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.
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.
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.
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.
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.
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.
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?
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
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Could be just the thing you need.
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