Brian Chesky’s new playbook
By Lenny's Podcast
Summary
## Key takeaways - **CEOs should be Chief Product Officers**: The CEO of a product or tech company should essentially act as the Chief Product Officer. If the CEO isn't the CPO, it raises questions about whether the company is truly product-led. [16:41], [16:49] - **Product development needs integrated marketing**: You can't build a successful product without knowing how to market it. If a product is well-made but has no distribution plan or way to communicate its value, it's as if it was never built. [08:09], [08:14] - **Embrace details, avoid micromanagement**: Being in the details is crucial for leadership, distinguishing itself from micromanagement. Leaders must understand the details to effectively assess performance and guide their teams. [00:35], [00:42] - **Functional model beats divisional silos**: Moving away from divisional structures towards a functional model, like that of a startup, fosters better collaboration. This integrates functions such as design, engineering, and marketing, preventing teams from operating in separate universes. [25:53], [26:02] - **Guest favorites blend uniqueness with reliability**: Airbnb's 'Guest Favorites' feature aims to combine the platform's unique offerings with the reliability expected from hotels. This collection identifies the top two million most-loved homes based on extensive review data. [40:09], [40:24] - **Ambitious goals foster different thinking**: Setting 10x goals encourages teams to break down problems and think differently, moving beyond current processes. This approach, rooted in first-principle thinking, helps overcome challenges by forcing a deeper understanding. [47:04], [47:15]
Topics Covered
- Airbnb's product management reinvention: Smaller, senior, combined.
- Product-led growth: Build great, then tell the story.
- Delegating product makes companies slower, not faster.
- Leaders are in the details, not micromanaging.
- Add a zero: Push teams to rethink problems.
Full Transcript
way too many Founders apologize for how
they want to run the company they find
some midpoint between how they want to
run a company and how the people they
lead want to run the company that's a
good way to make everyone miserable
because what everyone really wants is
Clarity what everyone really wants is to
be able to row in the same direction
really quickly and so I basically got
involved in every single detail and I
basically told leaders that leaders are
in the details and there's this negative
term called micromanagement I think
there's a difference between
micromanagement which is like telling
people exactly what to do and being in
the details being in the details is what
every responsible company's board does
to the CEO it doesn't mean the board is
telling them what to do but if you don't
know the details how do you know people
are doing a good job people think that
great leader job is to like hire people
and and just Empower them to do a good
job well how do you know they're doing a
good job if you're not in the details
and so I made sure I was in the details
and we really drove the
product
today my guest is Brian chesy Brian is
the CEO and co-founder of Airbnb which
he started in his apartment with his
co-founders Joe Nate and has turned into
an80 billion Global business with
Travelers and homes in 220 countries I
was very lucky to get to work with Brian
for many years and my sense is if you
ask people who they consider the most
inspiring Tech or Business Leaders today
Brian would be right near the top of
that list in our conversation Brian
shares an depth explanation of what's
happening with product management at
Airbnb which caused quite a stir in the
product world when he talked about this
previously we also get deep into Brian's
new approach of how he runs Airbnb
including shifting away from traditional
growth channels like paid growth and
instead betting that if they just build
the best possible product and tell
people about it growth will happen also
how the product team now operates
including having just one single road
map across the entire company and Brian
staying very close to every design and
every feature we also get a bit into his
personal life including how he finds
balance and avoids burnout how he
continues to learn himself so that he
can stay ahead of the business and its
growth this is a very special episode
for me and I'm thrilled to bring you
Brian chesy after a short word from our
sponsors this episode is brought to you
by sidebar are you looking to land your
next big career move or start your own
thing one of the most effective ways to
create a big leap in your career and
something that worked really well for me
a few years ago is to create a personal
board of directors a trusted peer group
where you can discuss challenges you're
having get career advice and just kind
of gut check how you're thinking about
your work your career and your life this
has been a big trajectory changer for me
but it's hard to build this trusted
group with sidebar senior leaders are
matched with highly vetted private
supportive peer groups to lean on for
unbiased opinions diverse perspectives
and raw feedback everyone has their own
zone of Genius so together we're better
prepared to to navigate professional
pitfalls leading to more responsibility
faster promotions and bigger impact
Guided by worldclass programming and
facilitation sidebar enables you to get
focused tactical feedback at every step
of your journey if you're a listener of
this podcast you're likely already
driven and committed to growth a sidebar
personal board of directors is the
missing piece to catalyze that Journey
why spent a decade finding your people
when you can meet them at sidebar today
jump the growing weight list of
thousands of leaders from Top Tech
companies by visiting sidebar. comom
Lenny to learn more that's sidebar.
comom
Lenny you fell in love with building
products for a reason but sometimes the
day-to-day reality is a little different
than you imagined instead of dreaming up
Big Ideas talking to customers and
crafting a strategy you're drowning in
spreadsheets and road map updates and
you're spending your days basically
putting out fires a better way is
possible introducing jira product
discovery the new prioritization and
Road mapping tool built for product
teams by atlassian with Juro product
Discovery you can gather all your
product ideas and insights in one place
and prioritize confidently finally
replacing those endless spreadsheets
create and share custom product road
maps with any stakeholder in seconds and
it's all built on jira where your
engineering team is already working so
true collaboration is finally possible
great products are built by great teams
not just Engineers sales support
leadership even Greg from Finance anyone
that you want can contribute ideas
feedback and insights in Juro product
Discovery for free no catch and it's
only $10 a month for you say goodbye to
your spreadsheets and The NeverEnding
alignment efforts the old way of doing
product management is over ReDiscover
what's possible with Jiro product
Discovery try it for free at atlassian
Brian thank you so much for being here
welcome to the podcast well thank you
for having me did you ever think when I
left airbeam be one that I would have a
podcast and two that you would be on my
podcast I had no idea you would become a
podcast host and that you would have
such sucessful podcast yeah congrats on
everything it is awesome I appreciate it
congrats to you too Brian things seem to
be going great I'm excited that you're
here I want to start with the elephant
in the room for a lot of listeners of
this podcast uh what is going on with
product management at Airbnb you made
some comments at figma config and a lot
of people got this impression that you
eliminated product management Airbnb and
I've heard from a lot of product execs
having boardroom conversations as a
result of that and they were trying to
decide should we remove product
management from the company should we
significantly cut product management so
I'm just curious to hear from you what
is the latest on your thinking on
product management and what's happening
with product management at Airbnb I
spoke at figma you know like four or
five months ago
I spoke to a room of designers I then uh
got off stage I saw people somebody
tweet that said something to the nature
of that I said I got rid of the product
management function all the desires room
started shearing that's right so I want
to I want to I want to talk about two
things what I actually meant because I
didn't actually get rid of the people
and also why do the people in the room
cheer because that's also like a thing
we should ask ourselves I hope everyone
listening to this podcast should
understand where did that place come
from that 5,000 designers in the room
cheered because I thought I eliminated
the existence of a function because if I
said I eliminated the engineering
function no one would have cheered it
was specifically that function so I want
to talk about what that might mean it
wasn't the people it's the way they're
working together so we don't have any
longer the traditional product
management function as it existed with
when you were Z but we didn't get rid of
people helping Drive the product what we
did
is we combined what one might call the
inbound product development
responsibilities of product manager with
the outbound or marketing
responsibilities of product marketing
that's the first thing we did the second
thing we did is we offboard much of the
program management functions that
product managers may do to actual
program managers a lot of people the
product management title are actually
program managers so we actually started
offboarding some responsibilities to
program management the last thing we did
is we made the group smaller and more
senior so we don't really have a lot of
Junior product marketers so the most
senior people are called Product
marketers but everyone has to understand
how to talk about the product so the
basic idea is this you can't build a
product unless you know how to talk
about the product you can't be an expert
in making the product unless you're also
an expert in the market of it and a lot
of companies what they do is they ship a
product it doesn't work and they say we
tried that it didn't work and if you say
you tried it didn't work my question is
was it a bad product a bad strategy or
bad execution maybe it was a really
well-made product but you had no
distribution plan you had no way to talk
about the product if you build a great
product and no one knows about it did
you even build a product so that is
essentially what we do we have a much
smaller function the people are much
more senior they have much more
responsibility the other thing though is
that they do not control or drive
designing or engineering we are a very
purely functional model they manage by
influence do not have
control now you might ask like how does
that work in a company where people can
only manage by influence here's the
amazing thing we built and designed a
company where you can manage by
influence and no one has to like you you
don't actually have to have to win
people over oh and last thing I want to
say is why did 5,000 designers Shear
when the people thought I removed the
product management function because I
want to say I I don't I don't know if I
can speak on behalf of all the designers
but having talked to live designers I
think designers and the valley are very
very frustrated with the product
development process not to say the
product managers but they're extremely
um frustrated and I think a lot of
designers feel like they're compromising
many designers I know heads of design
well-known heads of design I told them
they're not designers they're design
administrators they're running a design
service organization because Silicon
Valley often treats design as a service
organization you know like design is
catching things before it Go outs the
door it's not actually typically part of
the develop process and I think this is
not just bad for design I think it's bad
for product managers and Engineers
because we all want to build the best
products and one day you wake up and a
variety of phenomenon might have
happened and if people are watching this
from a large company here might be some
of the characteristics the first thing
you notice is that these different
groups might be running on slightly
different technical Stacks that's the
first problem and they may actually be
require accumulating technical debt the
next problem you'll see is that there's
a lot of dependencies so five teams are
going s different directions but they
all need a payment platform and so that
on it happens is that the teams that
everyone's dependent on get this backup
like a deli and people are going around
the block and then they are basically
like at some point they just kind of
give up so then the teams that are
dependent on other people say give me
the resources I'll build this group
myself so instead of five teams going to
marketing to get a campaign or to
leverage some service they start
building their own marketing departments
own groups so now they're really
becoming separate divisions and this is
where division comes from now once you
have a division your division is as
successful as you are a priority so now
you have to advocate for your division
so there's a lot of advocacy if you have
dependencies you've got to persuade
people by building relationships and so
the people that are like that build the
best relationships are the ones that get
the most resources and that creates what
we call politics it's so now politics
that brw in the company and
suddenly people get more subdivided more
subdivided subdivided and that creates
another problem which we call
bureaucracy and that bureaucracy means
it's hard to know who is doing what you
can't like people are going in different
directions and that creates a lack of
accountability when there's lack of
accountability then there's a sense that
what I do doesn't matter and that
creates complacency and then suddenly a
fast growing company becomes a big slow
moving bureaucracy this is a general Arc
winds up happening and then you end up
having this situation where company's
done like 10 marketing efforts but no
customers heard anything they have
thousands of Engineers they shipped all
these products but a customer can't tell
you a single thing you did and you know
marketing and Engineering like don't
talk to each other it's not even they
hate each other they're like in
different universes I've always said
that the health of an organization one
simple horis is how Coast's engineering
and marketing and marketing is a lot of
companies are like the waiters Engineers
are like the chefs and the chefs yell at
the waiters they go in the kitchen in
fact the waiters are the ones talking to
the customers all day and they also know
how to sell things so you really want
them being enjoined at the hip and you
want Engineers to be thinking about
maybe had to talk about the products
that they're building so this is the
problem that we had and I also the other
thing we were doing is as you know Lenny
we're spending a lot of money in
Performance Marketing I don't think
Performance Marketing is a bad thing I
think Performance Marketing a laser uh
actually my co-founder who obviously
know well Joe used to have this metaphor
of lasers flash bulbs and chandeliers if
you want to light up a room performance
marking is a laser it can light up a
corner of a room you don't want to use a
bunch of lasers to light up an entire
room you should use a chandelier and
that's what brand marketing is but if
you do need to laser in in Balance
supply and demand then Performance
Marketing is really good it literally
lasers in Performance Marketing though
doesn't create very good accumulating
advantages because it's not an
investment now if you want to build it
permanently like booking.com if you have
a really highi now you can have a
Performance Marketing Arbitrage business
but assuming you don't want a Arbitrage
business you actually need to be
investing and so we think of marketing
as education that we're educating people
on the unique benefits so a lot of
companies don't do product marketing
they do brand marketing which are ads
about the app or they do Performance
Marketing but they're never really
educating people about new things
they're making and shipping and because
no one's marketing new things they
shipping there's no purpose to ship new
things because you ship new things and
people don't know about them or use them
or they're not educated and so you try
these big new things people don't adopt
them immediately so then you get more
and more
incremental now what we do is we do we
have a rolling two-year road map we
don't even really do an annual plan I
mean we as you remember Lenny you're at
Airbnb we would have like three-month
planning Cycles now planning cycle is
just a budgeting cycle and it's like
most people only spend a week or two on
it some don't spell any time on it and
we have a rolling two-year product plan
the strategy product strategy road map
that gets updated every six months with
releases we release products um every
May and every November or October
obviously we did one today we can talk
about and the entire company works
together they Row in the same direction
and the product management also does the
product marketing so they're figuring
how people are going to learn about it
they're doing the demos they're
understanding the story the videos
they're you know figuring out all the
customer touch points making sure
everyone understands it our product
marketing works with Communications we
like work months ahead of time on all
the different assets and when we're
working at a launch one of the first
things we'll do is start figuring out
what the story is and the story will
often dictate the product because
ultimately you have to tell a story to
people but a story also is a really
helpful way to develop a cohesive
product right we wanted a company where
a thousand people could work but it'll
look like 10 people did it and so sorry
that was a bit of a brain dumb but that
is a little bit of a universal theory
for how we develop products now I I
could go into a lot more detail but I
probably will'll stop there that was
amazing you touched on all of the things
I want to talk about so I'm gonna oh
geez so we can go deeper and deeper
because the rabbit exactly exactly so
I'm going to pull on a couple threads
the first is this idea of a single road
map you talked about and what this
reminds me of is I was talking to
another very prominent CE of a public
company and he pointed out that there's
this cycle that he sees a lot of
Founders go through where they initially
run the show they're in charge they tell
people what to build and then over time
they're encouraged to delegate and to
empower and it leads to a bunch of
optimization work and small thinking
maybe and you talked about bureaucracy
in politics and then eventually you
realize I need to take the RS again and
drive the ship and kind of Take Back
Control of what's happening and it feels
like you went on that Journey that's
exactly how it went and that's how it
goes almost at every company I've heard
of by the way I think that like many
years ago I remember I think reading a
blog post by Ben Horowitz saying that a
lot of people tell product Le Founders
or engineering Le Founders to step away
and delegate their product to other
people but suddenly they delegated away
the thing they're best at the thing that
is hardest for them to replace so we
don't have a chief product officer title
but if we had one it would be me you
know they they I wouldn't have a chief
product officer I think the CEO should
be basically the chief product officer
of a product OR tech company and the CEO
is not the chief product officer then I
don't know if they're a product or
tech-led company maybe maybe that's okay
if they're an Ops company or if they're
a marketing company or if they're like
not a tech company at all but ultimately
I think the founder CEO should be that
person so when we were starting Airbnb
it was probably the three of us you know
as you know like I think Airbnb was a
unique situation where it was three of
us I don't think any of us was that
dominant I probably played the closest
thing to the role of the the people
listening like the closest thing to the
role of the product manager but again I
did marketing I did design I did like
Ops I did like kind of a little bit of
everything so I was basically everything
but engineering and then as we grew I
started getting more and more hands off
in the product and I always remember
Lenny when you this there was this
Paradox where the less involved I was in
a project I mean there was there they be
clear there were times I inserted myself
and dysfunction occurred that is
absolutely true and that was just a
learning experience for me but there's
this other scenario where the less
involved I was in the project the more
spin there was the less clear the goals
the less advocacy the team had the less
resources the fewer resources they had
and then therefore the slower they moved
and the slower they moved the more they
assumed was because I was too involved
right because people assume that that
our natural equilibriums to move fast
moving slow it's because of an over
involvement in leadership and therefore
I would get less involved I would give
teams more control I would give them
teams more empowerment and the more I
kept giving people what they asked for
initially they may have been happy but
the outcome of it was always it seemed
weirdly like they got less of what they
wanted they wanted to move faster so I'd
power them and they'd move slower and
again how that happened is what I
described that you you you end up in a
situation where you're delegating down
so I think that things were getting
worse and slower and slower and slower
2015 2016 2017 2018
2019 and by
2019 we were spending a billion dollars
on AdWords we weren't really like
investing in the brand we're doing a
huge amount of AB testing I think AB
testing is important in in times but
like let me actually let me let me let
me let me clarify you be testing we
don't test blue versus green we have a
control and a treatment like I think we
did with ere so we have a design we
might do a hold back occasionally to see
how the thing is working but if we do an
AB test there has to be a hypothesis if
we don't have a hypothesis and a is
better than b then we're stuck with b
and that's like a really really big
problem but never you can never change
it and imagine 10 teams doing AB testing
and like imagine if you designed
software the way designed a house or
designed house the way design software
and we AB test a sofa and we said like
well how does a sofa work and it seems
like with this sofa that we've AB tested
people spend more time in the living
room so therefore like people are going
like this room better but actually the
sofa has a relationship to the end
stands which have relationship to the
lamps which have relationship to the
carpet or the rug which have
relationship to the television which
have relationship to the house and
everything else so you have to think
about the whole cohesive system and I
started realizing that I remember
working with as I asked one person on
your team somebody you know well and I
asked him I said why is our I feel like
I open our app and the product hasn't
changed in like four years I remember
saying this like 2018 2019 and he this
person described that you know well as
just the way we were doing things the
initial way we were doing things to move
fast had made us move slow
so we end up doing is it was now late
2019 I don't know what to do I'm like
the product is slow the app seems not
change cost are rising I keep adding
more people there seems to be more like
politics by politics I mean advocating
for like individual interests rather the
whole of the company more bureaucracy
meaning like meetings about meetings
about meetings and a lot of dependencies
people were describing working 80 hours
and getting 20 hours of productive work
done which is like just like a crazy
ratio a week and I didn't really quite
know what to do and then right before
the pandemic I meet two people that
really affected how I thought about
things the first was heroki asai heroi
now works at Airbnb he's one of my
Executives and actually product design
product marketing design and marketing
repor to him and he was a creative
director for Apple so he worked for
Steve Jobs was like basically dotted
line to Steve for many many years came
from graphic design eventually ran all
of marketing Communications and apple
marketing Communications they actually
like they actually designed the app they
made the app they designed like all the
marketing touch points for the store
right so it wasn't just ads it was like
every brand touch point they were
responsible so everything flowed through
marketing and so marketing became the
governing factor that made everything
really organized I met another person or
I got reacquainted a person named Johnny
IV and Johnny I was the head of
industrial design then Chief design
offic or apple and they described this
way of running a company that was
totally different than the way that I
was running it it was basically the way
that Steve Jobs ran Apple from about
1998 till he died in 2011 Apple somewhat
runs it this way today but they are semi
like the services is turning into
Division and they are just so big that I
think it's you know not a oneto one
anymore but they are still technically
run this way and I had this image of not
being divisional because we were running
like we 10 divisions we had a flights
Division and you know we had a homes
division which was divided to proost and
core host and Lux and we had business
travel and we had like you know a
magazine and we had experiences and we
had.org and we had china we had like
these 10 different divisions all going
in 10 different directions and I created
this culture where everyone want to be a
business manager and or a know business
leader general manager which made them
want to create many general managers
right and so the company kept getting
subdivided subdivided subdivided and
that made it very very difficult turn
and this was all about me delegating
responsibility the problem is if you're
running a divisional company you're a
product Leed founder you're kind of what
are you doing like strategy Capital
allocation my job went from proactive to
very reactive I was reacting to a lot of
things I was in a lot of meetings try to
adjudicate different issues between
groups so then the pandemic occurs and I
had this image on mind it's like I have
this dream that I could run a company
much more like a startup I remember
going on a walk with Joe and Nate and
bolus it was October
2019 and I told them I had this dream
that I left the
company 10 years ago and you they just
asked me to come back and I said I was
horrified at what I
found and they said well what did you
find I said I found a company that on
the one hand had amazing culture and
people with a great Mission with a brand
people really
loved but the we lost our design
routes you know we weren't investing in
the long term we were obsessing over
hitting metrics we didn't actually have
any cohesive understanding of what we
were doing it was really hard to get
work done a lot of the great people were
leaving and cost was rising and both
growth are slowing and that was exactly
kind of what was happening and then the
pandemic occurred and we lost 80% of our
business in8 weeks and then suddenly
we're like oh my God like I remember
having basically staring into the abyss
and luckily I've never had a near-death
experience but the way it's been
described to me is it's like your flly
flashes before you your eyes and you
have Clarity and that's what happened to
our business we had a near-death
business experience and our business
flashed before our eyes and so suddenly
I basically got into action and I said
I'm going to run it this other way where
I'm going to get back and evolved in the
details and by the way Lenny here's the
funny thing before the crisis a lot of
people felt like I was too involved in
different areas once the crisis happened
guess what happened people are like what
do we do we need you more involved and
so I got more involved and when I got
involved I made the following changes
the first thing I did is I took like I
said everything we're doing has to be
written down and put into Google Google
like a Google sheet it turns out people
couldn't even write down everything they
were doing I remember one person told me
you you think we're doing too many
things for me to ever be able to
document I'm like what but anyways we
have eventually got everyone to write
everything down and I said okay we can
do about 20% of these things and so if
everyone says oh I might it be simple
I'm only doing three things yes but
you're one of like a thousand people so
actually we're doing 3,000 things so
instead of one team doing three things
three teams should do one thing so we
totally cut down the number of projects
we removed layers of management I wanted
to be as few layers as possible from the
leaders of the team we went to a
functional model we went back to a
startups so we said we're not going to
have divisional leaders we're going to
have design engineering product and
which turned to product marketing and
marketing and Communications and sales
and operations all the functions of a
startup I said we're goingon to have
fewer employees we're gonna have fewer
more senior people there's a great
saying that the best way to slow a
project down is to add more people to it
and so we felt like very few employees
we have fewer than 7,000 employees today
as a relative comparison I think Uber
has 30,000 and it's not to say they're
big it's just to say that's how small we
are and we've really benefited from
having not a lot of employees so we had
we made sure that every executive was an
expert in their functional domain so you
know how there's a lot of engineering
managers that aren't that technical or
maybe not a lot but they exist or
there's designers but there's design
leaders who who lead the people a design
leaders job should be managing the
design first the people second that's
Johnny did or like they're they're
interchangeable I I could never imagine
Johnny AV at Apple just being a manager
of people he was looking and designing
the work with the team how do you manage
the people without managing their work
how do you give them development if
you're not in the details with them on
the work so the same thing is true so
people had to be experts everyone had to
be an expert I stopped pushing
decision-making down I pulled it in I
created one shared Consciousness and I
said the top 30 40 people in the company
are going to have one continuous
conversation metrics are going to be
subordinate to the calendar so we're
going to have a road map it's going to
be a two-year road map well update the
road map literally every month people
may Wonder well like what if the world
changes yeah it changes every day so the
road map's something where the next
month hasn't changed but two years out
it changes it's a rolling road map and
by the way if Ukraine like gets invaded
and you want to like provide housing for
refugees you can still pivot people and
adapt very quickly we house 12 12,000
refugees so you still keep a reserve of
resources to be able to Pivot and do
things because there's always unexpected
events I created this new function
called product marketing we basically
describe what that is I made the group
much smaller I took a lot of product
managers I reassign as program managers
I had many of them trained an actual
program management because their roles
got much bigger um program management
airb is a high status job a lot of
companies it's like a coordination job
and me we said because we're going to do
launches it's high status we said we're
going to do two launches a year and you
can't ship something unless it's on the
road map so every single thing in the
company with the exception of some
infrastructure projects have have to be
on the road map and then I'm going to
review all the work and so we create the
CEO review schedule where I said I'm
getting back in the involved in the
project and I'm going to design I'm
going to review all the product and all
the marketing so every project I would
do review either every week every two
weeks every four weeks every eight weeks
or every 12 weeks there'd be a Cadence
and then I had a p program manager that
would score all the projects either
they're green yellow or red mean they're
on track or not on track to ship whether
we thought they were work we don't know
until after we ship it but I use the
reviews of the work every single week
and the reason there's not a lot of
bureaucracy and the reason you don't
need any influence at Airbnb is I'd
review the work and if something wasn't
happening then I would like stop the
meeting and say why isn't this happening
and like we would all get together and
so you couldn't have a situation where
like a team wouldn't collaborate and so
it would be like I could then feel the
work of an of an individual engineer cuz
imagine it's like we're a car company
and I I see the car prototype every week
and I notice there's a there's a there's
a something about the tires off now I I
can identify the individual person who
was blocked so every week I would see I
would try to see the equivalent of at
least a semi assembly of the entire new
product we were working on which allowed
me to identify with teams the different
bottlenecks happening in the company and
the reviews were the thing that allowed
us to dictate the pace and so because we
had unal we all these reviews I didn't
need to mandate people going back to an
office I didn't really care where they
worked because I could track how well
they were working because of the review
cycle I it's so these were these were
like some of the changes that we made we
also started really building out much
more of a marketing Communications and
creative function we built out our own
in-house creative agency so we use
production Partners but we don't use
widening kendi or Sher or any those
anymore we actually build our own
in-house agency so to speak which is a
creative group The Creative Group does a
lot of the the the not just the ads but
the creative on the product so we got
really really functional we got rid of a
function called ux writing and we
combined it with marketing writing we
said wait aren't the best writers like
why don't we just have the best writers
do everything why is ux writing a
separate function because actually the
emails the app the ads should all be one
voice now there may be people that come
from a different background like there
are people that come from ux but they
all roll up to one function of writing
and writing should not go to design
writing should go to a function called
writing unless you want your head of
writing to report to design then that
doesn't make sense so we we we really
make made a lot of those changes just to
round up the question that you asked I
think that like way too many Founders
apologize for how they want to run the
company I don't know why they do but I
think they apologize for how they want
run a company they basically find some
midpoint between how they want to run a
company and how the people they lead
want to run the company if you're a
Founder what I would tell you is the
problem with finding a negotiation
between how you want to run the company
the people you want is that's a good way
to make everyone miserable because what
everyone really wants is Clarity what
everyone really wants is to be able to
row in the same direction really quickly
and also if you try to appease employees
they may not even be there for the whole
time so we have entire project the
company where somebody advocated to do
it it was a big commitment and then they
left and now we're still doing the
project they advocated for so it really
has to be something that everyone wants
to sign up for not just the person who's
there because they might not always be
there and so you know I basically got
involved in every single detail and I
basically told leaders that leaders are
in the details and there's this negative
term called micromanagement and I think
I think there's a difference between
micromanagement which is like telling
people exactly what to do and being in
the details being the details is what
every responsible company's board does
to the CEO it doesn't mean the board is
telling them what to do but if you don't
know the details how do you know people
are doing a good job people think that
great leader job is to like hire people
and and just Empower them to do a good
job well how do you know they're doing a
good job if you're not the details and
so I made sure I was in the details and
we really drove the product
this episode is brought to you by EPO
EPO is a Next Generation AB testing and
feature management platform built by
alums of Airbnb and snowflake for modern
growth teams companies like twitch Muro
clickup and DraftKings r on EPO to power
their experiments experimentation is
increasingly essential for driving
growth and for understanding the
performance of new features and EPO
helps you increase experimentation
velocity while unlocking rigorous deep
analysis in a way that no other
commercial tool does when I was at
Airbnb one of the things that I loved
most was our experimentation platform
where I could set up experiments easily
troubleshoot issues and analyze
performance all on my own EPO does all
that and more with Advanced statistical
methods that can help you shave weeks
off experiment time and accessible UI
for diving deeper into performance and
out of the box reporting that helps you
avoid annoying prolonged analytic Cycles
Appo also makes it easy for you to share
experiment insights with your team
sparking new ideas for the AB testing
flywheel EPO Powers experimentation
across every use case including product
growth machine learning monetization and
email marketing check out EPO at geo.com
Lenny and 10x your experiment velocity
that's
geo.com
Lenny you guys found such a unique way
of working I've never heard of a company
working in these ways and so many
contrarian ways I think it's going to be
a really interesting case study as
things progress essentially what you
done is shut down traditional growth
channels or at least limited them PID
growth and maybe SEO maybe referrals at
least for a while and you've kind of
shifted to let's just make an awesome
product and tell people about it and our
bet is that what's going to grow do you
feel like this can work for most other
products or is there is like a consumer
specific opportunity what advice would
you give to Founders that are thinking
about man we should try something like
this I think that this methodology can
work for everyone but I don't think you
have to be as ideal logical or have to
go all the way to 100 you I still think
growth channels matter to be clear we
still spend money on Performance
Marketing we still do measure conversion
and we will do some experiments think of
conversion and growth optimization as
like running a football down a field and
think of these big like leaps as passive
you should probably be doing 80% passes
20% running the ball down the field and
a lot of companies they do 80% running
down the ball down the field versus in
20% passes so I think that this
methodology will work for everyone I
mean here are the things I believe I'll
give you a checklist number one I think
that the CEO unless they're not a
product person should think of
themselves that this cheap product
officer and they should be involved in
the product number two if you're not
functional I would at least think about
everyone being really close together so
here's another way saying it Lenny every
product manager should be interconnected
and know what everyone else is doing
they shouldn't be independent siloed
unless they really are running like
separate companies or separate orgs and
they have no dependencies I think that
every leader should be an expert in what
they're leading there should be no
people managers in the entire company
and when I say people managers meaning
your only responsibility is people not
the work or not the domain because you
can't manage people the void of their
work you know imagine like a fire chief
they don't know anything about like
putting out fires like that's crazy like
you have to know the subject matter
people should aim to have as few people
as possible on their team I'm not saying
eliminate people I mean grow slowly and
do not be
Reckless five teams should do one thing
rather than one team do five things so
that's just a metaphor but people should
work together I think that people should
consider doing launches you can by the
way ship every hour of every day but
then package it and tell a story if you
want to hold the product back I think
that team should use data but they
should also use research and intuition
there's a designer called Charles em and
said you can't delegate understanding if
you're going to do ab experiments or
measure data you have to understand what
it means I think that you have to have
an intuition intuition comes not from
arbitrariness it comes from
understanding I would make sure that you
have engineering and design ideally
report to the founder product-led person
I would not have design under product
unless you have an extremely good reason
the product person kind of is a designer
I would TR to think about product
management expanding the
responsibility and including
distribution understanding the customer
and teaching people how to tell a story
I would try to make sure that the
product managers are a combination of
Art and Science I do not think you want
purely technical product managers doing
things if they're going to work with not
technical functions right if they're
only work technical functions that's
fine but they don't work at
non-technical functions I think that's a
problem I should make sure that
marketing and engineering are
interconnected I would make sure that
you have as few layers between a CEO and
other people if you're a CEO every
direct to your direct should be a
implicit DOA line to you so I treat
every direct to my direct as if they're
a direct report a DOA line I don't try
to conflict with the direction of my
team but I always want to know what
another layer below me is doing I think
you should think of each release as a
chapter of a story or like an episode of
TV series and you should think of your
company in a five or 10 year story you
may not know where you are in 10 years
but you're telling this ongoing story
and most of all I would say that
everyone should Row in the same
direction if there's only one thing I
said in this interview today which I'm
not sure what it would be but I I I
think a good candidate is try to get
everyone to row together in the same
direction otherwise why the hell are you
all in the same
company speaking of rowing in the same
direction you had a huge launch today I
know you wanted to talk about it your
winter release and it kind of is the
culmination of lot of the things you're
talking about I'd love to hear just some
of the stuff you're launching let me
just back up seleni so you know this
problem really like well one of the best
things of Airbnb is that we're this
marketplace where guest and host come
together and we have all this unique
inventory and people you know list on
Airbnb and every home is one of a kind
and we have seven million homes and
there's all this surprise and all this
delight the problem is that every home
is one of a kind and you often don't
know what you're going to get and so
a lot of guests have described checking
into Airbnb as a Moment of Truth where
when you open the door that you know the
home you find out if the home is exactly
the home that you booked and this turns
out to be a big problem for people
wanting to book an Airbnb and when we
survey guests or people who don't use
Airbnb the number one re the hotels are
not as special they're not as unique but
the advantage they have is you know what
you're going to get you know exactly
you're going to get and so what we found
is that reliability is airb be's
Achilles heel or at least it has been
that you know with hotels you know
you're going to get an Airbnb you don't
always know you're going to get and so
we asked ourselves what if we could
combine the uniqueness of Airbnb with
the reliability that you've come to
speca hotel and that's what we've done
with guest favorites guest favorites are
you know homes that guests in our
community love the most we took 370
million reviews on Airbnb plus millions
of customer service tickets plus all the
host cancellation data and we use all
the signal to create the top two million
homes that this collection of two
million homes that we call guest
favorites because the homes the guest
rate the highest we
think combine the uniqueness of Airbnb
with the reliability to come to expect
hotel and I can't imagine there's a lot
of use cases where you wouldn't want to
book a guest favorite we think that's
also part of this broader system of
readings and reviews you see as you know
Airbnb is built on a system system of
trust and we invented this new way for
people to trust one another you know at
least at scale you know through through
through living together certainly and we
felt like the rating and review system
could use a little bit of an upgrade so
we obviously made some upgrades to
ratings and reviews and the final thing
and this brings up another point I might
bring up is we've completely overhauled
the host tab so you know one of the most
important things when you get to an
Airbnb is the listing is accurate but
the problem is that a lot of host
listings don't have all the details up
to up to date so they might not like
describe perfectly their listing they
might not have filled up their amenities
they might not have a photo tour and the
reason why as we're doing research is
because they found it was hard to manage
their listing and it was hard to manage
their listing because was designed as
this hodg Podge Thing by different teams
over many years oh here's the other
thing Lenny when you were at Airbnb we
had a guest team and a host team we
don't have a guest team and host team we
have a design team we have a marketing
team we have an engine engineering team
the reason we don't break the app into
guest and host anymore is because
reviews affect guest and host it turns
out that almost everything involves
connecting the guest and host and you
have separate teams that tend to have
separate road maps that go in separate
directions they become incompatible so
we have product marketers that
responsible guest and host things but
there's the the designers are in the
engineers are fairly fungible and they
can move from Project to project and
then we keep some people especially the
product marketing people on a domain
area but we really want to make sure
that we have designers and Engineers
covering a much larger surface and so so
that's what we did we have this
incredible new tab called the listing
tab that we designed it's quite possibly
one of the nicest things we ever
designed if you go to my Twitter account
you'll see a little Sizzle reel from
some of the design we've done by the way
the design is a whole new aesthetic I'd
like to like make the announcement that
I think flat design is over or ending
you know I think if you remember the
2000s was dominated by skew morphism the
2010s have been dominated with the
launch of iOS 7 by flat design I think
we're going to move back into a world
with color texture dimensionality more
haptic feedback but I don't think it's
going to be schor fism where it pretends
to be like a wood drain to reference
like a dashboard or leather but I think
it's going to have a sense of Dimension
I think the reason why is we're spending
more and more time on screens and we
want the screens to replicate some of
what we see in the natural environment
light texture I think it's more
intuitive it's more playful I think AI
allows the development of more
sophisticated interfaces people in AI
are gravitating to image generating art
that has got more a dimension to it and
so I think that we've we've really
started to push this more
three-dimensional colorful aesthetic
that I think think I think it's going to
be where a lot of interface design is
going and we built this AI powered photo
tour where we created our own AI
computer visiting language that we
trained on a 100 million photos and it
can basically scan all your photos and
organize them by room so that's what we
did today maybe just to round it up what
I would say is that none of this would
have been possible in the old way of
working you know we could have
theoretically launch a lot of these
features but you know really getting
them to work together has been key and
guest favorites has required the guest
people you know you you have to work
with guests you have to work a host you
have to essentially you know you know
have you have to like figure out how to
communicate to the market so it's a much
more integrated approach the designs you
talked about they are incredibly cute
you tweeted a little video of a lot of
them like the couch with little textures
on it and uh uh it is really cool also
the listing tab I think people that
aren't hosts don't understand how
important the listing experience to a
host that's like I think how many host
are there 7 million something like
there's there's there's 7 million
listings yeah over 7 million listings
yeah and so that's like the home base
that's like the small business platform
for millions of people and so I I worked
on the host site so I have a special
place in my heart for host features and
I feel like Travelers don't really
appreciate the value of that part of the
product well yeah you you did some
amazing work there yeah I think that
like the big lesson Lenny the other
thing we learned is to create a great
guest experience you need
great host and to have great hosts they
need great tools and so if you want to
create a great experience for guests it
often starts with building great tools
for hosts to enable them to provy the
great experience for guests and so that
was one of the theories behind the
listing tab is we're going to build
great tools for hosts they're going to
love it and we also felt like if we put
te in the design of our app that hosts
are going to see that and that they're
going to actually but care into hosting
even more than they already do and they
they do put a lot of care in now
speaking of great products a defining
characteristic of briyan chesy in my
mind is how big you make people think
how you push people to think bigger
memories I have of you is in meetings we
present our goal and you're always
saying how do we tenx this what would it
take to 10x this idea and somehow we
often hit these crazy goals after you
10x them or sometimes just double them
what have you learned about just the
power of setting really ambitious goals
but also finding the balance with not
demoralizing people if they don't hit
these really ambitious goals as you know
there was a there was a saying inside of
Airbnb it was add a zero add a zero at
the end which is to make to imagine
something order man to bigger the
exercise isn't necessarily to say if
people say they want to hit a goal I say
okay I added to zero you have to hit
that goal it's more the exercise of what
would it take to be 10x bigger or do
something 10 times better
because what you find is when you push
people they will sometimes think about
the problem differently and one of the
best ways to get unstuck from a problem
is to imagine a 10x scale or 10x better
or 10x faster where you can't do the
current process to do it you have to
think differently about the problem and
to think differently about the problem
means you have to deeply understand the
problem and to deeply understand the
problem you have to break it into its
components and we might call this like
first principle thinking what are the
foundational elements
that comprise this problem and how can
you reconstruct them so the first thing
is I think by adding a zero at least
conceptually for teams to helps some
understand a problem the second is I
think one of the most important things
for a Founder leader to do is set the
pace to a team I think the pace of the
team is one of the most important things
you can do and that pace is sometimes
governed not by how hard people work but
how decisive they are if you want to
improve the speed of a company then make
faster decisions and that fast decisions
come from a bias of action if we're in a
meeting we don't just say like okay like
let's Circle back on this next week no
we'll have it done by next week let's
stay in this meeting till it's done what
are you doing have a bias for Action
who's responsible okay what are you
doing okay let's check in an hour I'll
call you in the morning okay how are we
do this and so you end up getting three
months of work done over that period of
time but the last thing I'll say about
adding a zero Lenny is I remember there
was a story about a great uh basketball
coach named John Wooden he was one of
the uh winningest basketball coaches I
think in college basketball history
perhaps the greatest and someone asked
him once I'm going to paraphrase what he
said like what is your secret to success
and he said that you know I just asked
my players to do their very best and I
remember thinking to myself that doesn't
sound like the secret to success asking
people to do their best but there was an
implicit thing that he didn't say which
is that he saw potential people that
they never saw on themselves and so the
role of a leader is to see potential in
people that they may not even see
themselves and when I tell somebody it's
not good enough either I'm saying you're
not good enough or I believe that you
have more potential than you're showing
me so in other words you can push a team
and they could feel demoralized because
they can feel like what they're doing is
not good enough if they have a fixed
mindset or you create a growth mindset
organization where the more I'm involved
the more I say you can do better it's
because the more I believe in you and I
know that you have more in you and the
way to know if a team could do better is
if they're life dependent I could they
do it and Indie Grove used to say that
there's competency and motivation and
motivation is if they're like not
literally dependent on it but like if it
was a crisis or if it was like a
defining moment in their lives I think
the job of a leader is not to make it
life and death that's too far but to be
able to motivate a team to see potential
in them that they don't see in
themselves and to really push them to
set a Tempo to break something down to
first principal thinking and if you do
that then I think that's going to be the
opposite of these slow movings kind of
soulc crushing
bureaucracies I've definitely been
through that where you set a crazy goal
and then we ended up hitting it and so
I've seen that
myself with some of the things you've
talked about of say do it now we're not
going to wait another week to Circle
back and the stuff you talked about of
taking on the CPO role not having a CPO
and also all these launchers it sounds
like a lot of work and aot of hours what
have you learned about avoiding burnout
and creating balance and also just
helping people on your team avoid
burnout and creating balance so first of
all um I want to give you a a a very
surprising learning I weirdly
now the more I get involved this is so
weird the more in the details I am the
more time I have in my hands that's a
paradox and I want to explain that
Paradox it doesn't make any sense but
when I explain this process to people
that I would be in the details we'd have
one- shared Consciousness I would review
everything we would do endless edits of
even the press release it would seem
like I would be working 800 hours a week
and that people would be disempowered
and that no one would want to do
anything and I got just the opposite
here's what I found if you decide to be
in the details and get very very
Hands-On like I did it might be a lot
more work for about one to two years and
so for one to two years it was way more
work than the old way but once we turned
the corner suddenly everyone started
rowing the same direction suddenly I
didn't have to be in meetings anymore
and people would do what I wanted to do
if I wasn't there and by the way that's
what the culture is they say the culture
is what happens when you're not in the
room and the brand is what people say
when you're not in the room and so that
became our culture that suddenly there
was fewer conflicts in the company there
was less turnover people were rowing in
the same direction that I wasn't
reacting before I would get 10 surprises
nine were bad now I get 10 surprises
nine are good and you don't really have
to do anything about good surprises only
bad surprises that I used to have to
intervene in projects I wasn't involved
in because they were going off into the
wrong direction and by the time I got
involved I was associated with
dysfunction but I only got involved
because it was dysfunctional it wasn't
actually going well and then it was
three times this work to fix something
because we weren't involved in the very
early eight stages so
I I was much more involved I had a lot
less time on my hands initially and now
I actually weirdly have a lot more time
on my hands but to answer question on
burnout I think is another very good
question I do not think I'm the poster
child at least historically of work life
balance I'm 42 years old I live with a
golden retriever I don't yet have a
family and if you asked me when I was in
college how I thought my life would be
right now I probably would have thought
the inverse that I have a family and I'd
one day run a company and I did things
in a slightly different order but one of
the things I've learned is that there's
this temptation to work more and more
and more hours and sometimes you need to
say an artist you have to step away from
the painting and you actually start
getting more derivatives slower and
slower and so I basically have tried to
break it a practice to step away from
the work and so here's some of things I
do every other weekend I like don't
really work at all and then you know
every other weekend
I work pretty intensely if I had a
family it would probably be more like a
day a day of the weekend I'd work more
intensely so you know I would you
wouldn't be a parent every the weekend
but I'm not so it's a little different I
usually make sure I exercise and I never
miss a workout so I usually like wake up
I'll do like 20 minutes of morning
cardio in a pelaton I'll go to the gym
three or four times a week and do
weights I I'll basically do cardio just
about every day I make sure that I eat
really healthy I have like a kind of
classic like bodybuilding diet of five
to six meals a day um so I think I try
to make sure I do that I try to make
sure I get a fairly good amount of sleep
and then I the other two things I try to
do is like have really healthy
relationships I think one of the most
important things that will govern like
how happy you're in your life is your
relationships I think the two govern I
think the three things your health your
relationships and your work those are
probably the three most important things
so as long as you're healthy and you
have meaningful work the last his
relationships and there was this Harvard
study it's the longest study on human
happiness I think it's 85 years old
and the question was what's the secret
of happiness and of course they weren't
expecting to have a single answer but
they got one and the answer was the
secret to happiness if there is one is
healthy relationships and I had found
Lenny that over the time of being an
entrepreneur I had gotten totally
isolated that it was almost as if I
didn't have friends I had friends but I
didn't keep in touch with them and every
time I reached out to a friend I had to
get them up to speed on my life and if
to get people up the speed you're not
really keeping as much in touch with
them and so I started making a practice
a couple years ago to make sure that I
have a group of friends that I'm
constant in touch with including old
friends so I have a group of high school
friends we have a group chat we take one
to two trips together Tri together year
I have a group of college friends we
have a group chat we take probably a
couple trips together a Year by the way
doing airbnbs are great we all get in a
house together and it's like you your
opportunity to have a shared experience
and if you don't travel your old friends
you have only old stories to talk about
and then you kind of say the same old
stories over and over so you want to be
able to have new shared experiences when
I stay here in New York City I'm in New
York right now that's why you don't see
my typical background I stay in my
sister's apartment so she's got a
two-bedroom and I stay in her house
because I like to see her and I just
make sure I spend a lot of time with
friends and of course we travel I mean
traveling is what I kind of do with a
lot of my friends and then I like to
draw and read so I try to make sure it's
Health work and relationships and I try
to make sure I Bal of each and you might
call family relationships you know I'm
just I'm single but you know that would
be another version of it I heard you say
along the same lines on a different
podcast about how when you were really
busy you didn't have time to reach out
to anyone and they never thought they
could reach out to you because they
thought you were so busy in the old
world I was reacting so everyone thought
I was busy so the people I really cared
about a lot of them said well he's busy
so he reach out to me when he's not busy
but here's a problem I was so busy that
all I was doing all day was responding
to people and so if people I cared about
didn't reach out to me I was just I was
dealing with incoming I could barely
deal the incoming now that was a mistake
but I was reacting and so by the way
here's another lesson for Founders a lot
of Founders spend their time based on
reacting so people will email them and
they'll wake up and they'll repond to
emails and suddenly their email sets the
agenda people ask for meetings and
suddenly the meetings they take are
based on the people who email them
versus like here's my strategy and then
over the next year what are the
relationships I need to have and the
meetings I need to take to be able to
execute this strategy if my life were to
end in a year or in 10 years or some
time Horizon that's shorter than I
expected who are the people I would have
wanted to make sure I spent time with
and if you imagine that your life is
finite because it is and you imagine
you're not going to be her as long as
you thought you would be because it's
possible it would completely change how
you prioritize your time and think
suddenly you would start to say no to
things and you'd say yes to other things
I now try to say no to what I call fake
work which is things that feel like work
but they don't actually move the ball
down the field and I really try to say
yes to work that's very meaningful and
people that are very meaningful to me so
yeah it's a really really good insight
and by the way that metaphor Lenny it's
true of companies too you can sometimes
be like you don't want to only spend
your time reacting or or spending your
time with the employees reaching out to
you I mean you do want to do some of it
but then you're rewarding you know only
one type of behavior and the introverts
or the people that aren't reaching out
to you aren't get to get any attention
just one more question and then I have a
quick fun question at the end I know you
have to run if I were to ask people who
are the most inspiring leaders in Tech
and in business in general I think you'd
be near the top of that list you've been
through a lot of ups and downs you've
learned a lot of lessons on the along
the way what have you found has been
most helpful to helping you continue to
grow and keep up with the business the
way the business is growing the scale
and just to take on this leadership role
is it like coaching is it reading is it
other mentors something along those
lines you asked really good questions
and by way thank you I um so I'll I'll
share a few thoughts I was I was with
Sam mman probably a few weeks ago at
dinner
and I told him I still feel like I have
a lot to prove I haven't made it yet and
he was like really surprised he's like
whatat are you talking
about and I didn't even realize that he
thought that was an absurd notion but I
said no I haven't made it yet it's not
to say I'm not grateful or I feel like I
need to get somewhere so that therefore
I'll feel like worthy but I have this
still this kind of beginner's
mindset that the bigger I get
the more a beginner I tend to feel it's
like a weird feeling I think like when
you when I first took off I think I
thought I like maybe like I knew
everything or I knew more than I
certainly did but then you get past some
Peak when you go into this prop where
you realize oh my God the moment you get
to some Frontier of knowledge you start
to become a beginner again and
everything is new and so I think the
first thing I try to do is to be a
beginner you know Pablo Picasso had a
was saying he said it took me four years
to learn to paint like Raphael but a
lifetime to learn to paint like a child
and so I've tried to always see the the
World Through The Eyes of a child and I
think one of the key characteristics of
a child is curiosity to see everything
with fresh eyes to not have too many
judgments like when I was trying to
figure out how to run a company I
studied the history of division
organizations and I studied Steve Jobs
but also studied like what Bill Gates
did and I studied like Alfred Sloan at
General ERS that mit's MIT Sloan is
named after and actually the founding of
divisional companies which I believe was
Dupont they were making powder for
Gunpowder the war ends what do we do
with powder turns out powder can be used
for paint but the way you sell gunpowder
and paint our different sales channels
so they created what we now know as the
divisional structure so I try to like
understand the sources of things I try
to learn I try to be Shameless about
reaching out to help I think that a lot
of people are afraid to reach out to
help because they think other people are
busy the biggest honor most people get
in their lives or one of the biggest
honor is when other people ask them for
help because we all just want to feel
useful so don't feel ashamed to reach
out to something for help it actually
like it gives a lot of them great honor
and I think you don't need to reach out
to people 10 years ahead of you they can
just be people a year ahead of you in
fact an entrepreneur getting started I
might be less youthful then than
somebody two years ahead of them that
knows like the latest distribution
channels that I like kind of have
forgotten so I think that that is the
key it's learning it's growing it's
curiosity it's constantly having that
hunger and that fire to always want to
be better to remember to feel like I
haven't made it yet because the reason I
say I haven't made it yet is because if
I've made it then I'm done and I want to
feel feel like an artist you know Bob
Dylan used to say an artist has to be in
a constant place of becoming and so long
as they don't become something then
they're going to be okay and so you you
have to always be evolving learning
growing and the canvas keeps getting
bigger the mountain toop keeps getting
higher and I feel like I'm just getting
started and I hope that you know I I
don't know how long you intend to do the
podcast but I intend to do this for a
long time and if you do or or whatever
we'll definitely want to have talks and
I hope years from now Lenny I hope 70%
of what I said I still believe but if
100% of what I say I still believe then
I probably haven't learned very much and
so if 90% I say I don't believe anymore
then I'm like you know kind of
delusional and wrong but if but but I
sincerely hope that I retract or change
or modify a few things I said today in a
few years because that will mean that
I've gained more wisdom and so how do I
do that by being curious that is
beautiful it reminds me you mentioned
Sam Alman I'm there's a tweet that he
put out a couple weeks ago that I'll
read real quick many people have reached
out to offer help and advice over the
past year no one has gotten close to
Brian chesky in terms of delivering he
will take a midnight call at any time
put in hours of work on any topic answer
difficult questions correctly with
Clarity make any intro
Etc how's that feel to have seen that it
was I I had no who was going to do that
and I just want to say like I think Sam
is obviously like a once in a generation
founder I think what he's done with open
ey is extraordinary and when he launched
chat gbt I had known him for a really
long period of time and I kind of knew a
sense of the journey he was about to go
on and I think that he was very deep
into the technical part and then
research Orient part of open AI but it
turned out there was a product a design
a marketing a leadership a sales there
were all these other functional
responsibilities and so being able to
just play a small part in you know
giving some advice when necessary and he
would take what he wanted to disc
discard others but I think Lenny maybe
this goes to another thing which is all
I tried to do with Sam is what other
people did for me when I started before
y commentator there's a person named
Michael cyel he's in y commentator and
he used to meet with me and give me
advice and he wasn't an official adviser
he wasn't an investor I didn't hire him
or anything like that he wasn't board
and I asked him I said how do I repay
you and he said well I want you to pass
this on to other Founders and I would
meet with a lot of people in the valley
and there was just this like incredible
culture of
generosity that that we all were going
to win you know if the ecosystem was
healthy and the ecos would be healthy if
we all helped one another and you kind
of pay it forward and so you know I um
you know I think that it's just one
continuation of the valley of people
helping one another learning from one
another and I also feel like I learn by
teaching as
well final question when someone joins
Airbnb there is a very long-standing
tradition of sharing a fun fact about
yourself who might be the longest
standing tradition uh it's always tough
on the spot but I'm curious Brian if
there's a fun fact that you want to
share about yourself that maybe people
don't already know yeah so a fun fact
about me is that I actually spent most
of my life as an artist
you know when I was 5 years old I
remember my parents like take me to the
Norman Rock Museum and I would sit in
front of you know his beautiful
illustrations they're really paintings I
should say I shouldn't even call them
illustrations and I would try to
reproduce them and I got obsessive with
art I remember when I was maybe in
elementary school I asked Santa for
poorly designed Christmas toys so I
could redesign them when I got soly
older one of my friends I went to his
house I'm gonna say I was like eight or
nine years old and his dad was basically
like redoing his deck but his dad
decided to design it himself I think
maybe's an architect so he had this
giant dining room table and he had like
this velum paper and he had a t-square
and a drawing triangle and a protractor
and I just the cool they were really
cool looking tools and they were
basically floor plans and Architectural
drawings so I got into architectural and
landscape design when was like eight or
nine and that led to my interest in
architecture I went to RPI was a
freshman of co uh of high school to do
like a pre-ol program then I got into
like more and more drawing and figure
drawing then I got to film and animation
then I got involved in in environmental
design I realized that if you buy stock
in a company you could get these cool
glossy annual reports this is kind of
when the internet was kind of like Nason
and people still mailed annual reports
and so I got my dad to buy a few shares
at some Disney stock and I got these
renderings and the had report of theme
parks and I started like drawing like
and designing like theme parks in
communities
and I was at this private school for
actually for hockey because I had it
parallel life where I was playing ice
hockey and I I thought I was going to
play college hockey my dad was really
into it I was really into it and I had
an art teacher in high school at this
military school that's another fun fact
I basically went to a military High
School wow did not know that and at this
military Sports Academy kind of oriented
high school I had the same art teacher
from 8th grade to 11th grade and that's
not a good thing by the way I saying
this a good thing because I I was not
diversifying my skills and so I leave
this high school because I wanted to
pursue different interests than hockey
and I transferred to my public high
school late my junior year and imagine
like transferring to a new public high
school late junior year and I meet my
art teacher who changes my life her name
is Miss
Williams and she sees my artwork and by
the way my mom was
nervous about me becoming an artist she
used to sell me I chose a job for the
love and I paid no I got paid no money
she used to choose a job that pays you a
lot of money and I said to my mom one
day I'm going to be an artist she said
oh my God you chose the only job where
you're going to pay less than a social
worker so I think my parents you know
they were support of me going to Art but
they were very nervous and then Miss
Williams told my mom she said don't
worry he's going to be a famous artist
one day I wasn't to become a famous
artist but what that did is I think it
gave everyone the confidence for me to
pursue art I ended up being one of the a
winner there were multiple winners of a
national art competition and I had my
artwork displayed in the retunda gallery
that then led to me getting a
scholarship at the r School design where
I end up going to Ry it's like you know
it's kind of like it's kind of like MIT
for design or whatever it's like a it's
a it's prestigious Art and Design School
but I got to risti and I realized I was
born a 100 years too late for what I
wanted to do which is you know draw and
paint and I felt like at that point
photography and now ai generated art but
certainly even back then photography was
replacing a lot of the skills that like
that I need that that I had and that's
when I was in my fresh beer of college
and I learned about a funk field called
industrial design they IND they said
industrial design is the design of
everything from a toothbrush to a space
ship and everything in between and
really Lenny maybe just to rande the
story because I know was a fun fact but
I'm kind of just this is the pre
founding story that I never tell I don't
think I could have ever done what I did
if I wasn't an industrial designer I
think industrial designer is different
than a graphic designer because an
industrial designer you have to actually
you know you have to work with
Engineering in your in your training you
have to like I worked with mechanical
engineers electric Engineers you have to
understand manufacturing industrial
design very accountable to sales if you
design a building an architect and you
design office building office building
doesn't get leased the architect is
usually not on the hook for it but if
you're industrial designer you design a
product doesn't sell you're like kind of
on the hook for it at least people
assume you didn't design a good product
so you to understand marketing and
strategy and so that became this Gateway
but I didn't really want to make items
and objects my whole life but at Ry the
biggest value I got in addition to
learning industrial design was I met my
co-founder Joe gbia and the day of
graduation Joe looks to me he says Brian
I think we're going to start a company
together one day and I had no idea what
he was referring to so I moved to Los
Angeles where I work as an industrial
deser for two years when one day I got a
package in the mail that changed my life
I opened this package and it's a SE
cushion with a handle on it and it's a
letter from Joe my my friend from Ry he
said I started a
company in everyone in San Francisco I
live in San Francisco and all these
people are starting cupies you should
come here and this is in 2007 YouTube
had just come out I had like seen all
these Steve Jobs Keynotes finally on
YouTube I didn't know who he was I never
heard his voice before before YouTube
and apple had this Renaissance and
Google was on fire and Facebook was
taking off and it felt like the gears of
the world that were turning were in San
Francisco and so one day I go into to
work and I quit my job my boss is
dumbfounded and I pack everything the
old uh old uh backseat of old Honda
Civic I get to San Francisco and Joe
tells me the rent is
$1,150 I don't have enough money to pay
our rent this design conference come to
San Francisco all the hotels are sold
out we said what if we turned our house
into a bed and breakfast for design
conference I didn't have any beds but Jo
had through our beds we called the airb
and breakfast so my fun fact was I was
an artist and designer before Airbnb
really an artist at least how I thought
about it and I think that's maybe one of
the things that makes irban be different
because there's not a lot of designers
or artists running Fortune 500 or SCP
500 companies and I think that intuition
imagination design curiosity I think we
need more of that by the way I think the
people listening I think everyone on
this what listen you has these qualities
but I think that a lot of companies it's
like we're a body and the companies are
cut off at the head they're disembodied
from their heart and they're often
really biased towards one side of their
head and I think some of the greatest
scientists played musical instruments
like Einstein I mean I think that like
being a whole well-rounded way of
thinking about the world is good so
anyways that's my final thought I love
that fun fact because it almost explains
everything you've been talking about
which is rethinking the way companies
can run doing things super differently
so I really appreciate you sharing that
I also love that it transitioned into
the creation Story of airb B which
happens a lot at airb B people hear that
story over and over because it's h so
interesting and so important Brian I
know you have to run thank you so much
for being here and being generous with
your time thank you Lenny and
congratulations everything you're doing
thanks Brian bye
everyone thank you so much for listening
if you found this valuable you can
subscribe to the show on Apple podcast
Spotify or your favorite podcast app
also please consider giving us a rating
or leaving a review as that really helps
other listeners find the podcast you can
find all past episodes or learn more
about the show at Lenny podcast.com
see you in the next
episode
Loading video analysis...