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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 another episode
of the Startup Therapy podcast.
This is Ryan Rutan, joined
as always by my friend, the
founder and CEO of Startups.com.
Will, I've got friends that
I'm gonna have dinner with
tonight, and I'm wondering which
version of me should show up.
Do they want the version
that's stressed out and
hasn't slept in a week?
Probably not.
Do they want the version
that makes the startup
sound like it's crushing it?
The one that's, let's say,
generous with the truth?
Maybe I bring the version
that pretends the startup
isn't even important to me,
and I'm just above it, and
I'll be all nonchalant, just
out here living my best life.
Or maybe I'll just pour an
extra large vodka gimlet and
see which one of them shows up,
right?
If you're a founder, that
probably just described your
entire week, because every
founder is running some version
of a casting call before
every single conversation.
Spouse, kids, investors,
customers, the team- Yeah
the friends at dinner.
They all want a different
version of you, and you're
standing backstage in
your own life deciding
which ones we send out.
So today, Will, why don't
we talk about the faces we
wear, why the job basically
requires us to be actors,
and the strangest question
the founder usually has to
ask, which is, after all the
performances, how do I even
know which face is mine?
And Will, I feel like given
that you were a theater major
before startups found you,
this might be y- you found
the one career that actually
has more roles than theater.
So- Yeah.
… let's peel the mask off,
at least for the next 40
minutes, and beat this shit up.
It's interesting to me because,
you know, for years and
years and years, Ryan, you
know, we've hosted all these
founder groups over the years.
Yeah.
And, and a lot of the founder
group members, throughout
decades, basically, a
lot of them actually, uh,
still listen to the show.
And one of the things that
I think we've talked about
both implicitly but not
explicitly is tonight at dinner-
Yeah
…
which version of
you did you bring?
And I've seen over the years
where I can tell people are
bringing different versions
of them based on- Sure
how things are
going at the time.
Sure.
Right?
You know, if things are
going really well, it's
the rah-rah version.
If things are going really
poorly, it's usually some
version of, "Please don't, don't
ask me," or- Yeah … "Don't,
don't you get?" Right?
Or, you know, "Let me tell
you my tales of woe." And I
think what's fascinating about
being a founder is that most
people can just be who they
are throughout their entire
day, and it just kinda works.
But with founders, a big part
of our existence is a persona
that doesn't exist yet, because
we're building something
that doesn't exist yet.
Yeah.
And so we're kind of
constantly defending what
this thing's supposed
to be versus what it is.
Yeah.
And our person becomes a
big part of that story.
And so we're forced to
kinda, like, be full of
shit, among other things.
Yeah.
Right?
Way more than we realize.
Way more than we realize, yeah.
And, and look, I think it's
not lying exactly, right?
Yes, sometimes there's a
little bit of stretching
the truth and whatnot, but
what we're really doing is
forecasting with confidence
that we don't have because
the honest version, "I don't
know," doesn't fund payroll.
Right?
The investor asks if it'll
be big, and you say yes.
Right.
Right?
As you
should.
You don't know, but you have
to believe that it will be, and
you have to say that you believe
that it will be, because that's
how the deal gets done, right?
That is the dance.
Right.
Right.
And so in the early days,
this is also why I think it's
fascinating that a lot of people
when they first get into this
business of starting companies,
they don't quite appreciate
how different they have to be.
I told you this story a couple
times before, but, you know,
one of our coworkers, uh, Mr.
Purple Shirt, when we went into
one of our first pitch meetings,
we were both in college still,
and we were pitching a website,
and the client who we were
pitching to was like, "Do
you guys have the ability to
do this?" And I think it was
like an e-commerce function.
Yeah.
And, and almost like on
cue at the same time, I was
like- Yeah … "Absolutely."
And he's like, "No."
No.
Like, at the same time.
And I, I just, I remember I gave
him this look like, "You son of
a bitch." And we danced around
it, and we made it work, right?
But after we get out of
the meeting and he comes
up to me, he's like,
"Why did you say that?"
Yeah.
Like, "We've never done that."
Because we have to.
Yeah.
I was like, "Buddy, how do
you think we're going to
ever do anything we haven't
done unless we do it for the
first time, right?" Yeah.
I was like, "Dude, we'll just
go figure it out." And we did.
Yeah.
I mean, like, honestly, it
was not complicated, right?
But what was beautiful was that
was his first experience of
what it meant to put on a face,
where there was a consequence
to not saying what you know
could otherwise not be true.
Yeah.
And again, this isn't
all about truth.
It has more to do with trying
to figure out what you're
allowed to share, right?
Sure.
So another version is, you
know, we go home at the end
of the day to our spouse.
Yeah.
And our spouse says, "Hey, how'd
work go?" Now, do you remember
that scene in Terminator,
like the original Terminator,
where guy knocks on Arnold
Schwarzenegger's door, right?
And, right, right, and the
display comes up, and it-
Yeah … it says like, like
here are all the different
responses he can give.
Uh-huh.
Right?
And the last one is, "Fuck
you, asshole," right?
Yeah.
So I always think about,
like, you know, when asked
the question, "How did your
day go?" It's almost like I've
got my, like, Terminator- Yeah
r- responses here.
Your
Pip-Boy pops up- Yeah … and
you're like, "What will
I choose here?" Yeah.
And it's like, okay.
And then almost as if each
of those… And I wonder
if this is a guy thing.
I don't know.
I wonder if each of those, I
then map consequence next to it.
Oh, 100%.
I was gonna say, 'cause
it's, it's not even just
about choosing the honesty.
It's then associating
the cost with it, right?
Mm-hmm.
Because sometimes… A-
and it look, it depends.
It depends on exactly what we're
masking or what we're diluting.
Sometimes the cost of
the thing is ours, right?
So the, you know, the, the
less I share, maybe the
more cost I carry, and,
like, it would feel- Right
good to let go of
that a little bit.
But you have to really be, be
careful there because, and, and
you know, I've talked to you
this before, when… The, the
minute you start to share this,
it becomes somebody else's cost.
Yeah.
Yeah,
yeah.
And it doesn't necessarily
reduce your burden by the
amount it increases theirs.
I'll give an example.
As parents, we do this-
Yeah … all the time, right?
All the time.
Like kid says to us, "Hey,
I wanna become this," right?
You know, like, "You can be
anything you want." Now, on
the one hand- Yeah … we
don't wanna, like, flat
out lie to them, right?
Right.
But on the other hand,
you also don't want
to, like, terrify them.
Again, this is, you know,
kind of personal to you, but
I remember like last year your
daughter was sick, I guess
it's been longer than that,
and it was terrifying, right?
It was absolutely
terrifying, yeah.
And, you know- And what
were your options at the time?
Right, with, with your
option, which she's asking,
"Am I gonna be okay?"
There's only one answer.
Right.
"Yes, you're gonna be okay.
We're gonna do everything we
need to make sure that you're
absolutely okay." And then
you've got the version of the
communication that's happening
between you and your spouse,
which is, is a different
level, where, you know, you're
sharing more of that concern
and you're trying to shoulder
equal parts of that load.
And then in this case, I
remember there was a point
where I was home with
the, the two youngers.
My wife was in the hospital
with Hannah, the eldest, and
it was not good at that point.
Right.
And I had been conscious for
a while, and the two little
ones see that I'm messaging
back and forth on WhatsApp
with my wife, and they're
like, "Oh, how is Hannah?"
Right?
And clearly I don't turn
around and go, "Well, she's
been unconscious for the last
eight hours, but we're still
hoping for the best," right?
Right.
So you just turn around and
go, "You know, she's doing
as good as she can right
now, and, you know, like
as soon as she's ready to
jump on a call, I'll let you
talk to her first," right?
Yeah.
That's what you say- Yep … in
that moment because what
else are you gonna do?
Yep.
Right?
So you absorb all of the
cost in that case, and
it's not a self-serving.
I wasn't lying because it
was easier or better for me.
I'm lying to protect their
fragile little emotional states.
Yeah.
There's a part of this
that really maps back
to consequence, right?
Yeah.
Like when asked a question,
we have a very deliberate
consequence that a lot of
people don't always have.
But with founders, because so
many aspects of what we do,
there are so many groups, right?
Let me give you an example.
Somebody that works at a big
insurance company and has a boss
who's kind of a jerk, right?
And the boss is grilling
them about where they were
or something like that.
If they give the wrong
answer, there's a consequence.
Boss could react negatively.
Yeah.
But that's generally
where that, it ends.
So long as boss is happy,
there are no consequences
related to work, right?
Yeah.
We have investors, customers,
employees, the general public,
kind of being like, you know,
media, social media, et cetera.
Yeah.
We have an awful lot of
buckets of consequence, and
then by the way, the one that
we go home to as well, right?
Right.
We then have this other level
of consequence, which is
very common among founders,
which are colleagues, right?
Yeah, yeah.
Like, I have lots of other
founders that are doing
really dynamic, interesting
things, and I wanna keep up
with those Joneses, right?
Right.
You mi- you know, I wanna be
able to not be the, the one
loser who isn't raising money.
Oh, yeah.
You know, whatever.
Oh, we
see this, I-
You know, whatever, whatever
your metric is … it's one of
the hardest things to manage
in those founder groups, right?
Correct.
Right.
It's like, if everybody else
is high-fiving like crazy,
and you've got one who's
just absolutely suffering,
maybe a wind-down, maybe
lost a co-founder, something.
Yeah.
Right?
It's hard to manage that.
It's hard not to feel awful
as that founder, and then it's
hard to not have that take
some of the, the, the sunshine
out of your parade as one of
the ones who's doing well.
Or inversely, everybody
else is really suffering,
and you got one founder
who's, you know, really
doing well in that moment.
Doesn't feel awesome
to share that, right?
It does not.
So how many times have we seen
founders downplay what's really
something amazing because they
don't want to kind of upset
the rest of the room with that?
Consequence.
Right?
Now-
Yep
…
some of that is just
human nature, right?
Sure.
You know, somebody just had
a death in the family, you're
not gonna talk about how- Yeah
you know, great your- Empathy
… your bachelor party was, right?
But-
Unless they happen to have
died at your bachelor party,
then it's probably relevant.
That's dark.
So but I think what ends
up happening is, like, I
just named all of these
buckets or categories
of consequences, right?
Yeah.
And all these audiences
of consequence.
And then within each of
those audiences, there
are many people, right?
Yeah, yeah.
There are many different
levels of investors.
There are different d-
Right … different levels
of customers, different
levels of staff, right?
Yep.
And all of those people require
a certain face, a certain-
Yeah … narrative, a certain
consequence that's part of that.
Let's say you've got
a co-founder, right?
And you're like, "Man,
I don't know if I can do
this anymore. I, I'm really
thinking about going back
to my, my old job," right?
Yeah.
Like, you can't say that.
Some of your audience is
gonna say, "Well, you have
to say that. That's just the
honest thing to say." Yeah.
You can say it, right?
You can, yeah.
Good luck with that
outcome, right?
It's, you go home to your spouse
and you're like, "We're screwed.
I got no idea how this thing's
gonna work," which is, like,
the default nature of a startup.
Yeah, I would say that should
be what you say every day.
If you wanna go with the
full honesty plan, you
can just write that down
and repeat it every night.
Yeah, dude, that sounds awesome.
That's really what- Yeah … I
wanna do is go home and
terrify my wife, right?
Uh-huh.
Like, that.
And again, it's not 'cause
I wanna be dishonest, it's
because I don't wanna create
a situation that's even worse.
When I go to my investors and
they're like, you know, "How's
this next fundraise looking?"
I'm like, "Pfft, I'm not getting
a single call back. Nobody
is talking to me," right?
Ha, ha.
Like, what version of that
answer is gonna come back and
help you actually get a, a, a
round- Right … raised, right?
Not, not that one.
And so we keep coming back to,
yeah, there is the straight
up honest answer, and it's
often the wrong answer.
Which means- Yeah … the right
answer requires this face,
this persona, this narrative.
Yeah.
Something we have to
conjure in order to get
to the right answer.
We're not saying it because
we're Bernie Madoff-ing
the situation, right?
Correct.
We're saying it because
we're trying to get
to a positive outcome.
We're, and we're providing the
best version of the honesty
that we can for that pers-
Founders are basically walking
mass personalization engines.
Yep.
Right?
Yeah, yeah, yeah.
We're just constantly
considering the audience and
dealing the, the, the, the
truth that's, that's most
relevant and, and most palatable
for them at any given time.
So building that.
But we are born of this by
nature of it being a startup.
By nature- Yeah,
yeah … of being a startup.
Like, we are taking something
that's never existed
before- Right … and
turning it into the world.
Like, we are quite
literally delusional.
In that path, and it's
fiction in that path
because it does not exist.
There's nothing that we can
say with ground truth that says
this is clearly going to happen.
Yeah, it's pure
uncertainty, right?
And so the- It is … the only
truly honest answer is always
going to be, 'I don't know,'
which isn't a helpful answer.
Right.
I remember we talked about
this a few weeks ago when Elon
Musk was giving his SpaceX
NASDAQ's IPO speech, and he
was like, "You know, when, when
I started this thing, I told
people there's a 10% chance
that it's gonna be successful."
He's like- Yeah … "But to
be honest, if it is the value
and outcome of that 10% of the
success- is probably worth it.
He's like- Right … but
that doesn't mean it's more
likely to be an outcome.
Right.
Now, I'll point out, he was
already rich when he said that,
so it wasn't like if someone
told him to go F himself that
he was gonna be totally screwed.
Yeah.
And who knows at the time
how much of that honesty
really came out, like if it
was that one conversation he
had with Peter Thiel or if
it was like something he'd-
Uh … he said to everybody.
But it doesn't matter.
The point is he had less
consequence in that statement
than maybe somebody else would.
But if you or I go out there and
we're trying to raise something,
money for something, and
they're like, "Hey, you know,
what's the probability of this
succeeding?" We're like, "10%."
Uh-huh.
No one will give us a check.
Yeah.
Like, there's no version where-
Like … and we got, you know,
hundreds of millions of dollars.
So we don't have
that luxury, man.
Like, we don't have the
luxury of just saying
like, "This is exactly, you
know, where things are at."
Yeah.
Because if we do, w- we'll
never get to that point, which
is, it kinda messes with you.
It does.
It's a job that constantly
requires you to put your own
needs second, not because
we're saints, we're not, but
because our real needs are
literally incompatible with
the role in that moment.
Right.
Right?
We don't get to sit in
the corner and cry because
the round fell through.
Right.
We have to wipe our face
and go get the check
from the next person.
Yep.
The grief and the fundraise
can't happen at the same
time, and the fundraise
wins because the fundraise
is what keeps everybody
employed, not the grief.
Exactly.
For a lot of people, this
isn't very compatible with
who they are as humans, right?
I've seen this breakdown
in many, many cases where
they're like, "I just,
I don't believe this is
going to work, so I cannot-
Right … tell someone else
that it's going to work." Right.
I get it, and that
sounds wonderful.
This ain't the job
for you, right?
Yeah.
Just straight up, right?
It just, it's not.
Right.
If it were, frankly,
that would be awesome.
It'd be a better, easier thing
to do for everybody, right?
Like, I would love, maybe, I
would love to be able to go
around all day long and say
exactly what's on my mind.
I would have zero friends.
I would have zero customers.
I would have zero investors.
Because none of
it's positive and-
You'd be sharing the truth with
an empty room at that point.
Yeah, yeah, yeah, exactly.
And, and when I say none of it's
positive, not 'cause I've got
all these angry things to say.
Not
like that.
Yeah,
yeah.
'Cause the reality, the, the
ground truth isn't that great.
Right.
It's, like, when you
see a friend you haven't
seen in a while, right?
And you look at them and
you're like, "Damn, they
look terrible," right?
Yeah.
You could say that.
You could, and you would be-
You
could … perfectly
honest, right?
Yep.
But you probably shouldn't
because- Yeah … it doesn't
really buy you anything.
Been a while since
you've updated your
Facebook photo, huh?
Yeah.
Am
I getting catfished by a friend?
Like, some people look at it
as common sense, but founders
is, is not really common sense.
It's like, like
fundamental strategy.
Like, again-
Yeah
…
this is the job.
You have to be okay with
being a different version
who goes into battle with the
version who could otherwise
be the terrified soldier.
Yeah.
We talked about this in
another podcast where we, we
talked literally just about,
like, our ability to just be
honest at any given time, and
it's not that we're choosing
to be dishonest, it's that
you can cross that line.
You can start being dishonest.
That does happen, right?
Yeah, that's
different.
That's a
problem.
Yeah.
But you have to believe.
You have to say things that
aren't yet true that you
have to believe are true.
Yep.
I remember realizing at one
point that was the role at some
stage at the, with the early,
not the early, kind of the mid
stage of, of my agency when
my job was to stand between,
like, sales and then design and
development teams, and it, and I
realized, like, it is literally
sales' job to go and not lie
exactly, but kind of to lie,
and then it is development's
job to make it true.
Yeah.
Right?
Yep.
Right?
You have to say that we
can do something we can't.
Back to your, you know,
the anecdote that you gave
about walking in there and
saying like, "Can you do
this?" And you're like, "Yes
and no" at the same time.
No, you have to be able to say
yes, but you have to believe
that the thing can happen.
You can't say yes
knowing that it can't.
Right.
That's bad.
Right.
That's very bad.
Okay, so that was the difference
between any other founder and
Elizabeth Holmes at Theranos.
Exactly.
She knew.
Like, she
knew straight up that
the product didn't work.
Now, now- Correct … just,
I don't wanna defend
her, but I also wanna say
there is a very gray area-
Yes
between I don't know and
it definitely doesn't work.
Definitely doesn't work
and it never will, right?
Yeah, I was gonna say she,
she could've looked at it-
If you're sure that it never
will, then that's lying.
That's why it's, it's like what
you said, it's a gray area.
Yeah.
It's so hard to know
where that line is.
Like, maybe she believed in
her heart of hearts, "If I
can just keep kicking this
can down the road long enough,
it will eventually work."
Right.
Now, you do have to be a little
bit realistic about that,
and I think that she probably
crossed the line on that one.
And she probably didn't
do herself any favors
with just kind of how big
she took it and- Correct
how kind of far she took it.
Okay.
But again, and I've never
met her, so I don't know her.
You know, I, I don't want any
inside baseball in this, but
I'd like to believe there was a
version of her that just found
herself one day looking back,
going, "Shit, I didn't wanna
get here, but I did." Right.
And I think it's easy to
vilify people when you
just look at the entire arc
all as one action, right?
Yeah,
yeah.
Not kinda like, what were those
moments where you're like,
"Shit, I took it too far." And
I think for a lot of founders,
they tell a story, okay?
Where things went to the edge-
And then something happened,
and then it worked, right?
Yeah.
And it's a great story.
But had things gone
the other direction-
For every one of those
right?
Here's a great example,
and again, uh, this is,
this is gonna be, uh,
a little bit tenuous.
So the founder of FTX, Sam
Bankman-Fried- Yeah … I,
I, I forget his last name.
I remember when he was, like,
trying to tell his weird
version of the story, and
I didn't not believe him.
Okay?
Right.
Like, I've seen enough
founders, like, in this place.
Yeah,
yeah, yeah.
But he was basically saying,
"I was trying to make a
financial move in order to
save one company 'cause I
thought it could help another."
Like, if the bet had worked-
Right … and actually,
here's the funny thing,
I think the bet did work.
It might have
looked like genius.
No, hold on.
Yeah.
I think the bet did work.
Uh-huh.
If I recall, 'cause I, I just
looked this up and talked to
somebody about this, like, not
a month ago, and, uh, Google it
or whatever, Claude, and, and
look up whether what he did,
you know, all the investors that
lost money and all, you know,
people that… Like, whether
they actually got paid back,
and if it actually made money.
Yeah.
The trade, like,
ultimately made money.
And I think it did.
Don't quote me on it, but
I, I could've sworn it
went the other direction.
In other words, had he not
gotten caught- Right … right,
but it played out, he
would've looked like a genius.
Right.
And it would've been like,
you know, a made for TV
movie, you know- Yeah
made about what a genius-
It's that- … move that was
…
don't question my methods,
just my results, right?
Yeah, right.
And, and so, yeah.
And I, I say all this to
say we have to make a lot of
optimistic decisions, ideally
for the right reasons, right?
Again, you know, different
than defrauding people.
Like, that's when you know
they're going to be hurt,
but you still do it anyway.
Like, you know- Right
… they're going to be hurt,
not they might be hurt.
They will be hurt, right?
Like, that's different.
But I look at it and I'm
like, that's a gray area, man.
Here's a good example.
If I can't pay for my kids'
education, I, I take what little
I have of their savings and
I go to Vegas and I bet it.
If it works, I'm a
genius, but if it doesn't-
Yeah … I'm the hor- most
horrible person ever, right?
Or I bet on a
stock, uh, whatever.
Then you just start debating the
value of a college education.
It's okay.
University of Phoenix, uh, kids.
So the way I look at it though
is we're constantly put in this
pressure cooker where we have
to determine which version of
us are we going to use, right?
Again, this is at
a lot of levels.
It's not just what do
we bring to dinner, what
do we say to our spouse.
It's how optimistic can
I persistently be- Yeah,
yeah … before I run out of
gas or even I don't believe
the, you know, the future.
Right.
That's, that's a… Every
founder gets to that point-
Yeah, exactly … some
of us never make it back.
One of the hardest parts about
this, and one of the very
brutal ironies of the entire
thing, is that, and, and I've
heard this from a bunch of
people, they're like, "Oh, you
know, founders are just these
emotionless robots," right?
They're willing to say whatever
needs to be said to get the
thing done in the moment.
Right.
Bullshit, right?
A- are there some?
Sure.
Yeah.
Just like there are some
emotionless doctors, and some
emotionless lawyers, and some
emotionless- Yeah, right, right
… bankers, and candlestick
makers, and whatever else.
Yeah, yeah.
Sure, sure.
Emotionless people.
But we feel- Some of
them happen to have
jobs … all of it, often more
than the people around us.
Yep.
It's that we don't get the
luxury of letting the real
feeling drive the words
coming out of our mouth in
real time- Yep … because
that honest, unfiltered, raw
emotion version of a founder
in a hard week, like you said,
that's the person that nobody's
going to agree to work with.
Yep.
Right?
And it's not pretty, but
that, that is the job.
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
1,000 times before you, which
means the answer already
exists, you may just not
know it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually solve
these problems all day long
at groups.startups.com.
So if any of this sounds
familiar, stop guessing
about what to do.
Let us just give you the answers
to the test and be done with it.
Again, I've seen this just
with founders in general,
you know, that, that I've
talked to o- over the years.
It's interesting because I think
they're worried that what they
say to me or, you know, in a
group, whatever, will color
what people think about them.
Well, they're right.
It absolutely will
do that, right?
Like it would be, it'd be
ridiculous to think that if you
tell everybody in a group that
your investors are assholes
and, like, you can't get- wait
to get rid of those guys, that
it may not get back to them
in some way, shape, or form
and cost you later, right?
Or if you say something like,
"I've got no gas for this
thing, like, dude, I'm, I'm,
I'm ready to, like, hang up my
spurs and be done," that there's
some chance that one of the
people in the room Their spouse
or brother-in-law actually
works for your company, right?
Right.
Like, and, and it gets
back to them and then it
goes, you know, viral in-
inside your Slack channel.
That shit happens all the time.
It
does.
And so it's really difficult
for us as founders to be able
to know what we're allowed to
say, what we shouldn't say.
And again- Right … these
shape the faces that we have.
To whom, when, in
what environment.
Yeah.
You gotta figure, like,
politicians and celebrities
deal with this for a living.
All the time.
They gotta worry about the
one person that overhears
a comment they make,
maybe even out of context.
Yeah.
Right?
Right.
Tweets that out, right?
You know.
Half of a sentence.
Yep.
Yeah.
And then all of a sudden they're
dealing with a PR nightmare.
Yeah.
You see with hot mic, you
know, things, a few times
a year someone will have a
hot mic moment where they
say something to somebody.
Trump does it, like,
every six months, right?
Yep.
And nobody cares anymore, right?
I mean, he said the craziest
shit that's been f- straight
up telegraphed to everyone.
Maybe he just says it all,
all the time now anyway
and he just, you know-
Right … it's all camouflaged.
It's,
doesn't matter.
Yeah.
But I guess what I'm saying
is, like, you get those hot
mic moments and you hear what
somebody actually has to say,
like, the God's honest truth.
Yeah.
And it, you know, goes
viral in a minute.
Right.
And you're like, "They're not
allowed to be honest?" Right?
Like, uh, they are, that's just
the consequence of being honest.
Correct.
That nobody else has.
Right.
Yeah.
And man, the emotional
overhead Of having to
manage all that is insane
Every
day Every single day.
I think it's one of those
things where, like, the emotion-
emotional labor is, is one of
those, like, invisible line
items in a startup, and the
founder pays for all of it.
We measure burn rate on cash,
but nobody measures the burn
rate on the poor founder
having to be the calmest, most
optimistic person in every room
on the worst days of their life,
and that bill comes due, right?
I never thought
about it like that.
It just comes due privately
later, and usually
all at once, right?
Like, those are the kind
where, like, that, that comes
flooding in all at once.
I think it's fascinating to me
because it always reminds me of,
like, the captain at the wheel.
Like, while everybody else
has jumped ship, kinda, like,
holding the ship together
while, like, it goes to
the bottom of the ocean.
Yeah.
There are very few people that
are built for that, right?
Yeah.
Very few people.
This is a weird commentary,
but I think the, the world's
making fewer of them, if
I'm being honest, right?
Like, anymore it's, it's
easiest to, like, call yourself
a victim and escape than
to actually- Yep … be a,
"No, this is my ship-" Yeah.
Or normalize that … "This
is my duty. This is…"
Yeah, I ride it out.
But that said, it's still
really hard for people to do,
to what you said, to shoulder
that burden, to be the most
optimistic at what's essentially
the hardest part of your life.
And even worse, here's where
I see it, when a founder
already knows it's over.
Like, in other words- Yeah
… in some cases, they've actually
already closed the doors, right?
Yep.
They've, they've already closed
the doors, and they go to that
first cocktail party or that
first catch-up with a friend,
and they don't know what to say.
Right.
Right?
Because up until yesterday
I could've said could've,
should've, would've, maybe,
but this is the first
time where it's like,
"No, we actually- Right
you know, told the
investors." Have, have to go
that other direction.
Right?
Yeah.
And it's like, "What version
am I supposed to be now?
Like, am I the person who
says, like, it's over?" Yeah.
And you watch this catharsis.
It's unbelievable to watch.
Right.
It's the same thing people
feel, though, when they just
filed for divorce, right?
Or they just lost
somebody in their lives.
So, you know, earlier this year,
I was at dinner with a founder.
He's actually, uh, one
of the listeners, so,
uh, he'll remember this.
And, you know,
you'll remember this.
Unfortunately, my, my
brother had just passed.
Yeah.
And my brother had just
passed the day before, right?
He's like, "How are
you at dinner?" Right?
Like, he's a great guy, right?
He's like, "Are you okay?"
He's like, "You're- Mm-hmm
… waiting, passed yesterday?"
And I was like- Yesterday
… "Yeah, but, you know, it's,
it's been a whole thing." I
remember at the time, I was
like, "Shit, like, am I still
playing a different version of
myself, like the version- Yeah
before this happened?"
Right? Like, I haven't, like,
adjusted. And, and what I
said to him, I was like,
"Honestly, I'm so used to this.
I'm so used- Right … to, like,
crazy shit happening and just
having to be me regardless,
it doesn't really occur to me
that I can do something else."
It's like we have simultaneous
roles on three different
networks where, like,
two of them are rom-coms.
One of them is
a- … is a drama.
Oh.
The other one is… Right?
Like, and we just have to
compartmentalize and jump in
and out of the different roles
and play them at any given
time, and it's exhausting.
It is.
And, and again, I remember at
the time thinking, "Wow, like,
what happened here?" And it
wasn't me being disingenuous.
I was very honest about
what was happening.
Yeah.
But I think you s- said this
a moment ago, I think I've
developed such an ability
to compartmentalize things.
Yep.
That even something as, as
extraordinary as that, I used
my, you know, founder method,
which is just, you know-
Yeah … you compartmentalize,
you rationalize and
all these things.
And even in that extreme, the
face paint comes on, right?
You know, like- Yeah … you're
like, "Okay, this is who I need
to be in this moment." And I use
that example, too, just from a
standpoint of that would be the
one time everyone would forgive
you, right- Yeah … for, like,
being any version that, that
you want, and it didn't occur
to me that that was the case.
I, I was back at work the
next day, if you recall.
Yeah.
Right?
And again, this is me just
saying, like, it didn't
occur to me that I could
just mourn or I could just
not work or I could just-
Right
…
whatever, right?
And I'm not saying that's good.
I, I'm saying the opposite.
I'm saying- Yeah, it's-
Like- Yeah … that's 30-plus
years of having to do that.
It adds up.
Yeah, it does.
It is one of the, the kind of
the hidden costs, and, and I
think it's one that it really…
It starts to become instinctive.
It starts to become- Which is
weird,
right?
… muscle memory.
We don't even really think about
whether I should change roles,
whether I need to change role.
Is the cost of changing
role- Worth it in this case.
Yep.
Right?
Like, because we can look
at that and say, not if
emotionally you needed
something else, because not
going to that dinner would've
cost you absolutely nothing.
And so if it would've gained
you some catharsis, some
peace, some whatever that you
might have needed that moment.
But we get so used to
being in that, that second
seat that we don't even
think about it anymore.
Yep.
Right?
We don't even think about the
fact that, like, I have a need
or I have a want, a desire,
something, and, and it's just
like, that just constantly
gets, gets put second, right?
Well- Which is why I think,
like, you and I tend to, to
overreact when we start to
hear things like how greedy
founders are, how, right,
because these are the kinds of
costs that you and I have, have
paid the bills on, and that all
founders go through this stuff.
And so when people see that
outcome, right, like you went
on a little bit of a rant a
couple weeks ago when somebody
said that, you know, Musk
didn't earn that money, right?
He earned it on the
backs of other people.
Did he, though?
Yeah.
The backs of all the people-
I'd love to be one of those
backs … he was making feel
better and lying to, and not
lying to, but basically like,
you know, helping to sugarcoat
the ugly truth until it was
a beautiful truth for them.
You know, one of the things
along those lines is how
many days, this is you and I
specifically, have we shown up
for work where we have come off
of a crippling injury, right?
You know, you and I both
have significant diagnosed
conditions that are-
Yep
…
brutally, excruciatingly
painful, right?
And how many days have we had
to come to work and pretend
like it wasn't happening?
Put on the face and go.
Right.
Yeah.
That's what I'm saying.
Yeah.
I, here's one, and I'm
sure you've heard this.
I'm sure you've heard this,
which is at some point later,
a founder will come back
to you and go, "Oh my God,
I didn't know on the day
that we talked that you were
going through," whatever.
Like, they'll have heard us
say something on the podcast,
or they'll have talked to
somebody else within the team.
Something happens and somebody
goes, "I didn't even know
that you were going through
that. Like, oh, I'm so sorry."
And I like… And it's funny
'cause I always hear that and
I go like, "Well, of course
you wouldn't have known I
was going through that. Like,
what would the benefit to you
have been in knowing that?"
Right?
Yeah, yeah, yeah.
Right.
It's like I'm not gonna wear
that on my sleeve so that it
impacts my ability to help you
in the way that you needed your
help- Exactly … simply because
I had something going on.
Now, again, that's not
necessarily a great answer, but
damn is that the stock answer.
Now that I'm thinking about
it, Ry- How many times have
we done a podcast, like if, if
we're talking in context, right?
Yeah.
Where you saw tears coming down
my eyes, like, while we were
talking because I was in such-
Not of joy … crippling pain.
Yeah.
Right?
And like, you know, so for
folks that listen, I've got this
weird condition where, like,
sometimes I have, like, a nerve
in my head, my face that fires.
So whenever I talk, which I
do all the time, when I move
my mouth, it basically is like
getting tasered in the face.
Yeah.
So imagine Ry and I on for
f- half hour, 45 minutes,
and that's happening the
entire time that I'm talking.
And I'm trying- Yeah … to
motor through it.
I'm trying to pretend
it's not happening.
But, like, Ry can see in
the… You know, 'cause
we're on, we're on Zoom.
He can see- I can see it
… tears streaming down my face.
I can see
your face.
Right?
Yeah.
And that's like-
If, if you've ever heard me
deliver what sounded like
an oddly timed and, and
stretched out monologue-
Yeah.
…
there's at least a 50%
chance it's because I'm just
looking Will in the eyes-
Yeah, yeah … and going,
"Are you back yet, buddy? Can
you move your face again?"
Yeah, yeah.
"Are we… Are you
good? Are you good?"
But again, this goes back
to it doesn't occur to me
that you don't just do that.
It's like, d- no, you just
keep fighting through it.
And I'm not saying
that's… Like, I'm not,
like, saying it's great.
I'm saying, well, it's
not, it's painful, right?
I'm saying but- I've kind of
conditioned myself to make this
normal, which kind of brings
us back to, holy fuck, right?
At some point we've conditioned
ourselves to make that normal.
Yeah.
That is so messed up, right?
Yeah.
Again, this isn't me
bragging about it.
This is me going to that
extreme- Yeah … to illustrate-
Yeah,
totally … how messed up it is.
Yeah.
The, the future here.
But also how we got here.
Like, I've been doing
this for over 30 years.
This isn't the first time
where I've had to, like,
fight through something in
order to, like, be o- be on
the right side of things.
And so I look at it and
I'm like, "Well, what
else would you do?"
Right.
A
reasonable person would
look at that and be like,
"Are you out of your mind?"
This isn't a podcast for
reasonable people, Will.
This is a podcast for founders.
For reasonable people, right?
So y- we take it back and
we're like, "Okay, well, who
do I bring to dinner?" Okay?
You know, you know- Yeah
… we've, we've talked about
who all these different, you
know, potential personalities-
Yeah … and faces are.
Right.
But is there,
like, a, an answer?
A- and it- Right
here's as close as I've gotten.
There is no answer, but the
closest I've gotten is this.
You have two scales
on w- or one scale.
W- on one end of the scale
you have y- joy, like what
would bring you joy to bring
to dinner, uh, but on the
other side you have, but what
will bring you consequence
to bring to dinner, right?
Yeah.
And the reality is for most
people, only one side of
that scale matters, right?
Yeah.
It's the consequence side.
I don't really get to just walk
in a room and say whatever-
Right … I want 'cause
I've got the consequence
of what that will bring.
Now, that said, I tend to say a
lot of what's on my mind, right?
Like, I'm not exactly quiet.
But I'm mindful in most cases of
what that consequence will be.
Yeah.
And I think for a lot
of founders, like,
that's the balance.
You know what I mean?
Yeah.
I feel like this is where it
gets, it's tough because then
the, the question is really
like, well then who am I, right?
If I actually have this
ability to, to pick and choose,
right, and I'm, I'm now many
face, like, how do I decide,
like, who I actually am?
It's not easy.
It's not.
A- and I think you find yourself
wedged between a couple of
particularly hard truths, one
of which just being that, like,
we've talked about r- that raw
honesty has real consequence.
Yep.
If somebody asks, "How
sure are you you will raise
this next round?" Right?
There's no honest way to give
total certainty because- Right
we don't have any idea.
Right.
But that person is paying
their mortgage on your answer.
Yep.
Right?
So I don't know, but
maybe we lose all our
jobs is technically-
Yeah, right … the truth.
Yeah.
And completely unusable.
Right.
Right?
So we're, we're
stuck against that.
Wall two is essentially w- that
we're literally paid as founders
to be unreasonably optimistic.
Yep.
That's the gig.
Yep.
Right?
When there are almost no signs
that it'll work, it's our job to
believe that it will, out loud-
Yep … all day in front of
everybody in your life, right?
Yep.
Professional optimism on demand
regardless of the evidence.
And then the third wall
is our own sanity, right?
Because if, if you sat still
and honestly reckoned with
how insane the situation
you put yourself in actually
is, you'd lose your mind.
So, so the delusional version
of you isn't just for the
investors, it's also for you.
Your Bible study
And it's the thing that
gets you to tomorrow.
It's a survival mechanism
wearing a smile, which then
really draws into question,
like, okay, if this is all
also for me, who, who is me?
Where am I in all this?
Yeah.
Right.
Um, and I think for a lot of
people the idea that I'm not
being true to myself, speaking
my truth, it's like you
don't really have the option.
That does sound cool, and
if you can somehow make it
through this entire gauntlet
and only give exact God-honest
truth, like, like your absolute
ground truth assessment of
everything, good luck to you.
Right.
And you know what?
I envy you at so many levels.
I'll give you an example.
My wife, who I love to
death, has only one version,
which is straight up truth.
Yeah.
She will tell you exactly
how she feels about anything-
Yeah … at any given time,
as well as other people.
But while I, I legitimately
envy that, she doesn't
have the consequence
that that comes with.
Right.
If somebody says, "Okay. Well,
I don't like you," I'm going,
"Okay. Well, you don't like
me." I'm like, move on, right?
Yeah.
If that same statement came
from me and- Every single person
that I work with or clients,
whatever, all left, I'm fucked.
Yeah.
I can't be honest like that.
Can't
do that.
And it's not because I wanna be
dishonest, it's because there's
a, a straight up consequence to
delivering the wrong narrative.
Like, here's a good example.
When I worked in the agency
business, and you worked in the
agency business as well, there's
clients I really didn't like.
Yeah, 100%.
I just really didn't like them.
Straight up, right?
Most people don't like
their boss, as an example,
right?
And, and part of my job was to
make sure they never found out.
Yeah, right, exactly.
Because if I were to say to
this client, "I'm so sick
of your shit, you know,
you're such an a-hole", cool.
Then they fire me.
Right.
But by virtue of that,
I don't get to pay other
people's mortgages.
Right.
I love your accounts
receivables, I hate your guts.
Yeah,
exactly, right?
You can't say that.
Like, and it's like, I
genuinely envy folks that
don't have that consequence.
I genuinely envy folks
that can just say,
"Here's how I feel." Yeah.
And that is the end of the line.
That's all there is.
It's a powerful and reassuring,
you know, kind of place to be,
and it generally doesn't exist
in our our workplace, however.
Right.
N-
not, not as a permanent state.
Yeah, yeah,
yeah.
Right?
Yeah.
So, so I think one of
the healthiest things the
founder c- can do, right,
because they can't stop
wearing the faces, that's,
that's just not realistic.
Yeah.
And honestly, it's, it's
not even wise, right?
As we just said, like, you,
you just really can't do that.
But I think you do need
one room, one person, one
place where you get to take
the faces off completely.
And I think that the founders
who find that, have that, are
far more likely to survive
this in, in a healthy way.
That's the founder groups.
I mean, that, that
literally is- That is so exactly
what I was getting ready to say.
Yeah.
So this is, this is why
you and I do what we do,
and this is why we open
ourselves up for these things.
So, you know, come
hang out with us.
Like, this is why we exist.
The, we are this for a,
a lot of founders, right?
And it's funny to me always
that I don't think if we
said… It's like, it's that,
the whole thing, like, as
I, my ICP, and I'm always…
I was coaching people on the,
the mom test, and don't ask
people what they would do.
Because I think if you and I
said, like, "Hey, come and join
our group, because we will give
you the opportunity to just
be, you know, uh, completely
unabashedly honest, and
you're gonna feel way better,"
nobody would pay for that.
Nobody would join to do that.
And yet, when we talk to
the founders who are in our
network and in our communities,
that's one of the things that
gets referenced all the time.
It's like, "God, it just feels
really good to just actually
be able to say what's on my
mind, and to know, one, you're
not gonna judge me, two, you've
been through it yourself,
and three, you probably have
something to say about this
that's actually going to help
bring me back from the ledge."
Right?
It's amazing.
One of the things that I
always notice, when we did,
like, what I'm gonna call,
like, bigger founder groups,
where there's, like, 20
people- Yeah … in the room.
So it was less- Yeah … of,
like, a super intimate
setting, but it was 20 people.
Yeah.
Like, a very curated
group of people.
Curated being people you
knew that were gonna be,
you know, honest, et cetera.
I always had in my mind a rough
list of what order I'd kinda
call on people to kinda share.
Uh-huh.
But the first one or
two people were always
incredibly deliberate.
And, and I would encourage
folks to understand the
dynamics that I'm, that
I'm gonna present here.
I would tell them ahead
of time, "Look, man, I'm
gonna call on you first.
I know you're gonna be honest
because you've got a certain
level of security or delivery.
That- that's incredible."
And as soon as they would set
the tone for honesty, right?
It was just, it was
almost a level of, like,
uncomfortable honesty.
And I'm gonna call- I usually
don't use names, but I'm
gonna call out two people in
specific because they deserve
it, and they're very- Yeah
public.
One is, uh, remember
Andrew Warner?
Oh, yeah.
Did Mixergy, et cetera.
I've been friends with Andrew
for decades, and one of the
things about Andrew, he-
certainly on his podcast, but
certainly when you, you meet him
in person, he is uncomfortably
honest about himself.
Yeah.
Right?
Yeah.
And it blows my mind because
he's, he's got like, he's got
this dual way of delivering that
I just, I've never seen many
people pull off, which is he's
very self-deprecating, right?
Yeah.
But it almost makes
him invincible.
Part of where self-deprecation
comes from, right?
It's like, "I'll take away your
opportunity to take shots at me
by shooting them all myself."
Right.
And again, I, I, I don't
think he's doing it in a
manipulative way at all.
I just think that's
the way Andrew's built.
Yeah, yeah.
But when he's in, you know,
we've had founder groups with
him in it, and I know that
if I call on Andrew first
and he shares, he sets the
tone for everybody's space.
Right.
Yep.
And one other one that, that you
also know is, uh, Jay Clouse.
J- Jay's been a friend.
He actually used to
work at Startups.com.
Yep.
I always forget
about that, right?
In the early days, a very
popular podcaster now.
Jay stayed at my house back in
Florida many, many moons ago-
Yeah … and spent a couple
days with us and the kids.
Yeah.
But Jay was somebody I would
call on, you know, in these
founder groups initially
as one of the first people.
And, and again, I'm, I'm gonna
give it to Jay for his bravery.
He would set the tone, man.
He'd like, "Here's exactly
where I'm at." He, you know-
Yep … he'd done this.
He's built a career on this.
I mean, that's- Yeah … he's
done so well with his podcast.
If, if you haven't seen
Jay Clouse on YouTube or
anything else like that,
like, he's the guy, right?
You know, he's the, the
content creator's creator.
And what he would do is he would
share with the group, but he
basically gave everyone in the
room permission To be honest
That's, that
sometimes all it takes
It was magical
every single time.
Yeah.
Because it was one of
the few times everyone
in the room, particularly
founders, could hear someone
else not be full of shit.
They could hear someone's
version of where they
are without a face.
Yeah, and guess what?
Sounds a lot like
their version, right?
100%.
That, that's what it was.
The actual version, the
one that they're not
allowed to say out loud.
They're like, "You just said
all the things I didn't get to
say today. I love you for that."
Well, okay, so the dynamic in
this, and this is every cocktail
party, it's not founder groups,
et cetera, is there's always
a tone or a narrative that
people instinctively match.
This is, uh, just like, like
a kind of a group theory.
If the first person up
chest pounds, right?
"Oh, things are so great,
you know, I'm, I'm killing
it," blah, blah, blah.
Yep.
It sets the tone for everybody
else in the room to follow.
Now, some people- Right
… won't because that's just
kinda how they're built
or what they have to say.
Yep.
But you can see it go-
Or
they've got nothing to
pound chest about, which
is pretty common with pound
chest … dude, I've done this
thousands of times, right?
Like- Yeah … you can almost
watch it map one-to-one with how
the tone gets set early, okay?
It also goes the other way.
If after a couple people
chest pound, the next person
comes on and says, like,
"I just had… Like, I just
lost my relationship with my
spouse, and we're shutting
the business down"- The next
person, no matter how well they
did, takes it the fuck down.
Yep.
They're like, "Okay, okay. Like
maybe this, uh, this isn't the
right time." Now, to be fair,
the first person who went-
But, but even that, just, uh,
think about that for a second.
Even that is a version of having
to put on a different face
than the one that they actually
wanted to bring together, right?
Yes, that's actually, I was
taking it the other direction.
Right.
So even in these moments
where we're being honest,
and like, and there's a good
reason for that, it came at
a cost to that founder who
was like, "Man, I was really
hoping somebody was gonna lead
off with high-fives, 'cause
I've got a big one today."
Yep.
Right?
100%, right?
And I'm always mindful
of how that trajectory
works throughout the room.
And again, y- it's not because
I want everybody to, like, like,
drown in their sorrows, right?
Good situation, bad
situation, I just want you
to be able to put the face
on a shelf for a minute-
Yeah
…
and say the stuff that you
wish you could say, good
or bad, right, in front
of a bunch of people that
actually get it, right?
Yeah.
Like, like that you actually
don't have to put on a
face, 'cause they're not
trying to do it either.
Right.
I see this consistently
with groups who understand
each other, right?
It could be people who
share the same religion.
It could be a moms group.
Yep.
It could be a veterans group.
It could be s- somebody who
has a core common interest
that the average person- Yeah
doesn't understand.
You see this in every
single support group.
Hm.
You know, people have a
certain- It's shared context.
Yeah, exactly, right?
And they can finally be like,
if you or I were in a support
group for people who have
our respective conditions-
Yeah
…
no one would feel sorry
for us, only because they
understand exactly how it feels.
And I, I don't want your
pity, I just want your
understanding, right?
And with things like- Empathy,
not sympathy.
Yeah.
Right.
Yeah.
Okay, like, like you can't
kiss your kid because you
can't move your mouth, right?
Like- Right … that happens to
me every single night, right?
Like, that is something that
someone else can ascribe to.
They can be like, "Okay,
I get it." For a case like
this where we've got founders
who, for the first time, can
be like, "This is brutal,"
and the person sitting next
to him is like, "Bro, it-
that's my Tuesday," right?
Yeah.
And so they're like, "You
too?" It's amazing to watch.
Yeah.
It feels good, and it feels good
to watch it happen, and, and
we know what that feeling is.
We've been in that chair
where all of a sudden we
had the realization that,
"Oh my God, everybody else
is going through this too."
You
bet.
It's so good to
have that moment.
Just to know that you're,
you're not alone, right?
I think founders also
get put in this position
because they're building
something entirely unique.
Yeah.
Right?
Something that's
never existed before.
So, then they assume ri-
rightfully, right, th- the thing
they're building is very unique.
Right.
The things you go through to
build that are not nearly as
unique, but I think that gets
twisted in the entire thing, and
they assume that, "Look, because
what I'm building is, nobody
else is doing exactly what I'm
doing, so nobody else feels
exactly the same way I do."
Right.
Mm, not quite.
They're not doing exactly
what you're doing, but
they feel exactly the
same way you do, right?
E- exactly.
They get high on the highs,
they get low on the lows,
and, and there's a whole
lot of beatings in between.
I think for most people, when
they're thinking about that,
you know, metaphorical dinner
that I have to go to tonight,
you know, whatever that- Yeah
that social, social
situation is.
And they're like, you know,
"Do I have to be the, the
optimistic person?" You know,
"Do I get to wear my heart
on my sleeve?" Et cetera.
Yeah.
The
truth is, in many cases, what
you're gonna bring tonight to
dinner is not of your choice.
I mean, you know, to,
to the extent that
you, you have some- No
some ch- like, part of that
has a lot to do with the,
the consequence and the
situation that you're in.
So whoever you're gonna bring,
whatever persona, whatever
mask, whatever face that you're
gonna bring, understand that's,
that's who you had to be, right?
Yeah.
That's who you have to be.
That's what this job is.
And generally, there's no other
version where you can just say,
"I'll be whatever I want, uh,
whenever I want," unless you
make a billion dollars, and
you get an Elon Musk thing.
And at that point, if
you get that far, be
whoever the hell you want.
Bring any face you want
for the rest of your life.
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
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