June 30, 2025 • 40 mins
In this episode of the Startup Therapy Podcast, Ryan and Will talk about what happens when you hit all your big goals and realize there might not be any more mountains left to climb. They discuss the complex feelings and identity crises that can emerge when success is achieved, and reflect on how to find new meaning and satisfaction beyond traditional goal-setting. The conversation touches on personal anecdotes, the concept of enjoying the process, and how to appreciate the journey in a fulfilling way.
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/
What to listen for:
00:27 The Identity Crisis of Achieving Goals
01:05 Personal Reflections on Goal Setting
02:25 The Evolution of Goals Over Time
04:14 The Reality of Achieving Big Goals
07:04 The Trap of Sensationalizing Goals
10:58 The Diminishing Returns of Goal Achievement
19:06 The Two Paths of Goal Setting: Pleasure vs. Pain
20:40 Understanding Pain and Relief
21:42 The Myth of Success Equals Happiness
22:32 Existential Goals and Realizations
23:31 The Challenge of Finding Fulfillment
25:23 Enjoying the Journey vs. The Destination
29:12 Reevaluating Ambitions and Goals
33:11 Building for the Sake of Creation
36:59 Infinite Games and Lifelong Pursuits
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome back to the episode ofthe 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 biggoal you'd ever set, personal,
financial, your startup,whatever, was already checked
off, right, like Victory Lab.
(00:20):
Or is it an identity crisis?
Will I feel like you are eitherhave hit that wall or you're
like you're really close to it.
So today I wannadissect what happens.
When the scoreboard readsgame over, but like, you're
still itching to play.
I mean, like imagine for us ifwe're, we're too for a living.
Yeah.
We help other people definetheir goals and, and, and
(00:41):
redefine their goals and keepadding more goals to, I mean,
a startup is just a collectionof goalposts that we keep
trying to kick through andthen move to the next one.
So like.
How the hell dowe reconcile this?
I tell you what, like I haverun out of goals Now I say
that like I'm probably, and youknow this, I'm probably busier
than I've ever been in my life.
Yeah, right?
Like, yeah, yeah.
Every waking houris accounted for.
So when I'm saying I'm out ofgoals that, that I'm probably
(01:02):
not quite representing, but.
Something interesting happenedto 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 thelack of having something
to be anxious about.
Can drive anxiety all by itself.
Oh, yeah.
(01:23):
Well, you know this as well.
I've found plenty of newthings to get anxious about.
However, however, here,here's what's changed.
I wanna say at a high levelthat I've run out of goals.
And, and here'swhat I mean by that.
'cause it's a weird thingto say, and I am, I'm
so goal oriented, right?
Every single day, thefirst thing that I do
when I start my day.
Is I make a checkchecklist of stuff that
(01:43):
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 getup 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 wannado while on vacation.
Like, like readbook, do, whatever.
And I think it's justbecause I, you know, I like
checking stuff off, right?
Like, so I, I, I love, lovegoals, but so I wake up one day.
(02:04):
And I'm 50 years oldand 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 tohave this like brainstorm
personal whiteboard moment andI come up with zero for a guy
who makes goals for a living.
That's really sad.
It's started me, methinking down this process.
(02:25):
How about you?
I don't think I'mquite 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 executea new, a new adventure two
Fridays from, actually, bythe time you're listening
to this, everyone, four daysfrom you listening to this, I
will be, I'll be boarding anairplane on the 4th of July.
Independence Day wasn'tintentional, and we're
heading off to, uh, to Madrid.
Uh, so there's still somestuff to be done there.
(02:46):
Now that's, it's a verypersonal kind of goal.
That's not a, abusiness related goal.
But here's one that has beengiving me a little bit of peace
lately, and it's that while.
I'm getting closer andcloser to having like the
really big high level goalsthat I want to completed.
But I happen to have thesethree other little people
that live in my house
Yep.
Who now have started havingsome of their own goals and
(03:07):
we're getting to some likereally interesting stages.
Right?
Like my daughter's asking menow 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 beas involved in their goals.
Like they won't want me to be.
I won't want to be, but likethere's gonna be some sense of
like, how can I enable that?
How do I participate?
How do I take part in that?
(03:27):
Or how do I even just sortof enjoy watching them go
through the same struggles thatI went through to hit mine?
I think that's kind ofwhere I'm at because I.
To your point, likewe've done a lot already.
We've gotten someof the things right.
I've had a lot of theexperiences, I've had
a ton of experiences.
I've, I've lived all overthe world, done a lot of
stuff, and, and I've beenreally happy with it.
And so like, well, I, I'm kindain the same boat where like I
always feel like I need a goal.
(03:48):
And yet when I look around atlike, okay, what's the one.
Big ass thing that Ihaven't, I haven't thrown
a dart at and hit yet.
There isn't one, right?
I can do bigger versions of someof the stuff I've already done.
I could have more of some ofthe stuff I've already done,
but there are very few thingsleft in life other than learning
how to make all of the Othellopieces flip over just by
(04:09):
passing my hand over like thecommercial promise in 1984.
That I haven't done.
No, I get it.
So, so, okay.
Let's talk about what were thesegoals supposed to accomplish?
Okay.
So I wanna zoom out.
I wanna zoom out and I wannasay 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 havethese, these big milestones
that we want to accomplish.
(04:30):
A lot of times we starta startup to accomplish
some of those goals.
Yep.
I, I gotta say, earlyin my life, my goals
were super simple.
Like my goals were like, sobasic 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 currentcircumstances.
Yeah, yeah.
My methodology of whatthat meant, just meant
(04:52):
show up at work today.
Get paid $5 an hour and eatwith that $5 an hour, and I
was perfectly fine with that.
I, I wanna isolate that momentfor a second because I think
people think entrepreneursalways have big visions of
what they wanted to becomein the world and like they
just, you know, what workedso hard to make it happen.
Survival.
Yeah, not so much.
(05:13):
There are many points in, inmany people's lives where their
expectations, and this is a bigpart, where their expectations
are wildly tempered, right?
So our goals are oftena reflection of our,
our, our expectations.
Right.
Ryan, I'm guessing you don'thave a goal to play professional
soccer, nor do I have a goalto play professional football,
(05:35):
like they're tempered by whatwe think our realities are.
Yeah.
Now.
Both of both of my kneesagree with this decision.
By the way,
what's wild about what we do fora living though within startups
is we know we have the abilityto do exponential things, right?
Yep.
Like we could create the nextShopify or Spotify, right?
Like that actually is possible.
(05:56):
Not likely statistically,but it is possible.
Set these goals of everybodylistening right now, that
building a startup has a goal.
That's his big honking goal.
However, what if you, whatif you could fast forward
to that goal right now?
Be at that goal.
Yeah.
How sure of you?
That life would bedramatically different.
Yeah.
This is where it gets wonky,
right?
This is where it gets wonky.
(06:16):
I mean, we did, we did a fullepisode on this, like kinda
like play testing your dreams.
Remember we talked aboutlike, well, like just if you
wanna, you think you wannaretire at 50, play, test it
for three or four weeks at 40.
Yeah.
And, and see if it'sreally what you want.
Right?
Like we talked about,like, I wanted to go
fishing, move to Florida.
It's like I couldfish every day.
I can't.
I can fish two daysa week maximum.
Bought myself a kayak,was like, I'll bet the
(06:37):
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 startdown these paths, sometimes
you realize that like thegoal that you set at the
beginning gets recalibrated.
As you start to achieve thestuff that happens along the
way, one of two things happens.
You realize.
I actually don'tneed that thing.
Or you realize the effortto get to that next thing
(06:58):
is significantly higher thanwhat it took me to get here.
And therefore the, theROI on, it's not gonna
be what I thought.
I won't go after it.
I've always said for a long timethat 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 thatbecause whenever I didn't
have something, I placedso much value on it.
And let me give you kindof different dynamics
(07:19):
that could play into this.
If you're in a really badrelationship, personal
relationship with your spouse,then in your mind, that
relationship being fixed orreplacing with another one
that you know isn't terribleis gonna make you so much
happier, and you're gonna beso much a different person.
If you don't have money, youhave all these, you know, past
due bills and woes, et cetera.
When you have money,you'll be fine.
(07:39):
Yeah, the list goeson and on and on.
It creates a trap for us, andthis is the part that it took
me 30 years to figure out.
It creates a trap where we canconveniently believe that if we
have something we don't have,that we will be fundamentally
different on the other side.
What we never getour heads around is.
If I have been an assholebefore money, I'll likely still
(08:01):
be an asshole after money.
Yeah, yeah.
Yep.
Or you know, orwhatever your thing is.
If you are the person thatalways got in fights in your
relationship, when you findyour next relationship, you're
probably still the personthat always gets in fights.
You're just now getting infights with someone else.
Someone else.
Yep.
Yep.
Well, I haven't had nearlyas many fights with this
person 'cause we haven't beentogether for nearly as long.
(08:21):
Exactly.
Right.
Yeah.
So I wanna start by, bytalking about how we kind
of sensationalize theother side of these goals
without having a real goodunderstanding of whether or
not getting to that goal isreally gonna change anything.
Yeah.
Because in my experience,having gone after a gazillion
goals, I would say, I'm makingthis up 10% of the time.
(08:43):
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 versuswhat you expected.
Right?
If 10% of the time the goalswere worth it, would you
say 10% of the time it wasexactly what you expected?
Like, I got this thing,now I feel this much better
about life, and it's exactlyhow I expected it to go.
I would say in most cases, mostcases, the joy of accomplishing
(09:08):
that goal was so insanelyshort lived, comparative
to the work it took to getthere, that it was like.
What the hell, man?
And, and, and again, I thinkwhen people consider, you know,
I want to have these big goals.
My startup has these biggoals, but I wanna make, I
wanna make my startup huge.
Do you Right?
Like, do you actually know thatthat's gonna work out for you?
(09:30):
It usually does not.
Right, right.
Usually miserable bythe time you get there.
Where I was most surprised inlife, and this is, you know,
again, all mapping back togoals was, was how often I
would set goals that I'd workinsanely hard to accomplish.
I'd get, I'd get the trophy,the thing, whatever it is I was
trying to get to, and the amountof value it drove to me was.
(09:52):
Freakishly low.
Yeah.
It's your point.
The value of something is, isthe fact that you don't have it.
We were talking about a groupof 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 somebodyposed a question, well, like,
well, as you're thinking throughthat, like what are the most
rapidly depreciating assets?
And I jokingly,immediately responded.
(10:13):
I was like, mine.
Right?
Basically meaning that like onceI have it right, like, and now
that's not entirely true, right?
If you're talking about purelymonetary standpoint Sure.
Owning piece of realestate, whatever.
Yeah.
It, it has, it has continuedvalue to some degree, but to
your point, like the reasonwe set the goal in the first
place and then we set out toaccomplish it, the importance
of that tends to diminish.
Kind of the minute we, wehit it, and particularly
(10:35):
founders as a group.
I don't know if there's anybodythat's maybe professional
athletes or the people likethat where it's like, the minute
I have a Super Bowl ring, theonly 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 accomplishit, we replace it with
another like that.
But the longevity ofthe benefit is way less
(10:56):
than we think it is now.
Now lemme giveyou some examples.
So someone will say, well,if you sold your company for
a hundred million dollarsand you've took 20 million
off the table, let that 20million lasts you forever
and longevity's forever.
So your argument'sbullshit, not exactly, yes.
Numerically themoney's in the bank.
I get that.
Yep.
What you're missing whenyou say that is you think.
You are going to be okay.
(11:17):
And here's what everybody willsay, and I, and I get this
argument except that it windsup being wrong and they say,
well, look, I have a bunch ofstuff I can't afford right now.
Right?
I can't afford mortgage orto be to buy a house anymore.
Yeah.
I can't afford you name it.
And when I have money, whenstartup 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 missingis once you've done that,
(11:40):
you picture yourself in ahead space, in an emotional
space, a a feeling of of,of being fulfilled that
rarely ever comes true.
And Ryan, you and I have talkedabout this in other podcasts
where founders sell theirbusiness and they think that
all these things are gonna comewith the sale of their business.
Yeah, yeah,
yeah.
And
it actually makes it worse.
Yeah.
Which is reallyinteresting to me,
right?
I sold my businessand my identity.
(12:01):
Yeah.
I sold my, my businessand all my daily routines.
I sold my business and all myfriends and the people that
I talk to every day, right?
Like all of these things wentout the door with it, right?
And now you're sitting therewith money in the bank and
an absolute identity crisisand no idea what to do next.
Right?
And look, I mean, I, again,if you have the choice between
being broke with an identitycrisis and rich with an identity
crisis, I recommend this.
(12:23):
Easier rich
money for sure.
You always give it away.
However, what I'm trying to toto get at when we're talking
about what our goals we'resupposed to accomplish is
that we set these goals witha bit of a false premise.
We set these goals with anidea that once I achieve goal,
more things will change, andmore importantly, sustain than
I ever thought they would.
Okay, so let's assume.
(12:44):
You know, we can say a, okay,maybe that's true, but there's
another side of it too, whichis 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, whenI was young, so long ago, Jesus,
back in the nineties when I wasyoung, I had this dream like I
think a lot of people did backthen, and probably whatever
(13:04):
the equivalent is now, that oneday 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, thatwas the target, but
it was definitely a BMW three
series.
Yeah.
And in my mind, 'cause Iwas 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 itin it's a heyday.
(13:26):
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 thingI could, could afford.
Yeah.
For a short period of time, itwould melt off as time would go.
And it was so bad that whenI drove it to the dealership
to trade it in for a whiteBMW three series, that it
(13:47):
actually, the car shut off.
Like I'm just drivingit and the car just shut
off while I'm driving it.
Yeah.
Not, not dangerous at all.
And I coasted intothe dealership.
And parked it, got outand handed them the keys.
Like that's
on one hand you have to, I, Iwould love to have known what
was going through the salesperson's head at that point.
'cause on one hand they're like,this guy definitely needs a car.
(14:08):
Yet, you can't
leave without one.
And
yet, based on how hearrived, is he actually
gonna be able to buy one?
You bet.
And so, so I'll never forgetthis moment of pulling out
of the dealership in a whitethree series BMW and Ryan,
I was, I was over the moon.
I thought I had won it lifeand everything was gonna
be perfect thereafter.
(14:28):
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 perfectkind of, um, microcosm
of what I would startto learn about goals.
(14:48):
Goals are really valuableuntil you get them.
Then on the other side ofit, 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 referencedhim before on the podcast.
Uh, David MeyerHansen from Base Camp.
Yeah.
David's like crazy car guy.
And I remember like back inthe day he had like a $700,000.
(15:09):
Punani or whatever it was.
I mean, like he's, he'sway, way in the car.
He's a massive carcollection, whatever.
I was talking to him aboutthis and he said, I think
the three Sears, BM BMWwas 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 mein his Danish accent, he's, I'm
not gonna try to replicate it.
He's like, well, buying that, Ithink, I think it was a Porsche.
(15:30):
He's like, buying that Porsche.
Gave me 90% of thesatisfaction that I would
ever get from buying a car.
He's like, I triedeverything afterward, right?
Like, like, his carcollection is sick.
He's like, but it never,nothing ever even came close.
To the satisfaction ofgetting that first car.
(15:50):
And basically, basically what hewas saying, and I felt the same
way, is that BMW gave me 90% ofthe satisfaction I'd ever get.
Yeah.
From getting to that goalbecause 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 evengave me 10% the value of the
satisfaction, which is funny.
(16:10):
Because the increment ofdopamine becomes significantly
smaller, the increment of costto go up to those higher levels
becomes significantly higher.
Right?
Well, you're paying moreand more money to receive
less and less joy, whateveroutcome that you wanted.
But there's another side.
Yes, a hundred percent.
But Ryan, there'sanother side of it.
(16:31):
This is, this is what messedwith me and has messed
with me ever since and it'sprobably 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 ortwo later I went out and I
bought like a, a Lamborghiniand I was like, oh my God.
Like it doesn't getbetter than this.
And it was awesome.
Yeah.
For like 24 hours.
And then I realized that the,the amount of time, effort,
(16:52):
cost, whatever you'd attachto increasing the goal didn't
have anywhere near the payoff.
And here's, here's what'sinteresting, which made me
not want to do it, right.
It's kinda like Tom Bradysaying, 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'swhat Tom Brady does.
I don't really wannado this anymore.
'cause it's, it'skilling my body.
(17:13):
Right?
Yeah.
I, I don't need the money.
Right.
Blah, blah, blah.
I think something interestinghappens when you accomplish
some of these goals and yourealize 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 aninteresting and dangerous
curve to be on, right?
Because depending onwhen it happens, like so
what if we're like, yeah.
(17:33):
You know, actually hitting ahundred thousand an MRR for
the business probably won'tbring that much more joy.
Fuck it.
I'm just not gonna, I'mnot gonna move and look.
That might be absolutely fine.
I think it depends on whatyou set out to accomplish.
Why, you know, doyou have investors?
Do you have a big teamthat's all, all expecting
you to do these things?
Did you make those promises?
If you didn't, then I think it'sokay to reconsider these things.
(17:54):
But it is interesting becauseI think that like I. Early
on, I think there were someimportant milestones that
kind of needed to be hit you.
You talked aboutit a little bit.
It was kinda like the onesthat are, you know, safety
or, or survival more sothan just, I want a thing.
And so I think that thereare a number of those that
once you've accomplishedthem, there is probably
a longer lasting effect.
And we give credit to,like some of my early
(18:15):
goals on accomplishing themdid three things for me.
One, they gave me theimmediate whatever it was.
Right.
So like sold, the firstcompany got cash, right?
Yeah.
Yeah.
Right.
Cool.
Right.
Got cash.
Now that cashdoesn't last forever.
Dopamine hit of achieving thatthing of, of, you know, building
a business that doesn't last.
Right.
Whatever.
What did last I. Was abit of a safety net that
(18:37):
came from that, right?
Which allowed me tomake different decisions
going forward that thatdid last to some degree.
The other thing that lasted wasthe memory that I could do that.
Right.
Agreed.
And that that was an asset thatI definitely carried forward.
It's like once you'veaccomplished something, you
know you're capable of it.
It sets a new save pointfor you and you can kind of
continue to build up from there.
So I think that's onethat we, we lose, but.
I also didn't need tosell five companies to
(18:59):
know that I could do that.
Right.
One was enough.
Well, let's, let's build onthat a little bit because
I, I think there's someimportant points in there.
The first thing I wanna pointout is that there are, I see
two different goal paths, ifyou will, for, for everyone.
One is what I consider thepleasure and lavish path when
people are like, oh, he buysa hundred thousand dollars
BMW, kind of thing, right?
Like, that's just, youknow, pure pleasure.
(19:20):
But the other pathis around pain.
The avoidance of pain.
Okay.
Can't pay my bills, can'tmake, you know, can't do a
doctor visit, you know, thingslike, can't feed my family.
Kind of.
It's, dude, it's, it's eat.
Eat caviar.
Right.
And so I think initiallymost of us are just
trying to avoid pain.
Right?
And, and the truth is,for most of the world,
(19:42):
pain is the baseline.
Sure.
There, there's a significantamount of pain and,
and relieving that painvis-a-vis security.
Is our number one goal, and thatis an incredibly important goal.
No question about it.
However, for thosefolks, let's talk again.
Founders, that's our world.
For those folks that achieveit initially, they're so
distracted by that painthat they just assume that
(20:02):
when that pain goes away,that they will be happy and
satisfied and all these things.
Yeah, yeah, yeah.
Here's what'sreally interesting.
Rarely happens.
It rarely happens.
The difference is theyjust 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 painthat we then feel like
we have to go solve.
I've watched this overand over, particularly
(20:23):
with founders, right?
Because we're so used tocommanding our destinies.
Yeah.
And so it throws us whenwe command our destinies,
get what we want.
And then don't have theresults we expected Uhhuh
this podcast.
And so one of the interestingthings I've found is that when
you are in pain, um, now I'mgonna use physical, actual pain.
Sure.
Right?
You've hurt something, you'vehad a chronic condition.
(20:43):
I've had a chroniccondition that is
egregious amounts of pain.
At the time, all you wanna do isget 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'vefound a point where we got
on the other side of it, onceyou've removed pain, it doesn't
necessarily make you happy.
It just makes you relievedthat you don't have pain.
(21:04):
See, it's different, right?
People think like, oh, I'min a bad relationship with
my spouse, and so if, if wejust break up or, you know,
settle or whatever, that allof a sudden I'll be happy.
No, you just won't have pain.
It's not the sameas you'll be happy.
It's
the difference betweenrunning from something and
running towards something.
Correct.
And so a lot of our goals areabout relieving pain initially.
And I would argue thatlike phenomenal goal.
(21:27):
Yeah.
But once you've relievedpain, right, and now you're
just looking at it strictlyfrom the standpoint of, of
how do I increase pleasure,happiness, you know, uh,
whatever you call it.
That's where it starts toget a little gnarly because
it's actually way harderto do than people think.
A lot of people think if Ihave more money, I'll just
be able to have more freetime, be able to, to go on
more vacations, et cetera.
(21:47):
It doesn't work like that.
You know something that'sreally funny about everything
we talk about here isthat none of it is new.
Everything you're dealingwith right now has been done a
thousand times before you, whichmeans the answer already exists.
You may just not know it.
But that's okay.
That's kind of whatwe're here to do.
We talk about this stuff onthe show, but we actually
(22:08):
solve these problems alldayLong@groups.startups.com.
So if any of this soundsfamiliar, stop guessing
about what to do, let us justgive 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, asyou're talking through this,
(22:29):
I started to think about it injust slightly different terms.
And came to a realizationthat at both ends of the
spectrum, right, whetherwe're talking these like early
goals or later goals, there'san existential component to
both, at least in my case.
Yeah.
Yeah.
The first goals were like, getto that safety baseline, right?
Existential in thesense of like, how do
I continue to exist?
(22:49):
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 avery different level.
Oh right.
Yeah, yeah.
But what was crazy was like,I don't really remember
there being a transitionpoint between those.
Like I ergo I didn'tunderstand, I'm now safe.
I can now just focuson these kind of like
more cerebral things.
I can, I can be morefocused on the the why.
(23:11):
And I guess one of thebig questions is like.
Some point why are we stillchasing, which I, we've, we've
answered in a lot of differentways today, and we've talked
about other podcasts, but Ithink that was an interesting
realization for me is thatthey were both existential
just at kind of differentends of that spectrum.
And I'm not really sure howI'm gonna reconcile this now.
Can't land this plane.
Well,
let me build onthis a little bit.
So one we have, again, we'retrying to get rid of pain.
(23:34):
In, in, in whateverforms that affects us.
And let's say we do that, uh,we get, we get rid of pain.
The absence of pain isnot pleasure, it's just
the absence of pain.
And I think that's a, that'sa, when you're in pain,
like literally you and Ihave 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 aneutral, I'll be fine.
(23:54):
I'll be greatt.
You bet.
You bet.
But for folks, you know, let'stake 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 absenceof pain, but that is not
the same as happiness.
No, not at all.
That's at all, and that'swhat really messes with us.
Okay.
Yeah, but let me zoomout a little bit further.
(24:16):
The idea is that once we hitwhatever those milestones
are, let's, let's saywe've already made it past
the video game level thatis getting out of pain.
Yep.
And now we're just tryingto maximize for pleasure,
enjoyment, happiness,fulfillment, et cetera.
Those milestones, thosegoals, if you will, are
really hard to come by.
Really hard to come by.
Yeah.
Yeah.
And one of the trickythings about them is that
(24:39):
you can quickly realizethat more effort actually
doesn't buy you anything.
Let, let me build on that.
Hence, hence where I'mat right now in life.
Okay.
Right now, buying another carI already know is not gonna
gimme any more fulfillment.
Right.
As you know, I drive apickup truck, uh, and,
and I tend to, yeah.
What's in the shop, but yes.
But like buying anothercar isn't gonna do that.
(25:00):
More vacations isn't goingto make me more happy.
Right.
Right.
For me, building things likecreating things makes me happy.
But one of the things that'sreally messed with me, Ryan,
over the past year or two,is for the first time in my
life, it's like I know betterthat yes, I can put myself
on some ridiculous goal.
Yeah.
And it kind of sucks to know.
(25:21):
Yeah.
Yeah.
That I already knowit's not gonna work.
Yeah.
Look, I think there's thissense that as we go from
feed me to fulfill me, thatit becomes significantly
di more difficult, right?
Like we're climbing this,the pyramid of Maslow's
hierarchy of needs and likewe get to self-actualization,
which is where you're at.
Yeah.
And then all of a sudden werealize like I. Someone's
(25:41):
kind of fucking flat, right?
And, um, the view from hereis basically the same as, so
I think, you know, for me,as, as we're talking through
this, I'm realizing that insome of my most successful
goals, and I don't meanthat in terms of the size of
the outcome, anything else.
Yeah.
I was as satisfied by thechase of the goal, right?
So the accomplishment.
(26:02):
Was satisfactory, but I,I need to go back and kind
of do some calculus on whatwas it that made me engaged
throughout the process.
Right?
So I wasn't simply doing itbecause of the end point, but
like truly like the, the, theentire pathway was something
that I wanted to be able to do.
I go back to thingslike coaching.
Hannah's first soccer team.
We won the league thatyear by leaps and bounds.
(26:23):
That's not the part thatwas like the coolest for me.
The coolest part for me was likethe individual little moments
of like that kid that had neverscored 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 arethese things along the way?
Right?
Can we find fulfillmentin, and of course we've
all heard this, right?
You gotta, you have to enjoy thejourney, not the destination.
(26:44):
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 onthat as an aside, I'm gonna
tangent for a half second.
I can't stand when rich peoplegive rich people advice.
Um, right.
Like these platitudes, becauseI'm like, I always put an
(27:05):
asterisk at the end of theirquote 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 expressionthey make after they finish.
It's the smug looksays if you're rich.
Yeah.
Yeah.
And, and it's, it's like,Hey, great advice from
you, rich guy, because thatnow applies to you, right?
Yeah.
Like money isn't everything.
If you're rich, if you have it.
Yeah.
Like you already have it.
(27:26):
Yeah.
Um, try not having it.
I never felt that way.
Right.
But, but my, but what I wasgonna say is what's been
interesting to me about, youknow, kind of chase the journey,
enjoy the journey, et cetera.
It is true, but I wouldsay this a bit different.
The journey is very differentif 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?
(27:47):
Oh, well, I mean,there's the question.
I'll leave it like this.
Um, when someone says, youshould really enjoy the journey,
dude, when I didn't know if Iwas gonna be able to eat at the
end of the week, there's no partof me that was like, I'm not
talking about the existential
fee.
I'm not talking aboutthe feed me side.
I'm, I'm, I'msaying we're, we've.
You said we were past.
We were past
those, right?
We
were
Oh, that that's whenyou've already won.
If you're optimizingfor pleasure, right.
(28:09):
If you're saying, you know,I wanna go from a hundred
thousand dollars car toquarter million dollar car,
then you can say dumb shit.
Like enjoy the journey.
Right, because you'vealready won, right?
You're already
driving the white BMW.
Yeah, right, exactly.
The ride's already fine.
Like
I just, my frustration, andI try to be mindful of this
coming out of my mouth as well,is saying using platitudes,
like enjoy the journey withlike, almost like complete.
(28:32):
Like disassociation fromwhat people in the journey
are actually The reality.
The reality.
Yeah.
Right.
Reality.
Their experience.
They're like, enjoy thejourney of not making
payroll again this week.
Which part of that is fun?
Logging into gusto andseeing 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 theoutcome of being fired.
(28:52):
Enjoy the journey.
By which I mean pack youup your desk and yeah,
I think about it interms of, you were
mentioning soccer, right?
Yeah.
I think there is a pointwhere you realize that
winning at soccer isn'tgoing to really change your
outcome, but playing soccer.
Is going to be awesome.
I've been trying to, tochange that mentality.
Like it, it's a luxury tohave, if I'm being honest,
(29:15):
to be able to say, if we growstartups.com to a hundred x
what it is now and sell itfor a gazillion dollars, it
literally won't change my life.
And that's not becauseI'm so incredibly rich,
it's because I just don'tactually need anything else.
Yeah.
Right.
Like I just financially,like there's, there's
nothing that I want.
That requires so much cashthat I have to do something
(29:36):
extraordinary to get it.
Now, that's not the sameas saying that like,
my ambition is gone.
It just magically disappeared.
Yeah.
It's saying that for thefirst time in my life,
there's not a a, a materialobject on the other side of
it, which is weird for me.
It is.
I think part of it's justsaying like, look, I don't
have to have, because.
There's nothing that I'mbeing ambitious towards.
(29:56):
It doesn't mean that I'm notstill driven in some way, but
it doesn't necessarily haveto be that same ambition.
I think it's trying toswap fuel sources in
the middle of a drive.
Yeah, right.
It's like, how do I say?
Like, look, I don't haveto be scared anymore.
I don't have to run towardsthings and there's nothing
that I really want so bad,but for some reason, maybe
this is the big question weneed to ask ourselves, but for
some reason I still feel likeI need to want something I,
(30:18):
I need to want to at least.
Look useful.
I want to be in motion.
I want to be productive.
I want those things, butthose things untethered
from a specific goalare hard to achieve.
And so I think this is why wecome back full circle and go.
So I guess I need a goal.
So here, here's whatI've been kind of
discovering, if you will.
Um, I've been discoveringthat for me for the first
(30:39):
time in my life, attachingmy effort to a trophy.
Doesn't buy me anything.
Yeah, it's a weirdthing to say, right?
It's a weird thing tosay, but for example, I
do not want a private jet.
Now I say that to sayprivate jets are wildly
expensive, right?
Like no matter how you doit, no matter how you cut
it, they're wildly expensive.
And for people who have, youknow, great wealth or want
(31:00):
to achieve great wealth, aprivate jet is like part and
parcel to what they want.
I've ridden on privatejets, they terrify me.
They're too small and mywife won't get on one.
Now I'm saying that to say it'snot like we're riding private
jets all the time, and my wifehas these decisions to make.
She's been on a few and she'slike never got into it again.
Point is that's one ofthe biggest like financial
achievements yet it's, and Iactually just don't want it.
(31:21):
It's a signal.
Yeah,
so stick with that.
I don't want a second house.
We did a secondhouse for a decade.
It sucked.
Always felt like we hadto be at the other house.
It was awful.
I, I'm grateful, wildly gratefulthat I had that experience.
Yeah.
But now having had it, Ialso, no, I don't need it.
And again, going back to thecars and everything else, I
am shocked at this point in mylife, actually truly shocked
(31:42):
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 interestingabout, you know, building a home
and, you know, as involved asI've been is it feels like the
last thing I've ever wanted.
And that, that makesme a little bit sad.
(32:03):
I was gonna say, yeah.
That, that, that's probablygonna drive anxiety in
and of itself, right?
Yeah, it's like.
The sense that you're gettingcloser to achieving that thing.
Right.
Which has taken, well, decadeson 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 firsttime we were talking
about this, because you'relooking at the land, you're
starting to do the threerenderings, all that stuff.
(32:23):
Yeah.
It's been a long time ago,half a decade ago, but now
it's like, as you're nearingthe, the, the completion
of that milestone, right.
The achievement of thisone without a next quest.
Feels a bit like idlingand neutral, right?
Like engine rev,nowhere to roll.
Like we're not good at this.
Yeah.
Well that's a Ryan, that'sa great way to put it.
Like I wasn't built fornot achieving goals and yet
(32:47):
at the same time I'm in aplace where I know that just
creating more goals for thesake of creating more goals is
kind of a bullshit exercise.
Yep.
So kind of what I'm sayingis I'm trying to learn.
To do the things that Ienjoy, not because I get
a trophy, but because Ireally enjoy doing them.
I'll give you an example.
Wait a minute.
Are you back toenjoying the journey?
(33:08):
Will?
No.
No.
I'm not gonna enjoy the journey.
No, I'm kidding.
Like for example, I play, youknow, hockey with buddies.
You've been,
but that's actuallya 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, guysthat I was on the job site
with, we were buildingour house, uh, last week.
They were basically saying,um, aren't you really excited?
(33:29):
You know when this house isgonna 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 workingon this thing forever.
But number two, I said, thewhole point of doing this was to
build it, to actually physicallylearn how to build things.
Yeah.
To here to do it.
Build cabinets, learnhow to do architecture,
learn how to do all thesethings myself, and having
a big honking, like wildlyoverwhelming goal, which is.
(33:52):
The nature of what we do asfounders in knowing that I
could like count on myself tobuild it with my bare hands.
I mean, I think, and, and Idon't wanna be sexist here,
but like as a dude, likeprovide shelter for family.
Yeah.
Like, like something verynear and dear to who,
you know, my identity.
I'll be there to make the firethe day you open the place.
Well, I'll handlethat side of it.
Exactly.
Gave in though, so.
(34:12):
No, but my point is, I thinkwhat's been interesting about
it is the folks I was talkingto 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 buildingthis 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 createsomething from scratch
that felt like a pen.
Ultimate moment in my life.
(34:34):
Yeah.
Kind of like, like a, here'sa great way to say it, as
it felt like the resultof 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'sgot a very like cathartic.
Milestone.
You know what it is, Ryan?
Sure.
It's something that says, Heydude, mission accomplished.
You're good.
And I haven't had amission accomplished.
(34:56):
You're good in 31years in my career.
I now we're, we're justdefinitely gotta be a
follow up episode on this.
Uh, once, once you wake upin jammies in that house and
we have to go, okay, so didthe dopamine last more than,
more than 48 hours, right.
Or now that you'vegot it, it won't.
Right.
We, we sort of know it won't,
but, but stick with thatbecause, and again, and, and
if folks are listening tothis that, you know, I'm, I'm,
(35:18):
I'm trying to be open aboutmy feelings and my thought
process so you can kind ofjust see what's in my head.
I already know that like,hey, you know, once you get
the keys to the three seriesBMW and you drive it off the
lot that the value, you know,uh, not just financially but
emotionally plummets, it's notthat, it's knowing that I'm not
going to need a bigger house.
Right, right.
Um, and if I do, I wouldlove to find out what the
use case for that one is.
(35:41):
Will, has been banned fromdriving in all 50 states, so he
had to build a house big enoughthat he can drive around inside.
So that's kinda off the table.
Said differently too.
Like, you know, my kids willleave 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 ofknow this is as much
houses we'll ever need.
And with that, there's agreat calming feeling to that.
Like a finality to it.
(36:03):
Right?
Like, like feeling likeyou've, you've gotten to the
end of an important journey.
But also, here's what'sinteresting, 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 thethings that people buy with
a bunch of money, I don'twant any of that stuff.
Yeah.
Like my, my big purchasesright now have to do with
(36:24):
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'msaying is as, as, as folks
are thinking through theircareers, their progressions, as
founders, we rarely think about.
What does the endgame look like?
Is part of the, the, of ameasure of success, if you will,
(36:44):
the lack of needing more things.
Right Now you could get realBuddhist 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 thenit, it goes from being like, we
go from playing like really biggames with really big trophies.
Yeah.
To micro games orinfinite games.
Yep.
Right.
I think that's kind of wherelike it's, it's funny, like as
I've been really unpacking thedecision to move to Madrid, I.
(37:06):
For me, like we've gota lot of reasons for the
kids, the family overall.
Like there's a lot ofreasons we wanna do this.
As I've been looking at the oneswhere 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 hardto make this happen, right?
And so why, why am Iactually doing this?
And I think part of thatwas that I feel like it
will help me with someof those infinite games.
(37:26):
At some point I be like, this,this is like, why a lot of
people turn to philanthropyat some point, right?
They're like, well, I haveall the stuff I need, so now
I'm, I'm just going to becomea, uh, a philanthropist.
I almost said philander.
That was not what I meant.
I, I literally almostsaid philander.
Uh, so, and, and what do Imean by like the infinite game?
So it's, it's things like.
Mentorship or creative crafts,legacy projects, like continuing
(37:48):
to play to play soccer, likethere is a, there's an end
point for that right there.
There is definitely a pointat which I can no longer
continue that pursuitbecause 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'tnecessarily have.
The same kind of outcome, right?
Like mentorship, for example,right there, there will always
be someone new to mentor orthe, the, the mentee will
always have elevated goal.
(38:10):
Like, they'll be in the samesituation where like, well,
it'll help them accomplishtheir goals, but like for you,
for the house, you've said thisbefore, it's like you're gonna
spend, you know, it took you50 years to build it and you're
gonna spend the next 50, like,tinkering with it and, and
adding onto it and doing allthis stuff around it, right?
Yep.
So I think.
To me, that's kind ofwhat it turns into.
It becomes the infinitegames where we specifically
design them so thatthere is no end point.
So we can just keep playing.
(38:31):
Okay.
So, so stick withthat for a second.
The, just keep playing.
I always use Tom Brady as anexample 'cause he just to, to
me he just seems like such likea pent, ultimate success story.
Again, I don't know theguy, he might be a, a giant
ass, but point is, there'sa 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 winninga Super Bowl, but you know,
I just like passing theball around in the backyard.
(38:52):
To my kid or with myfriends, and I just enjoy
the game of playing football.
I don't need to winSuper Bowls to do it.
I just want to enjoy what it is.
Ryan is how I feel aboutour jobs@startups.com.
startups.com becomes ahundred times bigger.
I honestly don't, don'tknow that it changes
our lives whatsoever.
To a large degree.
I hope it wouldn't, right?
Yeah.
Right.
I love what we do, right?
(39:13):
I wanna keep, Iwanna keep doing it.
Like to the extent that if itbecame a hundred times larger
and it meant that we didn't getto do some of the things that we
do now, I would not want that.
In fact,
we're not going out of ourway to keep it small either.
Right.
The point is, we're at a pointwhere we already get to do the
things that we enjoy the most.
Would that improve a fewthings in the future?
Of course it would.
But the idea being, we'reenjoying what we get to
(39:33):
now, but this is, this isthe equivalent of us as Tom
Brady in the backyard, justthrowing the ball around.
Just 'cause we actually.
Enjoy it.
If I were to think about anevolution of goals, right?
My thought is this, ideallyeveryone listening achieves
all of their goals.
I'd sincerely hope that happensand when it does, and when you
get to that point where you'veachieved so many things in life
that you've wanted to achieve,I hope you get to the point
(39:55):
that I know I'm working on,working through right now and,
and rhina, you know, I'd liketo believe you are too, that
at some point you say, my goal.
Is to be able to do the thingsI love without consequence,
without goal, without somethingthat prevents me from not doing
it or not doing it for thewrong reasons, not doing it
'cause I get a car at the endof it, doing it because I just
love being covered in sawdust.
(40:16):
Building something that neverexisted before, or spending
time with someone that Ilove while I'm doing it.
And being able to just createfor the sake of creating.
I think yes, we mightrun our goals, but we'll
never run a, the passionthat gets us to our goals.
And I think that kind of passionis what we need to develop
if we're gonna be able todo this pretty much forever.
I. Overthinking your startupbecause you're going it alone.
(40:38):
You don't have to, and honestly,you shouldn't because instead,
you can learn directly frompeers who've been in your shoes.
Connect with bootstrapfounders and the advisors
helping them win in thestartups.com community.
Check out the startups.comcommunity@www.startups.com
to see if it's for you.
Could be just thething you need.
I hope to see you inside.
Welcome back to the episode ofthe 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 biggoal you'd ever set, personal,
financial, your startup,whatever, was already checked
off, right, like Victory Lab.
(00:20):
Or is it an identity crisis?
Will I feel like you are eitherhave hit that wall or you're
like you're really close to it.
So today I wannadissect what happens.
When the scoreboard readsgame over, but like, you're
still itching to play.
I mean, like imagine for us ifwe're, we're too for a living.
Yeah.
We help other people definetheir goals and, and, and
(00:41):
redefine their goals and keepadding more goals to, I mean,
a startup is just a collectionof goalposts that we keep
trying to kick through andthen move to the next one.
So like.
How the hell dowe reconcile this?
I tell you what, like I haverun out of goals Now I say
that like I'm probably, and youknow this, I'm probably busier
than I've ever been in my life.
Yeah, right?
Like, yeah, yeah.
Every waking houris accounted for.
So when I'm saying I'm out ofgoals that, that I'm probably
(01:02):
not quite representing, but.
Something interesting happenedto 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 thelack of having something
to be anxious about.
Can drive anxiety all by itself.
Oh, yeah.
(01:23):
Well, you know this as well.
I've found plenty of newthings to get anxious about.
However, however, here,here's what's changed.
I wanna say at a high levelthat I've run out of goals.
And, and here'swhat I mean by that.
'cause it's a weird thingto say, and I am, I'm
so goal oriented, right?
Every single day, thefirst thing that I do
when I start my day.
Is I make a checkchecklist of stuff that
(01:43):
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 getup 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 wannado while on vacation.
Like, like readbook, do, whatever.
And I think it's justbecause I, you know, I like
checking stuff off, right?
Like, so I, I, I love, lovegoals, but so I wake up one day.
(02:04):
And I'm 50 years oldand 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 tohave this like brainstorm
personal whiteboard moment andI come up with zero for a guy
who makes goals for a living.
That's really sad.
It's started me, methinking down this process.
(02:25):
How about you?
I don't think I'mquite 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 executea new, a new adventure two
Fridays from, actually, bythe time you're listening
to this, everyone, four daysfrom you listening to this, I
will be, I'll be boarding anairplane on the 4th of July.
Independence Day wasn'tintentional, and we're
heading off to, uh, to Madrid.
Uh, so there's still somestuff to be done there.
(02:46):
Now that's, it's a verypersonal kind of goal.
That's not a, abusiness related goal.
But here's one that has beengiving me a little bit of peace
lately, and it's that while.
I'm getting closer andcloser to having like the
really big high level goalsthat I want to completed.
But I happen to have thesethree other little people
that live in my house
Yep.
Who now have started havingsome of their own goals and
(03:07):
we're getting to some likereally interesting stages.
Right?
Like my daughter's asking menow 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 beas involved in their goals.
Like they won't want me to be.
I won't want to be, but likethere's gonna be some sense of
like, how can I enable that?
How do I participate?
How do I take part in that?
(03:27):
Or how do I even just sortof enjoy watching them go
through the same struggles thatI went through to hit mine?
I think that's kind ofwhere I'm at because I.
To your point, likewe've done a lot already.
We've gotten someof the things right.
I've had a lot of theexperiences, I've had
a ton of experiences.
I've, I've lived all overthe world, done a lot of
stuff, and, and I've beenreally happy with it.
And so like, well, I, I'm kindain the same boat where like I
always feel like I need a goal.
(03:48):
And yet when I look around atlike, okay, what's the one.
Big ass thing that Ihaven't, I haven't thrown
a dart at and hit yet.
There isn't one, right?
I can do bigger versions of someof the stuff I've already done.
I could have more of some ofthe stuff I've already done,
but there are very few thingsleft in life other than learning
how to make all of the Othellopieces flip over just by
(04:09):
passing my hand over like thecommercial promise in 1984.
That I haven't done.
No, I get it.
So, so, okay.
Let's talk about what were thesegoals supposed to accomplish?
Okay.
So I wanna zoom out.
I wanna zoom out and I wannasay 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 havethese, these big milestones
that we want to accomplish.
(04:30):
A lot of times we starta startup to accomplish
some of those goals.
Yep.
I, I gotta say, earlyin my life, my goals
were super simple.
Like my goals were like, sobasic 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 currentcircumstances.
Yeah, yeah.
My methodology of whatthat meant, just meant
(04:52):
show up at work today.
Get paid $5 an hour and eatwith that $5 an hour, and I
was perfectly fine with that.
I, I wanna isolate that momentfor a second because I think
people think entrepreneursalways have big visions of
what they wanted to becomein the world and like they
just, you know, what workedso hard to make it happen.
Survival.
Yeah, not so much.
(05:13):
There are many points in, inmany people's lives where their
expectations, and this is a bigpart, where their expectations
are wildly tempered, right?
So our goals are oftena reflection of our,
our, our expectations.
Right.
Ryan, I'm guessing you don'thave a goal to play professional
soccer, nor do I have a goalto play professional football,
(05:35):
like they're tempered by whatwe think our realities are.
Yeah.
Now.
Both of both of my kneesagree with this decision.
By the way,
what's wild about what we do fora living though within startups
is we know we have the abilityto do exponential things, right?
Yep.
Like we could create the nextShopify or Spotify, right?
Like that actually is possible.
(05:56):
Not likely statistically,but it is possible.
Set these goals of everybodylistening right now, that
building a startup has a goal.
That's his big honking goal.
However, what if you, whatif you could fast forward
to that goal right now?
Be at that goal.
Yeah.
How sure of you?
That life would bedramatically different.
Yeah.
This is where it gets wonky,
right?
This is where it gets wonky.
(06:16):
I mean, we did, we did a fullepisode on this, like kinda
like play testing your dreams.
Remember we talked aboutlike, well, like just if you
wanna, you think you wannaretire at 50, play, test it
for three or four weeks at 40.
Yeah.
And, and see if it'sreally what you want.
Right?
Like we talked about,like, I wanted to go
fishing, move to Florida.
It's like I couldfish every day.
I can't.
I can fish two daysa week maximum.
Bought myself a kayak,was like, I'll bet the
(06:37):
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 startdown these paths, sometimes
you realize that like thegoal that you set at the
beginning gets recalibrated.
As you start to achieve thestuff that happens along the
way, one of two things happens.
You realize.
I actually don'tneed that thing.
Or you realize the effortto get to that next thing
(06:58):
is significantly higher thanwhat it took me to get here.
And therefore the, theROI on, it's not gonna
be what I thought.
I won't go after it.
I've always said for a long timethat 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 thatbecause whenever I didn't
have something, I placedso much value on it.
And let me give you kindof different dynamics
(07:19):
that could play into this.
If you're in a really badrelationship, personal
relationship with your spouse,then in your mind, that
relationship being fixed orreplacing with another one
that you know isn't terribleis gonna make you so much
happier, and you're gonna beso much a different person.
If you don't have money, youhave all these, you know, past
due bills and woes, et cetera.
When you have money,you'll be fine.
(07:39):
Yeah, the list goeson and on and on.
It creates a trap for us, andthis is the part that it took
me 30 years to figure out.
It creates a trap where we canconveniently believe that if we
have something we don't have,that we will be fundamentally
different on the other side.
What we never getour heads around is.
If I have been an assholebefore money, I'll likely still
(08:01):
be an asshole after money.
Yeah, yeah.
Yep.
Or you know, orwhatever your thing is.
If you are the person thatalways got in fights in your
relationship, when you findyour next relationship, you're
probably still the personthat always gets in fights.
You're just now getting infights with someone else.
Someone else.
Yep.
Yep.
Well, I haven't had nearlyas many fights with this
person 'cause we haven't beentogether for nearly as long.
(08:21):
Exactly.
Right.
Yeah.
So I wanna start by, bytalking about how we kind
of sensationalize theother side of these goals
without having a real goodunderstanding of whether or
not getting to that goal isreally gonna change anything.
Yeah.
Because in my experience,having gone after a gazillion
goals, I would say, I'm makingthis up 10% of the time.
(08:43):
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 versuswhat you expected.
Right?
If 10% of the time the goalswere worth it, would you
say 10% of the time it wasexactly what you expected?
Like, I got this thing,now I feel this much better
about life, and it's exactlyhow I expected it to go.
I would say in most cases, mostcases, the joy of accomplishing
(09:08):
that goal was so insanelyshort lived, comparative
to the work it took to getthere, that it was like.
What the hell, man?
And, and, and again, I thinkwhen people consider, you know,
I want to have these big goals.
My startup has these biggoals, but I wanna make, I
wanna make my startup huge.
Do you Right?
Like, do you actually know thatthat's gonna work out for you?
(09:30):
It usually does not.
Right, right.
Usually miserable bythe time you get there.
Where I was most surprised inlife, and this is, you know,
again, all mapping back togoals was, was how often I
would set goals that I'd workinsanely hard to accomplish.
I'd get, I'd get the trophy,the thing, whatever it is I was
trying to get to, and the amountof value it drove to me was.
(09:52):
Freakishly low.
Yeah.
It's your point.
The value of something is, isthe fact that you don't have it.
We were talking about a groupof 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 somebodyposed a question, well, like,
well, as you're thinking throughthat, like what are the most
rapidly depreciating assets?
And I jokingly,immediately responded.
(10:13):
I was like, mine.
Right?
Basically meaning that like onceI have it right, like, and now
that's not entirely true, right?
If you're talking about purelymonetary standpoint Sure.
Owning piece of realestate, whatever.
Yeah.
It, it has, it has continuedvalue to some degree, but to
your point, like the reasonwe set the goal in the first
place and then we set out toaccomplish it, the importance
of that tends to diminish.
Kind of the minute we, wehit it, and particularly
(10:35):
founders as a group.
I don't know if there's anybodythat's maybe professional
athletes or the people likethat where it's like, the minute
I have a Super Bowl ring, theonly 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 accomplishit, we replace it with
another like that.
But the longevity ofthe benefit is way less
(10:56):
than we think it is now.
Now lemme giveyou some examples.
So someone will say, well,if you sold your company for
a hundred million dollarsand you've took 20 million
off the table, let that 20million lasts you forever
and longevity's forever.
So your argument'sbullshit, not exactly, yes.
Numerically themoney's in the bank.
I get that.
Yep.
What you're missing whenyou say that is you think.
You are going to be okay.
(11:17):
And here's what everybody willsay, and I, and I get this
argument except that it windsup being wrong and they say,
well, look, I have a bunch ofstuff I can't afford right now.
Right?
I can't afford mortgage orto be to buy a house anymore.
Yeah.
I can't afford you name it.
And when I have money, whenstartup 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 missingis once you've done that,
(11:40):
you picture yourself in ahead space, in an emotional
space, a a feeling of of,of being fulfilled that
rarely ever comes true.
And Ryan, you and I have talkedabout this in other podcasts
where founders sell theirbusiness and they think that
all these things are gonna comewith the sale of their business.
Yeah, yeah,
yeah.
And
it actually makes it worse.
Yeah.
Which is reallyinteresting to me,
right?
I sold my businessand my identity.
(12:01):
Yeah.
I sold my, my businessand all my daily routines.
I sold my business and all myfriends and the people that
I talk to every day, right?
Like all of these things wentout the door with it, right?
And now you're sitting therewith money in the bank and
an absolute identity crisisand no idea what to do next.
Right?
And look, I mean, I, again,if you have the choice between
being broke with an identitycrisis and rich with an identity
crisis, I recommend this.
(12:23):
Easier rich
money for sure.
You always give it away.
However, what I'm trying to toto get at when we're talking
about what our goals we'resupposed to accomplish is
that we set these goals witha bit of a false premise.
We set these goals with anidea that once I achieve goal,
more things will change, andmore importantly, sustain than
I ever thought they would.
Okay, so let's assume.
(12:44):
You know, we can say a, okay,maybe that's true, but there's
another side of it too, whichis 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, whenI was young, so long ago, Jesus,
back in the nineties when I wasyoung, I had this dream like I
think a lot of people did backthen, and probably whatever
(13:04):
the equivalent is now, that oneday 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, thatwas the target, but
it was definitely a BMW three
series.
Yeah.
And in my mind, 'cause Iwas 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 itin it's a heyday.
(13:26):
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 thingI could, could afford.
Yeah.
For a short period of time, itwould melt off as time would go.
And it was so bad that whenI drove it to the dealership
to trade it in for a whiteBMW three series, that it
(13:47):
actually, the car shut off.
Like I'm just drivingit and the car just shut
off while I'm driving it.
Yeah.
Not, not dangerous at all.
And I coasted intothe dealership.
And parked it, got outand handed them the keys.
Like that's
on one hand you have to, I, Iwould love to have known what
was going through the salesperson's head at that point.
'cause on one hand they're like,this guy definitely needs a car.
(14:08):
Yet, you can't
leave without one.
And
yet, based on how hearrived, is he actually
gonna be able to buy one?
You bet.
And so, so I'll never forgetthis moment of pulling out
of the dealership in a whitethree series BMW and Ryan,
I was, I was over the moon.
I thought I had won it lifeand everything was gonna
be perfect thereafter.
(14:28):
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 perfectkind of, um, microcosm
of what I would startto learn about goals.
(14:48):
Goals are really valuableuntil you get them.
Then on the other side ofit, 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 referencedhim before on the podcast.
Uh, David MeyerHansen from Base Camp.
Yeah.
David's like crazy car guy.
And I remember like back inthe day he had like a $700,000.
(15:09):
Punani or whatever it was.
I mean, like he's, he'sway, way in the car.
He's a massive carcollection, whatever.
I was talking to him aboutthis and he said, I think
the three Sears, BM BMWwas 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 mein his Danish accent, he's, I'm
not gonna try to replicate it.
He's like, well, buying that, Ithink, I think it was a Porsche.
(15:30):
He's like, buying that Porsche.
Gave me 90% of thesatisfaction that I would
ever get from buying a car.
He's like, I triedeverything afterward, right?
Like, like, his carcollection is sick.
He's like, but it never,nothing ever even came close.
To the satisfaction ofgetting that first car.
(15:50):
And basically, basically what hewas saying, and I felt the same
way, is that BMW gave me 90% ofthe satisfaction I'd ever get.
Yeah.
From getting to that goalbecause 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 evengave me 10% the value of the
satisfaction, which is funny.
(16:10):
Because the increment ofdopamine becomes significantly
smaller, the increment of costto go up to those higher levels
becomes significantly higher.
Right?
Well, you're paying moreand more money to receive
less and less joy, whateveroutcome that you wanted.
But there's another side.
Yes, a hundred percent.
But Ryan, there'sanother side of it.
(16:31):
This is, this is what messedwith me and has messed
with me ever since and it'sprobably 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 ortwo later I went out and I
bought like a, a Lamborghiniand I was like, oh my God.
Like it doesn't getbetter than this.
And it was awesome.
Yeah.
For like 24 hours.
And then I realized that the,the amount of time, effort,
(16:52):
cost, whatever you'd attachto increasing the goal didn't
have anywhere near the payoff.
And here's, here's what'sinteresting, which made me
not want to do it, right.
It's kinda like Tom Bradysaying, 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'swhat Tom Brady does.
I don't really wannado this anymore.
'cause it's, it'skilling my body.
(17:13):
Right?
Yeah.
I, I don't need the money.
Right.
Blah, blah, blah.
I think something interestinghappens when you accomplish
some of these goals and yourealize 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 aninteresting and dangerous
curve to be on, right?
Because depending onwhen it happens, like so
what if we're like, yeah.
(17:33):
You know, actually hitting ahundred thousand an MRR for
the business probably won'tbring that much more joy.
Fuck it.
I'm just not gonna, I'mnot gonna move and look.
That might be absolutely fine.
I think it depends on whatyou set out to accomplish.
Why, you know, doyou have investors?
Do you have a big teamthat's all, all expecting
you to do these things?
Did you make those promises?
If you didn't, then I think it'sokay to reconsider these things.
(17:54):
But it is interesting becauseI think that like I. Early
on, I think there were someimportant milestones that
kind of needed to be hit you.
You talked aboutit a little bit.
It was kinda like the onesthat are, you know, safety
or, or survival more sothan just, I want a thing.
And so I think that thereare a number of those that
once you've accomplishedthem, there is probably
a longer lasting effect.
And we give credit to,like some of my early
(18:15):
goals on accomplishing themdid three things for me.
One, they gave me theimmediate whatever it was.
Right.
So like sold, the firstcompany got cash, right?
Yeah.
Yeah.
Right.
Cool.
Right.
Got cash.
Now that cashdoesn't last forever.
Dopamine hit of achieving thatthing of, of, you know, building
a business that doesn't last.
Right.
Whatever.
What did last I. Was abit of a safety net that
(18:37):
came from that, right?
Which allowed me tomake different decisions
going forward that thatdid last to some degree.
The other thing that lasted wasthe memory that I could do that.
Right.
Agreed.
And that that was an asset thatI definitely carried forward.
It's like once you'veaccomplished something, you
know you're capable of it.
It sets a new save pointfor you and you can kind of
continue to build up from there.
So I think that's onethat we, we lose, but.
I also didn't need tosell five companies to
(18:59):
know that I could do that.
Right.
One was enough.
Well, let's, let's build onthat a little bit because
I, I think there's someimportant points in there.
The first thing I wanna pointout is that there are, I see
two different goal paths, ifyou will, for, for everyone.
One is what I consider thepleasure and lavish path when
people are like, oh, he buysa hundred thousand dollars
BMW, kind of thing, right?
Like, that's just, youknow, pure pleasure.
(19:20):
But the other pathis around pain.
The avoidance of pain.
Okay.
Can't pay my bills, can'tmake, you know, can't do a
doctor visit, you know, thingslike, can't feed my family.
Kind of.
It's, dude, it's, it's eat.
Eat caviar.
Right.
And so I think initiallymost of us are just
trying to avoid pain.
Right?
And, and the truth is,for most of the world,
(19:42):
pain is the baseline.
Sure.
There, there's a significantamount of pain and,
and relieving that painvis-a-vis security.
Is our number one goal, and thatis an incredibly important goal.
No question about it.
However, for thosefolks, let's talk again.
Founders, that's our world.
For those folks that achieveit initially, they're so
distracted by that painthat they just assume that
(20:02):
when that pain goes away,that they will be happy and
satisfied and all these things.
Yeah, yeah, yeah.
Here's what'sreally interesting.
Rarely happens.
It rarely happens.
The difference is theyjust 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 painthat we then feel like
we have to go solve.
I've watched this overand over, particularly
(20:23):
with founders, right?
Because we're so used tocommanding our destinies.
Yeah.
And so it throws us whenwe command our destinies,
get what we want.
And then don't have theresults we expected Uhhuh
this podcast.
And so one of the interestingthings I've found is that when
you are in pain, um, now I'mgonna use physical, actual pain.
Sure.
Right?
You've hurt something, you'vehad a chronic condition.
(20:43):
I've had a chroniccondition that is
egregious amounts of pain.
At the time, all you wanna do isget 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'vefound a point where we got
on the other side of it, onceyou've removed pain, it doesn't
necessarily make you happy.
It just makes you relievedthat you don't have pain.
(21:04):
See, it's different, right?
People think like, oh, I'min a bad relationship with
my spouse, and so if, if wejust break up or, you know,
settle or whatever, that allof a sudden I'll be happy.
No, you just won't have pain.
It's not the sameas you'll be happy.
It's
the difference betweenrunning from something and
running towards something.
Correct.
And so a lot of our goals areabout relieving pain initially.
And I would argue thatlike phenomenal goal.
(21:27):
Yeah.
But once you've relievedpain, right, and now you're
just looking at it strictlyfrom the standpoint of, of
how do I increase pleasure,happiness, you know, uh,
whatever you call it.
That's where it starts toget a little gnarly because
it's actually way harderto do than people think.
A lot of people think if Ihave more money, I'll just
be able to have more freetime, be able to, to go on
more vacations, et cetera.
(21:47):
It doesn't work like that.
You know something that'sreally funny about everything
we talk about here isthat none of it is new.
Everything you're dealingwith right now has been done a
thousand times before you, whichmeans the answer already exists.
You may just not know it.
But that's okay.
That's kind of whatwe're here to do.
We talk about this stuff onthe show, but we actually
(22:08):
solve these problems alldayLong@groups.startups.com.
So if any of this soundsfamiliar, stop guessing
about what to do, let us justgive 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, asyou're talking through this,
(22:29):
I started to think about it injust slightly different terms.
And came to a realizationthat at both ends of the
spectrum, right, whetherwe're talking these like early
goals or later goals, there'san existential component to
both, at least in my case.
Yeah.
Yeah.
The first goals were like, getto that safety baseline, right?
Existential in thesense of like, how do
I continue to exist?
(22:49):
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 avery different level.
Oh right.
Yeah, yeah.
But what was crazy was like,I don't really remember
there being a transitionpoint between those.
Like I ergo I didn'tunderstand, I'm now safe.
I can now just focuson these kind of like
more cerebral things.
I can, I can be morefocused on the the why.
(23:11):
And I guess one of thebig questions is like.
Some point why are we stillchasing, which I, we've, we've
answered in a lot of differentways today, and we've talked
about other podcasts, but Ithink that was an interesting
realization for me is thatthey were both existential
just at kind of differentends of that spectrum.
And I'm not really sure howI'm gonna reconcile this now.
Can't land this plane.
Well,
let me build onthis a little bit.
So one we have, again, we'retrying to get rid of pain.
(23:34):
In, in, in whateverforms that affects us.
And let's say we do that, uh,we get, we get rid of pain.
The absence of pain isnot pleasure, it's just
the absence of pain.
And I think that's a, that'sa, when you're in pain,
like literally you and Ihave 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 aneutral, I'll be fine.
(23:54):
I'll be greatt.
You bet.
You bet.
But for folks, you know, let'stake 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 absenceof pain, but that is not
the same as happiness.
No, not at all.
That's at all, and that'swhat really messes with us.
Okay.
Yeah, but let me zoomout a little bit further.
(24:16):
The idea is that once we hitwhatever those milestones
are, let's, let's saywe've already made it past
the video game level thatis getting out of pain.
Yep.
And now we're just tryingto maximize for pleasure,
enjoyment, happiness,fulfillment, et cetera.
Those milestones, thosegoals, if you will, are
really hard to come by.
Really hard to come by.
Yeah.
Yeah.
And one of the trickythings about them is that
(24:39):
you can quickly realizethat more effort actually
doesn't buy you anything.
Let, let me build on that.
Hence, hence where I'mat right now in life.
Okay.
Right now, buying another carI already know is not gonna
gimme any more fulfillment.
Right.
As you know, I drive apickup truck, uh, and,
and I tend to, yeah.
What's in the shop, but yes.
But like buying anothercar isn't gonna do that.
(25:00):
More vacations isn't goingto make me more happy.
Right.
Right.
For me, building things likecreating things makes me happy.
But one of the things that'sreally messed with me, Ryan,
over the past year or two,is for the first time in my
life, it's like I know betterthat yes, I can put myself
on some ridiculous goal.
Yeah.
And it kind of sucks to know.
(25:21):
Yeah.
Yeah.
That I already knowit's not gonna work.
Yeah.
Look, I think there's thissense that as we go from
feed me to fulfill me, thatit becomes significantly
di more difficult, right?
Like we're climbing this,the pyramid of Maslow's
hierarchy of needs and likewe get to self-actualization,
which is where you're at.
Yeah.
And then all of a sudden werealize like I. Someone's
(25:41):
kind of fucking flat, right?
And, um, the view from hereis basically the same as, so
I think, you know, for me,as, as we're talking through
this, I'm realizing that insome of my most successful
goals, and I don't meanthat in terms of the size of
the outcome, anything else.
Yeah.
I was as satisfied by thechase of the goal, right?
So the accomplishment.
(26:02):
Was satisfactory, but I,I need to go back and kind
of do some calculus on whatwas it that made me engaged
throughout the process.
Right?
So I wasn't simply doing itbecause of the end point, but
like truly like the, the, theentire pathway was something
that I wanted to be able to do.
I go back to thingslike coaching.
Hannah's first soccer team.
We won the league thatyear by leaps and bounds.
(26:23):
That's not the part thatwas like the coolest for me.
The coolest part for me was likethe individual little moments
of like that kid that had neverscored 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 arethese things along the way?
Right?
Can we find fulfillmentin, and of course we've
all heard this, right?
You gotta, you have to enjoy thejourney, not the destination.
(26:44):
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 onthat as an aside, I'm gonna
tangent for a half second.
I can't stand when rich peoplegive rich people advice.
Um, right.
Like these platitudes, becauseI'm like, I always put an
(27:05):
asterisk at the end of theirquote 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 expressionthey make after they finish.
It's the smug looksays if you're rich.
Yeah.
Yeah.
And, and it's, it's like,Hey, great advice from
you, rich guy, because thatnow applies to you, right?
Yeah.
Like money isn't everything.
If you're rich, if you have it.
Yeah.
Like you already have it.
(27:26):
Yeah.
Um, try not having it.
I never felt that way.
Right.
But, but my, but what I wasgonna say is what's been
interesting to me about, youknow, kind of chase the journey,
enjoy the journey, et cetera.
It is true, but I wouldsay this a bit different.
The journey is very differentif 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?
(27:47):
Oh, well, I mean,there's the question.
I'll leave it like this.
Um, when someone says, youshould really enjoy the journey,
dude, when I didn't know if Iwas gonna be able to eat at the
end of the week, there's no partof me that was like, I'm not
talking about the existential
fee.
I'm not talking aboutthe feed me side.
I'm, I'm, I'msaying we're, we've.
You said we were past.
We were past
those, right?
We
were
Oh, that that's whenyou've already won.
If you're optimizingfor pleasure, right.
(28:09):
If you're saying, you know,I wanna go from a hundred
thousand dollars car toquarter million dollar car,
then you can say dumb shit.
Like enjoy the journey.
Right, because you'vealready won, right?
You're already
driving the white BMW.
Yeah, right, exactly.
The ride's already fine.
Like
I just, my frustration, andI try to be mindful of this
coming out of my mouth as well,is saying using platitudes,
like enjoy the journey withlike, almost like complete.
(28:32):
Like disassociation fromwhat people in the journey
are actually The reality.
The reality.
Yeah.
Right.
Reality.
Their experience.
They're like, enjoy thejourney of not making
payroll again this week.
Which part of that is fun?
Logging into gusto andseeing 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 theoutcome of being fired.
(28:52):
Enjoy the journey.
By which I mean pack youup your desk and yeah,
I think about it interms of, you were
mentioning soccer, right?
Yeah.
I think there is a pointwhere you realize that
winning at soccer isn'tgoing to really change your
outcome, but playing soccer.
Is going to be awesome.
I've been trying to, tochange that mentality.
Like it, it's a luxury tohave, if I'm being honest,
(29:15):
to be able to say, if we growstartups.com to a hundred x
what it is now and sell itfor a gazillion dollars, it
literally won't change my life.
And that's not becauseI'm so incredibly rich,
it's because I just don'tactually need anything else.
Yeah.
Right.
Like I just financially,like there's, there's
nothing that I want.
That requires so much cashthat I have to do something
(29:36):
extraordinary to get it.
Now, that's not the sameas saying that like,
my ambition is gone.
It just magically disappeared.
Yeah.
It's saying that for thefirst time in my life,
there's not a a, a materialobject on the other side of
it, which is weird for me.
It is.
I think part of it's justsaying like, look, I don't
have to have, because.
There's nothing that I'mbeing ambitious towards.
(29:56):
It doesn't mean that I'm notstill driven in some way, but
it doesn't necessarily haveto be that same ambition.
I think it's trying toswap fuel sources in
the middle of a drive.
Yeah, right.
It's like, how do I say?
Like, look, I don't haveto be scared anymore.
I don't have to run towardsthings and there's nothing
that I really want so bad,but for some reason, maybe
this is the big question weneed to ask ourselves, but for
some reason I still feel likeI need to want something I,
(30:18):
I need to want to at least.
Look useful.
I want to be in motion.
I want to be productive.
I want those things, butthose things untethered
from a specific goalare hard to achieve.
And so I think this is why wecome back full circle and go.
So I guess I need a goal.
So here, here's whatI've been kind of
discovering, if you will.
Um, I've been discoveringthat for me for the first
(30:39):
time in my life, attachingmy effort to a trophy.
Doesn't buy me anything.
Yeah, it's a weirdthing to say, right?
It's a weird thing tosay, but for example, I
do not want a private jet.
Now I say that to sayprivate jets are wildly
expensive, right?
Like no matter how you doit, no matter how you cut
it, they're wildly expensive.
And for people who have, youknow, great wealth or want
(31:00):
to achieve great wealth, aprivate jet is like part and
parcel to what they want.
I've ridden on privatejets, they terrify me.
They're too small and mywife won't get on one.
Now I'm saying that to say it'snot like we're riding private
jets all the time, and my wifehas these decisions to make.
She's been on a few and she'slike never got into it again.
Point is that's one ofthe biggest like financial
achievements yet it's, and Iactually just don't want it.
(31:21):
It's a signal.
Yeah,
so stick with that.
I don't want a second house.
We did a secondhouse for a decade.
It sucked.
Always felt like we hadto be at the other house.
It was awful.
I, I'm grateful, wildly gratefulthat I had that experience.
Yeah.
But now having had it, Ialso, no, I don't need it.
And again, going back to thecars and everything else, I
am shocked at this point in mylife, actually truly shocked
(31:42):
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 interestingabout, you know, building a home
and, you know, as involved asI've been is it feels like the
last thing I've ever wanted.
And that, that makesme a little bit sad.
(32:03):
I was gonna say, yeah.
That, that, that's probablygonna drive anxiety in
and of itself, right?
Yeah, it's like.
The sense that you're gettingcloser to achieving that thing.
Right.
Which has taken, well, decadeson 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 firsttime we were talking
about this, because you'relooking at the land, you're
starting to do the threerenderings, all that stuff.
(32:23):
Yeah.
It's been a long time ago,half a decade ago, but now
it's like, as you're nearingthe, the, the completion
of that milestone, right.
The achievement of thisone without a next quest.
Feels a bit like idlingand neutral, right?
Like engine rev,nowhere to roll.
Like we're not good at this.
Yeah.
Well that's a Ryan, that'sa great way to put it.
Like I wasn't built fornot achieving goals and yet
(32:47):
at the same time I'm in aplace where I know that just
creating more goals for thesake of creating more goals is
kind of a bullshit exercise.
Yep.
So kind of what I'm sayingis I'm trying to learn.
To do the things that Ienjoy, not because I get
a trophy, but because Ireally enjoy doing them.
I'll give you an example.
Wait a minute.
Are you back toenjoying the journey?
(33:08):
Will?
No.
No.
I'm not gonna enjoy the journey.
No, I'm kidding.
Like for example, I play, youknow, hockey with buddies.
You've been,
but that's actuallya 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, guysthat I was on the job site
with, we were buildingour house, uh, last week.
They were basically saying,um, aren't you really excited?
(33:29):
You know when this house isgonna 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 workingon this thing forever.
But number two, I said, thewhole point of doing this was to
build it, to actually physicallylearn how to build things.
Yeah.
To here to do it.
Build cabinets, learnhow to do architecture,
learn how to do all thesethings myself, and having
a big honking, like wildlyoverwhelming goal, which is.
(33:52):
The nature of what we do asfounders in knowing that I
could like count on myself tobuild it with my bare hands.
I mean, I think, and, and Idon't wanna be sexist here,
but like as a dude, likeprovide shelter for family.
Yeah.
Like, like something verynear and dear to who,
you know, my identity.
I'll be there to make the firethe day you open the place.
Well, I'll handlethat side of it.
Exactly.
Gave in though, so.
(34:12):
No, but my point is, I thinkwhat's been interesting about
it is the folks I was talkingto 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 buildingthis 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 createsomething from scratch
that felt like a pen.
Ultimate moment in my life.
(34:34):
Yeah.
Kind of like, like a, here'sa great way to say it, as
it felt like the resultof 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'sgot a very like cathartic.
Milestone.
You know what it is, Ryan?
Sure.
It's something that says, Heydude, mission accomplished.
You're good.
And I haven't had amission accomplished.
(34:56):
You're good in 31years in my career.
I now we're, we're justdefinitely gotta be a
follow up episode on this.
Uh, once, once you wake upin jammies in that house and
we have to go, okay, so didthe dopamine last more than,
more than 48 hours, right.
Or now that you'vegot it, it won't.
Right.
We, we sort of know it won't,
but, but stick with thatbecause, and again, and, and
if folks are listening tothis that, you know, I'm, I'm,
(35:18):
I'm trying to be open aboutmy feelings and my thought
process so you can kind ofjust see what's in my head.
I already know that like,hey, you know, once you get
the keys to the three seriesBMW and you drive it off the
lot that the value, you know,uh, not just financially but
emotionally plummets, it's notthat, it's knowing that I'm not
going to need a bigger house.
Right, right.
Um, and if I do, I wouldlove to find out what the
use case for that one is.
(35:41):
Will, has been banned fromdriving in all 50 states, so he
had to build a house big enoughthat he can drive around inside.
So that's kinda off the table.
Said differently too.
Like, you know, my kids willleave 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 ofknow this is as much
houses we'll ever need.
And with that, there's agreat calming feeling to that.
Like a finality to it.
(36:03):
Right?
Like, like feeling likeyou've, you've gotten to the
end of an important journey.
But also, here's what'sinteresting, 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 thethings that people buy with
a bunch of money, I don'twant any of that stuff.
Yeah.
Like my, my big purchasesright now have to do with
(36:24):
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'msaying is as, as, as folks
are thinking through theircareers, their progressions, as
founders, we rarely think about.
What does the endgame look like?
Is part of the, the, of ameasure of success, if you will,
(36:44):
the lack of needing more things.
Right Now you could get realBuddhist 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 thenit, it goes from being like, we
go from playing like really biggames with really big trophies.
Yeah.
To micro games orinfinite games.
Yep.
Right.
I think that's kind of wherelike it's, it's funny, like as
I've been really unpacking thedecision to move to Madrid, I.
(37:06):
For me, like we've gota lot of reasons for the
kids, the family overall.
Like there's a lot ofreasons we wanna do this.
As I've been looking at the oneswhere 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 hardto make this happen, right?
And so why, why am Iactually doing this?
And I think part of thatwas that I feel like it
will help me with someof those infinite games.
(37:26):
At some point I be like, this,this is like, why a lot of
people turn to philanthropyat some point, right?
They're like, well, I haveall the stuff I need, so now
I'm, I'm just going to becomea, uh, a philanthropist.
I almost said philander.
That was not what I meant.
I, I literally almostsaid philander.
Uh, so, and, and what do Imean by like the infinite game?
So it's, it's things like.
Mentorship or creative crafts,legacy projects, like continuing
(37:48):
to play to play soccer, likethere is a, there's an end
point for that right there.
There is definitely a pointat which I can no longer
continue that pursuitbecause 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'tnecessarily have.
The same kind of outcome, right?
Like mentorship, for example,right there, there will always
be someone new to mentor orthe, the, the mentee will
always have elevated goal.
(38:10):
Like, they'll be in the samesituation where like, well,
it'll help them accomplishtheir goals, but like for you,
for the house, you've said thisbefore, it's like you're gonna
spend, you know, it took you50 years to build it and you're
gonna spend the next 50, like,tinkering with it and, and
adding onto it and doing allthis stuff around it, right?
Yep.
So I think.
To me, that's kind ofwhat it turns into.
It becomes the infinitegames where we specifically
design them so thatthere is no end point.
So we can just keep playing.
(38:31):
Okay.
So, so stick withthat for a second.
The, just keep playing.
I always use Tom Brady as anexample 'cause he just to, to
me he just seems like such likea pent, ultimate success story.
Again, I don't know theguy, he might be a, a giant
ass, but point is, there'sa 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 winninga Super Bowl, but you know,
I just like passing theball around in the backyard.
(38:52):
To my kid or with myfriends, and I just enjoy
the game of playing football.
I don't need to winSuper Bowls to do it.
I just want to enjoy what it is.
Ryan is how I feel aboutour jobs@startups.com.
startups.com becomes ahundred times bigger.
I honestly don't, don'tknow that it changes
our lives whatsoever.
To a large degree.
I hope it wouldn't, right?
Yeah.
Right.
I love what we do, right?
(39:13):
I wanna keep, Iwanna keep doing it.
Like to the extent that if itbecame a hundred times larger
and it meant that we didn't getto do some of the things that we
do now, I would not want that.
In fact,
we're not going out of ourway to keep it small either.
Right.
The point is, we're at a pointwhere we already get to do the
things that we enjoy the most.
Would that improve a fewthings in the future?
Of course it would.
But the idea being, we'reenjoying what we get to
(39:33):
now, but this is, this isthe equivalent of us as Tom
Brady in the backyard, justthrowing the ball around.
Just 'cause we actually.
Enjoy it.
If I were to think about anevolution of goals, right?
My thought is this, ideallyeveryone listening achieves
all of their goals.
I'd sincerely hope that happensand when it does, and when you
get to that point where you'veachieved so many things in life
that you've wanted to achieve,I hope you get to the point
(39:55):
that I know I'm working on,working through right now and,
and rhina, you know, I'd liketo believe you are too, that
at some point you say, my goal.
Is to be able to do the thingsI love without consequence,
without goal, without somethingthat prevents me from not doing
it or not doing it for thewrong reasons, not doing it
'cause I get a car at the endof it, doing it because I just
love being covered in sawdust.
(40:16):
Building something that neverexisted before, or spending
time with someone that Ilove while I'm doing it.
And being able to just createfor the sake of creating.
I think yes, we mightrun our goals, but we'll
never run a, the passionthat gets us to our goals.
And I think that kind of passionis what we need to develop
if we're gonna be able todo this pretty much forever.
I. Overthinking your startupbecause you're going it alone.
(40:38):
You don't have to, and honestly,you shouldn't because instead,
you can learn directly frompeers who've been in your shoes.
Connect with bootstrapfounders and the advisors
helping them win in thestartups.com community.
Check out the startups.comcommunity@www.startups.com
to see if it's for you.
Could be just thething you need.
I hope to see you inside.
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