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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 their 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, we've
had very, very interesting
relationships with our startups,
with our work over the years.
It's necessarily what
I would call healthy.
We poured a lot of time
and love into them, and.
Sometimes they've given back
to us, but I don't think we've
ever really truly demanded
much back from our startups.
But that's not necessarily
true for everybody else.
Right?
And so I think we gotta talk
about like the difference
between being a founder
and and how to balance
some of that stuff out and
kind of what it looks like
for the rest of the world.
For example, you ever
called a friend at two
o'clock in the afternoon,
like Tuesday to find them
floating in a pool and just.
Found yourself incredulous.
I remember I told you this
story after it happened.
This was like a year ago
and I'm driving home.
Actually it's funny, I was
driving home after teaching
the entrepreneurship class at
my, my kid's school and I was
calling a friend of mine 'cause
he was kinda like on route
to where I was headed next.
And I was two o'clock
on Tuesday, a beautiful
like summer, afternoon
or spring afternoon and
I'm like, uh, hey man.
What you up to?
He's a senior executive at a
public, uh, technology company.
Right.
And he's a sales executive.
Right.
His whole life he has been
on the ground selling.
Right.
Like, he understands performance
metrics better than anybody.
Well, except when he is in the
water, uh, not selling well.
Okay.
So, so he's also one
of my oldest friends.
And, and so I was like, Hey
man, what are you doing?
And he said, uh,
I'm in the pool.
I'm like.
Huh?
Uh.
Like, what do you mean?
He, he is like, yeah,
I'm sitting in a floaty,
floating in my pool.
I'm like, and this is, this
is what's so funny, Ryan.
I was like, how?
I was incredulous.
Yeah.
Like how could you Possibly at
two o'clock on a Tuesday, right?
When there's work to be done.
Yeah, there's work to be done.
Why depend on you,
sir.
And so my first thought
was to fire him.
My second thought was that
it doesn't work for me.
It doesn't work for me.
Yeah, I can't, I just go throw
him a cinder block in the pool.
But here's the best part.
Here's the best part, like,
and again, I've got a great
relationship with, I've
known him for a long time.
My response was kind of
like, I. How, like, how
could you possibly do that?
And, and this is all he said,
he goes, makes me happy.
It makes me happy.
Like, and, and oh, just thanks
for making it worse right now.
Now I really don't understand.
Found.
I was like, that's
the worst answer ever.
Right.
And, and again, I'm, I'm
telling this story to
set the premise here.
Of what a toxic relationship
with work looks like.
And we're not talking about his,
we're talking about mine, right?
Like it didn't occur
to me like first blush.
Again, I'm, I'm not that
like one dimensional, but
it didn't occur to me that
you could just do that.
That you could just be sitting
on a Tuesday in the middle
of the work week in your pool
'cause it made you feel good.
I was like, there's gotta
be some business purpose
to what's going on.
Right?
And that's where
our story begins.
We dig deep enough into it.
You can find that, right?
Like, I think as, as
founders, we often
conflate hustle with value.
And you know, we think if we're
not, if we're not chained to
our lap to 24 7, we're slacking
and not the kind of slack
where we're, we're talking
to the rest of our team.
Not that slack, like just
the not doing anything
kind of slacking.
Guess what, like, productivity
can be floating in a pool at
2:00 PM if it recharges your
brain, if it gives you the
energy you need to go back in
and, and do the things right?
Like we know what the, the,
the cost of burnout is.
This is the cost of the
therapy that keeps us from
getting there, I suppose.
Yeah.
And you know, one of the
things we do a lot of.
On this podcast, 300 episodes.
I mean, like, you know, we've
almost, man, it's like 2
97 or eight or something.
Oh
damn.
I didn't realize
it was that close.
I just we're real close.
I rounded it up for charity.
When I think about, you know,
all the topics we've covered,
and some folks know this because
some folks that listen know us.
Most of what we talk
about here is a reflection
of our own journeys.
This is Ryan and I in our
own therapy, the startup
therapy we're generally
talking about Is ours ours?
So,
and a lot of people
will comment.
They'll say like, Hey, it just
sounds like I'm in the middle
of a conversation of two people.
Like unpacking
something between them.
It's 'cause you are, that's
actually what's happening.
Do you remember back like,
this is 20 17, 18, somewhere
in there where we were like,
we should do a podcast,
and then we were like.
What should we talk about?
And we went through all
kinds of iterations, like
start up daily, we could
cover some news, we could
do all this different stuff.
And then finally we're like,
you know, what about those
conversations we have every
week anyways, where we're
just talking about like,
what are you going through?
What are you going through?
How are you dealing with it?
What have you been through?
Yep.
And we're like, what
if we just hit record?
Yep.
And then we did.
And so here we are.
So to your point, it is very
much just listening in on the
conversations of two people who
live through this stuff daily
in the ironies.
If you listen to this long
and they're like, man, those
guys really need therapy,
which is totally true.
Not anymore.
Yeah, yeah, exactly.
On a weekly basis.
I say this to, to set the tone,
to say a lot of this isn't us
talking down to founders saying,
here's what you're doing wrong.
This is in real time, saying
this is what we're doing
wrong, like right now.
Right.
And the self-awareness of it,
of being able to say, Hey,
you know, something's broken,
doesn't make it go away.
I wanna start there.
For me, I'll just kinda
point to myself here.
I've spent the last 31 years
in a very specific kind of
mindset, which is if I'm
working, I'm valuable And okay.
And if I'm not working,
I'm guilty and not now
that is wildly unhealthy.
I just wanna be clear.
Right.
Wildly unhealthy pays well,
but it's wildly unhealthy.
You said
this before, but it's,
it's, it was fear.
Motivation.
Yep.
Right?
Yep.
And, and, and it's
about safety, right?
Yep.
So for you, it's like,
if I'm working, I don't
have to be afraid because
it creates safety for me.
Right?
So as long as I'm
working, I'm safe.
Hundred percent.
Yeah.
I
mean that's, that's
a lot to deal with.
It is, right.
It's a, it's a hell
of a lot to unpack.
I think what we build
up with that is a
tolerance for discomfort.
Oh yeah.
Right.
In, in so many ways.
So in the way my buddy
is floating in a pool and
he's saying, Hey, I am not
comfortable at work right
this minute, I'm gonna go
do something comfortable.
My res response to, to
not enough comfort is work
more because that will
somehow create more comfort.
And sometimes it does.
Right.
But I guess what I'm
saying is if we zoom out.
As founders and we say,
Hey, is my relationship
with my startup healthy?
Ergo Sure.
Does it pay me back in
more ways than cash?
As much as I put into it.
For everybody listening,
like I'd say 99% of you
can listen to this and me
just say, probably not.
Yeah.
There's gonna be a few of,
you're like, no, I actually
have a very, very healthy
relationship with this.
Yeah.
Most of us don't.
For those of you that do,
please create a podcast, Ryan,
and I would love to listen to
it and take, I'd love to, can
follow along and do what you
do.
Yeah, just send me a note
that tells me I'm wrong.
That'd be great.
But for kind of everybody else,
I think part of it is because
when we go into this, Ryan, like
when we start something, you
start something from nothing.
It is, there's a voluminous
amount of weight in
work and commitment,
discomfort and frustration.
I think because we come to
expect that it builds a pattern
behavior where we just assume.
That's how it always has to be.
It's essentially starting in an
abusive relationship and using
the abuse as the baseline for
how the relationship works.
That's how it
functions.
Yeah.
You know, I think, and
again, look, there's, there's
reasons for all this, right?
Part of it is that when
we breathe life into
something new, that's it.
We're literally
breathing life into it.
Without us, there isn't anything
at the idea stage, even at
the early operational stages.
Without us, it
doesn't do anything.
It's as if we're, we're
constantly having to
give the business CPR.
Yeah.
And if we stop, we know
exactly what happens.
Yeah, yeah, exactly.
There comes a point at which
that's no longer necessary, but
man, the muscle memory is built
at that point and we've wrapped
our entire being up in being
the thing that keeps it alive.
That's just a matter of momentum
and being able to recognize that
momentum going like, okay, it
actually can survive without me.
But man, that's a, that's
a tough moment to spot.
Part of it too is
it's all consuming.
There is no startup that
won't just consume all of
you if you let it right.
It is endlessly hungry.
If IPO decide to spend 16
hours straight today at my
computer, at my desk working.
The startup will
consume all of it.
The startup will never tell
me, Hey, it's time to go home.
The startup will never tell
me, Hey, you're pretty tired.
You should probably
go, go get some rest.
Right?
The startup will never tell me,
you do, you know, you're, uh,
developing a terminal disease.
Yeah.
Because of this.
Right?
Like, yeah, n none of
that will ever happen.
The startup will consume as much
as we give it, and that's where
the danger begins because we
start to believe that because
it can consume all of our
time, it should consume should.
All of our time.
Exactly that.
And it, it took me a
long time to start to
understand that balance.
Ryan, you said something, uh,
earlier when we were talking
today about how you and I
both hit the same kind of
milestone in starting families.
Yeah.
Where all of a sudden
something greater than
us became that voice.
What was it like for you?
Yeah, same thing.
You know, like I think you,
you said something that ties
directly to this, which was,
we have a high tolerance
for this kinda thing.
Like we have a high tolerance
for deferring happiness, for
deferring joy, for deferring
time on ourselves and just
accumulating maladies of,
of physical and mental and
emotional states and, and
foregoing relationships
doing all this other stuff.
But at some point when we
became partners to wives
and fathers to children.
All of a sudden I have
four other people's
tolerances to consider.
Are they as tolerant of my
ability to just sit at this
desk and pour myself into a
monitor for 18, 19 hours a day?
The answer is no, they're not
right at, at the point at which
I realized it was costing them.
And there are times where
like yesterday, right?
Yesterday I took off at like two
in the afternoon my time for a
couple hours to go pick up my
daughters, take them to a soccer
match, watch them play, and
then I get them back to school.
And then I came back to
the house and continue
working at some points.
In the past, I think I still
didn't really realize what
all the costs of that were.
Yeah.
I was like, you know, you, you
think about the fact that like.
I dunno, whether it's,
whether you miss it or you
know, they're gonna miss it.
And whether that it's either
guilt or just a fear of missing
out or a combination of the
two kind of doesn't matter.
But over, over time, I've
started to pay more attention to
the fact that like it costs them
something when I don't do that.
Right.
Right.
And so, right.
And you don't get it back.
You don't get it back.
You don't get it back.
Right.
And so I think being able to
make those trade-offs right,
and I think the, you know.
It's interesting, but you,
you said something else that
ties directly to this, which
is that it's really hard
for us to see those things.
We will just continue to go
and push and do, and we don't
necessarily notice in our own
lives what you had so that we
have to look outside, right?
Mm-hmm.
So whether it's your family
or not, or you call a friend
and find them floating in a
pool at two o'clock in the
afternoon, a Tuesday, the fact
that we can't relate to someone
else enjoying their lives,
just for the sake of that.
Probably our
problem, not theirs.
Oh, absolutely.
Absolutely.
And again, and we
need those lenses.
Even while it was happening,
you know, I, I said to my
friend, a again, he's known
me for a very long time, and
he is a good sounding board.
And I said, you know, I'm
laughing about this because
I know how ridiculous it is
that I have a problem with it.
And I said to him, I was
like, if it were me, I
would, I would be firing
you right now on the phone.
And I was like, but at the same
time, I also know you're right.
Right.
Yeah.
Which is, which is even harder.
And I think part of this
is getting to a point where
we stop and take stock of
what our values are, like
what's important to us.
Yeah.
Just like you said with your
daughter and you say, these
are my non-negotiables.
Right?
These are the things that
if the startup takes these,
it's not okay anymore.
It's, it's not.
A lack of having those
things really laid out.
Laid out in, in very
big, bold letters.
You and I have talked about this
on previous episodes where we
sat down early in the process of
building this company and said,
these are our non-negotiables
and to our what work with jerks.
Right.
We won't work jerks.
Right?
Yep.
And when we get to Jerky
Town with someone, we're
like, you know, you've
never been worth it.
Never been worth it.
And every single time we
were like 10% sure that this
might be a good decision.
It was always a hundred
percent a good decision.
Yeah, right.
Hindsight it was
always like, yep.
And the, the only thing we ever
questioned was why not sooner?
Why not sooner?
Right.
And to be fair, those very
same people go home and they're
like, those guys are jerks.
By the way, they're also right.
Not 'cause I think we're jerks,
Ryan, but because you know,
they look at it, especially
if you're being let go as
how dare them, et cetera.
Right.
I was performing
even though I was a jerk.
Yeah, yeah.
So why would they, they
should have tolerated it
again.
Again.
And so, and that's one of them.
Another one is, and you touched
on this, our ability to be able
to say, what's my commitment
to, let's say my family?
Mm-hmm.
At what point have I given too
much or could I give too much?
Yeah, and the fact that you
can look at the soccer game
and say, Hey, I get that.
I could, I could avoid this.
I, I could not go and
the world wouldn't end.
However, this is also one of
the things that draws the line,
that's to what my values are.
And if, if I don't go, and
again, it'd be different,
Ryan, if we were right in
the middle of closing some
major deal and there was
some make, or you're creating
a whole other consequence.
But fortunately we're not in
that position where we have
some kind of consequence.
But like I think for me, I have
this overarching consequence
of success, of responsibility.
You know, things like
that, that I can easily
let Trump, everything, that
excuse can easily apply
to 16 hours of my day.
I have to forcibly
talk myself out of that
excuse for every minute.
I don't spend with that
excuse, if that makes sense.
Yeah.
Yeah.
No, it's, it's exactly
the same for me.
It's, it's the, the calculation
is always in, in that order.
My default is be here for a
lot of hours and do as much
as I can or more than I can.
Yep.
And just keep doing, and you
have to talk yourself out of it.
I think where it came
about, you talked about
some non-negotiables for me.
I've got a couple,
like, one that's just
super personal is sleep.
I don't mess with it anymore.
Right.
I try not to.
My, my system's been messing,
messing with itself for the
last couple weeks, but like
I try not to mess with sleep.
Sleep is so important 'cause
I'm way better all day when
I have the right sleep.
The other one, and this is
something that I think I've
been doing a fairly good job of
for a couple years now, but I
just read something a few weeks
ago that reinforced it from
a, a, a childhood psychologist
that said, your kids need you
on their time and their terms.
Right.
You can't say, oh, you
wanna talk about that?
Well, I'm busy right now.
We'll talk about it later.
It doesn't work.
Right.
There's a real cost to them
in so many ways because
the fact it was important
then is why it's important.
And so I've really tried to do
that and just say like, look,
I can run to catch up on work.
I can, I'll bend my sleep.
Right?
Yeah.
If I have to, right?
I will sacrifice that personally
so that they're not forced to
sacrifice something at during
their, you know, important
years of personal development.
I've taken it a step
further where I've applied
it to my wife as well.
If she needs something,
she gets it then.
Right?
My kids need
something, they get it.
Then the way I analogize it
to myself, 'cause for me the,
the going back to my early
soccer days always helps.
And I said, you know what?
It's like having to run
outta position to cover
somebody else, right?
It's the right thing
to do in the moment.
Now I know I'll have to run
extra hard to get back to my
position to make sure that I'm
not letting somebody else down.
But if, if I gotta go
cover somebody's spot.
I gotta get over there because
the cost and the consequence
of that is immediate.
The cost and consequence
of me being out a position
is something that happens
later and I can do my
best to deal with it.
Right?
And I think that as
startup founders, we're
pretty good at being able
to run fast to catch up.
You know, something that's
really funny about
everything we talk about
here is that none of it.
Is new.
Everything you're dealing
with right now has been done a
thousand times before you, which
means the answer already exists.
You may just not know
it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems all
dayLong@groups.startups.com.
So if any of this sounds
familiar, stop guessing
about what to do, let us just
give you the answers to the
test and be done with it.
We, there is no point
within my work week, the
Monday through Friday.
Yeah.
Where I ever feel.
Like, I am justified for
not working and I'm not
comparing this to yours.
What, what I'm saying is it's
one of the things I spend a
lot of time thinking about.
Lemme give you some, some
also how I, I mitigate that.
One of the things I do, uh,
and we've talked about this
in previous episodes, is I'm
hyper specific about what
needs to get done today.
Because if I'm not, if I don't
say, here's the one thing
that needs to get done today,
I always start with one.
'cause if, if I don't
get one done, it doesn't
matter if I have two.
But here's the one thing
I have to get done.
And let's say I, I motor
through that went faster
than I expected it to and
I got two and three done.
Cool.
Now I know that I can just keep
adding more shit to the list.
That's just the nature.
The list never ends.
Right?
The only way I've been
able to kinda like quote
free myself from guilt is
by accomplishing things.
If I knew I accomplished
something, it kind of
took some of the mental,
like the guilt off me.
But if I think that I'm not
accomplishing something,
work could be getting
done and I'm not doing it,
I'm not in a great place.
Right?
I'm just not.
No.
And I don't love that.
I think that the, the way
it's worked for me is that
I, instead of feeling like
down in guilt, it fires me up
to like be super productive
when I get back to it.
Right?
Yeah, yeah, yeah.
And a lot of times, like when
I was driving to, to pick up
the kids yesterday, right?
It's a 15 minute drive over
to where I had to grab 'em.
So on the way over there
I was doing voice notes
on the ad copy that I was
gonna write when I got back.
'cause that's what I paused.
To go do that.
Right?
I had some ads I wanted to get
out and I said, all right, I'm
gonna go do this thing instead.
Spent that time,
get myself fired up.
Okay?
So then when I get back,
I've got, I've got the, the,
the core what I need, right?
And it's not like it's, we're
never really off, right?
It's so hard to complete
switch off car by myself.
I've got some time.
And so for me, what I've been
trying to do is just use that
as the motivation, right?
Mm-hmm.
That instead of letting that
feeling just kind of like sour
within me, trying to use as
a little bit of fuel to say,
okay, I'm gonna go do this.
I'm grateful that I can go
do this thing with my kids.
I'm gonna use that gratitude
and the fact that I am a
little anxious about not being
at my desk to do this right
now, to, to, to elevate the
work when I get back to it.
I think it's, I like
that seems to be working.
I also think that I, I, if we
look at kind of the, the, the
ROI, if you will, that our
startups provide for us, the
obvious one is profit, but the,
the, the reason, that's a tough
one to, um, to always align to.
Is because most of us
won't get to a profitable
startup anytime soon.
Yeah.
Yeah.
So what ends up happening is
we're like, once we get to
profit, once we make a lot of
money, then we'll be happy.
And, you know, that's a,
that's a bit of an elusive
goal, but let's, we'll save
that for another podcast.
But because the startup is
perpetually not as successful
as we want it to be.
We always feel like all
other costs or commitments
are justified until we
get to that threshold.
Yeah.
Okay.
What we lose when we're
using that kind of math that
like it just numeric dollar
sign math, profit equals
success equals happiness.
Is that we can use that.
As an escape to make ourselves
miserable along the way.
It's basic saying, Hey, we just
keep extending the finish line.
But the race is so grueling
and so awful that even if
we cross the finish line,
it won't have mattered.
We'll be dead by then.
Yeah.
It's dangerous when we
don't see the other types
of ROI We need to be
extracting from the startup.
For you, when, when you
think about those other
types of ROI, where would
you, and, and clearly like
we have to be performing
within the startups, right?
It doesn't, doesn't work
otherwise, but I think
the misnomer for me has
always been that like there
were these points, right?
You set it like there's
milestones we hit where all of
a sudden then it'll be okay.
I've been in positions
where I, I loved my revenue
numbers and I hated my life.
Right?
So it it isn't
necessarily correlated.
Yeah.
There's also been times where
like, I've loved my life.
Just made peace with the fact
that revenue wasn't where I
wanted, but hating my life
and, and designing a life that
I hated wasn't gonna help me
hit revenue numbers, right.
Growth on paper means nothing
if it's fueling misery, and
so we've gotta find some
kind of balance from that.
But for you, what would
be the right after the,
the, the startup metrics,
like what's the next one
that matters to you most?
I think part of it is working on
something that I care about.
Right.
Uh, uh, that's been probably
maybe the number one RO
i@startups.com for me, and,
and I'm guessing maybe for
you I'll, I don't wanna
put words in your mouth.
I love who I work for,
being the, the startups
and I love the value of,
of, of what we provide.
Now, to be fair, if I wanted
to optimize just for income,
I'd probably go work at
a public company, right.
And climb the ranks
and, and be manager guy.
I would be miserable.
Right.
I'm sure of it.
I would be miserable,
but I could make more
money doing that.
However, and this goes back to
the ROI, I wouldn't get any ROI.
I'd have more money in the
bank, but be less happy.
And if money is, is a conduit
partially to happiness, right?
Then I would actually be short
circuiting that because I'd
be getting the money, but
not any of the happiness.
And so when I look at startups
I've built in the past, not
that I didn't like them, but
they had no emotional ROI.
When I ran an ad agency,
like the work was kind of
interesting, but I didn't
jump outta bed in the morning
and being like, I can't
wait to help Best Buy, sell
more digital cameras, right?
I don't care.
Whereas with what we do, like
later on today, we're gonna
get on the phone, um, oh, I am.
I've got a bunch of office hours
calls with a bunch of founders,
and I'm gonna help them work
through tons of problems and.
I love that.
And to be fair, their
gratitude is phenomenal, right?
They're like, man, I
didn't even see that.
Or, you helped me through
a really tough time period.
Ryan, we get this.
A lot of people that that
listen to the show, right?
Yeah.
Yeah.
A hundred percent.
Yeah.
We hear that kind of
feedback all the time.
Uh, we get it from
our office hours.
Uh, I get the same thing
from the workshops they
do on Mondays and Fridays
around getting customers.
It just always feels
amazing, right?
And, and those kind of things.
Truly are, I think I said
this a couple weeks ago
in, in the team Slack.
I was saying that like, those
are the moments that pump me up.
Like I was heads
down and grinding.
I was, you know, trying to find
a smoking gun around a problem
I was having within HubSpot,
couldn't find it, and it was
driving me crazy and it could
have completely changed my week.
And instead I was like, I get
so fired up by those things
that we get to do, those
interactions that we have with
the, with the startup founders
that at that point, like it
just, it fills you up, right?
And if your startup is
constantly leaving you
feeling hollow, then.
Any returns that you're
generating as a result of that?
Kind of get couched as
losses in my book, man.
Because emotional
bankruptcy is a real thing.
Like it's a, it's a very
real thing and I'd say that
it is almost always hand in
hand with burnout for me.
Or maybe even the precursor.
Cause for the burnout,
like you and I both have
incredible motors, we
can just keep working.
Right.
That's not the problem.
Right, right.
When, when the work no
longer rewards intrinsically,
not extrinsically, then
I think it starts to
fall really flat for me.
I agree.
I also think, and this
is, this is minor.
I don't think you and I
have talked about this much,
but I think just the way
we've designed our business,
nothing to do with the,
the, the industry we're or
anything else like that.
Yeah.
I mean, the actual business
that we run, we are very
hands off with the team.
Right.
Uh, team has a phenomenal
level of autonomy and, and.
For me, that's a reflection
because I don't wanna be up
in people's business all day.
Right.
That brings me no
pleasure whatsoever.
In fact, the more I have to do
it, the more miserable I am.
But, but I think it's a flip
side from a culture standpoint.
The folks that work with
us enjoy a phenomenal
level of autonomy.
We also know they
don't always work.
Right?
There's some people that
look at it as autonomy as
time in the pool, right?
I'm kidding.
But like, yeah.
And there's some people who
look at autonomy and say.
I can't wait to do great
work and I'm gonna do
it on a schedule that
works great for me.
And we have plenty of those
people here that can do that.
But what I'm saying is from
kind of how we've designed this
company and how it's evolved,
I'm really proud of that.
You know, I'm really proud
of, of that level of autonomy.
I'm really proud that we have
a culture that supports that.
'cause Ryan, if we had a
different version, okay,
where in our culture it
was all about hierarchy.
It was about 360 degree reviews.
It was about basically,
uh, micromanagement,
et cetera, company.
I'm getting nauseous.
I wouldn't change the topic.
Yeah, yeah, yeah.
I wouldn't wanna
work at that company.
Right.
Leadership.
Great.
Management, not so much.
Right?
Yeah.
It's just, it's the worst.
It's the worst.
There's a time and
a place for it.
I totally respect it.
Yeah.
I'm not saying
management is awful.
I'm saying I just
don't enjoy it.
Right?
Yeah.
I just don't enjoy
it at that level.
I wanna work with people
who have autonomy.
I wanna work with people
that are self-motivated.
Again, that doesn't always work.
I would say more often
than not, it doesn't work.
As an example, this is, again,
this is, we're tensioning
a little bit, but like we
don't do personnel reviews.
We've never done them.
There's been no
360 degree review.
There's been nothing.
Right.
And my take on that,
and again, this is all
about building something
that like works for you.
My take on that is if I can't
manage the person day to day
with expectations and I have
to wait a year to tell them
they're not doing a good job,
what the hell am I doing?
Right?
Yeah.
And, and if, if the person I'm
working with has no idea how
well they're doing, I'm like,
I'm really bad at my job now.
I'm, uh, maybe it's
me just being lazy.
I found that the people who
work really well work just fine
in that, uh, that environment
and the people that don't.
Don't.
Yeah.
But my point is those
things don't make me happy.
And so I've generally
said, okay, let's build a
system that works for us.
We don't have to
do those things.
And I think that's powerful.
It is.
And, and look, I think
those are some of the
best decisions we've made.
And you know, they don't show
up directly on a p and l.
Clearly I think that they do
impact it, but they're not the
kind of things where it just
shows directly on, on a PL.
But they keep us energized.
They keep us happy, they
keep us creative and and
that matters a lot, right?
You can't deposit happiness
in a bank, I suppose, but
you can't buy your sanity
back with money either.
So we gotta be careful
of what we're trading
at any given point.
You know?
Here's a different
way I'd phrase it.
Money makes me safe.
Yeah.
But the work I do and how I
spend my time makes me happy.
Can, can.
Yeah.
Yeah.
I'm saying, right?
Like, I think that's,
that's the important part
in this case.
It it, it does.
And, and let me build on that.
I've spent way too much
time thinking about the
things that make me happy.
Uh, the activities that make me
happy, fun fact, they generally
don't cost anything, right?
The, the, the things
that I enjoy doing.
I enjoy playing hockey,
enjoy playing t spend
time with my family.
I enjoy, uh, building stuff.
I, whatever.
They generally don't cost much.
I'm building a house now that,
that does cost money, but
it, that's just incidental.
I could be working on
anything else as a project.
Yeah.
You know?
Like that wouldn't
necessarily have that
cost associated with it.
And so again, I look at
money, not as if I have
more, my happiness is gonna
go up, but if I have left,
my safety is gonna go down.
So I look at that as kinda
like my baseline in the
formative years of my life.
Before I was an adult, I was
poor and I wasn't unhappy,
but I was very unsafe.
And I can tell you from
that experience, it's very
hard to be consistently
happy while being unsafe.
Those two things there,
there are a correlation,
they're different.
Yeah.
They're correlated, they're
diametrically opposed, right?
Like, I'd say it's, I
wouldn't say it's difficult.
It's, it's gotta be
nearly impossible.
If you're not safe,
how can you be happy?
Conversely, though, if you
are safe, you know you're
financially well off.
It also doesn't
guarantee happiness.
It doesn't work the other way.
It does not.
It's, uh, it's something I
always say is money may not
buy you happiness, but you're
rarely happier without it.
I
think what it comes down
to is figuring out what
that, like, what that actual
threshold for safety is.
Yeah.
Like at some point if you just
keep chasing more and more and
more and more safety, like what
are you building safety against?
Right.
You be, it's like the
difference between, you
know, having batteries in
a flashlight, I. Building
a bunker in your backyard.
Right, right, right, right.
They're both derived some
level of safety, and then
you gotta decide how much
safety do I actually need?
I think that's where we, we
can get it wrong and maybe
we don't take our, our foot
off the, the safety gas pedal
soon enough and start to
apply some, some effort to
happiness because I. For years,
we're, we're measuring our
success by how much discomfort
we can tolerate, right?
Like, I'm willing to be
here and I'm gonna grind,
I'm gonna build, I'm gonna
do, uh, and then we wonder
why we're desperate to
exit a business, right?
Like, like you and I both
were, uh, around the, the
early agencies where it's like,
yeah, I don't wanna do this
anymore, please with my hands.
And so.
I think it comes down to
just picking that point and
saying like, this is safe
enough, and now I can start
to focus on bringing some
joy into this equation,
but stick with that.
I think it's important for,
at the very least, for us
to get like a milestone that
says, Hey, the business isn't
where I want it to be yet.
That's usually the case.
Okay, I get that, but that's
not a perennial excuse for
me to allow it to make me
miserable all the time.
Because if I agree that it's
okay for the business to make me
miserable, yeah, and this, this
has nothing to do with whether
you're willing to sacrifice.
There's always a
sacrifice to be had.
There's no deliberate
stopping point in sacrifice.
This goes back to the business
being all consuming and for
decades, not even years.
For decades.
I didn't appreciate
that threshold.
I thought wrongly that there
was something on the other
side that would automatically
tell me I don't have to
behave like this anymore.
And there wasn't.
I mean, you know, one of the
things I, when I talk to people
who are substantially successful
and they have bigger enterprises
now, is they're like, I have
way more mouths to feed now.
Right.
Like, my problems
are much bigger now.
Yeah.
Like my pressure's gone
way up and I'm like.
Damn.
Not only have you not
gotten over the threshold,
you made it higher.
Right.
That's scary.
I think it goes back to
something you said at the very
beginning, which is like the
the abusive relationship model
where then you just start to
build on that and you just
continue to build more of that
abuse into what you're doing.
Right.
At some point, like I. All
you're doing is creating
more obligation to grind.
Right.
Right.
And I think that one of
the things for me, and, and
this speaks to the fact,
like you said, we're, you
know, we built a team that
we love, we love being with,
and we don't have to manage.
We, we've built clients that
we love hanging out with.
Yeah.
And, and can drive
amazing results for.
But I, I see so many founders
building out of just.
Fear and obligation.
They're like, well, I've
managed to get it to this point.
Now I just have to keep
doing this because now
it's at least paying the
bills or whatever it is.
Whatever the thing
that like Right.
Maintenance will keep,
it will, will keep you
some level of safe.
Right.
I think if you ask most of
those, if, if you took the
obligation out of it, the
obligation to grind against this
thing, would you still do this?
Right.
And I feel like in a
lot of cases the answer
would've been no.
Like if I didn't feel
obliged to grind towards
the end of the agency.
I would've stopped because
I was not enjoying it.
I wasn't building anything
meaningful anymore, and
I just didn't really
care about the business.
And it sounds bad, but you've
said the same thing before.
I didn't really care
about the clients.
Well, not in the same way
that I care about some of
the folks that you and I know
within startups.com where
like, I legitimately care
what happens to these people.
Like I want to know.
And I want you to feel good
about it, but I think, you
know, if, if you're not, if
you can't say, if I take the
obligation outta this, would
I still grind in the same way?
You're probably building
something you're gonna
resent at some point.
I
agree.
And what's interesting
is how much of this is
from our own making?
This is, this is a little
bit out there, but, but
bear with me, I picture
this version of me.
Okay.
That's Edward Norton
in Fight Club Uhhuh.
And I've built this person that
I live with being my startup.
That's Tyler Durden, right?
Yeah.
Yeah.
That's constantly pushing me
to get my ass kicked you on
to do things.
Yep.
Yep.
Right.
And at the end of the
movie, I realize he's me.
Yeah.
Yeah, right.
Like it wasn't
actually a person.
I was the one who
created all that.
Yeah.
And I think that's part of
what this is, is we can wake
up tomorrow and we can have
the version of our startup
company where we've got a happy
relationship, a non-abusive,
or we can continue to create
this fight club, Tyler Durden,
Brad Pitt, you know, archetype
that will constantly kick
our ass and have us feel like
we're a victim of this thing.
The difference in the two.
Is us, right?
That's the difference of
the two, is our ability to
wake up tomorrow and say,
to hell with this, right?
I, I'm not gonna live like this.
I'm not gonna create this
thing that was supposed to
be beautiful, but be becomes
abusive and let that beat me.
The only way I'm ever, ever,
ever going to be able to get
out of this trap is to wake up
tomorrow and do it differently.
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.