Startup Therapy

What are you actually willing to do to get what you want as a founder? Using Will’s 6:00 a.m., 15-degree framing session and a dumpster-diving Bobcat mishap as metaphors, this episode breaks down what separates founders from everyone else: an “unreasonable” willingness to do hard, risky, uncomfortable things repeatedly—often without any guarantee of payoff. The conversation explores the real price founders pay (uncertainty, rejection, sacrifice, and daily grind), why high achievers used to clear reward loops can struggle in startup chaos, and why outsized outcomes tend to follow people who endure what others won’t. They also unpack common misconceptions about wealth and merit through examples like Jason Calacanis, Elon Musk, and elite athletes, and argue that the deeper reward isn’t money—it’s autonomy and ownership of your outcome.

What to listen for:
02:13 Nothing I'm Not Willing to Do
04:41 Why Founders Get Paid
09:47 Rejection and Being Wrong
12:31 High Achievers vs Founders
15:58 Building the Willingness Muscle
18:45 Willingness Beats Talent
29:36 Real Reward Is Autonomy
32:51 Aspiring Founder Reality Check
34:52 Worth It in the End

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What is Startup Therapy?

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 another episode
of the Startup Therapy podcast.

This is Ryan Rutan, joined as
always by Will Schroeder, the

founder and CEO of Startups.com.

Will, let's start with a story.

It's your story, but I'm
gonna start telling it.

It starts with this
line: Founders do what

others won't, so they
can do what others can't.

Now, let me set the
stage, 'cause here's

where that line got said.

It wasn't in a boardroom.

It wasn't on a stage.

Will, you were probably standing
in a half-built master bedroom

in your own new house, framing
an interior wall by hand.

It's 15 degrees outside.

It's Saturday at 6:00 in
the morning, and there's

a young aspiring founder
standing next to you asking

a very reasonable question.

Maybe the most reasonable
question in the world Why

are you doing this yourself?

You could just hire someone.

Now Will, you being you,
probably put down the nail

gun and said, "Pull up a
chair and let old man Will

explain something to you."
So today on the podcast, I

want to talk through one of
the things, maybe the thing,

that separates founders
from everybody else, and it

may not be what you think.

It's, it's not talent,
it's not the genius idea,

it's not luck for sure.

It's a willingness to do
the hard thing on purpose

over and over and over
again- … when absolutely

no reasonable person would.

I'm Ryan Rutan, and that
guy over there somewhere in

this screen is the guy who
frames blizzard, yeah, walls,

uh, frames walls in his
house in blizzards for fun.

Yeah.

Let's talk about the price of
that, of that framing, Will.

Yeah, yeah.

So I, I love that opener.

Okay, so this really was…
I mean, you've lived with me.

You've been on site- Oh, yeah
… helping me build this house.

But,

um- I, I only come in the,
in the warm seasons though.

I'm, I'm a shoulder- Yeah,
yeah, 'cause you're smart

season guy.

I'm not coming in
winter or summer.

Yeah.

But

yeah, I mean, literally
it's 15 degrees outside.

It's Ohio, and it's the, the
dead of winter of course,

and it's Saturday at 6:00
AM, um, the crack of dawn,

uh, barely light outside.

And I, I had hired another
guy who, uh, was an aspiring

founder, but also happened to
be an electrician, and knew

his way around a building
to just give me a hand.

You know, help me lift-
Yeah … heavy stuff.

A- as we're talking about
it, 'cause we're b- we're

building this, you know,
r- really beautiful house,

and he's like, "But dude,
you're, you're literally

framing this thing," not the
whole thing, I was framing

a s- specific section- Yeah,
yeah … um, uh, "yourself.

There's like no one else here."

Uh-huh.

"It's not like there's
a whole crew of people.

You're-" Right … "the
only person-" You're just

chipping in.

Yeah.

Yeah, yeah, yeah.

And he's, he's like, "Why?"
Like, like, "Why would you do…

You could clearly pay someone
else to do it, right?" And

that's when I was explaining to
him, I said, "Look, man, there

are a certain class of people,
and maybe you're one of them,

who are willing to do anything."

And it… I remember I told
him this specifically as

I was chattering 'cause
I was so freaking cold.

I remember saying like, "Look,
man, um, there's nothing

I'm not willing to do."

Yeah.

Right?

"And that makes me dangerous."
And, you know, let me

elaborate on that a little bit.

Like, there's a condition
for a lot of people where

there's a, a lot they're not
willing to withstand- Oh,

yeah,

yeah, yeah

and I don't wanna call
that a vulnerability

'cause it's actually
pretty reasonable, right?

Yeah.

There's people that won't
run through an actual fire

like firemen do, right?

Because it's super reasonable
to not wanna do that.

Yeah.

But thank God there
are people that do.

Right.

But, you know, there's,
they're few and far between.

And I said, "In my mind,"
uh, and again, I've been

doing this for a long time,
"it doesn't occur to me that

you wouldn't do something."

Yeah, yeah.

Right?

Like, if it needs to be done.

I'll, I'll give you one

example- Boundaries

are meant to be crossed.

Right.

This would end up coming
up, like, months later.

You remember, like, I, I bought
the, the, the Bobcat, right?

For those of you that don't
understand, like a mini tractor.

And I had the pallet forks
attached to it, and I was

lifting this huge, huge,
uh, load and dumping it into

a dumpster we had on site.

Well, I forgot to lock it
down, so as I, I lift up this

huge thing and I tilt the, the
pallet forks forward, the entire

assembly falls off the front of
the, uh, the front of the Bobcat

and into the trash, right?

In the trash, yeah.

In this full dumpster, right?

A seven-foot tall dumpster.

Yeah, exactly, right?

And I immediately jump out and I
hurdle the side of the dumpster.

I didn't even look to see
where I was jumping into,

which I wouldn't recommend.

Uh, and I'm going to retrieve
my pallet forks, which-

Yeah … weigh all of,
like, 400 pounds, right?

So I gotta figure out how
to get it out of there.

And so, uh, my friend, a guy
who you obviously know, who was

helping me out, was like, "I
remember watching you in that

moment," 'cause, you know, he's,
he's, uh, helping out outside.

Yeah.

He's like, "You didn't hesitate
to jump into a frigging

dumpster-" Yeah … right?

To do whatever you needed to do.

Just to

get what needed
to be done, yeah.

I was like, "Yeah, 'cause it
needed to be done," right?

And I say all this as
a preamble to say, as

founders, we've got a certain
willingness to do gnarly shit-

Yeah


that other people simply
don't have, right?

It's the same way like
people play in the NFL.

You have to be okay
getting in a car accident

every single weekend.

Every- I'm not, right?

Like- Yeah … I'm not okay
with that at all, right?

But there are people-
Well, to be fair, that's

a car accident we probably
wouldn't survive, Will.

Those guys are built
slightly differently.

Yeah, yeah.

I'm also not, not built
like an NFL player.

But, but I guess what I'm saying
is really a lot of what we'll

talk about today is why is it
that some people are willing,

and later on conditioned, to
accept the level of, of risk

and pain and everything- Yeah

else that comes with this,
and most people aren't?

And then the kind of connective
tissue to that is that's

why they get paid so much.

Yep.

That's why they get
the outsized rewards-

Yep


because they have
that willingness.

So if that's the case,
why are so many people so

unwilling is the question.

That is the difference, right?

Because everybody has- Yeah
… the option to frame the wall

themselves or dive- Yeah … in
the dumpster or- Yep … take

the hit, but- Yep … almost
nobody takes it, right?

Right.

And that gap is sort of
the entire job description

of a founder, right?

That's exactly it.

That willingness what
it is that we do.

Right.

Management was never the skill.

The advantage- Right … was the
thing that you're willing to do

the thing before you even know
what you're jumping into, right?

Literally, the, you know, the
most people build a house.

Will, you built a
house and a metaphor.

That's really efficient.

I appreciate that you provided
us with all this material.

Right?

But like you were willing to
jump into the dumpster without

knowing what was inside,
and that is an absolutely

perfect metaphor for what
it is that founders do.

Right.

I think what's interesting
about all of this is everyone

looks at, you know, these
founders that have done

extraordinarily well, and
they only see the, like, the

output, which is, "Hey- Yeah

I built big company," or,
"I've got, you know, private

jet," or something like that.

They don't understand why
they don't have it, right?

And so a lot of people are like,
"Well, how do I get what w- you

know, what you have, founder
person?" And it's like, dude,

a- actually, you know what?

I get asked this
all the time, right?

You know, 'cause building a
big house- Yeah … a lot of

contractors, I talk to all
of them 'cause I'm on site

all the time, and they always
ask me, "Hey, man, like, you

know, how do I get a house
like this?" And I'm like,

"Honestly, it's dead simple."

Uh-huh.

All you have to do is spend
30 years doing nothing but

working night and day, give
up all your relationships,

give up your entire life,
and risk everything you have

night and day, and it's easy.

Practically shows up for itself.

That's it.

And they're like, "Oh, well,
I don't wanna do that."

Yeah.

N- never mind.

It's fine.

I, I don't want that.

I don't blame you because
you're a reasonable person.

And so- A big part of what
I talk about when I talk to,

you know, aspiring founders
is the price of willingness.

Like, that's really
what this is about.

You said it in the
intro, which I thought

was really appropriate.

It's not like I've got
the best idea or I'm the

smartest person, et cetera.

It's I've got a willingness
to endure some gnarly shit

over and over- Yeah … and
over for a really long time.

Yeah.

And it's like a lot of people
can run a 5K, but there's

a reason very few people
make it past the finish

line of a Ironman triathlon.

Right.

A lot of people can run.

Yeah.

Very few people, myself
included, can't run like that.

Willing to just push through
all that you have to push

through to do that, right?

Yeah.

Yeah.

Look, everybody wants
a destination, right?

Yeah.

But the price is the road, and
it's where 99% of people end up

turning around at some point.

And I think one of the, the
really interesting things

about our space is that you
don't necessarily see the price

when you enter into it, right?

Like, say you wanna
become a doctor.

You sort of know the price.

There's med school, there's
the, the residency- Yeah

… there's all this stuff, right?

Which isn't insignificant.

You kind of lay it out there.

You sort of know- Yeah … what
you're gonna have to go through.

A lot of other people
have gone through more

or less the same thing.

The founder journey is so,
so unique, and really, you

know, the price of admission
isn't, isn't money, right?

It's money you can raise.

Yeah.

The, the price is
uncertainty and- Uncertainty

or, or certainty, I guess.

The, the opposite.

And, and nobody
can lend you that.

You can't get that from
anywhere, and you just have

to be willing to keep push,
as you keep saying, beyond

the point of reason, right?

Because reasonable people
are like, "You know what?

We've been doing this for a
really long time, and you said

it's around the next bend.

We can't even see the bend yet."
Yeah. "So I think we're gonna

head back the other direction.

There was a gas station
back there, and they had

snacks." "So we're gonna go
get some snacks." Like, fuck.

Let's take a, a doctor's
path, for example, right?

Sure.

Which I have a tremendous
amount of respect for.

It is long and arduous,
there's no question.

Yep.

But you know what the path is.

It's certain.

Imagine going through that
entire path, and at the end

of it, you're not a doctor.

What am I now?

After 12 years, what am I?

And they just hand you, like,
a rubber hammer, and you're

like, "You're… We don't
know." And you're like, "Oh."

You're a carpenter now.

Shit.

What?

Yeah.

What?

When people try to, like,
make those comparisons, they

always put it one-for-one with
the outcome being certain.

They're like, "Oh, well, I
worked just as hard as you did,

and here's what I got." Mm-hmm.

I was like, "Well, you did.
I don't question the amount

of work that takes." Yeah.

I don't question the effort
it takes from someone to go

th- through law school to
make it out on the other side.

It's a lot of work, man.

Yep.

Right?

And I don't… The difference
is you know what you're getting.

There's a finish
line and a prize.

Correct.

Right?

And it's the same every time.

Right.

And maybe in an undergrad
you don't hit your LSATs

quite the way you thought you
would- Yeah … or your MCATs,

you know, to go whatever.

O- okay.

But you know what
that's going to yield.

And yes, you racked up debt,
but you knew exactly what

your payment was gonna be.

Yeah.

And you knew that at some point
that debt would go away, right?

Because you would ideally
make more money, et cetera.

This is the opposite.

I'm gonna rack up all the debt,
probably go completely bankrupt,

and have nothing to show for it.

Yeah, yeah.

I don't have a
marketable degree.

I have nothing.

And that uncertainty is
a big part of the price.

Now, I'm gonna put that as one
category of the price, right?

Th- that again, a lot of
people don't see unless

they've gone through it.

Another category of the price
would be the amount of rejection

that comes with this job-

Yeah

on a consistent basis.

You know, it's constant.

Do you

like being wrong
most of the time?

Well, y- We've got
just the job for you.

Exactly, right?

Now, like, again, let me compare
this to a, a med student.

Med student's gotta, uh, crush
all kinds of tests, et cetera.

Yeah.

But you know for certain that if
you study and you answer A- Yeah

and the answer is A-

Yeah


you get an A, right?

Yeah.

How about every single
time you answer something,

the answer's wrong no
matter how hard you worked?

Yeah.

Or, or there- Right?

… mightn't even be an answer.

There's just a question.

Right.

Right?

And then there's, like, is
there an answer to this?

We don't know.

We just have to keep answering
until we find out, right?

It's maddening.

It's not even just
the uncertainty.

It's the uncertainty
without even understanding

whether there's an endgame
to the uncertainty.

Yeah.

Right?

It'd be like studying for a
test that you never take, right?

Right.

You're just studying.

They're like, "Yep,
there's no test." "Well,

what did I study for?"

"No reason."

Yeah, yeah.

"
I'm moving

on." Don't worry.

Just keep studying.

It's like, o- okay.

Or like I said, you
studied for the test.

You got every answer
right on paper.

Yeah.

But when you handed it in,
every answer was wrong,

and there's no way you
could've gotten it right.

Um-

You can't, and you
can't see it from the

beginning either, right?

I think that's the part
that, like, maybe just

isn't all that clear.

Like you can empty your
savings or pour all your

time or whatever into an
idea, and that either becomes

a really cool founding
story or a cautionary tale.

You don't get to find
out which one for like

years, maybe a decade.

Right.

Then, then you understand which
one of those two things it was.

There are very few job paths,
career paths that actually

have, if not no ending-
Yeah … or a negative ending.

A lot of people are like, "Yeah,
well, I hate my job." Okay.

But you get paid.

Yep.

Right?

Like, it's not like on
Friday when paychecks come

out, sometimes you get
paid, sometimes you don't.

Yep.

And if that ever happened once,
right, I don't care if you

work at frigging Arby's, right?

Yeah.

You'd never go back
the next week- Don't go

back … and do it again.

Nope.

You wouldn't be like, "Yeah,
I've been at Arby's for,

like, about three or four
years now. It's been really

tough. I'm really grinding,
and, you know, they haven't

paid me yet, but, uh, you
know, I'm really hoping that,

that this is gonna pay off."

Yeah.

Like, nobody would-
Nobody … ever do that.

No.

It doesn't even sound reason-
And- Like, no one would

think that you should, right?

I think that's what's- Correct.

Right … what's so
insane about what we do.

And so, like, again, when,
when people look at what we do

as just the outcome, not the
input to get it, even people

who I, I would argue are high
achievers in their own right,

like, you know, again, an
attorney, a doctor, or whatever-

Yeah

they at least have a path
that has a very clear

outcome and a reward.

Maybe the reward isn't as
high as they wanted it to be.

Yep.

And, you know, I, I can't
speak to that 'cause

individual expectations.

But at least they knew there
was some level of reward.

You know what?

Stick on that for a second
because, uh, there's actually

something really interesting
about the high achievers,

and it's why I, I think you,
you actually see less high

achievers, like the traditional
high achiever type- In the

founder space because they were
used to a system that provided

fairly near-term rewards.

Take test, get grade, feel
good about grade, move on,

take next test, get the
graduation, get the degree, get

the job, just keep moving up.

Like, they're in
that, like, relatively

short-loop dopamine cycle.

Mm-hmm.

And, and I think that when you
look at the high achievers,

you don't see as many of them.

Now, a lot of founders achieve
a hell of a lot of stuff, but

you and I both know plenty
of people who you never

would've looked at and been
like, "Super high achiever."

They're amazing founders.

Yeah.

Right?

Yeah.

Which goes back to what
we were saying at the top.

Like, it isn't just about having
talent or genius or whatever.

It's about having that
willingness to just

keep going, right?

It- Because most
people can answer.

Like, we, we… I ask
founders all the time,

like, "What do you want?"

Right?

"What is it?

What do you want?

What are you trying
to do with this?

And what is it you're
actually trying to achieve?

I know you wanna build a
business, but, like, what

behind that?" Instant answer.

Like, they almost always
have exactly what it is

they think they want, the
goal, the, the outcome.

Right.

And you ask, "What'll
you give up for it?"

And all of a sudden people are,
like, checking their phones.

They're doing anything
but looking me in the

eyes and answering.

At that point they're like,
"Oh, I, I don't, I don't

know about that part yet."

Yeah, yeah.

I don't wanna pay the price,
but I d- fine with the paycheck.

But I think what people also
miss, when they do these founder

stories, and there's, you know,
it's always the same story.

It's, "I came from nothing.
I, you know, hardship, then

moment, and then everything
went well." Like, the, it's

always the same arc, right?

What gets lost on those stories
is we often look at that time

of hardship as just this,
like, snap moment in time.

Mm. And you hear the founder
say something like, you know,

"W- we burned through all
of our savings," as if they

just walked into the bank,
wrote a check for all their

savings to somebody, right?

And that was the entire moment.

Yeah, yeah.

I was like, "Dude- Not exactly.

Like- There were so many brutal
traumatizing moments along

the way, and a lot of stuff
people don't talk about when

they do those really, you know,
those great- Sure … origin

stories, like the relationships
that they lost, the depression

they went through, like- Yeah

really hard PTSD level stuff.

Sometimes added together, right?

It's not like, "Well,
pick one." Yeah.

Right?

It's like- Yeah … "No, no,
you get to draw as many of these

as you'd like. A- actually- You
bet … you get to draw them all

whether you like them or not."

Yeah, yeah.

The thing is, it's happening
every single day, day

after day after day.

And I think for folks that
just don't have the tenacity

for this- Yeah … they
look at that, and they're

like, "Yeah, I'm not…
That… Fuck this." Right?

Yeah.

And again, I would go back
to you fall into a category

of reasonable people.

I, I'm not, I'm not pointing
your finger like, "Hey,

you're not good enough."
I'm like, "No, that's

actually a pretty reasonable

response."

Yeah.

You just, you fit
somewhere else.

Yeah.

We had a guy working on site
at one point, and, um, he's a

framer of all things, and he
was afraid of heights, which

is odd if you're a framer,
right- Yeah … 'cause you

go up multiple levels, right?

Uh- I

specialize in ranch
homes, flat roofs.

Teepees.

I was like, "Honestly,
that's a very reasonable

thing to be afraid of-

Yeah

because it's high, right?

Yeah.

Like, it's dangerous, right?

It's

dangerous.

Yeah.

It, it- It'll kill you.

Yeah, and those rafters are
covered with snow right now.

And so I look at the same way.

I'm like, "Look, you know, what
founders do, to, to be afraid

of doing that or unwilling to do
that is a very rational thing."

Again, I said firefighters,
you know, run into a fire.

Military runs at fire, you
know, like- Yeah … people

firing at them, right?

The irrational person
is the person that's

willing to do that.

Right?

The rational person's
like, "No, thank you. Maybe

someone else." But here's
what gets interesting.

Once you start to build
that muscle, and I would

equate this to, like, a
distance athlete, et cetera.

You know, once the distance
athlete, like a triathlete,

has realized that they
can make it past this-

Yeah, yeah … milestone,
this milestone, this, this

milestone, it also puts them
on the other side of things.

If they really realize what
this means, "Hey, I've got a

gear most people don't have."

Yeah.

"
I'm willing to do shit
most people aren't

willing to do," right?

Yes.

That puts me in a different
class of competitors-

Yeah


than everybody else.

The problem is, for most
people, until you do it,

you don't really know.

Right.

Right?

Like, I can say I'm gonna go
do a triathlon, but- … until

I cross that finish line,
I don't actually know.

Yeah.

I don't

actually

know.

Not hard to sign
up for a triathlon.

It's not.

Yeah.

And so I think f- uh, same with,
you know, starting a startup.

You're like, "Ah, I'm gonna-
Yep … do a startup."

Eh, good luck with that.

And, and I genuinely
mean good luck with that.

Yes.

But I also mean, like,
starting is the easy part.

Yep.

It's finishing it
that's pretty expensive.

But I think when people
trivialize the amount of

effort that goes into s-
again, 'cause th- Yeah

they look back and they're
like, "Well, it couldn't have

been that hard," or, you know,
"It couldn't have been that

risky," or, "It couldn't have
been that whatever," or you

wouldn't have kept doing it.

Oh, but it was.

Or the opposite.

Yeah,

yeah.

And

I

did, right?

And I did, right?

That's what makes it
something special, right?

Yeah, yeah.

That's why we get
asymmetric rewards.

That's why very
few people do it.

That's why failure rate
for startups is so high.

Y-

you know who doesn't
question that?

Other founders.

Yeah,

yeah.

So, you know, we do all these
different founder groups and

I, and I've run these groups
for a long time, and one of

the cool things, one of the
coolest things really, is when

we're in the founder groups,
the live founder groups, like

in person, and there's eight
founders around the room,

or sometimes more, sometimes
30 founders in a room.

Yeah.

And one of the founders,
you know, we prompt them on

this, uh, raised their hand
and said, "You know, here,

here's something I'd like
to share, like, you know,

a, a high-five moment that
I'm really proud of," right?

It's not just how every
other founder responds

wh- when they hear that.

It's how that founder, often
for the first time, is finally

in a room that genuinely
appreciates what they just did.

Yeah.

Right?

Yep.

And it goes the other way, too.

When someone in the room, one
of the founders, is sharing and

it's something super brutally
hard, maybe they're shutting

down the business or, you know,
or something else, every person

in the room really appreciates
what that actually means.

Yeah.

Yeah, what that
actually represents.

Y- y-

you, you bet.

And when things aren't going
well, when things, you know,

go the opposite direction, the
founder's shutting things down

or whatever else like that, I
always remind that founder at

that moment, I said, "Remember
this moment." Because there's

gonna be a time when you're
telling your origin story-

Mm

right, how you came back from
this and how you built this,

and to be fair, many, many do.

Remember this feeling.

When someone says,
"It must be nice."

Yeah.

Right?

And I implore you to make
sure you remember this moment

when you're mouthing the
words, "Go fuck yourself."

Yeah.

That's exactly it,

man.

Yes.

That's kind of it, right?

God.

And now, well, you know, when
I think about the founder

space, like, yeah, it just
would… People ask us all

the time, I'm sure you get
the same question, is like,

"What does it take to be a
good founder?" What, what does

it take to be a good founder?

And man, I would take a
person of average talent with

an absolutely unreasonable
willingness to just do,

over some genius who needs
perfect conditions, right?

So the person- Yep … who's
like, they're, they're trying

to perfect it, they're,
they're lab benching,

they're doing whatever.

And I'd do that every single
time because willingness,

willingness compounds.

Talent just sits there-
Huh … waiting to be motivated,

but willingness just gets
out there and just does shit,

which always, always, always a
benefit to a startup company.

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 gotta tell you, this is,
this is gonna sound like an,

a odd high-five to someone,
but someone who has that

tenacity and is where they are
because of their tenacity- Yeah

and some of the people that,
that watch this, uh, knows,

is Jason Calacanis, right?

Oh, yeah.

Now, now, a lot of people don't
know where Jason came from.

Yes.

Right?

But Jason was not silver
spooned by any means.

Nope.

And I remember, this
is, God, this has to be

like 20, 25 years ago.

I'm in Santa Monica, I'd
just gotten there for the

first time, and, uh, Jason
Nazar was interviewing-

Yeah

Jason Calacanis on stage.

And it, there's maybe 80
people in the audience, right?

And I, I'd met Jason a
couple times before, but

I didn't know him well.

But Jason Nazar is a phenomenal
interviewer, uh, which is

ironic 'cause he's interviewing
a guy who's gonna end up

interviewing everybody.

And, um, Calacanis
gets up there.

He tells this story
about where he came from.

I think he said- Mm … like,
dad, if I can remember the

story, his, his dad was like
a bar owner in New York or

something like that, and
kinda came up like a rough

and tumble kinda in a way.

Yeah.

And fast-forward to today,
Jason's on a very popular

podcast with all billionaires.

Yeah.

And think about what he had to
do to make that happen, right?

Yeah.

And Jason's got a big
personality, right?

He's actually a surprisingly
kind guy, but, uh, given

his personality, he's, you
know, uh, pretty gruff.

But he got there through
pure fucking hustle.

He's smart.

Yeah.

He is smart.

Yeah.

I'm not, not, not taking that
away from him, but that's not

how he got there, because- You

can be smart and not have
hustle and go nowhere.

Do you know that back in the day
when Jason was doing Silicon,

uh, Alley Reporter, which
was, like, you know- Uh-huh

… way, like, the '90s, right?

This is like- Yeah … the '90s.

He was running around New
York dropping off printed

copies of his publication
at offices, right?

I mean, that, like, pure
frigging hustle, right?

I love

it, man.

And I remember when we
bought Zirtual, Jason was

on the cap table of Zirtual.

Yeah.

He was an investor in Zirtual.

And Jason and I were at
breakfast, like, uh, af-

after we'd done the deal.

We were at breakfast
in San Francisco.

I swear it was Christmas Eve,
for as bizarre as that sounds.

Like, uh, uh, whatever, uh,
whatever to do it, right?

And Jason was like, "Will,
what I love about you is you've

just got this hustle," right?

Like, this, you
know, like this grit.

And I was like, "Jason,
you've got the hustle." Yeah.

Like, and I was- That's what

I love about you.

Yeah, yeah, yeah, yeah.

Yeah.

Yeah, and I just, um-

We must be founders.

Yeah, yeah.

Well, well, that's
what I'm saying.

So it was just, like, two
founders just, like, like,

uh, you know, just recognizing
what it took to get there.

It's interesting to me, because
for someone like Jason, who

ended up getting… And when
I say ended up, I mean that

was the outcome, not like it,
uh, like he didn't earn it.

Had an asymmetric reward.

You know, f- for, for
those of you that aren't

super familiar, Jason was,
like, in the seed investor

team for, um, Uber, right?

Yeah.

Which was, at the time,
maybe one of the greatest

investments there were, right?

And, and if I recall, he
brought Sequoia on board and,

and all this other stuff.

But that hustle put
him in the room, right?

Yeah.

Jason didn't have the
money back then to make

those kind of investments,
but after that he did.

And that- Yeah … which is
how he became, you know, the

Jason that we know today.

But what's interesting
about that is Jason hustled.

Jason did really hard
shit that other people

weren't willing to do.

Yeah.

Because of that, through Uber
and then other investments after

that, got this massive reward.

Now, there's gonna be
some number of people that

say he didn't deserve it.

Right?

Like he doesn't deserve
that wealth, he doesn't

deserve that whatever.

Yeah.

And I'm like, a- and again,
uh, it's not that I'm like

super fanboy of Jason, he's
a good enough guy, right?

But I'm like, dude did
shit- Yeah … that

you weren't willing

to do.

He did things that other people
weren't willing to do to get

in the position to be able to
do that in the first place.

It wasn't they were just
like, anybody with 10,000

bucks can just come in and
just w- w- we're… It was a

very specific set of people
who were in the right place

at the right time doing the
right things that earned

those opportunities, right?

That- And, and it's not
like he hadn't earned

it before that, too.

Now that attitude- And
that- … we've talked, I think.

Did we talk about that
la- was that last week

or the week before?

I don't-

I think we were
talking about Musk.

And, and people were
like, oh, he doesn't-

Yeah … deserve his money.

Like, and again, I don't
give a shit about Elon Musk.

I'm not like, you know,
defending the guy.

Yeah.

But I just practically
I look at it and I'm

like, do what he's done.

He created that money.

Yeah.

Yeah, yeah, yeah.

Right?

So, so if he's not
entitled to it, who is?

Should we just give
it back to people?

Are they gonna give us
back- Well, well- … parts

of the cars, parts
of the, the aircraft?

What are they gonna do?

Well, he's really just
making the money off the

backs of his employees.

Dude, if that's the case,
sign me up to be that

back any day of the week.

Yeah.

Yeah.

Do

you know how many millionaires

he's minted?

He did a whole… How many?

Like, it was, it was a very
large number of millionaires

were minted during the IPO.

So the SpaceX IPO minted at
least 1,000 millionaires.

Do you know how frigging
hard that is to do?

Yeah.

Right?

That's, that's pretty

hard.

And s- and I wanna say over
100 centi-millionaires.

I think

the state lottery has
achieved that- Right

… over about, not yet.

I don't think the
state lottery's-

Yeah … achieved that yet.

I mean, unbelievable, man.

And all they

do is mint millionaires.

That's their job.

Right, right.

Not to mention kinda
innovating around electric

cars, getting us on a path
to Mars, like, like all this

other crazy shit, right?

Yeah.

Like, if he had done any one
of those things, he would've

been more than, you know,
uh, deserving of his- Yeah

asymmetric reward.

But dude did all of them.

All of

them.

And again, this
isn't fanboying him.

I, he, actually I think
he's kind of a weird dude.

Yeah.

So I'm not like in l-
love with Musk, but I'm

saying, as a founder-

Yeah


knowing what it took
to get there- To

get there


I'm like, he deserve- Here's
another good example Whenever

I see professional athletes
at the top of their game-

Yeah,

yeah

right?

People are like, "Oh, they
don't deserve to get paid

that much money." Right.

Okay.

Try doing what they do.

Yeah,

yeah.

Right?

Go

ahead.

Aside from having to,

like- Make, make one of
those plays and survive it.

Yeah, right, right.

And it's like when you see
someone… A World Cup's

going on right now, right?

And, uh, you know, I
know you're a huge soccer

fan, or football is.

Oh, yes.

And, and you see the
people that- Yeah.

In fact, could you

talk a little faster, Will?

There's some games on right now.

When you see the people
that are in the stadium-

Yeah


at that moment, what it took for
them to get there- Yeah … the

sacrifice, the discipline,
like you had to be the best

of the best of the best.

And you're just talking

about the people that
bought the tickets, right?

Yeah.

Yeah.

Even that was a level.

But seriously, like what
it takes to get to that

level is so extraordinary.

Yeah,

yeah.

And when we talk about athletes,
I think people do a thing

where like, "Yeah, well, they
were just gifted athletes."

Nope.

Nope.

No.

Bullshit.

No.

Yes, they were gifted-
Yes … but they had to do

the work every single day.

And they worked their

gifted ass off every
day, night and day.

Exactly.

Morning and night, two-a-day
practices, three-a-day

practices, all the things that
nobody else was willing to do.

Yep.

Even people who
were equally gifted.

Yep.

Right?

And that- Um- … that is
what separates the people

who were gifted, aren't
gifted, the, all the ones who

are gifted to the ones that
actually make it up there.

'Cause some people will
rightfully say, "Well,

there were a lot of
people who were gifted.

You know, I saw, you know,
same level of talent when

we were in high school.

I, I, I played with that guy
and you know, we had another

guy who was just as good." Yeah.

Did he do all the
things that guy did?

No.

Okay.

There's the difference.

Right.

And- I wanna circle back on
something else 'cause just the,

the whole- Yeah … like the
whole on the backs of, right?

Because people look at, at
an outcome like, like Musk

just got, and it is, like
it is the biggest asymmetry

we've seen yet, right?

Yeah.

Who knows what's next, but
he's a trillionaire now, on

the backs of people, right?

And, and you said something
the other day that like

is worth repeating.

Those were not exactly
like shitty jobs that those

people had- Right … during
that time while they were-

They're the highest paid
people in the country

while he was- Yeah … while
he was climbing up their

shoulders to get to the
top of his pyramid, right?

Yeah.

Those were some of
the most sought after,

well-paid, highest benefits.

Forget about the fact that
they got an asymmetric

outcome after the fact, right?

Yeah.

They became millionaires
on the day that their

stock options became
worth a shitload of money.

Right.

They were paid pretty damn
well the entire time, or

actually- Yeah … very well
in most cases the entire time.

So like, come on.

Like what you're really saying
is, "I don't have that money,

and I would like that money,
but I'm not willing to do what

they did to get it." Right.

So meh.

Yeah.

Come on.

Yeah.

Well, and, and I get it, right?

It, as much as I don't, I don't
agree with it, I get it, right?

Like you see someone that has
something that you don't have,

there's no way for you to really
ascribe the actual work, uh-

Yeah … risk and everything
else that it comes with it.

I get that.

But again, I think there's
a reason- Why you don't

hear that commentary from
other people who do that-

Yeah

like in other words, i- if you
were a professional athlete that

didn't make it to the World Cup
level, but, but you had tried

out for the team and you're the
last person to get cut, maybe

you're like, "Ah, well, I was
just as good as, you know, the

other guy that, that's on the
field." I would say probably.

You know, I mean, there's,
it could be a coin toss

when one of you had a better
practice than another.

Yeah, that kind of thing.

But there's no way that
person would say, "But I

don't think those people
deserve to be there at all."

Yeah.

Right?

Like, like in other words,
they know exactly how

hard it was to get there.

Yeah.

So there's no version once
you understand the journey

that you can't appreciate it.

Right.

It'd be the equivalent of me
saying, "Having a baby means

nothing. What is it? Like eight
hours of hardship to have a

baby?" Yeah, dude, try doing it.

I'm gonna go ahead and
assume Sara's not within

earshot because nothing
hit you in the back of

the head right now, Will.

Yeah.

Yeah, yeah.

But what, no, that's
respect though.

I'm saying like I can't
possibly appreciate-

I know


what that was because I
wasn't willing to do it and,

and physically could not.

But like until you've gone
through it, you really

can't comment on it.

Yeah.

Right?

But again, I don't think it's
incidental that the people

that have gone through it
don't comment on it, right?

Yeah.

Because we're like, "Holy
Jesus." Like, I don't bemoan

Musk for becoming a trillionaire
because I'm like, you don't,

hard that is to do that.

Yeah.

Right?

Like to pull that off.

I'm more, I admire the
accomplishment even if I'm

not like in love with the guy.

Right.

'Cause I'm like, "Damn."
I look at it the same

way with athletes.

Like there's certain athletes
that I'm not like a fan of

the athlete- Yeah … but
I'm a fan of the game.

Like watching their jump
shot or their fastball

or whatever, right?

Yeah.

Yeah, right?

Like I'm, I'm not
a huge LeBron fan.

I'm not anti-LeBron, right?

I, you know, he's got kind
of a huge ego, but I'm

like, "But there's only
one of them," you know?

Yeah.

Right, right now.

You know?

Yeah.

And what it would take to get
there and manage that and show

up, he's 42 years old, you
know, and be able to do that

over and over and over- Yeah
… through injuries, et cetera.

I'm like, damn, if you
can be that good and

withstand all of that-

Yep


you deserve whatever you get.

Let's spend a second
unwinding what I think is a

misconception about all of this.

We talked a lot about the
sacrifice, but I don't think any

of us do this- Yeah … because
we enjoy the sacrifice, right?

Yeah, right.

Yeah.

I mean, maybe Mascis
out there, sure.

But I don't think the vast
majority of us are doing

this to collect pain for fun.

No.

We do it because we wanna
control our outcomes, right?

Right.

And yes, we might be chasing an
asymmetric reward, but I think

that people get the reward wrong
too from the outside, right?

They'll assume that it was the
nicer house, the private jet,

the big financial outcome.

Yeah.

Yeah, yeah.

And sure, like, you know,
nothing wrong with the toys.

But especially along the
way, it's not the thing

that's driving the sacrifice
because none of that

comes until later, right?

The real asymmetric reward
that's there throughout is

ownership of the outcome.

Mm-hmm.

And I think the, the, the fact
that- Right … in generally

speaking, we answer to no one,
which means we also answer to

everyone, but we build what
we want, when we want- Yep

how we want, and I think
that's the thing that

we've been willing to
sacrifice- All along, right?

Yep.

It's sacrificed for
all along, right?

Right.

The control of our own
life is a reward worth

sacrificing your life for.

It's the way you send
soldiers into combat.

Yep.

Right?

Make it something
bigger than themselves.

You make it something kind of
biblical in nature- Yeah … as

to, as far as, you know, what
the outcome's going to be.

Control of your own
destiny has no price tag.

Yep.

Right?

Like, I've always said this.

I've been very adamant about it.

I said, "If I could make a 10th
of what I make…" If you said,

"Hey, you got two choices.

You make a 10th of what
you make, or you make

exactly what you have now
or even more, but you have

to go report into a job."

Yeah.

I'm like, "Give me a 10th
of what I make every time."

Now- Yeah … I also say
that 'cause I believe I'll be

able to, to make up for it.

Right.

But the thing I value
the most is autonomy.

I haven't had a boss in 32
years, pretty much my, you know,

my entire career, and I've had
plenty of years where I had no

idea if I was going to get paid.

So, like, the, the financial
reward wasn't the effort.

But I always knew that
it was, it was under my

control, so to speak.

Right.

And I think for a lot
of founders, that's what

they go into this for.

Like- Yeah … no one's
guaranteeing those outcomes.

Yep.

And if I'm being honest, having
talked to a lot of founders,

I'm curious your thought.

I don't think a lot of them
are like, "I'm doing this

specifically 'cause I wanna make
so much money." I think they're

doing it for a different reason,
and it happens to make money.

Yeah.

Right?

I'm not saying they're
altruistic, I'm saying

that's- No … usually
not the primary driver.

Look, I agree with that.

And, and I think that for a
very, very long time, starting

your business, like if we
go back to, like, slightly

before the startup period as
we know it now- Yeah … there

weren't these crazy massive
outcomes, and yet people have

been starting businesses- Not
a sure thing from the time-

from time immemorial, right?

Yeah, yeah.

Like, people have been doing
things to, to make money.

And so yeah, I think that, that,
that isn't the thing, right?

The reward isn't the jet, right?

It's that nobody
gets to tell you no.

The jet is just what everybody
sees from the outside, right?

Yep.

But that ability
to pick the path.

So Elon might go, "Yeah,
being a trillionaire, like

yeah, I did that." He's like,
"But you know what was really

driving me the entire time?

Like, I couldn't find a job
where I could say, 'And what

I wanna do is eventually go to
Mars and colonize it,' where

people wouldn't- Yeah, right,
right … just laugh me out of

the fucking room- Right, right

and tell me." Like, just like
there isn't a job that exists

where you get to say, "I'd like
to sign up for the part where

we're gonna go to Mars." Like,
it doesn't exist unless that

guy makes that a real thing.

Yeah.

That's the value for
somebody like that.

Right.

That's the value for founders,
that we get to go, "I have

this crazy-ass thing I wanna
do, and I wanna do it my

way, and I'm gonna go do it."

And this is the only place and
the only way that can possibly

manifest and maybe become true.

I agree.

And, and I think that everyone
goes into this with this idea

that, hey, I don't think I
wanna sacrifice that much.

I don't think- Yeah … anybody
signs up for this job with

any idea of what's actually
going to happen, like how

brutal it's going to be.

And it's gonna be brutal.

And so if I map back to that
conversation, 6:00 AM with

aspiring founder, and, uh,
it's 15 degrees outside,

and I'm explaining all this.

And, you know, old man
Schroeder, and he thinks

about it, and I'm, and I
come ask him, like, "Hey,

do you, um, you know, would
you be willing to go through

everything I just described?"

Yeah.

And he thinks about it,
and he says no, right?

Now, to be honest, wasn't
the answer I was expecting.

No.

I was kinda hoping for like,
like a more ambitious answer.

Yeah.

But when I thought about
it, I was like, that's

a very honest answer.

Yeah.

Okay?

Now, what he's saying
is, "That sucks. Like, I

do not want to do that."

Right?

Yeah.

Which, again, is a
very reasonable answer.

But then I thought about it.

I'm like, you know what?

That's what everybody
thinks going into it.

Everyone thinks they're
gonna get that outcome,

but not have to go through
that gauntlet, right?

Like, I'll be the smart- Yeah
… person that doesn't have any

of the hardship or any of the
bullshit, but somehow gets to

the finish line all the same.

We all go into it, and I think
it's the only reason you go into

it Yeah … because you think
you can avoid getting shot.

And yet in the end, we all come
out as Swiss cheese, getting

shot a, a million times.

And so I told him, I was like,
"Listen, man, that mindset

is how we all start. We all
start thinking we're gonna

a- avoid this gauntlet."

We all come out of it
battered and bruised.

Now, some of us come
out of it battered,

bruised, and successful
in some respect, right?

Yeah.

Very few of us do.

I mean, there's, there's far
more casualties than successes.

Yep.

I said, "But that's the
value in this process.

You don't know, but if
you do, the reward can

be significant, right?

And, and that's worth doing."
And so, you know, a month

later, uh, this is after we're
working on stuff, we help him

found his first company, right?

Yep.

Now, here's why I thought
that was interesting.

It's like I told him how
awful this was going to be-

Yeah … in no uncertain terms,
and he was willing to do it

anyway, which, which, you
know, you and I have a huge,

a warm place in our heart for.

It's kind of what we do-
Yes … all day long.

But I think for a lot of people,
watching them go through this,

this process, which you and I
do on a regular basis, right?

Watching them go through
this process, watching them

go through this gauntlet.

Years later, we're gonna
come out on the other side

and I'm gonna be helping him
build his dream house, right?

And I'm gonna say to him,
"Was it worth it?" Yeah.

And he's gonna look around,
and he's gonna, he's gonna

look at, you know, what he's
built, he's gonna look back

on his career and everything
it took to get there, and

he's gonna say, "Fuck yeah."

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