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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 another episode
of the Startup Therapy podcast.
This is Ryan Rutan, joined
as always by my friend,
the founder and CEO of
Startups.com, Will Schroeder.
Will, as founders, we
don't really leave work.
We just change rooms
while the startup keeps
shouting in our minds.
Mm-hmm.
Uh, the real question isn't,
like, how do we stop thinking
about the company, it's
how do we turn that 3:00 AM
panic into something useful
before it eats us alive?
When did you realize that
your startup brain wasn't
solving problems anymore,
it was just burning fuel?
It took me a while, but,
like, I remember... So
this started in '94.
Like, I started my
first startup in '94.
Yeah.
And I would argue that's the
year the problem started.
That much I know for
sure, but it never ended.
And, like- Uh-huh ... I thought
in the early years that worrying
had a lot to do with ... Because
I didn't know a lot, right?
You know, I was learning
everything for the first time.
Yeah, yeah.
Sure.
So this, this worrying was
a facet of I'm gonna go in a
room tomorrow, and I'm gonna
present to clients, or I'm
going to talk to, you know,
my coworkers, et cetera.
Right.
I don't know what I'm doing,
so I'm very worried about that.
That's legit worry- Sure.
Yeah ... topic, right?
And so I built a habit of just
worrying all the time, right?
And I think part of
it is an OCD thing.
Part of it is literally the
job of being a founder, right?
Yeah.
Like, our job is to be
worried about all the
things that other people
aren't worried about because
that's how we notice things.
Uh, just f- funny quick aside,
years and years ago when I
was running a company called
swaplease.com, Swaplease was,
was, was originally founded
not by me, but by the Joseph
Auto Group, which is this large
automotive dealership- Oh, yeah,
yeah ... out of Cincinnati.
And, um, I remember talking
to one of the Josephs.
He's a fourth
generation car guy.
Their great-grandfather had a
statue of him at the Chiquita
Center in downtown Cincinnati.
Like, that's how, like,
ingrained in the city they were.
Yeah.
Anyway, I thought
it was fascinating.
And so one day he's telling
me about, uh, how he manages
across all the dealerships.
And I was like,
"Well, what do you do?
Just like go in and walk
around?" He's like, "Yeah,
this is exactly how our
family does it." Yeah.
He's like, "And here's
what happens." I thought
this was fascinating.
He said, "We walk out on
the lot, and we look around.
Are the cars dirty?
You know, I run my
finger across the cars.
Is there any dirt on it?
I look at the salespeople.
Where are they
standing right now?
Are they standing all in the
back doing a smoke break?"
Right? "I look at, uh, how many
people are here as customers
and how many are being attended
to right this second." Yeah.
And I was like, "That's it?
You, you don't have, like,
metrics or performance?"
He's like, "Nope. Everything
you need to know, you can just,
uh, walk on the lot and start
worrying- Just see ... and
it'll surface itself." What a
luxury.
Yeah.
What a luxury.
My God.
It's like, "Oh, that's
interesting." But the
mental model it gave me was
there's a job of worrying.
There's a job that just involves
walking onto a lot, so to speak,
you know, your startup- Yeah
and seeing like, "Oh, why isn't
that working? Hey, that does,
that shouldn't be where it's
at." Like, and just basically
worrying about all the details.
Well, I think as founders,
like, that is our job to walk
on the lot and run your finger
across a random car and see,
like, how much dust is on it.
Like, to look at all
the details- Yeah
that most people
aren't looking at.
But in order to have that frame
of mind, you've gotta constantly
be worrying, I thought.
Mm-hmm.
Like, and at some point, to
answer your question, I realized
to myself, like, I wonder if
I could get great at this.
I wonder if I could- Right
... get great at worrying, right?
And I know it sounds
contradictory, but I feel
like I've kinda done a good
job with it, which means I've
also had to stop worrying.
Yeah.
Yeah, no, I think it is.
I mean, if you go back to
the, the metaphor, right?
So, like, if you have to
walk the lot, you might as
well be really good at it.
You might as well
figure out, like, how
do I take these inputs?
I'm gonna be doing this anyways.
I, I might as well do it.
Because otherwise, it just
ends up being like fear dressed
up as responsibility, right?
And we tell ourselves
to be vigilant.
Awesome.
Say that again.
What's that?
It's fear dressed up
as responsibility.
I've never heard that framing.
That's brilliant.
I like that a lot.
Yeah, so I... That's what
it feels like, man, right?
Like, uh, because we, we tell
ourselves that we're, we're
trying to be vigilant, right?
Yeah.
But a lot of times we're
just trying to feel in
control of something that is
inherently uncontrollable.
It's a startup, right?
Yeah.
Most of it is absolutely
out of control, but our poor
founder brains just feel
like rest is negligence.
Yeah.
And so then we start
to conflate constant
attention with protection.
My fear was always that not just
that the company's gonna break-
But that if it breaks while I'm
not thinking about it, we'll
blame ourselves forever, right?
It was, it was almost like
for me- Right, right ... it
was like, as long as I'm
actually worried about this,
even if it goes sideways,
I can say, "Man, I was all
over that and I just didn't
figure it out," as opposed to,
"I got blindsided by that."
Well, it, it occurred to
me as I was say- talking
through this, there, there
was such an analog to, like,
having newborns where, like,
you're laying there in bed-
Yep ... and you're like, "Is
the baby breathing? The baby's
probably not breathing." Yep.
"The baby might not be
breathing. I'm gonna go check
the baby." But the baby was
always breathing, right?
Yeah.
Like, thank God.
Thankfully,
yeah.
Um, but like that was that
feeling, and it was like,
if I don't get up and go
check, like of course the
baby's probably breathing,
but if I don't go check,
I'll never forgive myself.
That was what it felt like.
There's a healthy
amount of that, right?
But I think for what
we do, there is a very
unhealthy level of that.
Oh, for sure.
A couple years into my, uh,
career, th- this is '96,
I'm walking through Barnes
& Noble back when bookstores
still existed, and I look
at, like, the number one
selling business book at the
time, and I was all about
business books at the time.
I remember it was Andy
Grove, you know, one of
the co-founders of Intel.
Oh, yeah.
And I'll never forget
the title said, "Only the
Paranoid Survive." Oh my God.
And for some reason-
Thanks for that, Andy
...
thanks, Andy, right?
Like, for some reason that got
burned into my brain, right?
Oh, yeah.
And maybe it was already
there, like maybe it was just
like reinforcing my, like,
psychotic personality trait.
But I remember thinking, well,
if Andy Grove feels that way at
the height of Intel- Yeah, yeah
... right, and that was the title
of his book, like what's the-
Right ... fuck up by the way?
A guy writes one book
and that's the title.
I was like, maybe there's
something to that.
And so over the years and
decades that would ensue,
as I spent countless
hours at 3:00 a.m.
staring at the ceiling,
including yesterday at 3:00
a.m. staring at the ceiling,
I thought to myself, I was
like Why can't I stop, right?
Yeah.
Like, like why is it everyone
else seems to be just fine
going to work, leaving work,
going home and dealing with
whatever life problems, but like
basically not worrying, right?
Yeah.
About the stuff that I worry
about, which is everything.
I think part of it is I still
believe, this is, you know,
personally, I still believe that
I'm waiting for it all to end.
Like in my life, you know,
you and I have talked about
this before, I'm still waiting
for the other shoe to drop.
Yeah, yeah.
Like my entire life has
been me going, "Well, I'm
glad things went well, but
this'll end soon." Right?
Right.
And I'm just like, like,
you know, one step away
from all of it ending.
And I look back and like I
somehow made it 32 years without
it ending yet, knock on wood.
But I've never lost that feeling
that this is the last dance.
It's almost like a weird
founder superstition, right?
Yeah.
Like if I stop worrying,
I'm inviting disaster.
I'm, I'm gonna let it
cross the threshold.
Like my anxiety is
somehow what's keeping
the servers online-
Yeah ... what's keeping Stripe
transactions happening, right?
Trying to, yeah.
Uh-huh, uh-huh.
I always have this little
thing, this conversation
that I have with myself at
3:00 in the morning where
I'm like, "Dude, not again."
I'm like, like we know
how this story ends.
And, and, and here's
what I thought was
fascinating about it.
I'm laying in bed and, you
know, all of a sudden I
wake up and I'm like, "Oh,
fuck. Here we go," right?
And I'm like, I already
know what's gonna happen.
I'm gonna take inventory
of everything that I should
w- worried about right now.
Yep.
I'm gonna pretend that I
can solve every one of those
problems while lying- Oh,
yeah ... in bed at 3:00
in the morning, right?
And the entire time I'm
just like, "Brain, shut
the fuck up," right?
Yeah.
Just, just stop.
Like you're not being
helpful right now.
Right.
Like none of this is useful.
And I know where it comes from.
I don't really wanna
solve a problem.
I'm manifesting fear, right?
Like I'm manifesting just
a lifetime worth of fears-
On whatever problems
happen to exist today.
Yes.
And the reality is, the
problems changed year to
year to year, but how I dealt
with them did not at all.
Man, I've even seen it when
there are no problems, like
fear will still manifest, right?
'Cause then, then you have
to ask yourself, right, am I
afraid to stop thinking about
my business because the company
needs me to do that, or am I
afraid that it doesn't, right?
Right.
We never let it rest, man.
Like, how many founders, how
many times have you taken a
vacation, Will, and, or you like
spent the entire time mentally
doing disaster simulations
from your beach chair, right?
'Cause I know you're not just
sitting there reading a book.
That's exactly what I
was just thinking as,
as you were talking.
I was like- Yeah ... have I
ever taken a vacation that
actually felt like a vacation?
'Cause I can't think of one.
Nope.
And then I was thinking,
have I ever taken a vacation
where things have gone wrong?
And the answer is
yes, like a lot.
Yeah.
Almost like comically.
Like years ago, you'll
remember this, I was on a,
a vacation and I was taking
my daughter Summer to, to
Comic-Con, right, in San Diego.
Oh, yeah, yeah, yeah.
Yeah.
'
Cause I know where
this is going.
This, I remember this.
Yeah, I've been wanting to
go to Comic-Con fucking ever.
Like I'm a huge Marvel nerd.
Yep.
So like, you know, I, like
I couldn't wait to go.
And the fact that my daughter
was old enough to make it
look like I was taking her
for her benefit and not mine-
Yeah,
yeah ... um, was just perfect.
Um, at some point I'll go
with, with my son Will,
and I can't imagine.
I'll be there for a month.
Anyway, point is, as we're
driving down, I get a call from
our CTO, and he's like, "Hey,
our system's been hacked."
And I'm like, "Okay," right?
And this is, this is
my thought process.
My first thought process,
I need to turn around right
now, go back, as I live
in LA, like go back to
LA and go deal with this.
But then I'm like, my daughter's
sitting in the car with me,
like we're literally driving
to Comic-Con as I say- And
I'm dressed as Batman.
Yeah, exactly right.
I was Fat Deadpool, but yeah.
And so we get there.
While it's happening,
Comic-Con's overwhelming, right?
It's just massive,
like show floor.
Yeah.
And mainly all my daughter
cared about w- was the,
the vendor convention
where you could buy shit.
Yeah, and s- so anyway,
we're walking the, the, the
convention floor, and all I
can think about, not Comic-Con,
not this awesome opportunity
with my daughter, how like
over the moon she is- Yeah
or how many other Fat
Deadpools there are, right?
It's, "Holy shit, we got
hacked. I need to get out of
here as fast as possible and
do something about it." Right.
Now full stop.
There is nothing I can
do about it, right?
Like- Right ... I'm
not the anti-hacker.
There's nothing like
I can do, right?
Yes.
And yet I'm like, "Here's
what's gonna happen.
I'm gonna erase everything
happening that isn't this
problem and focus on that."
It's so brutal.
W- with the, and then like
you just described something
that I've, I've caught myself
doing so many times, which is
like this difference between
thinking and, and just looping.
Right.
Where like thinking, in my
opinion, like it produces
options of some sort.
There's something I can
do as a result of it.
Yeah.
Looping, on the other hand,
produces cortisol, which
also then produces belly fat.
Um, I can tell you that
is working just fine.
And I think that, you know,
once the, the mental activity
stops creating decisions,
it's no longer work, right?
It's, it's just suffering
with our startup logo
stamped right in the middle
of it, and it's like it's
not helping at all, right?
If you can't take action
on it, stop, and yet
damn is that hard to do.
This just brings us
back to 3:00 AM, right?
3:00 AM- Yeah ... like tonight
at 3:00 AM, I'm gonna wake up.
Now, in this past year, the past
six months, I finally learned
how to get like a slightly more
normal sleep schedule, but in
last year, I would just wake
up at 4:00 AM, and I'm like,
"Ah, this problem's solved."
Yeah, I remember.
Yeah, I was like you weren't
waking up at 3:00 AM in worry.
You were just waking
up and starting.
Yeah, it was like I
beat the worry problem.
Instead of laying a bit
awake, I'd just go to work.
And sadly that was, really
was my answer at the time.
Anyway, but, but when this
happens, like when this,
this spiral happens, and it
happens all the time- Yeah
over time I've gotten better
at doing something about it.
Now, the problem with the 3:00
AM one is that I'm not in a
position to do anything with it.
Right.
But if it happens at 3:00
PM, I'm like, okay, you know,
now I've got a better idea of
how to be able to take that
nervous energy and do something
with it, because at 3:00 AM
I can't do anything with it.
And if I were to go back and
I were to count- All of the
collective hours that I've
spent at 3:00 AM working
on problems, you take 365
days of the year, 'cause it,
it, not counting weekends,
I don't think about it.
Sometimes the
weekends are worse.
Yep.
Times 30 years or more, right?
Times at least one or two hours.
That's 10 to 20,000 hours-
Yes ... that I've spent- Well,
that's all it takes
to master something.
I looked at that
the other day and I
said, "Nailed it. Nailed it."
Dude, I look at that and I'm
like, holy cow, how could
you invest that much time in
anything and have negative
results to show for it, right?
Yeah.
And I'm not worried about that.
But I, I guess what I
have learned, what I have
learned is that all of that
energy is still energy.
In fact, it's pretty good
energy But not like, you
could put toward other things,
like literally anything else.
But when you're just, uh,
what you said a moment ago
just stuck with me, this loop.
Yes.
When you're just in this
worry loop where you feel
like worrying, like I was
doing at Comic-Con, is the
action, you lose every time.
But we spend a lot of time
doing it, you know what I mean?
Yeah, man.
But I think that's
exactly it, right?
Like, when it starts to
masquerade as problem-solving-
Mm-hmm ... those worry loops
become super toxic, super fast.
I have gotten to the point where
I realized, and I was like, "I
can't just make myself stop."
So I started looking for
replacement behaviors, and,
and the one that actually
worked well for me is a
little bit of breathwork.
So when I catch myself
doing that at 3:00 or 4:00
in the morning, I'm like,
"Okay, we're gonna box
breathe our way through
this," and it's just, and I
get into that loop instead.
And then before I finish the
loop, I inevitably just end
up falling back to sleep, and
that's been pretty helpful.
But I'm still surprised
how long it takes me
to realize sometimes.
A part of it's just like the,
you know, you wake up 3:00 in
the morning, you're not exactly
like, you know, super sharp.
You just wake up and you're
like, "Okay, what's going on?"
And it's really fascinating
to me, like it can take half
an hour sometimes before
I realize what I'm doing.
I'm like, "Oh my God, I'm
laying in bed, uh, acting like
I'm, I'm having a discussion
in a boardroom right now.
I'm not.
This is me by myself.
This is not working.
This is just worrying."
Yep.
"
No decision is gonna
come out of this."
Yep.
"There's no strategy here. This
is just endless rumination,
and it needs to stop," right?
But boy, does my anxiety
love pretending that it's
productivity- Yep ... and
try to convince me of that.
You know what's interesting?
You kinda mentioned this a
moment ago, but like at no point
in my life has it gone away.
So one of the things that, that
I always think is fascinating,
uh, with folks is that we
all believe that if we just
hit this milestone, that the
thing will go away, right?
The, the most obvious-
Yeah ... is money, right?
People are like, "Hey, I'm
broke now. If I was not broke,
my problems would go away."
There's some truth to that.
Where that gets lost is
that you don't understand
that that wasn't always
the core of your problems.
Right.
It was just a very
obvious manifestation.
I see this in
marriages all the time.
The husband and wife are
like, "Hey, you know, we're
having all these problems,
but it's about money." No,
money's the catalyst, right?
Uh-huh.
But if you had a ton of
money, you still wouldn't
like each other, right?
Like- Right ... what you don't
realize is money is just a, a
way for you to communicate that.
Yeah, said differently, if,
if you were having, if your
relationship was amazing and
you ran out of money, your
relationship wouldn't break
just because of that, right?
Correct.
Right.
The,
the converse is true as well.
And so, uh, again, having
been on both sides of the
have money, uh, spectrum,
I'll take the have money over
not having money- Yeah, yeah,
yeah ... any more than you
can afford these outcomes.
But I gotta tell you, man, when
I was 19 years old starting a
company, a CEO of a company, and
I was dead broke- I was awake
at, at, at 3:00 in the morning
having the same thoughts- Yeah
that I do over 30
years later, right?
Yeah.
Now, the context of
them has changed.
Whereas like when I was 19,
and I'll use this as a bit
of an analog, I guess, for
first time founders, right?
Yeah.
A lot less to do with age
and a lot less to- more to
do with inexperience of doing
this, the startup thing.
I think for a lot of folks,
they're like, "Well, if I knew
more about what I was doing,
I'd have more confidence.
I would have, you know, uh,
more certainty about it." It
kinda goes the other direction.
Yeah. Which is like now at
3:00 AM when I'm worried about
stuff- Yeah ... I'm like,
"Dude, what sucks is I actually
already know this stuff.
This isn't like a-"
Yeah ... question of
my credibility anymore.
Like, I know this stuff cold.
Right.
And I'm still worried.
Still worried.
No, man, to me it was like
the, the more I know about
something, it's kinda like
juggling knives, right?
If I don't know very
much, I'm kinda playing
around with one knife.
By the time I know a lot
about it, I'm juggling
a whole bunch of knives
at the same time, right?
It just, it seems to get
progressively worse, and I
think part of that is like
the more you learn about
something, the more you realize
how much more there actually
is to learn about it or-
Yeah
...
how easy it is for
it to go wrong.
When you don't know,
you don't know.
Like, ignorance truly is
bliss in so many ways.
Building on that, so in a
lot of cases, like saying,
"I don't have money, but
money would solve it," is a
really nice way to close the
door on that problem because-
Yeah ... hey, it's something
I don't have, but when I do
have it- Yeah ... the problem
will solve itself, which is
almost like, like literally how
everybody thinks about money.
They're like, "Ah-" Yeah ... "if
I just had money, I would
be happy." Like, you'd have
less of those problems, but
you're gonna introduce new
ones, and if you were a shitty
person before money, you'll
just be a shitty person with
more money later, right?
You're like, oh, you know, um-
Just a rich, shitty person.
Exactly, and I think one of
the, the biggest challenges
people have in life when it
comes to wealth and things
like that is it's so easy
to say that I don't have it.
So again, when they say, "Well,
when I did have it, I would have
this problem paying my mortgage
or paying my, my landlord-" Yeah
... or whatever," that is true.
But for you to think that
your brain just stops having
problems is pretty wrong, right?
And so when I look at myself at
two different moments in time,
like 19-year-old Will and, and
51-year-old Will, it is shocking
how common, like, my base set
of issues still is, right?
Yeah.
How, like, kind of
nothing has changed.
Like, I've got far
more experience.
Like, I've got that, that meta
experience where you've gone
through the problem before and
you're like, "Okay, I have the
experience of the problem,"
which is unique, right?
Yeah.
Like the equivalent of like,
I've gone through a divorce,
or I've, I've gone through
a company shutdown, or
I've gone through whatever.
Yep.
Yeah.
Like having the experience of
having a full life cycle of a
problem is incredibly powerful.
However, it still sucks.
Yeah.
It still, it still goes through.
And,
and honestly, like I can
think of at least a couple
scenarios where by having been
through it before actually
gave me more to worry about.
Well, like if they didn't
end well the first time.
Like, that's what
killed my first startup.
Shit, here it
comes again, right?
Yeah.
There you go.
Yeah.
Because you've been through
that before, and it ended
that way, doesn't mean you're
gonna do better with it.
Or just like some of it's
probably just PTSD, right?
Yeah.
For sure.
Yeah.
It's like you've
been through this.
You know what a pain in the
ass it was to solve and how
much work it took, and that
it didn't really make anything
great at the end, it just wasn't
as much of a problem anymore.
That can be really hard.
I think part of the bliss of
ignorance is like if you know
you have to go run a marathon
and you're barefoot and all
you can see is broken glass
in front of you, and you know
how long a marathon is, it's
gonna suck the entire time.
If somebody's just like,
"Run," and you're barefoot
and there's glass in front of
you, you're just like, "Well,
I guess I have to do this.
I'm gonna run." I- there's
something about sort of
knowing the difficulty,
uh, that can actually make
things significantly worse.
I get that.
And of course, knowing the
difficulty, we alway- we've
talked about this before on the
podcast, like we can inflate
those things too, right?
Also, the, the remembrance
of the thing makes it way
worse than the, than the
reality of it sometimes.
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 day
long at 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.
So we've got this wave of
anxiety, this wave of worry,
and we're trying to figure
out what to do with it, right?
Yeah.
We know it's bad, right?
There's no, at 3:00 A.M., like,
"Man, I should really kinda
like, like triple down on this."
Like we know it's, it's bad.
So at some point I started to
figure out like that even though
this was worry It was energy.
Yeah.
And it was a manic
level of energy.
Here's what was interesting.
It was a manic level of
energy that I also felt
when I was super excited
about doing something.
Yes, e- exactly.
Nearly one-to-one, man.
Like, the feeling
is almost the same.
And so, uh, you know, kind
of this, this fear and
greed mentality, right?
I think we all agreed that
the fear one's a lot stronger,
but that's where I thought
it was interesting, right?
I was like, "This is
quite a motivator," right?
Now, not the one that I want.
I wish I could have a
cool- Right ... like, like,
like fun motivator, right?
Yeah, yeah.
But this was more of a
survival instinct motivator.
Yeah.
And
I thought about it for a while.
Still a very powerful feel.
I worried about it at 3:00
AM and, and I, and I thought
to myself, "How can I use
this energy, this negative
fuel burn, if you will,
right?" Towards something
that will actually help.
Now that's where I fucked
it up the first time, right?
I was like, "Let me jump
out of bed right now.
Let me run down to my
computer- Yeah ... and let
me take action." And that
generally didn't work.
And what it didn't do, it
wasn't bad necessarily.
It was, it was on
the right track.
I was trying to use that
energy to, to respond,
but I was just worrying
in a different way, right?
Like, like I was just... I
remember the big thing was I
would jump out of bed and be
like, "Our AdWords budgets
aren't performing, so the only
way that I can fix them is
to jump out of bed at 3:00 in
the morning and run downstairs
and fix them right now."
Yeah.
And there's some truth to that.
There's probably something I
did, and I tweaked a budget
and changed a landing page or
something that might've helped.
But what was interesting was
I also did this other thing
where I said to myself, "What
is something that I could do
that is productive- Mm ... that
isn't this problem," right?
Yeah.
I'll give you some examples.
Some people say that when they
clean, like reduces worry.
Oh, yeah.
Cleaning, organizing.
Yeah.
100%. Just something to get
rid of that manic energy.
Yeah.
Yep.
And, and some of the, the...
What I found, I kind of pulled
that thread a bit, and what
I found, why so many people
gravitate toward cleaning and
organizing is it helps you
accomplish something positive.
Yep.
Right?
Like, so you can look at a
room that's- It's finite.
Correct.
You can look at a room that's
unclean and make it clean.
Yeah.
Right now with your problem,
whether it's a work problem or
otherwise, you can't finish it.
You can't make it clean.
There's no short-term
mission accomplished thing
that's gonna happen, right?
Correct.
You can't get to any point of
like concrete resolution, so
it just stays self-destructive.
And all of a sudden,
that cortisol that you're
dealing with switches to
dopamine, where it- Oh,
yeah
...
it's, it's a positive
hit to say, "Hey, I
did something right."
Yep.
And so one of the things,
this is just for me, I'm not
sure it applies to anybody
else, and you and I've
talked a lot about this.
It's why I got into carpentry
and woodworking- Yeah ... is
because I could finish it.
I could be like super stressed
out about something, and I'll
be like, "Okay, look, dude, I'm
just gonna focus on cutting this
board." Like, like all I have to
do is cut this board properly.
That's it.
It's all I need to do.
And I would do it, and I
would cut it properly, and
I'm like, "Fuck yeah," right?
Like just something to feel
good- Mission accomplished.
Done.
Right?
Just something to feel good.
Done.
Yeah.
And it's not gonna
change my life.
Yeah.
But I think that there's a,
uh, like a mental pattern
Where I start to realize
that my energy's going
into worrying, right?
It's not going into
productivity, it's
going into worrying.
So no matter how much more I
invest in that bucket, it's
going to be totally wasted.
Yeah, it's not gonna change.
I think it's gonna come out...
It, it's funny, like I, I, I
think about this in terms of
kids, Will, and I'm, I'm sure
that you, you can probably draw
some parallels here with Will.
I'm thinking of Jack in
particular, um, which is
like when they have that
crazy manic energy, right?
You can't get them to calm down.
You gotta give them
something to do, right?
And it's the same
thing with, with us.
We don't have to
kill the energy.
We have to give it a
meaningful task, right?
Something that will actually
do something with it.
So I-- going back to the thing
I said before around like
specifically the, the middle
of the night wake-ups, right?
Like for me, I don't wanna give
it another task at that point.
I do wanna try to redirect.
I wanna, I wanna
save that energy.
I wanna channel it
the next morning.
Kind of bouncing back to some
of our earlier discussions
today, Will, around like...
And here's how I restart Claude
in, in a new chat, right?
So basically, I, I do the
human version of giving myself
a markdown file so that I
can wake up in the morning
and pick up where I left off.
And that's why I'm trying to
use the breathwork and things
like that to just like put
that situation on pause, right?
Maintain that energy, save
it for tomorrow morning,
knowing that the minute I
pick that up again, that
same level of manic energy
is gonna come back, right?
Because the problem won't
have changed overnight.
Uh, the only difference is
I'll be working at a time
where I'm fully energized,
actually energized, and I
won't risk waking up my entire
household stumbling around in
the dark saying, "Computer."
So just as a note, uh,
when I saw you last
time, uh, in person, you
mentioned the box breathing.
You said, hey, what you've
been doing at night is
the box breathing, right?
Yes.
And so I agree with you.
I have found that
the box breathing has
put me back to sleep.
Like I- Yes.
There's no question, right?
I also find that because I
have such insane ADD, what I
try to do is I try to count my
full cycles of box breathing.
Yep.
And I get to one, sometimes two.
I don't think I've ever made
it to three before my mind
erases to somewhere else.
Like it's- Somewhere else.
Yeah.
Yeah, like I cannot maintain
that level of concentration,
which is why meditation
was useless for me.
Try to switch to an asymmetric
one so that it's not like
four, four, four, four.
If you do something asymmetric,
then it gives you a little
bit of change in between.
Yeah, I agree.
It makes it a little
easier to remember like- I
agree
...
where am, am I breathing in?
Am I breathing out?
Am I breathing at all?
Am I about to kill
myself, right?
But the other thing that I
found a useful technique is
that I focus on gratitude.
Uh, this solves a few
things for me, right?
And what I do is I go through
what are the things I'm most
grateful that today, right?
Now this is, this is a good
exercise no matter what, but
let me explain to you why I use
it at, at 3:00 in the morning.
It's a reminder that I
do accomplish things.
It's a reminder that like my
life is okay, even though this
problem- Yeah ... whatever that
might be, is present, right?
And it's just a good way
to kinda center yourself.
I mean, gratitude is of
course, always a good thing.
We do a thing, uh, in my
family at the dinner table.
We do a round of gratitude.
Uh, and it's phenomenal, right?
Like- Yeah ... to hear what
comes out of your kids' mouths
and what they're grateful
for, and my kids are just
incredibly grateful, but also
just really kind kids, I know
yours are too, is unbelievable.
And I bring that up to say
I try to remind myself that,
like, my gratitude- Agrees, yeah
... is also their gratitude.
Like, the things- Yeah,
yeah, yeah ... they're
grateful of, I help enable,
and I, I try to make sure
I don't lose sight of that.
But part of my, like, you
know, dealing with worry
is a reinforcement that I
also solve problems, right?
Yes.
Like, yes, this is a problem,
but- And you're good at
it ... I've solved like
20 problems today, right?
Right, I think that's, I think,
so that's where I was getting
ready to go next actually-
Yeah ... was that one of the
things I've started trying to
do is, is say like, "Why am
I allowing, like, the panic
intern in me, as opposed to the
experienced founder in me- Yeah
drive this conversation," right?
Like- Great way to put it.
Great way to put it, yep ... I
can choose the narrative
here, and so I, I've tried
to become better about that
too, just the self-talk, man.
I'm a huge believer in it.
Like, how we describe things
in our own mind have a lot
to do with what happens next.
Yep.
And so I'll tell myself,
like, "Yeah, wow, this is a
big problem. That is, that's,
that's awful." I literally
talk to myself like I'm
talking to one of my kids.
Like, "Oh, that must be really
frustrating that you're dealing
with that right now," like,
and then it's like- ... "Well,
but you've solved problems
like this before, haven't you?
Oh yeah, and you're pretty
good at that, and you feel good
when you get through it, right?
Okay, cool.
You think maybe we could
put this off until tomorrow?
You do?
Okay, awesome.
Let's go back to sleep.
Box breathing time." Yeah.
Right?
And it's funny, the shit works.
It really does.
But, but you have to have the
recognition of it first, and I
think e- especially for early,
early stage founders, first time
founders, you don't yet have
enough reps with it to where
that, that conversation's even
gonna make any sense to you.
You're just gonna wake up
worried and be like- Agreed
... "This is what I do. I'm
just gonna worry. I'm gonna
worry myself into a-" Yeah.
The problem is worrying
gets in the way of solving
the problem, right?
Correct.
And again, i- w- we talked
about this a moment ago,
but like there's a bucket of
worrying and there's a bucket
of problem solving, and I think
worrying often masks itself
as problem solving, right?
It reminds me of like when a,
um, a boat's about to sink.
And you have people running
around, you know, like,
"Oh my God, it's gonna
sink, it's gonna sink." Um,
they're gonna die, right?
The people who are gonna survive
are like, "What can I use here
to build a raft out of?" Right?
Yeah.
Like, that's problem-solving.
The other is just worrying.
Yep.
Right?
Only one of you are
floating out of there.
Yep.
Yes.
And, and I, I try to think
of that in terms of where am
I putting my time right now?
Is this worry just me running
around the, the deck of
the ship- Yeah ... "Oh my
God, we're gonna die," or
is this me saying, "Hey,
I've got a, a really good
plan I'm about to execute"?
Any danger there in activating
yourself to say that, like,
you just go into that always-on
mode where it's like, "Okay,
here's a problem now. I
can't just worry about this.
That would be useless, but
I also go, have to go do
something about it even though
it's 3:00 in the morning."
How do you balance that?
The problem with that is,
for what it's worth, I do
not get out of bed, right?
So that it, it isn't one of the
things where I'm like, "Fuck
this, I have to, like, go,
go do this now." I'm at least
mature enough in this thinking
that I know that the only
solution is I need more rest
in order to solve this problem.
Now that said- Yes ... that
argument does not sound very
strong at 3:00 AM, right?
No,
it doesn't.
It,
it doesn't.
I feel like if I could just take
action with my thoughts right
now, I'm basically trying to
compartmentalize my problems.
In other words, I'm not trying
to like, like, push them
away, like, hey, I shouldn't
have problems anymore.
Yeah, yeah.
I'm saying, here's stuff I
can solve right now, like,
here's stuff tomorrow morning
I can solve, and here's stuff
I can't solve anytime soon.
And I think this is interesting
because, you know, you've
been on, on this journey
with me in, in building a
company, but also in, as
I've been building a house.
And I'll use the house
metaphor just 'cause it's
very clear for people.
Right.
Like, I can fix one thing in
this house today, you know,
as I'm building the house, but
I can't fix the whole house.
No matter how badly- Yeah ... I
want to, tomorrow I can
only make one thing right.
Maybe two if things go crazy,
but generally only one.
So let me focus on that.
And whenever I do that,
whenever I focus on the one
thing, it changes everything.
'Cause number one, I t-tend
to get it done, and it, it
releases that dopamine, right?
Like you feel less helpless.
Yeah.
So it's like the, again,
the ship is going down,
and you're like, "I gotta
build a boat," right?
And it's like, okay,
I found an oar.
Not gonna be super helpful
without the rest of the
boat, but I am gonna
need the oar, right?
So I got that thing done.
Yeah.
Now I'm gonna find the next
thing and the next thing.
And I think when you get
into this highly rhythmic,
very specific problem-solving
chain of events, incidentally
problems get solved.
But more importantly, it puts
your focus on something you can
actually do something with- Do.
Yeah ... you know, versus
just messing around.
Yeah, I mean, look, I think
worry is part of the founder
job description, right?
I mean- ... kinda the whole
point is that we detect risk,
and so, you know, we don't
necessarily wanna disable any
of that, but we do have to
learn which alarms are worth
paying attention to, right?
Yeah.
And I think trying to,
trying to turn things from
just endless worry to useful
concern is sort of the goal.
But you have to have, and
I think you've, you've done
a good job building these
systems, uh, you know, these
mental models, 'cause you
gotta have... Without an action
protocol, that worry is just
always gonna be there, right?
And it just, it ends up
being this, this constant
infernal internal noise.
But yeah, I think over
time it becomes a lot more
obvious and a lot easier.
But telling a founder not
to worry at the early stages
is kinda like telling a
smoke detector in a fire
to, to just relax, right?
It's like my, my whole job
is to just scream about this.
This is all I can do.
That's what I have to do.
That's what I'm here for.
But I think part of that,
though, is the size of the
problem is proportionate to how
likely we are to solve it, okay?
Yeah.
So if we say that the problem is
that this company, you know, is
never gonna raise money again.
Okay, I understand.
Yeah.
Like that's, that's a
very common problem that
everybody deals with.
Fair enough.
But you can't
solve that problem.
Not today, not with,
with one fell swoop.
But here's the part
that you can solve.
Tomorrow morning you can wake
up and you can research five
potential investors to contact.
Next, you can write an email or,
or find a warm intro or whatever
to contact those five investors.
Collectively, you cannot
solve fundraising, but you can
solve five investors, right?
It's that whole, you
know, how do you move a
mountain one pebble at
a time, uh, type thing.
It's the same way I
built a house, right?
Built a giant house-
Yeah ... by myself, right?
Not literally, but pretty much.
And not because I just looked
at the whole thing and said,
"Oh, I'm just gonna build
this whole thing myself."
It's like one thing at a time.
Yeah.
Like one little piece at a time.
But
it adds up.
It's a, it's
a collection of lots
of tiny problems.
Right.
Yep.
So when I'm going through that,
that 3:00 a.m. exercise where
I'm worrying, you know, that
being just kind of a metaphor
for all worrying, my first
thought is What is the smallest
morsel of this problem that I
can take action on right now?
Now, part of that is
'cause I'm a get shit
done kinda guy, right?
Yeah, yeah.
Actually, we just went through
this exercise 12 hours ago
when we were talking about,
like, we were doing our landing
page funnel, and we were
saying, "Oh my God, there's
all these points in the funnel
that we wanna change." And we
were like, "Yeah, but until
we fix the first one, the
rest of them don't matter."
Yeah.
The rest of them don't matter.
Right.
Yeah.
If
nobody makes it past the first
page, who cares about the
second?
We don't, we don't need to worry
about hanging the windows on
the second floor if we haven't
built the first floor yet.
Exactly, right?
Part of that is a great
decades-long conditioned
response by me, right?
Yes.
Like, I've learned that I
can't solve the big problem,
so I have to chip away at it
with small problems, which
incidentally is kinda how you
tend to solve big problems.
Not because you worried
about them so much, but
because you freaking did
something about them.
Yeah.
Actually took action.
Yeah.
Look, we're not gonna
start, stop thinking
about our startups, right?
Right.
That's just not how we're wired.
Right.
And frankly, some of that
obsession is why we're
able to build anything
in the first place.
Right.
Right?
But we do have to stop
pretending that worrying
is the same as working.
To me, the worry is
not a silent brain.
Right.
It's, it's a trained
brain, right?
Right.
It's one that can spot the
fear, try to sort that signal
out from the noise, and turn
all that nervous founder
energy into something really
useful, which I think is the
actual goal behind all this.
And kind of both, both of
us are here to say it works.
Like, it's very doable.
It does.
Not easy.
Like anything, like
we're doing it easy.
Yeah.
Simple,
not easy.
But exact- That's a
great way to put it.
But I think the way we look at
this is like, look man, a lot of
people like will say, especially
not founders, they'll be like,
"Oh, you shouldn't worry. You
should worry about, you know,"
like, uh, you know, 'cause we're
like, dude, not gonna happen.
I think this is also maybe
like a point of my maturity
is that- For the first time
in my life, I'm realizing that
things aren't gonna happen.
Like 10, 20 years ago, I might
have thought, "Oh, I just need
to be more zen and meditate
more, and, you know, I'll
make these problems go away."
Yeah.
And now I'm like, you know what?
What a crock of shit.
Yeah.
Like that was never
going to happen, right?
Yeah.
It's the, the
six-pack abs theory.
Well, if I just diet more
and like hit the gym more,
I'll just have six-pack abs.
Never gonna happen, right?
Yep, yep.
Like that... I'm sure
that's true, and it's
never going to happen.
It's never gonna happen.
Yeah.
Right?
And I think that when people
look at our lives, you know, the
outside looking in for founders,
they're like, "Well, I go home
at night and I don't think about
like whether my business is g-
is gonna be around anymore."
Yeah, 'cause it's not your
freaking job to do that.
That's like saying, "I
don't worry about kids
'cause I don't have any."
Right.
Yeah.
Well, g- good.
It'd be weird
if you did.
Yeah.
It would be weird.
But like I look at it and I'm
like, man, if you had to deal
with what I have to deal with,
which means I have to go, go
on the, the dealership lot
and worry about every single
thing that's happening- Yep
it's like quite literally
my job, then look, man,
worrying's gonna come.
That's part of it, right?
And that's okay.
It's hard, but it's okay.
It, it's what we do.
But I think what we can do
differently, and I think
this is the turn for all of
us as founders, what we can
do differently is we can
say, "Hey, you know what?
Every time I'm gonna
worry, I wanna master that.
I wanna get great at that.
I wanna be the grand wizard
of worrying, because when
that happens, I'm gonna look
at that as that Super Mario,
I just hit the, the mushroom
and just expanded, right?
I am the best version of
myself when I'm in that mode.
If I can learn how to control
it, if I can learn how to
focus it, 'cause if I can,
all the stuff I'm worrying
about becomes a superpower
to actually get it done."
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