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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to the episode of
the Startup Therapy Podcast.
This is Ryan Rutan joined
as always by my friend,
the founder, and CEO of
startups.com will schroeder.
Well, startups are like the
only place where you cross the
finish line and immediately
get handed a new race bib
for the next marathon.
And are the starter pistol fires
Uhhuh.
My English isn't English today.
You close the round, you're
already raising the next one.
You hit the milestone,
it resets to zero.
So will in, in 30 years of, of
startups, how, uh, how often
do you complete something?
Dude, I'm still waiting
to complete something.
Like, I feel like
it's, it's weird to me.
Yeah.
It's weird to me that we've all
gravitated toward an industry
that doesn't really ever end.
Yeah.
Because I think, yeah.
I think about like regular
people with regular like,
like reasonable people.
Let's not call 'em
regular reasonable people.
Reasonable people.
Yeah.
Reasonable people
with a reasonable job.
Their life looks
something like this.
They wake up in the morning,
they have a place to be,
let's say their job, right?
Sure.
They show up, they do
their work, they go home,
they forget about work.
Uhhuh, hopefully, right?
And then on Friday
they get paid.
That is a very reasonable
pace and it makes you feel
like he got something done.
It makes you feel like
good to go on vacation.
It makes you feel like when you
go home, it's just done, man.
Just done.
But we're in a business where
no matter how well we do,
all it does is set us up for
a much bigger problem next.
Right?
Like if we hire one person,
we got 10 more problems.
If, if we launch one
more product, we got
10 more problems.
Yeah.
It's endless, man.
It just never ends.
Yeah.
Yeah.
You know, it's funny, I, I
think that part of it for
me was realizing that there
was, the, the trap wasn't
that we set goals, right?
Of course, we need goals.
We have to have something that
we're actually aiming towards.
It was that we expected the
goals to deliver fulfillment.
Instead of just progress.
Right, right,
right.
I think that was the challenge
for me was that it was like I
expected there to be this sense
of completion or this sense
of fulfillment when instead it
was just, yeah, it's another,
it's another goal complete.
It's another milestone.
And startups just kind of
tend to be infinite games.
Right.
And treating them like,
yes,
finite games kind of
guarantees disappointment.
Well, so that's what I was
hoping to unpack today.
I, I wanna talk about like, how
do we deal with no completion?
No lack of, of an end game.
And if you're new to
this, if you're new to
the startup game, you are
gonna learn this very well.
You're gonna learn that
no matter how much you do.
Yeah.
There's 10 more
things to replace it.
It's not just whack-a-mole.
Yeah.
It's you, you hit the mole
and 10 more machines show up.
That's it.
With a whole bunch
of moles to whack.
Right?
Like it's a bit maddening.
Yeah, and I think there's,
there's some broken psychology
that's at the, the base of
this that, you know, again,
I, I kind of wanna unpack.
The first thing that I
learned about a long time
ago was something called
the arrival fallacy.
Yeah.
Yeah.
And the arrival fallacy
works like this.
The arrival fallacy works
like I always believe.
That if I just get to this
insert next step here.
Yep.
That everything will be fine.
Everything else is
good after that,
and then every time
I do it just resets.
Yeah.
Right.
Over and over.
And for a lot of founders, this
is literally how our lives go.
If we just get this pre-seed
round, we'll be good.
Right?
Everything will be fine.
We just make payroll.
Everything will be fine.
And yet, 10 years later, right?
It's still going
through the same thing.
Yeah, that's exactly it, man.
It's like every arrival is
just a, a costume change
for the next party, right?
Like Right,
right, right.
That's
all that's happening.
Right.
It just, the goal moves.
It might change
completely, right?
Like, oh, the funding
round is the thing.
Well, okay, yeah.
Now that we've got the
funds, well now we actually
have to grow a business.
Now we have to go hire
a bunch of people.
Now we have to do whatever.
Yeah.
I think it's when we start
to conflate milestones
with meaning as opposed to
them just being markers.
Right.
And that like, yes,
they're, they're necessary.
Yes, we have to achieve these
things, but I think we put.
Too much weight on the, the
achievement of them or sort of
what it's gonna mean to us, or
that there's for sure, for sure.
There's nothing
after that, right?
That's, that's the
real, the real problem.
Your happiness depends
on the next milestone.
Your happiness has a
subscription model, right?
So you're just, you're
gonna keep consuming, man.
You're never gonna cancel.
But it's not the way this
process is built, which I
think is, is interesting.
There was a great, great
onion article, like this
is like 20 plus years ago.
Okay.
Okay.
And this is like toward
the end of the.com boom.
And it said something to the
effect of Michael Delta's staff.
We became the number one
computer manufacturer.
We're done.
Everyone go home.
Right.
Right.
It's like, and so
the article, right?
It was, it was such
a great article.
In the article.
It's basically him saying, look,
when we set out to build this
company, I set out to build
a number one PC manufacturer.
Right?
And he's like, and we did it.
Now everybody can go home.
Right?
It like, like, like it
was a perfect example of
how this is never done.
Yes.
And I'll never forget
that the image they had,
like the photo they had
was of two guys carrying
out the ping pong tables.
Like, we don't
need these anymore.
Right.
Perfect.
It was incredible.
No, this is, those are
the take home prices, man.
We don't, we don't need this.
But, but think about that.
Like we don't get the
benefit that most people
get of being done.
Yeah.
Ever.
No, no.
We don't get the
benefits any of them.
Like it just the rest
that comes from it.
But like, look, even at
just a very basic level,
our brains get dopamine
hits for completing things.
Yep.
Startups are built to deny
completion, and that mismatch
for at least, like in my
case, I certainly in your
case, it creates this sense
of chronic restlessness.
Right.
That's why we're
always on the move.
Even when we're sitting
down, we're like, what's the
next thing I could be doing?
What's the next
thing I'd be doing?
What's the next
thing I'd be doing?
What was the most
painful arrival?
In your 30 years where you
got there and you were like,
yeah, this is the one that,
that didn't actually land.
I, I would say this is as
equally sad as it is painful.
Okay.
When I was in college and
I remember plain as day,
I remember that if I could
just make enough money to
cover rent, utilities, I
didn't even have a car.
Rent, utilities, and food,
which by the way, collectively,
collectively, was $500.
Wait every month.
Every month.
Not daily.
Every month.
Yeah.
My whole cost of living to
live as a human was $500.
Yeah.
In the United States.
Right?
If only.
Anyway, but I remember
thinking that if I could make
that kind of money, like I
would, I would be good to go.
And, and honestly
it took a minute.
Like sure.
It wasn't that fast.
And you know, part of that
too is when you're starting
a business, you're often
losing money on things.
Yeah.
You're not just, you know,
instantly making money.
And so I got there and I was
finally consistently making
more than $500 per month.
And I remember
thinking, I'm good.
Yeah.
Like, like, what else
could possibly happen?
What else could there
be?
Right.
And then within like a
week later, we needed to
hire someone, which by
the way, it was Damon.
Oh, that's
hysterical.
Yeah.
Yeah.
Right.
That's amazing.
I mean, think like
30 years ago, right?
Right.
Now we need, have no
idea what I'm saying.
A thousand dollars.
That's
exactly it.
Uh, so for those of you
listening, uh, Damon, who's
a great guy, a, a good
old friend of ours, I used
to be one of the folks
here@startups.com, so when I was
referring back, I mean, we're
going, yeah, way, way back.
But I remember it like he
came on and like, I think we
needed to pay him a thousand
dollars or something like that.
Oh man.
Per month.
Right.
And I was like, where am I gonna
come up with that kind of money?
Right?
Like, and then it
reset everything.
I'm like, shit, now I'm,
I'm down $500 a month.
Yeah.
That's
right's, right?
I was good.
Right.
And I remember how
incredibly I was like.
Is this gonna happen again?
Yeah.
What, like what about you?
What's like the, the one
thing you thought if you
could just get there?
You know, it's probably
honestly something similar.
Uh, you know, I think it was,
I'm, I'll aim a little later.
Uh, because there was
definitely that like, let's
just make the ends meet, let's
just figure out, right, like
how they, we keep them from
turning the, the electric off.
Because by the way, the
websites we're selling, they're
hosted on a local server
that lives in my living room.
Right.
So if the, if the lights
go out, it's more than
just getting dark in here.
It was post hiring.
Right.
And it was then like being
able to say that like, not
only do we have enough money
to cover payroll, it was
getting to a cushion and I
set a really specific cushion.
I wanted, I wanted
three months of opex.
Yep.
And we worked like crazy to,
to drive enough sales and
like, which drives more costs.
Right.
Did a lot of things.
Then I remember just thinking
like, once we have that
three months of money in
the bank, where I know that
like nothing, anything that
happens, I've got at least a
couple months to figure it out.
That is going to be the thing
that just allows this thing to
go into a bit of cruise control.
Oh, the growth that we went
through to get there, like
that, what allowed us to
bank that cash put us on
a growth trajectory that
just kept things moving.
And so then the, the
payroll grew, right?
And then the, the
opex grew, right?
And so then I'm all
of a sudden I'm like.
90 days worth of opex is now
like 15 days worth of opex.
So what did I do?
We gotta get 90 days again
right back into like, did
I learn from that lesson?
Absolutely not.
Absolutely not.
Let, can we talk about
like where that comes
from a little bit, right?
Yeah.
Why?
So we, we talked about
the fact that like, you
know, the fact that we're
never getting the dopamine
hit at completion creates
this insane restlessness.
And I think that is,
that's one of the drivers.
But then there's this other
one, which is that we're taught
to despise complacency, right?
Yeah.
Like as founders, it's
not, it's not also, okay.
It wasn't okay to just
sit and say like, we
have 90 days of opex.
Now let's just keep operating
at exactly the same level
we're at and never move,
and everything will be fine.
All right.
You are ridiculed Yes.
In this business.
Yes.
And here's why though.
I think because we got into
this business by taking someone
else's lunch who was complacent.
Yeah.
You know, and I, I said, you
know, I told you ear earlier,
the disruptors, the apex
predators of complacency.
Right.
That's
exactly it.
The reason we're in this
business is because someone
else got complacent.
Right.
I think about it like when you
and I grew up in the nineties,
uh, with our businesses, with
the web design businesses,
we watched this happen Yes.
At a massive scale.
What we'd go in, we'd go
in and we'd talk to these
clients, and it was these
40-year-old men, which to me
were like a hundred at the time.
It's funny that they're like
significantly younger than me
now, but like these 40-year-old
men, deer in headlights,
that the internet was coming,
Uhhuh.
I was like, my entire career
and everything that I have
in front of me is based on
the fact that someone like
you got old, fat and happy.
Yep.
And got complacent.
Yep.
And now someone like
us is gonna come in and
eat your lunch for you.
Yes.
Kind of hard to build your
entire career based on that,
not thinking that you're
gonna be the prey next.
Yeah, yeah, that's
exactly right.
That a day goes by.
It's about apex.
It doesn't necessarily know
it's the apex predator, right?
You don't know what's, you
don't know what's hiding
behind you in the shadows.
And I think what's interesting
about that is in our
business where everything
turns over so quickly.
You know, the newest thing
replaces the oldest thing.
We are at the epitome
of it right now with ai.
I mean, it's happening so fast.
Yes.
So fast
that even the leaders
don't understand how
to keep up with it.
Like even Sam Altman
from Open AI Chat, GPT
Yeah.
Is like, we're gonna get
eaten by Gemini or Ina
topic or you know, whatever.
And he is like, dude, even
that guy's got the problem.
Right.
And it's his product
that's eating everybody
else's lunch, right?
Like
Yep.
Tells you something.
It's crazy.
And so I, I think we've
got two things happening
at the same time.
One is that we're yearning for
an endpoint, a chapter save,
like a a, a, finished, we
want that dopamine hit.
Yep.
Right.
Right.
And we keep thinking it's
gonna happen, which is,
which starts to build
this compounding anxiety.
At the same time, we're like,
okay, well maybe I'll take a
beat and celebrate the winning
and, and enjoy the moment and
just be glad we're where we are.
Yeah.
And we are constantly
reminded you do that and
the person behind you
is gonna eat your lunch.
It's, it's not a great
recipe for relaxing.
It's not right.
It, it, it can kind of get,
it can kind of get thrown in.
Like, it looks a little bit like
ambition, but I'd argue it's
just paranoia dressed as virtue.
Right.
Like we don't.
We don't have to do that
to ourselves, but we do.
Right.
Virtue.
I love that.
And I think we, we confuse
content with complacent.
I think there's, I think there
is a situation where we can
absolutely be satisfied with
progress and be content with
progress and not be complacent,
which to me, like it's always,
I've always put with like
being asleep at the wheel.
Right.
It just means you're, you're
no longer reacting anything.
You're no longer
thinking about it.
You're just saying
like, it is what it is.
And we'll just, we'll
just see what happens.
Right.
We know what happens.
Right.
Um, we do get eaten
by somebody else.
And I picture this over and
over and over, I picture
all the big, fat, dumb, and
happy businesses out there
Yep.
That are about to
get eaten next.
Yeah.
Yeah.
Like one for, for some
reason it just sticks
in my mind is TurboTax.
Here is a piece of
software that's still
sold as box software.
Yeah.
You can
still it buy it 90 on it
on a physical disc.
Yeah.
Right.
It's unbelievable
that, that that product
has made it this far.
Mm-hmm.
Now, in an era of ai, that
product makes no sense,
no sense whatsoever.
It couldn't be less intuitive.
Yeah.
Ironically, coming from
Intuit, it could not be less
like a dynamic or updated.
Yeah.
It is slow as shit.
I use it every year, by the way.
Yeah.
And it's, it's
still it every, every year,
right?
I am like, how is this
product still in market?
And I've gotta imagine within
the next 18 months somebody
comes up with something that
just sucks in all your stuff,
figures it all out for you, and
puts in the, the perfect doc.
I don't know how you couldn't.
And I think about that
and I think there's
someone add into it.
That's the, the, you
know, EVP of that product
division, et cetera, that
has gotten paid so much
Yes.
For so long.
Right.
And you know, big,
fat, dumb, and happy.
Right.
And all of a sudden, all of
a sudden everything changes.
Now on the one hand, kudos
to that guy for enjoying
the hell out of his career.
Really long of time.
He's probably
lived a great life.
Yeah.
But for the rest of us,
like I am constantly worried
that tomorrow the other shoe
drops and I lose everything.
Like I don't have that,
that moment of arrival.
Yeah.
Well, and I think it's
interesting, like even kind
of regardless of where you
are, even if you are like.
Winning, let's say.
Yeah,
right.
In a Darwinian game, even
success can feel a bit like
a countdown time, right?
Like I, I remember there's
times where like, oh, we're
doing well enough now that we
start to gain some notoriety.
Like, sometimes that just
feels like painting a
target on your back, right?
Right.
Now people are gonna come
out, they're gonna try to
copy, they're gonna try to
jump into the market, right?
We saw this with crowdfunding.
Uh, we saw this with
advice networks.
We've seen this happen over
time with some of the businesses
that we've built, and, you
know, it never feels good.
Right.
It never feels good to know
that there, there's somebody
even just know there's somebody
trying to eat your lunch.
Yeah.
Right.
Whether they succeed or
not, it just, there's always
that little bit of fear.
At the back of
your mind that it's
Yeah.
Drives other anxiety, right?
We're we're reaching for,
for dopamine with one hand
and trying to shove back
cortisol with the other.
It's a great recipe for
a long-term healthy life,
and it's interesting because
depending on how you look
at the spectrum of types of
companies that get started
in our world, okay, yeah.
And the one hand
you've got the most.
Innovative companies, and
when I say innovative, I
mean by like high turnover.
The latest and greatest
is changing all the time.
Sure.
Right?
Yep.
Exactly.
Where like the, the top three
AI companies are right now.
Yep.
We're just like, every
day there's a chance that
something comes out Yes.
That eliminates your market.
Yep.
On the other end of the
spectrum is a restaurant.
Yes.
Right.
Other than serving shitty pizza.
Yeah.
There's nothing that
is going to be made
obsolete in your business.
Right.
Anytime soon.
So long as you show up in a good
product, give cus good customer
service, you'll be okay.
Right.
Now.
So those folks, I'd like to
believe, other than, you know,
the perils of making payroll,
just the nature of running a
business, maybe sleep better.
But most of the folks that
show up in our world Yeah.
Are more toward the other
end of the spectrum.
Oh, a
hundred percent.
Where their actual entire
business can go away.
Yeah.
Like fairly quickly.
Fairly quickly.
Within a couple
years, sometimes less.
And that becomes a very
hard place to be complace.
Yeah,
for sure.
How much do you think that the,
the fact that we are sort of.
Brutalized into chasing metrics.
Does, does, yeah.
Does that, how much does
that feed into this?
Because I feel like part of
the startup culture idolizes
grind simply because it's
really easy to measure, right?
Yeah.
It's, it's hard to put
peace on a dashboard,
right?
Yeah.
Well, yeah.
What is our inner peace
quotient this month?
Right?
Nobody knows.
I gotta tell you, man.
You and I are, you know, pretty
introspective pers people.
And, and I think over the years
we've tried to do a better and
better job of saying like, you
know, where's my happiness?
Where's, where's
my contentedness?
And I think for myself,
I've found that my
contentedness has never, ever.
Ever come from my jobing.
Now a sense of validation,
you know, I do something
big or something like that.
Yes.
You know, a, a win, you
and I have been celebrating
all kinds of wins later.
Yeah.
Fucking feels great.
Right?
But I've never been Content.
Content, yeah, yeah, yeah.
Content like content is
how I feel about my wife.
Right.
Yeah.
Like I don't want anything
different from her.
Mm-hmm.
Like I am very content with like
where things are in our life and
I don't want things to change.
Like I don't want
anything to change.
Right.
Content is where I
feel with my kids.
I want them to do better
things, but I like
they're incredible kids.
Yeah.
Like that level of contentment.
Just does not
exist in my career.
What is it like for you?
Like how do you see it?
I hadn't thought about it
in that regard, but I think
you're, you're spot on.
Right?
There are things
that make me happy.
There are things that we
celebrate, but in terms of
contentment, again, I think
to some degree it's just
like it's beaten out of you.
We think of slowing down
is equal to death, right?
And so.
It's now making me wonder
how many things I've sought
out outside of, outside of
work that do have like a, a
sense of completion so that I
can achieve some contentment
in life that doesn't come
from this thing that we
spend most of our day doing.
That's interesting.
But now I think I'm probably.
Pretty much same page, which
is that, yeah, I'm not content.
There's always some other thing.
There's some other way.
There's always more or better
or faster or cheaper, or there's
some, there's always one more
dial you can adjust, right?
There is this, it's a
dashboard with an endless
number of buttons that can
be pushed and optimized.
You know, something
that's really.
Funny about everything
we talk about here is
that none of it is new.
Everything you're dealing
with right now has been done a
thousand times before you, which
means the answer already exists.
You may just not know
it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems all
dayLong@groups.startups.com.
So if any of this sounds
familiar, stop guessing
about what to do.
Let us just give you the answers
to the test and be done with it.
I've always traded.
Need to get it with,
don't wanna lose it.
Yeah.
So like for me, like I remember
specifically, I've told you this
story before, but like when I
was, my dates are all getting
messed up, let's say 25, right?
Sure.
And I go to the, the car
dealership and I bought
a red Lamborghini, right?
And I remember, I, I go to
the finance manager in the
back room and he slides me
the, the payment and it's
like $6,000 a month Uhhuh.
Okay?
My mortgage was $1,500
a month at the time.
Right?
So to give you an idea
adds
up of this, of
this delta, right?
That checks out in, in
retrospect, what's that?
That checks out.
I, it totally
makes sense.
Yeah.
Right.
In retrospect, I think maybe
$2,000 of that was principled.
The other $4,000
was finance fee.
Yeah.
Because they were like, dude,
if this idiot pays this,
yes.
Even if we get paid for two
months, we're gonna make money.
Huh.
Anyway, while I was doing the
paperwork, the only thing I was
thinking was this will last for.
A month, two months
before someone comes and
repossess this vehicle.
Yeah.
And it gets taken away from me.
Like, there's just no way a guy
like me, like will get, and, and
that was a very serious thought.
That wasn't like, like
a flippant ha ha, but
I don't really mean it.
Uh, I absolutely meant it.
It's like, yeah, there's no
way there's staying around.
And like every time in my
life when something went
well, my first thought
is I'm gonna lose it.
Uhhuh.
Right?
Like the, when I look
back, I never have.
That's weird.
I never really
thought about that.
Yeah, like I never actually
did lose something.
Maybe because I was so paranoid.
Maybe.
Or maybe that's just
not how it works.
But how about this?
How about spend the next
couple of months, try not
to be paranoid and see if
everything gets taken away.
And then if it does,
then you'll, then
you'll know for sure.
I am so hard coded
on this one, man.
I like, so, you know, a lot
of times we give people like
life advice or you know,
startup advice, et cetera.
Yeah.
But.
I dunno about you, but I
often tell people, here's my
experience, here's my bias.
And guess what?
What worked for me or
didn't work for me?
Has nothing to do with you.
Just you.
Yeah,
exactly.
Take with us what you will.
Don't use it verbatim.
Yeah.
And I always tell people, I'm
like, A lot of what made things
work for me are behaviors I'd
highly recommend not pursuing.
Yeah.
That's the thing.
That's a thing.
Yeah.
When I look back at the
trajectory, they're like, so
what was your path to this
like, and I'm like, let me
not tell you 'cause I don't
want you to try to repeat it.
There are easier.
Easier please ways.
Getting and doing the thing
that you wanna do than, than
what I did before we move on.
How do we stay hungry without
making our team live with
like perpetual scarcity brain?
Let's just pretend for a minute.
We can't avoid it as founders.
Like it is just, we're,
we're stuck with it.
How do we keep that from
becoming pervasive in
the, in the organization?
You know, it's interesting, man.
I don't know if everyone
else feels the same way.
I don't, I, I, like,
I haven't seen it.
At like a persistent
level over 30 years.
Right.
And I think it's because
for a lot of other
people it's just a job.
Yeah.
Right.
It's kinda what we said before,
like, Hey, if this doesn't
work out, it would suck that
I have to get another job,
but I can get another job.
So like everyone's worried
about losing their job, but
at the same time, we've talked
about this before, they don't
have the liability of losing
everyone else's job too.
Like you and I talk about
this all the time, like
even in our own company,
like if we make mistakes,
it costs everyone their job.
Right, not just us.
That's a way different
like level of anxiety to
live with than just having
to deal with yourself.
Also, like if you're on
payroll, let's say right at
whatever company and you did
what you're supposed to do,
you get high fived and you
go home, you can reasonably
expect to get paid next week.
Yeah.
Right?
Like again, unless you've
done, you're a salesperson.
If you're a salesperson,
you're hitting your quota.
You can reasonably expect,
I mean, yeah, and I say
that because it's numeric.
You can look at it and
say, Hey, you know, I did
exactly what you said and
I'm gonna get paid, whatever.
But founders don't really
get that, that luxury.
We could do everything
right and still get the, the
rug pulled out from under.
It happens like every
frigging day, right?
Like, like people think,
oh, you're your own boss.
They're like, no, I just get
fired for different reasons.
Yeah, right.
It's not that easy.
Yeah.
And we gonna have
to fire myself.
Right?
Even worse.
So what do we do
about all this, man?
How do we feel better
about all this?
What we offer a little ray
of sunshine for founders.
Okay.
So.
The first time it happened for
me, the first time that, that
I felt a sense of completion.
Mm,
had nothing to do
with work whatsoever.
So when I was traveling
back and forth between
Columbus and uh, la.
I was, uh, back at
the house in Columbus.
We had, and you already know
the story, so I'm telling
the audience, we had this,
uh, three car garage at our
house that was totally empty.
Like it was, it was nothing
but, uh, studs in plywood.
And I went in there and I, I,
one weekend, for some reason,
I had it in me that I wanted to
build a, a workbench in there.
I remember, I don't know
why I did this first, but
it was genius in retrospect.
I put like an old
flat screen tv.
It's funny, I'm calling
it flat screen tv.
What was it gonna put
a tube TV up there?
Was it plasma?
Anyway, so anyway, so I, I put
it up there and I hooked it
up to the internet so I could
have YouTube and I was watching
a YouTube guy show like how
to build a certain kind of
workbench uhhuh, and I was
just following along, right?
Yep.
Again, I, I was handy,
but I wasn't a carpenter.
And so after I built
the bench and I'd spent
like four days doing it.
I was like, huh, it's done.
Yep.
Like I worked really hard
on something that I cared
about, but it's actually done.
Yes.
And it was this weird feeling
that I had never had before,
which was called completion.
Yeah.
And I say like a lot of
times I'll talk to founders
and they'll say, yeah, this
weekend I just like cleaned
up my yard or cleaned
up my house or whatever.
And they're like, I
just needed to do it.
And I was like, there's
a reason for that.
Yes.
Your mind needed to
complete something.
You needed to, to to
take order to chaos.
And I think that action,
cleaning your living room or
gardening or whatever Yeah.
Was something you
could actually finish.
Yes.
And it brings a
sense of completion.
And dude, as you know.
Once I started, the
irony is that I never,
it never ended, right?
Like after that I just like
never stopped doing carpentry.
Yeah.
You turned that completion into
a never ending train of other
completions, but there's a
bunch of completions in there.
At least
when you and I were working
together, it'd be like a
year or two ago, and we
were like building drawers,
I think for For the house.
Yeah.
It was cool.
Right.
At the end of the day,
we had a whole stack
of drawers everywhere.
We had 64 drawers.
Yeah.
I was like, we made
some drawers today.
And it's like in, in
the drawers, there's
a freaking drawer.
But the point is like it
felt so they're done unusual.
They're
right.
You don't ever have to build
those 64 drawers again.
Well,
and it was tactile, right?
Yeah.
I remember Jamie Simoff, you,
the, the, the founder of Ring
told me, he's like, I've never
built something that prior
to this kid in six companies.
He's like, I've never built
something prior to that.
It was ever in a landfill.
Right.
Which I always thought was
an interesting like way
to describe his product.
That is interesting.
But he is like, I never
had something physical
that could be thrown away.
Yeah.
There's something to that.
But I think there's, yeah, from
a, from a business perspective,
I think that's absolutely true.
And, you know, completion
is such a, it's a
psychological nutrient, right?
Yeah.
Without it, I get
twitchy, irritable, right?
Compulsive I, I'll go
looking for something to
go just to complete, right?
I think that's what it is.
Like, I'm gonna
go clean the room.
I'm go do this.
One of the things I realized
that I started to do was not
only did I want things that,
that had completion to them,
but that were sort of like.
Monuments or some in some way
memorialized things, right?
Mm-hmm.
So like the, you know,
building the playhouse
for the kids, right?
Has a completion and
it's, then it's there.
I see the damn thing, right?
I watch them play in it.
They enjoy it.
The, the chicken coops,
guests physical, I can see it.
There's a whole, there's
an ecosystem that
gets built around it.
The pond, right?
I walk and I can sit by it.
So it wasn't just that I
needed completion, I actually
really enjoyed when I had
something I completed.
That.
Then I could also like go and
just be near like, so there's
a constant reminder essentially
of the completion, right?
It's like I needed it to be just
pasted there in front of me.
It was like, yeah, you did that.
It's done.
Now you're okay.
Well, I tell you what though,
what it unlocked for me was
realizing that the lack of
completion was an issue.
Again, up until that point,
I'm like, by the time I
start doing this, I'm like
20 years into my career.
Yeah,
and I remember like a
little bit prior to that,
we had launched fundable.
So just you, you kind of
timestamped that for you.
I remember the day we
launched fundable, it
was May 22nd, uh, 2012.
Yep.
And it was such a run to
get to that milestone.
Right.
And, you know, we just
went through, uh, endless
hell to get there.
But I remember the day
we launched it, it was
like this, this muffled.
Scream, Uhhuh, and
then that was it.
And then like, it
was so uneventful.
Yeah.
It was so incredibly uneventful.
And now nothing happened.
Nothing wrong.
Right.
And like a lot of what we
do is particularly, you
know, in startups and web
startups and stuff like that,
has so little like, like
visceral completion to it.
Yep.
And even the wins just
don't feel like anything.
I remember years ago hearing
Mark Cuban talk about when he
sold broadcast.com and he got
a a billion dollars wired into
his bank account, so to speak.
Yeah.
And he said it was the
most unfulfilling thing
you could imagine.
He's like, I just sat there
hitting the refresh button
over and over and over on
my browser until it hit.
And when it did, I was like.
Huh.
Now what do I do?
And, and that's a
billion dollars, dude.
Right?
Like, I mean, it doesn't
get bigger than that.
And I hear this all the time.
Yeah.
It's very possible to work on
something that just doesn't
give completion or fulfillment
the way we expect it to.
Yeah.
And dude, we spend an awful
lot of hours working on
something that, that doesn't
give us that, you know?
Yeah, it's tough.
And I mean, startups really
just don't give closure.
It's not part of what Right.
They, what they're
able to provide.
They provide a lot of other
things, but you need it, I
guess we have to figure out.
Right.
So to me, the startups
are the engine.
Right.
They're the things
that constantly moving.
Our life has to be those,
those kind of stop points and
provide that for us because
if nothing ever ends, like
we never get to exhale.
Right?
Right.
Our poor brains,
our body's just.
All of it.
Right.
And to me, like completion isn't
luxury, it's it's maintenance.
We do need it.
Yep.
To your point, like you didn't
know that you needed it and then
you, then you felt it and you're
like, oh yeah, that was good.
Right.
And so,
right.
I can come in and come in
all kinds of forms, right?
Like for me, cooking a
meal, I love the process.
I love the creation of it.
I love every bit of it.
But it also has an end.
Right?
Right.
There's also, you know,
sometimes there's a day or
two of it left over in the
fridge, but, um, there's,
there's an end to it.
Finishing a workout.
Awesome.
Right.
Going on a hike, writing
something we can publish and
walk away from cool woodworking.
Right.
And so, yeah.
To me the magic isn't the
hobby itself, it's the
definitive finish line.
Right.
The fact that there is a,
like, there it was, we did it.
I think it's two stages.
One stage is recognizing
that our work doesn't have
that fulfillment moment.
Yeah.
Right.
That completion, it's done,
it's eternal kind of moment.
It's not that like, you know,
people like, go, well you,
you built and sold a company,
or something like that.
I'm gonna tell you that way less
rewarding than you think it is.
And, and I, and I hate when
people say stuff about like,
like Mark Cuban, you know,
getting a billion dollars and
saying it was unfulfilling.
It's like, fuck you, mark Cuban.
Right?
Yeah.
But he's not wrong.
He's not wrong.
Right.
I don't feel bad for the guy.
Yeah.
And he's not saying
feel bad for me.
He's, his point is,
his point is,
dude
didn't do what I
thought it would do.
Yeah.
Like, how is that possible?
Like, he's like, I, I see
it the same way you do, and
I still can't believe it.
Yep.
So I look at it and I say,
man, the first step, I wish I
had known this 30 years ago.
The first step is recognizing
that we're in a business.
That doesn't have completion.
Milestones.
Yes.
It doesn't have full
like finalized, right?
It's done.
It's done.
We don't have to
do that ever again.
You raise round of capital
the moment you're done,
you gotta be back out
raising more capital, right?
You hire another employee.
The moment you do that, you now
have another liability that you
have to go service with more
revenue, like it never ends.
Now, if that's the case and your
work doesn't have, you know,
that kind of final completion,
relax, you still need that.
Yeah,
for sure.
You're just not gonna
get it from work.
And that's what never
occurred to me, Ryan.
It never occurred to
me that like, I need
that That was one Yeah.
In second.
And it wouldn't come from work.
Right.
Once I put those two together,
I mean, my paranoia isn't
gone, but like, yeah.
But, but man, when I'm doing,
but, but it gets at least a
little bit of a rest period
when I'm doing fulfillment
work, and that is straight
up hardcore labor, right?
Yeah, that's, that's me
building stuff, you know?
Yeah.
Just being an insane carpenter.
I do it more so than anything
because I love being done.
This past weekend I was building
a catwalk of all weird things.
Right.
You know, like the
catwalk is my living room.
Yes.
And I was doing like
all the trim pieces.
It sucked.
I actually don't, don't
enjoy doing that whatsoever.
Yeah.
But when it was done,
it looked badass.
Yeah.
It looked awesome.
Right.
And, and it's
complete.
Yeah.
Man, I Right.
I was like, it felt so complete.
Also, particularly in this case,
when I'm building something that
I know could be there forever.
That has like an
incredible field.
Yes.
That's that, that's what I
was getting at before, right?
It's memorialized, right?
Yeah.
Like I did this thing and
I'll be able to look at this.
I'll be able to run my hand
along that trim work forever.
Exactly.
And, and to that end, like, you
know, these are, these are all
little things and I think one
of the challenges that I had
early on when I was trying to
figure all this out was that.
I kept looking for things that
would have a completion that
was equal to the whole, that
was left by sort of the, the
lack of it in the startup.
Oh,
yeah.
Right.
In like a single event.
Love that, right?
Yeah, yeah,
yeah.
Like, okay, what can I do that
will then be that thing, right?
Is it start the family?
Is it build the house?
Is it whatever?
Right.
And instead, what I
realized over time was.
Just plenty of little
completions is fine.
Right.
Because
Right.
That relief compounds
just like stress does.
Right.
So for me, small finishes were
more than enough to refill the
tank and I think that's what
I've started to, to focus on.
It's not what you finish,
it's that you finish.
That's exactly
it.
Is that you finish it all in.
Yep.
If I stop, say doing
carpentry, as you know,
my hobby and my completion
mechanic, I don't actually
have other things that I do.
Give me that sense of, of
completion and fulfillment,
even though I literally
build things for a living.
Yeah.
Like, and what's nice about,
you know, doing anything
like that, or even like you
were talking about making a
meal, getting a good workout
in, playing a sport, you
know, whatever your thing is.
What I'm saying is don't
look at that as trite
compared to your startup.
Correct.
Because the dopamine
hit that you get out of
that is meaningful, the
sense of completion.
It resets.
Yeah.
Right.
Like it puts stuff
like back in the tank.
Yep.
And I think for so long,
for so many years, like
decades, I kept taking it
out and I could never figure
out how to put any back in.
I hear a lot of people talk
about this with, uh, with wealth
where they say, you know, I
made some money and I bought a
thing, you know, like to car,
you know, house or whatever.
And then the novelty wore off.
That's nature of it.
Novelty wore off.
And so I tried to buy another
thing to replace that feeling
of accomplishment, whatever.
And then that novelty.
Novelty wore off.
Yeah.
And then what happened is
every single time I tried
to spend more go outdo it.
Yep.
To get that feeling back of
finality and it just got worse.
And it's actually like a
legit problem for people.
Yep.
It's like we all know
an adrenaline junkie.
Right.
And like, it's like whatever
it took to, to shake them
and, and to satisfy that
need, it just becomes more
and more and more each time.
Well, right.
Where that becomes an issue is
we're trying to solve a problem.
Yeah.
With a mechanism that
doesn't solve that problem.
Correct.
We're, we're trying to
buy more stuff and then,
then we'll be happy.
Well, it turns out buying stuff
doesn't sustain happiness.
Yeah.
It gives you a short
bit of happiness.
Short terms.
There's something really
cool about rolling off the
lot in a new car, right?
Yeah.
But within three weeks,
you just can't sustain like
that level of happiness,
maintenance bill.
Exactly.
And then you're, you're, you're
trying to, to buy the feeling
of rolling off the, the, the
lot in the new car again.
Yeah.
And it just kind of
doesn't work that way.
Doesn't come with the car.
Um, I always thought, okay, so
this was me like again, early
in my career, in my life, I
thought that once you could
get like a few of the staples
of life, car, house furniture,
so to speak, that you're done.
Yeah.
I remember there's this
quote by, uh, Edward
Norton and Fight Club.
Remember when he was going
through the IKEA catalog?
Oh, yes.
And he says something to the
effect of, he is like, I just
assumed, you know, I, I had the
couch, I had, you know, this.
He's like, so that
problem was taken care of.
I'd never have to deal
with that problem again.
Right.
And I was like, that's
exactly how I was, was
thinking at the time.
Uhhuh like, you know, once I got
the IKEA couch, I, I'm the nan.
I would be fine.
Right.
But it turns out that burns off.
And you need the next
thing and the next thing
and the next thing.
Whenever we're trying to
fulfill ourselves with these
bottomless pits, it ends poorly.
So again, I wish somebody
told me, dude, find something
else to fulfill yourself.
'cause this ain't it.
Yeah.
And it's true.
You know, I think it's a
piece of advice I started
giving myself was stop
obsessing about the next
thing you're gonna start.
Start obsessing about the next
thing you're gonna finish.
And that helped me a lot,
I guess, like, look, as
founders as creative people,
as, as people who like to
build and, and are, are
capable of doing it, it's
really hard to avoid that,
that trigger and that urge.
But I think that as I've, as
I've gotten a little older, a
little slower, a little more
mature, I've figured out it's
like, look, just there's,
it goes back, like there's
that sense of completion.
Like, let's finish this
off before we, before
we start playing around
with what's, what's next.
My ratio of earning things
to, uh, appreciating
them is one to 99.
I I will spend 99% of
my time earning things.
Yeah.
And at best, yeah.
1% of my time appreciating them.
Yeah.
Now, when I say earning
things, I mean, it could
be literally anything.
It could be a sport that
I played, it could be, you
know, something that I built.
A
skill that you've learned.
Yeah.
Yeah.
I will work so hard to win
at a hockey game, but when
I win, I won't give a shit.
Like it has no, like the,
the effort pays me nothing.
Right?
Like I just, oh yeah, okay.
We won.
Whatever.
I would love to have this like
inner compass that said, I will
only work on things if I spend
an equal amount of time getting
them as I do appreciating them.
Ooh, ooh.
Which means I work on nothing.
There's a complicated calculus.
Yeah.
I can't do it.
But that seems like
a really cool goal.
It does.
I will say this, the only
thing in in my life that I
would say I've spent more
time appreciating than
working for, and this is gonna
sound wrong, is my family.
Yeah.
No.
I mean,
yes, not because I don't work
for it because I spend so
much time appreciating, yeah.
Being appreciated
for, for my family.
Yep.
Same.
And they don't require
like some like life
sucking effort out of me.
No.
I mean, just have great family.
So do you, Jason k said
this once, he said kids are
the only thing that that
isn't under underrated.
Yeah,
because it's the one thing
that can give you back
that's depending your kids.
That's
so true.
Uh, it's the one thing
that can give you back
more than you give to them.
Yeah.
Not that that needs to
be the ratio, but it's,
it's pretty incredible.
I haven't been able to find
that many kind of sources
of completion, of certainty,
of like being able to
appreciate that are like so
polar opposite, you know,
from what we do in startups.
Yeah.
I guess what we're saying is
that startups are marathons
with zero finish tape.
Right?
So.
Expect them to deliver.
A permanent sense of rival
is a rigged game, right?
Like we can't have
that expectation.
So if you, it's a Rigg
game, do want fulfillment,
you have to manufacture
some kind of completion
outside the company, right?
For will, it's building things
for me, it's playing sports,
sometimes building things, uh,
but they have to exist for us.
So don't worry about
the next thing.
You're gonna start, worry
more about the next thing
you're gonna finish, and
if it feels ridiculously
good, and it will also make
you better at the marathon.
Overthinking your startup
because you're going it alone.
You don't have to, and
honestly, you shouldn't
because instead, you can learn
directly from peers who've been
in your shoes.
Connect with bootstrap
founders and the advisors
helping them win in the
startups.com community.
Check out the startups.com
community@www.startups.com
to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.