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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 Will Schroeder,
my friend, the founder
and CEO of Startups.com.
Will, as founders, do we really
retire, or do we just stop
one company long enough to
start lying to ourselves about
not starting the next one?
Where the fantasy is that after
this exit we'll finally sit
on a beach and relax forever,
but what we usually wanted
wasn't retirement, right?
We wanted relief.
So Will, why do founders
keep mistaking- I need a
break for I'm done building.
The fundamentals of
being a founder is
that you're a builder.
You want- Yeah
to build stuff.
Like that's, that's
how you got here.
That's problem solvers, right?
Right, yeah.
It's like saying an, a
artist saying, "I wanna
retire from art." Uh-huh.
No, you're still an artist.
Like you still create.
Yes.
Yep.
You wanna retire from
the bullshit that comes
with the job, right?
Yeah.
But that doesn't mean you
don't like the work, right?
'Cause that, that's
very different.
Now, I'll give you
a different example.
Like, uh, growing up, my, my dad
was a carpenter, and we'd go on
the job site together, and I'll
never forget sitting there on
one of the job sites toward the
end of the day, and I'm like,
"Dad, isn't this awesome?" Like,
I was like, you know, 14, 15.
And I was, "Dad, isn't this
awesome? Like, we built
something that's never existed
before," and I'm, like, creating
this whole narrative about it.
And my dad looks at me, right?
And he's like, "No,
it's not." He's like-
No … "I'm 40 years old.
My back is shot-" Yeah … "my
knees are shot." He's like,
"We'll do anything but
this," which of course is
the first thing I did as
soon as I had an opportunity.
But, like, what he was
saying is, like, "This
job is painful," right?
Mm-hmm.
"I don't want to do it." Yeah.
And he's right.
That is a painful job.
You would want to stop doing
it as soon as humanly possible.
What makes our pain different?
'Cause I would argue a
founder's, uh, y- I m- we
don't end up with bad backs
and bad knees most of the time.
We, we can, because we get into
all kinds of other nonsense.
But- Mm-hmm … like, what
makes our pain different, right?
Like, why is it that we're
addicted to the pain?
I would say that the pain isn't
any different, it's the why we
were doing it that's different.
Ah.
See, my dad didn't give a shit
about being a carpenter, right?
Yeah.
Like, all he cared
about was- Means
to an end.
Yeah, yeah.
I, I can swing a hammer,
I jump in my van,
somebody pays me, right?
Like, that's pretty
much it, right?
But that's not why we do
what we do, which is why we
do it for free for so long.
Yeah.
Right?
You know, we do it with,
with a expected future
payment that rarely comes.
Yep.
But we do do that.
You hear never of carpenter
that's like, "Man, I spent,
like, you know, four, five
years working on this house,
and you know, I didn't think
I'd ever get paid for it, and
lo and behold, I didn't," right?
"But I loved it so much." Yeah.
"I just care about
building so mu-" You
literally never hear that.
We are, we have a calling.
Like, we fundamentally, you
know, as, as founders, have a
calling to want to go build,
and it is antithetical to
what we're born to do, like,
what our DNA is, to say, "I
want to stop doing it," right?
Yeah.
And so when we think about
retirement, which is quite
literally the cessation
of doing, you know, what
we're used to doing, we
think about it like, "Oh my
God, when I get to retire,
things are gonna be great."
And I'm like, not really.
No.
Not-
Not unless the world has also
run out of problems, right?
Because as you said-
Yeah … man, a, a normal
person retires to stop working.
Yeah.
I know what retirement
looks like for me.
I can already see it,
because it happens in these
little brief moments now.
I didn't have to fully retire.
Today I went downtown.
I had to go to the dentist, and
then I met my wife for lunch.
Uh-huh.
And but as I was sitting
at the dentist before,
uh, she had gone… We
both had appointments.
This is like, this is
what you do now as,
as couples of our age.
We go to the dentist together.
So I'm sitting there, and
I've got a few minutes to
just, my brain just goes
where it wants to go.
And I'm thinking, I'm watching
my wife pour a glass of water,
and I'm thinking, "Man, water's
gonna be one of those resources
we really have to be careful
of in the future." The next
thing that happens is I get
an alert on my phone from
Perplexity, and I go, and this
is a big part of it, right?
AI is sucking up a ton of
water to cool data centers.
Uh-huh.
Where does my brain go next?
"Hmm, I wonder if the thermal
exchange between data centers
and water treatment could be
combined. Could we start putting
water treatment facilities
around data centers- Right
… and not just make the process
more efficient, but g-," right?
Th- this is what
happens to a founder.
I was left- That's how
we're built … I was
left with four minutes.
Four minutes.
This is how we're built.
This is how… And, and, and
that's the point of this, right?
So-
That's retirement.
And you know, Ryan, it's, it's
funny because as we g- continue
to get not younger, this-
Yes
…
conversation starts to become
more and more popular, uh- Yeah
both with ourselves,
uh, with our peers.
And I-
Now, I might not think
I'm getting closer to
retirement, but my hairline
might disagree, right?
It's like, it's already, my hair
started retiring five years ago.
Yeah.
It's just waiting
for me to catch up.
You, you… it's the
canary in the coal mine.
I think about it like this.
I think that there, there
is a, a very misplaced dream
about what retirement means
specifically- Yeah, 100%
… for founders, specifically
for founders, right?
And I thought today we
could kind of unpack why
that dream is so broken.
And, and by broken, I
simply mean that what
we think retirement can
or should be is a myth.
It's not that we can't- Yeah
… do it, it's that what we think
it'll- We don't … w- we'll
be for, it backfires in a huge
way- Yeah … every time, right?
Like, every time.
Yeah.
And I think it starts- I think
it starts with the dream.
Ryan, w- when you think about
the dream of retirement for a
founder, we're generalizing,
how do you envision
it?
I don't anymore, because we've
done this podcast, uh, on,
on like what retire- the fact
that you and I have both sort
of play tested this, right?
Like- Mm-hmm … we both
went and did some of the
things that we thought we'd
wanna spend our time doing
if we just had lots of time.
Turns out I didn't wanna do
any of those things full-time.
Mm-hmm.
Turned out that the way I
was already doing them as my
part-time hobbies was absolutely
enough of those things.
Yeah, yeah,
yeah.
And so we figured out, like,
oh, founders don't retire.
We reload and then we
re-tire, meaning a re
dash, hyphen tire, right?
Yeah.
We tire ourselves again.
So we, we get tired- Yeah, yep
so we retire, and then we
reload, and then we re-tire.
Like, this is what we do.
Because the, the exit doesn't
kill the builder in us.
Right.
It just clears the calendar,
and what do you do with
an empty calendar, Will?
Add more stuff.
I fill mine as fast as I can.
Yeah, yeah.
Right?
I don't wanna stop
building.
B- bigger task list.
But Ryan, I, I think that for
almost any founder, there's
this dream of retirement, in
some cases a fear of retirement.
Sure.
That, that, that would be mine.
And the dream is I can finally
do the things that I wanna
do without my startup being
in the way or, or, or my
founder job being in the way.
Yeah.
And my argument is,
I don't think that's
actually what you mean.
No.
What, what they mean is, I want
a version of my future that
doesn't involve the pain that
comes with being a founder.
Yes.
The general, like the
prototypical retirement,
right, is that we all
go to the beach, right?
Yeah, right, right.
Let's just use that for a second
'cause it's, it's a funny- Yeah
… it is a funny metaphor here.
So the beach sounds amazing
when you're drowning, right?
When you are just overwhelmed
by your business, when
you're drowning, the beach-
Oh, I feel like- … is
the best place … you're
in the, in the
ocean on the beach.
I was like, I guess.
Yeah, yeah.
You're, you're coming from
the ocean to the beach, right?
Yeah, okay.
It sounds amazing, and it is.
The beach is the most
amazing thing when
you're actually drowning.
But after you've rolled up on
shore for a bit, you've hacked
out the water, and you've, you
got a little bit of sunburn,
it gets really boring once
you can breathe again, and
that's the problem, right?
Yeah.
Like, it's the overwhelm
we're trying to escape,
not the actual work.
It's the way the work is
happening that we're- Yeah
… trying to get away from.
And so, yes, I think every
founder should have a dream for
what a sustainable and healthy
and happy version of running
their company looks like.
To me, that's probably the
closest we get to retirement.
But I think that, that
dream, if misplaced, if
misunderstood, is a- Yes
huge problem.
I think if we're thinking,
"I have to retire," ergo stop
doing what I'm doing, sell my
company, whatever, in order
to like kinda get this sense
of relief that people usually
get with retirement, I think
that's a dangerous proxy.
I think it's a dangerous proxy,
number one, because it implies
that you're gonna stop doing
What you were meant to do.
Yeah.
Now, now let me, let, let me
zoom out a little bit, 'cause
I, I wanna make sure that this
doesn't get misunderstood.
If you're working 60 hours
a week and banging your head
against the wall, and you're
worried about payroll and
everything else like that,
no sane person would say
you should do that forever.
This is not what we're saying.
Correct.
Right?
What we're saying is the
thing inside you, of all
of us, that wants to build
should never be contained.
Should never-
Correct … be contained.
And I think that's where we
think of retirement as this
idea of putting to pasture
what it is about us, and
I don't think putting that
creativity, that productivity,
that brain that wonders
how you're, h- how you're
gonna cool off data centers,
should ever be put to rest.
If anything- Yeah … I think
it should be cultivated for
as long as it possibly can.
Stay in motion.
I mean, it's… That was
one of my, my grandmother,
who's now 101 years old,
that was her advice.
Like, find something that,
that you can do, that makes
you happy, that you can keep
doing for as long as possible,
and just never stop doing that
thing, and that's the secret
to a long and happy life.
And like, gonna have to kind
of trust her on this one,
'cause she's, she's, she's got
the math to prove it, right?
Just for fun, I pulled up
our retirement plans, and
it turns out each and every
one of them, b- uh, uh, of
our retirement plans, Will,
has a 90-day vesting cliff
before the next idea shows up.
That's pretty tri- Actually,
let's stick with that for a
second, because for a lot of
founders, they get a version
of retirement on an exit.
Yeah.
And it goes the same
way every single time.
Yep.
Every time they're, they're
like, "Oh my God, I'm
so excited. I, you know,
I can finally relax,"
and, and that is true.
Yeah.
You had a ton of crazy shit
going on five minutes ago.
You don't have that
stuff going on right now.
Yep.
And you have cessation
of that pain.
Awesome.
Yes.
You deserve it, and I'm
so glad you have it.
But then what?
The first month is
margaritas, the second
month is domain names.
Yeah.
We know where it goes.
We know where it goes.
And it's like y- you get
into this thing where, again,
founders who have the exit
have the opportunity to see
what it's like to not put
their trade in, in play.
And I think you find out
real, real quickly it sucks.
Yeah.
It sucks having this incredible
skill and not be able to use it.
Let me tell you where I've
seen this most painfully
and most consistently.
With athletes, right?
Nothing sucks more than
an athlete who can't
be on the field again.
Mm-hmm.
Right?
An athlete, like, like you and
I have some friends in common,
some, uh, coming out of the- Yep
NBA, et cetera.
Yep.
And their issue is they stood
in a stadium, right, of 20, 30,
50,000 screaming fans, right?
Yeah.
They hit the three, the
place went nuts, okay?
Hit a lot of threes.
Right, yeah, exactly.
We're talking about
the same
person.
Yeah, we are.
Uh, a- and, and then
they turn 34, right?
Yeah.
Imagine.
I, I, no, that's my point.
Ray Allen's
34, right?
The reason I'm bringing
up athletes is twofold.
Yeah.
One, because their cliff is
so early in life, which you
s- Yep … the back half of,
of that is, is very difficult.
And it's such a
specific calling, right?
And it's-
Correct.
Yeah.
And you can't
replicate it, right?
I mean, like- Correct … you
can Tom Brady it into your s-
senior years, but even- Yeah
then you can only
take it so far, right?
I say this because-
Unless you're Jack Nicklaus.
Apparently that guy can
play golf
forever.
Or Hulk Hogan.
Or Hulk Hogan, who can- Yeah.
Uh, yeah, yeah.
Who came back 6,000 times.
But, but I, I guess what
I'm saying is for these
folks they don't have the
ability to go back to doing
what they were doing, right?
You know, they go on to become
ESPN commentator or something
like that- Yep … which
is like a fraction of what
they were doing before.
But for founders, we can
Warren Buffett that shit.
We can do it forever.
We can go.
We can go forever.
Right?
I just talked to a founder,
a friend of mine who's now
64, and he's like, he had
put on his LinkedIn retired.
And I reached out and I
said, "Stealth mode?" And
his response was, "Fuck, you
caught me." It's like, you're
like, "Ah, you're not retired.
Like, what are you
talking about?"
Yep.
Uh, so but this is
the way it goes.
It is.
And, and so when we talk
about, when we talk to,
to founders who said, "H-
hey, I'm gonna retire," we
always say the same thing.
"Let me know when you're done."
Let me know when you're done.
Yeah.
Right?
Yeah.
Because you'll always be done.
Let me know when you
untire.
Yeah.
Yeah.
And so, like, it's
like this for me.
Every single time I go on a
vacation, an actual vacation,
and Ryan, as you know, I suck
at vacations, so much so that
my family now leaves me behind.
They're just like, "You're
so bad at this, we don't even
want you to go anymore." We
don't even… Yeah.
They're awesome, but they
just know that the entire
time my head is elsewhere.
It shouldn't be.
Yeah.
But it is.
Yeah.
And so here's what happens.
Every single time I try
to s- set up a vacation,
I have the same game plan.
This is kinda funny.
I'm gonna overwhelm myself
with things to do, right?
Uh-huh.
Right, right there you can
already tell it's going
the wrong direction, right?
I'm gonna overwhelm myself with
tasks of things I have to do
that don't involve my job- Yeah
… in order to, like, force myself
to be having fun, I guess.
It has to feel like there's some
other meaningful outcome from
what you're doing, otherwise you
can't just go and do nothing.
Yeah.
If I'm not checking a box, I'm
really uncomfortable, right?
Yeah.
So I have to have read a book,
or I have to have listened to
a podcast, or I have to have,
like, done something, right?
Yeah.
I always have checklists
going into my vacations.
Yeah.
My checklists never
get checked off.
Whatever I said I was going to
do, I never ever, ever, ever
do it, because after I get to
maybe the second item, it's
the same routine every time.
I'm like, the more interesting
thing was the thing that
I, that I left behind.
Yeah.
It was… Yeah.
Right?
And so the last time, uh, we
got a place that we stay at in
Florida, and the last time I was
there, by the second day- I had
come up with some reason that
I had to figure something out.
My in-laws, you know,
had, had like their condo
in, uh, uh, in Florida,
and we leave stuff there.
Like, the kids leave, like,
toys and stuff they- Sure
wanna use.
Yep.
My wife leaves changes of
clothes and everything.
Do you know what I leave there?
One thing, a 34-inch
external monitor.
That's the only- Yeah,
yeah … thing that,
that, that I leave there.
Right?
I have the exact same setup
at my in-laws in Florida
with a gas pump arm.
Like, I've got
the whole, like…
You know, you've
seen me do this.
Yep.
I have a second podcast
set up down there.
Like- Yep … I've got,
I have my studio stuffed
in the top of a closet
down there for when we go.
And this is by no means
a recommendation or
endorsement to do any of this.
If you can go on a vacation,
enjoy a vacation, by all
means, enjoy a vacation, right?
So, and, and this isn't me
saying, "Yay, me. Look how good
a…" It's me coming to the
realization after a while that
the thing I love, the thing I
absolutely love, is creating.
I love to create.
Like, to me- Yeah … a
vacation would be me
creating nonstop, right?
Yeah.
So the idea of not doing that,
of saying, "No, you're gonna sit
by the beach and stare at the
ocean and sip a margarita," is-
Yeah
torture, right?
Like, that is-
Send me to the beach
…
worst
possible outcome.
I have- I'm, I'm
out in the water.
I'm like, "What kind of animals
can I catch? What can I dig
up at the bottom? How big of a
sandcastle can we make?" Like,
something has to be happening.
Tell me, man.
You brought up something
funny, which is it's like, you
know, you need the checklist.
You gotta feel like
you're doing something.
I have realized that
I've even started, 'cause
like you want there to
be a meaningful outcome.
Mm-hmm.
Over the last couple
weeks, sometimes I stack
these things, right?
So, like, because certain
things are meaningful for
different reasons, right?
So, like, I've, I've been, I've
been doing a lot of running in
the mornings lately, and that's
great, and that has an outcome.
Yeah.
But that wasn't enough for me.
So what have I started doing?
I have my, uh, Fireflies
app that I turn on.
I've got my headphones
on, and while I'm running
I- ideating blog posts.
I'm thinking about
marketing funnels.
I'm, I'm talking.
I'm basically brainstorming
while I'm running.
And to make it even more
pathological, now I've started
conducting founder calls, and
I'm doing, like, one-on-ones
with people while I'm running.
So I'm giving advice while,
like, panting- Right?
… into their ears the
entire time as well.
It's fantastic, right?
Wow.
I would like that so much.
Because why not check
two boxes if I can?
It's pathological.
Here's what I would say, though.
It's because there's
no substitute for
what we do, right?
Yeah.
And w- when I say that, I
mean the world of creation.
There is no substitute
for creating.
For creators, there
is no substitute.
For everyone else, like, my
wife couldn't give a shit less
about a- any of this, right?
Like- Yep … she's like,
"I'm gonna- I'm going by
the pool. You know, give
me a margarita," right?
Like, she's, like, totally good.
Yeah.
Can take both.
Right.
Exactly, right?
But for me, and I think, you
know, for founders in general,
we have this gear that, th- this
calling, you know, that I don't
feel like we appreciate, right?
I think for a lot of folks,
they don't realize that,
like, again, what we do was
never really about the job.
The, the job was- Yeah
… work, et cetera, but it
was about mission, right?
Yeah.
It was about mission.
Startups, th- they're not a job.
They're a mission.
It's a problem we've
set out to solve.
Right.
My dad working on the job
site was not on a mission.
He was on a mission to go home.
No.
Yeah, yeah.
He was like, "I gotta, I gotta
get, stop doing this," right?
How quickly can we finish
this, get paid the same amount,
and watch the Braves play
or whatever it is, right?
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.
There is nothing more exciting,
more fulfilling than when- Yeah
we are on mission, right?
When we are challenged, when
we are creating, when our,
our minds are exploding,
even though it has so many
negative consequences along
the way, economically,
emotionally, physically,
you know, you, you name it.
Yep.
Right?
They're all there.
And all those costs are real.
But let's go back
to you running.
I would equate it
to a triathlete.
What a triathlete has to
do for like an Ironman, to
prepare for an Ironman, is
grueling at best- Mm … and
punishing at every level.
But the idea is they're on a
mission, and that mission is to
complete this objective, right?
Yep.
And when they do, the
feeling you get from
crossing that finish line-
Yeah
right?
Pure euphoria.
There's nothing else like it.
I think what happens is, this
is the folly, I think what
happens is we believe that we
can get that same outcome, that
same feeling, without training,
without running the triathlon.
Yeah.
Right?
Yeah.
They're like, "Oh, well, I
don't wanna do all the running,
but I want the part where
I cross the finish line."
Yeah, the finish
line looks cool.
Yeah.
How do I… Can I
just start near that?
Just
one of those instead.
Let me start there.
And I think that's
what we misunderstand.
Like, all of this hardship, and,
and there's lot… Of course
you want less of it, okay?
Uh, again- Yeah … there's
no argument there.
But the idea that, that you
wanna make it all go away,
you wanna take the hardship
away, also means you're
gonna take the upside away.
Yeah.
And the upside ain't small.
And I don't mean financially.
Yeah.
I mean m- maybe, maybe
if things go well.
The excitement- Yeah … of
running the race, of crossing
the finish line, man, there
is no substitute for that.
Yeah.
I think we start to dream
about retirement when what
we really need is just,
it's recovery, right?
Yeah.
To me- Oh, 100% recovery.
Yeah.
No doubt … this, this desire
to never work again is the
incorrect framing, right?
It's a signal that the
current way of working
has become unsustainable.
Yeah.
Of course it is.
Right?
And so relief- This is
a hard job, man … from
stress feels like freedom.
Yeah.
And it is, but it lacks
fulfillment, and I think
that's really the problem.
That's what draws us back in.
So this fantasy of retirement,
generally speaking, forms
at the lowest energy point,
which also makes it a really
bad life design blueprint.
Like, you don't wanna be sitting
down and doing that, right?
Retirement for founders
is just like, it's burnout
wearing a Hawaiian shirt
on a beach with a Mai Tai.
Like, what they, they don't mean
that they, they wanna retire.
They mean that they want
the pain to stop, right?
You said this before, Mitch.
The, the, the pain-
Yeah … needs to stop.
The, the dream isn't no work.
The dream's probably something
like no panic, no pain, no fear.
Right.
The relief isn't your calling.
It's not a switch.
It's not like, "Oh, now
I've earned relief. It's
now my new calling." No,
that's the pressure valve.
Yep.
Right?
And we definitely don't
want to design our entire
future, uh, from our,
our most exhausted self.
'Cause well, how often have we
seen this, this play out, right?
Like, founder sells,
disappears for a few months,
kind of plays golf, sleeps,
finally breathes, whatever.
Yeah, recovers.
Right.
Around month three they
start saying stuff like,
"I'm not starting a company,
but I've been thinking
about this market," right?
Yep.
It's a… And to me, look,
that's not retirement failing.
That's your nervous system
coming back online and
you finally being back in
the, like, I can build.
Yeah.
And so rather than have
to think that you have to
completely extricate yourself
from the first business
and kill it or sell it or
whatever, that you can do that.
Like, I, I think the, the
idea is that we have to
recalibrate how we're running
what we're doing now and
make it sustainable, right?
Right.
So I, I think we really have
to separate recovery plan
from retirement plan here.
I agree, and, and I think that
w- we can't deny that what
we do is a calling, right?
Like- Oh, it- … we do what
we do because we're- Some
people are and some
people are not, right?
Like it's- Yeah … it's
pretty clear.
We do what we do 'cause we're
fucking good at it, and the
idea of saying let's find a
way to take that away from
ourselves is pure folly.
I just- Yeah … I, I, I don't
believe there's a world where
the person who is, is absolutely
stellar at building- has said,
"I was so good at that, that
was my calling, but now I golf
and that is so much better."
Yeah.
And, and look, and maybe
you love golf so much-
That's a substantive-
… that that's true.
I hate golf, so a- again,
this, it's probably
not a fair analogy.
However, however- I
like driving the cart.
Does that count?
Yeah.
I like drinking on the cart.
It's fun.
I don't care if
it's going anywhere.
You drink, I'll drive.
How about that?
Yeah.
Perfect.
The way I look at it is for
folks that were built to
do this, I say this all the
time- Yeah … if you were the
kind of person that was built
to be able to retire young,
then the last thing you're
built for is retiring young.
No.
Right?
Climb a ladder and jump off it.
Yeah.
Like, that's, that's how you do
that.
I'm just saying, like- Yeah
… if you're the kind of person
that had the capability and the
drive and ambition to be able
to retire at 37 years old, just,
you know, as an example, then
you're- Yeah … not the kind of
person that was intended to be
sitting on a golf course- Right
or a country club for the rest
of your life at 37 years old.
Like, those two things are-
Well- … run polar opposite.
Yes and no, but play that out
for a second because I think
there are people who have set
that up as… Now I'm, I'm not
gonna say that they're correct
about what their dream is
because they probably haven't
played chess, they don't know.
But I think there are people
who are built to do that kind of
thing, where it's like, because
that was their motivation.
Maybe.
Their motivation was-
Yeah … go find path to
money, work hard, do these
things so I can retire, and
I think there are people
who aren't built that way.
I'd say that's, that's a
lot of corporate people
are built that way.
Yeah,
oh, that I agree.
Their motivation was that thing.
Yep.
I agree with that.
That wasn't our motivation.
That becomes our motivation
later when we're like,
"Holy shit, I'm tired. I'm
just, I'm really tired."
Is retirement less tiring?
Is it?
Why is it called retired?
Right?
Like, I don't wanna
be tired anymore.
I wanna be something else.
But I think we gotta be
really careful, right?
'Cause again, like, leisure will
remove some of the stress of the
business, but it doesn't replace
the meaning that it gave.
So I think that's
the difference.
That's… Yeah.
I think that's the difference,
because for us, the business
is the meaning, right?
Yeah.
It's the mission, it's the
purpose, it's all that stuff.
Whereas, so some other people,
the work was a means to an end.
Yep.
Like in your, in your father's
case, you know, the, the
houses weren't like, "Once I
build, I wanna build 300 homes
and know that I've put, you
know, families under root."
Like, that wasn't his thing.
He was like, "I want-" Yeah.
It's not a mission
"swing hammer, get
paid." Bed Be done Right.
That's it
Right.
That's it.
I think for creators, right?
Now, again, l- let's talk about
something slightly different.
I wanna cautiously use
this, this analogy.
Let's say you were a
stock trader, right?
Who, who are notorious for
making a voluminous amount of
money in a short period of time.
I am a stock trader of
the exact opposite sort.
I'm good at the
opposite, the opposite.
Yeah.
I can, I can lose
money really fast.
Right.
So, and let's say once
again, at 37 years old,
you've made enough money,
you never have to work again.
Yep.
And I would argue you're
coming from an industry that
is so cutthroat and so- Yeah
painful and so grueling that
th- you had every reason
to not wanna do it anymore.
I don't know that there
is such a thing as a
calling within that.
Well, okay, so, so
here's what I would say.
I wanna be careful 'cause, you
know, we're making- Yeah … a
lot of generalizations.
That to me is less about
mission and calling.
Mm-hmm.
And that's more about
just means to an end.
I-
in that case, the mission
is that is the means.
And I think there are times
where that absolutely is the
thing, but it's not for us.
I think for what we do as
founders and creators, I
don't think we have that gear.
I don't think it's
just a means to an end.
I think because of who we are
and, and how we operate as
builders, our mind constantly
wants that challenge.
Yeah.
I don't think we are satisfied.
I don't wanna use
happiness 'cause that's
an amorphous concept.
Yeah.
I don't think we are satisfied
unless we are latching onto that
type of challenge, and there
is no other challenge that most
people can find- That even pale,
anything pales in comparison
to starting a startup, right?
Yeah.
Which is why everybody
goes back to it.
Definitely.
Because we're like, damn, that
was the only game worth playing.
And it's funny too,
because it's not even just
the successful, right?
Like, how many third time failed
founders do we know who are
working on their fourth startup?
Oh, yeah, 100%.
Right?
It doesn't- It's not just
like, "Oh, that worked.
Let me do it again." It's
not even that, and I think
that's what points out that
it is a calling, and it
is a mission-based thing.
It's not just a means to an end.
Because if you failed three
times, clearly this doesn't
seem to be the means to an end.
Not that type of end, right?
Not a retirement, certainly.
And so I think that's where
we have to kind of figure
out, like, where are we at
in this whole thing, right?
Of course.
And of course, like, we get
closer to retirement, like,
we're not gonna miss the stress,
but damn, you're gonna miss the
voltage of being plugged into
one of these things, right?
Okay, so stick with that.
I've got a bunch of
friends that have retired
relatively young, right?
Okay.
30s and 40s, okay?
So they, they made just
enough money that they just
don't have to work anymore.
Uh-huh.
And some of them have gone
maybe 10 years since then,
and they haven't, you know,
started another company.
And th- these are lots and
lots of people that I'm kind
of parsing through my, my rol-
my mental Rolodex in this.
And here's what I would say.
For all of those folks,
some of them are satisfied,
which sounds wonderful.
They're not charged the
way they used to be.
Right.
Yeah.
Satisfied, like, "Man, I'm
glad I get up in the morning.
I don't have anybody bugging
me," you know, release the pain.
"I don't have any VC
that I gotta chase down.
I don't have, like…
You know, whatever.
Like, my satisfaction comes
from the lack of pain," right?
Yep.
Which I, I get, but
there's no charge anymore.
Yeah.
There's no, "I jump out
of bed, and I run to go
do this, 'cause I am so
goddamn fired up," right?
Yep.
It looks more like this.
"Man, it's great.
Man, I get up in the morning.
I get out of bed kind
of whenever I want.
I still get, you know,
keep a reasonable schedule.
Go work out in the morning, have
lunch with my spouse." You were
saying that's the thing, right?
Like, you know, have
lunch with my spouse.
Piddle around a little bit,
uh, contact a few buddies.
Sometimes I'll do g- golf
or I'll do this or that, and
I just kind of do whatever
I want whenever I want.
And again, that sounds
wildly satisfying, but it
sounds like zero charge.
The charge was when you were
so excited and on mission about
what you were doing, it didn't
occur to you what time it was.
Yeah.
It didn't occur to you how
much time had elapsed or
how much, like, pain you
had endured because you
were so fired up, right?
Yeah.
Like- We, we get to the point
where, like, the thing that
nearly killed us yesterday
before we went to bed is the
thing we wake up excited to
do the next morning, right?
Correct.
100%, man.
That's it.
That's how we're built.
Right, and so th- this
idea of retiring and not
doing that anymore, not
having that purpose, that
charge, to me is terrifying.
Oh, it is.
I- in very simple terms,
here's the transition that
you have to make in order
to go from one to the other.
You go from creation-
To consumption, right?
You go from making things
to- Yeah … just taking in
what's there and absorbing-
Yep … stuff, and it's, it's
not the same thing, right?
Uh, there's no real
substitute for creation,
and for me, consumption
gets boring really fast.
Like, just taking what other-
Yeah … people have done.
Like, at some point I'm
just like, "I wanna m-
me do it myself," right?
I started saying that when
I was two years old, and
I haven't stopped since.
And I gotta say, like,
when I think about where
I enjoy, you know, where,
where I enjoy my time.
So you know, obviously, you
know, throughout the coup- last
couple years we've been talking
about m- me building a house.
Last December, I took
December off to do
nothing but build house.
Now honestly, that gave me a lot
of vibes of working with my dad.
My back hurt.
Yep.
My knees hurt.
Yeah.
Like, this is a lot of work.
And I'm working 14 hours a
day and burning, like, 4,000
calories a day, and I'm
like, I am whipped, okay?
Now, that was a marathon
toward a very specific goal.
Yes.
However, however, I'd be lying
if, if I were to tell you that
there wasn't a part of me that
would take that over a vacation.
Hold on.
I watched you several times
take that over a vacation.
Yeah.
Well, my family was on vacation-
Like, like- … while I was
doing that, so I literally
took that … well, you
actually made that trade.
Yeah.
Yeah.
That's not, that's
not theoretical.
That, that happened.
I did.
I did.
And again, my wife and kids are
just awesome, so, like, they
understand, like, when Dad's
on mission, just let Dad be,
let Dad cook- Yeah … right?
Yeah.
Let, uh, let Dad do his thing.
But, but the other side of
it is not a single moment
had gone by, other than
wanting to spend time with my
family, where I was like- Yeah
I'd much rather be
on a beach right now.
Right?
I mean, think about that.
I'm taking my vacation time,
time I should be recharging with
and doing the opposite- Yeah
… you know, kind of running
myself harder, and I'm saying
what I want to do is create.
And to me, that's a vacation.
Now, now when I say that, I
don't expect everybody to feel
the same way, not even close.
But what I wanna point out is
I don't wanna be in a position
where I'm not creating.
Yeah.
Right?
Like, I'm not looking for
a future where I'm like,
"I'd really like to stop
doing what I'm good at."
Let me put it this way.
I'm 100% confident that if
the greatest of all time and
really any other player, you
know, whether it was, you
know, Michael Jordan, Tom
Brady, whatever, could play
to their 100 Warren Buffett
style, they'd absolutely- Yeah
be playing to the- to their 100.
Tom Brady actually tried it.
Yeah.
Getting closer.
But it's because that's what
we're built to do, dude, right?
Yeah.
Like, why would we
wanna stop doing it?
Why would we wanna
stop doing it?
I don't get it.
Yeah.
I think we can deny that builder
impulse for a little while,
especially when we're tired.
Yeah.
Yeah, yeah.
It becomes easier to do.
When we're
tired,
I get
that, right?
The, the thing is, once
that stress is gone, the
calling comes back, right?
That's what I was saying before.
It's like once, once the
nervous system resets,
we go, "Now what?" Right?
Yeah.
Like, how do I unretire?
And I think the, the
challenge I've seen for a
lot of founders is that…
A- and look, nothing
wrong with an exit.
Nothing wrong.
They're great.
Yeah.
Yeah.
But I've definitely seen
founders who exited and then
went on to try to find something
else as purposeful as the
business they were running,
but they were tired running.
Not tired of running.
Yeah.
Tired while running.
That's different.
Yeah, yeah, yeah.
Yep.
Very different.
And I think that in some of
those cases, they actually
would've been far better off
just to maintain the business.
They didn't need to sell it.
They just needed to change
their relationship with it in
some subtle ways that could've
made that easier to do.
It just, we just get
buried under exhaustion.
Let's build on that.
I think retirement, the, what,
how founders should think about
retirement isn't, "I want to
stop working." It's I want to
control the outcomes, right?
Yeah.
I wanna control maybe
I don't have any
investors anymore, right?
That seems to be, honestly- Yeah
… be the most popular one, right?
Anybody that's taken on
investors, that their dream
the next time is to not have
to take on investors, right?
Which is ironic- Yeah … 'cause
their dream the first time
was to, to get investors.
Yeah.
What, what can I do to get
an investor in the next time?
What can I do to avoid that-
Right … at all costs?
Maybe it's working with
fewer people or closer
people or both, right?
It's like, "Hey, you know, I,
I worked with a ton of people.
It was a lot of management
and p- and politics and
everything else like that.
I'd love to work with a smaller
team where it's very intimate
and, you know, we do our thing."
Maybe it's control of your day.
Like, "I liked what I did
as a founder, but the job
required 14 hours a day and,
and I, I don't wanna do that."
Well, guess what?
Yeah.
You don't have to
work 14 hours a day.
Right.
Your point of retirement is
to say- Yep … "I want to
work four hours," or whatever
your number is, right?
The point of retirement
should be a set of conditions
that allows me to do what
I love under my terms.
Yes.
Under my terms.
Yep.
That should be the framing
of retirement, and we should
be very deliberate about it.
It should be my dad saying,
again, this, he wouldn't
have said this, but my dad
saying, "Well, I love to
build stuff, but I wanna be
able to do it on my own time
without killing myself. You
know, if I'm- Yeah … if I'm
in pain or if I'm exhausted
the next day, I wanna be able
to not go to work," right?
Yeah.
That makes total sense.
I had a- Yep … a contractor
on my job last week.
He was 64 years old, and
he said, uh, this is why
my response will be funny.
He said, uh, "I can come
next week, but I can only
come for six hours," right?
Uh-huh.
And I was like, "Why?"
The gout, Will, the gout.
Yeah, yeah, exactly.
I was like, "How dare
you?" I just, it was such
a specific answer- Yeah
that I was just curious-
Yeah … why he said it.
He's like, "Well, I'm retired."
And I'm like, "But you're
still working, right?" He's
like, "No." He's like, "I
still work, but I work a
retirement schedule, not my
previous schedule." I love it.
And I was like, "Hats off
to you, brother," right?
Yeah.
Like, yes, that's
the answer, right?
Like-
Yeah
…
I'm working on my
own terms, right?
Like- That's it.
Look, we can't fight the
wiring, and I think it's,
we find ourselves apologiz-
apologizing for the wiring,
that we're built this way.
This is what we are.
We don't have to
apologize for the wiring.
We don't have to fully
change the wiring.
Just start designing
better circuits, right?
Right.
To your point, like, how can
you make this just work in a
way that works better for you?
There's plenty of
optimization to be had.
I don't think founders,
any of us, should be
thinking about how do I stop
doing what I'm great at?
Yeah.
I think we should reframe it
to say, how do I stop doing
what I'm g- or how do I keep
doing what I'm great at,
but stop doing what I hate?
Yeah.
Retirement should
be about reframing.
So I, I don't want us to
pretend like, like w- we
don't wanna build anymore.
I think that's bullshit.
This is what we are put on
Earth- Yeah … to do, right?
To like, we don't wanna- Yeah
… retire from that, right?
Retirement shouldn't be
about w- what I'm, I'm not
doing all those things.
It should be about this
is what I love to do.
I wanna do it forever.
Yeah.
But I wanna do it forever on my
own terms in a way that I love,
that when I jump out of bed
and I say, "I can't wait to do
this," nothing wears me down.
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