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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to the episode of
the Startup Therapy Podcast.
This is Ryan Rutan,
joined as always by my
friend, the founder,
and CEO of startups.com.
Will, Schroeder will.
It's no secret that as
founders, we work and we work
and we work, and we do all
these things with the hope
for some level of payoffs or
some freedoms or some joy out
of all this stuff that we do.
And yet, like when we get
there and we begin to celebrate
some of these wins, were you
celebrating with a whole bunch
of your friends who were all
just as happy as you were with
what you had just achieved?
I was
hoping
so.
Yeah, like I really thought,
I'm shocked at how as we become
more successful, if we become
more successful, and this
isn't just with startups, it's
with anything in life, right?
How, what we think will
be this, this like loop of
validation where we're like,
oh, look how well I did.
And it reflects on the
people around us that are
like high fiving us becomes
a loop of resentment.
Yeah.
It becomes a, a loop of
people saying, fuck you.
Yeah.
You're like, wait, what
just happened here?
Right?
Like imagine for a second
you've been training
forever for the Ironman.
You work your ass off
for it and you come in
and you win the Ironman.
Yeah.
And at the end of it, where
all your friends are standing,
they're all booing you.
That's essentially what happens.
And so I think it's worth.
Unpacking today.
Why it happens.
Why do our friends resent us?
Our friends, peers, you know,
everybody you know around.
To me, they're less important
because I kind of don't care.
Right?
Obviously, the closer they
are, the more it impacts me.
The more you feel it,
it is.
And theoretically, those
are the people that are
supposed to care about you.
Yep.
I think that's why
it hurts the most.
So, so yeah, it's so
antithetical, like how is
it that these people that I
thought really cared about
me kind of hate me now?
Yeah.
Like I, I thought doing
something good brings good
and all of a sudden doing
good, uh, brings bad.
I think it's important
for folks to understand
where it comes from.
What's the source of that?
How founders deal
with it, good and bad.
Right.
And I think it's also helpful to
be able to say how much should
we given or, or not to that.
Yeah.
Like, you know, should
we let all the haters, so
to speak, determine what
we're allowed to say?
Conversely, should we
say what we want and and
be surprised when people
are, go fuck yourself.
It's funny, it's funny how
often we have to like develop
a thick skin as founders.
It's almost like different
types of permeability, right?
What works for water at
permeability doesn't work
for bullets, doesn't work
for electricity, right?
Like it's, it's as if like,
you'd think once you just
became thick skinned and
you get to this point,
you'd be like, ah, I'm okay.
I'm good.
I'm, it's not gonna bother me.
And yet it's like each one
of these new scenarios, you
have to have a different
type of thick skin.
To not be bothered.
'cause I had clearly, like,
by the time this this kinda
thing happened to me, I had
already developed pretty
thick skin having been punched
in it, not literally, but
figuratively punched in the
face by clients, probably pretty
close to that in, in reality.
And, and just, you know,
surviving all of what
it took to, to build and
sell that first business.
And yet when those
things started coming
around, I was like.
Really, really, I'm
unprepared for this.
I, I, I've never seen
that punch before.
I'll give you an example of,
uh, of the first time this
happened to me where it was
like really, really obvious.
Okay, so, so here's the setup
figure, like throughout my
life, like I was the person
on the outside or there were
wealthy people and I was always
the person on the outside.
I grew up in Connecticut
and people like, oh,
I was a rich kid.
I was not, I was the polar
opposite of a rich kid, but
there were lots of other
rich kids, Uhhuh and I.
I was forced to grow up watching
from the outside what it was
like to not be a rich kid.
Sure, right.
Oddly, I don't know
that I resented it.
It just sucked not to have it.
When I say it, people might
be thinking, I'm talking
about like golf course
memberships and private jets.
I'm talking about things
like food and family,
like fundamentals.
So I'm going up without much
and you know, I build, this
internet company starts doing
well and I remember I go out.
I buy a Lamborghini.
Okay.
Like the, the most,
like quintessential like
poor kid makes money,
tries to be rich kid.
Like it's, somebody had,
had, had written this to
me a couple hours ago.
He's like, that's what poor
people do when they think that
that's what rich people do.
Yeah.
Right.
I was like, Nope.
That's exactly what I,
that's, that's pretty close.
I can't deflect
that at
all.
How was I
supposed to know?
Yeah.
So anyway, so I,
I, I buy this car.
This is long, you know, this
is decades before social media
when if you wanted to, to
post something, so to speak,
that actually meant calling
someone and having them come
to your house or you go there
and actually talking to them.
I mean, you could have made
it, you could have included
it in the, in the annual, uh,
Christmas newsletter photo.
Yeah.
The group facts.
Yeah.
So, so I called my buddy.
Uh, we've known each other
since middle school, so we've
known each other a long time.
He's a great guy.
And I said, I got
a surprise for you.
I wanna show this to you.
And uh, so he comes over and I
open up the garage and there's
a red Lamborghini, right?
And he's like.
Huh.
And I was like, weird response.
Now mind you, I'm
22, so is he right?
Yeah.
Like, like we're getting out
of college at this point.
Yeah.
So it's not like it
should have been like 15.
Can I drive it?
Right.
That should have been
the reaction, right?
That's what you're
thinking, right?
Yeah.
And I think just like if I
backtrack, I can't remember
exactly what my expectation
was, but at a high level it was
probably something like this.
Will, you are the coolest,
smartest, most attractive man
that has ever lived, and no one
deserves this more than you.
Not exactly those words.
Yeah.
I couldn't
have written it better myself.
Yeah.
But some version of like,
like this validation, right?
I'm, I'm sure that,
that I was seeking.
So here's what he says.
He goes, huh, well, must
be nice and I must be nice.
That would be the first time
I had ever heard, must be
nice weaponized toward me.
And it would not be the last.
Must be nice is maybe one
of the most original og
passive aggressive Oh yeah.
Dickhead comments of all time.
It's a, it's a passive
aggressive battle ax.
Right?
Oh my God.
It's amazing.
It hits hard.
Let me contrast that with,
with my situation, because
look, you bought a Lambo,
that's a strong statement.
It was also bright yellow.
It's a strong statement.
In my case, I've.
I don't feel like I
deserved it at all.
I had just simply gone back
to my hometown and bought
a billboard that says,
better than You since 1978.
Um, uh, uh, proven social
media in 2001, right?
No, I didn't do that.
So it was funny, the first
time this came up was in a
conversation with somebody.
And I was, I was going through
kind of what had happened
after the sale of the company.
What had happened with the,
because they were kind of
asking you, they were digging.
Yeah.
And I, I should have understood
that they weren't curious.
That they wanted, they were
looking for something to,
to, to pick the fight over.
Right.
And I started explaining
like, here's, here's what
happened with somebody.
You know, X went to this
person that I had a bunch
of college friends, got.
Checks at the end.
And they were using 'em to
do things like pay off their
student loans or one, uh,
started buying early real
estate over an Italian village.
That worked out well.
A lot of foresight there.
'cause they were not
nice at the time.
Like you ran a crack den for
15 years and then it turned out
to be something really nice.
All that.
And, and then I said, I
said something like, you
know, I didn't use mine for
that because, you know, I
had a partial scholarship
and something else.
And then I got the, i, I
don't remember if it was
exactly the must be nice.
So naive was I, it
didn't even occur to me.
I was like, which part?
Meaning like that I had the
scholarship or these like.
Know that you can basically,
I, it was something along the
lines of like, play God, or,
you know, or, or, or stand on
high and distribute checks.
And I was like, holy shit.
Did you hear what I just said?
Like, I just said that
like, people did these
cool great things.
I wasn't even talking about me.
Like we hadn't even
gotten into that part.
Yeah.
Yeah.
I did some dumb ass
shit with my money too.
Yeah.
But like, we didn't
even got into that.
This guy was mad that I'm like.
What, by the way, clearly
like a validation seeker
himself, and hopefully he
won't figure out who this is.
It's not you, Brian.
May I promise.
I'm just kidding.
It's, it's not in
not even a real name.
I looked up 14.
My name's Brian, I looked
up at at the calendar.
It's May, it's not,
it's not a real person.
There may be somebody I
know named that, so let's
be really carefully.
It's not actually the thing,
but this was one of those
individuals that, like I
remember around the time
of graduation, it was like
seeking that top job coming
outta business school, threw
it in everybody's face that he
had the interviews, wherever.
Got it.
And we all, like, we actually
had a party to celebrate him
getting this job, and this
is the same person that will
come back around and just
like absolutely undercut you.
Well, but it's odd.
It's odd when you first
experience it because
you don't understand
where it's coming from.
Yeah.
Later on you'll learn exactly
where it's coming from.
That's what we're
about to talk about.
What I didn't understand was,
I thought, again, at the time
being naive that if I was
successful, I would be like
rewarded in high five back
to the, you know, trading
for the, the Ironman and
crossing the finish line.
What I hadn't planned
for at all was that my
success is a reflection
of someone else's failure.
And that is what I didn't
start to understand.
And I think, you know, founders
that are listening, particularly
those that are listening right
now, we have a lot of actually
very successful founders
that listen to the podcast.
Thank you, by the way.
And they're like, yep.
That's pretty much what happens.
Yeah.
Like, like all of a sudden
you get vilified for something
you worked hard to achieve.
Yeah.
Man, it, it's, it's awful.
But it's exactly that.
It's like.
We polished the trophy
that we won, that we worked
hard for, and all they see
in that is a reflection
of how they fell short.
That's it.
It's such a sad fact.
It's also not what you expect.
Yep.
Okay, now, now if you've
had a different upbringing
and you've seen this happen
and you know again, you did
expect it, good for you.
I certainly did not.
And so for me, I was
like, my relationships are
all about to get better.
Like better, better.
They all got worse.
They all got worse.
Yeah.
And like when I talked to,
actually, this is a good one.
I talk to professional athletes.
I took the professional
athletes who've made lots of
money in, in whatever league
they came from, they all
have exactly the same story.
I'm always like, and then at
what part, at what point did
every family member come to
you and ask you for money?
And you eventually
had to say no.
And then they all
hated you for it.
The, the second they found
every single one of them
Yeah.
Was like, oh, that happened
in my second year, or that
happened when I got signed
or that happened, whatever.
And I say professional
athletes because their
salaries are giant.
Yeah.
They happen at a young age
and they're very public.
So everyone knows
they have money
and everybody else, there's,
and there's always a lot
of people, maybe not the
family, but there's always
a lot of people who think
that could have been me.
It was just slightly
different circumstance.
Right?
So there's all this, it's
this built in ability to
resent them for it, right?
You bet.
And so we get into this
place where in our minds,
again, we think our
success will validate us.
Part of that validation, whether
we like it or not, comes from
the people around us, especially
the people that we care about.
It's every kid trying
to impress their dad no
matter how old they get.
I've got friends that
are, they're in their
fifties right now.
They're still trying to make
a statement to their dad.
I told you we were just in
Florida a couple weeks ago
and we found a bunch of old
game footage, and I found, I
found one, it wasn't even me
scoring a goal, but I found
one of me making a beautiful
cross to a header goal.
It was just, it was
a beautiful play.
So I just took my phone out,
recorded that 15 second video
clip and sent it to my dad.
I. And I knew exactly
what he would say.
Great job, bud.
And I was so excited
to hear that, right?
Yep.
I'm 46 years old and that game
happened 30 plus years ago.
Still felt nice.
And a, a founder that, uh,
reached, reached out to me in
a comment on, on a thread like
this, uh, a little while ago
and was like, I have a friend
who was a national champion.
In, in a very high-end sport,
came in second and their,
their father's response was,
congratulations on coming in.
Not first.
Ouch.
That's their kid, dude.
Second place is the
first loser, right?
Yeah.
That's, that's your,
that's your right.
That's exactly what they said.
I'm like, what?
What?
Yeah.
So again, what throws me.
For a lot of us as
founders, we do have an
insecurity and a validation
loop like everyone else.
It's not unique to founders,
just ours just manifests
often in our work, right?
It's a big part of where
we get our validation.
We try something really
risky and we know it's hard,
so when it works, we are
validated from our risk and
the effort we put into it.
But also when it works,
somebody else looks at it
from the outside and they
say, huh, must be nice.
Must be nice.
It's just a different way of
saying, you don't deserve this.
Exactly right.
It's a bit of a dick punch
and it's so hard not
to take it personally,
and I do get it right.
The point that you're
making it's personal
is a very valid one.
It feels very personal.
I understand that they might
not even be trying to do that.
It's not that they're offended
by our win necessarily.
They're offended by the
lack of their own win.
Right?
Yeah.
We are now a, a mirror
where they can, they
can look at that and go,
here's where I fell short.
Here's, this is giving me
a chance to compare myself.
Yep.
Which is an entirely
unfair comparison.
We've talked about this, like
they're comparing the outcome.
They're not comparing, well,
what were you doing for the
last nine years while I was
building and killing myself to
do this while you were playing
golf and collecting a salary and
whatever, whatever, whatever.
I didn't begrudge you
those things at that time.
You don't get to
begrudge me this.
Now, of course, that's
the logical argument.
It just doesn't work that way.
They're gonna pick that, that
one little moment, this the
the end game and say, yeah, I
wanna compare myself to that.
I'm feel bad about it, which
such a bizarre behavior to me.
Let's talk about how people
actually process our success.
Sure.
So we understand kind of
what this rubric looks like.
Yeah.
And the why now, again, I think
most people listening have
a pretty good sense for it,
but let's just say it anyway.
So it's defined, and I would
say let's use social media
as the perfect, perfect
social experiment for how
people process themselves
through the lens of others.
Sure.
And I say social media
because your feed is a nonstop
validation loop for everyone
else and for you and for you.
And depending on who you are
and how you feel about your
life, et cetera, that feed
is like a Rorschach test
of your own insecurities.
Yep.
If you're insecure in your
marriage, you're gonna
see all the people that
are happy and hate them.
Yep.
If you're insecure in your
job, you're gonna see all
the people that are that,
that are doing well and
hate them like you name it.
You're insecurities will
reflect from that feed.
Now, when I think about that,
I always think about when the
people are posting what they
thought, the people responding
were actually thinking.
For example, person posts that
I'm on the best vacation ever.
Coolest vacation ever.
There's a handful of people
that also think that, or maybe
that could go on that vacation
or are on that vacation that
are like, oh wow, you know,
I was actually there too.
Okay.
And even when they say that,
it's a validation of saying,
I'm as good as you are.
But most of the people either
aren't on vacation, myself
included, or they're, they
can't afford that vacation or,
or your vacation represents
something they cannot
do and they resent you.
Is that your fault?
Should you have not posted
about, I mean, we, we,
we'll talk about like how
to react to all this, but
Ryan, when you think of
other people or even yourself
reacting to other people's
success in whatever form.
Via your own insecurities,
how do you process this stuff?
You know, it's interesting, you
and I have talked about this.
You're very self-aware.
I'm curious how,
how you look at it.
Yeah.
You know, I, it's funny, I,
I guess I've, part of that
self-awareness was understanding
that I do process this a
little bit differently.
We've talked about this,
like, I don't have that
immediate reaction.
I don't resent people
for what they have.
I don't know, because I guess
I, part of it's probably,
I'm, I'm on social media a lot
less than most people I know.
And so, like, I haven't flexed
that muscle enough to know.
Um, and maybe I just don't
see enough to feel resentment.
For me, I've never, and maybe
it's an ego thing, but I've
never really thought about
what anybody else did as
having any bearing on what
I'm doing, unless it's direct.
Like if you and I go play
racquetball and you beat
me a racketball, I probably
won't resent you for it,
but I'll recognize that
you beat me at racquetball.
I think what's really bizarre
to me, this is the part that
I really have a hard time
even intellectualizing, right?
Because I can
intellectualize the rest.
I get it.
I get where it comes from.
I get the insecurity
piece, I get all that.
Here's the the thing,
I have a really hard
time intellectualizing.
It starts to treat.
These accomplishments that
are completely unrelated.
Your life.
My life, your outcome,
my outcome as some sort
of a zero sum game.
You got it.
Therefore, I can't.
Yep.
That's the part that I
just, there's no logical
argument around that, that
makes any sense to me.
Right.
And so this is the part
that I, I, I think I
really struggle with.
I think, you know, for better,
for worse, and again, maybe
it's an ego thing where I just,
I, I maybe I just don't value
other people's opinions as much
as some people do in that way.
Even when I get that kind
of negative feedback, like
for example, when that that
whole scenario happened that
I was describing earlier
about somebody just being
like, wow, you, you asshole.
You help people pay
for their college.
I'm like.
It didn't bother me.
It didn't make me think I
should change something.
I did something wrong.
Yeah.
It just made me think
what a bizarre reaction.
Right?
Yeah.
And so I think for me at
least, I haven't had to
develop a particularly
thick skin around this.
Maybe I just haven't
been successful enough.
I don't know to where it's,
it's mattered that much to
me, to the point where like, I
haven't ever felt hurt by it.
I never saw somebody resenting
me for something where it
wasn't so thinly veiled
in their owns insecurities
that I was okay with it.
I'll give you a, a totally
different example where I
see this, my wife Sarah, with
all her girlfriends and she
has lots of girlfriends in,
in from different cities.
We've lived in different
stages in our lives, et
cetera, and most of them,
for whatever reason,
don't like their spouses.
Hmm.
Okay.
And she's like one of the
most common threads whenever
we get together and girls get
together, everybody bitches
about their, their spouses.
Sure.
Okay.
She's like, except me.
And she's like, I
just like, it's.
Like, I'm not unhappy.
Like I'm just, I I don't
have anything bad to
say about you, Ryan.
You've known me for
a very long time.
I don't think you've ever
heard me say a negative
word about my wife.
I just don't have
anything to say.
Like she, I remember.
The only thing I can recall
will, uh, you, you did say once,
uh, Sarah, uh, just took a covid
test and it came back negative.
That's the only time
I can think of Sarah.
A negative in, in,
in the same sentence.
Like, that's it, that
it's very specific.
And that was, that's four
years ago and it happened once.
But so, so Sarah's
friends are pissed at her.
Yep.
Isn't that crazy?
Like, we're mad at you for
not being as mad at as we are.
Like theyve said
as much, they have
said as much, dude,
you're not talking.
In other cases where people
have come to me and said
like, you know, your situation
with your wife is bullshit.
I'm like, huh?
They're like, there's no
way you're that happy.
I'm like, sorry.
This will show you
like how deep some
of this stuff goes.
I, I remember this
once where like.
Because my wife, not guys has,
has the same kind of things
like that and there's WhatsApp
groups, there's like, they
talk, they do whatever together.
There was something where
she was basically describing
like, no, we don't, we
don't have that challenge.
Right.
Like or Right.
Maybe it was something
that like I. I did, or
that we do together.
I don't remember what it was.
It doesn't really matter.
But the comment that came back
was, what did that cost you?
Oh my God.
Meaning that like, there's gotta
be another side to this coin.
There has to be another
shoe that's gonna fall.
Right.
You can't possibly have
something good without something
bad having come as a result.
Like you must pay
for it elsewhere.
I'm just like, wow.
Right.
Like right.
Can I've, I, I guess here's
the other part that I don't
get, I legitimately do, for
some people, people I care
about, like if Elon Musk
gets another private jet,
I'm not like, good for him.
I don't resent it, but it
doesn't, doesn't change the
price of tea in my China.
I just don't give a shit, right?
If something happens to somebody
that I care about legitimately
care about and have some
attachment to their life in a
way where I know what they've
been through, I know what
they're doing and I know what
they, what it costs 'em to get
that thing, I legitimately take
joy and can feel gratitude.
For what they've gotten, and
that makes me feel great.
It makes me feel better.
Why wouldn't you choose that
over, over this, the exact
polar opposite, which is what
we're saying most people do.
I, I just still, again, I
go back to the fundamental
flaw in the logic.
Around why this is happening
in the first place.
Well,
but, but again, piss me off.
I'm using these examples of
places where like, you know,
you, you and I are fairly secure
in those aspects of our lives.
Yep.
To point out that like
even still, we all
process our insecurities
again as a reflection.
Right.
And, and again, this all maps
back to how founders need
to understand this, right?
Yep.
The, the idea that I'll be
successful and it'll have
no impact on everybody else.
Everybody will just
be happy for it.
And I'll get tired of high
fiving everybody all the
time is such a giant miss.
The flip side where they're
like, oh, it must be just
my friends that are kind
of douche bags about this
whole thing, or, or my dad
or my cousin, or whatever.
No, it's the whole world, dude.
And it gets exponentially worse
as things get better for you.
Yep.
It gets, uh, more isolating.
It tends to be why wealthy
people begin to isolate.
Yeah.
Part of that's because
there's a lot of people
trying to take from them.
I'm just straight up.
Yeah.
But the other part of it
is you don't wanna be in a
situation where the people
around you, you constantly
have to, to walk in eggshells.
I. Okay, I'll give
you an example.
Years back, this is
around, you know, the time
where I bought that car.
I'm at a family event and I'm
talking to one of my cousins.
Good enough guys.
So no issues there.
Yep.
But I'm talking to one of
my cousins, this is again,
early before I, I started to
really understand like what
you're allowed to say and not
say and all this good stuff.
And he was talking about how
his car broke down and that
it was gonna cost as much
as like $500 to fix the, uh,
whatever was wrong with it.
And how basically like that
was more money than he had.
I immediately shot back.
I'm like, dude, I know exactly
what you're talking about.
I was pulling into a restaurant
the other day and I bottomed
out the front end of my
Lamborghini, tore the, uh,
tore the, the fender off the
front, uh, the fairing rather.
And, uh, it cost me $10,000.
And he looked at
me like, fuck you.
Yeah.
Right.
And now, now to be fair,
at the time this is, this
is to, I say this to say,
I would never say that now,
would it ever occur to me?
Look, you were
emotional maturity.
With age and learn lesson.
Right.
I thought he was gonna be
like, man, doesn't that suck?
Like, you know, I
was gonna say, yeah.
Like I'm dealing with a
problem just like that.
Like something broken.
It's expensive.
I hate it.
Same, same but different, right?
No.
Yeah.
And
so you could then you could
take that version of me, go
to a different social circle.
Have the other person say,
Hey, I just bottomed out
my Rolls-Royce, it cost me
$10,000 to replace whatever.
And I'm like, oh yeah, I just,
you know, bought up and like,
and then you're on the same,
uh, path at the same time.
My cousin, he doesn't
wanna be around me.
Right.
For that reason.
Yeah.
He wants to be around
someone else where it's like.
Dude, I could never
afford 500 or a $500
Problem is a big problem.
And it's the, it is the problem.
It's validation loop either
way.
I get it.
Look, I get it.
I, I'm not faulting anybody
for it, but I think it's
important, like I said,
that, that we understand how
people process success, which
then leads to the question,
should we deflect this?
Attract this.
And what I mean about that,
how much should we care about
what other people think?
Here's what I mean.
I'm not saying should,
do we have a right to
just be jerks about it?
That not saying that at all.
What I'm saying
is at what point.
Is it our liability for
how people react to things?
And on the other hand,
do we keep it a secret?
Do we just never talk about
it because we're so fearful
that unless we absolutely
mute ourselves, that we'll
create these feelings?
Like, you know, do we, we
prevent other people from
feelings by virtue of us
not talking, you know?
Uh, what are your
thoughts there?
Are we going?
Yeah.
Well I think it's, it's an
interesting way of looking at
it and I, I think there are.
Aspects of it where I would
probably go, let's, let's, so
the, the spectrum here is like,
you're going scorched earth
versus secret squirrel, right?
Right.
I'm either gonna shout this
from the rooftops, or I'm gonna
hide it in the basement, right?
Like I'm, I'm digging a
hole and nobody's ever
gonna know about it.
What's interesting is
that I think if you go to
either ends of those holes.
You are going to
invite some challenges.
You know something that's
really funny about everything
we talk about here is
that none of it is new.
Everything you're dealing
with right now has been done a
thousand times before you, which
means the answer already exists.
You may just not know
it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems all
dayLong@groups.startups.com.
So if.
Any of this sounds familiar.
Stop guessing about what to do.
Let us just give you the answers
to the test and be done with it.
Let's talk about two
different versions.
Okay.
Let's first talk about
the, I don't give a shit
what anybody thinks.
I'm going full guns
like full Elon Musk.
Like just, I don't care.
Wanna see my new tattoo
on my 12 pack abs?
It's, it's my new
tattoo of my new Lambo.
Right?
Yeah.
It's my thing, just
like zero shit's given.
I'm going all at it.
Tattoo of abs on my abs.
Um,
it's, and so, okay.
So that, that is the
epitome of social media.
Yep.
They're the quote influencers.
My job is to remind you every
single day of what I have
and, and have you want me
more Now those tend to be.
This isn't me hating, I've
just, matter of fact, in my
experience, they tend to be the
most insecure people I've ever
met if I was that insecure.
Right.
And I, I'm insecure
in my own way.
So I'm not saying I'm not,
but if I was that insecure,
I'd be doing exactly that.
That is exactly, I would
be trying to fix that
problem and I get it.
But Brian, we see a lot of that.
We see a lot of
the, I don't care.
I'm going for it.
Let the chips fall
where they may.
What's your take on that?
You know what's funny?
When I think about the, the
amount of that that I see
on social, specifically on
social where I. Anything can
be fabricated, anything can
be made it look like anything.
Most of the stuff that I see
on social, my perception, I
could be completely wrong.
My perception is that it's
not actually stuff that I
have, I'm trying to use this
to attract that stuff, right?
So if I'm showing myself on
a private jet, I probably
don't have a private jet.
I want a private jet, and
I'm trying to show that I
have a project jet to show
off the image so that I
can go get the clients and
make the money or whatever.
It feels more like that to me.
Again, it it's social
media being what it is.
Maybe that's just the echo
chamber that I find myself
caught in, and maybe that's why
I've avoided as much as I do.
And again, like I think you
said, it, it, it's gonna
depend on the insecurities
of that person, right?
It's gonna reflect back,
like the things that you
see them shouting from the
rooftops are probably the
things that, that they still
feel least comfortable about.
Right.
The things that, that right.
I don't have as much money
as I want, or I'm comparing
myself to somebody else, so
lemme do everything I can
to magnify what I do have.
We get back to the,
the, the underlying
causes of these things.
Some of it goes
deeper than that.
Right.
I definitely remember a
big part of it for me was
justifying the fact, and
we've talked about this a lot.
Well, we've done a full
episode in this and it's
come up in a lot of other
episodes, justifying
what I gave up to get it.
To myself, right?
But also wanting to
memorialize it and have
people react to it basically.
So validate that what
I got was good, right?
Like my Lambo, like my
private jet, like my whatever.
Because deep down I go back and
say, was it worth it because
of the college experiences
that we gave up, because the
girlfriends, we didn't have
because of all that stuff
that we did and all those
things that we didn't do.
Right?
So I think a big part of
it goes back to sort of.
What's the hole you're filling?
What's the void that
you're trying to scrape
some filler into?
When I look at the far end
of that spectrum, which is,
screw it, I'm gonna just go
full guns about everything.
Yep.
And just kind of
vomit my success.
You have to know what
that's costing you.
There's no way there's a,
uh, a friend of mines, both
of us have, and a lot of
folks here might know on
social media, uh, Dan Martel.
Right.
I love Dan.
So, so this isn't me
not knocking him, but
I wanna point out.
His positioning.
Okay.
In, in, in a post a while back,
Dan even like talked about
this, so he, this is not just
my words, they're also, his, Dan
is unashamed about everything.
If you get on Dan's social
media, you will know that Dan
has a six pack or an eight
pack, or a 20 pack, or, or
it's a's a lot pack, how
many packs he's got left.
He's got a really nice
car and he lives big.
Yep.
Dan wants you to know that Yep.
That that's part of his, his
brand and his image, et cetera.
I. I love giving
Dan shit about it.
I texted him like I texted
him at the end of the year,
I think, and I said, um, I
just need to know how much
money your abs made last year.
Yeah.
He's like, cool about it.
Right?
Whatever doesn't matter.
Point is Dan's like, look for
years and years and years,
I was always afraid to talk
about stuff like this, but be
open about like my success or
what I'm proud of, et cetera.
He's like, and then I realized
it made me really unhappy.
Now I'm just not
gonna do it anymore.
Yeah.
If you don't like it, that's
on you, but I'm not gonna
mute myself for your benefit.
Yeah.
Yeah.
I thought that was interesting.
That was honest and
a bit vulnerable.
And so Dan gets to live with
an honesty, and again, we're
talking at the other end of
the spectrum with him himself
at the cost of everyone else.
Yeah.
So dig, dig into that.
What exactly do you mean
by at the cost of everyone
else to, to what cost?
In the cost of, does it,
does it cost Dan something?
I, I heard you say cost everyone
else, but meaning that like
he's gonna have to take hate
and vitriol or whatever.
Or that it actually costs
these other folks something
by, by contrasting themselves.
Dan understands very well
how other people feel because
he felt that way himself.
Yeah.
Like when Dan posts I'm
rich, I have, you know, nice
car or something like that.
Yeah.
He knows damn well that
other people feel like,
shit, I wish I had that in.
Fuck you, Dan.
But Dan's like, I
just don't care.
I, I'm, I'm not gonna mute
myself for your benefit.
So by virtue of that, he's
like, yes, I do know that
it's going to hurt you and
that's your problem, not mine.
I'm not advocating that
approach, but I will say
that there is some merit
in the honesty of it.
Right?
In other words, he's, he's
like, why is it my job
to make you feel good?
I. Why is it my job to make
up for your, uh, inadequacies
or your insecurities or,
or whatever you have?
And he is not wrong.
It is not his job, per se,
not the way I would play it.
Right, personally.
'cause I actually, I don't
have a gear like that
where I'm just like, I, I
don't care how you feel.
This is how I feel.
And, and if it hurts
you, that's your problem.
I'm
an empath again, I, I don't
understand what it buys you.
I, I just don't get
what it buys you.
I get maybe, maybe,
and maybe what it buys
him is maybe filtering.
Really hurts him.
Right?
That's, and that's
a personal thing.
But then even there, like, I'm
gonna go back to like, okay,
well, but that's my pain and
that's for me to deal with.
And if I'm causing lots of
other people pain, but then
I would also go back to, but
like, but why, why is that
actually painful for them?
Why can't they just
appreciate my abs and
move on with their life?
Right?
Like, Hey Will, by the way, do
you know what has six hands, six
legs, six abs and spaghetti on
its spaghetti sauce on its chin?
What's that?
You, me and Dan at lunch.
That's the dumbest riddle.
I love it.
So, okay, so let's go to the
other end of the spectrum.
I wanna avoid resentment,
so I'm never gonna put
myself in a position where
anybody can see it happen.
Okay, I'm gonna
never talk about it.
I'm gonna go extreme
humility, et cetera.
Now, generally speaking, I would
say that works great because
you will avoid resentment.
Obviously people have no
idea you've had any success.
Then there's nothing to resent.
We had a guy that worked for
us years and years and years
ago, and he was a developer.
Really nice guy.
And months, and months
and months went by.
And this, uh, Ryan, this is
back when we used to give,
um, like paper paychecks.
Oh yeah.
And, um, and I noticed that
all of his paychecks, like,
like, you know, in the,
in the envelopes were just
stacking up on his desk.
Unopened and I was like, maybe
there's something that he's
doing with those, whatever.
Like just, I've never seen
anything like it, much less,
not caring that un cashed checks
were sitting on your desk.
So at some point I had,
I, I pulled him aside.
I was like, Hey,
is everything okay?
Like, whatever.
He's like, yeah, uh,
it's embarrassing.
I'm like, okay, this
is gonna be awesome.
He's like, years ago my dad sold
a company for like quite a bit
of money and uh, you know, put
a lot of it in my account and I
actually just don't need money.
It's what I like.
Not, not, I actually
just don't need money.
Yeah,
not, and here's the point.
Can,
can I just take you
off payroll then?
But leave your, leave
your office pass valid.
As I slowly grab and slide
those checks back, I'm
like, oh, good to know.
Remind me what your
signature looks like.
Good.
Do you have more
friends like this?
Perhaps?
I would like to employ
them as well, but.
And I'd known him for
years as a friend.
Right.
I, I'd known of this situation,
but it wasn't until he ended
up working with me and I was
paying him till I saw like,
you know, it, it up in lights.
Yeah.
And here's what I'm saying,
he was the guy that did
not want to talk about it.
Yeah.
Now, now part of that is
'cause he didn't earn it.
Okay.
Right.
So like, it's a little awkward
to say like, I'm rich, but you
know, my dad wrote me the check.
Right.
And I hate to be a sexist,
but especially as a dude.
I see this less with women than
I see with men, but I see it
painfully with men and, and
it's kind of an old school.
I didn't kill this and drag
it into the cave myself.
Right?
Yeah, yeah,
yeah, yeah.
Anyway, point is, that's on
the other end of the spectrum
where this guy has millions and
millions and millions of dollars
and doesn't wanna talk about it.
Yeah.
Yeah.
By way of that, he also
doesn't drive the resentment
that comes with it.
He's going to to lunch
with all the coworkers
and they have no idea.
He has millions of dollars.
Yeah.
So
it never comes up.
He Right.
No.
No one ever gives him a hard
time about it, whatever.
Now, again, a little
bit different.
'cause in this case
he didn't earn it.
So it's, it may make him
feel shitty to talk about it.
Right.
'cause then he has to
explain where it came
from and didn't earn it.
You know, like it actually
kind as a negative connotation.
But let's, let's take that back.
If we had earned something.
But we also become so concerned,
so fearful of sharing it,
that we hold ourselves back,
that we mute ourselves.
Is that okay?
Depends, I guess.
I mean, at that point you're,
you're kind of living in a
prison built out of other
people's insecurities, right?
That's kind of the
opposite of the damage.
But are you
Right?
I guess it goes back to like,
are you holding yourself back
from some necessary growth
or validation or something
that you deeply need?
Yeah.
Again, like then maybe
just go to therapy
instead and find out why.
But I. I mean, it, it doesn't,
it doesn't feel right.
It doesn't feel right
to have to do that.
And so, you know, one of the
things that I think I have
tried to do, and I don't
know how successful I've
been at it, but the things
that I like to talk about
in terms of accomplishments.
Are things that I feel
like are attainable, right?
That they're not the, it's not
like the big financial outcome
or the, you know, at some points
in my life where, like post-sale
of a company, I had all the
time freedom in the world.
I didn't talk about the
fact that I, like, I
don't have to do anything
for the next six months.
I do whatever I want.
What I would talk about
instead, were things like,
I've decided to spend
three more hours a week.
On learning language I've
decided to spend Right.
You know, uh, every, every
weekend doing some of the
like, give something that
like actually can be copied.
Right.
Right.
And maybe part of that is like
just me also looking, not for
validation, but camaraderie.
Right.
Like, okay, this is
something we could all do.
Right.
I appreciate that.
I like that.
Right.
I was a team sports guy, right.
So like I'm, I'm probably
constantly seeking my next
team and, and people that wanna
participate in what I'm doing.
But I think I've also
been fairly careful about.
Choosing, you know,
participation.
If, if you like show up at
your high school reunion,
you're like, it's a race,
Lambos, who else has a Lambo?
Right?
Like, they can't
participate in that.
Right?
Right.
Yeah.
You know, you're doing
that, but like you get it.
So I think that's been part of
it for me is that I don't have
to be completely couched in
talking about what I have, what
I've achieved, the things that
I do enjoy in life, the things
that I'm proudest of, some of
which have absolutely nothing
to do with financial success.
Right.
It's like I'm proud of
the way my, my family
interacts with each other.
I'm proud of the fact that
like we, we have time together.
We do these things.
Things that literally
anyone can achieve.
Yeah, but it's interesting,
Ryan, because like I tell
Sarah this from time to time
when you and I share on the
weekends, like what we're
working on, what we're doing
over the weekend, and I'm
invariably saying, I'm building
something to do with the house.
And you talk about all these
cool adventures that, that
you're going on with, with,
with your, your family.
And I always say to Sarah,
you know, when I share
that with her, I'm like.
Ryan is like the
Jeff Bezos of dads.
He's like, he's like ultra dad.
And, and I, and let
me build on that.
And I say, I'll never be
that level of dad, like have
that level of engagement
and, and, and planning
and, and all this stuff.
And, and I'm, but I
don't resent you for it.
I'm, I'm actually, my feeling
is if that's what I, if
that's what I wanted or
if, if I was that person,
that's what I'd be doing.
Yep.
But I'm not, and I'm okay
with that, but I think
I'm okay with it because.
I have enough other things in
my life that, that I feel like
I'm secure with, so to speak.
Sure.
Well it's also, again, go back
to like the fact that you've got
some baseline, again, baseline
securities there, which is
like, you may not do all the
things I do with, with my kids.
I don't do all the things
you do with your kids.
Right.
Like yeah, but it's, it's not
like you're a, an absent father.
He doesn't like, what,
what are your kids' names
and what are their ages?
Lemme ask my wife.
Right.
It, it's not like that.
And so I think that's, that's
part of it where I think that's
where it gets really tricky.
Because in a lot of cases,
I think I am picking
things where the contrast
won't be so harsh, right?
Or said differently.
If it is that harsh, well,
maybe, hopefully it'll
motivate somebody, right?
If you're that bad of a father
that like that, you look
at me and go, you asshole.
Yeah, yeah.
Sorry.
But like good on me for like
shaking you a little bit.
Okay.
For sure.
For sure.
Agree.
I agree.
That feels okay because
again, it's not unachievable.
I'm choosing to spend time.
You know what's
funny about time?
You get exactly the same
amount of it as I do, right?
We all, every time I
spend a minute, I get
another one for free.
I. So just you get to choose
how you spend your time.
Let's talk a little bit
about kinda like how we can
process this successfully.
Yeah.
Right.
He, he, here's what I have seen.
If, if I've seen any pattern
among countless founders that
you know, that we know that,
that have done well, that
have seemed to have managed
the resentment, I, I'd say
fundamentally there's two
things that they've done well.
Number one, it's a
self-awareness that this exists.
Yep.
Again, me Lambo at
22 0 self-awareness.
In this case, it wasn't
just me being a douche.
I was being a douche,
but I didn't realize
I was being a douche.
Right.
It would take me, yeah.
Way too long to
figure that out later.
But
douche and deliberate, douche
are two different, very
different flavors, right?
Like Correct.
Yeah.
Like and, and, and now like
if I post something on social
media, I do have a version
of me, I. That says, who
will this affect and how?
Yep.
And, and, and will it
do it to some, like,
will it hurt someone?
Yeah.
Is probably the
best way to say it.
Part of me is mad about that.
Part of me is mad that, that,
like I going back to the Dan
Martel thing, that I have
to think like that, right?
That, that I'm doing it
because someone else isn't
happy with their life.
So I have to modify.
It's the walking
on eggshells thing.
I shouldn't have to change
how I think or feel or act
unless it's outright, amoral,
unethical, harmful by intent.
I shouldn't have to defend
you from your insecurities.
That's your job, pal.
Okay.
So,
so
let me build on the
other side of it.
The second part, the most
important part is humility.
Being able to say something
in an accomplishment or
something, but do it with
enough humility that you
don't sound like a douche bag.
And I'll give you a great
example, a great example of
someone who did this recently,
and, and everybody can, can see
it, not this past year, but the
year before, uh, Caleb Williams
of USC won Heisman Uhhuh.
Okay.
Now Caleb is not the,
uh, Steve Jobs presenter.
He's reading from cards.
But here's what was so
good about his Heisman
acceptance speech.
Okay?
Now, number one, you're in
a room full of of athletes,
but you're specifically
now standing across four
other people, or three
other people that didn't get
it, didn't get the award.
Yep.
And you have to address it
directly to high contrast
situation.
Correct.
Right.
Which is beautiful.
Caleb goes around the room
and, and he cites all the
people in the room, right?
Uh, all the, the other,
uh, former pro athletes
that were on the Deus.
He was like, listen, and he
pointed to specific people.
He said, you guys are the
reason that I'm here, right?
He said, um, as a kid,
I wanted to be you.
I would do anything
in order to be able to
stand up here one day.
Be talking to you.
Yeah.
Right.
Cool moment.
And he looked at the, the other
three, uh, quarterbacks, right?
Uh, uh, uh, Heisman Hopefuls.
And he said, guys, like,
you know, any one of you
could have just assumed
win this or won this, and
have been as deserving.
Okay, great humility.
Now, I would like to
believe he believes that.
Here's what he then did.
He said, let me tell you
the story of how I got here.
He told the story in a
way such as to say, no one
believed I could do this.
I didn't believe I could do
this right, and I was fortunate
enough to have a couple things
land my way for this to happen.
All of a sudden, here's a guy
who could have been breeding
all kinds of resentment.
You could have thought of a
very different speech, right?
I'm sure other Heisman
candidates or winners have
given the wrong speech,
but what he did, he used
gratitude and humility.
It's hard to hate a person
that's humble and grateful.
Now, I don't mean in a false
way,
like the humble brag.
Mean in genuine way.
Right.
Let me say something really
douchy and then throw a little
self-deprecation on it and
that'll make it all better.
It doesn't,
yeah.
Yeah, yeah.
And so where I think it comes
from, and again, there's one
thing to do it in a rehearsed
speech, but there's another way
to do it in your daily life.
I'm not pretending
I'm great at it, but I
understand the formula.
And when I watch other founders
who don't, who have success,
but don't seem to drive
that same level of humility,
here's what's important.
They are talking about it.
They are public about what
they've done, but they
do it in a way where you
can't hate 'em for it.
Yep.
It's an art and some
people do it really well.
Yeah, it's interesting.
It is an art, and I think that,
again, kind of for me, it's
gonna go back to like, what
are we actually talking about?
Right?
I think there are certain
things that are gonna
be more highly charged.
You're talking about money
or possessions, always
gonna be like that, right?
And so I think that part
of it is also, even just in
your own self-awareness we
talking about before, is like.
Getting past that stage and
really thinking about what
actually matters, right?
Like I've started to realize
for me the things that matter,
you know, having achieved some
of the material wealth, right?
Never had a Lambo, did
have a Ferrari matchbox
once, uh, pretty sweet,
um, but never had Lambo.
But what's really becoming
apparent to me is like,
you are the three things
that matter the most to me.
Having some freedom over
how I spend my time,
get to spend it with.
Startup founders doing
startup founder things.
Amazing.
Yep.
Who do I get to
spend my time with?
Again?
The startup founders control
over my nervous system.
Right?
Being able to regulate
my nervous system.
Those are the three things
that actually make for
a great or a not great
day for me at this point.
Right.
You could take some money away,
you could add some more in.
It isn't going to change
the temperature that much
for me at this point.
So do you think we can
avoid resentment altogether?
Well, yes.
Yes I do.
Do I think we can stop
people from being resentful?
No.
I think we can avoid having it
impact us by doing the things
that you just said, right?
Be humble about it.
Be grateful for what you
have, because if you're
just talking about it,
you don't appreciate it.
What are you actually doing?
What are you actually doing?
You're seeking
validation at that point.
So I think if you can say,
if you can say to yourself,
look yourself in the mirror
and say, I'm not seeking
validation with this.
I'm grateful for what I
have, and I'll be humble
about how I talk about it.
Then anytime you do face
resentment, you can go
undeserved, unimportant.
And I'm sorry they
feel that way.
And look, you, you're gonna
be in a place, Ryan, where
there's no version where you're
gonna do well and have it not
affect somebody, uh, adversely.
And sadly, a lot of
those people are gonna
be people you care about.
Sadly, a lot of those
people are, you're gonna
lose that relationship.
They're gonna be family members,
they're gonna be best friends.
They're gonna be who,
who are these people?
They're like people you grew up
with and you're gonna be like,
what the hell just happened?
This.
This wasn't supposed
to go this way.
This was supposed to
be very different.
And what we don't account
for, and that's kind of, you
know, the genesis of all of
this, what we don't account
for is there is a power
that we wield with success.
I. That can be used in
good and bad ways, even
if we don't intend it to.
It can alienate and hurt a
lot of people in, again, a
way we don't intend it to.
If you go the far into
the spectrum and you wield
it as a weapon and you
try to hurt people, that
usually means you're wildly
insecure, but that's fine.
Most of us are wildly insecure.
On the other hand, if
you can treat it with
humility, with gratitude.
With respect, and by virtue
of that respect, those that
are around you, there's a
tiny chance that you can have
the best of both worlds, that
you can have this incredible
accomplishment and journey
and keep all the people in
your life around long enough
to enjoy it with you and
not at the expense of you.
Overthinking your startup
because you're going it alone.
You don't have to, and honestly,
you shouldn't because instead,
you can learn directly from
peers who've been in your shoes.
Connect with bootstrapped
founders and the advisors
helping them win in the
startups.com community.
Check out the startups.com
community@www.startups.com
to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.