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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, I don't think founders
ever lie to anybody as much
as they lie to themselves.
We tell the world-
That's a great opener.
... we're building to change
everything, but I feel like most
of us are really building to fix
something that's been following
us around since we were a kid.
Will, w- why is it so damn
hard for founders to admit
their real why, and what
happens when they finally do?
I think we all know it, and
I think a lot of people are
kind of f- frankly afraid to,
to admit it, and l- actually,
to admit it to themselves.
Yeah.
Okay?
So-
Themselves, exactly that.
You're right.
Here's what we tend to say, and
we s- I mean, we've had these
conversations a million times.
Here's what we tend to say.
We talk to a founder and
we say, "Hey, what are you
trying to build?" They're
like, "Well, I'm trying to
build this thing that'll
change the world." Mm-hmm.
And I'm like, "Cool." Yeah.
"That's wonderful,
but why?" Right?
"Oh, because I think, you know,
th- this problem should exi-
" No, no, no, no, that's, that's,
that's why the problem exists.
Uh-huh.
Why do you wanna build it?
You.
But, like- Yep ... what is
it about this that if the
company was one person big,
100 people big, or 1,000
people big would change you?
Like- Yes ... like, w- where
are you in this equation?
Right.
Right?
And nine times out of
10, they're like, "I
don't... Huh?" Right?
Yeah.
Like, "W- what do you mean?"
And I say, "Look, man. All
of us are building something
in life, whether it's our
business, our family, you know,
everything, in order to fulfill
something inside of us." Yeah.
"But most of us have no idea
what that thing actually
is, whether it's a demon,
a void, or, you know, some
combination thereof. So we
kind of blindly build-" Yeah
toward a thing in order to like,
like, fill that void, et cetera,
or, or satisfy that need without
ever defining what it is." Yeah.
And that's a huge problem.
It's a
huge problem.
Because you're usually
wildly miscalibrated.
Yeah, man.
The public why is
marketing, right?
The private why- Yeah.
Yeah ... is, is motive, right?
Yeah.
And if you don't know the
motive, it's kinda tough to
steer the machine, right?
The, uh- Yep ... change
the world, to me, that's
the wrapper, right?
It's not the product.
Yep.
Yep.
The product is some
version of, like, safety,
validation, freedom,
revenge- Yep ... belonging.
Yep, rev- yeah.
Right?
Some, some- Revenge
is a good one
healing of deep inner wound.
Insert inner wound here.
Yep.
You got your internal why.
I, I saw a great quote, still
call it Twitter, from, uh,
a while back from somebody,
and they said something to
the effect of, "A founder who
wants to change the world is
exciting, but a founder who
wants revenge is unstoppable."
Yes.
Right?
So accurate.
So
I'm like,
"
Hell yeah.
Hell yeah." Absolutely.
Right?
And what we're talking
about is the, the pure-
unfiltered emotion that
makes you do what you do.
Yes.
Right?
And again, without getting,
like, too Freudian about
it, that's kind of what
the... I gu- hell, dude, our
podcast is Startup Therapy.
Yeah, yeah.
I guess we will get
Freudian about it, right?
Yes.
Let's, I was gonna say-
Um- Let's go, let's
get Freudian about it.
Yes.
Let's get on the couch, right?
We all have specific reasons
why we act the way we act.
Nothing comes from nowhere.
I always tell my wife this,
'cause when she talks about,
like, how our kids are behaving,
I said, "Listen, our son or
our daughter does not act the
way they act out of nowhere."
Right.
"It comes from somewhere.
There's a root cause to
that behavior"- Yes ... "and
we have to figure it out."
It's a combination- And
by the way, it's,
it's usually us.
Yeah.
We are the root cause.
We're, we're the parents.
I'm sure of it.
I'm sure of it.
Like, where, where else does it
come from?
Yeah, yeah.
And, and that's fine, but, like,
but we have to know what it is.
But here's what
happens when you don't.
This is what kind of gets
re- really interesting to me.
When you don't know what
it is, you start making
all of these decisions,
again, miscalibrated, right?
Again, you're like, "Hey, I
wanna build a huge company."
A- actually, no, I'll, I'll,
I'll be personal about it.
Like, why do I wanna
build a company?
Why do I wanna be in
en- entrepreneurship?
Because I'm terrified of
not being safe, right?
Yeah.
Which is ironic- Yeah ... 'cause
I picked, like, the most
unsafe career path you could.
Yeah, yeah, yeah.
But the reason for it, again,
all this stuff comes from
somewhere, is 'cause as a
kid I didn't have any safety.
And by way of that, I
didn't have any control.
Right.
So I looked at entrepreneurship
as something I could control.
When I say control, doesn't
mean it's always gonna go
well, but it was up to me.
Yeah.
Right?
And that's- Yeah ... all
I cared about.
Doesn't go well, it's
at your hand, right?
It wasn't somebody else
making a decision of where
you're gonna live, what
you're gonna do, are you
gonna eat dinner or not, yeah.
Exactly, right?
And so I looked at it
as if I can control my
own destiny, um, I don't
care if it's good or bad.
I mean, ideally it's good,
but, like, I don't care if
it's good or bad, I care that
it's mine, that it's in- Yeah
... within my control, because
I grew up without control.
Yeah.
A- and that was so deep in me.
And even 50 plus years later,
I don't feel any differently.
Like, that same need
has not changed.
But if I map back every
single one of my actions in
life, like all the things I
did with building companies,
you know, blah, blah, blah.
Yeah.
It always maps back to that.
Sure.
Everything comes from somewhere.
Yeah.
We're, we're not just
building a startup, right?
We're, we're building a
remedy, an antidote to-
Perfect ... whatever happened
in the past, and we need to-
That's a good way to put it.
Yeah ... a- and look, and naming
it's super important, right?
Yeah.
Naming it's super
important because if you
don't name the real why,
it's still gonna drive.
Yep.
It's just gonna drive from the
trunk, whereas- Yep ... a lot
less visibility and perspective.
And look, investors aren't going
to fund your inner story, right?
That's not what
they're there for.
Yeah.
Right.
Uh, but your inner
story- It's yourself.
... does drive the decisions
that determine whether the
company survives, right?
As you said before, a
founder out for revenge,
unstoppable, right?
Right.
Because that's that inner
story that's gonna drive them
through all of the difficulty
of building that company.
Right.
Right.
And I, I think for a lot of
us, you know, we look at it
and we're like, "Oh," like,
"I'm not insecure," or, you
know, "Oh, I'm not trying to
make up for, like, you know,
being a dork in high school.
I really care about this
thing." I'm sure you do, but-
It's funny that you brought
up being a dork in high
school, 'cause- Yeah.
... I wasn't.
There's the Freudian slip.
That's the tell right there.
That's exactly what it is.
Yeah, yeah, yeah.
That thing that they tell
you, it's not for this reason
or for that reason, it's
exactly for those reasons.
Right, right, right, right.
So all that said, I look at
this, you know, when I, when
I think about how people are
making these decisions, but
more so saying, "Here's what
I'm trying to accomplish."
Yeah.
I think they're, without
being intentional, they're
disingenuous about it.
I think that they look at this
and they say, like I said, "I
wanna build a big company."
And it's like, if you could
accomplish the same thing with
two people and no one ever knew
about it- Yeah ... would you
still wanna build a big company?
Like, maybe, right?
And they're like, "Eh, maybe
you're not solving the problem
you think you're solving."
Yeah.
Right?
Yeah.
And that's dangerous.
It is.
I think it's, it's funny, but
the modality is almost this
foregone conclusion, which
is, of course I must build big
company because if it's big
enough, then it will cover up
whatever this hidden wound that
I haven't even fully begun to
understand in my, my own right.
Sure, maybe.
Yeah.
But to your point, like, what's
the less path of resistance
to that same outcome, right?
Do we have to take- Yeah ... the
most difficult way at this?
Does it have to be that
big or could it be a
medium or a small company?
Well- Well- ... you said
something important there
though, which is that they're
not being disingenuous.
They're just not being fully
honest with themselves, and
therefore it becomes difficult
to be honest externally and, and
to talk to people about this.
I've got a couple ideas of my
own here, but what, what are
the most common moments that you
see where the founder's why, I'm
gonna call it, leaks out, right?
Where we start to see it
escape, uh, the, uh, the,
the sarcophagus and, and, and
come to life and go, "Hey,
this is why you're actually
here." What are those moments?
Is it fundraising, some
sort of conflict, burnout?
Where, where did these things
actually start to seep through?
You know, you and I have
done episodes on this.
It's when people
sell the company.
Oh.
And you have that certain moment
where they're no longer needed.
All of us at some level
need to be needed.
Right?
So as the organization gets
bigger and more reliant on
us, on the one hand we're
like, "Oh my God, this is
such a crushing weight." But
there's another part of us
that appreciates being needed.
We appreciate when people
call on us and say, "Hey,
we need your input. We need
your d- direction. We need
your decision." That is an
incredibly validating feeling.
Yeah.
You know, for as much as-
Yeah ... founders tend to write
it off like, "Oh, I wish they
didn't need me and could operate
on their own." No, you wish
they'd, like, you don't have
to give them the information,
but you want to be needed.
You might not wanna go to the
party, but you wanna be invited.
Yeah.
Right?
And I remember, uh, early in my
career when I was, uh, we had
sold, uh, my, my agency, and I
was basically cycling out of it.
I remember going into a
meeting with all of our senior
staff, and everyone knew
that I, like, 'cause it, the,
the agency had been sold.
Like, I, I was-
Yeah ... gonna be gone.
Everybody knew I was gonna be
gone in, like, three months.
And I remember I walked
into a meeting and I sat
down, and our COO said to
me, "Uh, what are you doing
here?" And I'm like- Like,
uh-oh ... "Huh? Great." Ouch.
It's game day.
Like, who, yeah, but why
are you wearing a helmet?
Yeah, yeah.
She was being a matter of fact.
Yeah,
yeah.
Right?
Like, "Hey," like, "you,
you don't need to be here."
And I remember, like,
it hit me like a cannon.
Mm-hmm.
And I was like, "I'm
not needed?" Right?
Like, and, and to be
fair, that was probably
true two years prior.
Yeah.
I probably wasn't
needed then, too.
But that feeling that I wasn't
needed w- was, was painful.
Now-
Sure
...
I'm not saying we have to,
like, stitch this into every
part of our day and every
decision we have, but we kinda
need to know what's happening.
Yeah.
Because whenever you see an
extraordinary personality,
extraordinary personality would
be, like, Elon Musk today,
Steve Jobs back in the day- Yeah
literally every, uh, artist
ever, that comes from a
very specific place, right?
Sure is.
Steve Jobs didn't become
Steve Jobs 'cause he's
just a regular dude.
Right.
Nor did Elon Musk.
It comes from a brutal
history of, like, like, what's
going through your head that
you're trying to account for.
And it allows you in many
ways to do great things.
You know, the artist's greatest
pain becomes their greatest art-
Yeah, yeah ... in, in many ways.
So this isn't me saying, like,
pain is necessarily bad or,
or insecurity is, are bad.
It's let's know what they are.
Yeah, yeah.
Because they are gonna
shape everything.
Yes.
Yeah.
Know, know your
motivations.
And it's, it's dangerous
not to know that.
Yeah.
Yeah.
Yeah, yeah.
Um, w-
we- Yeah, well, I, I think you,
you said it once, w- which was
that these things essentially
become your true North Star.
Yeah.
Whether it's conscious or not,
these end up being that kind
of guiding light, m- maybe more
of a magnetic force, right?
Yep.
Maybe it's the true
magnetic north, uh, that
we're pulled towards.
Where does that come from?
I think, like, at its core,
you know, w- we all need some
level of validation, right?
So that's, that's one kind of
big bucket, if we will, right?
Sure.
And, and I'm gonna go back
to the you were the dork in
high school type thing, right?
There's no lack of founders
out there, right, and, and
whether they wanna admit it or
not, that can't point back to
high school and- Something in
high school happened where, you
know, they didn't get invited
to prom or they didn't, you
know, they, they got laughed
out of the locker room.
I don't know, right?
You know, whatever your,
your metaphor is, and they
wanna make up for that.
They wanna go back and
show those people, and I'm
using high school as just
like- Sure ... a metaphor.
Show those people
that they were wrong.
Your parents leaned on you too
hard and you wanna show them.
You had a sibling that
was always better than
you and you wanna show
them, like, you name it.
All of these things tend to,
to develop, you know, what
drives you and what motivates
you beyond wanting to do
great things in the world.
And even sometimes wanting to do
great things in the world come
from somewhere very specific
that you're trying to like,
you know, map, make up for.
But I look at it and
I'm like, "Okay, man.
If your goal, if what you're
trying to accomplish is
validation, is recognition,
is being seen in all these
things, there are a lot
of ways to get there.
Let's map the best possible
way to solve for that problem."
Yeah.
A- and know which one
specifically it is, right?
Because you've- Yeah, yeah,
yeah ... you've named off a
whole bunch of things there.
Safety and control, validation
and status, autonomy.
Yep.
You know, if you can't stand
being managed, proving people
or silencing your critics,
belonging, identity, you
know, we want to matter.
Knowing which one of those
things it is has a lot to
do with being able to make
sure that your strategy for
how you grow that company,
what you build, how you
grow it, and what money you
take, who you choose to- Yep
work with all becomes pretty
damn important, right?
I agree.
Uh, Ryan, when, when
you think about it, w-
what's your North Star?
My North Star.
Look, uh, if... You
mean the real one?
The, the one I'm not allowed-
Yeah, no ... to talk about?
The, the fake one.
Yeah.
Yeah, the, the, uh, the
fake one is I wanna make
a dent in the world.
I wanna make my dent
in the universe, Will.
I just, you gotta figure
out where the boundaries of
the universe are so I know
whether I'm denting it from
the inside or the outside.
Look, I, I think mine is
probably a combination
of, I think about the five
core ingredients there.
Autonomy, definitely a,
a big part of it, right?
It's, is a big one.
What, what
pushes that though?
I think that probably, like,
a fairly controlled childhood.
There was definitely that.
And so the, this, it's all,
it all goes back there, right?
There were two things.
Yeah.
One, I mean, I've talked about
this before, we were very much
an achievement household, right?
You know, there were lots of
stories about, you know, my,
my father's athletic escapades,
the fact that, you know, he came
from a single-parent household.
Father died when
he was quite young.
Managed to put himself
through university, put
himself through medical
school, uh, did all these
amazing things, and achieved,
and achieved, and achieved.
There was very much a sense
that that was, that was the
track that I need to be on.
And so, like, validation and
status are definitely part
of what drives it for me.
But because autonomy was also
a big part of it, right, not
wanting to follow someone
else's path, wanting to be
able to say, "I did it my
way," meant that the more
traditional career path, like
become doctor, right, become
lawyer, become- Yeah, yeah
wasn't gonna work, right?
Because there wasn't
enough autonomy in that.
There was too many other,
too many rule sets, too
many other people telling
me what I had to do.
So I think for me, my north
stars are some combination
of the, the, the massive
gravitational forces of
validation and autonomy.
What, what else?
You said there
were other buckets.
I'm curious.
For me in particular?
You know, I think a big part of
it was, um, the other... 'Cause
I'm, I'm b- I'm just, I'm trying
to remember how I labeled the,
the ones that you listed off.
It would be like the,
well, a bit of the
revenge narrative, right?
So that, that proving and
silencing the critics.
As a, as a kid- It's a big
part
of being a
founder.
It is.
It's a huge part- Yeah ... of
it, and I think it's, it's
one of those things that
kind of sets you up for it.
But I think in my case, it does.
It goes back to childhood.
There were a lot of people
that, that doubted me or that
wanted to look at me and go,
"Oh, well, you're only that
way because your, your father's
a doctor," or whatever.
And I was like, "Dude,
I am the hardest-working
kid." Like, I was called
the little rich kid, right?
Yeah, I was the
hardest-working kid I knew.
I was busting my
ass on the farm.
I was building stuff.
I w- I was constantly
doing something to prove
them, them wrong in ways
that they never saw.
Sure.
All right?
So I was just the, uh,
I was just the little,
the little spoiled kid.
I was anything but.
And so I think that
was part of it, too.
It was sort of like, you know,
"Well, I'll show you." I go back
to that beautiful quote, right?
This, this beautiful
quote, and I've probably
shared this before.
I had overdone a
project in high school
significantly, significantly.
Okay.
And I was relatively new in
high school at that point.
I had overbuilt this
little model by, like,
I don't know, 30 hours.
I spent a ton of time
making this little panorama.
It was beautiful.
Everybody started making fun
of this thing, 'cause some of
them had, like, literally gone
to the library and photocopied
a, a piece of paper out of
a book, and that was their,
that was their presentation.
So everybody was
making fun of me.
The teacher hears this as
he walks in, and he stood
outside and he listened to
the narrative for a minute.
And he walks in and he goes,
"Go ahead, make fun of him.
Laugh now while you can. When
he's signing your paychecks-"
it won't be funny anymore.
And I thought, like, that was
such a beautifully validating,
going back to validation,
such a beautifully validating
moment for me to say that like,
look, putting in that extra
effort, being autonomous and
doing what I wanted to the way
I wanted to was okay, right?
Because up until that point,
I'm not sure I'd heard that,
and that was a really, really
important moment in my life.
Thanks, Mr. Adkins.
You're the best.
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 day
long at 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.
I think it's fascinating,
though, like again,
I, I'm mentioning som-
something like Steve Jobs.
I remember, this is, I'm gonna
date stamp it, like 2010.
There used to be a, a media
property called Valleywag,
and it used to be like
the TMZ- Oh, yeah ... of,
of Silicon Valley, right?
Yeah.
And so, and so there
was a writer back then,
uh, named Ryan Tate, and
I'll never forget this.
2010, 2011, it was
r- right around then.
He gets into a spat
with Steve Jobs.
Right?
Mm-hmm.
He's criticizing, like, the iPad
or something like that, right?
Right.
And Steve Jobs goes back to
him and he goes, "Hey, what
have you ever done? What
have you ever built?" Mm-hmm.
"First let's start with
what you've built- Yeah
and now let's talk about your
criticisms." And, and what
I loved about that, I loved
that even Steve Jobs was still
feeling that, like, like he was
getting pushed into a locker.
Yeah.
Right?
It hurt.
It hurt.
The, despite- It hurt, right?
... the absolute... And t- it's
so funny because he literally
in the next breath, like he's,
he's telling you that hurt, in
the next breath he's telling
you why that person's opinion
is completely irrelevant,
and yet- That's my point
and yet- Right ... it
still hurt, right?
It's so funny.
So I wanna talk about that.
I wanna talk about, like,
let's say that Steve Jobs
was, was guy that got pushed
into the locker, right?
And he wants to show the
world that, you know, he's,
he's bigger, smarter, you
know, all these things.
Yeah.
Uh, which is fine.
It's a perfectly
understandable behavior.
I'm not here to
criticize that feeling.
I'm here to, to
explain it, right?
Yeah.
And in his mind, if he builds
Apple, iPad, iPhone, uh,
all these things, right?
Then people won't be
able to say these things
to him anymore, right?
And here this, you know,
snarky Valleywag reporter,
right, gets under his skin.
Now here's why I say that.
Truer words were never
spoken by Jobs, right?
Yeah.
When he says, "What
have you done?"
Yeah.
Right?
That is exactly
the right answer.
It is.
What have you done, dude?
Yeah.
You're talking to the
guy that built Apple.
Uh-huh.
Fuck you.
Yeah.
Like, straight up, right?
So w- when I say this, when
people are like, "Hey, I have
to build for the haters- Yeah
I have to prove
them wrong," pause.
Yeah.
Who are those people
specifically, and what leg do
they have to stand on to tell
you who you are to begin with?
Yeah.
It took me a long time
to figure that one out.
Yeah.
A long time.
Right?
And I'm not sure I'm
totally over it, but
I know that- Criticism
still hurts, even, even when
you know it's coming from a
place of, of irrelevance, man.
Like, uh, like, if it can
still get to Steve Jobs, right?
Yeah.
Who's gonna be me?
That's my point.
That guy could have literally
been like, "You know the
iPad and the iPhone and the
iMac? I am the I in all of
those things, asshole." Yeah.
"Who are you? Which part
of Valley Wag? Are you the
wag or are you the valley?"
Yeah, yeah, yeah, yeah.
Right.
"Tell me."
Unbelievable.
The point though is that, like,
that ego still fuels him, right?
Yeah.
And, and Jobs is, you know,
famously an egomaniac, but-
Yes
...
I look at this a- and I
think to myself, "What's the
minimum viable product that
we need, the path that we need
to solve this ego problem?"
Yeah.
You know, minimum
viable ego, right?
There you go.
Like, if my ego is that I
feel like my parents always
treated my, my sibling
better than I did, and I
have to show them, cool.
That's fine.
I don't care what it is, right?
Yep.
But let's be very
deliberate about what path
will solve that problem.
Sure.
Right?
And so I, I can tell you
right now, it's, it's not
raising 200 million in VC.
Right.
Unless
Unless.
Yeah.
Unless your dad was
Steve Jobs, right?
Right.
A- and, like, a- and you have
to operate at that level.
That's actually... Uh, just
made me think about it.
Early in my career when I
was running the agency, I
was very fortunate to have
a great partner, a guy named
Blaine, who you obviously know.
Yeah,
yeah.
And the agency's doing
phenomenally well, right?
Like, we're making hundreds
of millions of dollars.
And, uh, Blaine, who was
super young at the time, I
think he was, like, 28, 29,
was like, "Hey, that's great,
but my dad, you know, started
Cardinal Health," which is,
like, what, like, the 15th
largest company in the world or
something like that- Oh, yeah
in the, in the US,
something like that.
Like, Fortune 15 company.
So, so we're basically
a rounding error- Yeah,
exactly ... at $100 million.
Exactly.
Yeah.
So, so his threshold for
what he had to get to was-
Yep ... like, you know-
Yep ... in the stratosphere.
And it was interesting because I
was like, "I don't think my dad
made over $1,000 in a month."
Right.
So, like- Yeah.
So- ... my threshold of what
I- Yeah ... needed to get over
to satisfy that claim was very
different.
I,
I have
to clear so many bars.
Right.
Exactly.
And so my point is everybody's
got, like, a different threshold
of what they- Sure ... think
they need in order to clear.
But what I always look at
it and I say, "Let's get
really specific about what
your threshold needs to be."
What it is.
Yeah, yeah.
'Cause I guarantee
it ain't that high.
Yep.
So I'm thinking, um, class
of 2005 dork that got pushed
into a, a locker and...
I wish I was that young.
I was gonna say, did, did
we just get younger, Will?
Yeah.
I think 20 years.
Nicerly done.
And that's what I'm trying
to like, like fight against.
I, I gotta prove
those haters wrong.
Number one, you'll never
prove them wrong, right?
Right.
It, actually, the Steve
Jobs example, right?
It- there are always
gonna be haters.
No matter what you do,
those people were haters
before you came around.
Yeah.
Yep.
And they'll be haters
long after you go around.
If, heaven forbid, today's
your last day on Earth, it's
not gonna change a thing
about who those people are.
Correct.
So like, it's, it...
Foolish to try.
But the other side of it
is, if really what you
wanna do is prove to your
old man that you can be
good enough, smart enough,
et cetera- Yeah ... cool.
What's the minimum
that would take?
Here's an example, right?
Probably less than you think.
Here's an example.
If you had a business that was
doing $5 million in revenue, on
$2 million in net income- Yeah
and you flew private, not all
the time, but you, you know-
Right, but you can ... you
could get your Marquis Jet
Card or you know, whatever-
Yep ... it was, right?
Would that be more
than your old man did?
Right?
Probably.
Or depending on who
your old man is, right?
Probably.
Then just do that.
Do that.
Yeah.
Dude, that's a
consulting company.
Yep.
That's it.
Right?
Like, like you don't need
to raise 200 million in VC
and go IPO- No, you do not.
You do not ... to get
to that
outcome.
You don't need to build a
rocket ship if all you're
trying to do is cross the
English Channel, right?
You just need- That's
what I'm saying, man ... a
speedboat, right?
Just pick-
That's what I'm saying.
You know, a lot of people,
when they start a business,
they're like, "My old boss
was an asshole, I'm gonna, you
know, prove to them," whatever.
Ironically, in many cases,
that old boss- Yeah ... is
probably you or I.
Yep.
And I get it, right?
It's like, "I'm gonna
show them that I've, I've
done this thing." I, you
know, I got a funny story.
Years ago, this developer
that worked for me, like 25
years ago, maybe like 10 years
ago, I saw him at a bar or
something like that, right?
And he had built a new
company, like a development
shop- Mm ... and they're
doing really well, right?
And he was like, "One day I
knew we'd see each other again,
and I needed to tell you,
you know, that I would prove
you wrong, that I did, you
know, that I, I was able-" Oh
"to do this," et cetera.
And I remember s- looking
at him like, "What are
you talking about?" Yeah.
Right?
'Cause he, this was like
his moment to like- Uh-huh.
Oh, God ... prove his old boss
that he could really perform.
And I was like-
Talk about taking the
wind out of his sails.
He spent so much time
hanging those sails, Will.
Good Lord.
I was
like, "I would be the
last person in the world-
Yeah ... that would not wanna
see you do that." Like, I
would be... He was like, "No,
you told me at the time it
could never be done." I'm
like, "Dude, you fabricated
all of that." Like, because-
I'm glad I was the villain that
drove you to s- your success,
but, uh, I, I had no idea
it was- Yeah.
Yeah.
I'm, I'm glad that you, you
invented the evil version of me.
Also, isn't it hysterical
that like- So often when
I see founders that are
like, they've tried to
prove they matter, right?
Yeah.
Yeah, yeah.
Why do they pick the hardest
possible way of doing it?
It's like- That's what I'm
saying ... like, there's
so many other ways to have
gotten around that, right?
Like, maybe just a
conversation with you
probably would have done that.
No, look, it- it's, he
needed some motivation
apparently, and so that's- Yeah
...
that's- No, that's
what it takes.
Yeah.
But, but I look at that
and, and I think to myself,
number one, I actually
didn't feel that way, right?
So like, uh- Yeah ... that
was a false pr- premise.
Number two, now that you
know that you've done the
thing, are you good now?
Yeah.
Because every single person
I've ever met has not been.
Uh-huh.
It goes back to when we
talk about founders who've,
you know, finally sold or
IPO'd or anything else like
that, and they all think
that it's that moment that's
gonna change everything.
Like, like, if I take company
IPO, then I wasn't the kid
that got pushed in the locker.
No.
Yeah.
No.
You took the company IPO and
you were the kid that got- Yeah
... that got pushed in the locker.
One doesn't like, you
know, n- reset the other.
And I look at that
and, and I'm like-
No matter how many zeros
are behind the first digit
in your exit number, that
photo from middle school
still exists somewhere.
Yep.
Right?
Yeah, it does.
It's not going away.
I was talking to s- somebody
the other day about this.
I'm building this new house, and
they're like, "Oh my God, you
must be so proud of, you know,
what you're building," stuff.
I'm like, "I am, but like,
I'm still price shopping
the cost of the outlet
covers that are going on-
on every outlet," right?
Yeah.
"I'm gonna save exactly like
$6, but like- Uh-huh ... hell,
I'm gonna price shop
all of those," right?
And they said, "Why?" Like, you
know, "You've got enough cash,
like it doesn't matter." Mm-hmm.
I was like, "Because I'm a poor
kid that made money." Yeah.
"But I'll always be the
poor kid." I understand
my DNA very well.
Yeah.
Doesn't mean I don't deal
with it like everybody else.
Uh-huh.
But I definitely
take account for it.
But you, you recognize it.
Right?
Yeah.
I recognize where
these things come from.
And when I rewind back and
I look at earlier points in
my career, it was hilarious
how many of my decisions were
driven by a version of me
that didn't quite get it yet.
Yeah.
Right?
Yep.
That was me in the yellow
Lamborghini, right?
Right.
It wasn't that I needed to
get places faster, right?
Right.
That wasn't, that
wasn't it, right?
And what's funny is now
that I don't have those same
insecurities, the idea of
owning a yellow Lamborghini
makes absolutely no sense.
It is funny.
It, like, I almost look
at it like in, like,
what was I thinking?
Yeah.
Right?
Yeah.
Take the douchebaggery off
the table for a second.
Sure.
I'm just looking at it now
like, I own a pickup truck.
Right.
Because it's really practical.
Well, that's not
your best vehicle.
Your best vehicle is by
far the skid steer, right?
The Bobcat is- But- ... by far
the best vehicle that you own.
That's even a
level
below- Like, that's my
favorite ... in some
way or level
up.
I wanna roll up to the club
in that thing at some point.
Yeah, right.
Right.
But I guess what I'm saying
is, as we start to understand
ourselves better, right?
Like, as we understand
where these motivations
are coming from- It's
incredible how different
our journey becomes- Yes
because we're solving
for different things.
Yeah.
Right?
I found, and I think a lot of
people get here, I found that
over time, the things that
I'm, like, optimizing for have
very little to do with wealth.
It's how I spend my time, like,
how I build my relationships,
and everybody tells you that.
That's
it right there.
Those two things.
Yeah.
Yeah.
That's it.
But that said, none of that
stuff means shit until you've
actually made some money, right?
Yeah.
Because until then-
Yeah ... not having cash
seems like the biggest
problem, so all those things,
you know, become a luxury.
It is up to a point, and
then, and then just isn't.
I think we, we've talked
about that before too, couple
times on the podcast, where
just, like, that number is not
nearly as high as you think.
But, but going back to this,
the, the entire kind of
minimum viable ego thing here.
Yeah.
I, I... In the way I think
about, the goal isn't
to eliminate the ego.
We're not saying like, "Okay,
you just almost- Yeah, right
... achieve ego death." The, the
goal here is to, to right-size
the plan to that motive, right?
Yep.
Whatever it is within the
ego that's driving that.
And so as we've been talking,
as I was thinking of a couple
of questions that I would, I
would probably ask founders or
myself, really try to get to the
other side of this, which is,
like, what am I trying to feel
on the other side of success?
Yeah.
Right?
Like, that, the
un-dorking, right?
Like- Yep ... what will
actually make me not feel
like the dork anymore, right?
Right.
Second, like, what's the
smallest outcome that would
genuinely satisfy that, right?
To your point-
Yep
...
we don't need a $200 million
raise from VC if what we need
is a $5 million business with
two million EBITDA and our
Marquee Jet Card so we can make-
Right, wh- which
isn't a layup either.
I, I don't wanna point that as
th- like, that's a concession.
Dude, if you get there, you're
in the top 1% of people.
Yes, but you're not in the
top zero, zero, zero point,
or .0001% of people, right?
Yep.
It, it's going back to, like,
what, what path gets me there
with the least risk, time,
and self-destruction, right?
I think is the other one.
Because I watch so often,
because founders don't
acknowledge this ego that's
driving from the trunk, that
the self-destruction becomes a
natural byproduct of that, and
that's really, really hard to
watch when you just understand.
When you can see it from
the outside, 'cause so very
frequently you and I are talking
to founders, and we can kinda
see these motivations and go
like, "This one's really got
a chip on their shoulder.
They've really got something
to prove here." Yeah.
And I hope they go prove it,
but I don't wanna see them wreck
themselves in, in the process.
Do you know, Ryan, do
you know that I've never
seen anybody prove it?
I mean, okay- Yeah ... you
gotta understand, like, we're-
Yeah ... in the business of
seeing- In the business, yeah
the most successful
people become- Yes ... the
most successful people.
Yep.
I have yet to see anybody at
any level of success be like-
Yeah ... "I'm good now." Right?
Yeah.
If anything, it
actually made it worse.
Right.
Remember that quote from,
uh, Chesky from Airbnb saying
that, like, when he went public
at Airbnb, it was, like, the
loneliest, darkest- Oh, yes
you know, moment of his life
because- Yeah, yeah, yeah ... he
thought that was gonna solve
all these problems- Yep ... and
it, like, it actually, it
laid all the problems bare.
Bare,
yep.
Because if, if you've checked
all those boxes, and you've
made all that money, or you've
done whatever you said you're
gonna do, and you still feel
like crap, that makes it worse.
Because now there's no
s- there's no solve.
Right?
Yeah.
Like, you, you know, you're
as- you assume that I don't
have money, so if I have money,
then these problems go away.
Yeah.
But all of a sudden you get
the money and you still have
the problems, and now you're
like, "Shit, I actually can't
get rid of these problems."
Yeah.
At least before you
thought you might.
Right.
Yeah.
Before I see it-
That's the thing.
You get the hope of it,
of it disappearing, and
then when it doesn't, then
desperation doesn't creep
in, it comes, it comes
crashing in big Pacific wave.
You
bet.
I see it in marriages
all the time, right?
Sure.
I see it in marriages where
there's, there's a lot of
tension be- between the
spouses because there's money
problems and everything.
And look, man- Yeah
... life's hard, right?
I get it.
Yep.
And the idea is that if
we had more money, the
problems would go away.
Don't get me wrong.
Yeah.
Right?
Like, while money doesn't
solve every problems,
e- every problem, it
sure does create plenty.
Yeah.
Not having it
creates a lot, right?
Yeah, yeah.
So I, I, I don't wanna take
that off the table, but the idea
is that if we get the money,
it'll solve all of our problems.
And it'll solve some of them.
Right.
It'll solve the ones
that money can pay for.
It won't solve any of the
ones that money can't pay for.
Money
can't
pay for.
Yeah.
Right?
Or like, "Hey, let's ha- let's
have a kid and that'll bring us
closer together." No, it won't.
Yeah.
It's just gonna create a
whole new problem set that you
didn't have five seconds ago.
Yeah.
Right?
Um-
Third
person to argue
with.
No one's ever saved a
marriage with a kid, right?
S- And... But again, I look
at that seeing, like, people
look at these external factors
that can solve the things
that are personal to them.
Yeah.
And it, like, kinda never works.
It doesn't.
And it's bananas to me to,
to not take inventory of it.
It's hard.
It's- Right ... hard
work because it's
vulnerable work, right?
I think most of us, as
founders, would rather just
continue to grind than to
get honest- Yeah ... about
those things in particular.
But when you know what you're
actually building for, I, I
think you stop wandering into
the hardest possible version of
success, maybe that one that you
don't actually need to achieve
to feel successful, and start
building the right version
of success on purpose, right?
And, and the goal isn't
to become- Imagine that
... ego-less again, right?
It's to become-
Yeah ... aligned.
You know, to me, the most
unstoppable founders aren't
the ones, you know, with just
the, the biggest dreams, right?
We, we know that doesn't work.
It's, it's about the probability
of it actually coming true.
It's people who are actually
operating with some sense
of the truth behind what's
driving them forward, right?
Yep.
They understand what fuels them.
They can harness that fuel
and do something good with it.
Yeah.
I, I look at it, man, and
I say, for me, at any point
in my life, whether I was
making money or not, all
that mattered was my freedom
and my autonomy and really-
Yeah ... my, my ability to
control my own destiny, right?
Yeah.
That's it.
That's- That's it ... dude,
that's all I cared about.
Right.
To this day, it's
still all I care about.
Yep.
If you were to say, "Look,
you could take anything that
you have, and now you have
a 10th of it, but the one
thing you still have is your
autonomy," I'm like, "Shit,
that sucks, but I'll take- Yeah
the autonomy over everything."
Conversely, if you said you
could have 10 times more than
you have, but you have a boss,
so to speak, or you have, uh,
you don't have control of,
of your own destiny anymore,
I'm like, "Not interested."
Like, literally the only
thing that matters to me is
having that control of, you
know, of my destiny, of,
of whatever it's gonna be.
You know, even if the job sucks,
so long as it's my job- My job.
... I'm totally fine
with that, right?
Yep,
yep.
And I think that honesty that
I've developed over time has
served me incredibly well
because it allows me to say,
"No, I'm doing these things for
this specific reason." Uh-huh.
It sucks.
It puts me in a tough
position a lot of the
times, but I understand why.
I don't think I
did before, right?
And I think for a lot
of people, they'll look
at this, right, Ryan?
And they'll say, "Yeah, but
you shouldn't solve any of this
with work. You know, you should,
you should be able to fill your
bucket with- Yeah ... life,
with family, with all of those
things," and I think that's
exactly the right answer, and
I think it works exactly never.
Yep,
0% of the time.
Yeah, it's, it's
beautiful on paper.
It's a lovely, lovely sentiment.
Yeah, it's a great hallmark
moment, and it- Yeah ... works
pretty much never, right?
For the rest of us who aren't
quite that zen- Yeah ... um,
which is literally almost
everybody, here's what I say.
It's okay to have
these problems.
It's okay to be the dork in
2005 that got shoved into
a locker, and that's okay.
Yeah.
So long as you own it.
Right.
So long as you s- y- you
say to yourself, if not
the world, "This is what
I'm doing it for." Yeah.
"I, I'm getting up in the
morning, right, and I'm
gonna prove to everybody
that I wasn't that person.
I'm gonna prove to my old
man that I was good enough.
You know, I'm gonna prove
to whoever I have to prove
something to, but this is
why I'm doing it, and this
is exactly how I'm gonna get
there." And when that moment
comes that I can finally
say to myself, "Yes, I am
no longer the dork of 2005.
I have officially un-dorked
myself," then all of that effort
will probably be worth it.
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