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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 their 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, as
founders, we are often chasing
something, many things often and
innumerable and unquantifiable.
Is it the case that as
founders, both personally
and professionally.
We just don't know when
to say enough is enough.
Yeah.
Like Ryan, it's so weird.
Like I've dealt with
this personally, but I
also, you know, we talked
to a lot of founders.
We all get the concept
of let's get more.
Right?
Bigger company,
bigger bank account.
Like everyone gets more.
What you rarely hear is, I have
enough or more specifically.
This is when I'll have enough.
Yeah.
This is when anything beyond
that becomes a liability.
Yep.
And I think that's, yeah.
I'm really excited about
unpacking this today because
I really want to talk
about how our ambition, our
quest for more turns into a
liability that destroys us.
And, and while that ambition
is initially good and it does
wonderful transformative things
for us, it also has a dark side.
When we let it just continue to
fester, that also takes us down.
It, it becomes our, our
greatest strength and
our greatest weakness.
A hundred percent, man.
So, Ryan, when you think about
ambition becoming a liability,
like what comes, like, like
how, how do you manifest that
in your head or, or in your
own life?
At some point, like it's, it's
the law of diminishing return.
And look, I think we
gotta go all the way back
to beginning on this.
Like, so why does this start?
Right?
We started in scarcity mode.
Every startup starts
in scarcity mode.
I don't care if you're
funded or not, there's
something you're scarce on.
We're in life.
You got money, you
might just be scarce and
understanding of how we're
gonna use that money, right?
There's always some
level of scarcity.
We start in scarcity mode and we
just never found the off switch.
We continue to grow
personally, professionally,
and we're rewarded for that.
People milestone our growth,
whether we want them to or not.
In some cases, other
people are looking and
going, oh, you did this.
Congratulations.
Good job.
Right?
Whether that's passing grades or
you know, getting promotions or
building your company, hitting
revenue, whatever it is, we're
we're celebrated for that.
And so it sets this thing
into motion and we, we have
this really early conditioning
around this bootstrap scarcity,
which starts to drive this.
Endless accumulation mindset
where it's just like more for
more, more for, more, more.
Because well more
must be better.
Right?
Right.
Yeah.
More always better until those
start to come at that cost.
So as you said, right, it turns
from leverage into liability
at the point where what we
end up needing to trade for
those incremental gains far
outweighs what they're worth.
Yeah, and it, it's interesting
because like, do you remember
like growing up there was
this concept of eat everything
on your plate, right?
I, I
clear your plate.
I still haven't
lost that concept.
And I'll tell you.
It has it's, it has,
it has turned into a
liability at this point.
My wife and I just laughed
about this last night.
The cost of dishes here in
Madrid, it's not cheap, right?
When you eat out, you
pay for it and it's
delightful foods, right?
So you have this, this dual
fo fold problem for me.
One, we have access to
amazing world class food.
At amazing world class prices.
And so I feel like we
shouldn't leave a scrap
of it on the table.
Right,
right,
right.
And so I'm now carrying
it around my waist.
Yeah.
I say, welcome to obesity.
And that same concept applies.
Yep.
We have this idea early on
because we're young, we're
growing, we're hungry.
Right.
And food was scarce that
we should have all of it.
We should consume all.
And the idea is a clean plate
is rewarded because you consumed
as much as you can consume.
The irony there, sorry, I just
gotta go back like so do you
remember what one of the rewards
for cleaning the plate was?
Dessert.
Yes.
You clean your place.
So if you do more than
you need to, we'll give
you even more than you.
More than you need to.
No, it it more unhealthy, right?
So yeah.
So this is, this is pretty deep.
It's very psychologically
set for me.
Yeah.
So what's interesting about
it is because we have the more
is always better mentality.
No one ever tells us when
it's time to shift or
that it's ever time to.
Right.
In fact, you're almost like
kind of punished or penalized,
especially as a founder for
the idea that you wouldn't
just inherently want more.
Yeah.
Where I think that's
interesting is when we get
into this, like you were
saying, we're broke, right?
Yep.
Maybe personally,
professionally, and
startups broke by nature.
That's how we all start, and so.
All more is good at that point.
Yes.
More revenue, more people,
more capital, more,
you know, you name it.
More is good in our personal
life, especially when
we're, uh, very young.
More is good.
Having car is good.
Having houses good, yes.
Having, you know, family
or, you know, whatever.
It's whatever your path is and.
What you don't hear about along
the way is someone saying,
so when are you gonna stop?
Yeah.
You're like, no, I'm
eating as much as I can.
Oh, like I clean every
plate, eat every dessert.
I'm like, you know,
actually that's gonna end
pretty poorly for you.
Yes.
Do you understand why?
And here's the crazy thing.
No, no.
People genuinely don't
understand why having more
could ever be a problem.
Now, to be fair, it's because
a lot of 'em, you know,
never get to eat enough.
If you're 45 years old, I'm
just making up an age and you're
like, dude, I'm so broke right
now, more ain't my problem.
Okay.
Right.
That I feel for you.
Right.
So just to be clear,
most of the world doesn't
have a moral problem.
You know, though,
like yes and no.
Obviously if you're,
if you're under fed, if
you're under sheltered.
If you're under
anything, yes, clearly.
But I think that part of the
challenge becomes when we
have a need more mentality.
Right?
Even and, and like when
we start to adopt that
without any sense for what
enough looks like, right?
Because I think that even if you
don't yet have enough, if you're
already developing that, I will
always need more mentality.
You're on the crash
course, right?
You may not be, you may not
be at a point where you're in
danger of hitting that wall,
but it approaches a lot faster
than most of us think, man.
I mean like we've talked about
this in other podcast where
what you actually need in life.
What is actually like a, a
life changing outcome or a
life changing amount of money,
or a life changing number of
things, relatively low and
relatively achievable, and yet
what happens the minute we check
all the boxes for those needs?
We erase those check marks,
draw bigger boxes and fill
them with bigger checks.
Right.
Like another plate have car,
another plate need bigger car.
Right.
Right.
Have a, have, have all the
airline travel I could ever
want, need my own plane.
Right.
Nobody needs their own plane.
That's silly.
It reminds me of, uh, remember
we, we, we talked, uh, episodes
past and I, I referenced that,
that Joseph Heller quote, uh,
he's the author of Catch 22.
Yes.
Uh, they're at some brilliant,
he and Ker vga are at some like
big billionaires, uh, penthouse
or something like that.
Yep.
Uh, VGA says to him.
Hey Joe.
Uh, how do you feel like this
guy's got more an artwork on
his walls than than your, um,
your catch 22 novel ever made?
He's like, well, I have
something he'll never have.
And he goes, what's that enough?
Yeah.
Right.
It's beautiful.
Absolutely beautiful.
I love those quotes because I
don't think any of that think
part of that story's true.
It does not matter.
Just
delightful though.
It's a perfect quote,
whether it happened or not.
I Right.
It doesn't change anything,
but I think what's
interesting about that is
when we're talking about.
You know, do I have enough?
Okay.
This isn't, do I have enough
private jets and mansions?
I'm not talking about that.
Right.
I'm saying your, your point
where you are satiated, where
you feel I'm well fed enough,
I cannot eat more off this
plate and be good is sooner
than most people think.
Yeah.
And the fact that they feel like
I won't get there until I'm,
I'm vomiting my, my meal, right.
Is ridiculous.
Here's what I mean by that.
Early in life you've
got this concept of.
A utility meaning like how much
benefit is there to having more?
And when I learned this
in my, uh, econ 1 0 1
class at, uh, college Yep.
And when I learned the
term utility, I remember
this to this day.
It said, Joe loves pizza.
And he said the first slice of
pizza that Joe Eats has the most
utility he'll he'll ever get.
Yep.
It's the same slice of pizza,
but his happiness, his, you
know, enjoyment out of it
is at its apex, the second
slice of pizza becomes less
the third, fourth, fifth,
and sixth or whatever become,
uh, significantly less.
He's still eating pizza, but
the value he gets the utility.
Drops exponentially.
Correct.
Now it, and that
always stuck with me.
Like I, in, in a weird way, I am
always maximizing for utility.
I think it's the nature of what
we do as founders, as startups.
Yeah.
I think it's right.
You know, as how do I spend
every dollar you build into
us?
Yep.
But let me, let me apply this
concept of utility or this
diminishing value of more
to how we actually live it.
I remember a few episodes
ago, Ryan, you and I were
talking about every founder
that gets their first three
series BMW typically in white.
Right.
And we said wherever you
were before the three series
BMW, until you got that
series, BMW is probably the
greatest delta of utility
you'll ever experience.
Yep.
In a car before and after
that moment was amazing.
Yeah.
Correct.
Right.
That that was a
zero to 100 moment.
Right.
Now, once you had that utility
wears off and the novelty wears
off Uhhuh and you say, well,
how do I do more than this?
Yeah.
Yeah.
You look at the next car
and the next car to get, I'm
just sticking with cars as
a, you know, a metaphor here.
You know, it could be whatever
that next thing is in your life.
And you work really hard
and you get it could be
the seven series, BMW.
I'm a car guy, so I'm, I'm
moving up interiors here.
It could be that Bentley,
it could be the bug Gotti,
you know, wherever, wherever
you go on the chain.
Right.
And what you realize when
you get that next car,
it's better in some ways.
Oh yeah.
But it's not zero to
a hundred anymore.
Nah, it's like zero to 20.
Yeah.
Right.
The zero, 10,
sometimes zero to zero.
Yeah.
Right?
Yep.
And the moment the novelty wears
off, you're like, well, shit,
I had to work so much harder.
Or even if, if we don't use
hard work as the metric, I
had to contribute value so
much more, whether it's money,
time, you know, whatever.
So much more in order to
get to that level and it
wasn't that much better.
That blows me away.
What do you think about that?
A hundred percent, man.
Like I can actually draw that
direct comparison because in the
last eight years I. I've owned
a number of cars, but I've owned
two very, very different cars.
Mm-hmm.
And I got very different level
of enjoyment from both of them.
One of them was an SL five
50, which is a very, it is a
great car, expensive Mercedes.
The other one was a 1998
Land Rover Discovery, which
wasn't a cheap car when it
was made, but it certainly
was by the time I bought it.
You know which one?
I had a lot more fun driving
around in my $4,000 clunker
of a Guatemalan, you know,
off-road vehicle that I
just, I loved the thing.
I had so much fun with that car.
And there was no
stress behind it.
There was no nothing
like it didn't, it
literally didn't matter.
If that thing had fallen in
two pieces in the middle of the
road, I would've pushed them
off to the side for everyone
else's safety and walked home
and not thought about it again.
Right.
Well you, it just such, you also
maximized no liability that,
I'll give you another example.
When I go on vacations
and as you know, I hardly
ever take vacations.
I'm just not.
It is correct.
Uh, and so when I go on
vacation, we usually try to
go to a really nice place and
'cause we hardly ever do it.
When I get to the bar, I order
the same drink every time.
Uh, vodka gimlet.
I know exactly.
I know exactly what it is.
Yeah, yeah, yeah.
You do.
You know me well.
And so it's the same pour of
Tito's anywhere in the world.
Yep.
Right.
You know, sometimes
less, sometimes more.
But it's the same drink.
There's nothing
special about it.
Right.
No, I'm not like a bourbon
guy or anything like that.
Right, right.
Nor nor is it a complicated
or complex drink.
Like you don't even need
anybody who an expert,
you cannot mess up.
You measure two, two
things nice together.
Yep.
Yeah, exactly right.
Anyway, so I'll, I'll, I'll
go to one of these resorts
and I'll go to the bar and
they'll, they'll pour me my,
my drink, which would normally
be like in, in, in what
I'd say like market prices.
Like an $8 drink.
Yep.
An $8.
Just being even like a slightly
higher end price point.
And they're like,
sir, that's $37.
And I'm like, and
I'm so offended.
I'm not, I'm not that
a-hole who like, like
makes a big stink about it.
I just, yeah.
Yeah.
Uh, privately, like
just complain to myself.
But I feel like a chump.
Yeah, I feel like a chump
because I don't feel
like I'm getting value.
Well.
You get the most utility
outta the first one.
It's the second one that
should really bother you will.
The problem is
there's five left.
You know this idea that once I
have enough of something right.
I don't necessarily realize
that as I try to get more of
it, it actually doesn't work.
Again, it's got the
diminishing value.
Right?
But if, if we apply this to,
um, our startups, it's so
powerful and I hear so few
founders talking about this.
Yeah.
If we were to say, Hey, founder.
At what point does your business
not need to grow anymore?
Like that's heresy, right?
Like how dare you talk?
My business doesn't.
At what point does the happiness
of your team outweigh the
revenue of your company?
How, yeah.
Shut up, right?
You're fired.
Get a new team.
Yeah, exactly.
But what we're really asking
in those questions is have
you thought about like when
enough is actually enough?
Have you thought in your
mind, Hey, once I get to
this threshold, the three
series BMW, just to get as
a metaphor, I'm good, Ryan.
I don't think most people have
even remotely considered that.
And it blows my mind
considering how
hard we work for it.
It is, you know, it, there,
there's so much packed into
that decision though, now
that I'm thinking about it.
For example, one of the, one
of the, the little devil's
advocacies here, right?
Yeah, I don't necessarily
need anymore, but we haven't
achieved all the impact that
we want to in the world.
You know, based on what
the problem that you're
solving for is, right?
So there's all these
other reasons, right?
Or like, yeah, I'm paid pretty
well now, but there's still
a lot of people on my team
that I'd, I'd love to be
able to pay more, or, right.
There's all of these
other things that get
baked into that decision.
So for you.
How do you start to
separate some of that out?
How do you filter those
things and how do you kind
of stack rank and order
them and say like, look,
I'm gonna base the decision
on enough for me, or enough
for my customers, or enough
for my team, enough for my
investors, enough for everybody.
Like how do you
unwind that calculus?
'cause it is not uncomplex.
Well, think
about it.
What do those things
need to achieve?
What's the end game?
So I always think as, as far as
size of company, having built
companies of all different
sizes, I've learned that as a
company grows and gets bigger
and bigger, I become less
happy because a whole bunch
of things start to happen that
affect me personally that I do
not like you now get politics.
Politics, right?
Yep.
Uh, you, you get things like,
uh, you know, I mentioned
the first company, uh, that
I had started Blue Diesel.
We merged with an agency and
then very grew very quickly
and overnight we had like a
$10 million a month payroll
that brought me no joy.
Right.
I mean, it just like, it was
so stressful and it, it was
so unnerving because it's
unfixable that I didn't like it.
Right.
Yeah.
Uh, needless to say, we have
nowhere near a $10 million a
month payroll@startups.com,
and I sleep so well
with that information.
Yeah, yeah.
Right.
Like I, I feel like if something
goes wrong for us, we can
all get in a room and fix it.
Yep.
Right.
So for me, enough is just enough
people, just enough revenue,
et cetera, so that whenever
a problem comes up, we can
fix it and the order or the
configuration of the company.
Is as stress free as possible.
Let me expand on this just
while I'm thinking about it.
Sure.
Let's build products
that stress us out less.
Yeah.
Yeah.
We just had this
discussion last week.
We just sunset a product that
that made us tons of money for
millions of dollars for years.
We just didn't like it, and so
we were like, you know what?
It stresses out.
Stresses our team out.
Let's just not do it anymore.
We will make less money in the
short term, maybe in the long
term by making that decision,
but we will be more happy.
Enough is enough.
I wouldn't say we, we have
enough revenue, we still
need a little bit more,
but we're not that far off.
Right.
And there is a point where the
reason we didn't go out and
raise like millions of dollars
of VC is because we didn't need
what that capital could provide.
Really
powerful, you know what I mean?
Yeah.
It's nice to be able to
make those decisions.
Right.
And I think that that
is a, a big part of it.
And it again, it goes
back to that saying like,
what is that little bit
more going to cost us?
Yeah.
Or in this case, what is that
little bit less gonna cost us?
Does it actually cost us enough
to make it not worth making
a decision that's productive
for the team, productive for
the people that work here,
productive for, for everybody
comes out with a good result.
So I think that is the
right way of looking at it.
There.
There was something else that
occurred to me as you were,
as you were going through that
in terms of like win where and
how we get to those decisions.
And that in some cases,
I think it's not just a
matter of do we want more.
But if we ask ourselves,
can we achieve more?
But by doing it in a
different way, right.
I think so often we just
assume that in order to to
grow bigger, we just have
to throw more of whatever it
was that we've always done.
Yeah.
At the same problem.
So we wanna grow bigger, we have
to add more head count, we want,
you know, more, more profit.
We have to add more
products we want.
Right?
And so I think that instead,
if we can start to look at
that and say, by continuously
adding the resources that we
always have, they come with
some liability of their own.
And so that's part of
what this gets introduced.
So if we can create more without
adding the liability, so can
you find ways of doing it?
Once you get to enough, I
think you really have to ask
yourself a hard question.
Is this possible without
changing the linear
relationship between.
Benefit and liability, because
if it's not right, then it
just has to be recognized
as not being worthwhile.
I'll give you an example of
where I see this as a milestone.
A lot of founders, uh, that
listen to this podcast,
you know, some of you, I'm,
I'm talking about you a few
times a year I'll get a, a
friend of mine, a founder,
uh, that'll call me out and
say, just completed my exit.
I mean, for all the obvious
reasons, I can never get
enough of those calls.
Right.
Um, if you're listening to
this podcast and you ha have
had an exit, and Ryan, do you
remember like a couple months
ago, uh, gentleman reached out
and, and by the way, uh, if
sir, if, if you remember that
we're talking about you Yes.
And he said, Hey, I've listened
to podcast for a long time,
built this business doing
50 million a rrr, et cetera.
You know, having just,
you know, it's, it's
incredible, et cetera.
And I'm like, I can never
get enough of those emails.
Right.
You know, just talking
about those success stories.
The outcomes, talking about
successes.
Yeah.
In the past couple months,
I've had a few different
of my friends reach out to
me and said, you know, will
I, I, I've had an exit.
I've come to some money.
If you're one of them, now
we're in the future, and you
call me, please make sure
I'm the first person you
call because you need to hear
what I'm about to tell you.
'cause everybody else
gonna high five you.
I'm gonna warn you.
Yeah, yeah.
Here's what I'm gonna tell you.
It, it's the same
thing I tell everybody.
Don't fuck it up.
Here's what I say.
Yep.
You've already won.
Okay?
Yes, you've won.
Now all you can do is lose.
That's it.
You have to change
your mentality.
Right.
It's not time to double down.
Right, exactly.
It's not the answer.
Most founders like,
if it's 10, it's 20.
If it's 20, it's 200.
I'm going all the way
and I'm like, are you?
That's the worst
answer possible.
Right.
You can go all the way.
Unfortunately, that that
often ends up going all the
way to zero rather than all
the way to point anywhere
else.
Well, that's my point.
This is exactly kinda
the crux of this.
What you stand to gain next.
Is tiny at best, and what you
stand to lose is everything.
You can gain 1% and lose 99%.
You have to understand when
enough is enough and you're
playing a defensive game
versus an offensive game.
That's it, man, right there.
Post win, the risk
profile flips.
Right.
All of a sudden downside
completely outweighs upside, and
I think we just don't get that.
We've been in a, I must
win to achieve upside.
The minute you do that, right,
continuing to push it, just
the risk profiles reversed.
All of a sudden the, the, the
cards have all been flipped.
I think we just don't recognize
that it's certainly not
soon enough in most cases.
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.
Best example I can think
of, Lance Armstrong.
Here's a guy who won
fucking everything.
Lance, you won everything
you won at life, dude.
You beat life.
You won, you were the
best around Dun, right?
Yeah.
And like he's got that,
um, and, and he, uh,
I, I can't even say that without
finishing anyway, but he won.
He was like, Johnny
Tour de friends, right?
Yeah.
Uh, like he, he was the guy.
And remember, he
had lived strong.
He had, um, yeah.
I mean, dude was
printing money, right?
He was just like, he,
he was the goat and then
he gets caught doping.
Right, because he has,
he has to stay on top.
He has to, to be the best.
And, and I want to say this
from two different ways.
On the one hand I get it.
Yeah.
Like the reason you were
the best is 'cause you, you,
you want to be the best,
but the moment you jabbed
yourself for the first time.
Yeah.
That's the moment where
you jumped the shark.
Right?
That's the moment.
Yes.
Enough should have been
enough, and what you're about
to do will buy you nothing
and cost you everything.
It's Tom Brady in another
season of FRI in the NFL.
Right Tom?
We got like seven
Super Bowl rings.
Right.
If you get an eighth, no
one will even remember.
No.
Right.
Like no one will
know the difference.
Yep.
And the next guy that, that
knocks you on your ass and
you don't get back up from
Yeah.
Right.
You lose
everything.
At the point you're
asking like, can you
make these in thumb size?
You've probably gone too far.
Right?
Like, you're good man.
You're good.
I think for many of us, you
know, we don't have to be
Tom Brady, Lance Armstrong
to hit this threshold.
Correct.
For many of us.
We hit this threshold and,
and you know, lemme put, put,
put this together when we hit
$200,000 a year of income.
In other words, at $200,000,
it, it works very differently
in different parts of the world.
I think in some parts of the
world, when people hear me say
that, they're like, oh, you
snobby, first world Americans.
Yeah.
In other parts of America,
the folks in San Francisco
are like, how the hell
could you live on $200,000?
Right.
I'd have 14 roommates.
Right.
So understand, I, I'm, I'm
normalizing a little bit
anyway, in America, in most
parts of America, let's say.
You couldn't buy most of
the things you need now.
It doesn't go as
far as it used to.
Right, right.
But, but you couldn't get
probably 80% to 85% of your
utility in life, house,
car, family, et cetera.
And I'm not saying
you're printing money.
I'm not.
What I'm saying is that
next 10% is geometrically
harder to get to.
Yes.
The cost of it.
If you apply risk, if you apply,
when I say what it costs you,
a lot of people just think
you know, money and time.
It's more than money and time.
It's health, it's relationships.
There's things worth way
more than money and time.
Yeah.
That tend to be what you
really pay in the price to
try to get to that next level.
Go back to your
pizza analog, right?
You get the most utility
outta the first slice.
So let's compare this
now, let's say, okay, you
still want another slice?
The price of that
slice just doubled.
You're gonna get less utility,
you're gonna pay more and just
double the price of each slice.
At what point do you
stop eating pizza?
Probably after about the
third slice, if you're
paying any attention.
And yet the, the numbers
are nowhere near that
clear in, in the game of
life and startups, right?
Your professional and personal,
uh, returns are generally not
quite that easy to see, nor
is the diminishing return.
But it's there if you
go looking for it.
And I think that's the,
that's the part where we start
to fail, is that we don't
even, we don't even look,
we don't even try to set.
A metric.
That is the final metric.
We always set a metric
knowing that once we achieve
or get close to that, we're
gonna move that bar that is
just baked into what we do.
That's the hardest part.
And so,
so let me give you my
own version of kind of
constantly moving the bar.
When we sold Blue Diesel way
back in the day as 25 years
ago when we sold that company.
Now mind you, I was
like 27 years old.
Right.
So like, like relatively
speaking, I had a whole
lot of life left to live.
It wasn't like it was time
to hang up the Spurs, right?
But in my mind, whatever
that was, the next one had
to be two to three exit.
And I hear this all
the time, right?
Hey, you just had a
life changing exit.
Yeah.
Well now I'm gonna double
down and do it again.
'cause here, here's,
here's what I always hear.
I don't want people to
think I'm a one hit wonder.
Who cares?
Who cares if you're a
one hit wonder, right?
The fact all the people out
there with zero hits are
gonna judge you as being
a one hit wonder like.
Who gives a shit, right?
Didn't give a shit.
Oh yeah,
he got lucky one time.
Okay.
Cry about it on your yacht.
Ask,
ask Rick Asley if
he cares, right?
He doesn't.
He doesn't care at all.
Every time you get Rick
ruled, he gets paid.
So with that said, I'm saying
like for founders, they get
into this thing and they're
like, okay, uh, gotta have more.
Enough is never enough.
I, I've gotta keep
pushing my ambition.
For me, I looked
at it like this.
If I didn't keep pushing
more constantly all the time,
I would lose everything.
My ambition is a hundred
percent mapped to sheer terror.
Yeah.
Like PE people think
it's, it's about greed.
No, mine's all fear.
I, I operate completely on fear.
The greed or anything I get
to have that, that comes
out out of a, at the cost
of fear is just found money.
Yes.
It's all driven by
fear.
I'm just doing this
for the fear folks.
The money is a fringe benefit.
Exactly.
Exactly.
And it's like, I'm just,
I'm so worried and I, well
have been, I should say that
if I, if I don't constantly
run myself into the ground.
That I'm gonna, I'm gonna
lose it and I'm gonna, you
know, become not ambitious.
The irony there is that that
can absolutely be what ends up
causing people to, to Exactly.
It's as if we're in the ninth
inning and, and we're up and
it's the like way at the bottom.
We're like, let's ask
for some extra innings.
Why?
All you can do at this
point is below the lead.
Like, you don't want extra
innings now you just want to
defend what you've got because.
You've done it right,
but I think this is
where we run it from.
So, because defining that
metric is gonna be very,
very individualized, right?
Mm-hmm.
What's the thought
process look like?
Like how can we help people to
get closer to being able to say,
here's how I actually pick that.
Here's how I will actually
know, other than it feels right.
When it feels right.
How do we help define that?
I went through this
catharsis last year
when I turned 50.
Right.
And it's just, it's
kind of a seminal year.
Sure.
It's the first year where
you're old, old and you
know, some old guy listening
to this is gonna be like,
oh, you know, he's like 75.
And he is like, oh,
you're a young pop.
I'm like, dude, no I'm not.
Right.
Yeah.
Like, I'm like, yes, I'm younger
than you are, and I hope that
I live as long as you do.
I genuinely do, but I,
I'm not playing that game.
Not young.
Yeah,
yeah, exactly.
Right.
But it is a threshold
moment in life.
Where you start to ask yourself,
I don't know how much longer
I can or will work, right?
Yes.
If you have that luxury or
if you have that ability,
if you have any level of
introspection at all, you
look back on your life and
you said you take inventory.
Yep.
Of all the things you did, all
the things you've accomplished,
all the misses, all the
regrets, like everything, and
you start to say, Hey, I have
enough data now where I can
actually say, was this worth it?
Yeah.
Right.
Like I, I went out, I got the
car, or I bought the house, or
I moved, you know, somewhere
else and, you know, I did
those things that I thought
would bring more happiness
and now I can do the calculus
to, to measure it Right.
Analytics style and say where
did the happiness come from?
Yeah.
You know, where was happiness?
And what I learned, you know,
in, in that process was that
there really wasn't anything
I was gonna go out and like,
acquire that was gonna make
me geometrically more happy.
In other words, like if,
if I, if I went no further
than where I am now, not
from a lack of ambition,
just for a point of utility.
Yeah.
Right.
Like I can get a
fifth slice of pizza.
I just don't, it'll
actually make me sick.
And when people hear that,
I want you to understand
it's not because I'm so
fabulously wealthy that I
just like, I, I don't know
where to park my fifth yacht.
It's 'cause I don't
need a fucking yacht.
Right.
Like, I just like, I understand
that's what a lot of people
like dream of and want.
It ain't on my list and
it would bring me no
additional
joy.
Yeah.
I think that's an important part
of it too, is, is not just to
continue because like we've used
the, we've used the car analog
and used the house analog.
I think at some point when
you're just chasing more of
the same thing, I think it
also becomes problematic.
Like at some point, correct.
Probably worth branching
out a little bit and kind
of like, yep, redefine what
does more actually look like.
Like I do.
I just need more the same
thing, like my son Jack
loves trains, loves trains,
he loves high speed trains.
He just loves the high
speed train engines.
I found him this little
variety pack of these things.
There were like 12 of them
in there and I thought,
well, that'll satisfy him.
And I was, I was dripping 'em
out like one a week, one here,
one there, one here, one there.
When you get to the 12th,
then he's just like.
I would love some
more of these things.
I'm like, why do you
need more trains?
What could there possibly be
from a variety standpoint?
Like how much more joy could
you have by having 24 of
these things as opposed to 12?
And of course he was, you
know, five at the time.
So I'm not expecting him to be
able to intellectualize this.
But how many trains are we
all collecting as adults?
Right?
Like, again, like when we talk
about the size of the company or
the, the personal bank accounts,
or you know, the number of cars
in the garage or the size of the
garage the cars are in, at what
point are we asking ourselves?
Like particularly like
is, I think you and I both
know people like this.
They've been chasing more of
the same thing for a long time
with almost like no variety.
To me, that's always
really bizarre.
Like at some point, think
about where else happiness
might be derived from and
maybe go get some more of that.
So stick with that.
That was the
discovery that I made.
What I realized was that the
place I, the bucket I kept
trying to fill, um, let's
call it stuff and let's call
it bing with business, no
longer added any more joy.
It was my fifth slice of
pizza, you know, or, or, or
wherever you tap out, right?
And I started to say, huh,
that's interesting because
up until now, those book
buckets always felt so empty
that, that, that they needed
all my time and attention.
And now.
I can add more to it, but
they're just gonna overflow.
There's nothing else I'm
really gonna do there that
that's meaningful, right?
Like I've started
nine companies.
If I start a 10th sort of who
gives a shit, that doesn't
mean I had no ambition or that
somebody day I won't do it.
I just know now that whereas
before it was a massive part
of my, my goal, my path.
Yeah.
My identity.
Now it's just not, what I
did was, and this was the
most cathartic, I looked
around and I said, I bet
there's other buckets and
other, and some people are
listening to this going, oh,
you, you think so, idiot.
Yeah, right.
But you know, your family
bucket, your health bucket,
your relationship bucket,
your spirituality bucket,
you know your fitness bucket
or health, but you name it.
And you're like, how much
time do I spend filling those?
And a friend of mine, a
founder told me this years
ago, one of our listeners,
so hopefully, uh, they'll
remember this says to me.
Will imagine if you spent
as much time and attention
and purpose and passion on
your relationships as you
did with your business.
You were that intense about
making your relationships
and I was like, well, I think
everybody would hate me, but
I would've exited three of them.
Four would've failed and
I'd still be running one.
Exactly.
Exactly.
But, but it was, it
was a good point.
Hey, will, you know, uh, there
are these other buckets that
you woefully under invested,
and what if the next level of
happiness or, or excitement or
whatever that you're looking for
isn't in the bucket that you've
been filling this whole time?
That's the thing.
So for me it was hobbies.
I went out and I started
to realize that there's
some things that I enjoy.
You know, carpentry is my thing.
Uh, building a house is my thing
that actually have nothing to
do with building a startup.
You know, there's some
parallels, but, but really
nothing to do with it.
But were buckets that were
completely empty, that I
finally got that first pizza.
Pizza feeling about, yet
you're back, back to full
utility.
You're back to full utility.
Right.
Exactly.
And I think that's where
it's, it's this, you're gotta
hedge your bets on more.
You gotta spread things
around a little bit and, and
just so much benefit to it.
Right?
I think you named
off a bunch of 'em.
For me it's been
relationships, wellness,
some craft and projects.
A lot of sport and
philanthropy have been the
things that have landed.
Like all of a sudden I found
like, wow, there's, there's
something really, really
enjoyable here and I'm getting
a lot of utility out of it.
Um, and they're bringing me
joy in ways that the, the
other things that I was chasing
hadn't for some time because I'd
already filled those buckets.
Like another part of it's
novelty, like a hundred percent.
Like I said, when if I go
and start a 10th startup,
there's nothing novel about it.
Yeah.
Something we'll, we'll do
maybe the team, et cetera,
but I've been on the journey
a million times also.
You know, that's kinda what's
cool about this business is
I basically get to live all
these other lives Vis, yeah.
All these other founders
without having to do that.
Yes.
But my thought was like,
man, what if I started
investing in other journeys,
other buckets, you know?
So I learned to
become a carpenter.
I learned to become
an architect.
I learned to become
a 3D modeler.
I learned, you know, I
learned all these other
things, and I became.
I had just as much passion.
Like Ryan, you remember when
you and I first started and
like everything we learned
from how like a pro forma
income statement works
to how marketing works to
like how HTML works, right?
Yes.
Was so exciting.
Yeah.
'cause it was so new novel.
Zero to 100 moment.
I think part of what I
lost on this path is I
ran out of those moments.
Yeah.
'cause
this bucket was full.
The 5000000th line
of HTML code I wrote.
Was not nearly as exciting.
Right?
Not nearly as exciting.
Did it's, we can all
recognize that we go Yeah.
Anytime you, any, anytime
you do that much of
something, it's gonna lose.
Its, but, and yet we don't
recognize that in some
of the most important
aspects of our lives.
Some of the, where we spend
most of our time, all of a
sudden we're like, well, haven't
rethought that in a while.
Why?
Right.
And, and I don't wanna
believe people are all
that one dimensional.
I don't wanna believe when I
meet founder person that she's
sitting there going, well,
all I can do is my startup.
There's nothing else that
would possibly bring me joy.
And I'm like, maybe that
actually, I mean, I, I
can't speak for everybody.
Maybe that's, maybe that's
true, but it feels shortsighted.
It feels like you really didn't
try too hard to, to, to look
at some of these other buckets.
Yeah.
And again, maybe you did, maybe
you did the full analysis and
this is all that matters to
you and all the power to you.
And
if you're still getting
utility and and something
from it, then great.
I think you just have to
start to question it when
it's like, this doesn't
fill me in any way anymore.
That's where it
becomes problematic.
And I think part of that,
especially in the founder
space, is this sense of
responsibility to a mission,
to a level of achievement.
Maybe nobody else is paying
any attention to, but
that we internally feel
like we have to achieve.
We have to get there, we
have to do these things,
traps us into that.
Like I, I think to some
degree, part of what we can
do today will, is just give
people permission to go look
at some other buckets and do
it before that bucket's full.
Your startup also doesn't have
to achieved everything that's
ever going to achieve before
you start filling other buckets.
You don't have to wait.
I don't think it took
me a very long time.
It took me decades to realize.
That there were other buckets
and, and, and I don't mean
I, I was like so myopic.
What I'm saying is like,
I didn't understand that
anything could be more
rewarding, so to speak Yes.
Than building company
because it was the
biggest reward.
I mean, in your
case in particular.
Well, it was, it was freedom
and safety for you that
you probably never believed
was possible once you felt
that it's a powerful drug.
Right.
Right.
So there's some, to some
degree there, there is a level
of addiction to what we do.
Right.
Yeah.
And, and we have
to question it and
self preservation, right?
Yeah.
But I think, well, I'm
definitely addicted
to self preservation
like we all should be.
One of the things I've learned
though, is that my ambition.
Expects value.
Yeah.
My ambition becomes painful
at some point, of course,
when I don't feel the
value is being rewarded.
Okay, yeah.
Yeah.
It's when I go to the bar and I
order that drink and it's $37,
I'm like, you know how hard
I work to be at this bar, and
now I feel like a chump because
I'm not getting my value again.
I quietly grumble by myself.
I'm just not that guy that like
creates the scene, but in my
mind I'm like, I, I get it.
I understand why this is
happening, but I'm mad and
the reason is I expect.
If I work really hard
for something that I'm
gonna get value out of,
out of that relationship.
Right.
A good example is
a spoiled child.
Yeah.
You work so hard to raise this
child and provide for them
and you sacrifice so much and
then they're a-holes and you
look at that and you're angry
know for all these reasons,
but part of that is your
ambition in what you, you put
into this expected a return.
Now whether or not that
was an entitlement you
shouldn't have had is, is,
is subject to question.
Yeah.
Everybody's different.
That's why you feel that way.
Years ago, and Ryan, I think you
remember this, my family and I,
we had moved to Beverly Hills.
We had a nice enough house.
It wasn't very big.
Not that that was an issue, but
it was like particularly small.
And uh, my son was born,
so there's four of us.
We just ran outta a room and
we went to go look for another
house after a year and a half.
'cause finding real estate
in LA is nearly impossible.
We find this house in Bel Arrow,
it's like 10 minutes away.
Yeah.
We weren't trying to be
in Bel Arrow wasn't trying
to be the fresh prince.
That just, just happened to be
where the, where the house was.
Yeah.
Yeah.
And not a lot of inventory.
We're ready to pull the
trigger on this house.
It was really expensive,
and my wife and I sit down.
I'm like, Hey, like this
is, this is what I've
been working so hard for.
Like this is, this is
where I cash in my ticket.
And my wife, who's my wife for
a reason is like, fuck this.
She's like, there's no way we're
spending this much money Yeah.
In getting this little value.
Yeah,
yeah, yeah.
Right now.
And, and we moved back to
Ohio the, the next week.
Right, right.
So to give you an idea how
Committ talk about flipping,
were talking strict on,
on money for value there.
Yeah.
No.
There was a point where
we were just like, dude,
this is so expensive.
Yeah.
We're on a postage
stamp of land.
Right.
Like, it's like by the time
we pull our car out of the
garage, our headlight is
still in the garage where our
taillight is in the street.
Right.
This is like a big house.
Right.
It's it's crazy expensive and,
and she was like, for what we're
spending, what we could get
literally anywhere else, right?
Has so much more value,
would feel like that money
went towards something here.
Every time we pull in
the garage, it's gonna
be a $37 cocktail.
We're supposed to
feel good about it.
Yeah.
We feel like a chump.
Yeah.
Every single time.
And, and No, and I told her,
I was like, you know what?
You're right.
I was like, my ambition
expects some value.
Yeah.
And, and it, and when that
the calculus doesn't add
up, you feel like a chump.
That's when you have to
start to backpedal a little
bit and say like, okay,
so what is my ambition
actually pointing me towards?
Right, right.
And, and you know, I think
ambition's still welcome,
but we have to reprice it.
Because ambition's not the
enemy mispriced ambition, right?
Where ambition just leads
to that, you know, that,
that inverted value curve,
that's where it becomes
problematic, right?
The add you mean when you
say mispriced, I think I like
this concept, but I wanna
hear how you think about it.
Yeah.
So think about the cost of,
of ambition in terms of time,
capital, stress, whatever.
And then think about the,
the, the return, joy,
freedom, impact, right?
Then think about the, how that
leads to the decision around
where we will get the better
kind of cost averaging or return
on that investment, right?
So if we reprice our ambition
a bit and we start to say that
like, look, my ambition directed
here has a certain value.
It's almost like it's,
it's the same thing, right?
So if you ambition, if you're
spending your ambition,
you're turned ambition into
dollars, you're spending
your ambition in, in Bel
Air versus in Powell, Ohio.
Those are very
differently priced.
Right.
Same effort, completely
different value return.
Right?
Right.
And so I think this is where we
have to start to say like, what
can I point my ambition towards?
And this is going back to the,
the previous segment, which
is just look at some other
buckets and, and start to
say like, I need to maximize
my utility across buckets,
not just in a singular.
Yeah.
And, and, and I think
that for most folks, uh,
we get the ambition part.
That's how we're founders.
That's kind of, you know, what
we do and we're good at that.
Where we fail is we, we
don't have a sense for, will
I cross the finish line?
Will I win enough Super Bowls?
Yeah.
When I win, win enough, uh,
you know, tour de France, like,
uh, medals, so to speak, right?
Like in life.
And so what we do is
we just go blindly.
Toward finish line
after finish line.
After finish line.
Yeah.
Yeah.
With really no
end game in sight,
right?
No.
And then at
some point we get the
10 slice of pizza.
We don't even, we're not even,
we're sick at this point.
Yeah.
Like we ruined ourselves
in so many ways.
Yeah.
And all we know is
how to eat more pizza.
Right, and this is just
in every aspect of life.
So I think for all of us, for
founders, we need to know,
you know, when to say, when.
We need to know what
our ideal limit is.
When it's time to stop eating
and go, go do something else.
Go focus on something else.
Find that other
bucket that creates
geometrically more value.
For every bite than what
we had a moment ago.
And I think when we find that
other thing, all of a sudden
our world lights up again.
All of a sudden we're like,
damn, dude, this is how my
ambition was supposed to pay me.
It wasn't just dollars, it
wasn't just us being on,
you know, some building,
the biggest startup ever.
I was supposed to
actually be happier.
Right, your ambition as
founders, you deserve more
from your ambition, right?
You work for it, but if you're
gonna actually enjoy it, if
you're gonna get what you
deserve, you have to know when
to walk away from the table
and say, enough is enough.
I'm just so damn happy
with what I have.
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