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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
joint, as always by my
friend, the founder,
and CEO of startups.com.
Will, Schroeder will,
speaking of friends, speaking
of friends as as founders,
often, uh, I think we, we have
this feeling that like, you
know, we, we wanna call our
startup a family and hug fest.
Culture can feel great,
uh, right, until you have
to fire cousin Eddie.
But like, well, like maybe
early on, especially we, we
wanna be everybody's friend.
But I think one of the things
we wanna dig into today is like,
does everybody actually wanna
be our friend, right, as the
founder, does everyone want to
reciprocate that relationship?
Where are the boundaries?
Where, where do we need to
draw these lines between
like, let's say healthy
empathy and the potential
for a liability hangover?
Yeah, it's a great
way to put it.
It didn't occur to me for
a long time that people
wouldn't want to be my friend.
Like this is me
being narcissistic.
I mean, it's just me being
more like, just unaware.
So Ryan, early in our careers,
we both got started, you know,
very early, like, you know,
in our early twenties and at
the time everyone was just
like naturally peer, right?
Yeah.
So like all of my coworkers
at Blue Diesel, my first
company, interactive agency,
were all my age or older.
And by older I mean
like I was 22 let's say,
and they were 26 or 24.
I mean like I remember we
had one guy that showed up
and he had turned 30 and
we gave him endless crap.
I'm sure we bought him a cane.
We like it just like it.
And it was funny.
Is as crazy as it
sounds now, right?
What's funny is we
are fairly serious.
Like, like we're like,
dude, you're aging
out right?
Right.
Yeah.
Yeah.
They, they, but on a
relative scale, it was
significantly older.
But I think there's
something to that will Yeah.
And it'd be interesting to,
to talk to some founders
who started a bit later
in their founder career.
Yeah.
To see if that same
muscle got built.
One of the things that I
realized was that because of the
age which I started and because
of the things I was foregoing
by virtue of having started
a company, we've talked about
this on other podcasts, right.
Wasn't going out to
parties, didn't join a frat.
Yeah.
Wasn't dating a lot like
all these other things
that I was foregoing.
Yeah.
And late nights working.
Right, right.
Always on thinking
about the business.
So I didn't have room for
socialization, friends and
other family, so I adopted or
wanted to adopt my colleagues.
Yep.
As my friends and my family
based on my own need.
Now, a lot of them, all of them.
Had a very different level of
attachment to the business.
It wasn't their business.
Right.
They were working for me
out of my college home.
Right, right.
Yes.
There was a cool Counterstrike
server that we had at the end of
the day and they all loved that.
But if I turned that off,
I wonder how many of them
would've left immediately.
Right.
Point being they didn't
have the same need.
They could go out at five or
six o'clock when, when work was
done for them and have a normal
life and have other friends
and have family relationships.
I didn't, and so I think
part of what set that pattern
of my startup is my family.
Was, I didn't have
an alternative.
Yeah, I get it.
And you know what?
It didn't occur to me
that anything could
go wrong in my mind.
Like what could
possibly go wrong.
And now having done this for
over three decades and across
nine companies across lots of
different staffs, yeah, I'm well
aware what can go wrong Now?
A lot of stuff can go wrong.
And what's crazy is it
goes wrong with what I
would call across the board
wonderfully good intentions.
Wonderfully good
intentions, right?
A hundred percent.
Like not, oh, like, you
know, we're, we're, we're
trying to make people
our friends or whatever.
It was like, I genuinely
care about you.
I care about your welfare.
I wanna see you do well.
Right?
Like, everything you
would actually want out of
a friend, and these are
the people you spend
your waking hours with.
Like, most of my, all,
all of my day that I
spent with other people.
Was spent with
those other people.
When I hear startups
say, we're a family
here, you know, together.
And all I think to myself is,
that's gonna end so poorly.
Yeah.
Oh my God.
I've got a great
anecdote for this one.
Yeah.
Yeah.
At some point I made a post
along these lines, which
is the like, and, and I, I
used, somebody else probably
dropped this before I did,
but I had been using the, the,
the metaphor of, or the, the
analogy of like, it's more
like a professional sports
team than, than than a family.
Right.
And somebody came
in and started.
Heavy trolling, this
LinkedIn post heavy
trolling, this LinkedIn post.
And so I was like,
I'm just gonna go over
and see who this is.
Some management consultant guy.
Right?
I don't remember who
he was at this point.
Some management consultant guy.
I looked through a couple
of his, a, a couple of his
posts and I, I get to like
the third or fourth one.
You can't make this shit up.
I get to the third
or fourth post.
And what does it say?
There's only one thing
worse than working.
There's, there's one
mistake you can make worse
than working with friends.
And I was like.
Okay, go on.
That was the hook,
the punchline.
Working with family.
This is the guy who was telling
me I was wrong for saying that
a company shouldn't be like
a family is literally saying
the only thing worse you can
do is work with actual family.
It's like, okay, so you don't
wanna work with actual family?
Well, he wasn't
wrong about that part though.
Turn your
employees into family.
Like, yeah, come
on.
I, I think there's a ton
of genuine danger here.
And again, I think as
founders, all of us, we go
into this idea that I want
to be friends with everybody.
I want this to be a family.
I want this to be tight.
I want all these things.
And I, and I genuinely believe
that has great intention.
What I also believe and
certainly have seen is that
that also has the ability in
more cases than not to backfire
so badly.
Big time, man.
Big time.
If your org chart could easily
replace your Thanksgiving, uh,
seating plan, good luck to you.
When it comes time to trim
headcount, when people have to
be replaced, when, when people
need to be reprimanded, when
whatever ends up happening,
man, if it truly does feel
like that level of family.
It puts up all kinds
of blockers and false
expectations on both sides.
There's so many things
that, that we talk about
in this podcast that we say
only work in good times.
Ryan, if you can think this far
back, one of the first episodes
we did was about whether the
founders should be transparent.
Like be transparent about
everything in the organization.
Yep.
And I remember I said back
then, I said, that only works
when things are going well.
Yep.
When things are going crazy.
Transparency sounds awesome.
Right.
You know, here's how much
money we're making, how fast
we're doing over, around.
Yeah.
We off to be
acquired.
Oh, high fives Be transparent.
Tell me more.
Yep.
Let's money build in
public money for payroll.
Shut up.
Turns around really quick.
Yeah, this is, stop talking.
This falls in the category of
when it's good, it's great, and
when it's not, it's terrible.
Let's unpack this a little bit.
You know, let's kind of break
down like where it, where it
falls off, you know, goes off
the rails, why, and kind of
what we should do about it.
Right?
Kind of how we
should approach it.
Yeah.
'cause I think the, I think the
startup family myth is like.
It's super seductive, right?
It's, it sounds great.
It does sound great.
And, and I think it's one of
those things where we might
even enter into it with slightly
different thoughts and then
I think as you realize, what,
how is you always put it
running naked into the abyss.
Yeah.
And you're running
naked into the abyss.
You're like, it'd be
nice to have some friends
and family around to, to
help me out through this.
Right.
And so then I think even if you
started off with the intention
of like, no, no, I'm gonna
run this very professionally.
All of a sudden those lines get
really blurred because mm-hmm.
You have an emotional or
psychological need for that.
Let's talk about how the,
where that comes from.
Okay.
And, and you've talked
about it in a number of
ways, but I, I think the
startup experience breeds it.
Okay.
So the first thing
you deal with the.
Is, uh, shared risk,
shared terror, right?
So it's like, Hey, we're
all in this together.
We're all putting our hearts in.
We've all risked
significantly to be here.
So we have that commonality.
Yes, it's soldiers in a foxhole.
We're all fighting the
same battle together
at the same time.
Yep.
Which breeds incredible,
uh, trust bonds,
communication, et cetera.
And all those are wonderful.
All those are wonderful.
However.
Where it starts to break is
often that bond that has to do
with being in a foxhole together
gets mistaken for a different
level of friendship, or, yes,
the concept of friendship
gets mistaken for work.
Right?
Right.
And so you and that person are
fighting side, side by side,
and it feels like, oh my God,
we're so tight, we're so close.
This is, you know, my brother,
my sister, you know the family.
Right?
And then things go sideways
and you're like, huh.
All of a sudden that metaphor of
family doesn't hold up at all.
It doesn't.
And I think the challenge
there is that we misinterpret
shared context as shared
perspective, right?
Yeah.
Or friendship.
You can go through the
same context and have very
different perspectives on.
I think that we start to
superimpose our perspective on
the folks around us sometimes,
and that can be really tough.
But again, where
does that come from?
It comes from the fact that
we, we've talked about this
podcast probably 20 other
times in different ways, but.
When we need somebody
to talk to, who else
are you gonna talk to?
Your friends and family do not,
this person has perfect context.
They don't have any
understanding of what
you're going through.
So at least with the team,
there's the shared context.
They see, they understand
some of the struggles, maybe
at the same level you do.
Mm-hmm.
But they have more shared
context than anyone else does.
But that does not mean they have
the same shared perspective.
Right?
Right.
You're looking at it
down from the top.
They are not, they're some
version of looking up to you
or at you, and that's gonna be
very, very different for them.
There's also not a lot of
relationships or situations.
I think this is important
for the, for the construct
of, of friendship.
There are not a lot of,
a lot of other situations
where you become friends
with someone where there
could be a very specific.
Externality that forces
you apart, right?
Ergo we lose a
funding round, right?
Her name was April,
but yeah, it was April.
Screw her.
No, but like, one of the
interesting things about
a startup and, and we did,
uh, again, one of our first
episodes, we did an episode
around what we call, uh,
startup shedding its skin,
that as a startup grows and
evolves, the people within
the startup, sometimes the
founders inclusive, don't
always grow at the same rate.
Right.
And so when you're first
starting, and the guy who
came in as the CFO was the
only person that took an
accounting course in college.
Right?
Right.
So that, that was
his credentials.
Yep.
As the thing grows.
And you need real finance
from a real CFO, that guy's
out of a job all of a sudden.
Yeah.
And you feel shitty because
you're like, oh man, he was
in it from the beginning.
He worked so hard.
You know, thi this is
somebody I care so much about.
And it's like, yes, but
the circumstance yes.
Has driven a wedge.
The circumstance has
kind of pried that apart.
And the problem in startups
is that circumstance
is almost a given.
Right.
Right.
That stuff's gonna
happen at some point.
Yeah.
We've talked to this before.
People grow at different rates.
Startups grow at different
rates, but like when the,
the startup outgrows one
or more of the members, but
not the others necessarily.
Right.
If, if the CEO and the COO
and the CMO have all moved
along and, and the CFO is
somehow lagging behind.
That gets really tough, right?
It gets really,
really hard.
One of the first times I started
a company and my co-founder
was a good friend of mine,
when the company started to do
poorly, like we did a fairly
good job, I think, of like
maintaining our friendship.
But in the end, if I look back,
this is like 20 years ago,
but like when I look back, it
did end our, our friendship.
Like we still talk to this
day, but we're not friends
the way we used to be and
kind of what brought us there.
And I think about it a lot.
I think about like.
What could we have
done differently?
Okay.
Right.
And the answer is not much.
Because essentially, again, this
externality of the startup drove
a wedge in our friendship that
had a real cost to each of us.
He was a great guy.
He did nothing wrong, right?
Like, you know, uh, and nor
did I, like, not neither
of us did anything wrong.
It just didn't work out.
But at the time, it created
enough of a wedge, enough like
hardship between us that it
kind of busted our friendship.
And that's at a
co-founder level.
Like somebody that you're kind
of supposed to be tethered to.
If we take it back a step when
we, you know, start looking
at all the employees in the
company, that's even more
significant because with that,
where we've got all these
employees, they come and go.
Yeah.
I mean, they're like, Hey
dude, I got a better job.
Peace out.
Right?
Yep.
And you're like, oh, I
thought we were friends.
And it doesn't occur to
you that you are friends
and this is a job.
Yeah.
This is a job.
And that's another job.
Yeah.
Yeah.
It's funny because we
can, we can clearly
separate that, right?
Like if your friend
works for pwc.
Yeah.
And then he, he moves over
and decides to work for.
Someone else, like you don't
stop your friendship with
that person because they
no longer work for pwc.
Like who cares?
Right.
Right.
Because that's not what your
friendship was predicated on.
When your friendship is
predicated on the fact that
there was the employment and
that somehow it co-mingled and
that becomes a, a much more
difficult thing to navigate.
Said differently.
The idea of building a
friendship solely based on a.
Startup, whatever it lives
by it and dies by it.
Like it works as well
as the company now.
Now there's another way
I've seen that relationship
strain, which wasn't,
hey, we ran of money.
The other way I've seen it
strain is, like we said a
moment ago, where the startup
just keeps growing, right?
And that person simply
doesn't grow with it.
When we were growing the agency,
we grew so fast and a lot of
the people that were there
from the start felt entitled.
And usually that's
a negative word.
It's the one time where
I'm not gonna use it.
Uh, negatively felt entitled.
Like I thought this
was like how we grow.
I thought I was doing what
I was supposed to be doing.
Yes, they wanted to work hard.
This wasn't a right.
Um, I'm not gonna work hard
and I deserve it anyway.
This was a, I literally
thought this was how I advance.
Right.
Like by this thing growing,
I helped make it grow.
It's bigger.
Why aren't I still at the
top of that org chart, Uhhuh?
And it wasn't their fault.
Just we got to a point
where the person that needed
that role needed to have
significantly more experience.
Different experience.
Yeah.
Yeah.
And it happens.
And so those relationships.
Got beat up because they
looked at it as like,
Hey, you passed over me.
You know, et cetera.
And it's like, damn.
That's in my mind, the best case
scenario, best case scenario.
We're growing like crazy and
there's more opportunity.
It never occurred to me.
That you wouldn't get it.
So that could strain as well.
Yeah.
Again, I think it goes back
to that like you're, you're
using the shared context
and assuming that there's
shared perspective there.
It's hard to do.
To be fair, the founder kind
of gets a bit of a, a pass on
some of this because they're
the founder, they're kind
of baked into that role.
However, however, they
also have all eyes on me.
Yeah.
So like, if you're head
of customer support and
you're a little bit over
employed, so to speak, right?
You know, uh, uh, you're,
you're, uh, this job's a little
beyond what you should be doing.
You might get some shit
if you're the CEO or the
founder or whatever, and
you're over employed, you
don't know what you're doing.
A hundred percent of the
people in the organization
are hyper aware of that.
As our investors, as
our customers, the
media, what have you.
It's harder to duck
that kind of scrutiny.
Sure, sure.
Regardless, we're all gonna face
it in good times and bad times.
There's going to be friction.
There's going to be a driving
wedge in the early formative
years when we're building the
company and everybody's coming
together for the first time.
Right.
It just hasn't happened yet.
It's like a married couple
that hasn't had a kid yet.
They have the kid, they're
like, oh my God, it's
gonna be so much better.
Like, ah, not necessarily.
It's gonna be
different.
Yeah, yeah.
Be better.
You have actually harder,
you know what I mean?
Yeah, for sure.
And so I, I think that these
are the kind of things that are
super hard to spot because in
the beginning, none of those
consequences exist, right?
None of the consequences there.
It's all upside.
Like absolutely on those
early days, it's all upside.
Being friends and turning
your coworkers into a
family, it's all upside.
The upside is a
bit limited though.
Right, because there's a
level at which it doesn't
continue to propel anything
within the company.
It's not like, I don't remember
hearing too many stories.
I'm sure there's some out there.
Somebody will, will reference
one formula to prove me
wrong, and that's fine.
We'll call the exception
that proves the rule where,
because of the fact that
we treated it like a family
or because of the fact that
we, we were, we were friends
that that was what drove it.
Now, I'm not gonna say
there were never businesses
that didn't have this.
Show me objective proof that
says, because this, right?
And there was something that I
wouldn't have otherwise done,
but because I considered you a
friend, I did this and this led
to the success of the company.
I can't name a one, right?
I can't name a single one.
Right?
And so again, there's a peak,
there's a limit to what the
benefit of doing this is,
but it feels so good in the
beginning that you'll do it.
And then there's just a super
diminishing return and there's
a bunch of really, really.
Heavy taxes that can come
out this when it goes south.
Right.
Well, and again, I'm gonna say
those taxes are inevitable.
Right?
It just in the Yep.
In the early days you don't
see them Again, I, I'm gonna,
I'll put it like marriage, but
I think there's a side of this
that we should also explore,
which is, it's not just that
this thing could backfire on us.
Yeah.
It's that I don't know
that the employees
signed up for it either.
No, I, I think that's
the implications, right?
Like, I'm gonna make
us all a family.
They're like, I have a family.
I'm not even that fond of them.
I don't want another one.
Right?
Okay.
So,
so lemme tell you how I've
seen this evolve pretty,
pretty consistently, and
I think the folks in the
audience will probably be,
be able to align with this.
The first core group of
people that we bring in.
The numbers are relevant,
but let's say it's the
first five or 10 people Yep.
Spend an inordinate
amount of time together.
Right.
Yes.
At a very specific formative
stage of the company where
they're all like making the
baby together, so to speak.
Formative decisions.
Seminal work.
Yep.
Everyone's contributing.
Like the funny joke
everyone gets, because
you can say it in a way
that's literally contextual
to every single person.
Yeah.
And everyone has that, that
shared perspective, et cetera.
Now, person, I'm just
making this up, 50 shows up.
Okay.
Yeah.
And they don't give a
shit about any of that.
Right, right.
They don't care about
your inside jokes.
They don't care about,
like, the fact that you
wanna go out for beers.
They don't, they don't
care about any of that.
They took this job,
I just did this last
week.
What's that?
I just did this last week.
Do you remember?
I referenced an inside joke
that I think you, me, and
one other person got, and
it didn't occur to me until,
no one reacted that no one
else had that shared context.
I had just forgotten
how far back that was.
How much the
organization has changed.
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 Ryan, I've got a
great throwback for you.
Early in the days of this
company, you'll remember
who this person is.
Of course, I'm not gonna say
who they're, but we were a
very freewheeling family.
Right.
Everyone was super tight,
if I'm being honest.
It was almost all
dudes at the time.
Right.
So had a very kind
of frat feel to it.
And we hired a, a, a, a
woman outta college, maybe
a year or so out of college.
Pretty straight laced.
Pretty buttoned up.
Definitely not aligned with
how this company was running
it.
She was not in the
bro adjacent space.
She was not
in the pro adjacent space at
all, and this is my fault.
Did not occur to me.
That was a problem.
And it wasn't a matter of
being insensitive, it just, I
didn't understand the delta.
Right.
Because up until that
point, we didn't have one.
Everyone was on team.
Bro.
I know that that has
such a horrible, uh,
connotation right now.
It wasn't.
Maybe it was that
bad, but I don't know.
Uh, point is everyone was
so happy to be there, right?
It didn't occur to me
that someone could show
up in this environment.
Not enjoy it.
Not enjoy it.
She showed up in
this environment.
She did not enjoy it.
She did not enjoy it.
Right?
Yeah.
Now, to her credit, I even
said this to her, you know,
years later, in her last day,
I said, you fundamentally
not only changed the cultural
course of this company, yes,
some for the better, some
for the worse, but you also
helped me understand it, like,
help me understand the delta.
So she said to her
credit in all of our benefit,
right?
Yes.
She, she sits me down,
I can tell, like this
is welling up in her.
Okay.
And she's like, will, I
don't feel like the culture
here is as professional
as it's supposed to be.
And I'm like, high fives right?
And she's like,
no, not high fives.
Fist bumps.
Exactly.
Chest bump.
Right.
And, and again, Ryan, you
and I are two the most
empathetic people I know.
Like, and so before you
hear this and say, oh my
God, those guys are a bunch
of douche bags, you'll
probably write about that.
But please understand
that like we also listen
incredibly closely and so
she sits down and doesn't
mean we're not
ignorant sometimes.
Yeah, exactly.
Look, we all make mistakes.
And so she sits down and she's
like, look, we've got rap music
playing all day throughout
the the office, right?
Like.
It's fairly appropriate, right?
Yeah, exactly right.
I I was like to, to take
that off the website.
Is it making it hard for you
to hear the NBA jam machine?
Yeah, because we can, we
could, we could turn that off.
She was like, she was like,
people are playing video games
in the, uh, middle of the day,
which is very distracting.
She said that people talk
about their personal lives
with no boundaries whatsoever.
And at the time I'm
like, okay, fun, please.
Thanks.
Right.
But I realized, and again
this is, this is to her
credit, she made me realize
that because we were on
board didn't automatically
make everyone else on board.
Correct.
And I was like,
damn, that's heavy.
Yeah.
It's back to that same,
it's that shared context.
We were all in that
same video game.
Testosterone driven rap
background, music environments.
But the perspectives
were, were different,
right?
At least one or two of them
were, and she was, I mean,
obviously she wasn't wrong
and, and I remember coming
home and talking to my, my
wife about it, and I'm like,
it's killing me because she
basically fired a bullet
in everything that I enjoy
about this company and it's
killing me that she's right.
And my wife was like, you
had to know this was coming.
And I said, what kills me is
I didn't know it was coming.
Yeah.
Also, no.
Yeah, no.
And, and, and again, not because
I, and we changed, we modified
the culture because of that.
We got a snowboarding game in
the basement instead.
It was way different.
What I think is really
interesting about this is
when we build this family
culture, when we had to decide
we wanna be friends with
everybody, we easily overlook
that because it's good for us
and we signed the contract.
We're not allowed to just
sign everybody else up
too and be like, it's your
fault if you don't like it.
It's exactly it.
I, I think that, you know, we,
we do understand consent in a
lot of ways, but I think that
consent also applies to culture.
Right.
And I think that we, we just
have to be very careful about
presupposing, that everybody
wants emotional VIP access.
Right.
Right.
And it's their right
to not have it.
It took me a long time not
to understand why it's not
their right, the right part.
I understood right away it was
that they wouldn't want it.
Because I did, right?
Like I wanted to share
how things were going in
my life with everybody.
I wanted to hear about how
things were going with everybody
else and, and I think this
is a very big part of like,
probably what makes us very
active advisors, Ryan and
parents, et cetera, is that
we wanna help when someone
says, man, I had a really tough
situation, like personally
our first thought, and this
is literally what we do here.
Is to help.
My
wife
gets on me all the time.
It's hard to be
empathetic without
information, right?
And so we seek that information.
I
like, my wife gets
on me all the time.
She's like, well, you
don't realize people have
boundaries that you don't have.
And even when you're well
intentioned, when you're trying
to help, you're still crossing a
line that someone else may have.
Right.
Yeah.
Like we'll be at
dinner with a couple.
We don't know that.
Well, and I'll, I'll hear one
people on the other side of
the table, like complain about
something and so I'll just start
asking 'em questions about it.
I think you're aware of
this, most people don't
ask like meaningful probing
questions, kind of like
a psychiatrist would.
Right.
That was the only
questions I have.
Right.
Yeah.
I've been capable
of small talker.
I don't care what the
weather was like that day.
Yeah.
Like tell me about
your relationship with
your, with your dad.
Why you crying?
Yeah.
Yeah, exactly right.
And Sarah's like, look, they
didn't sign up for that.
Like, that's just because
that's your default.
It's not their default.
It makes certain people
very uncomfortable.
I know you, you mean.
Well, but that's, it
is still not okay.
Yeah.
I blew my mind full.
I get it now.
It, it's not even
just the questioning, right?
It's not even just the
questioning, because like, I
think even just oversharing
can become invasive.
You may be exposing 'em to
things that they don't wanna
know, but I think the, the,
the larger symptom that I've
seen when, when I've become
guilty of this is that.
People feel like they have to
reciprocate a hundred percent.
Yeah.
Right.
They feel like, ah, because
you're doing this, you're
trying to draw this outta of me.
And maybe I probably was right.
But again, from a
well-intentioned place
of wanting to be able to
be empathetic and wanting
to understand, you know,
what your context is, but
not everybody signed up
for that, like you said.
Right.
They, they're here,
I'm here to do my job.
I'm here to like
run social media.
I didn't ask to join
your therapy hour.
Right.
Either as doctor or patient.
Right.
It's not, not why I'm here.
Um, so I think for me
it's like at this point.
I still do welcome those
interactions, and I
don't, I don't shun them.
I don't push them away.
I don't, I don't deny them.
But I think the, the thing
I'm trying to do at this point
is to default to professional
distance and let the team invite
deeper, more personal rapport.
Yeah.
And I, I gotta say, I hate it.
I hate it.
Yeah.
Um, I'm doing well, itm exactly
what you're doing and I hate it.
It's because we're impatient.
You wanna know it's,
it's because I literally
wanna be helpful.
When I see somebody and it
looks like they're struggling
in some way, my first instinct,
even to strangers, I don't
even know who they are.
Right.
My first instinct is
to try to be helpful.
Uh, again, I'm the person
that when I see you, like
you're got a flat tire on
the side of the road, I
will pull over to help you.
Yes.
Right?
Like that's my first instinct.
It doesn't occur to me that
you wouldn't want my help.
Right?
And again, that that can be
annoying in its own right.
But now if we institutionalize
that, if we make it so
that like, Hey, you joined
this company, and I guess
we're all gonna share
how our weekends went.
Yes.
And you're at lunch or you
know, in a conference room
or something and you're
like, I don't wanna tell you
guys what I did this week.
I know your goddamn business.
Right.
The emperor's new
clothes come to mind.
Like, it's one thing when
the emperor's walking around
with his new clothes on and
everybody has to suffer through
seeing the the emperor nude.
It's a very different thing
when the Emperor asks everyone
else to don those clothes
too, or they feel like they
have to, then it becomes a
very different situation.
And I don't think we do it
intentionally or deliberately.
No, I, I think it's
done by circumstance.
I think, you know, we create
this culture where you and
I in a meeting start talking
about how our weekends went
or how things are going with
our kids, and then by proxy,
everyone else in the meeting
assumes that they have to
contribute at that level,
especially if we're there.
Yeah.
Their boss, et cetera,
and that makes people
freakishly un uncomfortable.
Yeah.
Now some people are like,
this is awesome, and they
gush and they can't wait
to talk about what they
were doing that weekend.
Where it becomes a problem
is for that employee that I
mentioned from years ago that
was brave enough to stand up
and say, Hey, I'm not okay
with this, and, and have us go.
Really, and not in a way where
she deserved that recognition,
uh, and deserved the response.
What, what threw me off wasn't
that she asked, it's that it
didn't occur to me that, that
she would, and you know, that
that certainly, you know,
left a mark in a good way.
I also think that as we get
into this, if we look Ryan,
if we look at both the side of
it, where we're overstepping,
abound, you know, like we're
sharing too much and the side
of it where maybe our employees
don't want to, yeah, I think
we need to step back and say.
I've gotta tread very carefully
on this notion of what these
relationships are, or how deep
my relationships are gonna be
with people, because one, if I
invest heavily again, that wedge
that's gonna break this thing
is right around the corner.
Right?
Yeah.
Just the nature of startups,
they're very fickle, right?
Shit's gonna go wrong, and,
and things can go wrong
in a positive way too.
People think, oh, you know,
we're run outta money.
Things can just scale very
quickly and that person
doesn't, you know, make sense
for the job or just anything.
Or there's another version
where that person, uh,
has nothing to do with
what the company's doing.
Just like maybe doesn't
get along with people
anymore, or just like, is
maybe just a bad apple.
Yep.
They're your friend, but
nobody else likes them.
You know?
Nobody else.
Yeah.
Yeah, yeah.
And then the other side, like
I said, is we're creating a
culture that almost demands
this level of, uh, inclusiveness
of like openness of et cetera.
And while those words sound
great, they don't always apply,
and especially not when,
when they become the
currency that feels like
it buys you into the club.
Totally.
Right, right.
Yes, absolutely.
That's where
it really goes south, where
it's like, well, I have
to have something know.
Go home and talk to your
partner, like, we're gonna have
to adopt a cat or something.
So I have something
to talk about.
Right?
Everybody's talking
about their kids.
It's like, I, we gotta, I gotta
have something, I gotta have
something to contribute here.
It's so funny you should say.
That's where it becomes
really problematic.
I remember having this feeling.
Okay, so yeah.
Yeah.
When we were growing the agency,
it was getting bigger and bigger
and we built a board, an actual
board, like, and they were all
like the operating heads of the
different parts of the company.
We had about maybe 700
people at the time.
I was the youngest
person in that room.
Buy a lot.
Now, when I say buy a lot,
I was probably 26 at the
time, and the average person
there was like 42, but
everybody had five kids or so.
It seemed.
Everybody loved golf.
Everybody had all these things
that had nothing to do with me.
And I remember then we'd go
on client meetings and we'd
be with client from Best Buy
or BMW or whatever, and that
dude would be 42 years old with
five kids in a golf membership.
And all people would
talk about instant
camaraderie.
Right, right.
Was five kids in
a golf membership.
And I remember thinking
like, this sucks.
And feeling so on the
outside feeling like, like
I, I'm not even kidding.
I took golf lessons just so
I could know what the hell
these guys were talking about.
'cause they were, they
thought their golf puns and
jokes were so goddamn funny.
Turns out they're not.
They're actually super
stupid and I have no idea
why people get so like,
worked up about them.
You are like, oh, you
overshot on that one.
Oh my God.
Right?
And everyone's like
belly laughing.
I'm like, what the
hell is going on here?
Right.
But I remember feeling so much
on the outside because they
had a a, a compact between them
that this is what we're gonna
share, this is what we're gonna
value, and if you contribute,
you get high fives and respect.
But if you don't.
You're ousted, you're
just on the outside.
Yeah, just, and, and again,
I I say this to say, as you
know, a middle-aged white
man, like, you're, you're,
you just assume that I'm
always on the inside, right?
Like it's just kind of the
way the world looks at it.
And Yeah, some we're sometimes
on the outside too, and it all,
it does feel really shitty.
And now you think about
like the instantiating
that into a culture.
However you, you know,
build that culture.
I'll give you an example.
There are certain cultures, I'm
gonna use Google in this case.
Okay.
That was, uh, it is an
incredibly liberal culture
and they've had wildly big
problems with folks in their
culture that were not liberal.
Right?
Yeah.
Uh, if you remember
that, that one developer
that they had Yeah.
Uh, that sued Google and
I think won for like a
hundred million dollars.
Yeah.
Yeah.
It was a, they basically saying
like, I don't identify with
your politics, et cetera,
and I got fired for it.
And I thought to myself,
it's a problem because it
lacks a certain amount of
self-awareness on Sure.
Within Google as the
culture they had created,
well-intentioned as it
were, that it was actually
becoming a problem for itself.
You
know what I mean?
Yeah, yeah.
Anything taken to an extreme
tends, tends to do that.
But I think it's
interesting, right?
Like I think this is where like.
We have to be careful
where Founder Ego enters
the mix here and can
absolutely stomp all over
organizational clarity, right?
Like where we, we start to
believe something fundamentally
and we wanna make that true.
Does everybody else want to?
Right?
Going back to that whole,
the, the, you know,
culture needs to have some
implicit consent to it.
And I think, you know, kind of
back to your point around like,
I just want to fit in here.
I want to be part of this.
Wanting to be liked should not
be equal to being effective.
And of course that's not
what we're trying to create.
But I think that's the message
that can get sent too, right?
Which is if you conform to some
of these things, if you start
to fit in, if you start to
reciprocate in these ways, then
you'll be liked, and that seems
to be held in higher esteem.
Than being effective.
Right.
Imagine the message
that sends to people.
Yeah.
It's, it's dangerous.
I, I think, you know, kind
of what this maps back to is
that we need to, to lead and
we need to organize within
ourselves around respect.
Not friendships.
Right.
And, and there's nothing
wrong with friendships.
Friendships are wonderful,
but I think we need a
different construct.
And, and I think someone
like Reed Hastings,
the founder of Netflix.
Yeah.
He leaned into this heavily
at a time when it was
not popular to do this.
And he actually had this like
hard coded into their, their
company manual or, or cultural
code or or whatever you call it.
And he was very public about it.
He said specifically, and
again, I believe this is
in their company documents,
we are not a family.
At a time when that
was like just heretical
to say, right, sure.
Like how dare you.
Right.
And here's what he said.
'cause he is just a smart guy.
He said, look, a family
is a family that is based
on unconditional love.
Right?
Yeah.
If Uncle Eddie is a jerk, or
he is the coolest guy in the
world, he's still in the family.
Right.
This is not that.
He said we are more like a
professional sports team.
Yeah.
He said we share a common
goal, we share a common good.
We may even share common
values, but ultimately if
we don't all contribute
and perform, uh, equally
or as well, we get benched
or removed from the team.
And I thought that was.
A much better metaphor.
Holy cow.
That would've been useful
information 30 years ago.
A little bit
too late.
Yeah.
Yeah, yeah.
Would've been a little easier.
I mean, yeah, when you think
about it, like it's yes, you
know there there are aspects
of a startup team that could
start to look like a family.
Sure.
Right.
But I think the analogy is much
better if we look at this as
a professional sports team,
because like at some point.
If you stop performing, we
have to stop putting you in.
Correct.
Right.
It's just numeric.
Also reverse it.
'cause here's the part that
we always forget, like what
happens if you, if you, if
you put the shoe on the other
foot, what if we stop paying?
Do you keep playing?
Because we're family.
Right.
Not for long.
Right.
Right.
And so I think that that's,
again, it, it sounds great
and good times when there's
any strife, any challenge,
then I think the, the
family metaphor breaks down.
But I think the question and
the question that they were
trying to answer, I think
this is the, this is a great
answer to this question is
like, how do you keep empathy?
Without eroding authority.
And that's really hard to do
in a family context, right?
The more empathetic I am,
the less authority I tend
to have with my kids.
Let, let, let me give
you another vector there.
Uh, tell me what you
think about this.
I think part of what he was
addressing too is that the
concept of family comes with
a fundamental entitlement.
Yes.
If I perform or don't
perform, I'm still family.
Doesn't matter,
we're still a family.
Right, right.
We may not like
each other anymore.
We might even speak.
We're still a family and, and
I think that's a dangerous
construct in terms of a,
of a company because again,
that entitlement always
ends poorly, always ends.
I've never seen an
entitlement where
I'm like, man, that
that worked out so well.
That worked out so well.
Well, in this case.
Essentially what you're doing
is masking consequences.
You're pretending that there
aren't consequences there.
Sure.
As shit are right.
You could have hired your
absolute best friends.
Right?
And I don't care.
It wouldn't have
matter what they do.
At some point.
Like if no one is
performing and there's no
money, no one gets paid.
There isn't some magic
bucket of money that we,
that we pay people out of it.
It's like, okay, this, this
does have real consequences.
And so I think it's dangerous
for us as the founder to pretend
there's no consequences, but
I think we never really can
truly avoid the consequences.
But for the rest of the
team, they also have to be
very clear that, yeah, there
are real consequences here.
And if we pretend
we're a family.
Where consequences don't exist
to that same level, we're doing
everybody a huge disservice
build on that.
So there's another side of it
where if the founder believes
that this is family, they build
an entitlement to say yes.
How dare you leave?
Right.
We are so tight.
No, dude.
I'm gonna leave the moment.
Some other opportunity
is a better, uh, dare.
How dare do you expect to raise?
Yeah.
Right.
I'm like, I'm gonna leave
as soon as there's another
opportunity that's, that's
a better, uh, opportunity
for my family, my actual
family, the people that
I have to provide for.
I'm gonna go somewhere else,
not because, you know, I
think you're the worst person
ever, but because you know,
I have better opportunity to
do something to grow, to get
paid, whatever, somewhere else.
So if this whole time you
founder person thought that
I was going to stay out
of some entitlement you
had over me about this,
this false construct.
Then shame on you again.
I've seen a lot of that where
I hear the founders either
their butt hurt because
someone left and they're like,
I thought we were so close.
I was like, yeah, you created
a construct, a force field,
essentially for this person
that they never asked for.
Whenever anybody's ever
left our organization.
Certainly anything I I've ever
done, I've never once felt.
They deserve to stay
because of some false
entitlement that I've had.
Yeah, I have said on certain
cases, like you worked here for
a year, did absolutely no work,
and took all my money, right?
And pissed
about that.
So look, I think when it's all
said and done, like we have
to be human, we have to be
kind, we have to be empathetic.
But we have to remember that
we are running a team, right?
We're not hosting
a family reunion.
We should shoot for respect,
sprinkle in some empathy, and
leave the group hug for later.
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