Brian Chesky ON: The Crisis of Disconnection and Loneliness & How to Tap Into Your Creative Potential

Episode Transcript
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Speaker 1 (00:00):
He said something to me. He said, Brian, do you
know what the number one kill in America is?

Speaker 2 (00:03):
I don't know.

Speaker 1 (00:03):
Is that like heart disease is a cancer? And he goes, No,
the number one kill in America is loneliness.

Speaker 3 (00:07):
Airbnb CEO.

Speaker 2 (00:09):
His name is Brian Cheskey. He's a badass in this business.

Speaker 1 (00:12):
You're worth thirty billion dollars. The problem with success is
at tends to amplify things. No one ever told me
how lonely you would get. It's almost like I had
to go on this entire journey to realize I had
everything I needed before I even started the journey. If
I die, well I die. Brian Cheskey or the Airbnb
guy just died.

Speaker 3 (00:27):
This is, without doubt, the most unique episode of On
Purpose I think we've ever heard. Before we jump into
this episode, i'd like to invite you to join this
community to hear more interviews that will help you become happier, healthier,
and more healed. All I want you to do is
click on the subscribe button. I love your support. It's
incredible to see all your comments and we're just getting started.

(00:49):
I can't wait to go on this journey with you.
Thank you so much for subscribing. It means the world to.

Speaker 2 (00:53):
Me, the best selling author in the most the number
one healthy well innes.

Speaker 3 (00:57):
Podcast and Purpose with Jay Shetty. Hey everyone, welcome back
to On Purpose, the number one health and wellness podcast
in the world. Thanks to each and every one of
you that come back every week to become happier, healthier
and more healed. And you know that's my goal here
to create a community where we can all come together
feel connected by ideas and visions and thoughts that help

(01:21):
us in our daily lives. And today's guest is someone
who's achieved incredible success, but also someone who I believe
is carrying ideas and insights that can be really useful
to us on our journey to whatever success may mean
to you. I'm talking about the one and only Brian Chesky,
who's the co founder and chief executive officer of Airbnb.

(01:42):
In two thousand and seven, Brian and Joe Gerbia became
Airbnb's first hosts. Since then, Brian has overseen Airbnb's growth
to become a community of over four million hosts who
have welcomed more than one billion guests across two hundred
plus countries and regions. Brian is a signatory to the
Giving Pledge and is committed to donating the net proceeds

(02:03):
of a CEO equity compensation to community, philanthropic and charitable causes,
something that I'm so passionate about and so excited to
dive into. Brian, Welcome to on Purpose.

Speaker 1 (02:14):
Well, thank you, really excited to be here. It's awesome.

Speaker 3 (02:17):
I'm truly honored. I think there's very few. As I
was just saying to you offline, and I want to
repeat what I said. I think it's hard to build
something that matters. It's hard to scale something that matters,
and it's hard to build and scale something that matters
and keep making it matter. And you seem to be
doing all those things.

Speaker 2 (02:36):
We try every day.

Speaker 3 (02:37):
Congratulations, It's been a joy watching it from AFAR, and
I'm excited to build this relationship with you.

Speaker 2 (02:42):
I'm excited to talk about this.

Speaker 3 (02:43):
Yeah, well, let's dive into it. I want to start
off with my first question, which is what makes you
happy today and how does it differ from what made
you happy sixteen years ago.

Speaker 1 (02:55):
I think that I'll start with what I thought would
make me happy, and I'll tell you what does make
me happy?

Speaker 2 (03:01):
And how they're different.

Speaker 1 (03:02):
When I started this company, like fifteen years ago, i
started my co founders, I was totally broke. I had
no status, had no power, no money, nothing, And I
felt like what would make me happy was climbing a
mountain and becoming incredibly successful. And the challenge is that, well,
what do you do when you get the top of

(03:22):
the mountain. You've achieved it. And what I've realized is
that at this point, like I'm forty one years old
and a lot of people ask me like, why don't
you just retire, like or why don't you do it
all over again? And for me, I would tell them
because the fund is just starting. But the fund of

(03:43):
just starting isn't to like get the next billion people.
I kind of think of myself maybe more than a
business person. You know, you're you're kind of who you
are growing up. And I was a designer growing up,
and I kind of think of Airbnb as like one
of the world. It's the biggest canvas. Almost never has

(04:04):
a designer been given so much responsibility, so much opportunity.
And what I love is, you know, like a musician
wants to play music, a painter wants to paint a
builder wants to build, a climber wants to climb, and
as an entrepreneur, I want to create and connect things
and try to like defy the notion of what a

(04:27):
business person could be or what a designer could be
because I never met someone like me growing up. And
I'm not saying anyone's going to try to be like me.
But if I can remind people that there's leadership comes
in many different paces, many different flavors, and that a
creative person, you know, can run a company, and it
can run a really big company, a Fortune five hundred company,

(04:49):
then that's that's the very beginning. And I feel like
what makes me happy now is working with people I love.
Like the one of the great things about say success
is you can choose the people you strosd up with,
and I get to like work every single day with
people I love on ideas that I'm obsessed over, and

(05:11):
I'm just so obsessed. I think my motivation has changed.
I think when I started with my motivation was about
myself becoming something, and once you achieve that, your motivation
often turn turns outward. It's about its starting to be
about giving to other people, to lending them experience a
small part of what I was able to experience, and

(05:33):
it becomes just about the work. See, when you're not successful,
you get validation when people praise you, but eventually like
you do it for yourself, that you're not doing it
for status or success, because at some point you've gotten
all that, Like how much more is going to make
you happy? And so just doing things I love the
people I care about, That's what makes me happy today.

Speaker 3 (05:54):
That's beautiful. That's I can see that it's true for
you too. I can see that it's real for you
as you're saying it, which is such a special place
to be. And it was interesting when you were talking
about this idea of climbing a mountain. I've often thought
that there's one journey in life that we take that's
upwards up a mountain, and then there's another journey we

(06:17):
all have to take that's inwards to the valley. And
that's a journey that not everyone gets to take or
everyone thinks about taking, because we're so busy trying to
get up that we don't often get to go in right.
And it sounds like you've been excavating that internal part
for some time.

Speaker 1 (06:34):
You can learn a lot about yourself through this journey,
And you're right, the biggest journey I've probably embarked on
is the one inside of myself. The brightest days of
my life and the darkest days of my life have
been in the last fifteen years. The highs are incredibly high,
the lows can be incredibly low. The amount of stress

(06:55):
can be unrelenting, the rewards are like hard to even
grap with. When you go on a journey like this,
you learn a lot about yourself and you start to
also learn, like what's important to you starting a company,
you know, one of my first investors said Brian, Starting
companies like jumping off a cliff and assembling the airplane
in the way down. Maybe another way of saying it

(07:18):
is like playing a video game, and it's like a
thousand levels, and each level gets harder. In each level,
you learn something about yourself, you do something that's uncomfortable.
In each step of the game, you learn something. And
the problem with success is that tend to amplify things.
I mean that can be good, but it all still
can amplify holes you have in yourself. People that are

(07:40):
a little bit paranoid get very paranoid. People that are
a little deceitful become like completely fraudulent liars. People that
are a little narcissistic become like egomaniacs and stuff. And
so this stuff can tend to amplify tendencies inside of yourself.
And so if you're afraid of conflict, that's going to
actually manifest in life, like not actually dealing with things

(08:02):
if you can't, if you're not decisive, there's going to
be an element of bureaucracy. If you're like get overwhelmed
and you get paralyzed, there's going to be an action
in the company. And so you learn so much about yourself.
And I through this process, I probably learned more about
myself than I even have about business. And it's been
an incredible journey. And yeah, it's like incredible lessons. And

(08:25):
the company is like a mirror about you, right Like
when you see a company, it's like walking your house.
And by walking your house, I can step a little
bit in your mind. Because the house you bought, the
house you furnished, the house, you made a thousand decisions
and it would take a while for me in conversation
to understand you. But I walk in this house and
I can understand the thousand decisions you made. A company

(08:47):
is like that, but it's like one hundred thousand decisions
or a million decisions. And so by seeing the company,
you can like see into the person's mind everything they do,
and not even in everything they do, but everyone they
surround this self with and the culture they create and
what they And that's the thing that's so crazy.

Speaker 3 (09:03):
I'm intrigued. You said something there that really stood out
to me. You said that the happiest thing and the
best thing about being successful is that you get to
choose the people you worked with. You obviously built this
with friends, Yeah, and that's how it started. It started
in a place of being around people you love with
What was the biggest point of challenge in building something

(09:24):
with people you love as you grow it, and what
is it that you experienced and what was the biggest
lesson that you took away that actually kept it going?
Because I can imagine as you're describing highs and lows,
all of this change for sixteen years, but here you
are still building it together.

Speaker 1 (09:40):
Think about how many stories you heard of founders. It's
like a band. They come together and then eventually the
band breaks up and people don't stay together, they resent
each other, maybe things end very ugly. It's like a band,
except like it's become so much bigger than the band
because it's not just the three of you. Imagine a
band that starts three people and ends as three thousand people.

(10:03):
And that amount of pressure, the amount of spotlight, the
money that changes in like people's status and positioning, it
can do a lot to break people up. But also
unlike a band, where maybe I'm not to say, you
just have to agree on like where you perform and
what you sing. With a company, you have to agree
on like who we're gonna hire, what we're gonna call,
what markets we're going to go into, what's the prioritization,

(10:23):
Like who we're gonna raise money for. I can go
down the list of like the thousands of things you
have to agree to, And with Joe, Nate and I,
I often say it's really good to start a company
with friends. Not everyone has friends to start a company with,
but you want that reservoir of goodwill. And we made
a decision. The decision was that no one decision is
going to supersede our friendship in our relationship, that we're

(10:45):
never going to have well, debate will argue, but will
never allow a situation where winning an argument is the
most important thing. Because you think about a company as
one hundred thousand decisions, it could also be one hundred
thousand arguments. And if you get stuck the first debate,
or you like somebody won a debate, okay, great, you
have ninety nine, nine hundred and ninety nine more things

(11:07):
to discuss. And so the lesson I learned is, I mean,
first of all, Jay, I was lucky, and a lot
of people when I say I was lucky, they think, oh,
you're at the right place, the right time, with the
right idea. And I said, well maybe, but there's something
I was much luckier about. And what I was most
lucky about, what made me most fortunate was I met
Joe and Nate that we have this unbelievable chemistry. One

(11:28):
time we had to do like some personality tests. It's
like one of those core wheels, and we took this
personality test to see about our chemistry, and they plotted
our personalities and they formed a perfect equal adible triangle.
Not always you're going to find people that are perfect
compliments to you. I'd say a couple of things. Number One,
you want to have a team with people that you

(11:51):
are friends with or could see yourself becoming friends with
that you have a deep love and respect for that.
You're going to probably spend more time with your co
founders than your spouse or family if it goes well.
If it doesn't go well, then maybe not. But that's
the best case scenario that people that shared values. Because
you can debate anything so long as you're trying to
climb the same mountain in the same volee system. You

(12:11):
have different values, Eventually there's going to become irreconcilable conflicts,
but you probably also want complimentary skills. The worst case
is people with different values and same skills. Right, we
do the same job, we step in each other's tolls,
and we're trying to go in a different direction, And
so I think, and then I think. The final thing
is just this mutual love and respect and never losing sight.

Speaker 2 (12:32):
You know.

Speaker 1 (12:32):
One of the things I tried to make sure of
is like even as CEO, I wanted to try to
make sure that like Joe and Nate, you know, were
included in things. And I wanted to always make sure
that people referred to us together we thought of us
as a as a unit. When I like when public
you write a founder's letter and a lot of people
write letter and they just signed the name of the CEO.

(12:53):
I made sure that it was from all of us
and was representing all of us. I feel like they
are the heart and the soul of the company. And
it's like you know, parents, like you know, not every
child has the fortune to have multiple parents, not every
company has the fortune have multiple founders. But if they're
together and they're not fighting, they have a mutual love
and respect from another, that's going to permeate the company,

(13:14):
just like it permeates the health of a child. And
joan A and I kind of thought ourselves as parents
in the company. As a child, I'd never have had kids,
but you know there's something about that, and I think
who you are and that relationship permeates every single thing.
If the founders fight, the employees fight, if they have
respect from one another, that is going to be a

(13:34):
role a model that other people throughout the organization are
going to copy. And that's what I've learned from that.

Speaker 2 (13:39):
I think.

Speaker 3 (13:39):
I think what you're saying is very, very true, and
it's remarkable that you've been able to hold on to that.
I mean, I remember just comparing it to something very minuscule,
But I think a lot of people will be able
to relate to It's like I think with your bros
at college or at school, you'd always be like, we're
not going to fight over girls, We're not going to
fight over women. And then they'd always be the guy
who trades the friendship for a girl and then the

(14:00):
whole thing.

Speaker 1 (14:00):
And that's a short term decision. And I understand why
people make short term decisions. They make trade offs. They
want to win. But as long as you think about
the arc of your life and that life is only
like who you're with, and that you don't want to
be alone at the end of your life, and you
certainly don't want be alone the end of the journey.
If I'm climate malan, I want friends by my side
that can provide supplies at me. And like, you know,

(14:22):
like being the only one in power is actually quite lonely.
Having been in that little bit of that position, I've
now could tell people that you want to share it,
because otherwise it's incredibly isolating and lonely. And you know,
like if you get all the credit, you could also
get all the blame and it can be very difficult.
And so be able to share that with Joe and
Nate and now to be able to share that with

(14:42):
the people that I get to pick to surround myself
with that, I mean, that is one of the most
fulfilling things. And you know, great relationships get better with age,
and they give you energy, they make you better. They
hold your negative tendencies in check, and they pull out
like creative ambitions in you. They see potential in you
that maybe you don't see in yourself. I had never

(15:04):
imagined that I could be CEO of any company.

Speaker 2 (15:08):
I didn't think it'd be.

Speaker 1 (15:09):
CEO of a pizza shop, let alone be SA like
a giant fortune five hundred company to do over sixty
billion dollars last year in bookings, Like that's completely crazy.
And I've learned a lot of lessons from this journey.
One is I think we all were born with like
unknown potential. And I think the other thing is sometimes

(15:31):
the best people in your life will be people who
see potential in you that you didn't see in yourself.
And I often wonder, like, why did Joe and Ny
even agree to like, let me be the CEO. Why
did Joe tell me one day in two thousand and
seven to pack everything in the back of old Honda
Civic and drive up to San Francisco? Why did he

(15:53):
think that was a good idea? And years later he's
told me, and he told me that we went to
college together at Risdy and he saw something in me.
And it's possible he saw something in me that I
didn't even yet see in myself. And this is like
the hero's journey. Somebody might believe in you, they might
see something in you. And that's what I got with Joanna,

(16:15):
and I think I believed in what I think I saw.
They saw potentially me what I saw maybe was potential
in this idea that if people could experience what we
experienced that first weekend when we host three guests, that
this would be an idea that would spread around the world.

(16:35):
I think we have an easier time imagining living like
this on Mars and living differently on this planet. But
which of those two do you think is more likely
to happen in the near term. It's really hard for
us to imagine sch sociological changes. We can all imagine
technological changes. We can imagine things getting bigger, faster. But
it's hard to imagine us living differently. And I don't
think that we were visionaries per se. I think we

(16:59):
were expedition and I think we discovered something. One of
my first investors, Paul Graham, he said, what do you know?
What unique knowledge do you know that has allowed you
afforded you the ability to start this company that no
one else has? What do you know that no one
else understands? And I think that we discovered something. We
discovered that, like, people are fundamentally good. You know, you

(17:23):
read the newspaper, I think Chief Justice Earl Warren said,
I don't turn to the front page of the newspaper.
It's filled with man's failures. I go to the sports page.
It's filled with man's successes. I think we live in
an abundance of data reinforcing that people aren't good. And
we have probably as much data as almost anyone because
in the last fifteen years, one and a half billion

(17:47):
people have used Airvonba one and a half billion guest
arrivals in nearly every country in the world, more countries,
I think than Coca Cola. Nearly the population of Vallet
every night living together and it's only reinforced what I
think we naively believed in the beginning, these two simple
ideas that people are basically good, they're ninety nine percent

(18:09):
the same. I think that Joe and Nate believed in
me and my potential to be this company. I think
we collectively believed in the potential each other. And I
think also that this idea would be one that could
spread around the world if only we could figure out
how to communicate it to people.

Speaker 3 (18:26):
How special I mean, that's that is something that I
definitely got a mini version experience of. I just finished
forty City World Tour really for my second book, and
we probably met about one hundred thousand people on the
way oh my events, and much much smaller than the
one billion bookings. But I would agree with those two

(18:48):
sentiments so strongly. There were nine nine percent the same
and people are overall good.

Speaker 1 (18:55):
If people believed everyone was basically the same, then how
could you hate someone else because they hate someone else
is to hate yourself. And I think that we spend
a lot of energy in society celebrating the point one
percent that makes us different. I think there's a good
part of that. We call that diversity and heritage and culture.
But there's a dark side of believing that we're like
all very different, and that's that we believe that people

(19:16):
are the other and that therefore it's harder to have
empathy with somebody who isn't us. And I think that
the best way to understand that somebody is similar to
you is to walk in their shoes and to like
just you know, there's an old saying it's hard to
hate someone up close, And I think there's something weird
that's happening. We're the more digitally connected we seem to
get the more the less physically connected we sometimes get,

(19:38):
And I wonder if that has a way of like
confusing us about people that we might argue about on
the internet. No one else, no one's ever changed the
most mind YouTube comment section. But if it's hard to
live with somebody or to walk in the shoes and
not change your mind, how could you not change your
mind about something? Because that would suggest that like you've

(19:58):
experienced all of life up to that point, and that
you feel your opinions are fully formed, and that no
new data could ever change your mind about anything.

Speaker 2 (20:05):
How could that pass?

Speaker 1 (20:06):
How do you even have your pins in the first
place based on probably experiences, and so how could you've
not change your experience your opinion by new experiences with
new people. And that's kind of the kind of the
simple way we think about it.

Speaker 3 (20:19):
Yeah, I'm so glad you raised this idea of you
talked about the incredible friendship that you have with your
co founders, but at the same time you brought up
this idea of loneliness, and you said, you never want
to be lonely at the end of a journey. You
never want to be lonely at the end of building
something big. And I think in the world today we
are seeing loneliness proliferate. And it's the loneliness of not

(20:39):
that we're not around people. It's not loneliness that we're
not surrounded by people. It's that we're surrounded by people,
but we don't feel understood, we don't feel seen, we
don't feel heard, that we feel that we have to
be someone apart from ourselves, even around the people that
we're closest to. And so the idea of loneliness is
expanding away. People are feeling disconnect from each other. Yeah,

(21:01):
you're talking about sixteen years ago, you and a bunch
of friends feeling so close to each other. When have
you felt lonely in your life? And what have been
your next thoughts and steps that you've taken from that point.

Speaker 1 (21:16):
I think loneliness, which is like the darkness or the
absence of connection and love and connection, have in hindsight,
been some of the driving forces in my entire life.
If I were to think about my journey with loneliness,
I think I grew up as a little bit of

(21:37):
a lonely isolated kid. I was interested in art and design,
but I also played sports. I didn't really feel like
I fit in growing up. I kind of felt like
an outsider. I went to the Red Island School Design,
where a lot of people who felt that way would
come together be even at Risdy, I didn't feel like I.

Speaker 2 (21:56):
Fit in there, even as a hockey player.

Speaker 1 (21:58):
Even as a hockey player, to arts like kind of
like I went to like a military like private school,
and then I went to an art college, and like
I kind of had a foot in each and not
fully like like and I would I had, you know,
maybe issues of authority.

Speaker 2 (22:13):
I didn't really fit in.

Speaker 1 (22:15):
It turned out to be a huge benefit to being
a tech founder, but of course, who doesn't want to
fit in it? Growing up, like so much of our
desire is to belong, because I think to belong is
a deeply human trait.

Speaker 2 (22:28):
You know, we're tribal.

Speaker 1 (22:29):
We grew up to be in tribes of like fifty
one hundred hundred fifty people, and to not be part
of the tribe and not belong in a prior era
would be a death sentence. And I think that ultimately
today we're probably living in one of the loneliest times
in human history. If people were as lonely in yesteryear
as they are today, they'd probably perish because, like you
just couldn't survive without your tribe. And I think that,

(22:51):
you know, for me, I didn't realize that this was
a thing that I've been I was fighting throughout my life,
and so when I was twenty five twenty six, I
started with my two co founders and we became the family.
We became a family they hadn't had for ten years
since I really ten years since I left the house.
And then suddenly we were a family, the three of us,

(23:12):
and we're just hanging out together. We lived together. We
all like waked up, woke up around the same time
around eight am. We'd work till midnight, and then we'd
do it the whole the next day. We'd go grocery
shopping together, we'd like go to the gym together. Was
very communal. Then we hired people that were basically our friends.
We wouldn't hire anyone we didn't like. And then we
didn't have a lot of work life like boundaries. Everyone
was young, we didn't have families. We'd go out, like

(23:35):
drinking together and hang out together and dinner, and that
became like a family. It became like a community, and
that was incredible, and it was this deep, rich connection
and those were some of the closest friendships I ever had.
But then something happens. We go on a rocket ship,
and then I go from being a founder to a CEO.
And I was one of three founders, and then it

(23:56):
became one CEO, a silent, an individual role. And as
it became a CEO, I started leading from the front
at the top of the mountain. But then you know,
the higher you get to the peak, the fewer the
people there are with you. And no one ever told
me how lonely you would get. And I wasn't prepared
for that, and I had this guilt about not working

(24:19):
because so much of my life was about being successful.
Probably probably if I were to dig deep, because I
thought that would make people love me, and that was
probably adulation, but I probably didn't know it back then,
and I probably thought that by being successful, I'd feel
really different. And I remember I got to this point
where I was already feeling pretty isolated, and then the
pandemic happened, and I'm living by myself in a house

(24:43):
and I'm find myself on zooms twenty four to seven,
like sixteen eighteen hours a day for an entire year
of twenty twenty. I, you know, help with the team.
We navigate out of a crisis. People were predicting we'd
like some people were that we would go out of business.
We stared into the byss and we got in a foxhoul.

(25:03):
We turned the company around. We took it public in
the day of our IPO. We reached one hundred billion
dollar valuation. And remember if you told me, like a
million dollars is more money I ever imagined growing up.
My parents are social workers. It was like an unfathomab
amount of money. And I remember, after going public, is like,

(25:23):
oh my god, there's this amazing exultation. It was amazing,
like I'd gotten to them. I mount, and then I
wake up the next day and my life is exactly
the same.

Speaker 2 (25:31):
I'm alone.

Speaker 1 (25:32):
I wake up, I put on sweatpants, I go on
to iMac, and I have like ten twelve hours of
zoom meetings, and I just don't really have much of
my life outside of work. My work was my life.
And then I remember having a fortieth birthday party and
I had to make a list of people to invite.
And never in my life have I tried to like

(25:53):
make a list to who my friends are. But when
you have to make invitations, you have to make a list.
And I made a long list of people, and then
I kind of went down the list and I said,
when's the last time I talked to these people? And
I realized that almost every single person in the list,
if I were to ping, i'd have to catch them
up in my life. I couldn't just dive into something
because I had not maintained those relationships. And it was

(26:16):
just something that like started, you know, and I started
noticing I started feeling more isolated. I would have more
negative ruminations and stuff, and I didn't know at the
time that I was isolated lonely. I knew it was isolated,
but I didn't know that that also meant loneliness. And
I thought, I have all these people around me, how
could I possibly feel this way? And there were a

(26:37):
couple of people that like entered my life that like
gave me some awareness and consciousness, one at the deeply
personal level and one more at the professional level. At
the personal level, I ended up actually becoming friends, and
a person who became a mentor of mine was the
former president i'd say is Barack Obama.

Speaker 2 (26:57):
And it was kind of a.

Speaker 1 (26:58):
Crazy story where I, you know, I, like many people,
met him in the White House, and then we keep
in touch after the White House and he became a
bit of a mentor to me. We developed a relationship,
and initially it was a purely professional relationship, but by
twenty twenty one, after it went public, he kind of
told me. I kind of told him what I was feeling,

(27:19):
and he said, I think you're kind of lonely and
you probably need to renew friendships. And he described that
he had like these ten or fifteen friends, most of
them he was friends with before his presidency, and they
kept him grounded and rooted. And your roots come from
your past, and your past is often your relationships. Because
I kept asking him, like, how didn't you like lose
your mind, He's like, it's hard to lose your mind
when you have deep connections in relationships to others. And

(27:42):
this is around the time I was like totally realized
I hadn't maintained relationships. So one of the most important
things I decided to do was renew the relationships that
were in that invite list, those people that hadn't really
kept in touch with. And so I rekindled relationships with
my college friends, and I committed that we'd take like
one or two trips year, because the problem is if
you don't see your friends, you only text them. The

(28:03):
only things you can talk about are like the same
old stories from twenty years ago. Or you can talk
about other things in your life, but you have no
shared experience in zoom in phone calls and text messages
or not shared experiences. You can only talk about an
experience you had. And so I did that with my
college friends, I did my high school friends. I started
spending more time with my sister and other people in
my life. I ended up getting like a dog, a

(28:25):
Golden Retriever named Sophie Supernova, and the crazy thing Jay is.
I can tell you, like the ride of Airbnb and
having all the success and money and power and all
this stuff, it can be amazing. I'm not saying it's
not amazing, but I actually think I probably It's almost
like I had to go on this entire journey to
realize I had everything I needed before I even started

(28:47):
the journey, that the thing that probably gave me the
greatest life satisfaction was a thing that I didn't even
need money for, and I didn't even need to have
success to achieve relationships many of them I had before
I started.

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Speaker 1 (30:26):
Oh, I think you had Robert Waldinger on your show
and you know he I actually met him last week
for the first time. He is as people listening are
probably realize, he was a Harper professor who's run the
longest study in human happiness. It started before he was
even alive. It's an eighty five year study. And the
question was what's the secret of happiness? And of course
they don't think they thought there was a silver bullet answer,

(30:46):
and of course it is, and it's relationships. And I
think that that's what I've learned that like, as I've reconnected,
I've felt like this light and this love hermeate me.
And I think it's made me a better leader because
one of the things Robert told me is fifty percent
of CEOs are lonely. Now somebody listening to say, oh,
poor CEOs, well, I would say, I don't think I

(31:09):
want society be led by a bunch of lonely people.

Speaker 3 (31:11):
Exactly.

Speaker 1 (31:12):
I don't want society be led by a bunch of
lonely people because lonely people are less trusting of other people.
They're more paranoid, they're less resilient, they will typically have
less empathy because they will push people away. I don't
think they're is connected. They make worse decisions. And so
we do not live in a world where people are lonely,
and we especially don't want to live in a world

(31:32):
where leaders are lonely, and so this has been one
of the defining things in my life. So I think
the first part of the answer is for me to
deal with my own sense of isolation and loneliness. And
because again Jay, I thought loneliness was something that like
people's grandparents experience in their life. I didn't think it
was something the young person experiences. And the other person

(31:52):
I met is the now and former Certain General the
United States with doctor Vec Murphy. We hired him during
the pandemic because a lot of people were afraid to,
like you know, go into airbnbs and they were worried
about like germs on services, and so we hired him
to do this, like you know, basically create cleaning and
sanitation protocols. But I remember having a conversation with him

(32:17):
and he said something to me. He said, Brian, do
you know what the number one killer in America is?
I'm kind of paraphrase in the conversation and I said,
I don't know. Is that like heart disease is a cancer?
And he goes, no, the number one kill in America
is loneliness. And I said, loneliness, what are you talking about?
And he said, yeah, being chronically lonely is worse for
your health than smoking a pack of cigarettes a day
and can take fifteen years off your life. And not

(32:39):
only that, but about half of Americans are lonely. Two
out of three teenagers, by some studies, are lonely. And
it's not just that they're lonely.

Speaker 2 (32:48):
I thought, this is.

Speaker 1 (32:49):
Leading to a lot of mental health issues. You know,
one in four teenagers have suicidal ideations. You know, that's
not just teenagers. You see, like you know, like there's
a crisis with men and boys, there's a crisis with
like one in three seniors or lonely. This is like
so I started realizing this is like a really big crisis.
It's maybe a way of say it's a crisis of disconnection.

(33:10):
And I started realizing, like you know, global warming, maybe
you could say that's disconnection with the earth, and that
loneliness is disconnection from each other. And maybe loneliness at
the most fundamental level starts with disconnection from yourself. That
you're running away from something, and that sometimes trying to
be successful and climbing a mountain is running away from something.

(33:33):
You know, because you think that what you are isn't enough,
and if you become war, you'll be you'll become something,
and that is the problem because of course we never
fully leave our history and our psychology. And so then
I started learning about loneliness at the intellectual level and
started asking what airbeingb's a global community. We have hundreds
of millions of people. Some of the best ways to

(33:54):
connect with other people or through travel. I was using
travel and Airbnb to like connect with my friends because
most do me live in the same city as me.
I started realizing, you know, you get to my age,
you're forty one, you have a public company.

Speaker 2 (34:05):
You have a couple of choices.

Speaker 1 (34:06):
You can just stop and say, like retire, you can
do something new, or you can say my work is
just getting started. And for me, like I want to
of course, I want to like keep getting a return
for shareholders and make sure like if people give me money,
they feel like it was a good decision, If employees
put their trust in me, it was a good career decision.
And I want all that to happen. But that can't

(34:30):
be enough. That there's got to be something more. The
artist to me, the designer and me wants to solve
a problem. The problem can't just be a stock price,
it's got to be something greater. And I have like
the one of the biggest canvasses in the world of
any designer ever. And while I'm a design is not products,
I'm design connections between people. And so I started learning
about loneliness. I started realizing that modern life seems to

(34:51):
be making people lonely. And there's all sorts of theories.
Maybe it's that, like you know, everything is digitized now.
The mall is now Amazon, the theater is now Netflix,
the Courci's stores now in Sikar, the office is now Zoom.
And I'm a proponent of all these things. I use
all these services and I love them. But you know
the problem is, it's like ingredients, we evolved, I think,

(35:14):
to be in physical proximity of another, and as we
spend more time online, we seem to be spending less
time together. And I think we have to be very
very careful as society what kind of future we want
to design for ourselves. So I guess for me, loneliness
in its solution, which is reconnection, has been both a
personal mission and now a bit of a professional mission.

(35:38):
And a product or a service can't help with that,
but a community can and if Airbnb can go from
a travel service to a travel community, if we can
be in the business of trust where you understand one
other and we can help you connect with people in
your life or meet other people, that to me would

(35:59):
be where the next chapter is. And there's something about
like solving your own problem then wanting to like, you know,
trying to spread it to others is I think one
of the most fulfilling things. They always say the best
way to start a business solve your own problem, and
I think that's what I've been trying to do.

Speaker 3 (36:13):
Thank you for coming to my ted to it.

Speaker 1 (36:16):
That was.

Speaker 3 (36:18):
A masterclass on loneliness and I mean that. And it's
beautiful to see how it can so deeply correlate with
what you've already built. And I think that's what as
I'm watching you, and as people are listening and watching,
I want you to take this away that you're not
neglecting or negating any experience you've had. You're actually collecting

(36:39):
they're awesome and bringing them all together and saying, look, actually,
it's additive. I think a lot of us have this
tendency in the material world to build something. Go ah,
it wasn't it throw it away and then go try
and build something else. And actually, what you're saying, actually
I built this thing. It's great, but actually it could
be so much better.

Speaker 2 (36:55):
And it's just the beginning exactly.

Speaker 1 (36:57):
And I also think that, like I'm not saying it
never would have mattered, and don't try to be a
tech founder and don't try to achieve success. I'm just
saying their ingredients, yes, and that if you do it
alone and you don't have relationships and you do something
to fill something in you, it's not going to fully
do that. But if you do it because you love it,
and you get to do it with people you love,

(37:17):
and you can do it out of a sense of
gratitude in giving to other people. You know, Steve Jobs,
one of my heroes, used to say, I get to
work now with Johnny Ive. He started a firm called
Love from Love from Me to You, And that was
the theory that Steve said that. Steve said, the best
way to show your love for the species is to
put your heart and soul into something and give them

(37:38):
to them. Steve said that design is a fundamental soul
of a man made creation that reveals the self to
subsequent layers and I think that ultimately my motivation has
gone from more extrinsic to more intrinsic, that at this
point in my life, I'm less worried about what people think.
I don't really feel like I have to prove anything

(37:58):
in people. Either I already have or I never will
at some point. And I think at some point it
just becomes about the thing. I just want to do
the thing to the purest best of my ability and
to feel like I give to others. And this is
the other thing is it's amazing to be able to
buy things and have things. Those experiences are awesome, But
the things that probably give me most joy is like

(38:20):
sharing things with others or giving things. I totally get now.
I never understood, like why people like giving away things.
I didn't really understand it was not intuitive to make
growing up. I was parents of social worker, I was
kind of middle class. And now I realize there's I
don't want to say a selfishness to it, but you
get something. You get something from giving. It's not just
this moral obligation. You actually get something. And when you

(38:42):
get is this sense of love and connection by giving something,
by giving love, you kind of get it back in return,
And I think, ultimately, like I think me as a
I as a leader, I never saw something like me
growing up. I went to design school and like, no,
there was a there's weird thing Jay where I get
to Risdy the reroons call design, and there was an

(39:04):
obsession about getting designed the boardroom, and Joe and I
were like so like audaciously thought why should design be
in the board and we can run the boardroom. But
of course, like designers that people never thought started companies.
And there's an old saying art is a question the
problem in the world, and design is the answer. And
Joe and I wanted to seek answers to problems in
the world, and one answer was we can't pay rent.

(39:26):
So we created this thing called Airben and Breakfasts airbeds
instead of beds for airben and Breakfast. But ultimately, you know,
I think a business person. I am a business person ostensibly,
but I think a business person's goal is to make
money and a designer's goal is to solve a problem.
And of course I'm doing both. I probably sit at
the intersection, but I don't get out of bed every
day to make money. I get at bet every day

(39:47):
to like design, something amazing, and of course I can
pay money, I can fund it, and that's just a
kind of motivation and that probably can keep me going
for a really really long time. And I find that
a lot of companies they get really cold as they
get big. That you start something for love. You're the customer.
You talk to the customers, and at some point the
company grows and you start with the head and the heart,

(40:08):
you like, putting your love into it. You're intuitive. No
startup is data oriented because there is no data. If
you have an idea, there is no data, So you
go off your intuition. You do something because you believe
in it. And then at some point you get so big,
the company gets financialized, there's a lot more data, and
you start making decisions with the heart and now with
the head and one side of your head. And you

(40:29):
look at the Fortune five hundred. How many CEOs and
the Fortune five hundred are truly like have any creative
background whatsoever? Identifies creators? Almost none? Okay, how many boards
there's twelve members and average of a Fortune five hundred
bard that's like probably six thousand members and the Fortune
five and how many boards have like creative people?

Speaker 2 (40:48):
Not many?

Speaker 1 (40:49):
How many executive teams have it. And so I guess
the question is, like, there's nothing wrong with the scientific method.

Speaker 2 (40:55):
There's nothing wrong.

Speaker 1 (40:56):
It's great, but we need to We talk about diversity
a lot in corporate Mamaer, there's a type of diversity.
We need a diversity of artists and scientists, of head
and heart. You need all those things to solve the
biggest problems today. And if Airbnb could be viewed as
like a design driven company, like the world's biggest risky
project that just never stopped, you know, a company with

(41:17):
like a sense of a spirit, a sense you know,
our logo is like an inverted heart. It was meant
to be this idea almost of this like beating heart,
like this lifeblood that would flow through the community. And
I'm not saying we do all that. That might be
an ideal that we've never gotten to but you can.
But we can or will die trying.

Speaker 3 (41:40):
You've sparked a lot of thoughts for me that I'd
love to share with you. That you've reminded me of
so many things. My mind is connecting so many dots
with what you're sharing. The first thing that came to
mind is it's really there's a beautiful statement by Paul Tillich,
who's a writer, who said that it's fascinating that there
are two words in the English language for being alone,

(42:00):
yet we only use one of them. And he said
the two words are loneliness, which is the word we use,
and the other is solitude. And when you said we're
disconnected from the earth, we're disconnected from each other, but
really we're disconnected from ourselves. It's because of a lack
of solitude. When I lived as a monk, being comfortable
being alone was the first lesson of the day. Wow,

(42:21):
because the idea was.

Speaker 2 (42:22):
That how do you learn how to do that?

Speaker 3 (42:23):
Well, there's many technique techniques. One of the first techniques
is if you just sit with yourself for long enough,
you start to see so much in yourself that what
connects back to what you said at the beginning. If
you're able to explore and take an expedition into the
darkest parts of yourself, if you're able to go into
the inner sky and extrapolate all of the feelings, the messages,

(42:45):
the emotions, the things you like, the things you don't like. Now,
when you sit opposite another human you can see the
complexity and the simplicity of them as well the challenges
we've never looked at our own darkness.

Speaker 1 (42:55):
And there's a great one of the late great mythologists
to the twentieth century you probably knows, Joseph Campbell. Of course,
he had this great quote, the cave you fear to
enter lies the treasure that you seek. And I think
that so many of the things we do in life
are to run away from things, to avoid opening that
closet to see what that monster is.

Speaker 2 (43:15):
But that's where the treasure is exactly.

Speaker 3 (43:17):
And so being trained to sit with that monster with
the discomfort of what that actually looks and feels like.
And what you were just saying now about this heart
and this head, or the design and the art and
the creative and the entrepreneurial. I think it's so powerful
because so you mentioned Steve is a is a hero
of yours. Same with me. I feel like I've studied
everything he's ever said or Wrisen and one of the

(43:38):
things I love this was an interview that Mark Zuckerberg
was doing with Prime Minister Modi from India and he
said this on stage to Mody. I believe this was
in San Franz and Mark said to him, he said,
when he was struggling with the direction of Facebook now
meta in two thousand and nine, which is five years old,
Facebook is right. He went to his mentor, his mentor

(43:58):
having to be Steve Jobs, and he said to Steve,
he said, what do I do. I'm struggling. I don't
know which direction Facebook should go in. Now, if you
think about two thousand and nine, Steve Jobs is undoubtedly
one of the most connected humans on the planet, has
access to money, tech, everything you could possibly ask for.
And Steve says to him, I want you to go
and live in an ushram in India. Wow, for I
want you to go live then, I promise you if

(44:20):
you go there, you'll figure out the direction of Facebook.
And Mark said he actually went to that monastery, that ushram,
and he said, in that ushroom, that's where he decided
that at that time, Facebook was about connecting people.

Speaker 2 (44:30):
Oh wow, and yeah.

Speaker 3 (44:32):
And what I find fascinating. The reason why I like
to share that story is I'm always fascinated by what
a tech entrepreneur thinks as much as what I'm fascinated
what a monk thinks, because it's that cross pollination, it's
that extreme of diverse thought, where those two things don't collide,
they don't have the same agenda. We're not living in
an echo chamber. When you're talking to an artist and

(44:52):
an entrepreneur, there's no echo chamber. You've broken it open
now and so for me. MIT did a study on
that where they found that the most innovate of employees
inside an organization were people who didn't know people who
knew the same people. There were people who knew people
who had random connections, so their network chart was completely uncorrelated,

(45:12):
whereas people who had networks who were correlated were less
likely to be creative and.

Speaker 1 (45:16):
On a fewer unknown discoveries. And I feel like in
my own life, like Steve has saying, you can't connect
the dots looking forward, you can only connect them looking backwards.
I grew up playing ice hockey, I played team sports.
I went to a military high school, a design college
where I first studied fine art, then design. Then I
went to MIT for a semester with a cross enrollment

(45:38):
product development program. Then I went to Los Angeles as
in a designer at a firm. Then I went to
Silk and Valley with very little and like got thrust
into the technology industry. And it turns out that like
I did not know how any of these experiences would
add up together, and they all came to me and
every single one of them have used every single experience,

(46:00):
but I could never have reversed engineered how to get there.
And it is amazing that, like Steve used to say,
the best engineers were also poets, and it was really
saying that, like creativity is about connecting dots, it's about
having disparate experiences and bringing them to together. And if
you haven't had a lot of different experiences, if you

(46:21):
aren't very multidisciplinary, you're not going to be ill. I mean,
Einstein was like a violinist. I think a lot of
the greatest scientists have leaps of the imagination. They're not
just using empirical information. And a lot of the greatest
artists they haven't organized minds. Sometimes they have a fascination
with numbers, and so you start to you start to
bring things together, and I think that is exactly what

(46:43):
we probably need in this world. I mean, we need
more creativity. You know, whenever you see two bad options,
you don't like it. The right answer is the third option.
The third option is one you haven't come up with
yet that requires novel, innovative, imaginative thinking. Where does it
even come from? Where does creativity come from? Activity?

Speaker 2 (47:00):
You know?

Speaker 1 (47:01):
But I don't know if Einstein never said this, but
there's a quote attribute to him that is that logic
can take you from a di zy, but imagination can
take you anywhere. I love that quote. Don't know if
you said it, but I believe it. But where does
that come from? Where does imagination and creativity come from?
I think comes from a sense of openness, It comes
from curiosity. It comes from maybe not first following your passion,

(47:23):
but following your curiosity with a deep intensity, and being
curious about so many different things, and trusting that you
can be curious about something and learn about something, not
knowing it will ever be useful, and have the trust
to say that every single thing you'll do in your
life you'll do with accumulation of every single experience you've
had before, and that the more places you've gone, the

(47:45):
more people you meet, the more things you learn, it
will all come to you and you might not know
ahead of time how it will be useful. And honestly,
if I hadn't gone to military school, I probably wouldn't
been so organized. If I didn't go to design school,
we probably wouldn't have been as creative and innovative in
our thinking. If I hadn't played team sports, I probably
wouldn't have understood about camaraderie. If my parents are social workers,

(48:07):
I don't think I would have had this focus on
service and connecting people.

Speaker 2 (48:12):
And I could never have imagined any.

Speaker 1 (48:14):
Of those things being useful because growing up, I didn't
know what I wanted to be. I wasn't athletic enough
to be a famous athlete. I was enhanced enough to
be an actor. I wasn't going to singer to be
a musician. I did not think I was going to
be an astronalm politician. And so I'm like, I don't
know who I'm going to be. I don't know what
I am, And like, the word entrepreneur was a word
I'm not even sure I heard of growing up. It

(48:35):
was like to me it was an obscure French term.
I didn't know what it meant. And I saw Walt
Disney as a kid on television. I thought one day
I'll work for him, not thinking I would start a
company just like him. And I never imagined that was possible.
I guess we're all born with unknown potential, as I
said before, but you have to live experiences as many
as you can you put them together. And I hope

(48:58):
my story inspires people, not for the remarkableness of it,
but the ordinariness of who I was before to say that,
like if I joined the Gift in Giving Pledge, if
you ask my teachers in high school to predict which
of their students would be a signatory the Giving Pledge,
I do not think I would have been the top
of their list. I don't think that takes anything away

(49:20):
from the teachers. I think it just means that maybe
that potential is in so many of us, and it's
also maybe a little bit random in anything as possible,
and you like the story you tell yourself might not
be accurate. And I hope that my story inspires people
from the ordinariness of where it came from. That I
was just like everyone else, but like you know, one

(49:42):
hundred thousand decisions later, with enough resilience, creativity, curiosity, and determination,
you wake up one day you're like, oh my god,
look where I am.

Speaker 2 (49:51):
Now.

Speaker 3 (49:52):
What I really value about that perspective is as you
were defining creativity in so many brilliant ways. One thing
that came to my mind was creativity is being able
to connect the dots where everyone else sees anomalies. Yes,
and so if you look at your journey just as
a series of random dots, they're all anomalies. Social working,
hockey player, design student, like, they're just random things. But

(50:15):
you're able to actually paint this tapestry where you're going. Well, actually,
everything that I do today and I've often felt that
in my own life that I lived as a kid
growing up in London. My favorite subjects at school were
are in design, philosophy and economics. Those are my favorite
things in the world. Spent my entire life being immersed
in that world. When traded it in to go to

(50:35):
cast Business School to study management science with a focus
on behavor science, because I thought it gave me a career,
only to give it all up, the safe job, to
go live as a monk, to then come back to
the real world, go back into the world of business
because I just had to pay the bills and survive,
went into consulting, then came out and do media now.
And I completely agree with everything you've.

Speaker 1 (50:55):
Just said, probably the thing that makes you so unique
is like you were a monk and you are an entrepreneur,
and you lived in London and you lived in New York,
and like the accumulation all those experiences together, right is
made has made you who you are, not one of them,
all of them. And I think that like the one

(51:16):
advice I would give my college self is to try
more things and have more experiences and don't seek status.
And part of the reason why one should not seek
status is because we can't even predict what industries will
be around the future. Like growing up, status to me
was like I don't know, it was like being an
investment banker or something or something, and I don't know,
it was like fields that may not even totally exist

(51:38):
in their current form in the future. So you know,
I like to say, like you should do things you're
good up. You tend to be good at things you're
interested and you should seek out whatever you're curious about,
whatever you're interested in, and then you want to get
to the frontier in some way. At some point you'll
learn everything and you'll get to the edge of all
that's known about that subject. And that is an uncomfortable period.

(51:58):
Where you spere off the ledge of a cliff, and
that is where you enter a frontier. And if you
can then pure of the edge of cliff and then
get a little bit further and extend or understand and
give us a little bit more land, that is how
you like add to as Steve Jobs said, that's how
you give your love back to the species and create
something for other people. And I think, I think it's

(52:19):
amazing that like anyone can do that. You know you
can do it because anyone can do it any scale,
you know, and you can do it in your humble way,
like on the side, something small, or you can do
it in a really big way. But it feels the
same no matter what the scale.

Speaker 3 (52:32):
You just thought us what you'd say to your youngest
self if you met your youngest self. Now, let's do
this exercise. What do you think your youngest self would
say to you? What would it be proud of? And
what would your youngest self say, we need to reconnect
with this.

Speaker 1 (52:47):
The first thing my younger self would say is, oh
my god, how did you do all this? And I
would be totally perplexed. When I started, me and my friends,
I said, this will be huge one day, thousands of
people will do this like that was my sense of
what was possible. It's hard to dream of something you've
never been exposed to, and it's hard to imagine becoming

(53:08):
something when you didn't have any data that you could
ever do anything like that in your past. And so
I do not think my younger self, I'd say, my
college self, did not think I could run like a
fortune five hundred company. You know, you know, for every
one thousand, five hundred dollars spent in the world, one
dollar spent in Airbnb, did I think I get lead

(53:28):
an organization that's facility on?

Speaker 2 (53:30):
No, I did not think I did.

Speaker 1 (53:31):
And so that would be probably the thing I would
be like surprised in a very positive way. But the
other thing I would probably say, as well, I'm forty
one years old when I live alone, and I probably
thought by now I would have a family, and.

Speaker 2 (53:47):
I've always wanted to have one.

Speaker 1 (53:50):
And I think that for all the like attention adulation
I get, I think I would have maybe looked at
my life now or my recent life and identified a
little bit of isolation. And I think the lesson is
the couple things. One I think that things have happened
in a different order than I imagined. It's hard to predict.

(54:11):
I thought I wouldn't. I didn't think i'd be this
far along in my career, and I probably think I
probably thought i'd be further along and have something different
in my personal life. And I also would probably I
would hope the college me would tell myself, now, you
don't have to keep proving something to anyone, because you've
proven more to me than I ever thought was possible.
And I think that, like part of me, and this

(54:33):
is probably true of a lot of people, we have
this tape loop of like whatever we thought ourselves as
a child, like it's just frozen in times, repeating ourselves,
and you just compulsively just keep doing something. And like
many people have addictions, and I probably had one that
was probably work, and I think i'd have to. I
would hope my child self would or my younger self
would remind me that, you know, maybe there would be

(54:54):
a wisdom that like the happiest periods of my life
were with other people.

Speaker 3 (54:58):
Thank you for that, thank you for opening up and
going there. And I felt that what is a thought
that you say you have? Too often?

Speaker 1 (55:05):
I wonder what they'll think speaking of doctor waldenker Robber,
But I met him last week for the first time,
and you've had them on your show.

Speaker 3 (55:13):
Right, Yeah, we've spent a lot of time together. I
love them.

Speaker 1 (55:15):
Something you told me last week that really stood out
to me said, one of the biggest regrets that people
have in their life is having lived their life worrying
what other people think. And I kind of understand why,
like from a like evolutionary standpoint, like you kind of
have to care people think because you have to fit in,
and if you don't fit in, you don't belong.

Speaker 2 (55:33):
You're isolated.

Speaker 1 (55:33):
If you're isolated, it's a death sentence when there's the
only thing you have is the village. But it turns
out that like that is not true anymore, that like
it's okay to be misunderstood, and that it doesn't maybe
it doesn't matter what people think, or maybe it doesn't
matter what you think today, and that some of the
greatest things I've ever done I was at least temporarily misunderstood,

(55:54):
and maybe it only matters what a few people think,
and maybe just maybe the person that most matters what
they think is yourself. Right that you just listen to
your own voice, not other voices. And I think if
I can do that, you know, artists will call the
artistic integrity, right. You had Rick Rubin on the show.

(56:14):
He talks about, like the best way to make a
popular song is to make something you like, and that's
about it, not make something for somebody else. And that's
that's something I have to continue to do. And the
crazy thing is the more successful you get, the more
you start kind of performing for an audience. And you
have to be very careful about performing for and appeasing

(56:37):
an audience. And once you become something, people expect you
to be that thing. You know, imagine like you happen
to be something forever. But what if you change? What
if you grow? What if you want to do different things?
And that's a challenge I have right the air, and
Bee brand means something. I be careful about changing that brand.
It stands for something. And yet I, as a person,

(56:58):
am not meant to be the same person every year.
I mean how could I be? I learn, I grow,
I change, I have new experiences, and so having the
permission to continue to change and evolve and not be
so self conscious of what people think, that's something that
I always struggle with because I don't know part of me.
I think I'm like a people pleaser, and one of

(57:18):
my challenges historically be is like some people like, I'm like,
I don't always like interpersonal conflict. I like to appease people,
make them happy, and that's got a good side, and
it also can be a bit of a prison over time,
and the bigger you get, the higher the walls get.

Speaker 3 (57:35):
I want to just point out something you said that
was so subtle but so powerful for everyone's listening and watching.
I've never heard it put that way, but the idea
that we often think it doesn't matter what people think,
and you said, it doesn't matter what they think today,
And that was so subtle but so powerful, because I
think when we live in a world we're like, oh,
it doesn't matter what anyone else thinks. It's it can
be negligent. But the idea that it doesn't matter what
they think today about what I'm thinking, and.

Speaker 1 (57:57):
Thank god, yeah, thank god.

Speaker 2 (57:59):
You know why.

Speaker 1 (58:00):
When we first came to the idea, one of my
first investors said, don't worry about people stealing your idea.
If it's any good, everyone will dismiss it. We tend
to believe things were good. In hindsight, some of the
most revolutionary people and ideas were revolutionary because they're misunderstood
in their time. That if you have to be at
some point in your life willing to be misunderstood and

(58:22):
the solitude you can have are two things.

Speaker 2 (58:24):
I think.

Speaker 1 (58:25):
Number one, to not be so attached to it, to
realize that ultimately you can't predict the outcome. Just do
what you believe, follow your heart, and if it's true,
whatever has happened is meant to be. But the other
thing you can do is to escape into the future,
to say, to have this vision we call the vision
for a reason, you've envisioned something that people don't see it,
and say, I'm willing to be mis understood to try

(58:47):
to follow this thing, and if I believe it enough,
eventually other people might see it. And if you are
able to be misunderstood just for a little bit, that's
what it feels like to truly revolutionize something and change something.

Speaker 3 (59:02):
There's a beautiful statement which is probably my favorite, which
you've just encapsulated so well. It's from Charles Houghton Cooley.
He wrote it in eighteen ninety six or something, like that.
So he said this early and when you hear it,
you're like, wow, that was said yesterday. He said, the
challenge today is I'm not what I think I am.
I'm not what you think I am. I am what

(59:23):
I think you think I am. Oh, And he said,
we live in this perception of a perception of ourselves.
So we don't even know what we look like. We
are who we think other people think we are. And
that's twice removed from yourself. And that distance we create
from our understanding of ourselves versus what we think someone
thinks of us totally, how will you ever know? What

(59:46):
do you think is something you are still trying to
understand about yourself? Or if you think you misunderstand a
part of who Brian is, what are you still trying
to understand?

Speaker 1 (59:56):
I think that we tend to have an outdated image
of ourselves and that makes sense, right, Like, think about
I'm forty one years old, so my image of myself
is the average of the last forty one years. And
if the average the last forty one years, the median
is twenty years old. And so I still see myself
a little bit like that person and people most people
see me today and a lot of people are going

(01:00:17):
to see me for the first time right now, and
that's their impression, and that's a delta. And I often wonder,
like sometimes I, you know, I probably have had a
little bit of imposter syndrome, like what do people see me?

Speaker 2 (01:00:29):
And why do they follow me?

Speaker 1 (01:00:30):
And like because they do, Like at some point you're
a leader, and you're a leader because people choose to
follow you and you don't like impose yourself on them.
They ultimately believe in something. And I think I'm still
trying to like maybe come to terms with that, like
what does this all mean? I think I'm still trying
to understand what will make me happy, especially at a

(01:00:50):
personal level. I think I've found what will make me
happy at a professional level. I was really lucky that
I discovered something that I love very early on. I
found a perfect harmony between what I was good at,
what I loved, and what kind of society valued, and
those things just clicked into place and I was able
to find it. But I think I've been on a
lot longer journey to figure out like what will make

(01:01:15):
me happy, like in a larger sense of the word.
And it turns out that success and status to some
extent have benefits, and you know, but it's not it's
certainly to say it's not. Everything's an understatement. I think
I'm still trying to I was still trying to learn that,
and maybe I'm trying to figure out, you know, at

(01:01:37):
this age with so much so many resources, like I
almost feel like in a way, my life's just beginning,
and so it's just beginning then, and I can't connect
the dots looking forward. It's a discovery of who am
I and who am I meant to become? Like is
this my story or is this the end of the
middle of the story the beginning of the story, and

(01:01:59):
what am I meant to do next? And I'm kind
of learning a lot more about myself every year.

Speaker 3 (01:02:05):
That's a brilliant mindset. That's so empowering, and I'm hoping
for everyone's listening and watching.

Speaker 1 (01:02:10):
That is so.

Speaker 3 (01:02:12):
Phenomenal to hear from you, because that is the journey
of life. Like the questions you just laid out, Like
if you weren't asking those questions, how boring would life be?

Speaker 2 (01:02:23):
Like?

Speaker 3 (01:02:23):
How unmeaningful and unfulfilling would it be? And the fact
that you're ansking those questions at this.

Speaker 2 (01:02:28):
Point, maybe one of the things I ask, oh, of course,
you can add wherever you want.

Speaker 1 (01:02:32):
So over a year ago it was February Russian Vita Ukraine.
We got word that there'd be like millions or refugees.
And when this broke out, I remember my co founder
Joe calling me up and him telling me something. He said,
when a crisis of the scale happens, we should ask

(01:02:54):
ourselves one question, and that question is how can we help?
And I always wanted to believe that if I was
like a CEO durn World War two, I would have
like been helpful, and I want I always try to
use That's the other device I use. I try to
think about how I'll be viewed in the future, but
I also want to I always think in how do
I want to be remembered even if no one will

(01:03:14):
remember me? And I think anyone can do that. How
do you want to be remembered by history, even if
it's just an intellectual device, because maybe not a lot
of people will remember. That's okay, but live your life
as if you be remembered. And what I realized is
one of the most important things. And then we ended
up helping provide housing for one hundred thousand refugees, and
it was an incredible team effort, but it came from

(01:03:36):
this basic idea of how can I help? And maybe
that is the other version of my question in my
life at this point, you know, how can I help?
With everything I have?

Speaker 2 (01:03:45):
That?

Speaker 1 (01:03:46):
I mean, I've hired some of the most talented people
in the world, we have enormous amounts of resources, we
have this incredibly advanced technology, I have this pretty big megaphone.

Speaker 2 (01:03:57):
What do I do with that?

Speaker 1 (01:03:59):
And I hope that what I do provides me happiness.
And I've noticed that the things that make me happy
are like kind of helping and giving others. I don't
mean to sound cliche, but like you start to realize
like what provides happiness and value for you. And so
that's kind of something that I keep thinking about. And
that's what I love about, Like entrepreneurship and creativity and design,

(01:04:21):
is you make something, maybe initially for yourself, but then
for other people, and the real joy is seeing them
use it.

Speaker 3 (01:04:28):
Absolutely, I think I was really fortunate when I lived
as a monk. Service was trained as the highest act.
Service was like imprinted in US as the highest act
that the act of giving, the act of serving others
the interesting, and it was so counterintuitive to everything I'd
learned growing up in London, because it was always about
getting and achieving, and giving and serving were never part

(01:04:51):
of even our vocabulary, let alone being a part of life.
And I realize now, and I see that today, that
when everyone, when anyone gets to point of getting everything,
all they can do is give it away in the
right in a way that fuel them to a mission
that is aligned with their purpose, not just not just
you know, wherever it goes exactly, but in a meaningful way.

(01:05:13):
You talked a bit about which I loved about the
you know, the younger self saying back to you that
you know you thought that things would happen in a
different order.

Speaker 2 (01:05:22):
Yeah, totally.

Speaker 3 (01:05:22):
When you think about that, being single being in your words,
like being lonely. You're such a mastermind at so many things.
What's the thought that blocks that? What's the worry that
comes up, the anxiety that stops you from masterminding that
part of your life.

Speaker 1 (01:05:40):
I've been able to look and sign myself to know
a number of things. I think that I grew up
feeling a little bit like an outsider. I wanted to
feel like anyone like I belong and I found through
achievement that, you know, I would feel these feelings that
I thought were like love of it, and I would

(01:06:01):
feel better, you know, and all that. And I think
it's this incredible and positive to a point, but if
you're not careful, it can become all consuming. And the
thing about a tech company or a startup is like
it's like imagine you, like again, you have a three
percent van that's now thirty thousand percent man, or you know,
a three million person. It just there's always more you

(01:06:22):
can do. It can if you're not careful, become like
a one dimensional addiction. And I think that it's like
the thing that made me successful was my singular focus,
but I have to be careful that the thing that
could then turn against me is my singular focus. And
so I think it's like, what I the way to

(01:06:45):
live my life in the next twenty years can't exactly
be what I did last one years, But last one
years worked out pretty well, so why would I do
anything differently? But of course, if I don't do anything differently,
and I'll be fifty or sixty and nothing will have changed.
And so I think it's really out like seeking community.
The word community means harmony, to live in, harmony, in

(01:07:06):
balance and having that, And so I think it's just
old habits and habits that have been rewarded. So, but
you've got to be very careful about those habits. I
think that. I think that's what it is. And I
also just yeah, I don't know, what do you think.

Speaker 3 (01:07:22):
When I listen to you and being with you for
the time that we're spending together, and obviously it's the
first time we've met. Yeah, you're someone who has extreme
clarity about what you want, who you are, what you're
working on, what you're struggling on. And my question would be,
or my hypothesis is, does that clarity exist around what
you want in the personal space.

Speaker 1 (01:07:43):
I think that's a big insight. Yeah, and maybe that's
what I'm still trying to discover.

Speaker 3 (01:07:46):
Yeah, I would say that you sound so clear, Yeah,
that if you actually had clarity, then I don't think
it would be hard. It's hard to have clarity. That's
the hard clarity.

Speaker 2 (01:07:57):
That's a good point.

Speaker 3 (01:07:57):
And so when you have clarity, it will be so
much more easy if you to create, you can't create
something if you don't have clarity, that's a great point,
and so that would be my Yeah, I love that
at least, and that's what I was going to ask you,
my what at least are those sprinklings of those clues.
Let's let's go with that word, what is what are
the clues of what you think could develop into clarity
around what you're looking for in a personal way. You've

(01:08:19):
talked about so prolifically about what you want professionally, which
is this using Airbnb as this phenomenal platform to build
community and connect people and you know, eradicate loneliness, which
I love, Like, I love that. That's phenomenal clarity and
so inspiring and I could get behind that today, right,
Like that's so what do you need to get behind yourself?
In the personal space?

Speaker 1 (01:08:38):
I feel like I'm professionally like a sixty year old
and a forty one year old's body, and personally like
a twenty five year old and a forty one year
old's body, because I'm like I'm foot in the future
and foot in the past, or like I'm in totally
different time scales professionally and personally, and it kind of
makes sense right where I am a whole bunch of
my life maybe was a little more on hold or

(01:08:59):
done in a differ order than I imagined. So the
question is, like, how do I get clarity when I
started Airbnb? Before before we started Airbnb, I didn't know
I wanted to start a tech company and I wanted
to be like about bringing helping bring people together. And
I was going to start with these two people, and
I was going to be a technology founder, and I
was going to marry art and science and do all stuff.

(01:09:19):
I couldn't have known any of that, but there were
some things I did professionally that are probably clues to
what should be done personally. The first thing is I
had endless curiosity. I had role models, heroes, people I
looked up to, and you know both you know, well
known people and lesser known people. I had an intense curiosity.

(01:09:40):
I was drawn to certain types of people, and I
had action. You know, it's like, if you can't follow
your passion, you follow your curiosity, where does it take you?
And you know, like, you're not going to start a
company by like never like starting, and you're not going
to build a personal life you want by not starting either,
and so you just go on that journey.

Speaker 2 (01:10:02):
And you will, you will.

Speaker 1 (01:10:03):
I think you will find what you want if you
start and you keep moving.

Speaker 2 (01:10:06):
Yeah, that feels right something like that.

Speaker 3 (01:10:08):
I'm excited to see you, you know, I'm excited to
hear about how you take that short moment of clarity
that we've gained into the future.

Speaker 2 (01:10:18):
Because no, that's great.

Speaker 3 (01:10:20):
I really, I really really feel that you've found in
your life that you've always been exactly where you're meant
to be, not in the luck sense, like you said,
of the right timing, but that each one of your
experiences totally has made you make better decisions.

Speaker 1 (01:10:33):
And I think that that maybe the like exciting thing
is like what if I can't connect the dots looking forward,
but I will realize in hindsight, Wow, everything just fell
into place, like this thing led to that thing led
to that thing. Yeah, and that would be fun, be
fun to check in in a handful of years and
see what played out.

Speaker 3 (01:10:50):
Yeah, yeah, definitely, definitely. And it's so it's so interesting
that you keep quite. I've never met someone who loves
quotes as much as I do, so it's uh, it's
fun hearing them back from you and how they've played
out in your life, What if anything today, apart from
everything we've talked about, we talked about so many things,
What if anything today keeps you up at night? What
do you sleep pretty well?

Speaker 1 (01:11:10):
I don't know if I sleep that well. And I
not to use another quote, but Pablo Casa is saying
the older you get, the stronger the wind gets, and
it's always in your face. And I think that could
be true of companies. What keeps me up at night
is you know, like people ask me the professional context,
So what keeps you up at night in the company, Like,
is this something happening? What keeps me up at night
is something not happening. What keeps me up at night

(01:11:33):
is the idea that we grow into something that I like,
was meant to disrupt two thousand and nine. Everybody takes off.
So we start in twousand and seven, two eight, it
takes off. By two thousand and nine, I go on
a ten year journey. It's now late twenty nineteen, and
I remember having a dream, a bad dream, that I
woke up and I was running a company that's unrecognizable

(01:11:54):
from anything I ever intended to start. It was like
I was in a wilderness for ten years and I
just back and I remember going on a hike in Bilinas, California,
where Joe had like a summer house, and we went
on a hike Joni and I and I told them
about this dream and they said, well, what did you find?
I said, I was horrified because the company we set

(01:12:15):
up the start is unrecognizable we have today.

Speaker 2 (01:12:17):
And they go, what do you mean.

Speaker 1 (01:12:17):
I go, well, people are complaining that it's big, it's bureaucratic,
it's slow moving, people are more complacent. Costs is rising,
grosses slowing. It's starting to feel like a corporation. And
I didn't know what to do. I felt like we
needed to like not blow it all up, but change
it all, like take the house back to the studs.
But the problem was we're about to go public, and

(01:12:38):
that's like a really bad time to do that. But
I had this image in my head of this kind
of company that I want to have. This image was
to build the most creative place on earth, to build
the world's biggest startup, to build a company that was
like felt small, that was completely focused not on a
product or service, but a community. I was starting to

(01:12:59):
come a conclusion by two thousand nineteen that you can't
be big and have a soul like that. At some point,
those things were at odds that the problem was being big,
and I didn't know what to do. And all of
a sudden we get word in February twenty twenty that
our China business has collapsed by eighty percent because this
thing called COVID, Like what's covid? And then within eight

(01:13:22):
weeks you lose eighty percent of your business. And I've
never had a near death experience, but it's been described
to me as your life flashes before your eyes. And
I had a near business death experience and then suddenly
everything making clear to me. If I was seeing this
chair three years ago, I would not have been clear.
I don't think I would have the clarity ad today.
There's something about almost losing everything and everything I had I,

(01:13:45):
at least at that time, I thought was the professional
that gives you clarity. Imagine your house is on fire
and someone says you can take twenty percent of the
things out of your house. Suddenly you have to make
that choice, and you get really clear about what's important.
People started telling you I want to air me exist
you say why, and they tell you it's as if
they're giving the eulogy before you're even dead, and how

(01:14:08):
you want to be remembered, and you start to ask yourself,
I don't know what's going to happen, but how do
I want to be remembered? And at that point we
stepped into action and we basically rebuilt the company from
ground up. And this is to again bring it back
one more time to Steve Jobs. I met two people
at that point in my life who changed my life.
One was Johnny Ive, who was Steve's partner in design,

(01:14:32):
and the other was heiroki Asi, who was Steve's creative director,
and they told me about the way Steve ran the company.
And actually a funny even further aside is I remember
one time I remember went to Steve's house. I never
met him, but and I saw these books on the
shelf from ropin' amin i'mer and asked is like, wife, like,
what is what they're rap?

Speaker 2 (01:14:52):
And I'm air books.

Speaker 1 (01:14:53):
But as I started studying, I realized that it was
this idea that you almost like Rober happened on the
whole bomb in his head, that this idea that the
leader collects all the information and that you're the center.
That it's not a pyramid, you're not top down, you're
inside out. You're the sun of a solar system. But
your job is to emit light and bring decision making in,

(01:15:15):
to pull in this shared consciousness. And I started realizing
there was a whole new way to run a company,
a company that wasn't divisions. Think about what that sounds
like divisions. We are divided, but totally integrated as small, lean,
elite as possible, creative and analytical, technology and humanities. That
we'd have one flow. We wouldn't be metrics oriented, we'd

(01:15:37):
be basically idea oriented, and we'd measure the results and
that we would just there's this really specifically ran a
company and that was basically the way I found ourselves
out of a crisis. And so the lessness story is
through that I was able to get a lot of
clarity through this crisis. I was forced to answer and

(01:15:57):
ask all these questions that I ever had to do before.
But I hope on the personal side, I don't need
a crisis to answer those questions.

Speaker 3 (01:16:05):
Yeah, that's exactly where I think we're headed. That you
have you have an opportunity to avoid the crisis. Yes,
in order to not.

Speaker 2 (01:16:13):
Be not everyone needs that crisis.

Speaker 3 (01:16:15):
No you don't. It sounds like do you do you
still when you present ideas, this a visual you see
them feel you can see everything that you're talking about,
and I can, I can see it with you.

Speaker 1 (01:16:26):
Everything in my head, my mind is like a three
dimensional model, and all my ideas. Think of it like
a tree. The trunk of the tree is your very
first principles, your root ideas, and then they have branches,
and the branches have branches, and those branches have leads
or it's like a space, a three dimensional space. It's
multi dimensional and colorful. And this is what we called

(01:16:47):
the model, your model of the world that you want
to live in. And as you gain more information, you
keep changing the model in your head. I kind of
describe my mind running airbnbas. Imagine a chessboard and there's
that you have to see if he moves ahead. Now,
imagine like a die, a thousand sided die, each playing
a separate game of chess, all simultaneously anticipating in understanding relationships.

(01:17:11):
As hard as that is, if you can start to
organize all the ideas in your mind but not be rigid,
continually changing and orienting it, like, you know, this is
how I tend to see things in three dimensions spatially.
It's really rich, vivid colors, and that's just how I think,
you know. I think other people will think in abstract

(01:17:31):
thoughts or numbers, some think in terms of language, But
that's how I do it, you know, And it probably
doesn't surprise you given my background.

Speaker 3 (01:17:39):
And do you see yourself in that or is that
happening and you're observing it?

Speaker 2 (01:17:44):
You know, you might have hit on something.

Speaker 1 (01:17:46):
There have been times where I'm trying to design a
world that other people want to I want other people
to live in, and I think it's like I want
to vicariously live through them. It's like I want to
design this house that's the nicest house world for everyone
to live in. But I'll be in the workshop design
the house, and sometimes I have to stop to say,
maybe I should step inside the house, and.

Speaker 2 (01:18:08):
I think that.

Speaker 1 (01:18:11):
I think that's a crux of it, actually, and the
answer your question. I sometimes see myself in the house,
and sometimes I see myself just kind of almost like
a monk or you know, a in a technical and
design monastery, like you know, and that's kind of what
the pandemic was. I described it almost like a monastery,

(01:18:33):
except with zoom. But if you didn't know I was
on zoom, you just think I was meditating all day, right,
Like I'd just be sitting in one chair. And so
that's a great thing. Is I think that sometimes many
times we as leader, especially tech founders. I think that
many tech founders basically design the kind of world they

(01:18:54):
want to live in because the world they grew up
in was inadequate in some way and did not make
them happy. I think the challenge of those tech leaders
is to make sure that they step inside that world
and live that world themselves. And you don't do it,
then sometimes you start to like forget why you do
things and you get disconnected. Wow, just kind of you're
making me think of all this.

Speaker 2 (01:19:15):
Now you're making me think too.

Speaker 3 (01:19:17):
I love it, No, And that resonates so deeply and
strongly because I also think that without purpose, tech entrepreneurs
also can sometimes not even just tech entrepreneurs, entrepreneurs in
general or anyone can build something that they monetize that
they would never want to live in too.

Speaker 1 (01:19:33):
Yeah, and sometimes people don't know why they're doing it. Correct,
they started it for a reason. Maybe the reason was
extrinsic I want to be rich and successful, but maybe
it was intrinsic, maybe there was something. But even so,
then you find yourself waking up one day asking why
am I still doing this? And you know the number

(01:19:54):
of people that forget why they're doing it, the number
of people that are self driving cars. There's a destination
that's in the car they're driving towards it, but they
don't even know what that destination is. And that's when
you don't look inside yourself, and if you're not careful,
you will basically be on a super highway going somewhere,

(01:20:15):
not knowing why you're going there, and you may wake
up and end up in a destination that wasn't where
you intended. I think this having this clarity is so important.

Speaker 2 (01:20:24):
Who am I? What do I value? Like?

Speaker 1 (01:20:26):
What do I want to do in this world? It's
like taking the time to reflect. I think the best
businesses are really introspective by introspective leaders. Like when we
started the company, were really clear, here's our mission and
it wasn't just like a mission statement, it's like, here's
exactly what we're trying to do, and now what changes here?

Speaker 2 (01:20:42):
Are values.

Speaker 1 (01:20:43):
Here's the kind of people I want to like work with. Well,
what do they all have in common? They're curious, they're optimistic,
they're kind of creative, they tend to like like hosting
other people. Okay, those become what we call values. What
are the shared lessons? What are the shared stories? And
the more you can start to be really reflective, You're right,
the more you're clear about what you want, the more
you get it. Our problem isn't in life, probably that

(01:21:05):
we don't get what we want. The problem is we
don't know what we want maybe or we pursue things
on your consciously wanting that our counterproductive to make us happy.
And if we can just wrap our arms around that,
some of the hardest things to change our own thoughts,
but in a weird way, they also seem like the
most possible to change. And so that that's something that

(01:21:26):
I've seen and like. Some of the loneliest people I've
met are some of the richest people I've met. Some
the most isolated people I met are some of the
most successful people I met. The most confused people I've
met are the most powerful, because at some point the
power and success can be confusing. You know you had
a purpose, but you also have all these demands and
you stakeholders. You can get fused by appeasing people, and.

Speaker 2 (01:21:49):
You like that. I think that happened to me.

Speaker 1 (01:21:50):
Like I think I started Airbnb and I had a
really clear vision, and I think I've got into a
wilderness where I kind of got confused. And a lot
of founders have described becoming confused. A lot of leaders
get confused, and I totally see how that happens. And
I think finding your way back home is key.

Speaker 3 (01:22:10):
I would be intrigued to see if you close your
eyes now or whenever you chose to, to see what
you saw when you look at your personal life. You're
talking about your professional life as being all these thousands
of decisions moving, and.

Speaker 1 (01:22:24):
You say, like, I kind of that period of self reflection, right, Yeah,
Like I think I saw somebody who.

Speaker 2 (01:22:29):
Was kind of.

Speaker 1 (01:22:32):
Almost punishing myself in romanticizing suffering because I thought, you know,
at some extent, I maybe believe that I was going
to give everything to the company and it was like
this selfless act. But it became so selfless that I
then could start to lose a sense of myself.

Speaker 2 (01:22:50):
I mean, you know how weird it is.

Speaker 1 (01:22:52):
I always kind of joked like if I die, well
I die Brian Chesky or the Airbnb guy just died,
you know, like and like am I Brian or my
and being like, you know, like they get really one
is an icon that's a noun and verb you knows
ubiquitously around the world, and the others a person that
not a lot of people know, really know. And when

(01:23:14):
you it's very careful. I started becoming the company, and
this company started becoming me, and I think seventy percent
of that was good because that meant the company, I
think was a person, had a face as humanistic, it
was in the details. But when you become a company,
you seize to be a person, and then you lose

(01:23:35):
a sense of yourself and then you become an icon.
And by icon, I don't mean famous, I mean iconography.
Icon is short for an iconography, and iconography is for
for a symbol for something, And of course people are
much more than symbols. And I started seeing that I
started becoming a symbol and a thing, and I stopped

(01:23:57):
listening to myself.

Speaker 2 (01:23:58):
And by the way, like.

Speaker 1 (01:23:59):
You get pressure from shareholders to like drive a stock price,
you get pressure from you know, employees to make it
a better work environment. You get pressure from host but
no one gives you pressure for yourself and your personal life.
If you don't create that own pressure, you will like
that will be the like that's the one person that
may not put their hand up. Hey, everyone else will.

(01:24:20):
And if you don't listen to yourself. And I think
that's been part of the second chapter of my life
is like kind of designing the world I want to
live in and then living in that world and choosing
to actually live in that world, and you'd be I mean,
you've interviewed so many people, so but I'm so surprised
how many leaders don't actually live in that world. I

(01:24:41):
tend to think that like some yeah, some of the
most successful people are people that they get so disconnected
from what they intend to do and when they started,
and so reconnecting. I mean, so much of this, I
guess I tend to see everything through that lens, but
so much of it is about reconnecting that reconnection, that

(01:25:01):
path back home.

Speaker 3 (01:25:02):
I love what you're saying about the iconography and how
the human meshes with the iconography, and you described earlier the.

Speaker 1 (01:25:09):
And maybe everyone does that I just did it in
a bigger sorry decay, it just did in a bigger way,
like you could totally get how like I am Brian Airbnb.

Speaker 2 (01:25:16):
They start to merge.

Speaker 1 (01:25:18):
But be you, even people who don't have a giant company,
who they really are and the person they're like supposed
to be are merging. And as those two things merge,
you lose who you really are.

Speaker 3 (01:25:28):
I mean, it's method acting. It's literally method acting. It's
like we are all pretending to play a role, only
to believe that that role that we pretended to be
is now us and has replaced us. And it's even hard.
I'll tell you why, because when you built Airbnb, it
had iconography. Yes, Brian didn't ever have iconography like, there

(01:25:49):
wasn't a there wasn't like a mission list and a
value list like before when Brian existed before. And so
if you were to draw the iconography of Brian the person,
not the Airbnb, I'm intrigued as to what that would
look like if you started to design that.

Speaker 2 (01:26:08):
I see a child.

Speaker 1 (01:26:10):
I see like a childlike curiosity and energy and love
that I think I've always held on to. I also
see the world like through this idea of family and community.
And I think when people hear the word family think
of like their parents, their siblings, their children. And I

(01:26:32):
think I see like you know, I asked like my
co founder Joe, I asked him, like what would airbnb,
would success be for airbingbe? He had this crazy audacious idea,
he said, to redefine the word family. And I've realized that,
like so much of my life has been trying to
do that. I see this like childlike person of curiosity
and wonder that I've never left that sense of wonder,

(01:26:54):
that I'm open to be vulnerable and guided by love
and like treating wanting to treat those around me like family.
And what I mean by that is I try to
do anything for them. And and I hope, I hope

(01:27:14):
that my friends, if they ever heard this, they would
feel like that resonates. And that's not just a pure ideal,
I mean, that's what I mean, that's the iconography. I
would hope that iconography is true to some extent. I
guess as I think about it even deeper, I've used
the word loneliness, connection and community, but maybe at some
deeper level, the deepest word is family. And what Bond's

(01:27:39):
family is love, and like I think that, like, as
families have gone smaller and smaller, we've gotten more and
more isolated. And if we could re expand that word,
And maybe that's like too idealistic, but like just to
leave in a little bit to your like close friends
and to other people and just try to, like you,

(01:28:00):
expand that circle. That's kind of what I would want.
You know, if I design the world around me, then
I better design it with other people in it.

Speaker 3 (01:28:12):
And as you see that, do you do you see
the child or are you the child as you visualize that?

Speaker 2 (01:28:19):
Yeah, it's funny. I kind of see both.

Speaker 3 (01:28:20):
I see like are you seeing the child sitting there?
Or are you seeing the vision through the eyes of
where you would be.

Speaker 1 (01:28:27):
I feel like a timeless image of myself, like I
might young and old at the same time, Like it's
not just one age. I'm like I can see the
child of me, and I could also see this like
grown up that I always like that is protecting and
so I have like both sides, the protector offering security
and bringing people together and the child who is vulnerable

(01:28:49):
and seeks love and wants to just be open and
totally curious. It's almost like I have this image, you know,
like you're, like you say, at the family, the dinner table,
where you like like you're a kid or your parents,
your siblings or whatever. My image is that, but it's
a very big table with a lot of people, and
you know, and that's not just my close family that

(01:29:13):
I might have. It's you know, maybe like the the
broader people in my life that I have around me.
That's I think the image I have. And I think
that's in a space that's very well designed, very well designed,
and I have a design aesthetic that's like fairly modern
but also whimsical. I don't like the cold. I don't

(01:29:34):
like coldness and modernism. I like it to be like
colorful and so.

Speaker 3 (01:29:38):
Yeah, I saw if you're okay with I want to
show something that came for me to me. The clarity
is that it's not even the merger. Often what you
said so beautifully is like I see my younger self
and I see where I am now, and now it's protecting.
But the childlike is that love, that joy, that community,
the family, and it's like they're hand in hand. Like

(01:30:01):
it's not a merger of the two. It's not an
integration it's a hand in hand.

Speaker 2 (01:30:04):
It's really great.

Speaker 3 (01:30:05):
There's a wisdom that you have today that you didn't
have then, and there's a wisdom you have den that
you don't have now, and it's just hand in hand
and walking together.

Speaker 1 (01:30:12):
I've always wanted to believe that I can have the
wisdom of my grandparents and the curiosity of a child
in one that I have a foot.

Speaker 2 (01:30:20):
You know.

Speaker 1 (01:30:20):
Walt Disney, one of my other idols, used to and
in the front of Disneyland, he says, here you leave
the world of today and into the world of tomorrow,
yesterday and fantasy. He said, I have a foot in
the future and the foot in the past. And I
think that's partly what. I have a foot in the future,
and that future is one of maybe curiosity and looking
forward and futurism and technology, and then I've also a

(01:30:44):
foot in the past.

Speaker 2 (01:30:45):
The foot in the past is my roots.

Speaker 1 (01:30:47):
I think I I oscillate between the two, you know,
culture and technology, massive scale, one of the become one
of the biggest in the world with like they desire
to always be a startup and always be close knit.

Speaker 2 (01:31:03):
It's like these twos.

Speaker 1 (01:31:06):
To paradoxes, competing forces yeah, And I think that that
is a tension that it's I think it's a really
interesting tension. Now you're making me think about all this,
Like I'm sure I've never some of this stuff. I
never really not only I have not talked about it.
Some of the stuff I'm kind of not even really
thought about that until now I'm just really thinking about it.

(01:31:27):
One of the things when you're like you run a
giant companies, you learn scale. When you start a company
you're tiny, you have to do everything you have to
like you know, like things don't even think about. Like
you have an office which is your apartment, and you
need to like buy a coffee maker and go buy
the coffee. And you need to like have a name
for your company. You actually need to check out that
name's trademark, and you got to bun a domain name,

(01:31:49):
and you got to like have a story for the company.
And like then you've got to like make sure you
have a legal corporation. You now found a lawyer. You
got to interview the lawyers, and then you got to
like actually decide where you're going to make and you say,
how do I make things? Like and I could go
down the one hundred thousand things. You're in the tedious details.
And then if you go onto rocket ship that I
go on fifteen years later, you know a billion and
a half times has been used. You end up at

(01:32:12):
some massive scale, a scale that's bigger than you've ever imagined.
But as a founder, you never let go of those details.

Speaker 2 (01:32:20):
You know.

Speaker 1 (01:32:21):
It's like a founder is different than professional manager. A
professional manager never saw it small. And as a founder,
not only did you see it small, you created what
was small. And so as you see the full scale,
you tend to zoom out and zoom in, and zoom
out and zoom in. And it's actually a really helpful
skill in life. Whenever you need a different perspective, you

(01:32:44):
can zoom in or you can zoom out, and I
tend to do both. I go in and sorry, well
what about this? What about this? What about this? And
go into the smaller and small detail, and then I
go back to the present scale. It's like a satellite map,
it's like the powers of ten. Zoom out to space,
zoom in with a microscope, and that is just a
way to think about things. And you were constantly doing

(01:33:08):
that when you run a company. You see the big
picture and you say, what does it mean? You dive
right in and you zoom out, and a lot of
leaders they struggle. They can only do that medium altitude.
They can't see the fullest picture, or they get stuck
and they can't access the smallest of details. In the
entire universe exists in the smallest detail, and that's what

(01:33:29):
you discover when you zoom and zo. You start to
realize the relationships, and it allows you to both run
something large and still connect with somebody at the most
intimate human level and not lose your mind along the way.

Speaker 3 (01:33:41):
Yeah. It's that balance between recognizing what's possible through scale,
but at the same time being able to be embracing
of your own insignificance.

Speaker 2 (01:33:51):
Yeah.

Speaker 3 (01:33:51):
So you see the significance, but yeah you recognize Yeah
it's insignificant.

Speaker 2 (01:33:56):
Yeah. Yeah, it's so fascinating.

Speaker 3 (01:33:58):
Yeah. The paradox is the only thing that's fascinating. Yeah,
you know, the human mind is apparent all of these
Everything that we see that's magical about the world is
a paradox that everything is connected, but everything's doing its
own thing. Yes, right, like the ocean, the sun are
doing their own thing. Yeah, they're connected yet doing their
own thing.

Speaker 1 (01:34:13):
And I think the more you start to see why
I went to scale, you sort of see your right
that more and more things are connected. But because everything
is connected doesn't mean they're all the same. And the
more you learn about the details the things, the more
you realize how different everything is, and so you but
then you realize they're actually in some deeper way related
and that you spend the rest of your life kind
of in that discovery.

Speaker 3 (01:34:35):
Yeah. And you know what I've observed that is the
connecting force, at least up until now in my life,
is that everything that we've just talked about, everything in
the universe that we see is serving uniquely. What connects
it is that it's serving. The sun is serving, the
water is serving, the trees are serving the trunk of
the tree that leaves you talk about the flowers, they're serving.

(01:34:56):
Everything is giving.

Speaker 1 (01:34:57):
A service, Everything is interdependent on everything else. That we
tend to have this illusion that we're separate from one another.
And I think that even like loneliness might be a
reality which is the way you perceive the world, but
a loneness may be an illusion that you're not as

(01:35:19):
alone and separate as you think you are. And I
think that's a really good thing to remind yourself, and
that we are so much more connected to everything else,
and that I think so much of creativity is just
first embracing the fact that everything is connected in some
way and it's your job to discover and make connections
and find relationships and similarities. And by the way, that's
a great way to connect with people to know that, like, wow,

(01:35:40):
what makes them so fascinating is they're really different from
me in some of these ways. But what is going
to bond us is that we're actually so connected and
there are almost no humans on this planet that you
don't have some fundamental connections to and if you don't
see them, you have to keep looking. And once you
keep looking, that becomes the bond, that becomes the thing
that you share between them. How do you do that
with curiosity and interest? Fascinating? Just be fascinated all the time,

(01:36:07):
And it's almost like that's contagious. If you're fascinated, I'm fascinated.
Somebody once said that to me, a director who I
was doing a film too, and he said, if you're fascinated,
I'm fascinated. And I'm like, well, okay, like I really
do and it's like, and so, what what do you
find fascinating?

Speaker 2 (01:36:25):
Yeah?

Speaker 3 (01:36:26):
Yeah, I often de say to people similarly that if
you don't find someone interesting, it's because you're not interested. Yeah,
like you're not interested enough. There is something interesting about.

Speaker 1 (01:36:35):
Something interesting about everyone and everything, and that is what
the curate that is, I think what curiosity is. And like,
you know, you find the game within the game, you
find like in school, Like I think so many people
in school, like they're not interested in subjects because they're abstract.
But if somebody is obsessed with basketball, then teach physics
through basketball, stree biology through basketball, teach history through basketball

(01:36:58):
the history of so you just you find something you're interested.
And I think the great thing about starting a company
is I had no interest in learning about accounting. I
had no abstract interest in learning about leadership and management
and organization. I had no abstract interest in understanding like
technical architecture. But I did interest in how we should
account for all the money we're making, what technology platform

(01:37:19):
we should be on to enable Airbnb, and through something
I was already interested in Airbnb. I was able to
learn all these other things, but if I had to
learn them abstractly, the way we're taught in school, I
don't think anything would have stuck. And so Airbnb became
that model this world. And I have learned almost everything
through this world that I've been generally constructing, co constructing

(01:37:43):
with my coworkers and with the community. And it's just
like I like to joke that Airbnb is like the
world's biggest Risdi project that just never stopped, and we
just kept building it and kept building and kept building
it and kept building it. And as the bigger we build,
the more I learned and the more I discover. And yeah,
I've seen so much of the world through the creation
of this really big house, so to speak.

Speaker 2 (01:38:04):
Yeah, and that's pretty well.

Speaker 1 (01:38:06):
It is pretty well, and it's just getting started.

Speaker 2 (01:38:07):
Hopefully, it's just getting started. Brian.

Speaker 3 (01:38:10):
This is without doubt the most unique episode of On
Purpose I think we've ever heard really in four years.
And I don't just say stuff like that, you can
check with these guys. But we end every episode with
a final five. These are five questions I ask pretty
much ninety percent of them to all guests, and these
are your final five, Brian. They have to be answered

(01:38:32):
in one word to one sentence maximum, and I will
probably destroy that pattern, but we'll try so, Brian, these
are your final five. The first question is what is
the best insight advice that you've ever heard, or received
or read.

Speaker 1 (01:38:47):
It's better to have one hundred people love you than
a million people that just sort of like you, and
so do things that don't scale, and if you do,
maybe people love something you love so much they'll tell
everyone about it and you might end up with millions
of people.

Speaker 2 (01:39:06):
After all. That's kind of a long sentence, but it's
a great sentence.

Speaker 3 (01:39:09):
It's beautiful. It's perfect. Second question, what is the worst
insight advice you've ever heard, read, received, or come.

Speaker 1 (01:39:17):
Across anything that involves chasing status? Not because it's bad,
but because it's actually a horrible way to even get it.

Speaker 3 (01:39:26):
Love that answer, yeah. Question number three, how would you
define your current purpose.

Speaker 1 (01:39:32):
To try to help bring the world together, even if
it's in the end a small way?

Speaker 3 (01:39:38):
Question number four, if you were being remembered after you
were physically gone, what would you hope to hear.

Speaker 2 (01:39:47):
We miss them?

Speaker 3 (01:39:49):
A fifth and final question. I asked this question to
every guest who's ever been on the show. If you
could create one law that everyone in the world had
to follow. What would it be?

Speaker 1 (01:39:58):
Sometimes people ask me, impose one thing on the world
would it be? And I'd say, everyone would have a
passport and everyone would walk in.

Speaker 2 (01:40:05):
Someone else's shoes.

Speaker 1 (01:40:06):
And I think if they were to do that, there'd
be like such a greater awakening in the world. So
maybe everyone was forced to live someone else's life and
to step in someone else's shoes, and the more different
the better.

Speaker 3 (01:40:22):
Well, said Brian Tesca. Everyone, Brian, that was, as I said,
the most unique. I think it's really interesting something that
came to my mind and heart. And since this has
been such an intuitive conversation, I feel I should share it.
You know, in our professional life, we have business partners,
but in our personal life, I don't think we often
think about having human partners. And I really appreciate you

(01:40:44):
dancing with me today, going there with me today, and
being human partners for each other. And you definitely did
that for me today. You brought out of me things
I didn't know that I haven't gone to for a while.
So thank you so much for inspiring me enlightening me
in so many ways. I actually had a special internal
experience myself.

Speaker 1 (01:41:03):
Well, I think I've learned about myself through this process.
It's amazing the amount of time you can go through
in your life without stopping and taking a look at things.
And when you do, my God, like that just changes
your perspective on everything, doesn't it.

Speaker 3 (01:41:19):
Absolutely, thank you so much, Thank you, grateful for you.

Speaker 2 (01:41:22):
I think you have me to thank you so much.

Speaker 3 (01:41:24):
Set your honor such a pleasure. And everyone who's been
listening and watching. If you're with us, then make sure
that you I want you to let me know what
was your favorite moment. There are so many great moments,
but grab a screenshot of where you found your favorite moments.
We can see all the seconds and minutes so that
everyone can go listen to it. I love seeing what
deeply connects and penetrates through to our community because this

(01:41:46):
is all in service of you. So thank you for
everyone who's been listening and watching, And thank you Brian,
thank you jam. If you love this episode, you will
also love my interview with Charles Douhig on how to
hack your brain change any habit effortlessly, and the secret
to making better decisions.

Speaker 1 (01:42:03):
Look, am I hesitating on this because I'm scared of
making the choice. Because I'm scared of doing the work,
or am I sitting with this because it just doesn't
feel right yet

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Host

Jay Shetty

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On Purpose with Jay Shetty

Stuff You Should Know

Dateline NBC

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Brian Chesky ON: The Crisis of Disconnection and Loneliness & How to Tap Into Your Creative Potential