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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to the episode of
the Startup Therapy Podcast.
This is Ryan Rutan,
joined as always by my
friend, the founder,
and CEO of startups.com.
Will Schroeder.
So for everybody listening,
like imagine waking up tomorrow
and realizing that every big
goal you'd ever set, personal,
financial, your startup,
whatever, was already checked
off, right, like Victory Lab.
Or is it an identity crisis?
Will I feel like you are either
have hit that wall or you're
like you're really close to it.
So today I wanna
dissect what happens.
When the scoreboard reads
game over, but like, you're
still itching to play.
I mean, like imagine for us if
we're, we're too for a living.
Yeah.
We help other people define
their goals and, and, and
redefine their goals and keep
adding more goals to, I mean,
a startup is just a collection
of goalposts that we keep
trying to kick through and
then move to the next one.
So like.
How the hell do
we reconcile this?
I tell you what, like I have
run out of goals Now I say
that like I'm probably, and you
know this, I'm probably busier
than I've ever been in my life.
Yeah, right?
Like, yeah, yeah.
Every waking hour
is accounted for.
So when I'm saying I'm out of
goals that, that I'm probably
not quite representing, but.
Something interesting happened
to me in the last year, I
would say in the last year,
and it's been wildly like
cathartic, reflective anxiety,
driving, et cetera, in,
in that.
Isn't it funny how like the
lack of having something
to be anxious about.
Can drive anxiety all by itself.
Oh, yeah.
Well, you know this as well.
I've found plenty of new
things to get anxious about.
However, however, here,
here's what's changed.
I wanna say at a high level
that I've run out of goals.
And, and here's
what I mean by that.
'cause it's a weird thing
to say, and I am, I'm
so goal oriented, right?
Every single day, the
first thing that I do
when I start my day.
Is I make a check
checklist of stuff that
I want to do for the day.
I do it seven days a week.
Uh, so I do it, you know,
on Saturday, Sunday.
The first thing I do is I get
up and I make a list of all
the things I wanna check off.
Even when I go on vacation,
I make a checklist of
all the things I wanna
do while on vacation.
Like, like read
book, do, whatever.
And I think it's just
because I, you know, I like
checking stuff off, right?
Like, so I, I, I love, love
goals, but so I wake up one day.
And I'm 50 years old
and I'm like, what are
my next 10 year goals?
So, you know, like what is,
it's great like milestone,
you know, part of your life.
And I sit down and I try to
have this like brainstorm
personal whiteboard moment and
I come up with zero for a guy
who makes goals for a living.
That's really sad.
It's started me, me
thinking down this process.
How about you?
I don't think I'm
quite there yet.
I don't think I'm quite there.
I don't think I've,
I haven't done all of
the things I wanna do.
We're getting ready to execute
a new, a new adventure two
Fridays from, actually, by
the time you're listening
to this, everyone, four days
from you listening to this, I
will be, I'll be boarding an
airplane on the 4th of July.
Independence Day wasn't
intentional, and we're
heading off to, uh, to Madrid.
Uh, so there's still some
stuff to be done there.
Now that's, it's a very
personal kind of goal.
That's not a, a
business related goal.
But here's one that has been
giving me a little bit of peace
lately, and it's that while.
I'm getting closer and
closer to having like the
really big high level goals
that I want to completed.
But I happen to have these
three other little people
that live in my house
Yep.
Who now have started having
some of their own goals and
we're getting to some like
really interesting stages.
Right?
Like my daughter's asking me
now about college visits and
like, what's career look like?
Yeah.
And I'm like, right,
what's it not look like?
Yeah.
And so I think that.
Look, I know I'm not gonna be
as involved in their goals.
Like they won't want me to be.
I won't want to be, but like
there's gonna be some sense of
like, how can I enable that?
How do I participate?
How do I take part in that?
Or how do I even just sort
of enjoy watching them go
through the same struggles that
I went through to hit mine?
I think that's kind of
where I'm at because I.
To your point, like
we've done a lot already.
We've gotten some
of the things right.
I've had a lot of the
experiences, I've had
a ton of experiences.
I've, I've lived all over
the world, done a lot of
stuff, and, and I've been
really happy with it.
And so like, well, I, I'm kinda
in the same boat where like I
always feel like I need a goal.
And yet when I look around at
like, okay, what's the one.
Big ass thing that I
haven't, I haven't thrown
a dart at and hit yet.
There isn't one, right?
I can do bigger versions of some
of the stuff I've already done.
I could have more of some of
the stuff I've already done,
but there are very few things
left in life other than learning
how to make all of the Othello
pieces flip over just by
passing my hand over like the
commercial promise in 1984.
That I haven't done.
No, I get it.
So, so, okay.
Let's talk about what were these
goals supposed to accomplish?
Okay.
So I wanna zoom out.
I wanna zoom out and I wanna
say all of us, early in our
careers or early in our lives,
some of the folks listening
are earlier in their careers.
We set out these goals, we have
these, these big milestones
that we want to accomplish.
A lot of times we start
a startup to accomplish
some of those goals.
Yep.
I, I gotta say, early
in my life, my goals
were super simple.
Like my goals were like, so
basic Ryan, like this is, is
I'm like 17, 18 years old.
I was broken, hungry,
and my goal was this,
don't be broken hungry.
Don't be
broken, hungry.
Yeah.
Reverse my current
circumstances.
Yeah, yeah.
My methodology of what
that meant, just meant
show up at work today.
Get paid $5 an hour and eat
with that $5 an hour, and I
was perfectly fine with that.
I, I wanna isolate that moment
for a second because I think
people think entrepreneurs
always have big visions of
what they wanted to become
in the world and like they
just, you know, what worked
so hard to make it happen.
Survival.
Yeah, not so much.
There are many points in, in
many people's lives where their
expectations, and this is a big
part, where their expectations
are wildly tempered, right?
So our goals are often
a reflection of our,
our, our expectations.
Right.
Ryan, I'm guessing you don't
have a goal to play professional
soccer, nor do I have a goal
to play professional football,
like they're tempered by what
we think our realities are.
Yeah.
Now.
Both of both of my knees
agree with this decision.
By the way,
what's wild about what we do for
a living though within startups
is we know we have the ability
to do exponential things, right?
Yep.
Like we could create the next
Shopify or Spotify, right?
Like that actually is possible.
Not likely statistically,
but it is possible.
Set these goals of everybody
listening right now, that
building a startup has a goal.
That's his big honking goal.
However, what if you, what
if you could fast forward
to that goal right now?
Be at that goal.
Yeah.
How sure of you?
That life would be
dramatically different.
Yeah.
This is where it gets wonky,
right?
This is where it gets wonky.
I mean, we did, we did a full
episode on this, like kinda
like play testing your dreams.
Remember we talked about
like, well, like just if you
wanna, you think you wanna
retire at 50, play, test it
for three or four weeks at 40.
Yeah.
And, and see if it's
really what you want.
Right?
Like we talked about,
like, I wanted to go
fishing, move to Florida.
It's like I could
fish every day.
I can't.
I can fish two days
a week maximum.
Bought myself a kayak,
was like, I'll bet the
next step is a boat.
Nope, I loved my kayak.
Didn't need more than that.
It was perfect, right?
And so it's like as you start
down these paths, sometimes
you realize that like the
goal that you set at the
beginning gets recalibrated.
As you start to achieve the
stuff that happens along the
way, one of two things happens.
You realize.
I actually don't
need that thing.
Or you realize the effort
to get to that next thing
is significantly higher than
what it took me to get here.
And therefore the, the
ROI on, it's not gonna
be what I thought.
I won't go after it.
I've always said for a long time
that the value of anything is
the fact that you don't have it.
You don't have it.
Yep.
Right.
Uh, and, and I say that
because whenever I didn't
have something, I placed
so much value on it.
And let me give you kind
of different dynamics
that could play into this.
If you're in a really bad
relationship, personal
relationship with your spouse,
then in your mind, that
relationship being fixed or
replacing with another one
that you know isn't terrible
is gonna make you so much
happier, and you're gonna be
so much a different person.
If you don't have money, you
have all these, you know, past
due bills and woes, et cetera.
When you have money,
you'll be fine.
Yeah, the list goes
on and on and on.
It creates a trap for us, and
this is the part that it took
me 30 years to figure out.
It creates a trap where we can
conveniently believe that if we
have something we don't have,
that we will be fundamentally
different on the other side.
What we never get
our heads around is.
If I have been an asshole
before money, I'll likely still
be an asshole after money.
Yeah, yeah.
Yep.
Or you know, or
whatever your thing is.
If you are the person that
always got in fights in your
relationship, when you find
your next relationship, you're
probably still the person
that always gets in fights.
You're just now getting in
fights with someone else.
Someone else.
Yep.
Yep.
Well, I haven't had nearly
as many fights with this
person 'cause we haven't been
together for nearly as long.
Exactly.
Right.
Yeah.
So I wanna start by, by
talking about how we kind
of sensationalize the
other side of these goals
without having a real good
understanding of whether or
not getting to that goal is
really gonna change anything.
Yeah.
Because in my experience,
having gone after a gazillion
goals, I would say, I'm making
this up 10% of the time.
The goal was worth it,
which is shocking to
me.
Yeah.
Which is shocking.
Yeah.
So I would draw a distinction,
just I, I'm curious
your thoughts like the.
Worth it versus
what you expected.
Right?
If 10% of the time the goals
were worth it, would you
say 10% of the time it was
exactly what you expected?
Like, I got this thing,
now I feel this much better
about life, and it's exactly
how I expected it to go.
I would say in most cases, most
cases, the joy of accomplishing
that goal was so insanely
short lived, comparative
to the work it took to get
there, that it was like.
What the hell, man?
And, and, and again, I think
when people consider, you know,
I want to have these big goals.
My startup has these big
goals, but I wanna make, I
wanna make my startup huge.
Do you Right?
Like, do you actually know that
that's gonna work out for you?
It usually does not.
Right, right.
Usually miserable by
the time you get there.
Where I was most surprised in
life, and this is, you know,
again, all mapping back to
goals was, was how often I
would set goals that I'd work
insanely hard to accomplish.
I'd get, I'd get the trophy,
the thing, whatever it is I was
trying to get to, and the amount
of value it drove to me was.
Freakishly low.
Yeah.
It's your point.
The value of something is, is
the fact that you don't have it.
We were talking about a group
of guys a couple weeks ago
talking about like, you know,
investments later in life.
Stuff like, what is it?
What do you want to amass?
What do you want to have?
And then, and then somebody
posed a question, well, like,
well, as you're thinking through
that, like what are the most
rapidly depreciating assets?
And I jokingly,
immediately responded.
I was like, mine.
Right?
Basically meaning that like once
I have it right, like, and now
that's not entirely true, right?
If you're talking about purely
monetary standpoint Sure.
Owning piece of real
estate, whatever.
Yeah.
It, it has, it has continued
value to some degree, but to
your point, like the reason
we set the goal in the first
place and then we set out to
accomplish it, the importance
of that tends to diminish.
Kind of the minute we, we
hit it, and particularly
founders as a group.
I don't know if there's anybody
that's maybe professional
athletes or the people like
that where it's like, the minute
I have a Super Bowl ring, the
only thing that's gonna make
me happy is the second one.
But founders like the,
the second we set.
Goal, we chase it maniacally.
The second we accomplish
it, we replace it with
another like that.
But the longevity of
the benefit is way less
than we think it is now.
Now lemme give
you some examples.
So someone will say, well,
if you sold your company for
a hundred million dollars
and you've took 20 million
off the table, let that 20
million lasts you forever
and longevity's forever.
So your argument's
bullshit, not exactly, yes.
Numerically the
money's in the bank.
I get that.
Yep.
What you're missing when
you say that is you think.
You are going to be okay.
And here's what everybody will
say, and I, and I get this
argument except that it winds
up being wrong and they say,
well, look, I have a bunch of
stuff I can't afford right now.
Right?
I can't afford mortgage or
to be to buy a house anymore.
Yeah.
I can't afford you name it.
And when I have money, when
startup creates money and I have
money, I can buy those things.
So you're totally wrong.
Uh, I don't have my kinda.
I get that what you're missing
is once you've done that,
you picture yourself in a
head space, in an emotional
space, a a feeling of of,
of being fulfilled that
rarely ever comes true.
And Ryan, you and I have talked
about this in other podcasts
where founders sell their
business and they think that
all these things are gonna come
with the sale of their business.
Yeah, yeah,
yeah.
And
it actually makes it worse.
Yeah.
Which is really
interesting to me,
right?
I sold my business
and my identity.
Yeah.
I sold my, my business
and all my daily routines.
I sold my business and all my
friends and the people that
I talk to every day, right?
Like all of these things went
out the door with it, right?
And now you're sitting there
with money in the bank and
an absolute identity crisis
and no idea what to do next.
Right?
And look, I mean, I, again,
if you have the choice between
being broke with an identity
crisis and rich with an identity
crisis, I recommend this.
Easier rich
money for sure.
You always give it away.
However, what I'm trying to to
to get at when we're talking
about what our goals we're
supposed to accomplish is
that we set these goals with
a bit of a false premise.
We set these goals with an
idea that once I achieve goal,
more things will change, and
more importantly, sustain than
I ever thought they would.
Okay, so let's assume.
You know, we can say a, okay,
maybe that's true, but there's
another side of it too, which
is once you do accomplish
this goal, whatever it is,
you get a dopamine hit.
Yeah.
Lemme give you an example.
Back in the nineties, uh, when
I was young, so long ago, Jesus,
back in the nineties when I was
young, I had this dream like I
think a lot of people did back
then, and probably whatever
the equivalent is now, that one
day I would be able to afford.
A white BMW three series.
Why was it white?
I don't know.
It was the nineties.
It was a thing.
Yeah.
That was just, that
was the target, but
it was definitely a BMW three
series.
Yeah.
And in my mind, 'cause I
was driving the biggest
piece of shit ever.
It was called an Audi 5,000,
which in its heyday it was
actually a beautiful car.
I did not own it
in it's a heyday.
That thing was so beat up, Ryan,
that the entire, uh, exhaust
in the bottom was held to the,
to the chassis by coat hangers.
Yeah.
Yeah, right.
Great solution.
Which is the only thing
I could, could afford.
Yeah.
For a short period of time, it
would melt off as time would go.
And it was so bad that when
I drove it to the dealership
to trade it in for a white
BMW three series, that it
actually, the car shut off.
Like I'm just driving
it and the car just shut
off while I'm driving it.
Yeah.
Not, not dangerous at all.
And I coasted into
the dealership.
And parked it, got out
and handed them the keys.
Like that's
on one hand you have to, I, I
would love to have known what
was going through the sales
person's head at that point.
'cause on one hand they're like,
this guy definitely needs a car.
Yet, you can't
leave without one.
And
yet, based on how he
arrived, is he actually
gonna be able to buy one?
You bet.
And so, so I'll never forget
this moment of pulling out
of the dealership in a white
three series BMW and Ryan,
I was, I was over the moon.
I thought I had won it life
and everything was gonna
be perfect thereafter.
Okay.
It was for well over 24 hours.
Right?
Well over 24 hours.
I had won it life.
Five years
in the making.
Yeah, yeah.
Yeah.
48 hours in the enjoying.
Exactly.
And that was such a perfect
kind of, um, microcosm
of what I would start
to learn about goals.
Goals are really valuable
until you get them.
Then on the other side of
it, you never quite picture
what it's gonna be like.
I was talking to a car guy, uh,
another founder, um, actually,
you know, we've referenced
him before on the podcast.
Uh, David Meyer
Hansen from Base Camp.
Yeah.
David's like crazy car guy.
And I remember like back in
the day he had like a $700,000.
Punani or whatever it was.
I mean, like he's, he's
way, way in the car.
He's a massive car
collection, whatever.
I was talking to him about
this and he said, I think
the three Sears, BM BMW
was his first, right?
Yeah.
Or maybe it was a PORs first.
The first big purchase.
Yeah, yeah, yeah, yeah.
And I remember him saying to me
in his Danish accent, he's, I'm
not gonna try to replicate it.
He's like, well, buying that, I
think, I think it was a Porsche.
He's like, buying that Porsche.
Gave me 90% of the
satisfaction that I would
ever get from buying a car.
He's like, I tried
everything afterward, right?
Like, like, his car
collection is sick.
He's like, but it never,
nothing ever even came close.
To the satisfaction of
getting that first car.
And basically, basically what he
was saying, and I felt the same
way, is that BMW gave me 90% of
the satisfaction I'd ever get.
Yeah.
From getting to that goal
because I was going, you know,
from nothing to something.
And ever since then myself,
I've probably bought 20 exotic
cars since then and nothing even
gave me 10% the value of the
satisfaction, which is funny.
Because the increment of
dopamine becomes significantly
smaller, the increment of cost
to go up to those higher levels
becomes significantly higher.
Right?
Well, you're paying more
and more money to receive
less and less joy, whatever
outcome that you wanted.
But there's another side.
Yes, a hundred percent.
But Ryan, there's
another side of it.
This is, this is what messed
with me and has messed
with me ever since and it's
probably what's been messing
with me in the last year.
I now know that what that,
like, what that next level is.
Right.
Like, I think a year or
two later I went out and I
bought like a, a Lamborghini
and I was like, oh my God.
Like it doesn't get
better than this.
And it was awesome.
Yeah.
For like 24 hours.
And then I realized that the,
the amount of time, effort,
cost, whatever you'd attach
to increasing the goal didn't
have anywhere near the payoff.
And here's, here's what's
interesting, which made me
not want to do it, right.
It's kinda like Tom Brady
saying, Hey, I've got
eight Super Bowl rings.
Like after the first one,
just none of them really
brought me anything.
I just kept doing it.
'cause I thought that's
what Tom Brady does.
I don't really wanna
do this anymore.
'cause it's, it's
killing my body.
Right?
Yeah.
I, I don't need the money.
Right.
Blah, blah, blah.
I think something interesting
happens when you accomplish
some of these goals and you
realize that the value of
going back and setting more,
I. Doesn't have a payoff.
I think that messes with you.
It does.
It does.
I mean like, and it's an
interesting and dangerous
curve to be on, right?
Because depending on
when it happens, like so
what if we're like, yeah.
You know, actually hitting a
hundred thousand an MRR for
the business probably won't
bring that much more joy.
Fuck it.
I'm just not gonna, I'm
not gonna move and look.
That might be absolutely fine.
I think it depends on what
you set out to accomplish.
Why, you know, do
you have investors?
Do you have a big team
that's all, all expecting
you to do these things?
Did you make those promises?
If you didn't, then I think it's
okay to reconsider these things.
But it is interesting because
I think that like I. Early
on, I think there were some
important milestones that
kind of needed to be hit you.
You talked about
it a little bit.
It was kinda like the ones
that are, you know, safety
or, or survival more so
than just, I want a thing.
And so I think that there
are a number of those that
once you've accomplished
them, there is probably
a longer lasting effect.
And we give credit to,
like some of my early
goals on accomplishing them
did three things for me.
One, they gave me the
immediate whatever it was.
Right.
So like sold, the first
company got cash, right?
Yeah.
Yeah.
Right.
Cool.
Right.
Got cash.
Now that cash
doesn't last forever.
Dopamine hit of achieving that
thing of, of, you know, building
a business that doesn't last.
Right.
Whatever.
What did last I. Was a
bit of a safety net that
came from that, right?
Which allowed me to
make different decisions
going forward that that
did last to some degree.
The other thing that lasted was
the memory that I could do that.
Right.
Agreed.
And that that was an asset that
I definitely carried forward.
It's like once you've
accomplished something, you
know you're capable of it.
It sets a new save point
for you and you can kind of
continue to build up from there.
So I think that's one
that we, we lose, but.
I also didn't need to
sell five companies to
know that I could do that.
Right.
One was enough.
Well, let's, let's build on
that a little bit because
I, I think there's some
important points in there.
The first thing I wanna point
out is that there are, I see
two different goal paths, if
you will, for, for everyone.
One is what I consider the
pleasure and lavish path when
people are like, oh, he buys
a hundred thousand dollars
BMW, kind of thing, right?
Like, that's just, you
know, pure pleasure.
But the other path
is around pain.
The avoidance of pain.
Okay.
Can't pay my bills, can't
make, you know, can't do a
doctor visit, you know, things
like, can't feed my family.
Kind of.
It's, dude, it's, it's eat.
Eat caviar.
Right.
And so I think initially
most of us are just
trying to avoid pain.
Right?
And, and the truth is,
for most of the world,
pain is the baseline.
Sure.
There, there's a significant
amount of pain and,
and relieving that pain
vis-a-vis security.
Is our number one goal, and that
is an incredibly important goal.
No question about it.
However, for those
folks, let's talk again.
Founders, that's our world.
For those folks that achieve
it initially, they're so
distracted by that pain
that they just assume that
when that pain goes away,
that they will be happy and
satisfied and all these things.
Yeah, yeah, yeah.
Here's what's
really interesting.
Rarely happens.
It rarely happens.
The difference is they
just don't, they just
aren't focused on pain.
Yeah.
Let me give you just a,
a different take on that.
We, we create new pain
that we then feel like
we have to go solve.
I've watched this over
and over, particularly
with founders, right?
Because we're so used to
commanding our destinies.
Yeah.
And so it throws us when
we command our destinies,
get what we want.
And then don't have the
results we expected Uhhuh
this podcast.
And so one of the interesting
things I've found is that when
you are in pain, um, now I'm
gonna use physical, actual pain.
Sure.
Right?
You've hurt something, you've
had a chronic condition.
I've had a chronic
condition that is
egregious amounts of pain.
At the time, all you wanna do is
get rid of pain, but something
happens where you do, right?
You and I both gone through,
you know, significant health
struggles and, and we've, we've
found a point where we got
on the other side of it, once
you've removed pain, it doesn't
necessarily make you happy.
It just makes you relieved
that you don't have pain.
See, it's different, right?
People think like, oh, I'm
in a bad relationship with
my spouse, and so if, if we
just break up or, you know,
settle or whatever, that all
of a sudden I'll be happy.
No, you just won't have pain.
It's not the same
as you'll be happy.
It's
the difference between
running from something and
running towards something.
Correct.
And so a lot of our goals are
about relieving pain initially.
And I would argue that
like phenomenal goal.
Yeah.
But once you've relieved
pain, right, and now you're
just looking at it strictly
from the standpoint of, of
how do I increase pleasure,
happiness, you know, uh,
whatever you call it.
That's where it starts to
get a little gnarly because
it's actually way harder
to do than people think.
A lot of people think if I
have more money, I'll just
be able to have more free
time, be able to, to go on
more vacations, et cetera.
It doesn't work like that.
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.
We owe money Mo problems, man.
We've all heard it.
It's true to a large degree.
You know, I think that there's,
there's something interesting
here, which is as you're, as
you're talking through this,
I started to think about it in
just slightly different terms.
And came to a realization
that at both ends of the
spectrum, right, whether
we're talking these like early
goals or later goals, there's
an existential component to
both, at least in my case.
Yeah.
Yeah.
The first goals were like, get
to that safety baseline, right?
Existential in the
sense of like, how do
I continue to exist?
How do I, how do I,
how do I survive?
And then the later goals.
Became more around,
why am I here?
Right.
Existential in a
very different level.
Oh right.
Yeah, yeah.
But what was crazy was like,
I don't really remember
there being a transition
point between those.
Like I ergo I didn't
understand, I'm now safe.
I can now just focus
on these kind of like
more cerebral things.
I can, I can be more
focused on the the why.
And I guess one of the
big questions is like.
Some point why are we still
chasing, which I, we've, we've
answered in a lot of different
ways today, and we've talked
about other podcasts, but I
think that was an interesting
realization for me is that
they were both existential
just at kind of different
ends of that spectrum.
And I'm not really sure how
I'm gonna reconcile this now.
Can't land this plane.
Well,
let me build on
this a little bit.
So one we have, again, we're
trying to get rid of pain.
In, in, in whatever
forms that affects us.
And let's say we do that, uh,
we get, we get rid of pain.
The absence of pain is
not pleasure, it's just
the absence of pain.
And I think that's a, that's
a, when you're in pain,
like literally you and I
have been quite physically
all you give a shit about.
You're like, I have pleasure.
I don't care.
I don't wanna be in pain.
Just get me
back to, it's a
neutral, I'll be fine.
I'll be greatt.
You bet.
You bet.
But for folks, you know, let's
take this back to, you know,
career startup, et cetera.
For founders who are like, Hey,
if I become super successful,
then I'll be happier.
That is a giant myth.
Now you'll have the absence
of pain, but that is not
the same as happiness.
No, not at all.
That's at all, and that's
what really messes with us.
Okay.
Yeah, but let me zoom
out a little bit further.
The idea is that once we hit
whatever those milestones
are, let's, let's say
we've already made it past
the video game level that
is getting out of pain.
Yep.
And now we're just trying
to maximize for pleasure,
enjoyment, happiness,
fulfillment, et cetera.
Those milestones, those
goals, if you will, are
really hard to come by.
Really hard to come by.
Yeah.
Yeah.
And one of the tricky
things about them is that
you can quickly realize
that more effort actually
doesn't buy you anything.
Let, let me build on that.
Hence, hence where I'm
at right now in life.
Okay.
Right now, buying another car
I already know is not gonna
gimme any more fulfillment.
Right.
As you know, I drive a
pickup truck, uh, and,
and I tend to, yeah.
What's in the shop, but yes.
But like buying another
car isn't gonna do that.
More vacations isn't going
to make me more happy.
Right.
Right.
For me, building things like
creating things makes me happy.
But one of the things that's
really messed with me, Ryan,
over the past year or two,
is for the first time in my
life, it's like I know better
that yes, I can put myself
on some ridiculous goal.
Yeah.
And it kind of sucks to know.
Yeah.
Yeah.
That I already know
it's not gonna work.
Yeah.
Look, I think there's this
sense that as we go from
feed me to fulfill me, that
it becomes significantly
di more difficult, right?
Like we're climbing this,
the pyramid of Maslow's
hierarchy of needs and like
we get to self-actualization,
which is where you're at.
Yeah.
And then all of a sudden we
realize like I. Someone's
kind of fucking flat, right?
And, um, the view from here
is basically the same as, so
I think, you know, for me,
as, as we're talking through
this, I'm realizing that in
some of my most successful
goals, and I don't mean
that in terms of the size of
the outcome, anything else.
Yeah.
I was as satisfied by the
chase of the goal, right?
So the accomplishment.
Was satisfactory, but I,
I need to go back and kind
of do some calculus on what
was it that made me engaged
throughout the process.
Right?
So I wasn't simply doing it
because of the end point, but
like truly like the, the, the
entire pathway was something
that I wanted to be able to do.
I go back to things
like coaching.
Hannah's first soccer team.
We won the league that
year by leaps and bounds.
That's not the part that
was like the coolest for me.
The coolest part for me was like
the individual little moments
of like that kid that had never
scored a goal that nobody ever
thought was gonna score a goal,
who never scored a goal, but we
made her into a great goalie.
Just kidding.
No, she, she scored a goal.
Right.
So it's like, what are
these things along the way?
Right?
Can we find fulfillment
in, and of course we've
all heard this, right?
You gotta, you have to enjoy the
journey, not the destination.
Sure.
But you who says that Ryan also?
Yes.
Rich
people.
Rich people.
Yeah.
Say dumb shit like that,
that you need to enjoy the
journey, not the destination.
And let, lemme expand on
that as an aside, I'm gonna
tangent for a half second.
I can't stand when rich people
give rich people advice.
Um, right.
Like these platitudes, because
I'm like, I always put an
asterisk at the end of their
quote that says, if you're rich,
if you're rich, yeah, exactly.
You can just hear it, right?
Yeah, exactly.
That comes out in the expression
they make after they finish.
It's the smug look
says if you're rich.
Yeah.
Yeah.
And, and it's, it's like,
Hey, great advice from
you, rich guy, because that
now applies to you, right?
Yeah.
Like money isn't everything.
If you're rich, if you have it.
Yeah.
Like you already have it.
Yeah.
Um, try not having it.
I never felt that way.
Right.
But, but my, but what I was
gonna say is what's been
interesting to me about, you
know, kind of chase the journey,
enjoy the journey, et cetera.
It is true, but I would
say this a bit different.
The journey is very different
if you already know you've won.
So, in other words, um, yeah.
In which
direction?
How do you
mean?
For better or for worse there?
Oh, well, I mean,
there's the question.
I'll leave it like this.
Um, when someone says, you
should really enjoy the journey,
dude, when I didn't know if I
was gonna be able to eat at the
end of the week, there's no part
of me that was like, I'm not
talking about the existential
fee.
I'm not talking about
the feed me side.
I'm, I'm, I'm
saying we're, we've.
You said we were past.
We were past
those, right?
We
were
Oh, that that's when
you've already won.
If you're optimizing
for pleasure, right.
If you're saying, you know,
I wanna go from a hundred
thousand dollars car to
quarter million dollar car,
then you can say dumb shit.
Like enjoy the journey.
Right, because you've
already won, right?
You're already
driving the white BMW.
Yeah, right, exactly.
The ride's already fine.
Like
I just, my frustration, and
I try to be mindful of this
coming out of my mouth as well,
is saying using platitudes,
like enjoy the journey with
like, almost like complete.
Like disassociation from
what people in the journey
are actually The reality.
The reality.
Yeah.
Right.
Reality.
Their experience.
They're like, enjoy the
journey of not making
payroll again this week.
Which part of that is fun?
Logging into gusto and
seeing the negative balance.
Like what?
Which part of it, right?
Like, yeah, yeah, yeah.
Figure out who I'm gonna let go.
Letting 'em know, Hey look,
I know you got fired today.
Don't worry about the
outcome of being fired.
Enjoy the journey.
By which I mean pack you
up your desk and yeah,
I think about it in
terms of, you were
mentioning soccer, right?
Yeah.
I think there is a point
where you realize that
winning at soccer isn't
going to really change your
outcome, but playing soccer.
Is going to be awesome.
I've been trying to, to
change that mentality.
Like it, it's a luxury to
have, if I'm being honest,
to be able to say, if we grow
startups.com to a hundred x
what it is now and sell it
for a gazillion dollars, it
literally won't change my life.
And that's not because
I'm so incredibly rich,
it's because I just don't
actually need anything else.
Yeah.
Right.
Like I just financially,
like there's, there's
nothing that I want.
That requires so much cash
that I have to do something
extraordinary to get it.
Now, that's not the same
as saying that like,
my ambition is gone.
It just magically disappeared.
Yeah.
It's saying that for the
first time in my life,
there's not a a, a material
object on the other side of
it, which is weird for me.
It is.
I think part of it's just
saying like, look, I don't
have to have, because.
There's nothing that I'm
being ambitious towards.
It doesn't mean that I'm not
still driven in some way, but
it doesn't necessarily have
to be that same ambition.
I think it's trying to
swap fuel sources in
the middle of a drive.
Yeah, right.
It's like, how do I say?
Like, look, I don't have
to be scared anymore.
I don't have to run towards
things and there's nothing
that I really want so bad,
but for some reason, maybe
this is the big question we
need to ask ourselves, but for
some reason I still feel like
I need to want something I,
I need to want to at least.
Look useful.
I want to be in motion.
I want to be productive.
I want those things, but
those things untethered
from a specific goal
are hard to achieve.
And so I think this is why we
come back full circle and go.
So I guess I need a goal.
So here, here's what
I've been kind of
discovering, if you will.
Um, I've been discovering
that for me for the first
time in my life, attaching
my effort to a trophy.
Doesn't buy me anything.
Yeah, it's a weird
thing to say, right?
It's a weird thing to
say, but for example, I
do not want a private jet.
Now I say that to say
private jets are wildly
expensive, right?
Like no matter how you do
it, no matter how you cut
it, they're wildly expensive.
And for people who have, you
know, great wealth or want
to achieve great wealth, a
private jet is like part and
parcel to what they want.
I've ridden on private
jets, they terrify me.
They're too small and my
wife won't get on one.
Now I'm saying that to say it's
not like we're riding private
jets all the time, and my wife
has these decisions to make.
She's been on a few and she's
like never got into it again.
Point is that's one of
the biggest like financial
achievements yet it's, and I
actually just don't want it.
It's a signal.
Yeah,
so stick with that.
I don't want a second house.
We did a second
house for a decade.
It sucked.
Always felt like we had
to be at the other house.
It was awful.
I, I'm grateful, wildly grateful
that I had that experience.
Yeah.
But now having had it, I
also, no, I don't need it.
And again, going back to the
cars and everything else, I
am shocked at this point in my
life, actually truly shocked
Brian, how much I don't want.
Now I say this in a backdrop,
you know, of building my dream
home, which is, you know,
a, a a huge thing for me.
But what was most interesting
about, you know, building a home
and, you know, as involved as
I've been is it feels like the
last thing I've ever wanted.
And that, that makes
me a little bit sad.
I was gonna say, yeah.
That, that, that's probably
gonna drive anxiety in
and of itself, right?
Yeah, it's like.
The sense that you're getting
closer to achieving that thing.
Right.
Which has taken, well, decades
on one hand, but just even since
the, the point of starting long
run.
Right.
It's been a five year process.
I remember the, the first
time we were talking
about this, because you're
looking at the land, you're
starting to do the three
renderings, all that stuff.
Yeah.
It's been a long time ago,
half a decade ago, but now
it's like, as you're nearing
the, the, the completion
of that milestone, right.
The achievement of this
one without a next quest.
Feels a bit like idling
and neutral, right?
Like engine rev,
nowhere to roll.
Like we're not good at this.
Yeah.
Well that's a Ryan, that's
a great way to put it.
Like I wasn't built for
not achieving goals and yet
at the same time I'm in a
place where I know that just
creating more goals for the
sake of creating more goals is
kind of a bullshit exercise.
Yep.
So kind of what I'm saying
is I'm trying to learn.
To do the things that I
enjoy, not because I get
a trophy, but because I
really enjoy doing them.
I'll give you an example.
Wait a minute.
Are you back to
enjoying the journey?
Will?
No.
No.
I'm not gonna enjoy the journey.
No, I'm kidding.
Like for example, I play, you
know, hockey with buddies.
You've been,
but that's actually
a great point.
'cause like at some point,
like playing another game of
hockey isn't, isn't a journey.
'cause it's not going anywhere.
It's just another game.
And that's okay.
We had some, uh, guys
that I was on the job site
with, we were building
our house, uh, last week.
They were basically saying,
um, aren't you really excited?
You know when this house is
gonna be done, we're supposed
to be done in a few months.
And I said, well, one,
it'll never actually be
done 'cause I'll be working
on this thing forever.
But number two, I said, the
whole point of doing this was to
build it, to actually physically
learn how to build things.
Yeah.
To here to do it.
Build cabinets, learn
how to do architecture,
learn how to do all these
things myself, and having
a big honking, like wildly
overwhelming goal, which is.
The nature of what we do as
founders in knowing that I
could like count on myself to
build it with my bare hands.
I mean, I think, and, and I
don't wanna be sexist here,
but like as a dude, like
provide shelter for family.
Yeah.
Like, like something very
near and dear to who,
you know, my identity.
I'll be there to make the fire
the day you open the place.
Well, I'll handle
that side of it.
Exactly.
Gave in though, so.
No, but my point is, I think
what's been interesting about
it is the folks I was talking
to last week were like, Hey, if
this house were already built,
would it have been worth buying?
And I said, absolutely not.
No.
I said, we're not building
this because we need a house.
We already have a house.
And, and, and we love our house.
We're building it.
'cause I wanted to create
something from scratch
that felt like a pen.
Ultimate moment in my life.
Yeah.
Kind of like, like a, here's
a great way to say it, as
it felt like the result
of 30 years of effort.
It's a trophy,
right?
It's, it's a trophy of sorts.
It's a trophy and it's, it's
got a very like cathartic.
Milestone.
You know what it is, Ryan?
Sure.
It's something that says, Hey
dude, mission accomplished.
You're good.
And I haven't had a
mission accomplished.
You're good in 31
years in my career.
I now we're, we're just
definitely gotta be a
follow up episode on this.
Uh, once, once you wake up
in jammies in that house and
we have to go, okay, so did
the dopamine last more than,
more than 48 hours, right.
Or now that you've
got it, it won't.
Right.
We, we sort of know it won't,
but, but stick with that
because, and again, and, and
if folks are listening to
this that, you know, I'm, I'm,
I'm trying to be open about
my feelings and my thought
process so you can kind of
just see what's in my head.
I already know that like,
hey, you know, once you get
the keys to the three series
BMW and you drive it off the
lot that the value, you know,
uh, not just financially but
emotionally plummets, it's not
that, it's knowing that I'm not
going to need a bigger house.
Right, right.
Um, and if I do, I would
love to find out what the
use case for that one is.
Will, has been banned from
driving in all 50 states, so he
had to build a house big enough
that he can drive around inside.
So that's kinda off the table.
Said differently too.
Like, you know, my kids will
leave the house presumably
like within the next 10 years,
and I literally would have no,
no need for a bigger house.
My point is, I kind of
know this is as much
houses we'll ever need.
And with that, there's a
great calming feeling to that.
Like a finality to it.
Right?
Like, like feeling like
you've, you've gotten to the
end of an important journey.
But also, here's what's
interesting, I also don't
have any expenses after this.
I. In other words,
I don't want a boat.
I don't want a second house.
Yeah.
I don't want a jet.
I don't like, I, all the
things that people buy with
a bunch of money, I don't
want any of that stuff.
Yeah.
Like my, my big purchases
right now have to do with
attachments to my skidsteer.
I was
getting ready to say like,
it's, it's another attachment
for the, uh, for the Bobcat.
Bobcat.
Yeah.
Yeah, yeah, yeah.
And, and I guess what I'm
saying is as, as, as folks
are thinking through their
careers, their progressions, as
founders, we rarely think about.
What does the end
game look like?
Is part of the, the, of a
measure of success, if you will,
the lack of needing more things.
Right Now you could get real
Buddhist and say, we should
never need them to begin with,
but, but that's not my point.
Yeah.
No, I think it is.
I think it is, and I think then
it, it goes from being like, we
go from playing like really big
games with really big trophies.
Yeah.
To micro games or
infinite games.
Yep.
Right.
I think that's kind of where
like it's, it's funny, like as
I've been really unpacking the
decision to move to Madrid, I.
For me, like we've got
a lot of reasons for the
kids, the family overall.
Like there's a lot of
reasons we wanna do this.
As I've been looking at the ones
where like, because you get to
those points where you're like,
you've justified lots of other
ways, but you're like, okay,
but why am I actually really,
'cause I, I've had to push hard
to make this happen, right?
And so why, why am I
actually doing this?
And I think part of that
was that I feel like it
will help me with some
of those infinite games.
At some point I be like, this,
this is like, why a lot of
people turn to philanthropy
at some point, right?
They're like, well, I have
all the stuff I need, so now
I'm, I'm just going to become
a, uh, a philanthropist.
I almost said philander.
That was not what I meant.
I, I literally almost
said philander.
Uh, so, and, and what do I
mean by like the infinite game?
So it's, it's things like.
Mentorship or creative crafts,
legacy projects, like continuing
to play to play soccer, like
there is a, there's an end
point for that right there.
There is definitely a point
at which I can no longer
continue that pursuit
because my body just simply
won't keep up with it.
But until then, right?
That's just one of those things.
But like those don't
necessarily have.
The same kind of outcome, right?
Like mentorship, for example,
right there, there will always
be someone new to mentor or
the, the, the mentee will
always have elevated goal.
Like, they'll be in the same
situation where like, well,
it'll help them accomplish
their goals, but like for you,
for the house, you've said this
before, it's like you're gonna
spend, you know, it took you
50 years to build it and you're
gonna spend the next 50, like,
tinkering with it and, and
adding onto it and doing all
this stuff around it, right?
Yep.
So I think.
To me, that's kind of
what it turns into.
It becomes the infinite
games where we specifically
design them so that
there is no end point.
So we can just keep playing.
Okay.
So, so stick with
that for a second.
The, just keep playing.
I always use Tom Brady as an
example 'cause he just to, to
me he just seems like such like
a pent, ultimate success story.
Again, I don't know the
guy, he might be a, a giant
ass, but point is, there's
a version in this where Tom
Brady is like, you know what,
I've, I've won Super Bowls.
I, I get it.
Yes, I'm capable of winning
a Super Bowl, but you know,
I just like passing the
ball around in the backyard.
To my kid or with my
friends, and I just enjoy
the game of playing football.
I don't need to win
Super Bowls to do it.
I just want to enjoy what it is.
Ryan is how I feel about
our jobs@startups.com.
startups.com becomes a
hundred times bigger.
I honestly don't, don't
know that it changes
our lives whatsoever.
To a large degree.
I hope it wouldn't, right?
Yeah.
Right.
I love what we do, right?
I wanna keep, I
wanna keep doing it.
Like to the extent that if it
became a hundred times larger
and it meant that we didn't get
to do some of the things that we
do now, I would not want that.
In fact,
we're not going out of our
way to keep it small either.
Right.
The point is, we're at a point
where we already get to do the
things that we enjoy the most.
Would that improve a few
things in the future?
Of course it would.
But the idea being, we're
enjoying what we get to
now, but this is, this is
the equivalent of us as Tom
Brady in the backyard, just
throwing the ball around.
Just 'cause we actually.
Enjoy it.
If I were to think about an
evolution of goals, right?
My thought is this, ideally
everyone listening achieves
all of their goals.
I'd sincerely hope that happens
and when it does, and when you
get to that point where you've
achieved so many things in life
that you've wanted to achieve,
I hope you get to the point
that I know I'm working on,
working through right now and,
and rhina, you know, I'd like
to believe you are too, that
at some point you say, my goal.
Is to be able to do the things
I love without consequence,
without goal, without something
that prevents me from not doing
it or not doing it for the
wrong reasons, not doing it
'cause I get a car at the end
of it, doing it because I just
love being covered in sawdust.
Building something that never
existed before, or spending
time with someone that I
love while I'm doing it.
And being able to just create
for the sake of creating.
I think yes, we might
run our goals, but we'll
never run a, the passion
that gets us to our goals.
And I think that kind of passion
is what we need to develop
if we're gonna be able to
do this pretty much forever.
I. 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
to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.