

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It's amazing.

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Yeah.

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It kind of makes you realize that even the most groundbreaking

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ideas, they often start small.

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Yeah.

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Right.

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Solving a real need.

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Creating something people love.

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And speaking of love.

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Oh, yeah.

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Chesky shares this great piece of advice from Paul Graham.

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Yeah.

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Founder of Y Combinator.

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Yeah.

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Do you remember?

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I remember what he said.

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Yeah.

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It's better to have 100 people love you than a million people

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just kind of like you.

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That's so good.

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Isn't it?

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Quality over quantity.

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Yeah.

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Finding your tribe the people who resonate with what

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you're creating.

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Don't get caught up in trying to please everyone.

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But focus on creating something exceptional

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for a smaller audience.

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And that's what they did.

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They did.

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That brings us to the customer experience.

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Oh, yeah.

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Another key ingredient in Airbnb's success.

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It often went against traditional business thinking.

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Especially when it came to things like scalability and profit.

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Right.

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But Chesky firmly believes that you can't always

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measure what matters most.

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Right.

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He's all about intuition and heart in business.

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He even quotes Albert Einstein.

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Not everything that counts can be counted.

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And not everything that can be counted counts.

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That's so true.

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It's not just about data.

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It's about trusting your gut, your instincts.

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Right.

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Creating something that resonates on a deeper level.

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That's a powerful message.

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It is.

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Anyone who's ever felt pressured to prioritize the number.

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Over their own feelings.

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And that brings us to company culture.

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Oh, yes.

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Chesky's adamant that culture is the most important thing

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you will ever design.

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Yeah.

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Because it's the engine that designs everything else.

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What does that actually look like?

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Right.

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What are the tangible things that make it so unique?

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Well, it really is about tapping into that fundamental human

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need to belong.

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OK.

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He believes that people are inherently good.

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And that we're more alike than we are different.

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Powerful belief.

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It is.

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Especially in a world that can feel so divided sometimes.

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Yeah.

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But how do you actually build a company culture that

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reflects those values?

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Well, it starts with the leader.

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He's very clear about that.

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He says, your company culture is an extension

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of your own values.

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And the way you choose to lead.

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OK.

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And he's a self-proclaimed perfectionist.

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OK.

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Obsessed with details, simplicity,

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creating a cohesive experience.

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Almost like he's applying those industrial design

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principles to the company itself.

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Totally.

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He's not just building a product.

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He's crafting an entire ecosystem.

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Right.

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Where everything's connected and intentional.

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Breaking away from traditional corporate structures.

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Right.

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He implemented a radical approach at Airbnb.

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How so?

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Well, he did away with separate divisions.

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OK.

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He runs a company like a giant startup.

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No silos.

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No bureaucracy.

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Just pure creative energy flowing through the organization.

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That's bull.

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It is.

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Especially for a company that big.

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Right.

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Most companies that size, they get bogged down

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in layers of management.

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Totally.

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But it's that startup mentality that

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allows them to stay agile and innovative.

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Right.

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And allows them to focus on the things that really matter.

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You know.

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Quality customer experience.

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All those small details.

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Yeah.

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That make a big difference.

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And it sounds like he's really hands

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on when it comes to maintaining that focus.

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He is always looking for ways to improve.

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Always.

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Yeah.

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He uses this analogy of a gardener carefully tending

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to their plants.

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OK.

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Constantly pruning, shaping them to ensure they flourish.

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That's how he approaches company culture.

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Exactly.

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An ongoing process.

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Always evolving.

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Growing.

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And that process never more important than during a time

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of crisis.

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Yeah.

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He really believes that a crisis can actually

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be a catalyst for growth.

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Right.

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Forcing you to confront your values.

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Yeah.

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Make decisions that truly reflect who you are.

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Leading with your heart.

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Yeah.

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Making principal decisions, he calls them.

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As opposed to just business decisions.

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Exactly.

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During the pandemic.

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Yeah.

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When Airbnb lost 80% of its business.

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I mean, talk about a crisis.

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He could have made decisions just based

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on financial survival.

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Right.

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He could have, but he didn't.

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What did he do?

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He chose to prioritize his employees.

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Well, he offered generous severance packages

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and went above and beyond to help them find new jobs.

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Wow.

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He even reached out to other CEOs personally.

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Oh, wow.

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Asking them to consider hiring his former employees.

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That's a level of compassion you don't often

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see in the corporate world.

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No, especially during a crisis.

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Yeah.

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It really speaks volumes.

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It has.

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About his character.

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Right.

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The culture he's built at Airbnb.

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Yeah.

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Leading with empathy, even in the face of adversity.

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It's a reminder that the choices we make

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in those difficult moments.

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Yeah.

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Define us.

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They become part of our legacy, and they

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shape the culture around us.

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And speaking of legacy, Chesky's story

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is full of valuable lessons for anyone seeking

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to build a meaningful one.

290
00:07:52,680 --> 00:07:53,240
Absolutely.

291
00:07:53,240 --> 00:07:55,840
Whether you're an entrepreneur, a creative,

292
00:07:55,840 --> 00:07:57,440
someone just navigating life.

293
00:07:57,440 --> 00:07:59,520
His journey highlights the importance

294
00:07:59,520 --> 00:08:02,680
of staying true to your values, embracing creativity.

295
00:08:02,680 --> 00:08:02,960
Right.

296
00:08:02,960 --> 00:08:04,400
Prioritizing human connection.

297
00:08:04,400 --> 00:08:07,880
But it also reveals the potential pitfalls of success.

298
00:08:07,880 --> 00:08:11,120
He talks about how achieving that $100 billion

299
00:08:11,120 --> 00:08:15,320
valuation with Airbnb's IPO didn't bring him

300
00:08:15,320 --> 00:08:17,480
that lasting happiness that he expected.

301
00:08:17,480 --> 00:08:19,280
It's like he reached the top of the mountain.

302
00:08:19,280 --> 00:08:19,720
Right.

303
00:08:19,720 --> 00:08:21,640
Realized the view wasn't what he imagined.

304
00:08:21,640 --> 00:08:23,960
His daily life hadn't really changed.

305
00:08:23,960 --> 00:08:24,320
No.

306
00:08:24,320 --> 00:08:25,320
Still grappling with.

307
00:08:25,320 --> 00:08:27,800
Feelings of loneliness, emptiness.

308
00:08:27,800 --> 00:08:29,200
Yeah.

309
00:08:29,200 --> 00:08:30,920
Difficult realization.

310
00:08:30,920 --> 00:08:32,080
It must have been.

311
00:08:32,080 --> 00:08:32,960
How did he?

312
00:08:32,960 --> 00:08:34,680
Well, he started by looking inward.

313
00:08:34,680 --> 00:08:35,200
OK.

314
00:08:35,200 --> 00:08:38,880
Examining his motivations and reevaluating his priorities.

315
00:08:38,880 --> 00:08:43,240
He realized that he'd been so focused on building Airbnb.

316
00:08:43,240 --> 00:08:44,120
Yeah.

317
00:08:44,120 --> 00:08:45,480
That he neglected his personal life,

318
00:08:45,480 --> 00:08:46,720
the people he cared about.

319
00:08:46,720 --> 00:08:49,440
He achieved incredible external success.

320
00:08:49,440 --> 00:08:50,400
But at what cost?

321
00:08:50,400 --> 00:08:50,880
Right.

322
00:08:50,880 --> 00:08:52,160
Wake-up call.

323
00:08:52,160 --> 00:08:52,640
It was.

324
00:08:52,640 --> 00:08:55,000
And he responded by making some significant changes.

325
00:08:55,000 --> 00:08:55,640
Like what?

326
00:08:55,640 --> 00:08:57,600
He began to prioritize his relationships,

327
00:08:57,600 --> 00:09:01,240
reaching out to old friends, making a conscious effort

328
00:09:01,240 --> 00:09:02,280
to stay connected.

329
00:09:02,280 --> 00:09:04,840
So success is about so much more than just

330
00:09:04,840 --> 00:09:05,720
reaching the top.

331
00:09:05,720 --> 00:09:06,160
It is.

332
00:09:06,160 --> 00:09:08,720
It's about the journey, the connections we make along the way.

333
00:09:08,720 --> 00:09:08,920
Right.

334
00:09:08,920 --> 00:09:10,480
The impact we have on others.

335
00:09:10,480 --> 00:09:11,080
Exactly.

336
00:09:11,080 --> 00:09:13,920
And I think, perhaps most importantly,

337
00:09:13,920 --> 00:09:18,280
he started to think about how he could use his platform,

338
00:09:18,280 --> 00:09:21,640
his influence, to make a positive impact on the world.

339
00:09:21,640 --> 00:09:22,640
OK.

340
00:09:22,640 --> 00:09:25,400
And his vision for Airbnb's next chapter

341
00:09:25,400 --> 00:09:27,560
is a reflection of that shift in perspective.

342
00:09:27,560 --> 00:09:28,120
OK.

343
00:09:28,120 --> 00:09:31,800
It's about moving beyond simply providing accommodations.

344
00:09:31,800 --> 00:09:32,360
OK.

345
00:09:32,360 --> 00:09:35,280
And instead, creating a global community that fosters

346
00:09:35,280 --> 00:09:35,960
connection.

347
00:09:35,960 --> 00:09:36,600
OK.

348
00:09:36,600 --> 00:09:37,960
Combat's loneliness.

349
00:09:37,960 --> 00:09:39,200
That's ambitious.

350
00:09:39,200 --> 00:09:41,040
It is to think that a company could actually

351
00:09:41,040 --> 00:09:43,280
help combat loneliness on a global scale.

352
00:09:43,280 --> 00:09:44,440
It's pretty remarkable.

353
00:09:44,440 --> 00:09:45,160
It is.

354
00:09:45,160 --> 00:09:46,520
But he believes it's possible.

355
00:09:46,520 --> 00:09:47,160
OK.

356
00:09:47,160 --> 00:09:50,560
And it's a vision that's deeply rooted in his personal values

357
00:09:50,560 --> 00:09:52,600
and his own experiences with loneliness.

358
00:09:52,600 --> 00:09:53,080
Right.

359
00:09:53,080 --> 00:09:54,160
He's not just talking about it.

360
00:09:54,160 --> 00:09:55,960
He's actively working to make it a reality.

361
00:09:55,960 --> 00:09:58,840
So what does this all mean for our listener?

362
00:09:58,840 --> 00:10:02,320
You know, I think Chesky's story offers a powerful reminder.

363
00:10:02,320 --> 00:10:05,280
That success isn't just about what we achieve.

364
00:10:05,280 --> 00:10:07,200
It's about who we become along the way.

365
00:10:07,200 --> 00:10:10,480
It's about finding our purpose, nurturing our relationships.

366
00:10:10,480 --> 00:10:10,960
Exactly.

367
00:10:10,960 --> 00:10:13,240
Using our talents to make a positive impact.

368
00:10:13,240 --> 00:10:16,680
It's about recognizing that true fulfillment comes from within.

369
00:10:16,680 --> 00:10:17,040
Yeah.

370
00:10:17,040 --> 00:10:19,680
The journey is just as important as the destination.

371
00:10:19,680 --> 00:10:20,400
Exactly.

372
00:10:20,400 --> 00:10:20,800
Yeah.

373
00:10:20,800 --> 00:10:24,000
Chesky's path hasn't been without its challenges.

374
00:10:24,000 --> 00:10:24,840
Of course not.

375
00:10:24,840 --> 00:10:27,160
But it's a testament to the transformative power

376
00:10:27,160 --> 00:10:31,840
of creativity, empathy, and the pursuit of genuine connection.

377
00:10:31,840 --> 00:10:34,360
And it's a story that offers valuable insights.

378
00:10:34,360 --> 00:10:34,920
Absolutely.

379
00:10:34,920 --> 00:10:38,760
For all of us, regardless of our career paths, our life goals.

380
00:10:38,760 --> 00:10:39,680
Right.

381
00:10:39,680 --> 00:10:41,080
Now, before we wrap things up.

382
00:10:41,080 --> 00:10:41,640
OK.

383
00:10:41,640 --> 00:10:44,000
Let's explore one more intriguing aspect.

384
00:10:44,000 --> 00:10:44,680
Oh, yeah.

385
00:10:44,680 --> 00:10:46,360
Of Chesky's approach.

386
00:10:46,360 --> 00:10:50,040
His unique leadership style and the unconventional decisions

387
00:10:50,040 --> 00:10:52,160
that shaped Airbnb's culture.

388
00:10:52,160 --> 00:10:54,000
I think people might be surprised to hear this.

389
00:10:54,000 --> 00:10:54,240
Yeah.

390
00:10:54,240 --> 00:10:57,120
Coming from the CEO of a $100 billion company.

391
00:10:57,120 --> 00:10:59,920
So what's so unconventional about his leadership style?

392
00:10:59,920 --> 00:11:01,000
He got me curious.

393
00:11:01,000 --> 00:11:04,240
Well, he doesn't believe in just dictating the culture

394
00:11:04,240 --> 00:11:05,840
from the top down.

395
00:11:05,840 --> 00:11:07,720
It's more hands-on.

396
00:11:07,720 --> 00:11:11,240
He actively shapes and nurtures the company's values

397
00:11:11,240 --> 00:11:12,480
through his actions.

398
00:11:12,480 --> 00:11:13,520
Leading by example.

399
00:11:13,520 --> 00:11:14,200
Exactly.

400
00:11:14,200 --> 00:11:16,520
Embodying the values he wants to see.

401
00:11:16,520 --> 00:11:17,000
Yeah.

402
00:11:17,000 --> 00:11:20,080
That's more powerful than any memo or mission statement

403
00:11:20,080 --> 00:11:20,960
could ever be.

404
00:11:20,960 --> 00:11:21,520
Right.

405
00:11:21,520 --> 00:11:23,640
It's one thing to hear about a company's values.

406
00:11:23,640 --> 00:11:24,240
Right.

407
00:11:24,240 --> 00:11:28,160
It's another thing to see them actually lived out by the CEO.

408
00:11:28,160 --> 00:11:29,640
Especially the CEO, yeah.

409
00:11:29,640 --> 00:11:30,040
Right.

410
00:11:30,040 --> 00:11:31,400
And his employees see that.

411
00:11:31,400 --> 00:11:32,160
They do.

412
00:11:32,160 --> 00:11:34,920
They see his passion, his dedication,

413
00:11:34,920 --> 00:11:38,240
his unwavering commitment in creating a company that's

414
00:11:38,240 --> 00:11:40,440
both successful and meaningful.

415
00:11:40,440 --> 00:11:42,280
I can see how that would be inspiring.

416
00:11:42,280 --> 00:11:43,040
It is.

417
00:11:43,040 --> 00:11:45,320
And what about his decision-making?

418
00:11:45,320 --> 00:11:46,280
Oh, yeah.

419
00:11:46,280 --> 00:11:48,640
One of the most striking examples

420
00:11:48,640 --> 00:11:50,360
is his approach to decision-making.

421
00:11:50,360 --> 00:11:51,600
OK.

422
00:11:51,600 --> 00:11:53,800
He believes in pulling decision-making in.

423
00:11:53,800 --> 00:11:56,200
Pulling decision-making in, OK.

424
00:11:56,200 --> 00:11:57,440
Rather than pushing it down.

425
00:11:57,440 --> 00:11:58,640
I'm not sure what that means.

426
00:11:58,640 --> 00:12:01,400
So it means he wants everyone to feel connected to the company's

427
00:12:01,400 --> 00:12:02,760
core values.

428
00:12:02,760 --> 00:12:03,240
OK.

429
00:12:03,240 --> 00:12:05,440
And to be involved in shaping its direction.

430
00:12:05,440 --> 00:12:05,920
OK.

431
00:12:05,920 --> 00:12:08,400
It's not about him making all the decisions alone.

432
00:12:08,400 --> 00:12:09,400
So it's collaborative.

433
00:12:09,400 --> 00:12:09,920
It is.

434
00:12:09,920 --> 00:12:12,240
He wants input from people at all levels.

435
00:12:12,240 --> 00:12:14,240
Creates a sense of shared ownership.

436
00:12:14,240 --> 00:12:14,920
Yeah.

437
00:12:14,920 --> 00:12:16,840
Responsibility empowers employees.

438
00:12:16,840 --> 00:12:19,240
And this was crucial during the pandemic.

439
00:12:19,240 --> 00:12:19,960
Oh, absolutely.

440
00:12:19,960 --> 00:12:22,120
When faced with that unprecedented crisis.

441
00:12:22,120 --> 00:12:22,880
Yeah.

442
00:12:22,880 --> 00:12:24,680
He didn't just retreat to a corner office

443
00:12:24,680 --> 00:12:26,080
and make decisions in isolation.

444
00:12:26,080 --> 00:12:27,200
He brought everyone together.

445
00:12:27,200 --> 00:12:27,680
Exactly.

446
00:12:27,680 --> 00:12:28,760
Like we were talking about.

447
00:12:28,760 --> 00:12:29,160
Right.

448
00:12:29,160 --> 00:12:30,240
Leading with empathy.

449
00:12:30,240 --> 00:12:30,480
Yeah.

450
00:12:30,480 --> 00:12:31,680
He rallied his team.

451
00:12:31,680 --> 00:12:31,920
Yeah.

452
00:12:31,920 --> 00:12:33,240
Fostered open communication.

453
00:12:33,240 --> 00:12:35,000
All encouraged everybody to work together.

454
00:12:35,000 --> 00:12:35,440
Exactly.

455
00:12:35,440 --> 00:12:37,320
Created a sense of unity and purpose.

456
00:12:37,320 --> 00:12:39,440
Reminded everyone that we're all in this together.

457
00:12:39,440 --> 00:12:40,120
Mm-hmm.

458
00:12:40,120 --> 00:12:44,080
And that helped Airbnb not only survive the pandemic.

459
00:12:44,080 --> 00:12:45,720
But come out stronger.

460
00:12:45,720 --> 00:12:46,000
Yeah.

461
00:12:46,000 --> 00:12:48,520
It's really a testament to the power of collective action.

462
00:12:48,520 --> 00:12:52,520
And the importance of building a company culture.

463
00:12:52,520 --> 00:12:53,680
That can withstand anything.

464
00:12:53,680 --> 00:12:53,920
Yeah.

465
00:12:53,920 --> 00:12:55,320
Even the most challenging times.

466
00:12:55,320 --> 00:12:55,960
It really is.

467
00:12:55,960 --> 00:12:58,840
Ultimately, I think Chesky's story

468
00:12:58,840 --> 00:13:02,400
is a reminder that leadership is not about giving orders.

469
00:13:02,400 --> 00:13:02,800
It's not.

470
00:13:02,800 --> 00:13:04,840
It's about inspiring and empowering others.

471
00:13:04,840 --> 00:13:06,280
Creating a shared vision.

472
00:13:06,280 --> 00:13:06,640
Yeah.

473
00:13:06,640 --> 00:13:10,360
Fostering a culture where everyone feels valued, respected.

474
00:13:10,360 --> 00:13:12,560
Connected to something larger than themselves.

475
00:13:12,560 --> 00:13:15,240
Sounds like he created something special at Airbnb.

476
00:13:15,240 --> 00:13:16,200
He has.

477
00:13:16,200 --> 00:13:17,880
And it's something we can all learn from.

478
00:13:17,880 --> 00:13:19,760
Whether we're leading a company, a team,

479
00:13:19,760 --> 00:13:22,480
or just navigating our own lives.

480
00:13:22,480 --> 00:13:24,520
Chesky's journey reminds us that we all

481
00:13:24,520 --> 00:13:26,800
have the potential to make a difference.

482
00:13:26,800 --> 00:13:27,520
Yeah.

483
00:13:27,520 --> 00:13:30,480
Not just through our work, but through how we live our lives,

484
00:13:30,480 --> 00:13:32,040
how we interact with others.

485
00:13:32,040 --> 00:13:32,760
Absolutely.

486
00:13:32,760 --> 00:13:36,880
It's about embracing our creativity, pursuing our passions.

487
00:13:36,880 --> 00:13:37,840
Using our talents.

488
00:13:37,840 --> 00:13:38,080
Yeah.

489
00:13:38,080 --> 00:13:39,800
Creating something meaningful.

490
00:13:39,800 --> 00:13:43,960
Recognizing that success isn't just about what we achieve.

491
00:13:43,960 --> 00:13:44,760
Right.

492
00:13:44,760 --> 00:13:46,560
But who we become along the way.

493
00:13:46,560 --> 00:13:48,800
Brian Chesky said, the world needs

494
00:13:48,800 --> 00:13:52,000
more creative thinkers who dare to imagine a better future

495
00:13:52,000 --> 00:13:53,080
and lead with heart.

496
00:13:53,080 --> 00:13:54,480
Such a great quote.

497
00:13:54,480 --> 00:13:56,120
So what kind of world do you want to design?

498
00:13:56,120 --> 00:13:57,120
That's the question.

499
00:13:57,120 --> 00:13:58,560
Thanks for joining us for this deep dive.

500
00:13:58,560 --> 00:14:25,800
We'll see you next time.