Welcome back to another 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 we get to this point where we cash in
life's chips and then we wonder, did we buy the right prize?
Right now, we've done this story before.
I'm gonna ask you to retell a story.
I want you to go back to the moment in time.
You and Sarah in Beverly Hills looking at Bel Air about to
buy a really expensive house.
Just walk us through again, 'cause we're gonna play around
with this in a different context today, around will
the payoffs be worth it?
We've talked about are the sacrifices worth it, but
will the sacrifice be worth the payout today is we're
gonna talk about, so I want you to take us back to that
moment where you're wrestling with the thought that like.
I did all this stuff to get to this moment so that I
could make this decision.
And then luckily, your, your, your wife stepped in.
Yeah, usually of all my life, my, my best of moments.
Uh, finish with, and then luckily my wife stepped in.
Uh, you know, it's funny, y yesterday I was at dinner with
one of our founder members from startups.com, uh, that
I met through startups.com, which is really cool, Uhhuh.
And we're at dinner and he hands me a t-shirt and, uh, it's a
t-shirt he had made for me.
And it says, well, this seems like a terrible idea.
What time?
Like that's, that's the tagline of my life.
Jesus.
Uh, yes.
That's fantastic.
Yeah, it was, it was a really cool gift and it's
so appropriate for this.
So we're going back a few years now, and right now
I'm thinking about that.
That was six years ago.
Like, yeah, I was thinking about this too.
' cause that until you said that, that felt
like very recent history.
But that was.
Six years ago,
so okay, we're, we're going back six years.
My family and I had just moved a few years prior
to that, to Los Angeles.
We ended up finding a house in Beverly Hills and everyone's
like, oh, that's so foo.
You know, bougie guys gonna Beverly Hills.
It was like our last choice.
It just happened to be where we found a house Uhhuh.
But anyway, so.
We lived there for a few years.
We quickly outgrew the house 'cause it was tiny.
And you know, my son Will had just been born and we
needed more room, so we go looking for another house.
Uh, my daughter had started school in Beverly Hills.
She, she loved it and we wanted to stay in that school district.
So we ended up finding a house that was like 10 minutes
away, which if you don't know your LA geography, uh,
Beverly Hills and Bel Air are just two tiny towns, more or
less adjacent to each other.
That's where we find a house.
And I say this and it's not like big time it being
Bel Air, literally, dude, that just happens to be
where we find a house.
Um, I wasn't trying to be the fresh Prince
of Bill there, right.
So, anyway, and I mean, maybe, yeah.
I mean, it wouldn't be the worst outcome.
We get to the, the finish line with this house.
We go through, you know, the negotiations and everything, and
it's, it's a big purchase right?
When we're on the goal line, Sarah and I had, uh, been
on a, a, a quick vacation, like a weekend vacation,
and, uh, we're sitting at dinner on vacation in Mexico.
Sarah's like, kind of sitting there going, you
know, this is probably a bad idea because as you know,
she's the conservative one.
She's, everything for her is, this is a bad idea and
everything for me is, this seems like a terrible idea.
What time?
Right?
What time?
I'm so ready.
I agree.
It's a bad idea, but we're gonna do it.
Yeah, exactly.
Yeah, that, that's literally my job description.
Here's what I told her.
I said I. If we balk on this, this is actually
a big problem for me.
And I said, you've gotta understand, like I've been
working my entire life sacrificing and risking nonstop.
I can't begin to tell you how many sacrifices
I made to get here.
And she's been through many of them, so she's aware.
Yeah,
like for the first six years of my career, I didn't see my
family or celebrate a holiday.
I never came home for Christmas.
I remember I went to other people's house for
Christmas because my family was too far away to make
the travel and I had to be able to come back in time.
And so those are pretty significant sacrifices
that you don't get back.
Yeah.
You and I, Ryan, you and I talked about it where like,
I don't remember college.
I
know I was there, but I just worked through college.
Yeah, I remember, I remember being in classrooms.
I remember being in big office buildings and, and,
and selling, uh, you know, enterprise level client stuff.
I don't remember, like, you know, I learned to play
beer pong when I was like.
30 in Cyprus,
like I I, I've never been little arrested development.
I've never hung out on the quad, so to speak.
Like I, college just happened to be an address that I
had while I was working.
Okay.
Yeah.
I'm, I'm nonstop sacrifice.
And then so many things that come with it, with building
your own company and the sacrifice, the things that
every single person listening to this inherently understands.
Okay.
So when you make all those sacrifices, we make them
with the expectation that there will be a payout.
Every time.
I feel like it's a little promise that you make to
yourself when you make that sacrifice that it's okay,
because I'll pay it back later.
It's okay, because I'll get more
later.
But we don't actually know if that's true.
We don't.
We treat, we treat sacrifice like it's a savings account.
Mm-hmm.
Right?
But we never check the balance or the terms.
Right?
Like, so when do I get to withdraw it?
N never.
Never.
Right?
It doesn't work that way.
Well stick with that.
Yeah.
There's no interest said this before in the podcast.
I must say it again.
There is no interest earned on happiness
deferred or life deferred.
It doesn't come back tenfold later just because you gave it
up now sometimes it does, right?
You might get a big pat at the end.
You might.
It's not like a guarantee.
There's, there's no just automatic
compounding in this one
isn't.
This episode isn't so much, I think about the sacrifice
as it is for the payout.
Let's assume the sacrifice was significant.
The question in this episode is, is there a payout that
could match the sacrifice?
Sure.
And, and I think there's an assumption that there is.
So here's what happened to me in this case.
So, uh, we're sitting there and my whole thing was like, look,
if I don't cash these chips in now, this was the moment, like
there was clearly, this was the moment where it was gonna be the
biggest purchase of our lives.
It was, you know, this, this beautiful house in, in Bel Air.
Like it was, it was exactly what you dream of being able to do
if you make those sacrifices, if you take those risks, right?
So this was clearly the moment to me.
It was something extraordinary that put the extraordinary
sacrifice into some level of balance to the extent, extent
that we can quantify either.
As soon as you said that, Ryan, I just thought
of something else.
It made me think about it.
I gotta say, up until that point, and not that
I never thought about it.
Oh, you know what, it's, I never quantified the sacrifice
before the quantification.
That's the, that's the challenge, right?
If I started just brainstorming and I were to say, here are
all the major things that I missed that I will never
get back my twenties, yep.
Et cetera, if I was gonna make that sacrifice, if I was
gonna make that investment.
This is the time to, to, to pay it out.
So then the question was, was it worth it?
Right.
And what, uh, Sarah ends up saying, she's like,
it's not, she's like, this is a huge rip off.
Right.
You know, relative to what we're paying and what we're getting.
It's ridiculous.
And I was like, yeah, but if, if I don't cash my chips in, like
this is a huge problem for me.
And she says to me, she says, you know what?
The whole point of that wasn't that you have to
cash your chips in now.
It's that you had chips to cash in at all.
Yeah.
So you don't have to cash them in now, find another
way to cash 'em in.
Yeah.
And based on that argument, we both agreed
right there, fuck it.
We're out and we moved back to Columbus a week later.
Yeah.
So I mean like as quickly as we tried to get into that
decision, we looked at it and we said, you know what?
Different direction.
And we
bailed and we moved back to Ohio.
Yeah.
And you know what?
Six years later, I have never heard you say not a single time.
A single thing about, oh, you know what?
I miss our ability to do this.
Or I miss when I, whatever.
Right.
Like, I miss running past all 12 of Channing Tatum's
abs, uh, on my morning jog.
Right.
Or whatever the hell it was.
Right.
Yeah.
I haven't heard you say it.
Not a once.
I
don't,
I'm sure my wife does, but I feel
very differently about his ads.
I heard he's down to a 10 pack now
that he's given.
Yeah, yeah.
Exactly.
But what, what was interesting for me.
I was forced to confront whether or not the sacrifice
that we all take on.
Yeah.
Aligned with a payout.
And I think what's interesting is, is that for many of us, the
sacrifice comes natural, but we don't really always know how
this payout's going to work.
Right, sure.
Right.
When you look back and you look, uh, actually, you
know, let me ask you this.
Recently, you just moved to Madrid.
You guys just went to Valencia as a family.
Was there a moment where you were like,
this is extraordinary?
It does.
Yeah.
Holy cow here.
Yeah.
And then we're here.
Then reflect on the sacrifice to get there.
Yes.
And you reflect on the sacrifice and you go.
This was worth it.
This feels in balance.
I think there's, there's something extremely important
in all of that, which is that like, I didn't buy Valencia,
I just experienced it.
Right, right.
Be because I think to some degree we do end up like
aligning because we don't, we don't define extraordinary well.
Like we had an extraordinary time in Valencia.
It was amazing.
A couple days at the beach, couple days at the museums.
Like really, really just had a great time, uh, with the family.
But we don't clearly define extraordinary in a lot of cases.
And then the default just becomes.
More and more is never enough.
And I think we get to this point where it's like,
you know, big purchase equals big purpose, right?
So this is, I have to do this in a, in a one-off.
I have to balance the scales.
Yeah.
The scales of sacrifice are completely tipped to the floor.
I've gotta, I gotta do something to balance this out.
I think that what I'm finding over time is that
instead of looking for that singular payout, I'm
treating it more like.
A line of equity, right?
Where I can just constantly make daily withdrawals and
just draw down and just enjoy and do the things.
And I get it though, like when you were sitting there
at that dinner in Mexico, thinking about the Bel Air
House, you weren't defending a decision around a house.
You were defending the meaning of 30 years of work.
Let's build on that.
'cause again, in this episode we're talking about the payout.
What if up until that point.
I had just assumed that was the payout.
You know, maybe, maybe my vision of it wasn't quite that crystal
clear that it was exactly the street in Bel Air, you know?
Sure thing.
But that was a, a very visceral like feeling to be
walking into this beautiful house in Bel Air and be able
to say, I can afford this.
I came from a place where there's no way I, I, I couldn't
have afforded to rent out the driveway and, and get to a
point where I'm like, okay, it's a lot of money, but I, but,
but I could make this happen.
But then part of me was like, okay, I made all those
sacrifices so I could be able to say that, but was this
really what I had in mind was this specifically it?
And it turned out, and again, this, this is,
we'll get to this later.
It wasn't it.
And that, that terrified me more.
Because for a while I was
like, well, what just happened?
I think part, part of the, what we, we end up going
through is that we look for these things that will be
obvious signals that, that there was a return, right?
That again, people have seen the sacrifices or maybe not,
but we've done the sacrifices and so we want the world
to know that it was worth it and so we did something.
And so I think oftentimes some of the decisions I've
become close to making or like things that would've been a
good signal to everybody else instead of what I wanted.
That it was really geared towards like this'll be a good
signal that I did well, right?
This big purchase will will signal that, yes, I did it
to everybody else, but then I looked at it and went like, but
do I actually care about that?
Do I actually want that?
And in your case, like, thank God you didn't buy that house.
Right?
It's interesting to me because we all put it
in the sacrifice, right?
Again, we all understand the sacrifice.
What we never can quantify is what's the rate of
pay for that sacrifice.
Sure, sure.
Now the, the rate of pay is directly proportionate
to what you think your payout's going to be.
Okay?
Yeah.
So in other words, if it's like I'm gonna sacrifice, you
know, a crazy amount of time, so I can buy a $10 million
house in Bel Air, then there's some rate of pay of sacrifice
that like that aligns there.
But if you have no idea what that outcome is, you
then also have no idea what your rate of pay is.
And I'm not saying it has to be that proportionate, but I'm
saying when you have no outcome.
You, you like, or it's just too amorphous.
Like you can't define the outcome.
You're like, I just want things to be better.
You're screwed.
Because then your rate of pay could be literally anything.
And the, the example I use is like, imagine you've
got your first job, right?
And you know, whatever your crappy first job is, your bag
groceries, your, you know, uh, mow mowing lawns, you know,
shoveling driveways, whatever.
And after your first two weeks, your boss comes to you and
says, thanks for everything.
Here's 28 cents.
You're like, what the hell?
I just worked nonstop.
I sweated like crazy for two weeks and that
was my rate of pay.
That's essentially what happens when you don't have a payout
that aligns with the sacrifice.
So I was gonna say like I think that's the, the challenge around
having those big goals, and I think the other thing that
ends up doing that is that we make the sacrifices across
such a long period of time.
Yeah.
And most of them are absolutely meaningful.
But they're very justifiable in a moment.
Yeah,
because that does get paid out, right?
That those are absolutely paid day by day, by
day, by day by day.
You don't write a big sacrifice, check at the beginning,
and then earn the payout.
You, you pay as you go consistently.
And again, when you don't have, when you got that, that
big blurry goal out there.
And like, let's, let's dig into this for a second.
'cause like, what's the most common, like vague or
blurry gold that, that you hear freedom, impact, time?
Like what are you hearing from other founders?
Well, okay, you know, it's funny you say, 'cause as
you were talking I was like, you, you were talking
about what your payout was, you know, throughout this.
And I was thinking your payout, you're being, a lot
of people's mind included, was the freedom to go to Valencia
was the, the freedom, all of which you've earned, right?
You know, which is the point of the sacrifice, the freedom
to, to do a job that you enjoy.
Versus having to take a job that you hate.
All of these things are incredible payouts.
They don't all involve a giant house, right.
Or a private jet, but they are incredible payouts.
Uh, peace of mind, pride of work.
I mean, there's, there's a really long list of somewhat
intangibles, but take them away.
There's no value to it.
Right?
In other words, it's so, so important For me, I always
used to say the same thing if you paid me 10 times more
than I make right now, but you say, the only caveat
is you now have a boss.
Not interested.
There's literally nothing I could buy.
Not 'cause I'm so wealthy, I'm not.
But there's nothing you could buy for 10 times more
for me that would outweigh having an answer to someone.
It's kind of just that simple.
I value that freedom as a tremendous part of the
sacrifice in the payout.
I think that once you understand how to use it,
it's one of those where I hear that and I do, I get it.
I totally understand it, but I think that there's, there's
a challenge around some of those as well, because when
the goal is amorphous, then again, like you don't know
what your rate to pay is.
Right.
If, if you're saying like, I'll get Yeah.
Paid.
We don't know how much or freedom of what sort.
Right.
And with what are the restrictions.
So I think it's just, it's super important to just have some kind
of a goal or, or, or maybe not.
Right.
And maybe, maybe that is the other side.
It's like, because I think if you had picked, because we
see that happen too, right.
And we've, we've done an entire episode on like play
testing some of your dreams.
Which you did in la, which I did in Florida.
And we, we, we come to find out like retirement's definitely not
what we're aiming for, right?
That isn't a goal that we actually wanted.
And so I think there's an interesting danger around,
like the clear definition of the goal can also lead to its
own level of disappointment.
Because if you thought the only thing you had in mind
was like, I need that house, and if I don't get that house,
then, then it doesn't work.
And then you get to that point and then you decide.
Actually, I don't want to need of that house.
Did you feel like you were in a vacuum at that point?
For a minute.
Huge.
Okay, so let's, let's
talk about that.
Yeah.
It fucked me up for a while.
I'll bet.
Because I didn't have, I remember.
Yeah, yeah, yeah, yeah, yeah.
I didn't have a, like, once you took that finish line
or that trophy or, you know, however ever you want to,
uh, attack it off the table.
I was like, I can't one up that.
In other words, if that's not what I'm looking for, then
what the hell just happen?
And I wasn't like, oh, that's cool, I'll just go on a cool
vacation and, and that'll be, you know, it was all worth it.
Damn.
It was the first time where I had to really second guess
whether this was all worth it.
When you don't have shit, you can always say, when
I get said stuff that I don't have, that it will fix
current problem, whatever your current problem is.
I mean, it is, it is the bane.
Of every, every marriage, it's, well when we just fix
this one thing, Uhhuh, right?
Usually it's money.
Then marriage will be great.
It almost never works,
right?
Had this conversation with the founder today, not
about marriage, but just about like the desire for
an exit and saying like, oh, well, once I don't have
the stress of this business, then life will be better.
I'm like, remember that?
Like you're creating a lot of this stress within the
business, and so if you think that you won't somehow find a
way to create similar stress in your regular life when you
no longer have the business probably misleading yourself.
You know, Ryan, as you know, like every year in December,
I take the month off.
And I usually go work more, but, uh,
I was gonna say, yeah, I think you take the month
off is probably not that you, you change to a more
rigorous type of work.
Yeah, I go work a harder job and so it usually involves
a lot of sawdust and uh, in sweat when I'm doing that job.
Right, and I'm, I'm building stuff and again, I'm,
I'm not working this job.
The startups.com job, within a couple days.
I think I've told you this before, like at first I'm so
excited to be able to do that.
'cause it's my passion.
I, you know, I love building things, but after a few days
I'm like, dude, this is really hard work and I'm not against
hard work, but I'm like, but if I had to do this for the rest of
my life, this would not be fun.
This would not be fun.
And so usually by the time that month elapses, which is
my version of a vacation, um, I can't wait to get back to
startups.com and I have so much more appreciation in my job.
But, but, but I say that to say it helps me quantify the
value of this job, the value of this sacrifice, because
I, I, I get to step away from it for a while and then, you
know, kind of see it for the first time and then kind of
come back to it and like, oh, damn, this was totally worth it.
Which, I mean, just being able to step away from it is
one of the, the, the payouts from the sacrifice, right?
The, the fact that you built a business, you can step
away from for a minute,
but I wanna talk about fearing the goal a little bit because
I, I think that's fascinating to me because I, I've dealt
with it quite a bit and I certainly see it with other
founders fearing the goal that, the way I would define
it looks something like this.
It either means you never really defined the goal.
So, and, and maybe subconsciously you didn't
really define what your end game goals were because you were
afraid of what they might be.
Uh, either too small, too big, whatever.
Or the other side of it is you named something Bel Air
House, that when it came to fruition, wound up being a bust.
That's even more terrifying because you
were so sure that was it.
And then you got there.
It's just what you said about the founder with the exit.
Every founder thinks the exit's the answer.
Once I get exit, everything gets better, everything
will be different, everything will be better.
And then always become depress depressed after
having done it because they lost their sense of purpose.
They, you name it, the list go whole episodes dedicated
to to the after effect.
And I guess what I'm saying there is what's interesting
to me about folks who, with a lack of, of defined
goals, is they have no way to calibrate the sacrifice.
For example, if your ultimate goal, Ryan, was
to just go to Madrid.
Forget all the job benefits, right?
Of what we do and our freedom and stuff like that.
Just, just to get there.
There'd be a million paths that you could go on that
wouldn't, ma wouldn't require any sacrifice.
You could literally just get a job in Madrid and
accomplish that goal.
But your goals aren't that subtle, right?
Or specific.
In this case, they're broader.
You not just wanna be there.
You wanna have the freedom, you want to have, um,
enough cash to be able to do the things you wanna do.
You know, you're not living in a hobble.
There's a lot more to it.
And those things require, uh, sacrifice.
And execution, all those things.
And I think about that and I'm like, if you don't know
exactly what those things are though, like all of those
things that are important to you, then you're many cases
gonna over sacrifice you.
You're gonna like invest too much for shit you don't need
for stuff you don't need.
Yeah.
Or invest the wrong way.
Right.
You're gonna, you're gonna push towards things that
you didn't absolutely need and, and forego others that
you, you would've enjoyed.
Yeah.
I feel like, you know, in, in the founder space that.
Ambiguity is, is ambitions, comfort food, right?
The, the idea that if we keep the goals amorphous, love that.
I love that.
That we can just sort of like, just keep going.
Keep it like we can just keep feeding the beast that we
know how to feed, uh, without really having to answer these
questions and face the fear of the payout, the what if, right?
Like right.
Because with the fuzzy goal, we, we, we can't be disappointed.
The challenge comes right to your point, like you didn't
know exactly which house, but you sort of thought there was
some version of this thing that you wanted to do, and so you,
you couldn't be disappointed.
But then when you get there and you realize now does come
time for this very specific moment, like leading up to it,
it was just like, I'll just chase, I'll chase, I'll chase.
Right?
Feed the ambition, feed the ambition, feed the ambition.
When it comes time to eat that meal, and you just go,
I actually don't want this.
We also can't be satisfied.
So I think that's the, the real danger.
Around giving into the fear of some level of definition.
Is that right?
We, we can't be disappointed by a fuzzy goal, but we also
can't be satisfied by it.
Let's stick with that.
That's why when we say founders selling their company,
getting the exit, which everybody thinks is the goal.
They get it and then they're pissed off about it.
Uh, and again, just for folks that, that weren't familiar with
this, this the episodes we've done about this, that the high
level version is we sell our company and we lose our purpose.
And we realized at that moment how much our purpose
was, was worthwhile to us and then it's too late.
Our purpose being what we were building, that company,
our relationships with people, how we were getting
up in the morning, we knew exactly what to do, et cetera.
When you overnight strip all that away and you're
like, but it doesn't matter 'cause now I don't have to
worry 'cause I have money.
And now you have no reason to go.
You have no purpose in many cases.
And people be like, oh, well I'll have purpose.
I'll do charity, I'll do this.
I'll, I'll work out a lot.
I'll like, dude, yeah.
Try it.
Lemme how this, there'll be
high quality problems.
Yeah, yeah,
yeah, yeah.
It's a problem.
Um, and you'll be talking to your therapist about it.
My point is, it's one of those cases where when we define that
goal that I want exit, so I have money, so I have options.
Totally get that part.
Yeah.
Then what?
Right.
What comes after that goal?
No one thinks about what comes after that goal.
It's because we're so, we're working so hard
just to get there.
Right?
We don't plan that far ahead.
But what happens is when we don't plan any further
than that goal, we never play out that exercise.
We never say, I wanna get to an exit.
Okay, cool.
And we talk to founders about this all the time.
Awesome.
If that's what you want, great.
But let's talk about what's going to happen after that exit.
Yep.
And make sure that those things are actually what you want.
And once happen, then once we start chipping away at
'em, they're like, huh, I really would've nothing to do.
You could always say, I'll start another company,
which is what everybody does for this exact reason.
Or, or you're like, well, you know, a big part of
my social life maybe.
Was wrapped up in, in, in running a company, um, either
explicitly with like, these are people that I hang out with
and we go get drinks together.
Or implicitly, like, I have a lot more to talk about
with a lot more people 'cause we have the commonality of
being founders or whatever.
And I think what's interesting about that is when you
play these goals out.
When you really kind of play these goals out,
they're not always exactly what people wanted or they
don't solve the problems.
Rarely are they what people wanted.
Isn't that weird?
It is.
You know, something that's really funny about everything
we talk about here is that none of it is new.
Everything you're dealing with right now has been done a
thousand times before you, which means the answer already exists.
You may just not know it.
But that's okay.
That's kind of what we're here to do.
We talk about this stuff on the show, but we actually
solve these problems all dayLong@groups.startups.com.
So if any of this sounds familiar, stop guessing
about what to do, let us just give you the answers to the
test and be done with it.
It sparked another thought though, which is, was there a
point at which this happened to you or you realized
this was happening to you?
You were avoiding precision around the goal.
Yeah, because you actually didn't want the answer.
They came in
a different way and this happened maybe Brian, maybe
in the last year or so.
I think maybe in the last year or so, for the first
time in my life, I realize there's things I don't want,
and I don't want that to sound like this privileged first
world problem because it's, it was really disappointing.
Decided I didn't need the third Bentley.
Exactly, exactly right.
I had so much, you know?
Yeah, no, nothing like that.
A big part of what drove my ambition was not having shit.
Yeah.
A big part of that need was because I didn't have it.
Right.
And I've, I, I've said this before, I said, you know,
the value of anything is the fact that you don't have it.
But once you do, it drops value, you know, uh, exponentially.
Immediately.
And so I say that to say for the first time in my life,
all those big honking goals that I had just started
to be like, I actually don't want those things.
I want the idea of wanting, I'll give an example, right?
I do not want a yacht.
Now most people are like, oh, well you know, how could
you not want a yacht or like, you know, who cares?
That's ridiculous.
I don't give a shit.
What I'm saying is like I actually don't enjoy boats
whatsoever and I'm anti boat.
Right.
If you've got a boat, let's get on it.
You use it four times as I recall.
Yeah.
But I have no interest whatsoever in being yacht guy.
I respect somebody else for being yacht guy.
I don't wanna be ya guy right now.
When I say that, that means I'm taking some big
further goal that would otherwise require lots of
extra sacrifice to get to.
Off the table for a decade.
We had two homes, right?
We had one in Ohio, we one in California.
I have no desire to have a second home.
I don't even have a 1% desire to have a second home.
I hated having two homes, right?
It was a giant pain in the ass.
But when I say that, I, I'm, I feel fortunate that,
that I had that experience.
But I can also tell you, I don't ever wanna do that again.
That takes a huge, you know, uh, thing off the table.
Huge.
And I, I think it comes from these places so often, right?
Like in your case it came from, from not having and then
wanting to have, and then we forget that we can shift outta
that gear at some point, right?
When it's just like, didn't have, and just like, so the
answer to that is, again, it's, it's have more, it's funny.
Yeah.
I don't want a second home right now.
What I do want is a big table somewhere.
It's not gonna fit in my Madrid apartment, right?
It is not.
There's no room in this place for a big table.
What's a big table look like?
I realized the other day, one of the things I do miss is
a big outdoor table uhhuh, where I can gather a bunch of
friends, I can cook some good food, and we can sit down and
have a nice meal together.
And so at some point.
I want a big table again, but like, it's a pretty
simple flipping goal, right?
Right.
Like, I don't need, I don't need, like, I
don't need miles of land.
I need like, you know, a a a couple hundred meters and
uh, and a big table outside somewhere that I can get to
within a, a reasonable amount of time and go and cook over fire.
Whatever it is I like to do out there that I want, I do, I still
want that, but like, yep, that's insanely achievable, right?
That's not, I don't need an exit for that.
I need.
He'd probably had a plan for three weeks and then figure that
out.
Yeah.
Well, okay, so, but this is what I mean by by that fear though.
The fear of the goal.
Yeah.
Once I started taking things off of my list, my fear started
to go the other direction.
I'm like, well, if I take my wants off the list, doesn't
my ambition go with that?
If you don't have a bunch of, you know, big ticket items
or, you know, whatever your, your, your list is, I'm just,
I'm naming random stuff.
Then all of a sudden, aren't you, ambitionless are like,
isn't the the best person, the old school, Gordon
Gecko, that you know, the only answer to more is more.
And I'm like, I ran that path for a very long time.
Long enough to know that it is soulless at best
and destructive at worst.
Yeah, yeah, for sure.
Every time I got thing it became exponentially of less value
than the next thing and the next thing and the next thing.
We've talked about this before and I think I started to fear
that part, Ryan, I started to fear that like, what if I hit
this threshold where there's just nothing else I want?
Do I lose all my ambition?
Does my superpower of of ambition directly
correlate to having random shit that I don't need?
As we get older and wiser, we start to realize we can have
more of certain things that, that don't come at the cost
of, of other types of things.
Right?
Right.
More houses comes at a cost more impact to startup founders.
Doesn't necessarily, and you and I are both highly
motivated by that, right?
We're still very ambitious in terms of wanting
to solve problems for, for, for our people.
And so I think that at some point you do start to just
kind of shift what, what some of those things look
like and the the, the payoff starts to look very different.
Right, and, and the sacrifice start to balance out a period
we have to ask, is the payout worth it?
And I think maybe the scariest thing is being
confronted with that answer.
I'll give you an example.
Before I started, uh, my first company, I used to
work for a big law firm.
Called Jones Day Re and po.
Mm-hmm.
Know them well.
Yeah.
And so, uh, I'm personally for the wrong reasons.
Yeah.
So I, I worked there at the lowest position you
could possibly have.
I was the backup receptionist.
Okay.
I'm 18 years old, just, just because I, I have
to paint this portrait.
This is like 1993 ish, you know, I got my dates right and because
I didn't own a car back then.
I used to get in my like three piece suit.
Nobody wore three piece suits even back then, right?
It was the only thing I could find a goodwill.
I'm gonna stop
you.
Please tell me.
This involves roller
blades.
It involved roller blades.
Not only did it involve roller blades, I was so
late for business, right?
It involved a a suit roller blades, a briefcase.
You are that stock image that became I am the stock image.
Right?
Oh my gods.
And for those of you that aren't following, there's a famous meme
in stock image, uh, of a, of a businessman, rollerblading, and
it says, I'm late for business.
And I actually was that guy.
So I was, I was way ahead of the curve anyway, so I would
rollerblade to the shitty job.
It was far away, by the way, like I was on campus.
That was in downtown Columbus.
Yeah, that's a, that's a, that's a good, a long, long knock.
It's a good role.
That's, that's a lot of role.
But anyway, so I'd go to this job and, uh, every day I'm
answering phones and I'm, I'm like, you know, kind
of like chatting with the attorneys and stuff like that.
And on my last day there, the managing partner comes out.
I didn't even know he knew who I was.
He's like one, like such a sweet guy.
And, uh, he's like, Hey, will again, I didn't even
know how he knew my name.
He's like, uh, I heard it's your last day.
Also.
Not sure how he knew that.
He's like, would it be okay if I took you to lunch?
I'm like, wow, that's the coolest thing I've ever heard.
I mean like just such a cool move.
That guy, you know, massive influence in what he was
in and he took the time to take the fucking backup
receptionist out to to lunch.
Right.
The fact that he's a backup receptionist.
Yeah, I know.
I know, I know.
And so, so we're at lunch.
And we're talking about life and everything else like that.
And I'm like 18, 19 years old.
And I said to him, I said, Hey, I have to ask you like you are
at the top of this food chain.
Was it worth it?
Which in retrospect was like a pretty deep
question to ask this guy.
Yeah.
Right.
Who I don't even know.
Right.
But you know, me, I just, I just go all the way at all these
questions and, uh, he paused and he was like, not really.
And I thought that was like this incredibly honest answer.
Great answer.
And he says, honest answer.
Here's, here's what he said to me.
He said, well, when I go to Best Buy, I can
now buy any TV I want.
And I thought that was such a specific thing to say.
Right, right.
This
is also 1992.
Clearly, clearly at some point he didn't have a tv.
He wanted,
I
could
buy any tube TV I want in the nicest VCR.
Yes.
And, but I remember he said that specifically, he said,
but what it took to get that, you know, to be able to, to
make that wasn't worth it.
This is the guy that was the managing partner.
Right?
Like, like he was the guy.
Like that's a, and he was a young age.
It wasn't He could have, right, right.
There wasn't a bigger goal.
There wasn't a bigger payout that could have been had.
Correct.
He got the biggest payout
and I remember, and the sacrifice wasn't worth it when
he said that, and I was like.
How is that po I was expecting a totally different answer.
Okay.
I was expecting a hype video where he was like, well, son,
now that you've asked, you know, in order to become blah.
And like, I thought it was, and he was so honest,
and so clear and so kind.
And I was like, I, I'd never forgot that.
I never forgot that.
And over time, when I was looking at my goals and my
sacrifices, I kept thinking, I don't wanna be that guy.
Like, I'm so terrified of being at the top of my, my food chain
in, in having that answer.
And I, I think part of that for him, different era, different
generation, et cetera, you weren't allowed to ask if
the payout was worth it.
It was like if you had the payout at all.
This is again, different generation
Yeah.
Than
you didn't otherwise work in a factory, so go fuck yourself.
That's your payout.
Right?
Right.
Like you didn't get the luxury of evaluating it
in quite the same way.
Like he wasn't saying, Hey, it wasn't worth it and
I'm gonna quit tomorrow.
He was like, yeah, it wasn't worth it and this is
what I'm gonna do through the rest of my life, but
this is what I've got now.
Which to me felt like a death sentence.
And so, um, a well paying death sentence.
But, but my point is he did contemplate
whether it was worth it.
This guy did everything right.
You know, top law schools, you know, obviously
worked insane hours.
His, I, I can't even quantify what his sacrifice must
have been to get there.
He probably can't either, right?
Yeah, right.
Trade offs don't come with receipts.
X years.
Why miss moments Z dollars?
Think about right.
He might be the only person that actually can, 'cause he
had a timecard for all of that.
He could.
That's probably run report tell you exactly how many hours.
That's true.
But, but I guess like it's so rare that we are forced to stop
and evaluate and calculate.
Yeah.
Whether this was worth it in the fear in all of us,
just terrifies all of us.
I know.
It does me is that we get to that moment
and give that answer.
Yeah, because man, winning, winning the wrong prize
is just another version of losing and, and the idea
that we've, we've done all of this just to open that door
and like that's not what I wanted is it's terrifying.
You see this in many professions, it's
certainly not unique to, to being a founder, right?
That require a, a, a tremendous amount of sacrifice.
Lawyer's a great example, right?
Like it's, it's hard to get that far in a firm like that
and not kill yourself to do it at every possible level for
an extraordinarily long time.
Uh, doctors are the same way.
You know, the gauntlet that they have to go through just
to start practicing is bananas.
But for founders.
What's different for us is we don't know if we're
gonna get paid at all.
What they're saying is lawyers, uh, doctors, et cetera, is, I
don't know if it'll be worth it, but I'm going to get paid.
Ours is, I don't know if it'll worth it, and I don't
know if I'm gonna get paid and I don't have paid.
Yeah, it's a double whammy.
Uh, we sound unreasonable when you say it that way.
Will we sound?
What's that?
You're unreasonable, but let's talk about the
other side of the coin.
I wanna kind of wrap with this, this concept.
What if we did get it right?
What if after all of this sacrifice.
We have that moment, you know, you and Valencia,
me building my house where it's like, you know what,
this is pretty dope, right?
Yeah.
Like this, uh, this worked out awfully well.
That's what we're hoping for.
I see it happen a lot less.
I think I fell into mine.
Do you feel like you're there now?
Do you feel like you have that alignment we were sacrificing
in your payoff have, I think so.
At, at the current state it feels like that, but this is
still a very new, new part of the adventure for us.
We're at a pretty dynamic spot in terms of like where
the kids are at in life and all of that to kind of see
how, how that plays out.
'cause this, this leads to some, some big unknowns for us, right?
Which is like, we've now created these three little very
internationalized people, so.
What happens like as we get into our, and past our, our
mid age into our older age?
Like, are they just gone?
Are they like, what have we done?
Right, right.
Is this for difficulties later?
Like, will that payoff be, be, be worth it?
But I think in terms of the balance we're looking for
in life, the time freedom that we wanted, the ways to
enjoy our days, spend our time, and look for like daily
meaningful returns on that.
I can't imagine anything that had a better alignment right
now than, than what we're doing.
Um, and I think that's an important piece of this is
like, how do we turn that?
You know, when when you do find that alignment and I
think you, you end up being a bit more, I don't wanna
say reasonable, reasonable is the wrong word, but there's,
there's, I'm missing, I'm missing the, the vocabulary for
it, but this kind of alignment turns someday into today.
And I think, I think that that's a great way to put,
think that's important because, because if you were still like,
you know what, like building this house isn't enough.
I need to build a three times larger house.
I need to wait longer.
I need to sacrifice more so I can build a like, then it just
continues to stay someday.
And I think that there's really something to this, which is
like, for me, peace isn't purchased, it's specified.
Yeah.
Right.
Meaning that once I'm able to decide that like this
is actually the thing.
And it's, and it's what I want then, then this
is that, that's great.
Right?
Like for you, your goal wasn't jets.
It turned out to be a, a workshop.
This is where I, I wanna say like, I didn't, when I, I,
when I said reasonable, I don't mean that in terms of
it's smaller, it's truer.
It's more real to what, like you actually want to
do more fidelity to it.
Right.
It's, it, it's with reason.
Right.
With reason and purpose.
It's with reason reasonable in that sense.
Right.
Yeah.
Not, not reasonable and like, oh, well that's achievable.
Right.
You know, if you can't buy the Ferrari, uh, you know, buy
the, the, the matchbox version, it's nearly the same thing.
Be satisfied.
It's, that's not it at all.
Yeah.
It was that when you got down to what was actually
going to move your needle, it turned out it was that.
Yeah.
And that alignment is super powerful.
It, I didn't see it coming.
So for folks listening, essentially what happened
was, uh, we ended up moving back to Ohio.
Uh, we were initially going to, uh, remodel our house, uh,
that we don't own for 20 years.
And as I started getting like the costs and like whatever,
and I said to my wife's, like, you know, for, for what it
would cost to remodel this whole house, we could just build a new
house and for the same amount of money, just have a new.
That was the last time that was true.
And so, yeah, I was gonna say, I feel like there may have
been some scope creep somewhere along the Yeah, yeah, yeah.
An epic amount of scope creep.
So, but actually, but that all kind of ties into it.
So lemme just play this thought out.
I ended up going through this process where we find some land
and I start designing a house.
You know, I learned 3D modeling.
So I learned how to design a house, uh, which was the
most dangerous part of this.
'cause it cost nothing to draw a bigger box.
It's building the bigger box that, that, that it also
takes some time to realize.
How big those boxes are in real life compared to what
they felt like in the 3D model.
I've experie, like when I showed you
the 3D model like four years ago and I was like, Hey Ryan, I
really wanna build this thing.
And then when you walked through it.
And you were like, damn, I'm in your 3D model.
Like it
was, I'm in the 3D model.
Like, I literally, like, there was like, I, I knew which way
to turn when we walked from the living room to head like towards
the workshop, I was like, I know exactly where we're going.
Know what?
I've
done this.
You know what, it's, you've been through this
fir first person shooter.
Before
it was, I literally, I had an Xbox controller in
my hand and I was, I was navigating your home with that.
So it did feel weird app to use my feet, but I'll get over.
Yeah.
There's a, um, uh, this is the most bizarre side, but,
uh, maybe you'll appreciate this in the game fallout
for, for the gamers of you out there, Uhhuh, right.
One of the Fallout series takes you to a resort called
Greenbriar, and I think it's the open world fallout, if
I'm not, not mistaken, right?
But they, they, uh, Greenbriar is a resort in West Virginia.
I've been to the Real Green Briar.
I have not been to the, the Fallout version, but now
I'm super excited because.
There is a nuclear shelter there.
That's why it's there.
There is, right.
And, and so, uh, in the game they turned Greenbriar into
like, it doesn't matter.
But point is when I went to Greenbrier for the
first time, I actually knew where everything was.
'cause I had played the game.
Right?
It was bizarre.
I mean, it wasn't one for one, but it funny was pretty close.
Anyway, huge engine.
Um, but you're welcome Fallout fans.
So we get to the point where like, you know, I'm, I'm kinda
like, you know, designing this house or whatever, and something
really interesting happens.
I start to realize that this is what I wanted.
It wasn't, here's what it is.
I didn't wanna buy a house.
I wanted to create a house.
I, I wanted to create something where every single thing
had my fingerprint on it.
I wanted to design every square inch of the house myself.
I wanted to pick out every last thing from like the,
the timber grid of wood we're gonna use to the quality of
hinge we're gonna use, right?
Every single thing.
But I also wanted to build it with my hands, right?
And so.
About a year ago, give or take, I'm driving to the job site.
It's freezing outside, right?
It's, we're in Ohio.
It's like, it, it couldn't have been more than
like 15 degrees outside.
I'm in my pickup truck, I'm driving out to the job site and
I'm gonna go, um, run speaker cable long before you're ever
supposed to run speaker cable.
And I've got the biggest smile on my face.
It's like six 30 in the morning.
It's cold and dark outside and I've got a huge smile
on my face and I just, I just noticed it while it was
happening and I was like.
What is wrong with me?
I'm like any rational person on a Saturday at six 30 in
the morning, at the very least would be sleeping, but the
last thing they would be doing is racing to a construction
site to go put speaker cable up when there's not even
a roof on the house yet.
But I realized this is what I've always wanted to do.
Is what you wanna do.
Right?
Like that's, I'll never forget, I'm sitting in the
cab of my truck by myself and I'm freezing and I'm thinking
to myself, this is insane.
But Bel Air wasn't what I wanted.
Right?
Bel Air was status, and status is seductive.
Yeah.
But it was the craft of doing it yourself that actually
actually satisfied you.
It's, it's such an amazing finding.
It's been this amazing journey for, uh, for me and, you know,
if, for those of you that know me and have had to listen to me
drone on about this thing for the last couple years, thank
you for your, your service.
But like, I, honestly, I finally found something
that, that was worthy.
Of the sacrifice.
This gave me some funding to do what I wanted.
It gave me the, the, the freedom to do what I wanted.
There was just everything finally paid off in a way
that for the first time in my life, I actually felt
like it was a full payout.
Like I was, yeah, I was fully aligned with my sacrifice.
And Ryan, it was a huge sigh of relief.
All of a sudden, you realize like.
That decision I didn't make, it wasn't actually
the thing, right?
It's the things that I'm doing now that, that are the thing.
Can you
imagine, Ryan, if someone like 32 years ago was like, Hey,
will, one day if you sacrifice everything and give up all of
your relationships, you'll be able to drive your construction
site, come a contractor
on your own construction site, right?
Like, wait, you never saw
that coming?
But man, like, you know, I'm a obsessive carpenter,
so like I, I got to build.
Everything I've ever wanted to build with,
like, when I say no limits, that's not entirely true.
There's always limits, but like right, reasonable limits.
I get to do really extraordinary things and I,
I wouldn't, there's no way I would've been able to do
this on, on another path.
So it's very clear that this was like a singular outcome.
But when I'm out there, like I was out there, you know, I
told you this morning at six in the morning, I'm, I'm putting,
uh, speakers in the ceilings that actually do exist now.
I'm like, I'm covered in drywall.
You know, I'm covered in sawdust.
I'm sweating like crazy.
'cause in this case it's 90 degrees outside and
I'm like, I'm so happy.
I'm so incredibly happy.
'cause I find something that, that aligns with
the sacrifice that, that feels like, damn, this is,
this is what it was for.
No, it's, you know, when we, we stop optimizing scale and
we start optimizing for savor.
Something really special happens man.
Like we don't need more.
We need maybe fewer, but certainly like deeper
and better experiences.
And I think that like that absolutely does come with
experience and time, but it also, of course, you had
to create the opportunity.
It comes from sacrifice.
Sacrifice creates the conditions for it.
Now you're, you're out there, you're building again with
meaning, which of course there's a very strong metaphor here
between the house and another startup, so Yeah, yeah, yeah.
It doesn't go unnoticed.
However, it seems like a super, it aligned
well though, and so it does.
Here's what I would say.
I would say for founders out there that are kind of
wrestling with this and we're all wrestling with it, at some
level, there's, there's no version where you can go through
this startup thing and have no, never wonder whether the
sacrifice is gonna be worth it.
Or in many cases, know exactly what the, the end game is, and
if you think you do awesome, often when you get there,
it's not what you thought it was, and that's okay.
Yeah.
Its part of the journey.
But here's what I would say.
If you're going to make this sacrifice, commit to something
that you feel that you can see and touch and taste, and
feel that if I can get this, it's going to be worth it.
But the most important part of that is why and
what happens after that?
Once I get that.
Then what happens?
You know when I wake up the next day and I bought the thing, or
I've done the thing, whatever, when I wake up the next day,
what is demonstrably better?
Because for all of us, if we can't define that next thing,
if we can't figure out what the rate of pay is going to be for
our sacrifice, then none of it is ever worth it, and that is
the worst feeling about taking everything you care about.
And put it into essentially nothing.
So take that focus, take that drive, take that sacrifice,
and make sure when it's time to cash all those chips in
that you cash 'em out big and you're smiling like we are.
'cause you've got that perfect alignment.
Overthinking your startup because you're going it alone.
You don't have to, and honestly, you shouldn't because instead,
you can learn directly from peers who've been in your shoes.
Connect with bootstrap founders and the advisors
helping them win in the startups.com community.
Check out the startups.com community@www.startups.com
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