Startup Therapy

Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leadership. From discussing the rare contexts where pure honesty works, to sharing personal anecdotes about navigating the consequences of unfiltered truth, this episode unpacks how transparency can impact your team, brand, and personal relationships. Find out why being your true self might only be great advice 6% of the time and how effective communication can save you from unintended fallout.

Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/

Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

What to listen for:
01:01 The Consequences of Unfiltered Honesty
01:26 Generational Differences in Professionalism
02:44 The Power Dynamics of Founders
04:45 Balancing Honesty and Diplomacy
06:01 The Luxury of Honesty and Risk
08:04 The Importance of Filtering Communication
12:56 The Duality of Professional Personas
15:21 The Consequences of Honesty in Leadership
16:19 Balancing Honesty and Diplomacy
17:10 The Importance of Empathy in Communication
18:26 The Cost of Unfiltered Honesty
19:51 Frameworks for Effective Communication
20:55 Lessons from the Terminator: Choosing Responses Wisely
22:07 The Role of Diplomacy in Leadership
28:17 The Medium Matters: Hot, Warm, and Cold Communication
29:56 Prioritizing Outcomes Over Authenticity

What is Startup Therapy?

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,
authenticity is a

fuel unfiltered.

Authenticity is kind of
like spraying that fuel

through a flame thrower.

Um, so today I think it'd
be fun to talk about when

speaking your truth helps and
when it might just be nuking

your team, your brand, your
runway, your relationships.

If you had to put
a number on it.

About what percentage of the
time do you feel like being your

authentic self is a great idea?

I think if we really ran
the numbers, and I feel like

maybe I have, I think just
be yourself is wonderful

advice 6% of the time.

I might be generous on that.

Do you feel

like that's true for everyone
or are you giving yourself

a very specific score?

Is that just general?

That number would be, everyone
needs to adhere to this number.

That number would be way lower.

I'd be like, just be yourself.

It never will.

Just never, ever, ever.

And you know, I always
say this thing, right?

And I say like, when I come home
and I talk to my wife about my

day and stuff like that, she's
like, well, why didn't you

say that when you're at work?

I'm like, baby, I, I can't.

Right.

Like the There is and, and
'cause we have an HR department.

Oh yeah.

Like, it just, it would
be, it would be wonderful.

Right.

Yeah.

And not that I'm holding
so many things back or I'm

so pent up course, but like
there's a level of diplomacy

that comes with this job.

Yes.

That if you don't
understand, and Ryan,

we see a lot of people.

Don't understand that level
of diplomacy, and especially,

and I gotta say this, I think
generationally, folks that have

come up through social media
where it's all about expressing

yourself all the time.

Yeah.

And then they get
into the work world.

How about this?

When people get into the
work world and they don't

realize their employers
are gonna Google them.

Right.

As the first thing that they do.

And see all of the dumb shit
that they've been posting for

their entire lives and like
doesn't even occur to them that

you weren't supposed to do that.

I was living my authentic self.

Yeah.

Well now your authentic
self isn't very employable.

Yeah.

I think we have to recognize
that authenticity's a tool

shouldn't be a a, a reflex and
that look like we're not asking

anybody to hide themselves.

But you should edit
a little bit, right?

Like, like most of my
best work, it requires

a little editing, right?

You gotta edit a

little.

So, you know, I always, I was
say to my wife, I was like,

yes, there's things that I
feel right, but I don't get to

express them because there's
a consequence to it, right?

Like, yes, theoretically, any of
us, you know, you, me and any,

our leadership team should be
able to say whatever they want.

Yep.

But

you can't.

Right, right.

And that's the part that
I think it takes people

a minute to understand.

Is that what you say

has so much consequence?

Stick on that for a second
because I think that's an

important piece of this,
which is you and I are

always talking from the
founder perspective, right?

So Right.

In this case, your title
amplifies your, your tone.

Even a whisper from us can sound
like a verdict to the team.

And, and so I think it's
super, super important.

I, I couldn't important that we,
we hammer this point home, uh,

with, with what's the biggest
hammer you got in the workshop?

Will

I, A lot of them, but in early
in my career, I didn't get that.

And I was, you know, I was very
young and I would be in the

office, I would make offhanded
comments and things like that.

Sure.

And I didn't appreciate
the gravity to which

they were received.

And I remember there was at some
point, like figure, like I'm in

my like early to mid twenties at
the time and I'm like, you know,

five or six years on the job.

And I noticed that when we,
uh, go out to lunch or go out

to drinks, and mind you, all
my coworkers were my same age.

So there's nobody above
30 years old at the time.

Right, right.

I noticed I was.

Kind of getting invited out
less and less and, and I

couldn't quite figure out why.

Yep.

And again, at the time I was
learning this all for the first

time, so I had no context.

Yeah, you were really, none
of us would known being I why

I knew this was happening,

bounce of wisdom at that age.

But what I started to realize
was no one wants to hang

out with their boss because
there's also consequence

the other direction.

When they say something
like, I hate something.

It's like, and you're sitting
right there, you have an

opportunity to be able to
say, oh, well, maybe you

shouldn't be working here.

Right, right.

You know, I mean,
something crazy like that.

Or if I say something, you
know, we're out having drinks or

whatever, we're all hanging out.

We're we're, we're being kinda
loose lipped, if you will.

And I say, man, I really,
I've really been struggling

to come to work every.

Right.

Needle off the record.

Right, right.

Like, wait, what?

Right.

The, the guy who signed
her paychecks, uh, doesn't

wanna come to work.

Okay.

Let me update my
LinkedIn profile.

This might be, I mean,

we're, we're all in agreement
then, sir, but how does this

end, right?

Yeah, exactly.

Exactly.

It's like.

But I'm sitting
there going, yeah.

But I was being
my authentic self.

Right, right.

I I, I was speaking my truth.

Yeah, you were.

That's the problem.

You were right.

I was just being myself and
it's, that's the problem's still

important to consider
all the time.

I, I never miss a
chance to quote my dad.

Right.

You know, this, that one
nugget of his that I love,

I don't know where he got it
from, but communication is the

burden of the sender, right?

Yeah.

Meaning we have to consider
how we're saying it.

Why we're saying it,
should we be saying it?

All these things
that go into it.

But we have to consider how
it's gonna be received and

we have to think through
what's the person on the side

of this gonna gonna think?

And it's funny, like, as you
were saying that about like the,

you know, the, the team dropping
things that you react to.

It took me a while, if I'm
honest, to see comments like.

TGIF in our team Slack
and be like, so great

about being Friday.

Like it we're.

We, we need more days of work,
like we're not done with shit.

Like I, I've seen what
you put out this week.

You shouldn't be
glad this Friday.

Yeah, it's Wednesday, right?

It took me a long time to
get over that and like that

was, it was my problem.

It wasn't their problem.

They were just happy it's
Friday, why wouldn't you

be happy it's Friday.

They'd worked hard all week.

Right.

They're ready for a weekend.

But that wasn't my mentality.

It wasn't the way I received it.

I'm just like, you just don't
wanna be working right now.

And people pick up on that.

You know what, whether
you verbalize it or not.

And that's, that's kind
of, you know, what this

all comes, comes back to.

I always think it in terms of,
um, honesty being a privilege.

Uh, being able to just say
exactly how you feel and not

have to be consequential in what

happens.

Hold on, stick on that for
a second because I wanna

tie this all the way back to
something else you said in

a previous episode because
I think this is sort of one

of the same, which we said,
taking risk is a luxury, right?

Being able to take risk is
a luxury to some degree,

depending on how honest you
get, you are definitely pushing

the risk factor there, right?

And so I think that those,
those two concepts do

directly tie together.

Right.

And, and I used to think
about it in terms like when

I was young and, you know,
poor, I used to think I'm not

allowed to be honest, because
if I'm being honest, there's

a consequence to that that
could actually affect me in a

very, you know, negative way.

Yeah.

And then I looked at Rich kids
and I looked how, how Effortly

effortlessly honest they could.

And I admired that because
I'm like, man, you know,

you can say some crazy shit
and the person on the other

side has to take it because
you have money to give them.

Right?

It's the equivalent of
like somebody's at a hotel.

The maer dee, or you know,
or the, the, the concierge

isn't treating them well
and they just lay into 'em.

Right?

Yeah.

Because they know they
have this power and this

lack of consequence.

And all I could think to
myself was like, I can't even

believe I'm at this hotel.

Like the idea of complaining,
it makes me think I'm

gonna get kicked out.

Right?

Yeah.

Um, just totally
different mentality.

And so when I see,
uh, young founders.

Like myself back then, go
into the, into this job,

you know, into the CEO job.

And again, you see 'em
on social media right.

Saying like, just
whatever they want.

Right?

And I'm like, dude,
like you can't do that.

Yeah.

Or saying stuff to their
staff, you know, they'll

come to me like, I'm having a
problem with my staff member.

Here's what I want
to say to 'em.

Like, whoa, you cannot say that.

Right?

Like, you'll be in a lawsuit.

Right.

Like, or worse.

Right.

I think for a lot of founders,
um, they struggle with this.

They struggle with this
idea that if I'm not saying

exactly what's in my head,
you know my truth so to

speak, that that's a problem.

And I'm saying, no,
that's a solution.

Do a lot of things.

You know,

he's a real straight shooter.

We also don't allow firearms
in here, so we're not sure

how this is gonna work out.

It's funny, but you, you
do have to pick between

being real and I think being
responsible again, because the

communication can have so many
outcomes that are unintended.

Um, most of the time I would
say, I think I, if you, if

you have something that you
honestly do need to share and

you know, it might cause harm,
but you have to, anyways.

That happens.

Right?

That happens too.

Yep.

Because I, I a hundred
percent know what you're

not, what not saying is
sweep shit under the rug.

Right.

Just, just look the other way.

Just don't say what
needs to be said.

What you're saying is.

Put a pretty heavy
filter in front of that

before you decide, right?

Because we can't just,
everything that occurs to us

fall out of our mountains.

Well, we, we can, it
tends to not happen.

We,

that's the problem.

And here's the thing, like
I don't have a great filter.

Like my, my filter over
the years, over the decades

has not been my strongest
suit, even though I'm

aware of why that filter.

I mean, we're literally
doing an episode specifically

about the filter.

And so I, I'm the last person
to say that I'm great at it,

but I'm well aware of it.

I, I'm well aware of,
you know, where and how.

That can kind of
work against you.

And again, we're going back
to all the different places

where this starts to manifest.

One of the places, uh, that
we see is, we talked about

a moment ago is, you know,
founders on social media, right?

Like, ah, you know, I,
I wanna post everything

and put everything on.

Okay?

But dude, like, you're
not just a person on

social media anymore.

You are a CEO of a company Now.

A leader at a company and
everything that you post has a

whole other consequence to it.

'cause the people that
are seeing are the people

that work with you.

They're the people that
may work with you someday.

You know, so they're
seeing what you post.

They're your customers,
they're your investors, they're

your, the media, et cetera.

You have to start thinking about
all of those different outlets.

Whereas before it was just
what your friends thought

and you know, what, what
likes and comments you got.

Yeah.

Now it's like that's the
least of your concerns.

And I think it takes people

a minute to process that.

I think that one of the
things that gets lost is that

intention is private, right?

My intent is locked
up within me, right?

You may hear 10 words
come outta my mouth.

There were probably a thousand
thoughts behind that, right?

And so there was probably
a whole lot of intention

that's not gonna get carried
in the way that I intended

it to in those 10 words.

But the thing we have
to remember is the

intention's private, but
the impact is super public.

Depending on where this gets
said, which it's becoming harder

and harder to find a corner in
which you can say things where

that it doesn't come to light.

Um, and again, not that that
founders are just out there,

you know, m fing everybody,
and, and like just having

nothing bad things to say.

But there are a lot of truths
to being a founder that can't

just be shared unvarnished.

Right.

Right.

In the same way we expect
our wine to be aged and

our vodka to be distilled.

We like our

communication to come
through that way too.

Well, so, so, uh, play on that.

Now when I'm communicating
within the company, right,

again, I'm thinking, uh,
everybody needs to be, be honest

and transparent, et cetera.

And I understand what
those words mean, and

I understand what, what
value those words have.

That doesn't mean
they're right, right?

Yes, transparency sounds
great, but there is a time

and a place for transparency.

Okay?

Sure.

It's the way I think
about being a parent.

Yep.

Kid comes to me and
says, Hey, do you think

I could be president?

You, you have two
different answers, right?

One is honesty and transparency,
and one is filtered.

Okay?

The honesty and transparency
is there's a 99.999% chance

that will never happen, right?

So yes, give it up right now.

That's honest,
like statistically.

It's only happened to,
is it 47 people in the

history of America?

Right?

And so it, it's statistically
it ain't gonna happen, right?

So you could say that and you
could dim the spirits of this

child and in all these things.

Or you could just filter and
say, that's a hard job to get.

In order to do it, you're
gonna have to work really

hard and actually have
a positive outcome.

Now, the cynical person
could say, well, you're not

being honest with that child.

Yeah, you're right.

I'm not being right straight up.

I'm not, but if I am,
the consequence of that

is negative, right.

I'm, I'm, I buy nothing
and it costs a lot.

And I think that's the,
the filter that folks

need to start to apply.

Absolutely.

Yeah.

I, I think that we have to
go back to that, you know,

the fact there's a, the very
different power dynamic when

we're talking founder to like
rest of the team, founder to

clients, founder to market.

There's always an
imbalance there and, yep.

And so founder words are heavy.

Your employees
can't unhear them.

Your, your investors can't
unhear them and they won't.

And so, you know where we
might have meant empathy?

Employees heard
evaluation, right?

The, you know, you look,
you look a little tired.

LANs is, you look
replaceable, right?

So we have to remind
ourselves that we can't

just export raw emotion.

We have to expert
consider direction.

Intention and man,
the, the startup world

does punish venting.

Right?

It yeah.

Rewards composed clarity.

Right.

It does like, right.

We like honesty again, clarity.

That is a great way to put

it.

Yeah.

Package that shit a little

bit

before you throw it at us.

If I could Marty McFly back
to my 1990 self and, you

know, go back to that version
of that CEO and kind of,

you know, uh, try to, uh,
convince him differently.

Yeah.

Here's what I would've said.

I would've said, how
you're acting is fine.

When you're not at work, right.

Be a, an idiot, 27-year-old
doing idiot things.

Yeah.

Not at work.

When, when you leave
the office, right.

And, and you're in your
own private domain, be the

idiot that you want to be.

Yeah.

Right.

And you, you've earned that.

But the moment you walk
through this door, you have

to be a different person.

Right.

Uh, because that person,
while you know you wanna

make jokes and you want
to engage with everybody,

you wanna be everybody's
friend, is absolutely

inappropriate in this office.

And so what's interesting is I
don't think, at the time, again,

I didn't have the maturity yet.

I didn't understand that
two people could exist.

And it felt inauthentic,
if I'm being honest.

But now when I look back and
I look at a lot of the people

that I've worked with over
the years that were older and

certainly more mature than me,
that's exactly what they did.

And they did it to great effect.

Yeah.

They, they, they, they,
they put on their, um,

their work uniform, so to
speak, and did work stuff.

And then when they were
done, they took it off

and did whatever the
hell they do otherwise.

I wish I understood
that better back then.

Yeah.

And it's funny to me that like.

We do have a hard time seeing
that, especially in the

beginning because it becomes so
apparent in other parts of life.

Like the way I act with my
spouse is very different than

the way I act with my kids,
than the way I act with my

soccer teammates than the way I
act with my my parents, right?

And so like we have these
different versions of our

persona that we utilize
on a regular basis.

I think that we need to
recognize more that like

the one that probably needs
the most cultivation one

that's gonna come to us least
naturally because we're not

gonna have had other examples
of it just floating around

us for our entire lives.

Um, and that maybe we don't
have the same feedback

loops and mechanisms is
that as a founder right?

To we have to be careful and
it's, it's not inauthentic

to act differently at work.

That's what we used to call.

Being professional.

Right.

Which I know,

I was gonna say the
same thing going out the

window, probably in an office
that nobody goes to anymore.

That window might even be
there anymore for all I know.

But, but isn't it amazing
though that like, um, it it,

we've gotten to a point where
it doesn't even occur to us

that, that we may need another
version of ourselves, right?

Yeah.

Again, we, we've, we've pounded
this narrative into ourselves

so heavily that I have to be
true and authentic, et cetera.

With that, with that narrative,
we've lost the concept that

there is a consequence to that.

Like, that's not free.

You don't get just to say
whatever you want and have no

consequence or worse get angry.

Yeah.

When someone, you know, when
things don't go your way

because you were being honest,
your coworker comes to you or

something that your employee,
let's say, comes to you and

said, I'm really struggling
with how things are going.

I'm really unhappy with,
with my role, you know,

whatever their concern is.

Okay.

And you've got a couple
different ways you

can go with it, right?

One is you can say, you know,
honestly, you should probably

be looking for another job.

You could just be dead honest
and, and I'm sure there's

folks that would do that and,
and I bet the folks that are

doing that go home and tell
their spouse that's exactly

what they needed to hear.

Probably not by the way.

You know, I think that's one
of the, I think that's one

of the easy traps too, which
is that there's this sense

that by saying that, like,
oh, I got that off my chest.

Right.

I handled that as
cleanly as I could have.

Yep.

For you.

However, person on the other
side, it's, I think we, we

always have to be careful and
this maybe this is simple and

easy litmus test as you're
thinking about how it's gonna

be received, if your honesty
is gonna make you feel lighter.

Your team, your investors,
whoever, whoever the,

the recipient's gonna be.

Feel heavier.

It's probably not
great leadership.

Probably not what was needed at

the

moment.

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.

Brian, I don't think a lot of
people, just as humans really

understand that balance or,
or that transaction, right?

So, for example, I
see a lot of this.

I see, well, I said what was
honest, I said how I felt,

but they responded poorly.

And I'm like, well,
hold on a second.

Um, you're pretending as
if your honesty was gonna

have no impact, right?

To your point, it
made you feel better.

It made you feel better,
but you're pretending

like that there was
gonna be no consequence

to what you just said.

Yeah, and I see
this all the time.

I see this like in, you know,
marriages and stuff where,

where I, I see people going
back and forth and they're

like, well, you know, he
or she doesn't understand,

doesn't understand me.

I was like, it's because
you haven't listened

to them whatsoever.

Or you've just been shitty.

And, and I always think about,
and I ask people, I say, if

you were them, how would you
be processing that situation?

Time and time again, they're
like, I have no idea.

Yeah.

I'm like, I like boom.

Probably you exercise zero.

Empathy.

I'm the opposite.

Like, I process every
situation by how the

other person processes it.

Like that's, that is my
first instinct on everything.

And, and that's not always the
right way to approach either.

My, my wife will tell me, I'll,
I'll come home and she's like.

You should have said
something different.

Right?

I was like, ah, I would, I'd
hurt their feelings or whatever.

And she's like, yeah, but you
didn't get your point across.

I'm like, yeah, that's fair.

Yeah.

But again, that's, that's
the, I think we've gotten so

used to self-edit editing.

Mm-hmm.

Um, again, it's that, that
96% of the time, or 94% of

the time where, you know,
we are, we are not saying

exactly what's on our mind,
and we are, we're constantly

considering the audience, and
we've talked about this in

a number of different ways,
but I, I keep seeing it come

back to the forefront, which
is that, especially early on.

Founders are constantly in
pitch mode that it's easy

to lose sight of the, the
fact that we are kind of

constantly editing, constantly
worrying about the reactions

to things, and it can go, it
can go way too far, right?

Like if you, if you're a hundred
percent edited all the time,

probably an ingredient we forgot
to list into our recipe for

epic burnout a couple weeks ago.

But it's definitely, yeah, it
can go the other direction too.

For a lot of people, it's hard
to express how they feel or, or

you know, they don't have the
confidence to express, like I

have the confidence to express
it, but I also have the filter

to be able to say, what is
the cost of that expression?

Yeah,

right.

Somebody's behind on a deadline,
I'm just making some up.

Somebody's behind on a deadline
and I just run the calculus.

I say, is my reaction
proportionate to how this

will affect the outcome?

Right.

In other words, if I blow
up, but we've already

missed the deadline, what
am I really achieving?

Yeah.

What's happening, right?

Yeah.

Yeah.

Like,

I'll feel better, but like,
I haven't fixed the problem.

And a lot of people don't
have, don't even have

that, that calculus.

Right?

They're just like,
I'll feel better.

That's, that's,

that's it.

Yeah.

So I think that's,
that's important.

Right?

I think if we, if we zoom
out a little bit, what, what

you just said, if I pair it
back to you, it's something

like, these are kinda like
the, the filter checks a

against the 6% time, right?

Should I be honest?

It would be something like
what are the stakes, right?

Is this a values or a
character moment, right?

Is there enough on the
line that honesty really,

really matters here, right?

Who's the audience?

Can they carry the
weight of the honesty?

'cause we have to
consider that too.

And then finally,
the outcome, right?

And will, we'll, saying
this with honesty to this

particular audience actually
have a measurable positive

impact or will blowing up just
dishearten them even more.

Knowing that we still
have to go fix whatever

we screwed up, right?

Right.

We missed the deadline.

Now I'm gonna completely
demotivate my team by,

by harping about it and
the deadline's gonna

stretch even further.

Right?

So I think this is one of
those things where like having

a little bit of a framework,
even just a quick mental model

where you can jump through
that and say like, is it time?

Is this, is this a 6% moment?

And the answer's
94% of the time?

No.

But I think you do need
some way of measuring it.

I think you'll appreciate
this as a child of the

eighties, every single
time this moment comes up.

I revert back to Arnold
Schwartzenegger in Terminator.

There's this scene where
he, I, you know, you

know what it is, right?

And, and people are listening.

They, they've gotta
know what this is.

Uh, yep.

Where Schwartzenegger, the
Terminator is sitting like

in this derelict department
and like, you know, the, the

landlord knocks on the door and
he's like, are you coming home?

And the one of the best
movie moments, he turns his

head and they cut to what
the Terminator is seeing.

Right?

Yes.

So they cut the terminator,
it's like a terminal

view, and it shows like
six possible responses.

Uhhuh, right?

And it's like, yes, no,
please come back later.

And then the bottom one
is, fuck you, asshole.

Right?

He just cursors
down to that one.

Right.

And goes with that.

Yeah.

And I always think
about that moment.

Yeah.

When this kind of situation
comes and like all of a sudden

my terminal pops up and I
have five possible responses.

Right.

I never get to choose.

Fuck you asshole, by the way.

Yeah.

Look, I think when you're
Arnold Schwartzenegger as the

Terminator, I think you probably
shift to at least like a 64.

You can be honest, pretty much
most of the time, not all the

time, but most of the time,

am I returning to an
Android from the future?

Uh, my, my decision
tree will be different.

But I always think about
that moment, whereas like,

okay, all of these choose
your own adventure answers

to what just happened.

All have like, you know,
consequences attached to 'em.

And I just basically do a
sort and I say, which one

has the, the, uh, least
likely consequence or the

most beneficial consequence?

And, and again, and by the
way, like there's, uh, actually

no, we have some folks that
are actual therapists in our

audience and they'll say,
will you do not wanna do that?

You're sacrificing a lot of
your own wellbeing, you know,

for the situation, et cetera.

Welcome to the
founder Life, baby.

Yeah.

Like, I'm kind of willing
to, but it's been interesting

because when I look back at,
you know, just a million moments

where I've had that decision
tree, I don't look back at a

moment or very rarely where
I say to myself, I wish I had

been more, more authentic.

Now when I say that,
it's because I was

probably too authentic
and it bit me in the ass.

Right.

Like in other words, like
I almost go the other.

If you have authentic on
one side where you just say

whatever the fuck you want,
you have diplomatic on the

other where you just give
like the most party line

answer you possibly could.

Yeah.

I wish in more of those
occasions I had gone more

diplomatic than authentic,
even with that filter, because

again, my default is kind of
to say what's on my mind, you.

Uh, lived with me
for a long time.

Yes.

You know, that, and, and I kind
of wish I'd gone the other way.

And over time I'm starting
to try to like push my,

my dial toward that more
diplomatic side and just be

like, look what I have to say.

Uh, what, what authentic
response I have probably

isn't the right response.

And frankly, no one
wants to hear it.

That's the thing, man.

You start to realize like my,

my inside voice, my inner
voice needs an NDA, right?

Like, it, it, it has to
have some filtration.

It's funny, man, I
get, I get the comment.

I'm sure you get this too,
because we, we do deliver a

lot of hard truths to founders.

Yeah, we do.

And once a week-ish, I
hear somebody say, you

know what I like about you?

Just give it to me straight.

There's no filter,
there's no bullshit.

And inside I'm thinking,
oh, if only you knew, right?

If you turn that filter
off, you, you would hang

up the phone immediately.

Give an unvarnished version
of my opinion there.

I, I definitely
dialed it up a bit.

I put a little grit in the
sand, uh, or a little grit,

more grit on the sandpaper.

But like, that was not as
rough as that could have been.

But because people
don't want it, right?

Yes, they want honest feedback,
but they don't wanna be

punched in the face with it.

They don't wanna be made to
feel badly because of it.

Um, you know, I think somebody
said something along the

lines of once it was draft
in rage, ship in revision.

Right.

Which I thought was hysterical.

Right.

And, and, and it's, it's
perfect for me because

I do have a temper.

Right?

I do, I do emotionally
react to stuff.

Right.

It part of what I like about
me in a lot of ways, like

I'm, because it's, I react.

Emotionally happy as well.

It's not always just
like I'm pissed, right?

I, I'm, I'm a very ragey bear
and so for me, I, I loved the

idea that it's like I don't have
to just shut that emotion down.

Again, I can be
that person, right?

I just can't unfiltered
share that version with the

person who's gonna receive
that communication because

it's not gonna land well.

Right?

Uh, unfiltered for coffee
time, not, not for your

corporate communications.

This happened to me yesterday
and I slipped and I said

what I actually meant.

And it was hilarious how
badly it went that I had

to recover immediately.

Wait, dude, are you
talking about when you said

nice job on that, Ryan?

I'm looking at it right now.

In the Slack channel?

Yeah, yeah, yeah.

Uh, erase.

I, I was talking to a founder
and we're reviewing a pitch

deck and they said, okay,
so current version I've got,

which they spent a lot of time
on, how would you rank it?

And I said, well, on a scale
of one to 10, I would give

it a solid negative 10.

Oh, now, now, now that's
actually how I felt.

Right?

You were like, option five.

Fuck you asshole.

Exactly.

Fuck you asshole.

Soon as I said it,
and I was kidding, but

I was honest, right?

Like I like, and I was
laughing when I said it.

And were they No silent?

Yeah.

Just went like dead silent.

They did not, I was
like, whoa, shit.

And I said, I'm kidding.

It's probably a five.

And that, that also wasn't
like, that was me recovering.

And that also wasn't the
number they were looking for

the, the, and I thought it
was like a seven or eight

and I had to spend all the
rest of the time trying to

explain why I was giving
the, the grade that it did.

But it was funny that like I
mistakenly was honest, right?

Yeah.

Like that founder, there
was nothing gained by me

saying it's a negative 10.

And, and again, I was kidding
when I said it, but it, it

was a negative 10, right?

It was a negative 10.

As in you have to rewrite
the whole goddamn thing.

Yeah.

There's a lot.

There's nothing
salvageable here.

Now, I would normally never
say that to a founder, but I'm

going back to what you said a
moment ago, which is the founder

wants me to be, you know, uh,
uh, the hard truth get, get.

They don't, no one wants that.

Right.

They wanna believe they're
getting the hard truth,

but they don't actually
want the hard truth.

It's you when you
walk into an authentic

Thai restaurant and you're
like, I like spicy food.

And they're like, do you really?

And you're like, I think I do.

You're like your version of

spicy food, right?

Yeah.

Yeah.

So net of it, uh,
I had to recover.

But again, this is, this
is something small and I, I

always say that if I had to.

Say everything that was on
my mind, I took that, you

know, five option filter off.

Yeah.

Yeah.

And I could just say exactly
how I felt about things.

I would have no friends
by the end of the week.

That's not because I'm
repressing these things, or I

have all these evil thoughts.

Yeah, yeah.

It's because there is a certain
diplomacy with delivering

any kind of message, right.

When someone says,
how do I look?

And you say, you look like hell,
you've actually looked better.

You've gained a lot
of weight, blah, blah.

Like no one wants to hear.

That is Yes, that's
absolutely true.

No one wants to hear that.

Right.

That's why I don't
comment on Facebook.

Yeah.

I mean, what they wanna
hear is that's, that's

a great shirt, right?

Yeah.

Or whatever, right?

Like no one says, how do I
look as in please berate me.

Yeah.

That's, I dunno where
that question comes from.

Anyway.

I think where, where this
gets interesting is we all

have to look inward, right?

We all have to look inward
and, and say, how much of my

authenticity is a benefit?

And I, I think what you're
gonna find, Ryan, is not that

much, I can't think of a lot of
cases where like, I wish that

person when they said something
shitty was even more shitty.

You know what I mean?

Like, I,

I don't see it.

Yeah.

I, I don't either.

Generally speaking, I think
there's a, there's another

little litmus test that I do
around, like the channel I'm

using to communicate, right?

Yeah.

Is it hot, warm, or cold?

Oh, good point.

Yeah.

So hot, like one-on-one.

We're live, we're we're sitting
in the same room or we're on

a video call or something.

This is where I can, I
can use it, you know,

some, a bit of honesty.

For, for emotion or,
or for correction.

Uh, if it's needed, if
it's a warm environment.

Right.

Like team meet.

Like our, our, our
biweekly meeting.

I think a little honesty
there for direction

and for context, right?

I think people always love a
little bit of the, you know,

when, when we're making big,
sweeping product changes and

we give a little bit of the
why behind that, it makes

people feel like, okay, there,
there's some reason for this.

Like there's a little bit of
more and more audience, right?

Yeah, yeah, yeah.

And then if it's cold
like Slack or email.

There's gonna be very little
of that honesty because Yep.

Without the context, without
that ability to kind of see

what's behind, like short of,
you know, stacking up some

emojis so that people can
be very clear exactly what

I'm trying to convey there.

That can just be
so misconstrued.

And so I think that
for me, I'm always.

Really thinking about like,
based on the medium where I'm

gonna share this information,
how open to misinterpretation?

Is it the story
you were telling?

How quickly can
I course correct?

Right.

How, how can I recover because
find if I, you know, etch

this into a plaque and then
staple it to the front of

our, our business, right?

Like our, our motto.

Yeah.

Right.

Uh, money first customers
will always be there.

Right.

That's probably not
a great thing because

I can't change that.

I don't get to choose
how people react to it.

Right.

But if I say something
in a meeting and I can

see someone's reaction.

And I can go, Ooh, that
didn't land quite like,

like I thought it would.

A little too honest.

We've got some
ability to to recover.

So I think that's an
important consideration too.

I think the real lesson
for a lot of folks, and I

think what you and I have
learned over time, over

decades of kind of trying
to practice this diplomacy,

is our job isn't to be the
real self, authentic self.

That's actually not our job.

No.

That may be who we wanna be
as people, but our job has a

consequence, a consequence that
we have to take very seriously.

And that consequence is what
we're managing toward when we

show up and, and we're that
that person that is the CEO, the

founder, the leader or whatever
that person has to have.

Consequence in mind.

And, and with that outcome
in mind, every single thing

out of your mouth should be
what will maximize outcome?

What will maximize outcome?

My authenticity, my true self
comes second to consequence,

comes second to outcome.

And at which point you realize
that outcome is actually what,

what you're moving toward,
then that real self probably

applies 6% of the time.

And that's just fine so long
as the outcome is there.

Who you are matches perfectly.

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.