Video summary
Andrew Wilkinson, a successful entrepreneur and author of *Never Enough*, argues that many highly productive individuals are essentially walking anxiety disorders harnessed for productivity. He attributes his own hyper-vigilance to childhood trauma regarding money and family dynamics, which drove him to solve problems obsessively rather than simply enjoying life. While he initially relied on lifestyle changes like strict diets, exercise, and meditation to manage this internal chaos, Wilkinson discovered that these measures were insufficient because the root cause was chemical. After researching genetic polymorphisms using 23andMe data, he identified himself as a hyper-metabolizer who required specific pharmaceutical intervention. He eventually found relief with newer medications like Viatris (Trelstar), Brintellix, and Voxine, noting that while there is significant stigma around taking daily medication for mental health—unlike allergy pills—he believes admitting to anxiety and seeking chemical help is a functional necessity rather than a failure of character. The podcast explores the dichotomy between extreme success and personal fulfillment, highlighting how wealth often exacerbates existing psychological issues rather than curing them. Wilkinson observes that successful people tend toward two extremes: grandiosity or "grandio humility," where they perform acts of modesty to signal their virtue while maintaining immense power. He contrasts his own struggle with figures like Warren Buffett and Charlie Munger, who possess singular obsessions—Buffett in reading annual reports and Munger in building machines—that allow them to thrive but are not replicable blueprints for everyone else. A central theme is the danger of copying others' strategies; Wilkinson emphasizes that one cannot use someone else's knowledge or "cheat codes" to achieve their own goals, as life paths must be custom-fit based on individual idiosyncrasies and what makes a person miserable rather than just happy. As fame grew from obscurity to niche influence, Wilkinson experienced the reality distortion field where external validation clashes with internal identity. He describes the unsettling shift in how people treat him, noting that while he receives kindness, it also brings unwanted attention and fear of being treated differently or stalked by fans seeking business advice. This dynamic creates a "treadmill" effect where success does not lead to satisfaction but rather shifts anxiety from financial security to health obsessions, politics, or other global problems amplified by the internet. To combat this, he advocates for strict boundaries on information intake, treating his exposure to news and social media like an addiction recovery program by locking down devices and limiting screen time. He argues that humans are better at predicting what makes them sad than happy, so avoiding misery is a more effective strategy for designing a fulfilling life than chasing abstract happiness. Finally, the discussion turns to managing wealth, hiring, and philanthropy in light of Wilkinson's own journey toward giving away his fortune through initiatives like The Giving Pledge. He stresses the importance of alignment in business relationships, ensuring team members have "skin in the game" so they share in both risks and rewards rather than working for a flat salary without emotional investment. Regarding effective altruism (EA), he acknowledges its potential but notes how it has been damaged by high-profile scandals like the FTX collapse involving Sam Bankman-Fried, which tainted the movement's reputation despite many practitioners doing genuine good work. Wilkinson concludes that while failure is culturally accepted in entrepreneurship and innovation, philanthropy often faces a harsher standard where one bad actor can ruin an entire field of charitable giving. His ultimate goal for the future involves deprogramming his own anxiety-driven voice to stop asking "what's next" and instead focusing on how to effectively deploy vast resources to maximize good without being consumed by the endless pursuit of more success.
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I'm indoors and some people may be
noticing that I'm wearing sunglasses
look at this uh this is not a ad for
rayb Ban's metag glasses but my friend
bought me these the other day and I can
record you front on so no one will ever
usually get to see what this looks like
from the other side but this is my view
this is what it's like this is what it's
like to be
me anyway you've got a quote that says
most successful people are just a
walking anxxiety disorder harnessed for
productivity why do you say that so um
all my life I've had this feeling that
when I wake up I need to do something um
I'm just constantly whipping myself I
basically feel like if I don't achieve
I'm a piece of [ __ ] I don't know where
it comes from um but I am just obsessed
with solving problems and I'm hyper
aware of problems like at any given time
my brain is five steps ahead of all the
things that could go wrong and my my
game if you will is to try and prevent
all the terrible things from happening
and I think that makes me a good
entrepreneur but it makes me kind of a
miserable
person how have you learned to balance
those two given that you want to
maximize your Effectiveness
entrepreneurially but presumably not do
it at the price of your sanity well I
think um you know understanding when
you're in a Sprint and when to use that
I think you know an elite athlete would
understand that if they run it a full
Sprint constantly they're going to get
injured and I think in my 20s you know
when it really mattered I embraced it
and in my 30s I started realizing that
I've achieved the goal I want I've made
enough money that I'm happy and it's not
that I want to Coast but I just want to
turn the volume down on that stress a
little bit because I've learned how to
achieve leverage using delegation and
other people and buying businesses and
all those other things and so um I think
one of the problems with the way people
think is that they imagine that when a
then I'll feel good right so you often
hear people say you know I just want to
leave it all behind and move to Bali
forget it all the problem with moving to
Bali is that your brain comes with you
and your brain is anxious if you're
programmed in the way that I am doesn't
matter where in the world I am I'm just
thinking about problems and so for me
actually it's been chemical I started
taking a SSRI about three years ago and
I remember about a week after I started
to take it I would hear the anxious
voice and all the concerns to creep in
and it was just a little bit quieter a
little bit more distant so for me you
know meditation exercise being in a
healthy relationship all those those you
know form the groundwork but actually it
was a chemical problem to some degree
what have been the positives and
negatives of the ssris you often hear
many nightmare stories and also success
stories what's the The Real World review
so I was terrified um first of all I
never thought of myself as an anxious
person um must be a difficult admission
to make yeah I mean to realize that you
are acting irrational you know you are
obsessing over silly things so in my
business life very functional in my
personal life um I would become obsessed
over okay I'm taking this vitamin what
could this vitamin uh have a negative
consequence oh my God is my tap water
filled with PF do I need a new type of
filter uh am I unintentionally exposing
my kids to you know raid on gas in the
basement whatever obsessive thoughts
like that like OCD kind of stuff and um
so I started realizing at a certain
point that while I had everything I was
miserable inside I was a dust bow farmer
inside of my head and so I recognized
that and I went to my doctor and I said
hey what can I do about this and he
prescribed me an SSRI and then I went on
Reddit and on Reddit you only get the
extremes you get the people who say this
is amazing and then you get even more
people that say this ruined my life five
star reviews and one star reviews only
exactly and so I was really scared to
take it and it sat on my um sat on my
you know nightstand for a year and
finally I started digging into it more
and I said okay how do I ensure that I
don't have issues with this and I
realized that a lot of people who take
ssris have uh a meta they have a they
basically metabolize drugs differently
so if you look at your 23 and me data
you can actually see if you are hyper
metabolizer or not and I realized I was
a hyper metabolizer and so if you think
about it it's kind of like um you know
you do a drug let's say you do a massive
amount of psychedelics or something like
that there's always that moment where it
hits you and it's like oh my God this is
I need to go to the ER this is crazy and
then it kind of Mellows out and I think
that same thing happens to a lot of
people with ssris and so I found that I
had that genetic polymorphism and I
actually found a drug that was a newer
class a different class that I could
metabolize
called viotin which not that many people
know about I mean it's called trellex
brintell and V oxine depends on where
you are in the world um and it's been
incredible for me the only downside that
I've had is that my stomach sometimes
gets a little nauseous Health gets
impacted a little bit a little bit but
honestly I mean it's there's such a
stigma around I think admitting you have
anxiety less and less over time um and
then taking a drug not that many people
come out and say hey I take a drug every
day I take a pill and helps function and
uh you know what's funny is they'll also
take an allergy pill and not think twice
and that's changing systems in your body
and reducing histamine and histamine is
in your brain I mean the Lord knows what
it's doing but uh for some reason when
it's serotonin and dopamine people panic
I think there is a and rightly so a
concern about overprescription around
genz relying on these drugs to buttress
their mental health when they're not
eating well they're not getting eight
outs of sleep at night they don't have a
good social Circle they're not
exercising they're not all of those
things um but that that is very
interesting to consider okay I've gone
through these steps and this is
something which genuinely had a net
positive impact I was aware of what the
potential externalities were and I just
decided to go through it I um I done it
all so I built a rigorous exercise
regimen I had a 45 minute meditation
every day I had you know I was eating a
very strict diet and it was one of those
things where if I did everything
perfectly I'd feel fine but as soon as
one thing broke down I would I would
break down myself and so I realized you
know that's not functional that's not
how much of that do you think was the
impact of the things that you were doing
and how much of that do you think was
the story that you told yourself about
being the sort of person that did all of
those things a lot of it was the story
you know I think if somebody tells you
um you know if if if somebody told you
look every time you fly in a plane you
increase your risk of getting brain
cancer by x amount you're going to
obsess over it and think about at least
certain people that are tuned in an
anxious way will and what's fascinating
is now I will listen to the same podcast
I was listening to before I'll listen to
Ronda Patrick or Peter AA and they'll
talk about some problem or you know
medical issue or whatever and now my
brain goes oh that's interesting okay
maybe to I might have that I've probably
got that exactly wow so going back to
the uh successful people are walking
anxiety disorders harness for
productivity you have been around an
awful lot of hyper successful people is
this part of the course in your
experience the upper echelons of the
richest most successful people on the
planet are they also on average driven
by that same sort of compulsion well I
think um this is a really annoying word
right now but trauma right you know a
parent who um mistreated you a teacher
who told you couldn't do it everybody
has a chip on their shoulder and the
investor Josh Wolf has a great saying he
says chips on shoulders put chips in
Pockets right so often people who have a
chip on their shoulder go to achieve
great things because they're trying to
prove something to the world and I think
that some people have uppercase tea
trauma and some people have lowercase
tea trauma for me I have lowercase tea
trauma you know my dad didn't make
enough money growing up my parents
fought about money my solution to that
was make money and everything will be
good well it it didn't work out that way
but um I think that you know you have
someone like Elon Musk who he's on the
Spectrum and his dad you know was
physically and emotionally abusive to
him he's just way more successful than I
am and so I think what I've found is
that most people are a result of
something complex inside of them and uh
you know who who else but a complex
person spends their entire life trying
to launch rockets into space or you know
Bezos trying to deliver a package
slightly faster than every you
yeah what did I what did I expect like
what what would you expect of this but
would you expect them to just be a
simple happy go-lucky human they don't
ever notice any
concerns how many people have you found
that have managed to achieve some degree
of worldly success in the well balanced
I'm driven by a desire to do well but
not a sense of insufficiency there's no
hypervigilance there's no underlying
anxiety disorder how rare has it been to
find people like that I think they exist
but I think if you ask their kids they
would tell you that they're crazy in
some way I think a lot of people are
very good at appearing that way and I
think that one of the fascinating things
about rich people is you see grandiosity
and then you see grandio humility so
what I mean by that is people who are
grandiose they have the $500 million
yacht the this you know 10 houses go to
the Oscar parties whatever and then you
see people who wear the Casio watch and
they're humble and they you know live in
house in Omaha or whatever it is and I
think there are two different forms of
uh you know they go e one way or the
other right and I think even the people
who go um you know grandiose humility
they still make a point of everybody
seeing look I'm wearing the Casio watch
aren't I so humble right not to
criticize I think it's you really only
have two options you can either be
extreme or you can be signal or counter
signal exactly choose your direction
Western man yeah what did you learn
you've spent some time with Charlie
Munga Warren Buffett uh what have you
learned from being around guys that are
so uh Lindy in the way that they've
existed well I think that they have a
singular Obsession you know Warren
Buffett um his wife T you know talks
about how he really had no nothing in
his life outside of reading annual
reports and running his business he's so
incredibly obsessed with being the
world's best businessman and investor um
and I think that's great for him you
know but I think that when I read about
Warren Buffett I decided that I wanted
to be like him um I I was running all
these companies and I was super stressed
out and miserable and dealing with
people problems constantly and when I
read about Buffett I was like oh my God
this guy he's abstracted business away
all he does is read all day and relax
and then he buys a couple companies
every year and I tried to do the same
thing I got an office and I was away
from everybody and I had CEOs running
all my
well I couldn't read an annual report
for more than 30 minutes without losing
my mind and wanting to go send a bunch
of emails and talk to people and do
stuff so I think that you want to make
sure you're playing a game where you
would naturally play it either way and
in that instance you know that wasn't
for me I have a different version of
investing that I enjoy and it's much
more people Centric and what about
Charlie Charlie um he is truly somebody
who did whatever he said said whatever
he wanted he did whatever he wanted and
he also just lived incredibly humbly
like I remember going to his house um
you know in La you know I've gone I've
gone to lots of people's fancy houses in
LA and usually somebody with his netw
worth I think it was like six billion or
something at the time they've got like
helicopter pads and creepy statues and $
million pieces of art everywhere or
whatever Munger lived like a wealthy
dentist you know he lived in a normal
neighborhood in a house that he designed
in the
1950s and really I think what he loved
was building machines that worked and
figuring out uh what didn't work and
avoiding it and he's just a learning
machine I mean back to the point of
building a life that you want all he did
was read that's all he did every time
I'd go to his house he's just sitting
there with a stack of books uh and he's
just devouring you know four or five
hours a day of reading and not that many
people can do that there's a reason why
they're so wise and so successful
for you must have seen that clip that
got circulated about a month ago where
Warren was doing part of the report and
then turns to his left and says Charlie
you see this so sad man that was sad I
think it's uh I think it's really hard
they had such a great Rapport those
two you tweeted something out that I
think is actually analogous to what
we're talking about here uh quote here's
the number I used to win the lottery
sent by entrepreneurs giving advice
what's that mean so I think that
um you can't use somebody else's
knowledge to achieve your own goals and
I've i' I'd say that most of the bad
choices I've made in life has have
actually been a result of taking advice
from other people because defin
definitionally let's say you talk to
let's say you talk to a podcaster who
started in the era of This American Life
they're going to say oh you need to be
on PRI and you need to do this and that
and the other you're in a different
world different competitive landscape
and so I think that people will over
index on what other people did and say
if I just copy their cheat codes it'll
work but as we all know if you were to
play the lottery with the same numbers
someone else used it's not going to work
right and so I think that people um
people need to ultimately make their own
decisions they need to make their own
mistakes and their life should be
focused on making as many small errors
as possible and then learning over time
I have never
been able to tell somebody that
something isn't going to work out for
them right people don't change they need
to hit rock bottom first and only once
they hit rock bottom do they change um
one example you know I was an incredibly
trusting person to the point where I
would watch I thought I thought everyone
was good so I remember watching um you
know like Harry Potter movies and you
see like Voldemort or die hard and
there's the bad guy I would just think
there's no such thing as bad people
right there's misunderstood people
there's complicated people but there's
no such thing as like true bad guys and
then I had a few business experiences
where I got defrauded or worked with
someone who had lied to me and was truly
a bad actor and from that point on I was
forever changed from that point on it
was trust but verify I had been told
over and over and over again you can't
do a good deal with a bad person or
don't work with someone with the
following qualities but I really had to
experience it in my body and I think
it's a little bit like with kids you
know when you have kids they're running
around and they're you know my sons are
running and fighting on the dock and I
know one of them is going to get a
splinter and I know one of them's going
to fall in the water and cry and I've
got to let them have that little flesh
wound so they don't have a mortal wound
in the
future how much truth do you think there
is in that equivalent uh don't try to
use the strategy somebody else did
because it's very particular to their
time to their industry etc etc uh when
it comes to LIF style designs so what
you were talking about there
um Charlie Monga Warren Buffett all that
they want to do is be the best business
person in the world or just spend five
or six hours a day reading not everybody
can do that therefore not only is that
not necessarily a successful strategy
that's going to lead to them profiting
over time but it's also not even
necessarily going to be a happy life
like it's a life that is designed for
those guys with their particular
idiosyncrasies for what fulfills them
and makes them feel like they're
flourishing uh I think a lot of the time
both in personal and professional life
people are trying to okay what give me
the blueprint of what I need to do in
order to be able to be wealthy and be
happy and both of those things are by
design custom fit totally I mean look at
lawyers right how many people do you
know from school who said I want to be a
lawyer because my parents taught me that
it's a good job and I can make a lot of
money and I watch Law and Order and I
thought it was cool well if you actually
sat you know think about what most
lawyers do they're reviewing documents
and it's doents for like a real estate
transaction or like someone buying a
company they're looking through little
Clauses and then going to a legal
reference that is not necessarily the
job that most of these people set out to
do and I think that ultimately people go
for jobs that have external validation
and they like the idea of but they don't
actually like the reality of it I think
that people when they're choosing jobs
or directions for themselves instead of
trying to imagine what's going to make
them happy should instead have anti-g
goals they should be thinking about what
do I hate when am I maximum miserable
right so I'm maximum miserable when I'm
having to read all the time or I don't
like doing paperwork or I really don't
like having a lot of meetings I like a
lot of time where I'm just quietly
thinking and instead use those criteria
to choose the life they want because I
don't think humans are very good at
predicting what makes them happy but
they definitely know what makes them sad
so you're saying that it is more
important to stop doing what you hate
than to focus on doing what you love
100% dig into that for me tell me a
little bit more so um there was a time
maybe five or six years ago where me and
my business partner Chris were really
unhappy at work uh we found that we were
traveling constantly we're away from our
kids our calendars looked like a game of
Tetris um we were just not we we kind of
had this moment of like do we really
want to keep doing this we're just
miserable and Charlie talks a lot about
the idea of inversion he says invert
always invert always try and twist
something around instead of saying how
could I help the homeless much or how
how could I help the homeless the most
you say what harms the homeless the most
and then you design something
accordingly and so we started writing
out this list of all the things that
make us miserable okay so we don't like
being scheduled well we started saying
you know we're not allowed to be booked
on Tuesdays and Thursdays and on those
days we have lunch uh we always want to
sleep well
okay well we're never agreeing to a
morning meeting we don't like owing
people things okay well when we raise
money for these companies we're going to
do it in a very specific way so that we
don't have to answer to people um and we
really just started designing our lives
around that and we found pretty quickly
we were much happier just focusing on
those things whereas what we've been
doing before was going well when we're
rich then we'll be happy right when we
have all these successful businesses or
when we're more like Warren Buffett
that'll be when we arrive and that has
never um um frankly never delivered
happiness for us we'll get back to
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checkout I think it's true to say that
when you ask someone what makes a person
happy they will have maybe a vague idea
about what's going on but if you were to
say how would you make a happy person
miserable that's pretty reliable that's
very very easy one of my favorite
questions that I ask on the show is what
do most people get wrong about x what
most most people get wrong about
entrepreneurship what do most people get
wrong when starting a company what do
most people get wrong when designing a
hypertrophy routine for the gym because
that question is I think much higher Roi
look here are all of the places that you
can fall into a huge hole don't do those
and you will expedite success way more
quickly than actually trying to expedite
success the same thing goes for
happiness the same thing goes for
business
totally I wonder about
the I wonder about how to make avoiding
doing things that you hate more sexy you
know because there's this degree of
Puritan work ethic I know that I
certainly have it a lot of the people
that listen to this show have it as well
you like a classic sort of workingclass
mentality I grip my teeth and get
through I've heard that hard work and
discipline and resilience are traits
that I should try and push for I value
them in myself I think that if I work
hard maybe I can cultivate them so I'll
do that but it it's kind of like anti-
lever in a way it blinds you to how
could I make this more fun how could I
make this more effective how could I
magnify the outcomes that I'm getting
from this particular thing I came up
with this idea that I wrote about this
week called the productivity rain dance
so at the start of this year I asked
myself a question what do I do that I
think is productive but isn't and what
are the things that I do that I don't
think are productive but are and what I
realized was i' basically made this
weird sort of sacred ritual where I'd
kind of like wave the sage around and do
but it was sitting at my desk when I'm
not working keeping slack notifications
down to zero trying to sitting on email
clearing off stuff that really doesn't
matter uh being on calls where there's
no actual objective on the other side of
it they all felt like work but the
actual outcome that you got on the other
side was nothing the reverse what are
some things that are productive but I
don't realize are was uh always saying
yes to a coffee if somebody's coming
through town for a brief period of time
organizing dinners with groups of
multiple friends from different uh
friend groups reading going for a walk
without uh anything in my ears uh and
long drives those things were super
productive when I actually looked at how
it made me feel and even if you forget
about productive like what makes you
feel good and what makes you feel
terrible and those were two buckets of
things that managed to do both both be
productive and make me uh happier or be
unproductive and make me feel miserable
and yeah it was so uh very enlightening
to see that and it's taken me six months
to basically realize that I'd created
this
odd Detachment from inputs and outcomes
and I'd Focus so much on inputs just I'm
doing the I'm doing the meditation I'm
doing the breath work I'm doing the
whatever so yeah but what's the what are
you trying to achieve here and is it
actually achieving anything at all or
are you just going through this sort of
odd dance in the hopes that on the other
side at some point in future good things
will
come what's that Buddhist thing of like
all suffering comes from attachment and
if you attach yourself to the idea that
you have to have slack at zero you've
definitionally definitionally ruined
your life because it'll constant
um one thing I think people miss about
entrepreneurship in my opinion
entrepreneurship is about laziness the
initial laziness is about fixing a
problem um I was just talking to
somebody who's a mom and we were
brainstorming a business idea and she
was saying you know I hate packing my
kids lunches in the morning it's so
stressful and we were like oh it would
be cool if there was a service that did
that laziness right out of laziness out
of seeing this problem where is
someone's pain a business right so it's
embracing laziness there and saying
let's make this thing easier everything
that a great entrepreneur does from that
point on is about building a machine
it's not about whipping themselves and
pushing a boulder up a hill it's
actually about getting the right people
on the bus and building a machine that
involves people and systems and process
and you actually want to get to a point
where you don't do anything your job is
to fire yourself as an entrepreneur
right Steve ell's from Chipotle is not
on the line making B
right he built a machine and then he
scaled the machine um and I think that
uh embracing that laziness is something
that a lot of people really struggle
with a lot of people think that they
need to whip themselves and work harder
and I know that was certainly true of me
in the early days I used to think I'm
not a good manager of people you know I
always found that once I was managing
about 15 people I hated it I hated
giving speeches and writing big communic
emails and building system and doing HR
I just never like that stuff and I would
just book I would read book after book
after book trying to become a great
manager of people and eventually I just
realized oh my God there's people who
love managing people I'll hire an HR
person eventually I'll hire a CEO and I
think that you ultimately if you want to
be a great entrepreneur you want to be
Teflon for tasks you want to let
everything that you don't enjoy go away
and when you do enjoy something and
you're doing it you have to say am I the
best person to do this and ultimately
what you want to do is build a machine
and then pour your buy whatever your
contribution is you want to pour it into
the machine and then have money come out
the other side and then hopefully you
want to take that money and you want to
put it into another machine and so on
and so forth that to me is what
entrepreneurship is and if you think
about what Warren Buffett
does let's say that um let's say you
wanted to sale from Seattle to Hawaii
most people go down to the beach with
their buddies they find a bunch of logs
they tie them all together they build a
little sale and they basically have a
little raft and they hope that they
drift to Hawaii well that doesn't work
right starting a company usually fails
it's really hard you don't know what
you're doing in the beginning Warren
Buffett gets on a cruise ship he finds a
great cruise ship cruise ship with a
great Captain he buys a ticket a stock
certificate he boards and he just lies
in the sun reading the entire time and
when I saw that I was like oh my God
this is the laziest most successful
person in the world who has abstracted
business away to the most incredible
degree and that to me is the ultimate
entrepreneurship right I think people
think of Warren Buffett as an investor
and it's like no no no he's an
entrepreneur he's just delegated
absolutely everything to the point where
he has 500,000 employees and hundreds of
companies we were talking before we got
started about something I think a lot of
people feel the pain of which is this
transition from operator to executive
and you know you may even be able to say
it's when you get around about eight
people in the team or whatever it might
be um but you know I I ran businesses
for my entire life 18 years old I sat
next to my then would be business
partner for the next decade and a half
in my first ever seminar at University
and if you have grown up maybe not
without money uh or in an environment
that Praises hard work and a sort of
Puritan workout e uh or if there's an
expectation that you kind of need to
Signal being busy which is also um kind
of like a a proof of work that you put
in front of both the subordinates to say
I'm here with you I remember I ran
nightclubs and um one of the things that
we used to have to do which was kind of
hilarious was if it was the middle of
November in the northeast of the UK
freezing cold you know it's wet it's
it's awful uh but the venue manager of
the nightclub that you were running your
event at they'd expect you to be stood
there on on the front door with them
because they are they're freezing their
tits off on a quiet wedding day in
November in Newcastle upone stand next
to me prove that you're invested in this
thing uh and that um mentality that my
suffering is somehow in accordance with
how hard I've worked which is and how
hard I work is going to Bear fruits
eventually you can quite quickly
actually buy bypass the how hard I work
thing and just do Straight suffering
equals outcome on the other side so what
is there to say for someone who feels
like okay the uh thing that I am doing
or even the situation I'm hoping to get
myself into at some point in the not too
distant future I can start to see the
murmurings of feeling overworked feeling
a little bit burned out calendar being
too busy I feel like I'm doing task that
I shouldn't be doing I need to maybe
upgrade from operator ground floor to
Executive how do people psychologically
structurally professionally how do they
go through that so um
I started a web design agency about 20
years ago and originally it was me and
my underwear in my apartment and then I
had a client asked me for um a CO to do
some coding that I didn't know how to do
and so I went oh my God I panicked and
ran around like a chicken with my head
cut off and tried to learn it and it was
too confusing and I finally realized
that my girlfriend's uh best friend's
boyfriend n how a code and so I went to
him and I said hey how much would you
charge to do this and he said 500 bucks
and so I went to the client and I said a
th000 bucks cuz I wasn't sure if I was
going to get negotiated down and they
just said yes and in that magic moment I
was like oh my god I've just made money
and I didn't do the work myself right so
that's the most basic form of Delegation
and then you get into the next phase
which I call Higher One to higher 10 so
you could go and say I want to build a
marketing department I'm going to go
hire an affiliate marketer a PPC
marketer an email marketer blah blah
blah blah or you can hire one person a
VP of marketing and that vp's job is to
go and build the org and hire them and
manage them and that's the next level of
Delegation where you now have this
leverage where you hired this one person
and they own an entire part of your
business and um and then you know the
Final Phase is really firing yourself
fully to say to dare to say um I think
someone else can do my job better as CEO
and that for me was one of the hard
things to let go because you know my ego
was tied up in it and IID always you
know my identity was that I was an
entrepreneur and like you I had this
kind of work ethic of I'm being lazy and
I shouldn't do this but it was one of
the best things I've ever done because
it allowed me to achieve crazy amounts
of Leverage by 40 different companies
and you know do all the stuff that I've
done since then um but it's a really
hard sad thing and I don't know that
it's necessarily something I recommend
for everybody I think that some people
should be in their underwear in their
apartment freelancing I think that's
great I think if you can make good money
and you're happy and you like being an
individual contributor that's awesome
other people want a company with three
people other people have grand Ambitions
and they want a single track and just
Dominate and do an amazing job in one
industry and one company and then
there's other people like me who are an
inch deep and a mile wide and they want
to be all over the map and I I think
like if you look at your personal life
if you're somebody who buys way too many
books you know more books than you can
ever read in a lifetime you have a
overwhelmed Netflix CU your letter box
is you know crazy um you probably want
to consider having a life where you have
a lot of variety and you're doing a lot
of different things and you have to
embrace that and say you know what I'm
doing a focused job being a CEO of one
company and yet I'm a distractable
person who likes a lot of uh Variety in
their life and so I think embracing that
when logical and other people not I I
always talk about um do you know the
movie Juro Dreams of Sushi no so there's
this guy who's a he's a master sushi
sushi sh oh my God that's so hard to say
master sushi chef he has a tiny little
restaurant in the bottom of a Subway uh
station in Japan very unassuming and
he's considered um the best in the world
he's got I think three Michelin stars
people wait sometimes up to a year to go
there and in this documentary there's a
movie called Juro Dreams of Sushi that's
amazing in the documentary you see he's
so obsessed with making sushi that he
doesn't allow anyone to cook the rice
but him and people are not even allowed
to touch the eggs until they've worked
there for like 10 years he's very very
rigorous and strict and I think he is a
Craftsman now on the flip side going
back to I mentioned Steve Ellis from
Chipotle well he came up with an idea he
built a machine he scaled it to
thousands of locations he need to wait
10 before touch the eggs exactly but his
life is probably Excel spreadsheets you
know it's it's management it's board
meetings jro he's a Craftsman he spends
all his time making sushi that's what he
loves he's the best in the world and I
think this is the challenge of
Entrepreneurship is often you start in a
place where you love it you know you're
doing a thing you love and when you
start delegating you stop doing the
thing you love and sometimes you can end
up somewhere that you didn't necessarily
expect to end up um it's it's a it's a
really you know it's like one of those
be careful what you wish for things I
know you mentioned that most lessons
most important lessons in business and
life kind of can't be learned through
somebody else they have to be learned
through your own
pain have there been any books or which
are the books when you look back you go
okay that really did sort of expedite my
insight or at least it gave me a
different sort of view uh Michael
Gerbers the emth Revisited for instance
makes me think when you're talking
aboutt about that is there anything else
that comes to mind the eth was huge for
me um I would say most of my most
valuable reading hasn't been business
it's actually been psychology I read a
book called influence by Robert seini
which kind of it's kind of a broad
overview of all of the most common um
causes of human misjudgment and it talks
a lot about how human psychology is
wielded against us in sales and
marketing and so that was an incredibly
Valu valuable book in terms of just
understanding like how do people work
and why you know why do I keep seeing
these uh odd behaviors from the people I
work with that kind of stuff one of the
most impactful books that I recommend to
every entrepreneur is a book called How
to get rich It Is by a guy named Felix
Dennis who was a magazine publishing
Mogul uh British guy and the cover and
the title are extremely douchi so uh
it's called how to get rich and it's him
looking like wearing some very Posh
clothing and he's in this big Throne uh
and he's laughing maniacally and so you
look at this book and you go [ __ ] this
guy don't want to read this um but it's
fascinating because he is a guy who
really came from nothing and started
selling Bruce Lee posters at the time
Bruce Lee was really popular I think in
the 60s or 70s and somehow stumbled his
incompetent way into owning this massive
publishing Empire and making hundreds of
millions of dollars and he starts the
book by saying look I'm going to teach
you how to get rich I'm going to tell
you what I did and tell you my cheat
codes but you actually don't want to get
rich I'm actually miserable I'm old and
miserable and I wish that I'd become a
poet when I was 35 because I had enough
money to do so so I find that is one of
the most fascinating books because it
really drives home the fact that you
don't
necessarily want the thing you crave you
know most people think they want to get
rich when really they just want to make
500 Grand a year or a million dollars a
year uh they don't need to go be a
billionaire to achieve that and in fact
being a billionaire has tons of weird
downsides that nobody thinks about and
so his book was yeah really helpful at
inverting for me and I didn't listen to
any of the advice cuz he I went what do
you what do you know old
man yeah payback for you in other news
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and
mw20 a
checkout what does never enough to you
well it's a phenomenon that I see in
everything um you know if you think
about um when you talk to people and you
say do you have enough money I started
asking people this maybe 10 years ago do
you have enough money and I found that
people with
$500,000 always said well I'd like a
million and then you'd see people with
10 million they'd say I want 20 you see
100 and they want 250 and so on and so
forth and as I continued to meet more
and more successful people until I got
into this really upper echelon of
business people where I'm meeting people
that are worth you know
2520 billion do I noticed that they were
still
striving and I remember I was having
this conversation with a billionaire and
they said um oh man uh Jeff Bezos he's
so rich and I said well what can Jeff
Bezos do that you can't you know this
person was worth 2 billion or something
and Bezos at the time was maybe worth 40
and he just goes he can buy a super
yacht and I was just like what a
bizarre world right that you're still
striving you can buy a crazy yacht and
you just can't buy like an extra big
yacht with like four helip pads in a
tennis court and you're feeling hard
done by and I realized that the reason
that he felt hard done by because is
because human nature is comparison and
he was existing in this weird world
where he's the poorest guy in the room
sometimes right if you live in the
Hamptons being a billionaire is kind of
run-of-the-mill you really want to be
more like Bezos um and I just found that
profoundly depressing as I observed it
and I observed it in myself I could see
in these people and I could judge them
but then when I actually looked inside I
was the exact same way um and so the
book is really me trying to Grapple with
that and ask the question of like okay
well when is it enough and then not only
that but what do you do with it you know
you build all these money machines and
you have this byproduct of money well
what do you supposed to do what's the
ethical thing to do with the money is it
is it okay to buy a super yacht or is it
better to you know give it to children
in Africa can you buy a super yacht and
give it to children in Africa like what
do you what do you do here uh and so
it's yeah it's my journey going through
that crazy
experience what does it feel like to
become a billionaire um well well I
remember the moment that I did the
mental math I was sitting reading
Captain Underpants with my kids and my
phone dinged and I saw you know it was
my business partner telling me that we
had received an unsolicited offer on one
of our businesses and it was a pretty
big number and I I did the math in my
head because at the time we're private
there's no stock price and uh and I went
oh my God that means I'm a billionaire
and then I felt exactly the same and I
went on reading the book with my kids
um and I had the same weird moment where
you know I took my company public about
a year ago and I was standing in line uh
in a coffee shop and I saw the ticker
pop up and saw this huge number in my
trading account and I realized you know
to my point earlier about
Bali you know brain chemistry is the
same still going through the day uh you
know I'll never forget I had a Irish
client this guy Jerry Kennelly lovely
Irish gu great Irish name awesome strong
Irish name and he is from the south of
Ireland in county Cary and he invited me
there for a meeting and so I went down
to to this tiny little Irish town and
everybody knows each other and he's like
the capitalist mayor right he's pointing
out he's like I own that building and
that building and that building and
everybody I could just see um Accords
him so much respect uh everyone's saying
hi to him and stuff and at this point m
career this is probably 15 years ago um
I wanted to be him I was just like oh my
God this guy has it made and I asked him
we sat down in a pub we ordered some
beer and uh I said what does it feel
like what does it feel like to have all
that money and all that success and he
just goes well I'm drinking the same
pint you are and I was like oh my God
like this is you know he I didn't want
to hear it it's like the sad truth of
like people who have a lot of money
still fight with their spouse they still
make awkward small talk with the Barista
they're still anxious they're still
dealing with you know issues at home and
their kids and the end of the day like
the money doesn't actually do anything
in fact it magnifies the misery in many
ways why well I think that when you have
a large amount of money it becomes a
burden right I think that um I'll never
forget there was a client uh what my my
agency metalab had a client who is a
very very wealthy person and they were
doing a lot of
philanthropy and I had breakfast with
this person and on the day that I had
breakfast with them uh there had been a
school shooting and I'd read the news
about the school shooting and I thought
it was really really sad and terrible
but I was able to move on with my day
because you know it was a far away
problem and they were profoundly
affected by this problem they were um
really really shook up and I started
asking like oh you you
know this is really upsetting like what
what's going on for you and they said
I've been working on gun rights for the
last five years um I was trying to pass
a bill to ban the weapon that was used
in that shooting and I think that is the
part of the burden I think if you're a
good person and you have a lot of money
you see problems in the world and you
sometimes foolishly sometimes
realistically believe that you could
have actually solved that or made that
go away think that someone like Bill
Gates hears about climate change and
goes oh my God like I got to figure this
out whereas you and I we hear about that
we go H you know nothing I can do about
it right so I think that's one piece and
then the other piece is um the
management of it you know it's this big
thing that you have to have people to
manage and and people are constantly
trying to get it from you and manipulate
you in various ways to get access to it
um and then it also perverts
relationships uh in the book I talk
about how you know when I first made
money I I was always um I was always
kind of a mooch in high school um you
know I'd be the kid who's like hey can I
borrow two bucks I need to go buy a
Pepsi or something like that and so when
I started making money I really wanted
to pay it forward and be generous and I
found that if I went out for dinner with
a friend and his girlfriend for example
and I didn't pay for the bill I was
being a dick because I'm rich I should
pay the bill but if I did pay the bill I
was showing off and I was trying to put
him down and so I find that there's many
of these catch 22s around wealth where
if you do philanthropy and you talk
about it you're a douche because you
should just be humble and not talk about
it and if you don't talk about it you're
criticized for not doing philanthropy
there's just so many of these weird
issues like that around money and it
really is a perverting force uh in your
day-to-day life and then even as you
have kids and family I think it can
really cause Strife within the family I
mean we've all seen succession uh that's
an extreme case but I think that a lot
of wealthy families are torn apart by
money why what's happening there I think
that um the kids can't individuate they
are living based on who who is in the
good graces of the parents and who's
going to inherit the money and I think
that there's a lot of it becomes like a
court you know it's like a royal family
or something like that who's going to
who's going to be the King and who's
going to take over the business and
who's going to inherit what and even
something as simple um I was talking to
a wealthy friend and I have this
beautiful lake house that is like my
special place where I escape to with the
family and I said I'm so excited that
when my kids are older they're going to
have this for their kids and he said
well are you sure you want to give it to
your kids because typically what happens
with these vacation houses is you give
it to your kids but then they have the
grandkids and then the grandkids can't
agree on what to do and who gets the
house and then they all start fighting
and he had told me a story of another
family that actually had this huge Feud
over their vacation property so I just
think that there's a lot of these odd
second order consequences that people
don't think about you're sewing the
seeds of future Strife by doing
something that in the moment feels good
totally yeah I mean it's so fascinating
to me to hear these stories and the
internet really has a problem with it
which kind of makes me a bit
um makes me feel uh annoyed it
frustrates me that uh hearing stories
about people who seemingly have it all
together financially and say and I'm
still miserable and my son killed
himself and I am on a ton of drugs or
I'm dependent in this way or my
relationships are breaking down or
whatever the response to another human
saying I am suffering is not I'm really
sorry that that's happening to you it's
look at all of the things that you've
got this isn't true you know how what
chattering class luxury belief [ __ ]
is this that you know do they not know
there's people that are starving and so
on and so forth uh I have come to
believe that this is a lesson the money
and success won't make you fulfilled the
external validation won't fix the
internal void uh that that is a lesson
which is in the category that we talked
about earlier on which is one that
cannot be learned without experiencing
it well I would assume it's a lot like
Fame right you know you probably have
people that are stalkers or you've had
you know I'm sure lots of weird
experiences and then you get recognized
all over the place and I bet sometimes
you're sitting in a cafe and you just
want to have a quiet moment to yourself
but three or four people walk up and say
hey I like your podcast and in a way
that's a privilege and that's wonderful
but it also is a double-edged sword it
comes with how grateful how ungrateful
to to say that this is something that I
don't you you you [ __ ] did this I I
wrote this a little while ago and it's a
strange inflection point and it has been
the last probably 18 months for me
personally that that has been the period
that I've gone from like absolute sort
of nobody nobody to now degenerate Niche
Micro Niche influence of fame or
whatever it is uh and if I'm outting
about walking maybe every 15 minutes or
so someone will say something nice dude
love the like a Amazon driver will lean
out of the window Chris love the podcast
it's really lovely it's really cool but
it is getting just the the last week was
the first time it ever felt like it was
a tiny bit much like it was just almost
everybody and you know again this is
what a luxury problem to have all the
rest of it but almost everybody on the
planet has less money and less Fame than
they would like they want to be richer
and better known and therefore all of
the sympathy flows down to the people
that have less the total addressable
market for sympathy is basically zero
also the total addressable market for
advice is basically zero there's an
unlimited amount of content on the
internet about how to become rich and
basically none about how to be rich
unlimited amount of content about how to
become famous and nonone about how to be
famous and quite rightly the people who
don't have the thing don't have the
thing and they not worthy of more
sympathy it's like well yeah but there's
still suffering that happens up there so
in your again you have managed to I
guess straddle groups of people who are
rich people who are famous and people
who are rich and famous how does what
what's the reality Distortion of money
compared with Fame status and what about
when you throw those two together how do
you think about that well um Morgan
howel has this great um it's like I
think it was just a podcast that he did
where he talks about what you really
want is to be rich and Anonymous there's
a great Bill Murray quote where he says
something like if you think you want to
be famous try being rich first and see
if that covers it um and I think there's
a lot of Truth to that and I'm
experiencing that in a much smaller way
than you are I have you know
250,000 Twitter followers now and I get
recognized from podcasts here and there
and at first it was this really lovely
thing where I made new friends you know
I'd be sitting in a cafe and someone
would turn over and say hey I'm an
entrepreneur I heard you on the podcast
and it was very positive and then you
know I just you naturally just meet
interesting people now about a year and
a half ago two years ago I walked out
onto my back patio and my house and I
live in a very secluded part of um the
city I live on the waterfront it's very
very hard to access and there's a man in
my backyard and he's staring at me and
he tells me that he really needs to tell
me about his business idea and I am
[ __ ] terrified I you know give him my
email really quickly and say hey I'd
really prefer if you email me and I go
back inside my house and about an hour
later I get an email from him and it's
not completely deranged and I'm like
okay few this is just an entrepreneur
who's taken hustle a little bit too far
um so the next day uh I dro dve out my
gate and my gate opens and at the end of
the driveway same guy fist bared Furious
that I didn't respond to his email yet
and I just sped away and called the
police like I was totally freaked out
and that's me barely being famous right
I can't even imagine what legitimately
famous people are dealing with um you
know you mentioned that thing of like
you need to always be in those moments
too you always need to be grateful and
recogniz that you know to this person
this is an exciting thing or whatever
Jennifer um what's her name from Hunger
Games Jennifer Lawrence Jennifer
Lawrence told a story where she goes I
can be a princess to 99 people but I'm a
[ __ ] once because I'm in the middle of
a fight with my boyfriend and I'm a
[ __ ] forever and everyone's talking
about it on Reddit I do not envy people
who are famous and ultimately I think
being famous in a niche like I think um
being famous but Anonymous like imagine
the Cen Brothers you know the name you
know like Joel Cohen if you met him
you'd be like oh my God he's so
incredible and if he goes to a film
conference he's amazing but if you walk
by him on the street you wouldn't
recognize him to me I think that's
actually the optimal amount of Fame in
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docomond wisdom and modern wisdom a
checkout uh my housemate's a big
musician and he said LCD sound system uh
as a good example I think they headlined
some huge fast was Coachella or
something like that you know they played
some obscene a country's worth of people
and that dude could have easily got off
stage and walked through and no one
would have known who the [ __ ] he was
looking dude um do you think about that
with yourself cuz your face is
everywhere on YouTube and with YouTube
especially you can go down rabbit holes
right so you know if you talk about one
top let's say you mention the Deep State
randomly it's like you could go down the
algorithm and suddenly you have deep
State people you know it's like you just
have you experienced that yeah it's uh
it's it's an interesting challenge like
this transition has been interesting and
I think I have quite a naturally anxious
disposition as well um very
hypervigilant around sorts of things so
great at problem solving uh great at
coming up with designs for products and
making sure that all of the grammar and
stuff is is perfect uh not so good for
relinquishing this ambient sense of
surveillance that you kind of just feel
is following you around and uh you know
I've really tried to be as open as
possible with the audience without
triggering the must be nice sort of
response but I I feel like if that's the
first thing that you come to when people
a few steps down the path that you're
trying to get along tell you about
Thorns that they've encountered if your
primary responses must be nice as
opposed to must be
interesting I think that I I just don't
think that you belong here like this
isn't the show for you this isn't the
audience for you this isn't the
podcaster for you but it has been very
interesting um to make that change and
to sort of reflect on what do I actually
want what makes me happy um because I
think we look at you know Jordan
Peterson's a good example right of
somebody that was kind of plucked from
obscurity this sort of Dusty academic
working in Canada and then you know from
201516 through to 2019 just has this
obscene amount of growth probably
quicker than anybody else of that ilk
and people are very passionate it's not
just like I don't know being a pop star
or something which has it the kind of
obsession about it but not maybe the
emotional connection they don't feel
philosophically connected to you know
some dj's music or something like Testo
walks through a club would it be cool to
get footo with Testo yeah but like do I
actually have an opinion on Tiesto as a
person probably not and
um I I really do think and I assume this
as well that at some point on the
journey toward becoming either as rich
or as famous or as powerful or whatever
as you want that someone stepped in and
gave you some sort of training course
that there was like a guy that came to
your door and knocked and said hello sir
I'm here to explain to you how to deal
with all of those things you go you're
just the same person that you've always
been you've got all of the same concerns
and idiosyncrasies and fears and and the
other side is you see yourself the same
you see yourself like the same person
but the world sees you as something
different I the uh documentary that was
done I really really enjoyed sort of
famous famous Scottish singer in this
documentary was done on Netflix and you
know he's trying to write the second
album and he's really really struggling
and uh you know Universal Studios are
stepping on his shoulders and saying you
really need to get this sorted we need
we need this to be good and uh he
develops a nervous tick and he's got
this it's Lou Capal and he's got this
huge huge increase in Fame and uh he
turns to the camera halfway through and
he says Fame doesn't change you just
changes everybody around you and in my
experience based on what I've seen that
it it's probably not strictly true
because I've I know some people who've
become famous and become more sort of
assholish than they were previously but
for the most part it's this huge sort of
discordance between who am I how do I
see me the exact same who am I to the
world how does that see me totally
different it's one of the scariest
things I think about um wealth or fame
is that people will behave differently
than they would otherwise I always think
back to um when I was in high school I
had a really rich friend and I noticed
he was a nerd him and I the reason we
got along is cuz we're both into
computers and I found that the way that
he was treated by the Cool Kids versus
the way I was treated was very different
and I always found that weird and then I
realized I was like oh my God it's cuz
he's rich and like they want to go to
his house and he's got Nintendo and a
pool and all this great stuff and um I
think my fear inside is that I'm going
to be treated differently like I noticed
that people who were kind of dicks in
high school now will suck up to me or
try to sell me realis state or you know
a car or something like that and so that
is the weirdest part I think is and
there's you know what's that what's the
Drake song or whatever it is no new
friends right I think there's a lot of
Truth in that that's the sad part about
it it is and I you know I asked someone
I've asked a lot of people this question
because again the total addressable
market for advice on how to deal with
things like this is basically zero uh
and the total number of people that you
can learn from is also basically zero um
I asked a couple of people about okay
what's the solution given the fact that
you have this reality Distortion field
that follows you around what do you do
well then you end up hanging out with
only other hyp successful wealthy people
or famous people because they understand
your problems and the fear there is you
end up in a bubble and you have no sense
of what reality is yes so it's like this
sad reality that as people become more
successful or wealthier they just only
hang out with people in that world
compare themselves to those people feel
sorry for themselves and want the
treadmill which keeps it going keeps it
going keeps it going yeah yeah I
mean am I right in saying therefore in
your experience that the honic treadmill
just runs all the way up even the not
Point not not 1% of people still don't
feel like they've got enough still going
yeah and even even though I wrote the
book you know I know it all I've been
through it I know what I should do but I
still have the dust bow farmer in my
head saying what's next how are you
going to achieve today um how could you
lose it all what could go wrong and I've
noticed that you know if you have
anxiety it's like a a homing Beacon
looking for problems and if the
financial side is solved let's say that
you've gotten Super Rich well then you
go to health right I mentioned before I
started obsessing over Health um
sometimes you become a prepper or
sometimes you get obsessed with politics
or whatever toxic garbage you like to
consume and so um yeah that energy is
going to go somewhere what else have you
found as a prophylactic against the
honic treadmill Beyond ssris make sure
that you train make sure that you eat
well and get ate out of sleep at night
the biggest thing is awareness I've
noticed that um people are stressed out
only by problems they're aware of so if
you think about the human brain 500
years ago if you were in a tribe or not
a tribe if 500 years ago if you're
living in a village um you'd be a aware
of your neighbor problems and you'd be
aware of the problems that affect your
village and at any any given time
there'd be a couple problems and I think
the problem with the Internet is that
our brains are not designed to be aware
of all problems globally at all times
because I think it can create a
narrative that things are terrible when
in reality the it's not that things are
terrible it's that things are always
terrible somewhere some at some point in
the in time and so the way that I cope
is actually by not looking at news not
allowing myself very much social media
um and being very very cautious about
how I work and when I work so I actually
treat myself like a drug addict I say um
you know if you were trying to get off
alcohol you wouldn't keep a bunch of
alcohol in your house so for example I
have my phone locked down and limited
and my girlfriend has the password to
screen time uh I can't do email on my
phone I can't look at news the screen
just goes blank when I do what app are
you using to control that screen time
and opal so for example like Twitter has
been a wonderful thing for my life and I
really benefit a lot from it but left to
my own devices I'll go on it endless
endlessly and so I allow myself five
sessions a day and then it's over and
after a certain time of day I'm just not
allowed to use it and so by drawing
those boundary boxes around myself I
find that my mental health is better and
that I'm less stressed and I think that
ultimately one of the most challenging
things about being public so for example
having a public company is that your
stock goes up and down like yesterday I
lost $50 million on paper right and it's
like you know I didn't to to reassure
you I didn't feel anything right it's a
number it's a number and I was talking
to a friend about this the other day and
you know if you own a house your house
is probably your biggest investment for
most people your house goes up and down
in value every day you just don't see it
you're not aware of it you're not
getting it revalued every day there's no
stock ticker and so I think ultimately
my goal is to have as few tickers in my
life as possible and what I mean by that
is like news social media anything that
can go red or green things are good or
things are bad I just don't want that I
want to be as present as possible and
only think about what I want to think
about in the moment not allow those
things to hijack my brain it's
interesting sort of thinking about the
the brain of a hypervigilant person that
you can worry about things that you
don't yet know about you're you're able
to invent worries quite well but if you
artificially inject a bunch by exposing
yourself to news or by having a lot of
different things that you're tracking in
one form or another uh that is a it's
like oh this fire is burning might as
well throw some kerosene on it as well
uh it's very interesting to sort of
purposefully restrict what you're
exposed to especially if you're a
curious person as well if you want to
learn things you go okay well how can I
sift through the [ __ ] that makes me
feel bad but look at all of the like
these little slivers of gold that I keep
on getting or you know it's good for
connecting with people able to grow my
business and maybe I'll get to speak to
somebody that I really respect and
that'll be fun uh but yeah finding that
balance I think is is very very
important there's a great book called
dopamine Nation by ANM show awesome and
I love this idea that the way the
dopamine system works is is that you can
get addicted to anything whether it's
chocolate cake or heroin or the example
she gives in the book is vampire novels
and I think if you're a anxious person
it's very easy to go down the rabbit
hole and get hooked into anything and
for me it's like Health podcasts if I
don't restrict my Access to Health
podcasts I will start beating myself up
every single day that I'm not doing my
V2 Max training and I'm not taking S I
did my Norwegian 4x4 this morning
exactly right there's always something
and
and yeah I think that you really have to
be very careful about what goes in think
of Andrew huan's RPM like you are
negatively impacting how much money
money he makes from his AdSense account
so maybe you do need to start watching
again you just leave it on in the
background and make sure that you keep
on he keep on paying him that sweet cash
but yeah man I uh I I really do think
this this sort of insight
that we are hopelessly outgunned by the
amount of information that we're getting
in we are hopelessly mismatched mentally
psychologically our predisposition our
source code as humans is not built to
observe the entire world's news and
catastrophes 24 hours a day fed directly
into our brains and then for us to
actually be able to respond and that's
when you see people that blow up because
you just have this frictionless brain to
fingertip to World filter where people
toilet tweet things that is observed by
the rest of the planet as some
indication of exactly who they are oh
you know this is a synthesis it's like
dude he he slept 4 hours last night and
was you know taking a dump in between
two flights in in Barbara Jordan Airport
terminal or whatever like it's not that
at all but just leverage Works in both
ways and I think that you need to be
very cautious about what your sort of
leveraging into yourself as well as how
you're spending your
efforts I
wonder when it comes to we we talked
before about kind of how programming
changes the way that you look at the
world
uh Puritan work ethic coming from
particular backgrounds what's your
Insight on how childhood experiences
impact your view of money of uh wealth
information of the way that you relate
to to wealth and making money and stuff
like that well I can only speak to my
own experience but what I've seen is
that whatever whatever is put on a
pedestal or whatever is a problem when
you're a kid I think it's hard-coded to
you and money was a four-letter word in
my house I mean my dad was um an
entrepreneur and struggling and he was
optimistic and chaotic and you know he's
the kind of guy who would say you know
what like let's just buy a family
computer for $2,000 and we'll put it on
credit and my mom is like a total
hardcore budgeter spend Thrift we
looking at our finances and saying we
can't do that and so those two things
they created this like you know vinegar
and baking soda
explosion and all I knew that would make
my parents happy and make them stop
fighting and to be clear they weren't
you know they're not screaming at each
other they're just fighting there's
friction in the household um I felt that
okay I'll just pour money on this and
that'll resolve it um and so that was I
don't know that's somewhere deep inside
me this idea that money is the solution
to problems and obviously I have a very
different perspective but even as we
speak today when I think about
protecting myself or when I think about
problems I always am thinking about how
can I use money to stack you know to
stack up a wall of money around myself
so nobody can make me do things I don't
want to do or how can I ensure that I
have money tucked away if I ever need it
for this emergency or that emergency or
whatever it is so um yeah I do and and I
am I'm very grateful that you know it
wasn't that my parents were alcoholics
or hitting each other or whatever it is
because something different would be
hardcoded for me then and you know maybe
I'd be more like Elon or or maybe I'd be
dysfunctional in doing drugs I don't
know yeah um that's that's what I find
so fascinating about you think about
capitalism and we talked about machines
earlier right well capitalism is a
machine that takes crazy people and
greed and builds benefit for all of us
right I find it so funny like the same
people that hate Jeff Bezos to be clear
Jeff Bezos I believe he was an orphan or
he was uh I believe his uh his dad
walked out on him when he's very young
like so many of these complex
billionaire types have very difficult
stories very traumatic childhoods and
they'll criticize someone like Bezos or
Elon and then at the same time they're
still using they're driving a Tesla and
their love Amazon Prime and they don't
seem to make that disconnect of like
okay that crazy person that went and
blew their brains out that we all hate
on created all these wonderful
innovations that we all appreciate today
and I think that's kind of what's
wonderful about capitalism and that
people Miss it's this engine for human
greed and suffering that you know does
great things we'll get back to talking
to Andrew in one minute but first I need
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matter what stage you're in yeah that is
very interesting it's like Alchemy in a
way you know you take this thing that
left to its own devices without
capitalism would disrupt the local tribe
or would cause some sort of catastrophe
would just be misery for for that one
person but now that person's misery can
be mutated into benefit for many for
many other people Downstream yeah well
even like think about um narcissists and
Psychopaths right because I I've had a
few run-ins with various challenging
personalities dark Triad types and um
you know they're really scary but they
may have a there may be a reason they're
here right you know it might be
beneficial to have somebody do a crazy
thing like that because who else is
going to do it but for a psychopath or a
narcissist and I do think some of these
people who are hyper successful do
follow that pattern as well I don't I
don't want to say everyone's anxious
what I've seen is people are either
anxious and anxious planners they're
narcissistic or they're Psychopathic
those are kind of the the AR the three
most kind of common traits of successful
people the hyper hyper successful people
to be clear I've met a lot of very
success uccessful wealthy people in my
experience most of them have been lovely
you know I read about in the book this
experience of going on a trip down the
west coast and meeting progressively
wealthier and wealthier people they were
all really nice in different ways and
they all have great businesses but in
the book I talk about how they're all
still just miserable and frustrated and
adding zeros who's got it right the most
right of the people that you've met to
say this is someone that I think has
achieved a degree of success but also
they've just you know they're there
their mind rests where their feet are
they've found presence to me um well so
I was in New Zealand and prepping no
kind of kind of actually kind of I I the
only reason billionaires go to New
Zealand yeah I actually was in New
Zealand for a it was a conference
relating to getting citizenship so yes
guilty as charge impr preing I do love
New Zealand though um but anyway I was I
was thinking about who do I know in
Wellington where I was staying and I
remember this guy that I'd met named
Derrick cers are you familiar with Derek
he's been on the show yeah he's amazing
and uh I had met him and he had been so
kind to me when I was a I was a brand
new I was a young pup I just started my
company and I met him at a conference
and he was just so kind and engaged with
me and uh hadn't seen him in almost 20
years so I looked him up and we went
over for coffee and I didn't actually
know that much about him um I knew that
he had sold his company but I didn't
really really know how he' structured
his life and stuff and he basically I I
was opining about everything I was
dealing with and all my stress and
running the businesses and all the
complexities of money and he said well
when I sold my company CD bab for $20
million I put it in a
trust and the trust pays me 5% a year
but I can't access it so I don't have
the burden of the money I just get the
5% a year from index funds and municipal
bonds or whatever it is but it's not his
money and he can never get it back and
he said I didn't want to play the same
game again I had gone and I had done
entrepreneurship I'd started a company I
had won Gold and my brain was telling me
you got to win gold again you know and
it's like one of these things where it's
like if you win gold you win gold like
you made it you don't need to prove to
everyone you can win it again but I
think a lot of us go they they want to
keep playing the same game and winning
over and over again fluke no exactly and
so Derek said you know what I'm just
going to write I really love writing and
I'm going to Tinker and start new
businesses but none of it's going to be
about money I'm post economic and he the
way he put it to me was I burned the
boats you know I really drew a
demarcation in the sand where I said I'm
done with money it's tucked away it's
not my money anymore and I just get
enough I get I think it's a million
dollars a year or something which is a
hell of a lot of money it's awesome um
so I admire I admired Derek a lot
because he spends his time thinking and
reading and meeting and trusting people
and writing about his thoughts and he
still Tinkers but he's taken away money
from the picture which I really admire
and I can think of a few people um like
that and I think that the people I
admire the most are actually people who
prioritize relationships that are friend
billionaires not billionaires they have
a huge broad collection of interesting
people that love them and that they love
and they have great families you know
those are the people ultimately which is
such a Cheesy answer but those are the
people ultimately that I admire I
think so interesting man I really wonder
what whether or not it's ever going to
be possible
to preclude a war everybody you know
myself included under you uh about
chasing down something which is like
running toward the Horizon that each
step that you get toward it is it gets
one step further away Morgan howel says
that the only way to win the game is to
stop moving the goal posts it's like
okay the first thing that you need to do
is okay where am I going to get to and
at that point stop but how many people
get there and go well you know if I've
managed to make whatever this number is
or I've got my first house or I've got
the H the dream house I want to get it's
like yeah but it could be a little bit
bigger yeah there could be a second car
in the driveway what about a holiday
home I wonder and I I've been thinking
about this a bit recently as well to do
with capitalism it's such a [ __ ] good
game man oh my God is it a good game so
many people have been
turned
from the ancient Greek word for work was
translated as not at leisure so the
ancient Greeks are workers an aberation
and Leisure as the set point and now in
the modern world we've sort of done the
opposite we have
uh this productivity Purgatory where
even the walk that you do on a morning
isn't to enjoy being in nature it's
because Andrew hubman told you that
you're 10% more productive if you get
sunlight in your eyes for the first 15
minutes of the day or whatever and uh
yeah I just wonder I wonder about all of
the different ways that we can shortcut
that realization to get to maybe you
should stop working so hard there is
absolutely a group of people out there
who are uh type B personalities that
don't have a leverage problem they have
a work ethic problem and they need to
just step their foot on the gas but
there's an awful lot of people most of
whom will be listening to this podcast
who are type people who don't have a
work ethic problem they have a leverage
problem or they just have a chill the
[ __ ] out problem and trying to get them
to some sort of a stage I I don't know
what it is if we could inject something
into the water I wonder whether um this
sort of new generation of uh glp1
agonists Downstream uh will maybe have
an impact on this they definitely seem
to be able to uh change a lot of
obsessive Behavior social media
addiction gambling addiction uh
marijuana addiction uh and a couple of
friends mutual friends of ours are using
sort of Second Generation and third
generation versions of these and
a couple of them have said to me that
stuff that they didn't think at all
would be associated with this the amount
of time that they spend scrolling
Twitter has gone down one of them said
it turns out that willpower is a drug
and the dosage is around about 25
micrograms per day or something like
that uh so maybe that'll step in you
know maybe we're going to be
pharmacologically sort of nuted away
from this but I don't know I I I really
do hope that there is a
way selfishly for myself to be able to
see okay and where's enough and what
does that where does that where does
that end because it is a bottomless game
like yeah I think with money um not
enough people think about what the
number they want in terms of income
should be every year and I think if you
you know Derek was like look okay I make
a million dollars a year and that's more
than I ever could spend and that's a
great amount of money but if people
worked backwards from there instead I
think they could aim a lot lower and
probably have much happier lives and say
I don't need to go and start the next
great billion dollar business I'm not
damaged enough for that I don't have
enough trauma and instead I'm going to
go out and you know start a pipe fitting
business or I'm going to own a bunch of
chain restaurants or something like that
um I don't believe that people um have
any awareness of what's going to make
them happy in the end and with money I
think that they they really are just
moving the goalpost that um they they
don't think about what is actually going
to to derive real lasting benefit they
think about adding the cars and the
boats and all that stuff and you know
I've explored all that stuff I've bought
silly cars and I've chartered yachts and
all that and you know really it's all
empty because you adapt to it just like
anything else I love the idea of the
glp1 inhibitor to my point of you know
if you if you are unhappy sitting alone
in a room you know why would that be
different if you're in another part of
the world
whatever and you know for me taking the
SSRI has been helpful on the anxiety
point but I do wonder about taking a gp1
inhibitor now you got me thinking maybe
I will yeah I think
it's when we look at people that are
diabetics we don't say why can't you
just work harder to process insulin but
because everything else has some degree
of willpower depending on how determin
is imped you are some degree of
willpower and and agency that we have
over that so we just assume that
anything that's a shortcut is bad and
you I'm big into agency I'm big into
people doing things for themselves and
not relying on external buttresses and
stuff like that
but the way that everybody should look
at the richest people in the world or
the most successful people in the world
is as this bizarre manifestation of a
pathology it's like wow I wonder what's
broken inside of them that caused them
to do that thing you
can't you can't hope for Extraordinary
outcomes without having extraordinary
inputs but this is this is not only true
in in wealth and business but think
about artists think about you know Amy
wiin housee was bipolar Kanye West is
bipolar Salvador do you know Salvador do
all these amazing artists and really
really [ __ ] up people create amazing
things it's just that Thomas Edison
didn't have Twitter right he wasn't
posting from the toilet at 3 in the
morning he was probably just as insane
as Elon Musk and you just didn't have
access to him he was a black and white
photo in the newspaper and for all we
know people did think he was crazy back
then who knows and for all we know he
may have been miserable tot he went to
bed on a nighttime
totally yeah it's
uh you said before about uh people don't
change um dig into that a little bit for
me sort of what have you what have you
learned about that given that you are
trying to change yourself you want to
become better yourself but what have you
learned about the human capacity to make
changes so um this is mostly been in a
business context but I found that the
path to misery is trying to change those
around you um and I've found I've hired
a lot of people and I've realized that
ultimately when you work with somebody
you are ultimately the rider on an
elephant the elephant is really big and
it's going to go wherever the hell it
wants and you can maybe put some peanuts
down and hope that they go in the
direction that you want but no amount of
you know hitting it or doing whatever is
going to affect that the elephant is
going to go where the elephant is going
to go and so I have just accepted that
um you know generally when you like like
let me let me tell a story so um we had
a
CEO and they said uh you know I want to
go and I want to pursue this strategy to
grow the business and I said well we've
tried this before we've you know we've
already done XYZ here's all my Logic for
why it wouldn't work now psychologically
when you challenge someone directly they
double down so often if you let's say
you said you're a trump supporter and I
said well Trump's stupid and he's a
criminal and all this stuff you actually
are going to double down on your belief
and Hammer it in and so you know what I
used to do is I would go back and argue
with this person and try and change them
they would say no they'd double down and
then I would wait a year and they would
try the strategy and it would fail and
then I would try not to say I told you
so and I would except that the person
had to learn the lesson on my watch on
my clock and it was going to cost me a
bit of money but ultimately they had to
hit rock bottom they had to get to that
point where they realized that it didn't
work and then if I intervened they would
just be like oh my God Andrew swooped in
and he took away my agency and it would
have worked and I hate him so I've seen
that in business and then I've also seen
it in my personal life I found that very
rarely can you go to somebody and say
Here's a big list of all the ways you
need to change and just have them go and
do it I think ultimately you need to
watch them fail like the kid falling off
the dock they have to go and hit a
Breaking Point or get called out by a
friend or have something bad happen and
then maybe if you're really lucky and
their self-reflective they'll change a
bit I was going to say even after
failure how much change have you found
well even then I think um it's rare that
people will blame themselves I do this
myself right I I will always have a
narrative at as to why something I did
didn't work and how it's other people's
fault and I always need to check that in
myself I think that um
generally uh you always have a
charitable picture of yourself you know
you know what your intentions were and
you went in and you know you were trying
to help this person and then there's a
misunderstanding and a bad thing
happened or whatever it is and we all
build Chari of narratives because that's
how we function you know people can't
function going through life thinking
that they've upset everybody or been a
bad person it's not fun to have your
nose rubbed in your [ __ ] um and so I
think that challenging that protection
um that kind of innate desire to protect
yourself is a hard thing and a lot of
people struggle with that it's a lot
easier to say well the world was unfair
to me and therefore I don't need to
change you tell me that story about when
you lost $10 million yeah um so I was
running my digital agency and digital
agencies are
wonderful businesses sometimes and
really really hard at others so you're
always in this position where you have
too much demand you've got tons of
clients wanting you but you don't have
enough um Staffing in capacity or you
staff up and then the demand goes down
so you're writing this roller coaster
constantly and I heard about all these
people starting SAS software companies
and when you own a SAS software company
you have thousands of people paying you
every single month and it's very very
steady Edy and just kind of goes up into
the right over time and I went okay
that's the business that I want to own
and so I started a project management
software company called flow and we
started basically what was what so
basically we started Asana before Asana
came out and it was very welld designed
and very cool and I funded it all myself
I put you know by this point I put $2
million into it and it was quite
successful in the beginning you know
within six months I think we were making
$2 million a year or something and then
the founder of Facebook left Facebook
and started a company called the sauna
and I looked at their product and I said
we we're better than them you know we're
designers uh we have more Soul we're
we're going to out compete these guys
will be the Scrappy
upstart and um very quickly he raised
$100
million and he built an incredible team
of marketers and salespeople and product
people and they outgunned us very
quickly within two years they had more
features than us a better product
overall and and we were like a fart in
the wind you know nobody nobody knew
about us everyone knew about Asana
because they were buying ads and I was
really pigheaded and I kept saying no
we're going to win we're going to we're
going to bootstrap our way to this and
in
retrospect I was like Fiji trying to
invade the United States there was never
a chance but because I didn't know what
I was doing I had this conviction around
it and I ended up losing $10 million of
my own money which you know if I had
just invested it this was probably 10
years ago if I just invested it I'd have
$30 million more or something like that
uh instead I have zero what was the
lessons that you took away from that um
well I think in business you want to
Charlie Munger and Warren Buffett talk
about jumping over one foot hurdles or
Munger has this great line where he says
my idea of shooting fish in a Barrel is
draining the barrel first right so
finding businesses that are high
certainty where you have a very good
chance of success um and then Munger has
another quote which is fish where the
fish are and the idea there is he talks
about there's all these big fishing
ponds with tons of incredible fish in
them but those fishing ponds attract
thousands of other fishermen and they
all have amazing lures and you're all
elbowing each other he recommends
wandering into the forest and finding
a tiny little pond with great fish but
only a few other fishermen because you
have much higher chances of success and
I think what I was doing there was
fishing uh fishing in the overfished
pond I had too much competition it was
like I own a pizzeria and uh Venture
Capital decided to open 10 pizzerias all
around me and sell pizza for free how do
you compete with
that so you mentioned before about the
difficulty in getting people to change
presumably that means that hiring well
is the most important thing in a
business okay talk me
through the process that you use how do
you think about hires how do you assess
candidates how do you ensure that the
people that you hire do the thing that
you want them to under a good fit so
generally the only hires I make these
days are
CEOs um the way that I do it is I try
and find somebody who's run a same or
similar business um and they've done it
at two times the scale so I'm not
looking for somebody who um let's say
that you know I've got a let's say I
have a pizzeria and I want to franchise
it I don't go and hire the guy from
Pizza Hut who runs Pizza Hut today
that's too big I go and I find the guy
who's got he's currently working at
another Pizzeria franchise that's five
locations or something and then I talk
to them and if I'm nodding along with
what they say they would do do at the
business with no suggestion from me that
is a very good sign because going back
to the idea of an elephant the elephant
is going to go where they go to a man
with a hammer everything looks like a
nail and so if they come in and they say
I'm going to grow this business by
franchising it and I'm going to go to
Five locations and here's where I'm
thinking and I'm nodding along and
thinking this is what I would do that's
awesome and I will rowing in the same
direction totally so the number one
thing is are they rowing in the same
direction and I've learned this lesson
over and over and if someone comes in
and they say actually I don't think
franchising is the way to do it I think
you should own all the locations and I
don't agree with that even if I hire
them and I try and convince them that's
not the case they will sabotage they
won't do that presumably even if that
person's very well credential and super
competent and all the rest of it doesn't
matter they always do what they whatever
their program to do whatever their thing
is and this is true I think you know
everyone has their Hammer um and from
that point on I will make an offer uh I
try and incentivize them so that they
have skin in the game they have downside
um and ultimately if I win they win and
if I lose they lose alongside me and I
think a lot of people miss that they'll
often pay someone a flat salary or
something like that where they wonder
why this person doesn't care as much as
them and often it's about alignment um
that's something that I didn't
understand in the early days I used to
pay somebody I'll never forget I had a
designer who worked for me and I told
him great news we just closed a $20,000
contract and it's we've got all this
great design work and he was kind of
nonplused and I was like why isn't he
excited and then I realized he doesn't
make any more money whether or not we
achieve this it's just more work for him
and so from that point on I started
trying to align people with whatever the
output was what's a typical way that you
structure the remuneration package uh
well it's usually it depends on the
person some people are simple and they
just want cash and so say something like
if we make $2 million of profit you get
a $250,000 bonus or you get 5% of profit
whatever that profit number is other
people say I need ownership I'm
long-term and those people I will often
say Okay um do you have cash let's buy
in you know you can buy into the
business and I'll buy you out if you
ever leave or sometimes I'll say I'll
loan you the money and then you can
invest but I like people to have this
sense that they have actually sacrificed
something I find people don't value
things unless they have to dig into
their own pocket um and then the final
stage you know going back to having bad
experiences with people um now I do a
really really deep background check um
and we have a group of guys who's
actually former CIA that you get private
investigators deep they go really well
it's not really piis but what they do is
they go really far back in people's
history you know did they graduate from
the school they said did they work at
all the places they said they call the
references that aren't given the you
know oh it you know looks like Chris was
at uh Acme Corp but he didn't include
that in his resume let's make sure we
call those people um and you know most
of the time people check out but
occasionally you find out that someone's
sketchy and you avoid them go back for
me where are you finding smart people
what are your favorite uh Pathways to to
find them and then uh what does the
assessment period look like so when I
was starting out I was doing it and I
would just go on LinkedIn and I would
say what are five companies that I
admire that are similar to this business
and then I would look at LinkedIn and
say who's the CEO president coo and I
would just cold Outreach to those people
um over time I've actually started using
recruiters and I hated recruiters I
hated the idea of paying a whole bunch
of money for someone else to go on
LinkedIn but now I look at it as a
leverage point because the recruiter
will go and interview people and I get
them to record the zoom call and then I
watch the zoom recording and I think we
both know like you know within a minute
and then you're thinking oh my God I'm
wasting 30 minutes with this Dingus um
if you don't like the person uh so it's
a great hack to kind of accelerate that
process and what about the uh you bring
them in and getting them to work
alongside somebody is there any sort of
no there's no thr in the pool sink or
swim and I don't mean that in some sort
of like harsh way it's literally just I
want to hire people who are fully formed
don't get me wrong I take chances on
people all the time and when I start
small businesses I will take chances on
some random kid and you know I'll again
I'll throw them in or I might Mentor
them a little bit but when it comes to
CEOs it really is just here's you know
here let's get us aligned um that's like
a magnet and you know let's uh let's
make sure that you are a you know doing
hiring a new CEO is like a brain
transplant for a company you want to
make sure that the brain will not be
rejected naturally the brain is rejected
and so you really have to carefully to
ensure you're a DNA match um but you
know those things being right and then
you know here's what we care about let's
go we just throw them in and don't talk
to them Ben Francis the founder of jimm
shock now currently CEO of gym shock
again after he left and then came back
we were walking through Manchester a few
years ago and I was asking him about his
approach especially for sort of seite
type things and I think his his idea was
uh High well incentivize appropriately
and then crush them with with work load
and he has it's almost like a wartime
General approach to a lot of what he
does that people are close to the best
paid that you would be for this level in
your industry at this time Etc uh but
then the amount of work that is thrown
on you and it's it's as you said sink or
swim it's uh there's a dude called
Bournemouth barbell in the UK he's a
powerlifting coach he only works with
people for free works with people for
completely free but he has created some
of the strongest people in the United
Kingdom for a very long time he's in his
sort of 70s and he does it because he
loves it and presumably he's got enough
money to sort of keep things taking over
but he works with people for free and
one of my friends started working with
him and I like dude that's really
impressive you know you've been selected
kind of thing to invite only sort of
underground hero type guy uh and then I
realized over time why this particular
guy had such great outcomes and it's
that he basically doubled the training
volume of every athlete that worked with
him so in the space of a year you'd made
two years worth of progress now what you
didn't get to see through survivorship
bias was the attrition rate you didn't
get to see all of the people who were
burned out or injured or gave up on the
sport because this crazy guy from the
south coast of the UK was [ __ ]
crushing them with double workouts uh
but what you did see was who were the
victories that came out on the other
side now in a world where the
externality of bringing someone in and
crushing them with a high amount of
workload isn't injury or you know like
the end of their career it's just that
this isn't the right fit for you you
actually can continue to cycle through
until you go okay I found an athlete or
a CEO whose work capacity is so great
that they are going to be able to make
us move at twice the speed or three
times the speed as we would have done
previously it kind of made me think
about that well I think um yes but only
through leverage of other people like I
do want to hire to the point before
about um putting yourself out of a job I
the thing I hate to see actually is when
the CEO works really hard I want a CEO
who's lazy and has built the company
into a machine and don't get me wrong I
want the CEO to be a you know wartime
CEO and run into battle if they need to
if things are looking bad but at the end
of the day I actually really love seeing
a CEO taking vacations working normal
hours because to me that tells me that
their company is actually humming and
they're running it well it's the ones
that are driving maniacally where I go
not using leverage approach they're not
using leverage exactly by definition
what about um what are your thoughts on
using your entrepreneurial gut this is
something that people talk about an
awful
lot I think that your gut is only as
good as your experiences I think my
entrepreneurial gut would tell me to
start every business Under the Sun going
back to I was talking to my friend uh
about the um lunch business right oh why
don't I make kids why don't you know
start a company doing kids lunches well
20 years ago I would have started that
business and been excited about it now I
know how complex it would be how low
margin it would be because I've been in
Food Service businesses and I've seen
similar companies I can go into my
mental models in my head and just go
immediate no right and I think that uh
ultimately your gut is built only from
experience and you know even like
reading like I I'm a big reader I think
reading is probably the number one
recommendation I give to entrepreneurs
if you just read all the time you'll be
fine um but even when you read about
stuff it's not the same as experiencing
it there's been numerous things where
I've read about entrepreneurs who have
done stuff that they've made mistakes
that I I you know go on to make would go
on to make and I still had to learn from
that from actually having the pain right
is that a
uh is that a sad realization you know so
much of what we've spoken about today is
just this kind of endless inability for
humans to learn from the mistakes of
others no matter how cool that quote is
well I think um without the pain you
don't have the motivation so um you know
when I read the emth I was in pain I was
in acute pain I remember specifically
reading a passage and it said uh it was
giving an example of somebody who ran a
bakery and they were staying up all
night baking and then they're running
covered in flour and trying to Peck into
the cash register you know try and serve
customers and it was just such a perfect
picture of where I was at in that moment
that I was just trying to do everything
I was trying to hold up the world um and
so pain plus reading equals success
right you need the pain and you know my
son I um I I play guitar very badly and
I really love the idea of playing guitar
with my son and so I got him guitar
lessons and he just was checked out he
didn't really care he said Daddy this is
boring and I was a little bit
disappointed so we he stopped doing the
guitar lessons and then the other night
we watched School of Rock and in School
of Rock you see these kids and they're
you know they're Mohawks and they're
playing lead Zeppelin and and suddenly
my son is super excited to learn guitar
and I think like you have to find that
moment where you have this passion and
excitement or a problem and motivation
to learn and often the most successful
is the Pain part
right because it's impossible to hide
away from there's a lot of things that
uce you all the time that thing could be
cool that thing could be interesting but
there's far fewer things that are
actually very painful that occur in your
life I mean imagine it's like the way we
teach math today I find it insane you
teach kids math and you don't explain
why they would ever use it right it's
like why would I I'm in finance now and
I got 48% in math 11 I I passed because
I begged my teacher to give me 2% and I
ended up passing uh and therefore I
could graduate high school and today I
know all the math that I was learning in
math 11 and I'm really good at it but I
didn't know it at the time because I was
going why would I learn this it's like
teaching somebody to going back to
guitar it's teaching someone guitar when
they've never heard Leed Zeppelin you
they don't know that you can have a
mohawk you got to hear lead Zeppelin or
you got to be rejected by the girl who
likes guys who play guitar that's the
best motivation so moving forward for
you you know having spent an awful lot
of time thinking about you know the
honic treadmill tuned all the way up to
multiple billions of dollars what what
do you sort of Hope for yourself over
the next few years what are you working
on to sort of presumably you you've kind
of set yourself a a bar that you need to
be reminded of like you've written the
book like you can't it's there's an
obligation right that you have to
yourself now having spent so much time
thinking about what do I actually want
what makes people happy how much can I
keep on trying to uh use the same
solution to fix a problem that doesn't
seem to go away what are you hoping to
do over the next few years well one of
the we talked about learning about
psychology and one of the most powerful
psychological effects is um consistency
and commitment bias so that would be I
tell you um I'm really into rock
climbing or I'm going to get fit this
year I'm far more likely to achieve it
if I go and I tell all my friends and so
I think writing the book was a way for
me to muddle through my own feelings
synthesize it into a book which you know
there's a nice benefit other people can
read the book and hopefully benefit a
little bit from it or they'll be in
acute pain and maybe learn from it um
but then there's also a level of
consistency and commitment in the book I
talk about burning the boats giving it
all away signing the giving pledge you
know and I've made that intention really
clear that I'm going to give away all my
money and you know my kids are not going
to inherit large amounts of money um you
know and I've really made a commitment
publicly so I think part of it um part
of it is that and then also um working
through what to do with the byproduct
right going back to that thing of you
have this it's like having a farm and
the farm creates vegetables and then
they're all just sitting in a warehouse
or something no don't get me wrong they
compound and you know there's all the um
waren Buffett stuff but really trying to
think about what's the maximum good you
can do with this byproduct of money what
about from a personal standpoint a
values a drive what are you looking to
achieve
there I would love
to get to a point where I do not ask
myself what's next um and I don't know
if that's possible maybe if I inject
enough glp1 maybe I can get there but I
would love to deprogram myself you know
I think that I have this very very loud
voice that screams at me every day what
are you doing where how are you being
productive uh what's coming next and I
it really does not enable me to
appreciate what I have in the moment um
I don't know if that's achievable you
know I'm pretty to be honest I'm quite
happy with where I've landed now and I
feel like I'm in a good place but I
don't know if I will ever have enough
mentally you know I me in the end of the
book I kind of say like I'm still going
like I'm still building my business and
doing all these things but hopefully
because I've created more meaning out of
it in that I'm not doing it for myself
anymore because I have enough myself and
now the the you know if I was to write a
second book it would be well what do you
do with it how do you give it away
effectively right and that's what I'm
investigating right now that's what I'm
fascinated by is how do you do effective
philanthropy what is the most s magman
freed he was the guy he was your your
savior and you know wrongly as I think
incarcerated get him out free salon then
he can look after your money you do
great interestingly I uh I read the
Michael Lewis book and I went here's a
guy who is just really odd and uh who
you know it's it's so interesting like
it's so easy to twist Sam bankman freed
and say you know he's this horrible guy
and all this stuff but like so much of
what he was doing was like giving huge
amounts of money away to charity like
who does that if they're like a true
psychopath that wants to do bad things
and defraud people again I mean he broke
the law he
maybe he should be in jail I don't know
I you know I don't necessar I don't know
him and I don't have any um major
opinions there but it is an odd thing
like to hear somebody was committing
fraud to give money to charity that's
kind of a bizarre you know that's like
the I can't criticize that you know as
much as I can someone who's running a
Ponzi scheme to go buy 100 Ferraris yeah
William mccal the guy that came up with
effective altruism uh you know it was
only maybe six months after that that I
I saw him and I thought you know this is
a a philosophy that you championed that
even if you weren't the original
originator of you kind of would at least
the face from a philosophy perspective I
think William was the youngest ever
philosophy tenard philosophy professor
in history uh this kid Scottish guy
really lovely guy and uh you have this
guy that comes in effective altruism
good branding good name sort of does
what it says on the tin and I wonder how
long it's going to I wonder if that if
EA will ever get back to where it was or
whether the sort of FTX s bankman freed
debacle has been so cancerous from a
brand perspective that EA now needs to
be it needs to be something new it needs
to be effective philanthropy needs to be
EP or something like that what a weird
world though where one bad egg ruins
something that's so simple and pure
which is simply the idea of maximizing
every dollar to do as much good as you
possibly can I mean I don't know
specifically what s bankman freed was
funding but most effective alterists are
paying for malarial bed netting and
vaccines or things like that that
benefit people so massively I think it's
kind of crazy to criticize something
like that I think the problem or at
least one of the reasons there was
fertile ground for criticism is that a
lot of people in EA it's sort of it from
the outside it seemed almost
purposefully
uh obusca it was kind of a holier than
thou speaking down from on high there
was sort of in lingo it was you know it
was a high IQ uh [ __ ] movement well
any movement that says how dare you buy
those shoes you know let's say you have
a $1,000 shoes how dare you buy those
shoes how many malaran could have saved
could have saved a life right I think
it's gonna be judgy yeah yeah
interesting man I you know it will be a
shame if there is
no uh better version of of Charity that
is done uh you know Warren Buffett
Charlie Monga yourself eventually these
big chunks of cash are going to get
passed down to somewhere uh and if we
don't have a better vehicle to pass them
down to it's I mean you know this is the
big this was the big criticism the EA
came out of which is look at where your
dollars go when they go to normal
Charities I think the last time that I
checked maybe effective altruism had
eight or 10 charitable organizations
that met its criteria of does what it
says on the tin actually does the thing
give the money is used in an appropriate
and responsible way and there's not an
exec island where all of the guys are
just business expensing their way around
the world and you know being sort of
super frivolous with things and you go
oh that's kind of sad in the United
States um you know you might you might
have experienced this contrast between
England and the United States but my
friends in England and say when you tell
someone about an idea in England they
say why would you do that right why
would you take that risk and in the US
they say that's incredible right there's
a a culture of excitement and failure is
okay and I find it so interesting that
in entrepreneurship failure is okay but
in philanthropy no amount of failure is
okay they point to that one example
where there was a fraud you know there
was a fraud and people donated money or
they over spent on marketing or whatever
they the gacha moment is and then they
cast that net across everything and that
same thing is true with EA with bankman
freed where it's like look there's I
know people who are big in EA and
they're lovely people doing incredible
work and saving a lot of lives and I
can't criticize them and just because
somebody who is a bad egg potentially
you know gave money there it doesn't
doesn't ruin the whole bunch it's
ridiculous very interesting Andrew
Wilkinson ladies and gentlemen where
should people go they want to keep up to
date with the things you doing well they
can follow me on on X or Twitter I don't
know what we're calling it these days uh
a Wilkinson or they can go check out my
book it's never enough.com um and yeah I
would love to hear what people think
hell yeah appreciate you man thank you
thanks dude thank you very much for
tuning in if you enjoyed that episode
you will love my ful length three-hour
long conversation with Alex
hosi right here go on what else you got
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