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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