Subscribe
Share
Share
Embed
The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to the episode of
the Startup Therapy Podcast.
This is Ryan Rutan,
joined as always by my
friend, the founder,
and CEO of startups.com.
Will Schroeder will, one of
the hardest parts of being a
founder is building the company
while realizing that you're not.
Fully in sync, lockstep
synchronicity with
the people around you.
And you know, we hear
people say things like,
you know, build alignment.
They forget to tell you in
their brochure is that alignment
is, is largely fictional.
And like we love, of course we
love to imagine that we're all
on the same team, but like ever
watch the ship take on water,
it becomes really apparent.
Who has a life fest and
who doesn't goes down
with the ship super fast.
And so after decades of
trying to force alignment, I
think I've realized it's less
about sinking goals and more
about managing fundamentally
misaligned expectations.
Yeah.
And foundations, right.
The big, the big question
is, you know, are, are we
really aligned with everyone
around us, our employees,
co-founders, even our spouses?
Right.
Are we
right?
You know, you and I did a
whole episode on this as
it related to investors.
Yes.
'cause investors love to
say, you know, we're gonna
be on the same side of the
table and we're aligned.
And I'm like, no, you're not.
Not a good remote line.
They're cheating because
they mean that, but
it's a round table will.
So it's not, it's not fair.
It's a round table.
So just by definition, we're
all on the same side of Same.
Yeah.
Right.
Right.
That's right.
Right.
And I just think about like,
I thought that argument
was so hollow uhhuh, and
it sounds cool, but it's
just so incredibly untrue.
Yeah.
But with this episode, I
think we need to go beyond the
investors because this same.
Fake alignment problem
where we wanna be aligned,
but we're just not.
Just not is, as you said,
as much of a problem
with co-founders, with
employees, with spouses.
And I think we should
talk about spouses too.
Yep.
Because they're like the
unsung hero or villain.
Yes.
Depending on how your
relationship goes.
They're an ever present
high leverage personality
in all of this.
Right.
Yeah.
You know Ryan, I've never
thought about it like that.
A high leverage personality.
That's absolutely true.
That's really well put.
It'll be the last time I say
something that's smart today.
So yeah, we're all done.
Take on.
Thank you.
Thank everybody for being
part of the service podcast.
That's a wrap and I'm done.
So lemme say this, I
struggled with this
concept of alignment for.
Decades because Yeah.
I wanted to believe, and I
think a lot of other people
do too, I, I wanted to believe
optimistically that I could
have this like symbiotic
perfect alignment with all the
people in my life and Sure.
And if that, and if that
alignment didn't exist,
it was just some sort
of like Lego piece I was
missing to complete the.
Right.
It never occurred to me it
does now that the alignment
was so far off to begin with,
that crossing that, that,
that chasm, it was way harder
than I thought it would be.
And, and again, I think today as
we unpack why those chasms are
so significant, even in stuff
like co-founders we're supposed
to be in the same place.
I think it's a big deal.
Yeah.
Yeah.
Yeah.
It is.
And, and I think it's another
one of these things I, I, I seem
to keep echoing this, but it's
one of those things that starts
at that really early stage.
Then we carry it forward in
a lot of cases unnecessarily.
I realized at some point
that one of the reasons I was
looking for that alignment,
the reason I wanted it so
desperately to be aligned was
that at the early stage of a
startup, very little is working.
Right?
Right.
And so it was almost as if,
as long as everybody else
was aligned with me, like as
long as everybody else sort
of like felt like what I was
doing was the right thing.
Like it was some form of
another, like a validation
or maybe it was just
even as simple as like.
If everybody else could have
the rose colored glasses
on, I could keep swimming
through the Meyer, right?
Just like somehow I needed
that alignment psychologically
less actually, like from a,
from a practical standpoint,
I didn't actually need
them to do anything, right?
Like, I don't need my spouse
to be aligned with me so that
I can go do the thing I have
to do, or that she can do the
things that she needs to do.
I just wanted it to be, I
wanted it to be so that I
could feel good about going
and doing what I had to do.
It wasn't fundamentally
gonna stop me from doing it.
Yet it can, it
also feels a lot different
when it's, when it's
not aligned, right?
There's one thing why I don't
need all of your support, but
getting negative support where
you're actually tearing me
down is definitely a problem.
You know, Ryan, I'm,
I'm gonna rewind back
circa 20 12, 20 13, some,
somewhere in that era, okay?
Mm-hmm.
Yeah.
Um, deep in the archives.
Deep in the archives, and you
and I are just starting to
hire this new entrant to the
workforce called millennials.
Okay.
Yeah.
Yeah.
Now, now, and again, I hate
when people do this like, like
generational class warfare,
et cetera, but, and I know
a lot of our audience are,
you know, are millennials.
So, so bear with me
when I say this, right?
Ryan and I are, are, are
in the, the Gen X category.
None of this matters.
I'm just pointing out,
this was our first time,
like in our thirties.
Yeah.
Hiring a generation
that wasn't us.
Right.
They were just entering.
Right.
There was finally, they were,
they were now of legal age
to hire, and so Exactly.
We started doing so.
Right.
Yeah.
And so this was the first
time in my generation, right.
And I remember having these
conversations with you.
Where a new generation comes
to work and they brought this
new concept that we had never
heard of before called work-life
balance and, and, and what
work-life balance means is
I don't wanna work as much.
I've never heard someone
introduce work-life balance.
That also includes,
because I wanna work more.
Right.
Can you lighten my life a
little so I can put more weight
on the work side, please?
Exactly right.
So anyway, that's
here nor there.
Point is we start hiring
a, a bunch of millennials.
And by millennials I just mean
like 22 year olds at the time.
Okay.
Yep.
At the time, that
was it at the time.
Uh, they're in forties now,
but at the time they'd come
to work, they were fine.
Right?
All, all good, all green
light signals, but the
craziest thing happened.
At six o'clock, which we,
sorry, we worked at, uh,
nine to six at six o'clock.
Everyone would pack their
laptops in just all at once.
Just like, yeah, lemons.
And you could separate without
having to say a word, who is
Gen X and who is millennial.
Right?
Because the millennials, like
you were still sitting, you
were Gen X
if you
were
Exactly.
No one said a word, right?
Like no one had to say a thing.
No, but the, the reason I bring
this up is it was the first time
that I had ever seen such a.
Dramatic distinction between
my vision of alignment and
their vision of alignment.
Okay.
Yeah.
And so I leaned in naturally
and I asked some folks,
I was like, so, you know,
you're leaving at six.
It was like a half day.
I mean, I'm, I'm kidding.
But like, you know, that's,
that's kinda like, uh, and
they were like, yeah, that's
'cause I'm an employee.
You know, I, I'm not the owner.
They said this in so many
words, but it was the first
time they'd ever heard
someone verbalize that.
Now I was like, huh.
You're not wrong.
Yeah.
You, you've got a point.
I don't like that it's
pointed at me, but you've
got a point, right?
Like, I, I don't get to
leave the movie halfway.
I, I have to stick until
the, the credits roll, right?
Like, why do you get to leave?
It didn't occur to me
that our incentives
were different.
Like up until that
point, I had never had to
have that conversation.
And what I'm saying is
just, and there's nothing
wrong with what they did.
My point is that they
did it right and it, it
forced me to realize that
we're not in alignment.
Prior to that, I'm
not even kidding.
For like, like 15 years, I
would work until midnight
with my entire team.
And now mind you, we're all
younger, but so were they right?
Like, and no one would
think twice about it.
There's a guy at a Santa
Monica named Jason Nazar.
Yeah.
Um, Jason started doc stock.com
and then, damn, I just blanked
into the second company started.
I think he sold 'em both.
And uh, I remember one
time I was in Santa Monica,
that's when I was living
there and uh, Jason's like,
Hey, let's grab some dinner.
We got to dinner, it's like
nine o'clock, a little bit
late for a dinner, and after
dinner he's like, uh, uh, I
gotta head back to the office.
I'm like, oh, did
you leave something?
He's like, no,
we're still working.
Story just, just because I
had to see this and we were
walking past his office
Anyway, I go, I wanna go
see what this looks like.
Right?
I go in, Ryan, his entire team
was there, like, no different
than when I'd stopped by at
like three in the afternoon.
Right?
Right.
And I'm not saying
this is healthier.
Good.
No, no, no.
I'm saying somehow he had
aligned his interests and,
and like his interest of
being a founder with their
interests of, of wanting or
maybe having to be there.
Yeah.
But now I can't
even fathom that.
Like, I don't even pretend like
those interests are aligned.
No, I, and I think that was
part of the challenge, right?
Is that early on, right, I used
to expect my staff to have to
be as, all in as me and, and
anyone around me, and it was
participating anything with me.
I always expected everybody
else to be as in as me.
I told the story once about
getting dressed down by my
coach after, after trying to
push the team too hard and,
and basically having me explain
exactly this to me is like.
The consequences aren't
the same for everybody.
Not everybody wants the same
things out of this that you do.
Not everyone's gonna
get the same things out
of this that you do.
Therefore you can't expect
'em to put the same things
into this as you do, right?
So me expecting everyone to be
as all in as I was, wasn't fair,
wasn't fair for the, the, the
team wasn't fair for my staff.
Later.
They didn't sign up for what?
I'm just gonna say my
level of consequence.
Correct.
Right, right.
In either direction.
Right.
If it goes really well,
it will go better for me.
If it goes really
poorly, it will go a
lot more poorly for me.
Right.
The the way.
Yeah.
It'll, we are, it's, it's
funny, you can kind of think
of, it's like a pendulum.
We are way out at the very
far reaches the pendulum.
So when it swings,
we swing all the way.
There's somewhere
down near the bottom.
So yeah, it goes back and forth,
but it's like being on deck
versus being in the crow's nest.
We're in the crow's nest, right.
So when the ship tilts,
we go all the way.
And I think that.
Once you realize that and you
stop expecting that alignment,
it, it got a little easier.
I'm, I'm not gonna say
it got easy, it was still
hugely frustrating for
me, but it got easier.
Yeah.
Okay, so, so stick
with that then.
So I think my challenge, and I
think a lot of others is, Hey,
we're all in this together.
We're all gonna build
something great.
And it's like, yeah, sort of.
Actually, I'll give you
another interesting point
about this concept of.
Ownership, if you will.
And I don't, I'm not talking
about equity, I just mean
like ownership of the,
of what you're building.
Okay.
Like, just like genuine
passion for what it is.
This concept of not my baby.
And, and by the way, not my
baby does not mean that I wasn't
the person that started it.
But what I'm saying is there
are folks and like you and
g and you know, folks like
that, that have full ownership
of what's here, right?
Yeah.
Like even there from the start,
you, you've built this thing,
this thing is a part of your
DNA, but it stops there too.
The, the other people
that are in after, after,
after, don't have that.
Like, don't have it like
it's my baby two kind of DNA.
Yep.
And for a long time I just
assumed if you were on
payroll, you had that DNA.
Right.
No, it's, it's not it.
And you know, it's
interesting because I think
that, you know, some of
it is that that ownership.
There's a particular type of
ownership that I'm gonna, I'm
gonna call out here because
I, I think that commitment gap
isn't necessarily about loyalty.
Right.
Right.
Yeah, I agree with that.
Totally.
It's, it's, it's the, the
ownership is, is about the risk.
It's about who owns the
risk in a lot of cases.
Yep.
Right.
Who actually owns the
downside of this thing,
because that is going to
really and truly determine.
How committed someone is.
Now, I, I think you're talking
about a different type of
ownership, which is also
extremely valid, which is
just having been and built
and, and, and been part of it.
And literally it's part
of your DNA, you're
part of its DNA, right?
Like you pull this out and
like that's a, that's now it's
no longer the same company.
That's a different aspect,
but equally as important.
Well, my frustrations have
been, have been going in
these conversations with an
expectation that they, they saw
things the way I did, and again,
the consequence was a big one.
Yeah.
I'll give you an example, like.
10 years ago, I remember you,
me and a couple other, other
leadership were on a, a chat.
This was on a Saturday.
Okay.
And something was going
wrong with something maybe
like our, our ads weren't
firing or something, like
there was some like issue.
I remember like, like
chatting with, with all of you
particularly, you know, one
of the folks in in the group
was like, Hey guys, honestly,
this is like a weekend.
You know, I wanna be
off on the weekends.
I don't wanna, um, do that
in my response in so many
words, but not these words.
I'm just trying to
like paraphrase was, if
that's your response, you
shouldn't be on this chat.
Meaning like you shouldn't
be in leadership.
The point of leadership is that
you do have to take these calls.
You are tied to these
consequences.
Yeah.
Right, right.
You don't, you don't
get to call off.
We lose level of shit.
Like it wasn't, it wasn't
like we were like, Hey
guys, what do you think?
Should we plan the Christmas
party for the 15th or the 18th?
It's like, Hey, there's a
fundamental challenge like
we're taking on water.
Yeah, exactly.
You up, we're picking on water.
Yeah.
And so, but again, it's
back to that reframing.
So now what I've come to,
to realize, and again,
this will start to,
you'll start to see this.
Theme permeate through
everything we're
about to talk about.
What I've started to realize is
I have to be super honest about
what those differences are.
If we can't make payroll,
they will lose their job.
And there is nothing, there's
nothing inconsequential about
that, that's meaningful, right.
That's, those are
people's lives.
But if I can't, uh, make
payroll, I lose everything.
I, everything, I lose
everybody's jobs, right?
Yeah.
I lose my own job.
I put myself into personal
risk, like, you know, I
can't just quit and restart.
To your point.
Everyone else has some
version of a life raft.
I'm going down with this thing
to the bottom of the ocean.
Yep.
So yes, I'm freaking out
about it on a Saturday.
There's a reason someone else
isn't and I need to check myself
before I have that reaction
for sure.
And I, I think like as, as time
goes on, one of the things that
I've realized, particularly
within the, the employee sec,
I don't need everyone to.
Agree.
I don't need everyone to
have the same level of
commitment or consequence.
It's about them showing up.
Right.
It's not about
everyone agreeing.
Yeah.
It's about everybody
still showing up.
Right.
It's about being there, doing
the thing that I need, and
me being very clear on kind
of what I need and letting
them be very clear on,
on what I need from them.
Sure.
But, but it is still frustrating
and you know, it's funny, I
do believe that part of this
comes from a really good
place, which is do you just.
We're seeking out that, so
like the, this desire for
alignment, particularly amongst
the team, forget the, the
spouses for a minute, forget
the, the, the people who aren't
directly, directly, like in
this, like literally turning
the screws in the bolts and
building a machine with us.
I think part of that is
this sort of like desire
for camaraderie, this
desire to feel like.
Everyone cares enough to,
to really wanna do this
for all the right reasons.
So again, I think, I
think part of this does
come from a good place.
This isn't me saying like, I
need everyone aligned so that
we can get things done and grow
faster and make more money.
It, yes, that is one of the
byproducts, but I think for me
it was just always about like,
it always felt good, right?
Right.
It was like you ever pull
like a study all night?
Where it was like, let's,
let's ace this exam.
Okay, well that was the
thing that used to happen.
Or just, you know, let's, let's
stay up until this thing ships.
But like at that level where
it wasn't out of some sense
of obligation, it was a sense
of desire and pride that
happened at an individual level.
They culminated in a group
of people doing something
pretty awesome together.
And I think that like part
of me will always want
to recreate that, right?
Right.
Part of me will always wanna
say like, let's do stay at the
office till midnight, and then
I'll look at labor laws and
go, yeah, let's, maybe not.
Yeah.
Um, but okay,
so let's take that
off the table though.
Let's move up the
chain to a co-founder.
Okay.
And here's someone, let's
say you have 50 50 stock.
Like, you know, we're, we're
taking off the, Hey, you have
more than I do, kind of thing.
And so at that point you're
like, well, well then
we're definitely aligned.
Yeah.
Uh, because we have the
same amount of stock upside,
downside is the same.
Let's assume every dollar
in dollar out is the same.
And I'm like,
yeah, no you don't.
On paper, those should
align, but that's actually
not what creates co-founder
disputes more often.
It's an expectation.
It's
being in the same boat and
looking at different maps.
Yep.
Right.
It's, it's, look at it
that's like, it's, it's
super frustrating, right?
Yeah, yeah.
And for both sides, clearly.
Right.
Except when just wouldn't
you, like you and I we're
always the, the ones
that are right about it.
And so then like, it's, it's
more frustrating for us because
it was their misalignment.
I was like, okay, so
here's what I would say.
The thing that I've seen.
The most is an expectation
of contribution.
Ryan, you and I, you and
I are 50 50 co-founders on
something, and we both have
an expectation about how
contribution's going to work.
And here's a couple places that
backfires and, and using you and
I as a metaphor for like every
co-founder, the first place
that backfires is number one.
Everyone thinks they
work harder than they do.
We, we did a whole
episode about this.
You know, talking about
like people's perception
of how hard they work.
So like I come home to
my spouse, I'm like, oh
my God, what a long day.
And my spouse just assumes
that must mean that I've
done all this effort.
Right?
Right.
But I could have worked
for two freaking hours,
but I could, I could have
professionally complained
about it when I could home.
Right?
Or in my mind, I quote,
work really hard.
I mean, Ryan, you and I
have both dealt with this.
In fact, I think we've
done podcasts about this.
I've had days where I've
felt like I've just gone
through a slog all day and
have nothing to show for it.
Nothing to show for it.
Yeah.
Some
people, that's
their career, right?
They're
busy, being busy, and in
their mind, yeah, like,
I worked hard, but you
didn't get anything done.
Like, yes, you spent
time in a place
that doesn't mean
you had output.
It's gotta come down to,
to transformation, right?
Something has to have
changed based on what
you did and hopefully
positive transformation,
not just something changed.
Ryan, you ever play a
soccer game where you worked
really hard but you didn't
score any points?
Yeah, most of them.
And I'm not the goalie, right?
Yeah, yeah, I was gonna say.
But, but you know, same thing.
And so my point is, that's
usually where it starts,
this, this misalignment,
is that our expectations
about our output and someone
else's output don't align.
So it's like, I'm doing
everything right and they're
fucking everything up.
Okay.
So, so that's one part, but
another part, I'm just gonna
give you the two categories
and let's kind of, you know,
build into a little bit.
But the other part is, uh,
an expectation on how this
company should be run.
That has so many tentacles.
That's everything does from how
our culture should be to whether
we take on money to whether do
we pull out cash now or do we
reinvest it for the future or to
what our product's going to be.
You know, you name it.
Right?
And those expectations
can become so dissimilar.
Our alignment is
damn near impossible.
Even though on paper we
should be on the same side
of the table.
I think that's the, the bigger
one for me, because I really
do feel like when, when the
friction isn't about effort,
meaning like what are, what are
our actual daily contributions?
Because to your point,
everybody's gonna have a
different view on that anyways.
Right?
Like the way I feel about
what I did today may
or may not be accurate.
So the way you feel about
what I do today, probably
even less accurate, right?
Third party.
So it's like.
It's super tough, but when, when
the friction isn't about effort,
when it becomes about direction.
The fundamentals of how are
we running the business?
Who are we running it with?
Who are our clients gonna be?
Who are our staff gonna be?
All of these little things
that, that are so, so
involved in whether the
company works or not, or how
well it works, or how well
we enjoy how it's working.
That was what I meant before
when I said same boat,
different maps, right?
Even if we're putting in the
same amount of effort, let's
say we do get that to parody,
like just every day, somehow
magically we hit exactly
the same level of of effort.
We're both rowing
exactly the same speed.
It turns out we're rowing
different directions,
we're going nowhere.
To me, that's the most critical
misalignment between, between
co-founders and I think it's
the harder one to diagnose.
Because what people will tend
to look at is the other person's
output and they'll go, whether
it's either working or not.
What they don't look at
in most cases is, is that
working towards the thing I
am working towards as well?
Like, are we even pointed
in the same direction?
If I can quantify their effort,
and that's all I looked at like.
Good Will went 60 miles an hour.
I went 60 miles an hour.
Right?
Too damn bad.
We went opposite directions.
Right?
That's not good, but
that's good point.
I think that's the part
people fail to look at, right?
That's the part people
fail to analyze.
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.
Okay?
So when we think about that.
And we're like, Hey, shit, I, I
really don't have the same type
of alignment as my co-founder.
Again, I think this is,
this is the, the recurring
theme I was talking about.
The first thing is to
recognize that, right?
To be able to say, I wanna be
on the same page of, of course I
want a page, but I'm not, right?
Like, I don't believe they
work hard, or I don't believe
that we should raise VC, or,
I don't believe this product
is, you know, ever gonna work.
Like, you have to be really
honest about the fact that
you are not on board with
alignment before you try
to force this alignment.
I see this, you know, and we
will get to, to, to couples
in relationships in a second,
but like, I see this in
relationships all the time
where you've got, uh, uh, two
people like somebody and their
spouse and they can't reconcile
because at the end of the
day, they just don't agree.
And they're like, you know, we
wanna have a happy relationship,
marriage, whatever it is.
And I'm like, you're
not going to, you
fundamentally don't agree.
Like your, your
foundation is broken.
And that's what we're talking
about here with co-founders,
which, you know, the, the
mirror between co-founders and
spouses is so freaking tight.
'cause it, you know, it
is that kind of symbiotic
relationship and I think
it's hard to get right.
The person
you spend the other part of
your waking hours with, right?
Yeah, exactly.
Yeah.
It's your daytime spouse.
You know, I think one of the
challenges, I'm gonna go back
to what I said, you know,
the top of the episode, which
is so many of these things
come from the early days
and just get perpetuated.
Now this one's a bit
different because it's,
it's an inverse curve.
I think at the beginning,
co-founder alignment
is actually very good.
Because there's damn near
nothing to to misalign on.
Right.
You're like, do you think
this is a crazy idea that has
almost no chances of succeeding
and we should just try it?
Yeah.
Right.
That's all there
was to think about.
Right?
There's nothing there.
Yep.
There's no consequence yet,
and I think that that's one of
the, the big challenges with
this is that founders miss the
opportunities or don't take
the opportunities to reassess
that on an ongoing basis.
Yeah.
I mean, talk about something
that needs real time monitoring.
It is co-founder alignment
because it's something that by
just nature of how a startup
builds, it erodes or grows
further apart as time passes by
virtue of growing the business.
Yep.
Some, in some ways, your success
is what will drive you apart.
I don't mean that that like
success necessarily has
to, but just by getting
bigger and having more
dynamicism in the startup.
You are inherently driving more
variability, more opportunities
for us to be misaligned and
go different directions.
Do you ever see this
get caught in time?
I'm trying to think of
like, have I seen like
founders catch this in time?
I feel like there's like
two types of founders.
The ones that are like, they
were just measuring it and
they're constantly talking
to doing it, and there's
the ones that get to like
the cataclysm and they're
like, holy shit, I don't
even recognize you anymore.
Let's try to figure this out.
I think everybody
waits till it's too late
because no one, this is, this
is the whole point of this.
This episode is, no one
anticipates why it would be a
problem to begin with again.
Right?
We go in this with the, oh, you
know, we're 50 50 partners, so
I guess everything is settled.
That that's the least
of your concerns.
Best case that's, you
know, that's settled.
Uh, worst case is
even that's a problem.
But, you know, as we're talking
about this, as we're talking
to relationships, let's take
this over to spouses because
I, I think we're gonna see
a lot of parallels here.
Yeah.
But what I would say, and
we said this at the top
of the episode, spouses
are like the co-founders.
No one talks about.
For every founder there is
someone at home and, and
we say spouse, it could
mean, you know, whatever
your version at home is.
Your, your emotional
support that isn't your
direct coworker type thing.
Right?
But let's just use
spouses here for a second.
One of the things that,
that we don't consider when
we go into this is whether
or not our spouses are
really on board with this.
And I'll give you a a
very common example.
A common example is a,
I'll use my own wife.
Sarah just cares about
two things, safety and
security, which are
kind of the same thing.
Right.
She does not wanna
rock the boat.
Her answer to everything is
what's the safest answer?
And, and that's already
my answer before you've
even given me my options.
Now, the irony here
that she married a guy.
Who has done nothing
but roll the dice his
entire life, opposite's
attract because it to be true.
Right.
It, it, it, it's unbelievable.
And when she, you know, when
we met each other, when we
got married, I was already
like 10 years in my career
as an entrepreneur and I
was all in entrepreneurs.
Clearly I was never gonna
have a day job, so to speak.
So.
She knew what she was
signing up for, but it
hasn't changed her approach.
She's not like, well, you
know, we've married 14 years.
Like, it's not like
Sarah now is like, oh
well, you know, screw it.
Let's roll the dice.
You know, her answer is
no different now than
it was 14 years ago.
David got married.
When you look at this with Nagas
as she considers how dynamic
what you do is and always had
been, how does she relate to it?
Are you guys aligned on startup
work?
No, we're aligned in it.
This is what we're doing.
Are we aligned in
terms of, of how we, we
tolerate the pain of it?
Absolutely not.
Yeah.
Right.
Like it's, it's easy when
it's working well, right?
It always is.
I was just gonna
say the same thing.
Right.
I, I think that's, I
think that's an important
thing to think about.
And this, this goes
for co-founders.
This goes for, for spouses,
your, your person, whoever that
is, whatever that might be.
With co-founders, we're,
we're dividing equity.
The spouses were, were
not necessarily, I mean,
in under certain legal
circumstances sure.
You're also dividing your
equity with them, but
you are dividing pain.
Right.
The tolerance of pain when
things aren't going well.
Right.
So when it's going
great, get easy.
Yeah, who cares?
It's not problem.
It's easy to share the good
times when we're in the other
95% of running a startup.
It's not just about dividing
the pain, it's about the
fact that even if we were to
divide the pain equally, pain
tolerance isn't equal, right?
Rarely are we, are we
able to tolerate the
pain in the same ways?
And I think that that's one of
the, the things that we see.
I think that even the degree
that my wife and I are aligned.
Nagas is tolerance for pain
around a specific kind of way.
Anything that's a
threat to stability.
So very much like Sarah.
Anything that's a threat
to stability, uh, safety
and security for our family
is going to have very
little tolerance, right?
That gets a Yelp really quick.
And this is from a woman who
did three natural childbirth.
So she doesn't, she
doesn't yelp easy.
Right.
So like she can
tolerate some pain.
Yeah.
But there are particular
types of pain that she's
extremely susceptible to.
And that's, and
that's one of 'em.
And I think that was one of
the things that I, I started
to realize is like, to me,
the startup is so closely
tied to my identity and,
and to her, it's not right.
It, it's just an existential.
Threat to stability
in a lot of ways.
Now.
It also, it also does
provide, it also does
a lot of other things.
It it does, it does some
wonderful things too.
But I think that there is always
this sense that it is very much
a sword that, that that cuts
both ways and that there's a
very, very strong fear around
it, cutting that direction.
One of the things that's been
really successful for me with
my wife has been repeating out
loud what our differences are.
Yeah.
And, and lemme spin and
not to be confrontational,
to be reassuring.
So when we're doing something
and I'm always, you know,
you, you've been in this
for me for a long time.
I'm always doing something
frigging weird when
I tell her about it.
Not inaccurate.
Yeah.
When I tell her about it, she is
like, huh, well that's an idea.
Yes.
That's, that's, you
had a thought it's
something you could do.
Right.
Please don't tell me
you've already done it.
And so,
yes,
but, but did you say
theoretically, please?
Yeah, exactly.
Exactly.
So here's what I
always open up with.
I always say, look, while
we have shared goals.
Uh, in life, you
know, as a family.
Sure.
I understand that some of
these goals are just my goals.
You mentioned it a second ago.
You talked about kinda
like your ownership and
the, and the outcome.
Yep.
Your identity.
Those are things that are
important to you and I,
but they don't necessarily
matter to our wives, right?
Yeah.
Like, here's an example, Ryan.
If you and I service a
million founders or 10 million
founders, we're gonna have
some sort of reaction to it.
Yes.
Like there's some, it's gonna
spark something inside us.
Everything from pride
to reassurance to, uh,
you, you name it, right?
Like all these,
these good emotions.
My wife doesn't give a shit,
nor should she, by the way.
Right.
She wouldn't even
know it's, it's the
same.
Oh, wow.
Whether it's 10, a
hundred, a billion.
Right.
It's no
context for it.
And again, nor should
she, but this is my point.
Right.
Why would she.
Whenever we go down one of these
paths, when we're having these
discussions, I always like kind
of zoom out and I say, look, I
understand that, that my goals
and my aspirations are different
than yours now hopefully the
result of my aspirations help
with your aspirations, right?
Yeah.
But,
but, but, but
they're not the same.
So it's not fair for me to
say, for me to say, well, why
don't you just back me up?
'cause our goals
aren't the same.
Like, I'm trying to do
dumb shit in hopes that it
will make money, you know,
which will help our family.
But there's a lot of ways
to make money that are a
lot more safe than, than
what I'm gonna go do.
And I'm choosing not to do them.
So by default we're,
we're not aligned.
And when she hears that,
it doesn't mean she
instantly agrees with me.
But I think it goes for miles
to hear that someone understands
why you're not aligned
as we're saying this now.
I'm wondering if the if, I
mean, clearly we've sort of
said that like hoping for
alignment might be part of
the problem in the beginning.
Because when we start to talk
about misalignment, and I'm not
even sure that's fair, right?
Because we aren't
necessarily misaligned.
Misaligned suggests that
we were supposed to be
Oh, it's on the exact
same axis.
Yeah.
Right.
And it somehow we veered off.
The word that's springing to
mind now for me is asymmetry.
Asymmetry, acknowledges that
we're operating on different
planes entirely, right?
Like we're you and I are
operating versus where our
spouses are operating, right?
Where there are some common
goals, we are doing things
on entirely different planes,
different vectors, right?
Again, maybe a shared outcome.
Keep family alive the way
you and I are doing that, and
the way they're doing that.
Completely different things.
Absolutely.
It's different stakes,
different consequences.
Different time
horizons too, right?
Because there are decisions
you and I are making that have
like these in our own minds,
these far reaching consequences.
Like, I'm gonna start doing this
thing now that maybe will pay
off long time down the road.
Right?
And they're like,
how do we manage, you
know, children today?
How do we manage the
safety of the family today?
Oh, they're also thinking
long term as well.
I also think the other problem
with with misalignment, just
as a concept, now that I'm
thinking through it, is that.
Somehow it implies it
can be fixed with better
communication or realignment.
Whereas asymmetry says,
this is structural.
This is literally how
this thing was built, and
it's gonna stay this way.
All we can do is sort
of acknowledge, right?
I think to your point,
acknowledge, let's just
acknowledge, let's just
acknowledge the fact that we
are dealing with an asymmetric
situation or a misalignment.
I think that's about as close
as we can get, isn't it?
Right now, at, at this stage
in our life, me being in,
in my now early fifties and,
and, and you around the corner
to them coming right up.
We are at a stage in life
where all of our peer groups
are roughly at the same age.
And I, and I know this applies
to folks listening, so I'm gonna
be sensitive when I say this.
This is that era where
everybody starts to second
guess their marriages.
Just, just fundamentally,
the kids are a certain
age, the marriages of a
certain age where everyone's
like, shit, is this it?
And I have conversations
with all my friends around
this and, and Right.
I've got a massive friend group.
A massive friend group.
I know you have a
huge friend group too.
And I gotta tell you, all the
couples that Sarah and I know,
and we're talking hundreds
and hundreds and hundreds and
hundreds of couples, we can't
name three that are happy,
that are, that are aligned.
That's a pity.
That's fucked up.
Okay.
Yeah.
However, however, it
also goes to point to
how hard this is, right?
I think in the early days
we go into this being like,
well, I wanna be rich.
You wanna be rich,
you know, blah, blah.
Like, we're lying, right?
As if
that's, that's the
end of it, right?
Again, man, but look,
think about it though.
Like just from a, just go to a
pure mathematical state, right?
At the origin point,
everything's aligned.
It's the second you start to
move further, that that's when
the line, it can't diverge
until that when we're at
zero, everyone's aligned.
Right?
It's easy.
It's, it's, of course we are.
When I was a little kid, I, I
would, uh, walk up to another
little kid, doesn't matter
where we were, and I'm like,
I like Mike Tyson's punch out.
He is like, I like my
Tyson as a punch out.
Let's be best
friends.
Let's be best friends.
That
was, it.
Did, was there another
way to meet children
between 1986 and 1990?
No, and, and, and just
like I didn't use one.
I watch it with my son now.
It's the exact same thing.
Right?
He is.
He is like, I like Fortnite.
Is the other kid's
like, I like Fortnite.
We're best friends, right?
Yep.
So the point is, to your
point, we get this origin.
We're both on the same page,
but we haven't introduced any
of the other, the factors.
But I think what happens is
because we fail to realize those
really important nuances, we
don't acknowledge 'em, which I
think is important for all these
categories we're talking about.
I think acknowledging it is
by far the biggest part, and I
would say one part of that is
acknowledging it to yourself.
And being, being okay.
Like, 'cause a lot of people
will be like, oh well that
person doesn't work as
hard as I do, so fuck them.
Like, no dude like that.
That's the broken, probably
not premise that like, that's
why you're never gonna work.
Make this work.
Right.
The second part about
it is communicating that
acknowledgement to them,
Hey, I understand why you
don't work on Saturday.
Honestly, I have to do it.
'cause my consequences
are higher.
You don't.
Yep.
But if you would, you'd
be doing me a huge favor.
Yeah.
That is way different than, why
aren't you working on Saturday?
You create the acknowledgement.
Same thing with my wife.
Hey, I think we should go risk
our personal money as a family
on investing in this initiative,
but I know that there's a lot of
places we could put that money.
This is probably a riskier
one that I feel good about.
That makes no sense to you.
So I'll understand.
If you're hesitant.
It's not an affront to me.
It's because your risk
tolerance, your needs,
your outcomes are
different than mine.
Right.
So there's no version where
I can come to you and say,
what's wrong with you?
I, I should already
know that going in.
Yeah.
If I've got like, you know,
any, any level of empathy.
Yeah.
You know, it's, it's interesting
'cause I think sometimes.
There truly are times where
we're just looking at the same
problem differently, but I feel
like with this mal-alignment
or this asymmetry, that it's
not just that we're looking at
the same problem differently,
we're we're actually looking
at different problems, right?
We have the same circumstances,
but we're actually looking at
different problems, meaning
that the, the outcome that
they're most concerned about on
the other side of this thing.
Is different than, than
what we're looking at.
Right, right.
So the problem being a conduit
to whatever that transformation
of the future looks like, that's
where the, the difference is.
And I think that's, for me, it
was a hard recognition to have.
Like I had to all, all
of a sudden understand
and acknowledge that.
It's like there are times where
when co-founders, employees,
staff, friends, wife, children.
It wasn't that we were looking
at the problem differently,
it was that we were literally
looking at different problems.
Like we were just
fundamentally wanting to
go and do different things
from this new origin point.
Yeah.
I that where the problem is
now all of a sudden we're,
we're diverging there.
That's something you just
kind of have to respect.
There's not much
way around that.
Right.
Well, sort of trying to
just literally realign
people to make them you,
which, well, okay.
That's what I'm saying.
Right.
Like I, I went through probably
the first decade of my, of
my career frustrated Yeah.
That everyone wasn't.
On my plan.
And, and so I kept trying to
like force feed all of these
people into, into my version
of how I thought things should
go, and then being continually
frustrated every single time
that they weren't going my way.
And that's not the same as
saying, well then I just
defer to everybody every time.
That's, that's not
the same thing.
Sure.
But if, if you were to say,
Hey, my way or the highway
that ends poorly, yes, you
can force enough things, but
eventually that will break
for sure.
Because if you manufacture
alignments, you somehow
cobble it together, right?
It's gonna bend
back outta shape.
Right?
The type of alignment will fade.
Uh, the thing I
like, empathy lasts.
We know this, so if
you can't, it's point.
Always share the same goals, at
least share the understanding
right, of those differences.
Then I think you, you've
got, you got something
you can build from.
At that point,
I always say, you
cannot change people.
You can only change your
understanding of people.
And so I'm not gonna
change my wife to be this
risk taking maverick.
Right.
This is not going to happen.
Right.
And by the way, who the
hell am I to even suggest
that she should change?
Right.
Right.
That, that would, that
could actually go perfectly
horribly for
me.
Right.
For all we know,
right?
I my only control valve.
But I can change my
understanding by saying, Hey,
this is what makes my wife tick.
These, these are the
things that concern her.
These are the things
that excite her, right?
Like and understand that,
that when I bring to the
table shit that concerns
her, I shouldn't expect a
high five answer, right?
I should expect right.
A pushback because
that's who she is.
Conversely, when she has a
conversation with me, she
should know that my answer is
gonna be, fuck it, risk it all.
Like, let's see
what happens, right?
Let's see what happens,
right?
Let's see what happens, because
I'm okay with that because
I, yeah, I'm okay with what
happens on the other side of us.
See what happens.
'cause I always figure it out.
But again, I think what's
killed me for a long time,
I get it now, which is why
we're talking about this now.
What killed me for a long time
was one, not acknowledging
myself in the second.
I wasn't good.
I am now.
I wasn't good at saying
I understand where you're
coming from, Uhhuh.
I understand why what I'm asking
is antithetical to how you're
built, and I recognize that.
I would say my batting average
for people giving me the same
consideration is almost zero.
Yeah.
I didn't say it work
the other way too.
The other way too.
Well, I haven't had an
employee come to me and say,
you know, will I understand
that your consequences are
pretty significant and mine
really aren't that high, so
I'm gonna work a little bit
harder just to help you out.
Pretty much heard that.
Never,
yeah.
I don't think I've
heard that one.
I don't think I've
heard that one.
No, but look, that goes back to
understanding and acknowledging
and respecting that difference.
There's, there's a reason
they're not saying that to you.
Right?
Right.
Yeah.
There's, there's a fundamental,
there's not a reason for them
to say that to you, I guess
is a different way to put it.
Great way to put it.
Great to put it, yeah.
And so I think that,
yeah, go ahead.
I was gonna say, so like, you
know, I used to think that like,
with alignment, it was, I just
needed to convince everyone
that my way was the way to go.
Not, not being like, like a
jerk about it, but just like
I, I thought, I thought that
was my job was to convince
like the team that this
was, you know, the future
path to work really hard.
All these things, and I realize
just a little bit of it is.
But like 10%.
Right, right.
Like enough to say, Hey,
just by the way, here's the
direction I'd like to go.
The other 90% of like making
them do it because I wanted
them to didn't, never went well.
Like it.
No.
I dunno
how people think that worked.
Well, no,
I, I think we have to stop.
You just have to, at some point
you just have to stop trying to.
Erase or correct
the misalignment.
I think now asymmetry
is literally architected
into a founder's life.
Like what we are trying to do by
its nature is asymmetric, right?
We're trying to take something
and it's nothing and make
it into something huge.
Right?
Asymmetry at its at,
its its best, right?
We're gonna just absolutely
try to, to scale something.
I think the real trick is not
letting it break relationships
as we go, because I think
that perfect alignment is,
is it's, it's a myth, right?
I don't think it's
something we even.
Can force function evenly.
Not if we try really hard
think, we'll break ourselves
doing it mutual respect,
like that's always in style.
Right?
Right.
That's how you keep building,
um, to the point where you
maybe you do reach alignment.
'cause again, it's really easy
to be aligned in the good times.
Right.
Right.
You gotta get there.
No one's ever had a, a huge
problem because we're making
so much money and we just
don't know where to put it.
Right, right.
And if you do no.
In the brown bags.
No.
In the green
bags.
Ha.
Happy.
Oh, you know what's so funny?
This just reminds me of
the dumbest story, Ponzi,
I can't remember the guy's
first name, but like Jeffrey
or something like that.
Ponzi actually had this problem.
You know, the Ponzi scheme
comes from a guy named,
uh, last name Ponzi.
And, and as the the myth goes,
there was a time that Ponzi was
making so much money that his
issue was, he couldn't figure
out where to put it 'cause
he couldn't put it in a bank.
So he was like stacking
it in apartments or
something like that.
Like
yeah.
Oh, that's amazing.
My rats and all that.
Yeah, yeah,
yeah, yeah, yeah, yeah, yeah.
Oh yeah, that was, um, that
was, I suppose in extreme
cases it could also
cause fighting.
But I guess the point, you
have so much money, you
don't know where to put it,
and the rats are eating it.
You're probably not
fighting about money.
Yeah.
You're gonna be okay.
You're gonna be okay.
So,
so here, here's what I'd
say like for all of us
that, that are trying to
like fight this battle.
The way to win this battle
is to fight it less.
The way to win this battle is
to zoom out and say, here are
the things that I can control.
Way less than any of us think.
Think it is.
And here's the things
I can't control.
The reality is you can
control your own perception.
You can't control other people.
So if we want alignment,
alignment has to come from.
Our understanding of what
can be controlled in.
And by way of that, what can
be compromised in what can't.
And the sooner we get to
that point, the sooner we
kinda like take our hands
off the wheel for a second.
It's like, you know what, I'm
not gonna get everything I
want out of every everyone.
So I wanna get as much
as I can out of everyone.
That will be the only
thing that will ever get,
that will get even close
to a perfect alignment.
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.