Welcome back everybody for another deep dive.
Always fun.
Today we're gonna be cracking open the world
of Brian Chesky.
Oh yeah, Airbnb guy.
The CEO of Airbnb and we've got this great YouTube interview
with him from the diary of a CEO.
It's a good one.
Yeah, this is really packed with insights so.
He goes deep.
Yeah, we're gonna pull out some of those for you guys today.
So let's just jump right in.
Okay.
His childhood honestly is really kind of fascinating
and it sheds light on so much of his journey so.
It really does.
I think you can really see the roots of Airbnb
in his early life.
Yeah.
You know, he was a sensitive kid
and he used art as an escape.
Kind of a way to deal with challenges.
Exactly.
Yeah.
Yeah, he would create these new worlds almost like.
Like he was looking to belong somewhere.
Yeah, spaces where he belonged.
Yeah, and I think that's so interesting
that yearning for connection.
Right.
For belonging, it's such a human thing.
And have you ever felt like an outsider?
Oh yeah, totally.
It's amazing how that can be a catalyst
for some pretty amazing things.
Absolutely.
And it's fascinating how his journey
eventually led him to Airbnb.
Right.
But before we get there,
let's talk about his choice to study industrial design.
That's not a typical path to tech CEO.
It's not.
But when you think about it.
There's a connection.
There is.
Industrial design focuses on, you know,
creating functional, beautiful products that solve problems
in the real world.
And it's not just aesthetics.
It's about understanding how things work,
how they impact people's lives.
Exactly.
And that's what's so interesting about Airbnb.
Right.
They're not just selling rooms.
Right.
They're selling experiences.
They're selling connections.
Yeah.
A sense of belonging.
It's that idea of, you know,
we talked about conditional love a little bit
and he talks about that in the interview.
Yeah, he's got some really interesting things
to say about that.
He says a lot of people chase success
seeking love and validation.
But that kind of love is never enough.
Like trying to fill a cup with a hole in the bottom.
Exactly.
You're constantly seeking external validation.
But it never truly satisfies that need for connection.
You would think somebody who achieved his level of success
would feel fulfilled.
You would think.
But he talks very openly about the loneliness.
Yeah.
It's really incredible how candid he is about it.
As the company grew.
Yeah.
And he was never blurring between personal and professional life.
Yeah.
And he was surrounded by people, but.
But felt isolated.
Yeah.
He says lonely leaders are probably not the best leaders.
Right.
You don't have as much resilience.
Makes you think, are we sacrificing personal connections
on the altar of success?
It's a good reminder.
It is.
To check in with ourselves.
Absolutely.
Now, you know, what was it like in those early days
of Airbnb?
Well, it's interesting because Airbnb,
it wasn't born out of some grand vision.
To disrupt the travel industry.
Right.
They just needed to pay rent.
They needed to pay rent.
So they turned their apartment into a bed and breakfast
during a design conference.
And the rest, as they say, is history.
Yeah.
So simple, born out of necessity,
turned into this global phenomenon.
Right.
It's amazing.
Yeah.
It kind of makes you realize that even the most groundbreaking
ideas, they often start small.
Yeah.
Right.
Solving a real need.
Creating something people love.
And speaking of love.
Oh, yeah.
Chesky shares this great piece of advice from Paul Graham.
Yeah.
Founder of Y Combinator.
Yeah.
Do you remember?
I remember what he said.
Yeah.
It's better to have 100 people love you than a million people
just kind of like you.
That's so good.
Isn't it?
Quality over quantity.
Yeah.
Finding your tribe the people who resonate with what
you're creating.
Don't get caught up in trying to please everyone.
But focus on creating something exceptional
for a smaller audience.
And that's what they did.
They did.
That brings us to the customer experience.
Oh, yeah.
Another key ingredient in Airbnb's success.
It often went against traditional business thinking.
Especially when it came to things like scalability and profit.
Right.
But Chesky firmly believes that you can't always
measure what matters most.
Right.
He's all about intuition and heart in business.
He even quotes Albert Einstein.
Not everything that counts can be counted.
And not everything that can be counted counts.
That's so true.
It's not just about data.
It's about trusting your gut, your instincts.
Right.
Creating something that resonates on a deeper level.
That's a powerful message.
It is.
Anyone who's ever felt pressured to prioritize the number.
Over their own feelings.
And that brings us to company culture.
Oh, yes.
Chesky's adamant that culture is the most important thing
you will ever design.
Yeah.
Because it's the engine that designs everything else.
What does that actually look like?
Right.
What are the tangible things that make it so unique?
Well, it really is about tapping into that fundamental human
need to belong.
OK.
He believes that people are inherently good.
And that we're more alike than we are different.
Powerful belief.
It is.
Especially in a world that can feel so divided sometimes.
Yeah.
But how do you actually build a company culture that
reflects those values?
Well, it starts with the leader.
He's very clear about that.
He says, your company culture is an extension
of your own values.
And the way you choose to lead.
OK.
And he's a self-proclaimed perfectionist.
OK.
Obsessed with details, simplicity,
creating a cohesive experience.
Almost like he's applying those industrial design
principles to the company itself.
Totally.
He's not just building a product.
He's crafting an entire ecosystem.
Right.
Where everything's connected and intentional.
Breaking away from traditional corporate structures.
Right.
He implemented a radical approach at Airbnb.
How so?
Well, he did away with separate divisions.
OK.
He runs a company like a giant startup.
No silos.
No bureaucracy.
Just pure creative energy flowing through the organization.
That's bull.
It is.
Especially for a company that big.
Right.
Most companies that size, they get bogged down
in layers of management.
Totally.
But it's that startup mentality that
allows them to stay agile and innovative.
Right.
And allows them to focus on the things that really matter.
You know.
Quality customer experience.
All those small details.
Yeah.
That make a big difference.
And it sounds like he's really hands
on when it comes to maintaining that focus.
He is always looking for ways to improve.
Always.
Yeah.
He uses this analogy of a gardener carefully tending
to their plants.
OK.
Constantly pruning, shaping them to ensure they flourish.
That's how he approaches company culture.
Exactly.
An ongoing process.
Always evolving.
Growing.
And that process never more important than during a time
of crisis.
Yeah.
He really believes that a crisis can actually
be a catalyst for growth.
Right.
Forcing you to confront your values.
Yeah.
Make decisions that truly reflect who you are.
Leading with your heart.
Yeah.
Making principal decisions, he calls them.
As opposed to just business decisions.
Exactly.
During the pandemic.
Yeah.
When Airbnb lost 80% of its business.
I mean, talk about a crisis.
He could have made decisions just based
on financial survival.
Right.
He could have, but he didn't.
What did he do?
He chose to prioritize his employees.
Well, he offered generous severance packages
and went above and beyond to help them find new jobs.
Wow.
He even reached out to other CEOs personally.
Oh, wow.
Asking them to consider hiring his former employees.
That's a level of compassion you don't often
see in the corporate world.
No, especially during a crisis.
Yeah.
It really speaks volumes.
It has.
About his character.
Right.
The culture he's built at Airbnb.
Yeah.
Leading with empathy, even in the face of adversity.
It's a reminder that the choices we make
in those difficult moments.
Yeah.
Define us.
They become part of our legacy, and they
shape the culture around us.
And speaking of legacy, Chesky's story
is full of valuable lessons for anyone seeking
to build a meaningful one.
Absolutely.
Whether you're an entrepreneur, a creative,
someone just navigating life.
His journey highlights the importance
of staying true to your values, embracing creativity.
Right.
Prioritizing human connection.
But it also reveals the potential pitfalls of success.
He talks about how achieving that $100 billion
valuation with Airbnb's IPO didn't bring him
that lasting happiness that he expected.
It's like he reached the top of the mountain.
Right.
Realized the view wasn't what he imagined.
His daily life hadn't really changed.
No.
Still grappling with.
Feelings of loneliness, emptiness.
Yeah.
Difficult realization.
It must have been.
How did he?
Well, he started by looking inward.
OK.
Examining his motivations and reevaluating his priorities.
He realized that he'd been so focused on building Airbnb.
Yeah.
That he neglected his personal life,
the people he cared about.
He achieved incredible external success.
But at what cost?
Right.
Wake-up call.
It was.
And he responded by making some significant changes.
Like what?
He began to prioritize his relationships,
reaching out to old friends, making a conscious effort
to stay connected.
So success is about so much more than just
reaching the top.
It is.
It's about the journey, the connections we make along the way.
Right.
The impact we have on others.
Exactly.
And I think, perhaps most importantly,
he started to think about how he could use his platform,
his influence, to make a positive impact on the world.
OK.
And his vision for Airbnb's next chapter
is a reflection of that shift in perspective.
OK.
It's about moving beyond simply providing accommodations.
OK.
And instead, creating a global community that fosters
connection.
OK.
Combat's loneliness.
That's ambitious.
It is to think that a company could actually
help combat loneliness on a global scale.
It's pretty remarkable.
It is.
But he believes it's possible.
OK.
And it's a vision that's deeply rooted in his personal values
and his own experiences with loneliness.
Right.
He's not just talking about it.
He's actively working to make it a reality.
So what does this all mean for our listener?
You know, I think Chesky's story offers a powerful reminder.
That success isn't just about what we achieve.
It's about who we become along the way.
It's about finding our purpose, nurturing our relationships.
Exactly.
Using our talents to make a positive impact.
It's about recognizing that true fulfillment comes from within.
Yeah.
The journey is just as important as the destination.
Exactly.
Yeah.
Chesky's path hasn't been without its challenges.
Of course not.
But it's a testament to the transformative power
of creativity, empathy, and the pursuit of genuine connection.
And it's a story that offers valuable insights.
Absolutely.
For all of us, regardless of our career paths, our life goals.
Right.
Now, before we wrap things up.
OK.
Let's explore one more intriguing aspect.
Oh, yeah.
Of Chesky's approach.
His unique leadership style and the unconventional decisions
that shaped Airbnb's culture.
I think people might be surprised to hear this.
Yeah.
Coming from the CEO of a $100 billion company.
So what's so unconventional about his leadership style?
He got me curious.
Well, he doesn't believe in just dictating the culture
from the top down.
It's more hands-on.
He actively shapes and nurtures the company's values
through his actions.
Leading by example.
Exactly.
Embodying the values he wants to see.
Yeah.
That's more powerful than any memo or mission statement
could ever be.
Right.
It's one thing to hear about a company's values.
Right.
It's another thing to see them actually lived out by the CEO.
Especially the CEO, yeah.
Right.
And his employees see that.
They do.
They see his passion, his dedication,
his unwavering commitment in creating a company that's
both successful and meaningful.
I can see how that would be inspiring.
It is.
And what about his decision-making?
Oh, yeah.
One of the most striking examples
is his approach to decision-making.
OK.
He believes in pulling decision-making in.
Pulling decision-making in, OK.
Rather than pushing it down.
I'm not sure what that means.
So it means he wants everyone to feel connected to the company's
core values.
OK.
And to be involved in shaping its direction.
OK.
It's not about him making all the decisions alone.
So it's collaborative.
It is.
He wants input from people at all levels.
Creates a sense of shared ownership.
Yeah.
Responsibility empowers employees.
And this was crucial during the pandemic.
Oh, absolutely.
When faced with that unprecedented crisis.
Yeah.
He didn't just retreat to a corner office
and make decisions in isolation.
He brought everyone together.
Exactly.
Like we were talking about.
Right.
Leading with empathy.
Yeah.
He rallied his team.
Yeah.
Fostered open communication.
All encouraged everybody to work together.
Exactly.
Created a sense of unity and purpose.
Reminded everyone that we're all in this together.
Mm-hmm.
And that helped Airbnb not only survive the pandemic.
But come out stronger.
Yeah.
It's really a testament to the power of collective action.
And the importance of building a company culture.
That can withstand anything.
Yeah.
Even the most challenging times.
It really is.
Ultimately, I think Chesky's story
is a reminder that leadership is not about giving orders.
It's not.
It's about inspiring and empowering others.
Creating a shared vision.
Yeah.
Fostering a culture where everyone feels valued, respected.
Connected to something larger than themselves.
Sounds like he created something special at Airbnb.
He has.
And it's something we can all learn from.
Whether we're leading a company, a team,
or just navigating our own lives.
Chesky's journey reminds us that we all
have the potential to make a difference.
Yeah.
Not just through our work, but through how we live our lives,
how we interact with others.
Absolutely.
It's about embracing our creativity, pursuing our passions.
Using our talents.
Yeah.
Creating something meaningful.
Recognizing that success isn't just about what we achieve.
Right.
But who we become along the way.
Brian Chesky said, the world needs
more creative thinkers who dare to imagine a better future
and lead with heart.
Such a great quote.
So what kind of world do you want to design?
That's the question.
Thanks for joining us for this deep dive.
We'll see you next time.