Startup Therapy

Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return? The episode argues that investor dilution is often the cleanest trade because cash and terms are clear, while “everyone else pays in maybes and promises.” It warns that early-stage equity feels worthless but represents 100% of a company’s future value, so giving away 50% to a near-stranger can become a permanent cap table problem that also costs speed, optionality, and sanity. Practical fixes include vesting, cliffs, tying equity to real value creation, defining what happens if someone stops contributing, and putting breakup terms in writing early. The discussion also critiques employee equity as time-based rather than performance-based, and advisor equity as often unaccountable, where tiny percentages can hide very expensive outcomes.

What to listen for:
00:00 Investor vs Founder Equity
01:26 Equity Is Priceless
03:43 Co-Founder Split Hangover
06:04 Why People Underperform
11:15 Fairness Turns To Resentment
12:44 Will's Unsubscribe Story
15:53 Vesting And Breakup Terms
18:17 Early Employees Option Pool
20:26 Equity As Compensation Trade
21:59 Paying Twice With Equity
22:14 Does Equity Change Effort
23:10 Lottery Ticket Reality
27:23 Equity Rewards Three Things
27:37 Advisor Equity Math
31:00 Reputation Versus Contribution
33:30 Network Intros Social Capital
35:56 Advice Has Shelf Life
40:24 Pricing Advisor Time
44:06 Treat Shares Like Cash

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 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 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 Schroeder.

Will, we watch founders
fight like hell over giving

an investor 15%, and then
turn around and hand a

co-founder 50 cen- or 50%
like it's a free breadstick,

or like it's 50 cents, right?

The truth is, man, investor
dilution is usually the

cleanest equity we give
away because at least we

know what we got for it.

Yep.

Why, in your opinion, are
founders so disciplined with

investor equity and so wildly
emotional with everybody else?

It blows my mind.

It blows my mind that given
how expensive these other

decisions are, how, like, just
frivolously, like, people- Yeah

give, give away their
stock to a co-founder-

Yeah … which, which, you
know, is always m- my, my gripe.

I'm not anti-co-founder, but
dude, you paid a lot for it.

Or employees, early
employees, you know, who

may or may not contribute.

Or advisors, who I think if you
did the math, are gonna wind

up being the highest priced
advice you could possibly find-

much less would pay for.

Yep.

Right?

Founders, w- when we say,
like you said, "Hey, you're

gonna give up 15% of the
company." "Oh, maybe it

could be 12," or whatever.

I'm like- Right … "You're
gonna get actual money, man."

There's an inbound wire that
justifies that decision,

right?

Yeah.

So- That one's okay


so how are you okay with giving
some guy you met on- Yeah

Craigslist 50% of the company
because- Yeah … he could

build a mobile app, right?

Right.

How are you

okay with that part?

Yeah.

Equity is not a thank
you note, right?

Yeah, yeah.

It's, it's the most expensive
currency a startup has, but we

don't treat it that way, right?

I, I'm gonna, I'm gonna echo
back to something you said,

I think on the podcast,
but it's been, like, six

or seven years ago now.

And, and you said that,
"Yes, today it feels, it

feels valueless," right?

Yeah.

The company's at, at a state
where, like, it doesn't

feel like it's worth much.

But remind yourselves that
represents 100% of the

future value of your company.

Yep.

Let me say that again- … in
case anybody choked and

spit their coffee out.

It represents 100% of the
future value of your company.

And so when you are handing
it out like, I don't know,

Halloween candy, might
wanna reconsider that.

When I look back at all
the startups that I've done

and kinda how I've, you
know, distributed equity

in the past, and I, I'm not
terribly upset about it, of

all the decisions I made.

In other words, like I, when I
looked at, at… Like, I never

looked back and say, "Oh my
God, that person got too much,"

or, "I got ripped off," or,
you know, something like that.

Yeah.

Nothing like that.

What I'm upset about is how
poorly I valued the equity.

This is me saying I think,
you know, people more or

less earned, you know, what
they earned, but I think

my, my internal compass,
where I, I wish- Yeah

that I had been more
disciplined about how I

thought about that equity.

You know, kinda, you know,
what we talk about now, which

is, oh, damn, it, it's, it's
worth real money now, right?

And I think what happens in
the early, early days- is

we're on the opposite side.

We can't believe anybody
will do anything for these

magic beans that we have
called equity, right?

We're like, "Wait,
you'll do- Yeah.

Seriously?

Yeah.

Like, you, you'll take- Yeah
… you'll take this Monopoly money?

Seriously?

Right.

Yeah.

Yeah, it'd be like, yeah,
it's, it's like walking into

a car dealer and being like,
"I just printed this out."

They're like, "No problem.

No problem.

Just go ahead.

Take anything you want off
the lot and just leave us a

stack of your fresh-printed
bills right there."

What throws us off is because
we feel like we got it for free,

'cause we just came up with this
idea nine seconds ago, that we

can just give it away for what
we perceive to be real value,

that it must be free currency.

Yeah.

And that's why in the early
days, which is why we're

doing this episode, which is
why in the early days when y-

that first year, that first
18 months, when startups

founders don't realize how
vulnerable they are, that we

start giving this away, again,
because we're so blown away.

I'm gonna go back to the
co-founder one for a second.

Sure.

The most common instance,
and we will dig into

this, but the most common
instance is I got this idea.

If anybody will agree that it's
also a good idea, vis-a-vis

validate me, and- Yeah … join
me on this insane journey so I'm

not alone- Yeah … I'll kind
of agree to just about anything.

Yeah, yeah.

Yep.

T- terms?

Yep.

terms.

We don't need a term sheet.

Here's half the company.

And I always remember, 'cause
we always saw this live at

the startup weekend events.

You know, where in one weekend
everybody came together.

Any hackathon or
anything else like that.

And it would always
be the same thing.

The weekend goes, it goes
from a Friday to Sunday,

and then on Monday everyone
would be like, "Okay.

Well, we kind of just divided
up the company, like, in

thirds on Saturday morning,
'cause that's when we decided

we were gonna work together.

Yeah.

And now it's Monday, and like,
that guy's kind of an idiot.

I don't think I want to give
him a third of this company.

Just 'cause he showed
up at this event.

He's not even from

here.

He just flew back
to somewhere else.

Like,

what are we gonna do

now?

Yeah, yeah, yeah.

I always remember that,
'cause Ryan, you remember, we

used to meet with all these
folks on a regular basis.

Oh, yeah.

We were really involved
in, in those events.

And I remember the hangover
on Monday morning, where the,

usually the person who had the
idea was like, "Man, I just

gave that guy that just happened
to be in the room, like, a

third of my company." Yeah.

Because he was the only person
that, that could write code

on Saturday morning, right?

Which is like- Yeah

you know, when they
started to work in earnest.

And I was like, "You know
can undo that, right?

Like, you can go start
another company, whatever."

And but I always remember
the look on the founder's

face, where they're like, "I
think I made a huge mistake."

Yeah.

'
Cause you did.

Yeah.

You, you gave a third or half
your company to essentially a

stranger for what they might
do someday, and probably won't.

That is bananas.

Yeah.

Why are you freaking out-
It is … about that?

Yeah.

Right, I know.

That's the thing.

It's, it's, yeah, like we,
we treat investor equity like

it's some kind of fine china.

Yeah.

And co-founder equity
is like bar peanuts.

Just everybody stick your
hand in and get what you want.

Uh, don't worry about it.

Yeah.

It, it- Half the
company isn't a gesture.

It's a life sentence on your
cap table, for God's sake.

A life sentence.

Like, you are doing so much
to the company- It's crazy

… by making that decision.

Yeah.

With objectively very
little information.

And unlike investor
equity, which comes with

a receipt, nothing, right?

Yeah.

Investors pay in cash.

Everybody else pays in maybe.

In maybes and promises, right?

Yeah.

And to be fair, I want
folks to hear this.

Most of the people you're about
to give equity to, or have given

equity to, will not perform.

They will not perform, right?

And it's not because-

It's math.

Right.

It's, uh… And, and, but
here's why they won't perform.

Number one, because startups
are transient and hard, right?

Like most- Yeah … people, once
the, the fog and pixie dust off,

I wanna go join a startup wears
off, and like- Yeah … oh,

it doesn't pay anything, and I
have to, you know, consume all-

Which takes about two weeks,

by the

way.

Yeah, yeah, yeah.

It's, once people sober
up basically, they realize

it's a terrible idea.

Right?

Which is fair, okay?

Another reason is the startup
changes so fast that what-

So fast … you thought you
were gonna do, or what they-

Yeah … thought they were
gonna do, or whatever the

conditions were when you made
this pact Just don't apply in

three, six, 12 months, right?

Right.

So nobody's fault,
but the playing field

changed completely.

The game changed completely.

The other thing that you
run into is that for a

lot of people, what they
think their value will be

and what it actually is,
is dramatically different.

Yeah, yeah.

It would be like me saying that
I wanna play for the Columbus

Blue Jackets in the NHL, right?

Like, I'm a pretty good
hockey player, right?

Um, I can skate pretty well.

Yeah.

I can… You know, you've
played hockey with me, Amari.

I'm okay, right?

Yeah, yeah.

You left some bruises on me.

Yeah.

But if I took that same
impression of myself and

took it to that next level, I
wouldn't make it off the bench

before getting leveled, right?

Like, and, and that would be
the shortest hockey career ever.

Yeah.

And I use this to
say my s- You're

not getting into the stadium
without a ticket, let's put it

that way.

Yeah, yeah, exactly.

So m- my self-assessment of
what I think my performance is

going to be- Yeah … doesn't
mean jack shit, and that's

what I'm getting paid on.

Because I'm gonna tell
you, I'm gonna go out

there and nail goals.

I'm probably gonna have
a hat trick- Yeah … you

know, every single time.

Yep.

Yep.

And I can say whatever I
wanna say, but I also have to

show up and do those things,
and most people just in

life can't do those things.

They, they can't, you know,
execute onto the best of their

ability, which is why- Yep
… there's a delta in performance.

Yeah, I mean, how often
do we see this, Will?

Founder gives 50% to, let's
say, a technical co-founder,

'cause I think that's one of
the, one of the, the biggest

ways we see- Yep … people
part with equity, because they

need someone to build it, right?

Yep.

And they, they can't
do it themselves.

They don't have
the money to do it.

Six months later, the
product's barely shipped

or not shipped at all.

The relationship
is really strained.

The founder's now
negotiating with someone

who owns half the company-

Yeah


and maybe isn't even
full-time emotional.

It, it, like, and they're not
even there emotionally anymore.

Mm-hmm.

Maybe they are, they're
there, maybe they're not.

But it puts you in such a
weird position as a founder.

Yeah.

Right?

The wrong co-founder doesn't
just cost you equity.

I think that's something
really important here.

Yes, it costs you the
equity, but it also

costs you optionality.

Big time.

It costs you speed.

It costs you sanity,
and it can just, it can

absolutely wreck things.

Yep.

And so I think we have to be
careful here that this doesn't

stop with the equity, right?

The term sheet isn't the end of
your suffering, unfortunately.

Right.

Well, and, and I think,
you know, with the, the

co-founder, to your point,
you can get other investors.

Getting another- Yeah
… co-founder, not unheard of.

It does happen.

Yeah.

Co-founder cycle.

But it's pretty painful,
and it's pretty expensive.

Yeah.

But most importantly, there
is a guarantee of nothing, and

this is just with humans, right?

At least with the- Yeah,
yeah … investor, there's a

guarantee of cash, you know?

Say what you will- Right
… about the equity- So-

that you're gonna give up.

You are going to get
market value cash.

Yeah.

With all of these other
resources, the co-founders, the

employees, the advisors, you
know, humans in general, you're

gambling every single time.

It'd be the- Exactly
… equivalent of this if the

investor came in and said,
"Hey, here's the deal.

I'm gonna give you a million
dollars for 20% of the company,

okay?" And you're like, "Okay."

Yep.

"
Sure.

But I may not give it to
you." Yeah. "But you are gonna

give me 20% of the company.

And over the next- Yeah … two
to five years, every day you'll

come to me and say, 'Hey, will
you give me the money?'" And

every day I'll think about it.

I want to, right?

I'll say that I want to.

Yeah.

Yeah.

But I probably won't.

But you're gonna give me
the million dollars anyway.

How many people would be
like, "That's a great idea.

Where do I sign up for that?"
That does sound perfect.

And yet they do it every single
day- Yeah … with people.

Right.

Every single day.

Yeah.

And yet they'll haggle with
an investor over a couple

of points- Yeah … who will
actually wire the money.

Yeah.

Right?

And then they'll turn around
and give half the company,

so in, in, based on your
math, that would be $2.5

million worth of equity-

Yeah


to someone who
might do something.

Who might do something.

Right?

Right?

And probably won't.

But l- let me stick
with that, though.

Let's say it's, it's
the equivalent of $2.5

million worth of equity.

Now- Yeah … of course I wanna
lay the foundation, everything

we're about to talk about, in
the fact that right now you

don't actually have that money.

However, if you did, if you
had $2.5 million, would you

give it to that person- Yeah

in addition to what you're
gonna pay them for whatever

intangible value that you think
that they're gonna provide?

The answer's almost
always no, right?

Always no.

Yep.

If I had $2.5 million, I would
never give you that money.

Well, guess what?

Yep.

That's called an employee.

Uh-huh.

Yep.

Like, that's what employers
are for, where you just pay

them to do their jobs, and
they do their jobs, right?

Yep.

Giving some, like,
disproportionate massive

amount of, of money to somebody
for what they might do,

especially in the early years,
we have no freaking idea-

Yeah


is a dangerous gambit.

It is.

But nobody sees it that way,

right?

That's, that's what I'm saying.

What, what they're looking at,
what they're looking at at the

beginning is, like, well, it's
worth nothing, and I'm asking

so much of them, all right?

And so, so what
do we have to do?

What would be fair, right?

Oh my God, this is the word that
enters the conversation that

absolutely blows everything up.

Co-founder grants should be
priced like an investment,

like you just said, right?

Yeah.

Not a wedding vow, right?

Yep,

yep.

Till death do we part,
and if we do, you get 50%.

Yeah.

Um, because how many times
have we seen this, man?

And they're rarely

memorialized.

Yeah, right.

Yeah.

Fairness at the start,
right, it, it feels like

the right thing to do.

Right.

But how often have we
watched fairness at the

start- Absolutely rot into
resentment at scale once

they start moving, right?

It just, it happens so
often because as you said,

right, the businesses move
fast, and not everybody

moves at the same pace.

Not everyone is gonna keep up.

Not everybody's gonna
stay there, right?

Just because you're in early
doesn't mean you were in equal.

Right.

Yeah.

And, and I think that's
where this goes wrong.

We got equal shares for what
end up being really, really

imbalanced inputs and, and
outcomes, and it, it achieves

a, a real huge problem a couple
months or a couple years down

the line when all of a sudden
the one who is putting in most

of the time and has exactly the
same amount of equity and is

creating most of the outcomes
and has exactly the same amount

of equity starts to kind of
go, "Hmm, why is it like this?

Oh, yeah, that was
fair two years ago,

three years ago." Yep.

And, and now it no longer is.

I gotta tell you, I was on
the other side of this where

I was the unfair co-founder.

Let me give you an example.

This is actually, uh,
last company I did before

startups.com very long time
ago, like 15 years ago.

I'd started a company called
unsubscribe.com, and I had

the idea for the company.

Um, I had some people in town
in Santa Monica that I w- I

wanted to start it with, and
I'd kind of like a, a game

plan for how it would go.

And so I recruited two
other co-founders, right?

And at the time, I don't
remember exactly what the equity

split was, but, you know, l-
let's say it was like I had,

like, 50% or 40% and they, the
other two had, like, 30%, right?

So- Okay … I had the majority,
but it was my company, my idea.

However, and this is, this
is where it turns, I had

no intention of running it,
which is why I recruited

the other two, right?

Uh-huh.

One was a CEO candidate, the
other was a CTO candidate.

That company ended up raising
money, like, overnight.

Like, overnight, right?

Like, from, like, super brand
name investors like Charles

River Ventures, et cetera.

Uh-huh.

The other two co-founders came
to me- And they were like,

"Hey, Will, like, we totally
recognize that, like, you

brought us together, it was your
idea," and blah, blah, blah.

Uh-huh.

"
But we're gonna be all
in on this." What is

it that you do here

exactly?

Yeah, exactly.

That's exactly.

What do you do here exactly?

And I remember having
this very long, very

uncomfortable conversation-

Oh, yeah


with these other two
co-founders, right?

It wasn't that they
were wrong, okay?

It wasn't that they
were wrong, it's that

I didn't like it, okay?

I want to point out, like,
we assume that there's a

rationality that goes forward,
and there is not, right?

Like, I was like,
"Fuck you guys.

This was my idea.

I literally brought… You
guys are the reason, like,

that you're here, or I'm the
reason that you guys are here.

How… And we just raised money.

Like, how am I the
one getting fired?"

Because

of you.

Right?

Yeah, yeah, exactly.

Yeah.

Now, now in retrospect,
they weren't wrong.

But also you have to fight
with for what's yours or

people will gladly take it.

But I guess what I'm trying to
say is, this is a case where

we equally s- uh, split things
up, not perfectly equally,

but close enough, right?

And as soon as they realized
that I was on the wrong

end of the cap table, if
you will, they came to me.

And to be fair, they were
very professional about it,

and they were very cogent.

And, and eventually
I relented, right?

However, however, this is
one of those cases where I

recognized for the first time
that I was the problem, right?

Like, I was- Yeah … the
thing kinda like holding

it back, so to speak.

And to be fair, I wasn't
planning on working

there, so like, I only
had so much leverage.

I'm like, "Oh, you guys wanna
work on this full-time and

make money?" What do you mean,

guys?

This is going exactly to plan.

Yeah, exactly.

It is the case, even if you're
well-intentioned, even if you're

the goddamn founder, that you
could be the- Yeah … wrong

person in that equation.

Yes.

Right?

And not easy to unwind.

That's something really
interesting, 'cause, like, when

we get into the are co-founders
worth it piece, it'd be fun

to go back and actually look
at, like, original idea versus

founder who actually really
was the one that carried it,

and see how often it is that,
like, it's the original founder.

'Cause we often think of the
co-founders kinda like second,

and sometimes things do start,
like, they, they start so early.

Yeah.

And I think you and I
would both agree on this.

Yeah.

That at that early idea
stage- The idea's really

not worth that much, right?

Right.

It is the execution.

It's all the other stuff that,
that actually makes it valuable.

And to see really, like,
how often kind of the, the

second and the non-idea
person is the one who actually

creates a lot of the value.

Yeah.

But let's do something
here, because I don't wanna

leave this up in the air for
founders who are just sitting

out there like, "I would
give up 50% of my company

for the right co-founder,"
because we hear this a lot.

Yeah.

I got a couple things that
I, I, I generally wanna

say to them when, when I
hear these kind of things.

Yeah.

And I'd be curious what
then you'd add to the list.

It's start with vesting.

Always vest.

Add some cliffs.

Mm-hmm.

Tie additional equity to
actual value creation.

Define what happens if they
stop contributing, and put some

breakup terms in writing before
there's anything to fight about.

Because once the fighting
starts, there's gonna

be no fairness left.

There's gonna be no- Yep … no
coming to terms at that point.

What, what would you
add to that list?

Here's what I would say.

The best thing about that
conversation is it forces

expectations to the table.

Oh, yeah.

And for both sides.

And I think if you wanna set
up that conversation properly,

I think the conversation
has to be bidirectional.

It has to be-

Oh, yeah.

Gotta be … I need to know what
your expectations are, right?

Yep.

If things were to go wrong,
if I were to be the shitty

co-founder, like, you know,
let's say I'm talking to my

two partners at Unsubscribe.

If I'm the shitty
partner, I need to know

what your expectations
would be of me, right?

And if you're the shitty
partner, uh, vice versa.

One of my first partners in my
first business said this to me

when we were doing the deal.

I was, like, 22 at the time, so
I didn't know a lot about stuff.

And I said, "Man, these feel
like, like, feels like a really

onerous conversation." We
were merging our two agencies.

Yeah.

And he said, "Look, we always
start by writing the divorce

papers first, 'cause if we can't
agree- Yeah … on how it'll

end, we don't know how it's
gonna start." Like, for some

reason, that always stuck in my
head, and it was a very friendly

conversation, but just like
a term sheet- Yeah … about

super onerous shit, right?

Like, what happens if- Yeah
… you're convicted, right?

Like, crazy stuff.

And, um, anyway, I really
thought in those, those early

conversations that whenever
you say, "I need to address

your concerns or your desires
or your needs," it didn't

feel like, "Let me draft up
your execution papers," right?

Yeah.

It, it drafted up, "Let's
figure out so you know ironclad

what's fair to you- Yeah

ahead of time." You
know, again, what your

expectations are, et cetera.

Yeah.

And I, I found that
worked very well.

Because I think when other
people see it from, "Oh

wait, I might get screwed?
You're not just worried

about you getting screwed?"

Yeah.

"
Yeah, all of a sudden I'm,
I'm real interested in kind

of what this looks like."

Yeah, no, I think it
is super important.

I mean, I think that, that is
actually what fairness looks

like at that early stage.

Yeah, right, right.

Not 50% of the company.

Fairness is, "Let's have a
conversation around this.

Let's, let's talk about
exactly what happens in,

in the unlikely event of
a water landing," right?

Right.

That's a great

way to put it.

So those things do
need to be addressed.

Early employees,
same issue, right?

I was… That's
where I was going.

On average, startups
are gonna give up 15

to 20% of the company.

In an option pool.

Now, now typically option
pools are a little bit

smaller when they come from
investors, between 5 to 15%.

I went up- Yeah … to 20
just because a lot of times

you've got a lot of early
employees that are granted,

like pre-option pool, et cetera.

So the option pool- Yeah
… isn't always exclusively,

you know, just what was set
aside on serious seed funding

or something like that.

But let's, let's use just
a, a simple number of 15%.

That's a huge bit of the
company, and it's super hard to

ever get back or unwind because
it's tied into so many people,

which is where the problem is.

Yeah.

Yep.

Lots of, lots of little fights.

Yeah, exactly.

If someone's gonna take 15% of
your company as an investor,

you have a term sheet which
has all the terms that,

that they're gonna invest,
like at all the rules and

regulations, so to speak.

You've got, that'll transfer
to an operating agreement,

which will then memorialize
all of those terms.

You kind of know
what you're getting.

Yeah.

Here's the cash and here
are the terms, right?

Yep.

And it's, so long as you
understand those, the

deal has, doesn't have a
lot of questions to it.

Employees don't work that way.

Employees show up, and it's
just like a co-founder, "Here's

what I'm gonna do. I'm gonna
do blah, blah, blah." Right?

And statistically they will not.

Right?

Just Yeah … the
nature of people.

Otherwise, every company
would just keep the people

that they had forever and
there would, there would

never be a termination
or a turnover, right?

Doesn't work that way.

Uh, life works a
little bit differently.

But here's the challenge.

There's management
of people, right?

But there's a big difference
between, "Hey, you're not

doing a good job," and,
"Hey, you're fired." Okay?

Here's- Yeah … and
here's why I say that.

"Hey, you're not doing a good
job," can keep you around

long enough to make it through
your vest period, right?

"Hey, you're fired," sometimes
even has an acceleration to it.

Yeah.

But a vast majority of people
can earn the same amount

of equity Whether they do
a good job or a bad job, so

long as they don't get fired.

I was seeing the scene from,
uh, is it Office Space?

Where he's sitting in there
with the two, the two hatchet

men, and he's like, "What
that'll do, Bob, is you'll,

you'll end up doing just
enough to not get fired."

Yeah.

Right?

And, and that's, it's
kind of it, right?

Exactly.

It's, because look, if,
if equity's making up

for, for below-market
cash comp, great, right?

Yeah.

And sometimes, and
that's a real trade.

Yeah.

Yeah.

I would argue it, it can be
a really bad trade still.

But at least it's a trade.

For both sides.

Yeah, yeah, yeah.

But I was talking,
yeah, that's exactly it.

I was talking to a founder
two weeks ago and they had

layered equity on top of
really strong market comp.

Right.

Without any kind of
performance accountability.

Right.

Which just ends up being silent
overpayment and, and they were

at this point now complaining,
it's like, "Yeah, the team

just isn't motivated and I
did all this stuff for them."

It's like, when did you do it?

At the very beginning.

And what do they have
to do to maintain it?

And it just went dead silent.

Not get fired.

It's like- Right


well, they, they got it.

Not get, and- Right?

Like, no.

It's, in, in some of
these cases, there

wasn't even vesting.

So they were just handed
pieces of the company.

Oh,

shit.

Yeah, and, and- And
they have them now


and look, man, I'm gonna make
a few arguments having been

in this game for a long time.

And, and Ryan, you've
watched a lot of pr- people

come through our company-
Oh, yeah … over the last

15 years, so you, you've
seen it firsthand as well.

For sure.

But it's not exclusive to
folks that have worked for us.

First things first is we give
out equity as an incentive

for the future, right?

And, and everybody's like,
"Okay, I'll take it." Now,

what you said a moment ago,
some people are using it to

actually, like, be a part
of their cash comp, right?

I would argue at which
point you can't pay someone.

Let's say somebody makes
$200,000 a year, and you

can only pay them 100,000
and they're gonna take the

other 100,000 in equity.

Totally fair trade.

Yep.

That's money you didn't have-
Yep … that you would've

otherwise paid them, okay?

Paid

somebody.

Totally fair.

Yep.

Right.

Yeah, yeah.

In that case, I would argue
that they've earned every bit

of it because that was what- Yep
… they were gonna earn anyway.

You just couldn't
pay them, right?

Yeah,

exactly.

Straight up.

Uh, I get that one.

There's a different version
which you just said, which

is we're kind of gonna pay
you what you're gonna get

paid anyway, and you're gonna
get a whole bunch of stock.

And-

Whether you perform or not,
which is where I wanna take this

What's missing in this deal, and
this goes back to the premise,

you know, of this episode,
which is why don't founders

look at the other places they're
giving equity as stringently

as they do with investors?

If I say to you, "Hey, you get
paid $150,000 for whatever job

it is, and you're gonna get a-
an extra $200,000, let's say, in

equity." First question is why?

Like, like- Yeah … what
exactly, how are they

gonna perform differently
than they would've

otherwise performed, right?

In other words, if they go to
another company and they don't

have equity, are they just
gonna not show up for work?

Like, what, what- Yeah … is
it about that, that equity?

I have not seen, in my
years, a dramatic difference,

a dramatic difference.

I've seen a difference, not
a, a dramatic difference

the way people think it is,
between someone who makes a

good m- you know, market rate
salary, like they're well-paid

and someone who has equity.

Now- Yeah … a
few caveats there.

Very few companies ever
get to a point where

equity is valuable, right?

I mean, like, it's,
it's statistically tiny.

Bit of a lottery ticket.

Yeah.

Yeah.

Which is, which is why I said
a moment ago that at what

point you're paying people a
full salary and then paying

people on top is very different
than if you're actually

subsidizing their comp,
you know, with your equity.

At that point, it's not
a lottery ticket anymore.

Yeah, man.

If your employee's

getting paid market rate
and gets equity too, that

equity needs to go get a job.

Yeah.

Like, come on.

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

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.

So, yeah, here's
what I'm saying.

From the employee's standpoint,
I think for a lot of employees,

they look at it as, "Oh, I'm
working for a startup company.

I, you know, I deserve a piece
of the thing." Every single

person that's ever worked for
us has been g- has been given

an, an equity grant, right?

It's vested over time,
but, uh, you know, they've

been given an equity grant.

Because I do believe, I…
You know, when, when and if

that payday comes, I want
everybody to take, to get a

piece of it, and that's great.

Yes.

However, however, there's
also a side of it which is,

wait a minute, if we were
to sell today, the people

that work really hard and
the people that just didn't

get fired get paid equally.

Everybody gets a Super
Bowl ring, right?

There is a great, uh… I
told you about this guy.

Uh, there was a great
entrepreneur that I was

meeting with maybe, like,
a year and a half ago.

Uh, we're at a, a restaurant,
and, uh, he's pitching me

on this, uh, on his idea.

And he's, like, notably
athletic, right?

Uh-huh.

You can just tell, like,
when some people are like…

There's athletes who, like, go
to the gym a little bit, and

then there's a professional
athlete sitting- Yeah … next

to people who don't, who just
go to the gym a little bit.

Yeah.

And this guy was the
professional athlete, right?

He was like, like- Uh-huh
… 6'4", like 4% body fat, right?

Like- … not just
a dude, right?

A dude, right?

Right.

Anyway, as he's sitting there
talking, I see this giant

thing flashing on his, on his
ring, or on his, his finger,

which is a ring, right?

Uh-huh.

And I'm like, "I, I gotta pause
for a second. Is that what

I think it is-" What is it?

"… on your ring?"

Yeah.

"
Or on your finger?" And
he's like, "Oh, yeah,

it's a Super Bowl ring."

And I was like, "And you
failed to mention that -" Yeah.

"… in this conversation?" He's
like, "Yeah, I won this

with the Broncos." And I was
like, "Dude, that would've

been the first thing I said
in every conversation-"

Yeah "… I've ever had."

Yeah, "Will, why do you wear
that ring in the middle of

your forehead? Isn't that
supposed to go on your finger?"

Yeah.

But here's what he said, which
I thought was interesting.

He's like, "I never stepped o-
on the field one time," right?

Like, "I, I-" Yeah "… was
like second, third string.

E- everybody gets a ring." He's
like, "You know, whether you

play or not." And I use that.

He's a great guy, by the way.

And I use that as a
metaphor- For this, right?

Like, if we were to sell today,
every person that's ever worked

for us that has equity, whether
they performed well or not,

is going to get paid the same.

Paid the same meaning like,
you know, that their equity's

gonna convert the same way.

And I'm like, "Well, shit."

What happened to fair?

Didn't we s- wasn't fair where
we started with all of this?

Right, right.

Yeah.

And so my, my point with
employees is you're paying

employees equity not because
they're, they're gonna

perform so well, because
they're not gonna get fired.

And I use the latter- Yeah
… to say I know the incentive is

that they'll work harder, and
that might apply, but the cost

is gonna be exactly the same
whether they work harder or not.

You know, same with salary,
but certainly with equity.

Here's what I've seen over time.

It does work with some people.

It does work with some people.

Ironically, those are the same
people who would've worked

and compounded value for
the company whether you give

them equity or not, right?

That,

that, that's

my

point.

The, the value add players
are always gonna be

value add players, right?

A- a- and unfortunately,
I think we too often treat

early employee equity as a
signing bonus when it really

needs to be treated like
a value exchange, right?

Because if it's just, if
it's just a signing bonus

and it's granted at the
beginning, even if there's

vesting involved, right?

Like, vesting isn't value
creation, it is just

time passing, right?

That happens whether we
do a damn thing or not.

Showing up is not the same as
compounding the company, right?

Right.

In, in my opinion, equity should
do, should reward three things.

Three things and
three things only.

Risk, sacrifice, and impact.

Ideally, all three.

Yeah.

But it has to have some
semblance of at least one

of those things for it to
really be a fair exchange.

On that note, let's
move to advisors.

So we're just, got like
the third leg of the

stool, if you will.

Uh-huh.

Advisors crack me up as
a category that, that

gets, uh, equity, not
because they get so much.

I mean, honestly, uh,
advisors, like, don't, don't

ever really compose that
big of the cap table, right?

You know, as far as the-
Right … slice of the pie.

No, but it is, but it's
another great illustration of

how easily founders will part
with it and really not think

through, "What am I actually
getting in return for this?

Would I pay the same thing
for it if it was a cash

payment?" And the answer
is almost always no.

Let me lay this out, 'cause
I, I think we just have

great data to run this, okay?

So currently, uh, this is,
this is coming from, uh,

Carta, I believe, you know,
who does cap table management.

Advisors are currently getting
between .10 to .25% of the

company for their advisory work.

So for, for those of you that,
that are following at home,

that means a 10th of, of 1%.

That is per advisor, not,

not as a- Uh, correct, correct.

Per advisors.

Yep.

Right?

And so, you know, l- let's
say you've got, you know,

three to five advisors, you
know, that could easily cost

you a full point of equity.

Which- Yep

here's where this
gets dangerous.

Numerically, that's
a very small amount.

That's less than 99%-
Yeah … of the rest

of the company, right?

Yeah, yeah.

However, however, where it
gets hilarious is when you

start to do the math of
what it actually buys you.

Here are the categories
that investors usually

get recruited under, okay?

Most popular, category
A, sage-like wisdom.

They have, they have some
sort of sage-like wisdom on

either an industry- Oh … or
a- Yeah … particular, um,

skill set, you know, marketing,
things like that It tends to

be the biggest one, right?

Like, I need somebody… It
used to be back in the day,

like, like the oldy-timey
boards that you put together,

advisory boards- Yeah

were like a doctor, an
accountant, and a priest, right?

I'm kidding, but like- Uh-huh
… it was always like the same-

Cover the basics … like, g-
gaggle of G.I. Joe characters

that you, that you'd- Yeah
… go out and recruit, right?

'Cause you needed
those, those skills.

People often found attorneys
'cause they need legal in the

early days, things like that.

Anyway, regardless of who it
is, the problem is the same.

You're trying to tap that wealth
of knowledge, and you don't,

you don't know what it's worth.

Second thing that I see is,
"I wanna tap a network."

Introductions to customers-
Yeah … introductions to

investors, intro… And by the
way, those can be valuable.

Yeah, yeah.

They can be.

There is an
opportunity for value.

But it doesn't mean-
Yeah … there's value.

Now, so what's interesting about
advisors, unlike employees,

and why we get to them last,
is because they're probably the

most unaccountable part of the
entire cap table distribution.

I know so few advisors that
have actually done the things

that startups thought they
would do, myself included.

Yeah.

I've been asked a billion
times, I know you have, to

be advisors for startups.

I always tell them
the same thing.

I said, "Look, I can be
valuable, but I won't be

valuable." And they go, "Well,
what does that mean?" Yeah.

Right?

I was like, "In your mind, how
you think I'm going to help

you isn't how I- Yeah … plan
on helping you," right?

We were like, "Oh, we- we'll
open up his Rolodex and m-

introduce you to, to all
his investors." No, I won't.

No.

Nope.

That doesn't sound like
a lot of fun for me.

Or, "Will's gonna get involved
in our team and he's gonna

help us daily, you know, to,
to make some decisions." Nope.

Nope.

I got shit to do, man.

That's called employee.

Yeah, yeah, yeah.

Yep.

It's not that I don't
wanna be helpful.

We literally advise startups
for a living, right?

Which is why- Yes … I
don't wanna do more of it.

But it's, it's, I think
the expectations of what

advisors can or will do
pale in comparison to

what they actually do.

Yeah, man.

Like, we, we see people make
mistakes with this all the time.

Mm-hmm.

And, and I think it starts- Yeah
… with, with founders confusing

reputation with contribution.

Right.

A famous advisor who does
nothing is just really

expensive wallpaper, right?

Or the most expensive LinkedIn
endorsement you'll ever get.

Advice is only valuable if
it does a couple things.

One, changes decisions-

Yep

opens doors, or
reduces mistakes.

And I think that where we end
up in this trap is that as, as

founders early stage, we find
people who do those things.

We talk to somebody once
and they give us some

valuable advice- Yep … and
it changes one of our

decisions for the better.

And then we go- Amazing
… "Great, we should make

them an advisor," right?

Most of the time, that's the
one piece of valuable advice

they had, and now we've
just permanently attached

them to our cap table and
paid them what could end

up being tens or hundreds
of thousands of dollars, or

millions of dollars, depending
on how big the company is.

You have a, you know, a, a
big, big exit, that 1% all

of a sudden becomes worth
a lot of money, right?

This isn't take a penny,
need, need a penny, take

one, have a penny, leave
one- … kind of thing, right?

It's, I think advisor equity
is, is one of those places

where tiny percentages
hide giant waste, right?

We see this in lots of
places in a startup.

Yep.

Um, but this is one of
those where it's just,

it's so glaring to me.

It's interesting because from
the advisor's standpoint, I

think they're well-meaning.

I definitely don't wanna paint
advisors, right, as some, like,

shysters or something like that.

That's not it.

It's not the advisor's fault.

It's the founder's fault.

The, the founder loses this
in a few ways and, and again,

y- you learn as you go.

The first place you lose is you
don't clearly define what you

expect the return to be, right?

Yeah.

Ryan, I'm gonna give
you .25% of the company.

Here's bullet points of
exactly what you need to

deliver in order to earn that.

Uh-huh.

If you don't nail all of these,
you won't get your equity.

I guarantee the number of
advisors that agree to that

is geometrically lower.

Think about why for a second.

Here, here's, here's an example.

Take this from the same
standpoint if you were

hiring somebody, okay?

Yeah.

And the person sitting across
from you, the interview

candidate, and you're
like, "I need you to show

up for work every day."
They're like, "No." "I need

you to come to meetings."

"No." "I need you to work for
the company eight hours a day."

"Nope, not gonna do that." And
you're like, "You're hired."

That's essentially, like,
the mismatch of expectations.

And so- Yeah … now, I
will also say, similar

to employees, advisors
want to be those things.

They want to be this
fountain- Yeah, of

course … of knowledge.

They want to be
this helping hand.

They wanna be, you know,
make a good connection

that works out for you.

They want to do all
of those things.

It doesn't mean that
they can or will, right?

Right.

Like, I've got a pretty
big Rolodex of investors.

I theoretically could introduce
you to them, but now, when

it comes time to actually
do it, here's how the math

changes very quickly, right?

I look at all of my,
my, uh, contacts.

On the one end I've got Roelof
Botha, who's the managing

partner of Sequoia, right?

I've known Roelof for 20-
Yeah … something years, right?

He'll take my call once.

Uh-huh.

Like, he's pretty busy.

Actually, I don't think he's
the managing partner anymore.

Yeah.

Anyway, uh, and on the other
end it's, like, just some rich

dude that I know that, you know,
I, I could introduce you to.

I want to make these
introductions, but I'm not going

to if it's gonna burn social
capital that I can't get back.

Right.

Yep.

If I introduce you to, to
Sequoia and that goes horribly,

there's a fairly good chance
that I've, you know, soured

my relationship with Sequoia,
and I don't get it back.

Yep.

No skin off your back.

Over 0.25% of what is
still monopoly money.

Right.

Right.

This is… All I'm trying to
say is that technically I could

make all of these introductions.

It doesn't mean
that I can or will.

So your perception of
what my value is doesn't

necessarily align with
what my ongoing value is.

Which brings me to point
two, ongoing value.

Yeah.

I have a million things that
I can tell you about your

business that are gonna be
like magic tricks to you.

I can tell you about-
Yep … like how to update

your, your pitch deck.

I can tell you about what to say
in a pitch meeting, et cetera.

But once you don't need
those specific markers,

those specific, uh, moments
in the journey- Yeah

I might be useless to you.

We have late-stage people
that come to us, right?

And they're like, "Hey,
yeah, I've, I've solved

all the early-stage stuff.

I've got some late-stage
problems where I'm trying to

let, like, uh, refocus the
cap table, or, or I'm trying

to figure out what expansion
rounds look like." And I'm

like, "I can offer some advice.

I can't offer- Yeah … the
best advice." Right.

Because when you get to that
stage, different skill set,

different, a different world.

I'm certainly fluent in
it, like I understand it-

Yep


but there are people
that are better at that.

Conversely, those people aren't
good at the early-stage stuff

like you and I are, right?

Correct.

So, like-

Yeah


my point is, you hitting us
up for early-stage value and

expecting us to be perennially
u- useful is probably unlikely.

And of course everybody
wants to be, right?

And I guess, again, like, like
you said, the, the advisors

would hope that they can be.

Yep.

Uh, but I think in, in
reality it's just the, it's

time diluting value, right?

There's gonna be a curve at
which they're, they're no

longer as valuable to you as
they were in the beginning,

and yet you've now tied them
to yourself permanently,

which is the problem.

Do you remember who,
who Jim Grote is?

I do.

Um- Wow.

Yeah.

Yeah, all right, uh,
hear me out, right?

Jim Grote's the founder
of Donato's Pizza,

for, for folks- Yeah

who don't know.

He's also a, a local
legend in Columbus, Ohio,

where- Yeah, yeah … Brian
and I went to school.

Damn it, now I want
Donato's Pizza.

Yeah, I

know.

I

know.

I know.

Do you know how far I am
from a Donato's Pizza?

I can get a Papa John's here.

Not quite the same thing.

Yep.

I met Jim, uh, 20-some odd
years ago, and w- we were

at, at some event together,
and I got talking to him.

He's like super nice guy.

And I remember thinking,
someone at the time was asking

me for an intro to Jim, uh,
usually like, like within the

year, and they wanted to, to,
to tap into his knowledge.

Uh-huh.

And I remember something that
he and I talked about, and he

said something to the effect
of like, "Well, I've done a

lot of this, but I haven't
done a lot of this lately."

And it always stuck in my head.

I thought it was-

Yeah, yeah, yeah


his level of self-awareness
was extraordinary, okay?

That's incredible.

Yeah.

E- exactly.

Most people don't realize their
knowledge has a shelf life.

Correct.

Right?

Yeah.

And you know who
doesn't realize this?

Fucking advisors, right?

Yeah, the advisors.

No, that's what I mean.

That's what I mean.

Yeah, I, I think that, in
fact I think that's more often

spotted by founders than it
is the advisors themselves.

Yeah.

I think once you've, you've
achieved guru level, once

you've- Yeah … if somebody's
told you that you're a

sage, you're forever a sage.

Yep.

It's, it's tough.

I try to be mindful of
that because, like when I'm

dispensing advice, and you
and I do this for a living.

Yes.

I always try to like play my
own filter and bias to be able

to say, "Is what I'm about
to tell this person current?"

Like, and, and how can I
validate that it's current?

Yeah.

Right?

And so I always try
to be mindful of that.

And I think that for a lot
of people when they seek out

advice, what happens is they
get an audience with guru.

You know, whoever the
guru happens to be

in, in their space.

Yes.

Right?

And that guru knows a
ton about that space for

their moment in time.

They drop some, some
incredible nuggets, right?

And you're like- Right

"Oh my God, if I could have
access- Yeah … to this oracle

of knowledge all the time."

Imagine what else is
in their head, right?

Mostly ore, unfortunately.

Yeah.

You, you, you saw the gold.

And it turns out for most
people, they're just not

like a bottomless fountain
of freaking wisdom, right?

Right.

They know a couple things
that you don't know right now.

Yeah.

And then once you know
them- And guess what?

They tend to lead
with those, too.

Yeah, exactly.

They, they, they lead
with their best shots.

Yeah.

When I was starting my
agency, like m- like 19 years

old, I met this guy, right?

This guy named Don.

He, he's a great guy.

And he was a consultant,
and he was a marketing

consultant.

Okay.

And he was the first
person that I had met that

understood what marketing was.

I had no goddamn clue, right?

Right.

Even though I was starting
essentially a marketing agency.

He had gray hair, and
he presented well, and I

just thought- Yeah … he
was freaking Yoda, right?

Uh-huh.

Now, I owe him a huge, huge
debt, and he knows it, and

he, he reminds me every
single time I see him.

Because he- … he's the one
that introduced me to the agency

that, that ended up, uh, we
ended up merging with, right?

But at the time, uh, and
he, he and I have been

friends for a very long time.

At the time, he would say to
me, he'd be like, "You know,

this is the way things work,
and this is how you charge,"

and everything else like that.

And I remember, Ryan,
working for him for

pennies on the dollar.

I think my effective- Uh-huh
… billable rate for how much

he pimped me out was, like,
nine cents an hour, okay?

Because I thought he was this
fountain of knowledge, and I,

I was willing to- Yeah … you
know, give up and to learn

and everything else like that.

In, in retrospect,
probably a good idea, but

I wouldn't recommend it.

Yeah.

Many years later,
20 years later.

Don and I get together for
lunch, and, uh, and I'm like,

"Don, did you know at the time
that I was working for, like,

nine cents an hour?" He's
like, "Oh, hell yeah, I did."

Yeah.

He's like, "I was so upset when
you ended up doing that deal

and all, your rate went up."

You know, he's, I was like-
Yeah, that's hysterical … "So

you're just gonna keep taking
advantage of me?" He's like,

"Yep." He was saying it
like, you know, in jest, but

I always thought about that
moment where I'm like, damn,

dude, the only reason I was
willing to do that is 'cause

he knew something that I didn't
know at a time, you know, I

wasn't, I wasn't capable of
getting more of that knowledge.

And I was will- Right
… willing to pay a massive

premium in retrospect to get it.

And I was like, these
founders are easily misled.

And look, it is tough,
'cause you are making a

bit of a bet there, right?

And sometimes the
bet does pay off.

Right.

Right?

So i- in that case, that
investment that you made in

Don, it was an investment
that he made back into you.

It did.

In tro.

Yeah.

It all worked out quite well.

But it's not like
that went to plan.

It wasn't like there was-
Right … a plan there.

You're just looking at it-
Right … and going, "You seem

to know a lot more than I do,
so I am going to, uh, pin myself

to you, and, and we're gonna
see what happens." It's a long

shot bet, and I would say for
every time it works out as

you've just described, there are
20, 30, 40, 50, 60 that don't.

Think of the cost, okay?

So, so let- let's
put this out there.

Yeah, that's fair.

So if you've got, if you're
giving up a quarter point, let's

say, to an advisor, which is a
little bit on the higher end,

but let's use that, but you're
also doing it at a $10 million

valuation, which is usually,
you know, a good deal for a

pre-seed, uh, raise these days.

But you're paying
that person $25,000.

Now again, you're paying
them in equity future value,

which will probably turn
out to be nothing, so it's

not exactly $25,000, okay?

This has nothing to do with
whether that $25,000 is the

same as the investor money.

It's the fact that you're
haggling more over the investor

money than, than you are
over, over this, this 25K.

Yep.

And so think of how many
times you wind up pinging

that person in the time
that you work with them.

In your mind, you're talking
to them all the time, and

then they're always up
in your world, et cetera.

We have advisors
at Startups.com.

I won't name names-
Yeah … 'cause they're

all great people, right?

But big brand names that you've
probably never heard of 'cause

we failed to mention it, right?

Yeah.

Who I think maybe- I have given
three requests to ever, right?

Uh-huh.

In the 15 years that we've
been around, like ever.

And I think on average, I
probably paid for each email

or phone call at least $10,000.

Yeah.

Right?

It ends up being a
pretty expensive email.

It is.

It is.

And I can't even remember
what the requests were.

If we look back, you know,
we own a platform, uh, called

Clarity, which of course is,
is, uh, an expert exchange.

This is ironic- Yeah … that
we're talking about

this because, like, we
actually know exactly what

advisors get paid- Yes

for actual real
world startup advice.

Yeah, yeah, yeah.

Because we write those
checks to the advisors

every time the startups ask.

Ryan, you've done
hundreds and hundreds and

hundreds of these calls.

Yes.

How many times have
you gotten paid $5,000

for a call?

For a call, exactly zero times.

Yeah, exactly zero times.

Exactly zero times.

Now, I have had tell, people
tell me the, the call was

worth $100,000 or that it saved
them two years to their life.

Yeah.

Awesome.

Which I would equate to several
hundred thousand dollars.

So value is there, right?

But nobody ever offered
to actually pay me the

full value of the call.

Yeah.

No.

Nobody was like, "You know
what? So we're gonna send you

half of that $100,000 you saved
us. We really appreciate it."

Right.

Never happened.

And on average, these advisors
who are getting paid by the

minute from startups to, to
give their advice- Yeah … and

they're great advisors.

I mean, I, I highly recommend
going on there and, and

finding some great people.

But are getting paid hundreds
of dollars for the advice.

Now, to be fair- Yes … it's
not because they're trying

to get rich off of Clarity.

We always said that Clarity
is iPhone money, right?

Like, it's, it… For, for
the advisors- Yeah … it's,

it's not all the money that
you, you'll make to make a

living, but it's enough to
buy a free iPhone, right?

But most advisors, yourself
included, are doing it 'cause

they wanna be helpful, but they
wanna, like, have s- like a

metric of their time, right?

Like- Yeah … hey, if you're
gonna take up 20 minutes

on a call with me, like, it
should have some friction

for you too, 'cause it
definitely has friction for me.

It saves you from the
Googleable advice- Yeah

uh, syndrome.

Yep.

Or at least you're getting
paid to Google for people.

Yeah.

Um, yeah, yeah.

Yeah, I, I did, I got, I got
called out once, uh, I don't

remember if it was on X or
on LinkedIn, but somebody was

like, "Hey, asshole, how can
you charge $400 an hour to…

What, what makes you think
you can charge $400 an hour to

talk to people on the phone?"

And I said, "Well- I pasted
back the two comments around,

"You saved two years of my
life," or 100, you know,

"Helped us make $200,000."

Yeah.

And said, "So, so there's part
of it." I was like, "The other

part is I started at 100, and
I got too many calls, and I

went to 200, and I got too many
calls, and I put to 300 and

I got a little less calls."

Yeah.

"And I put to 400, I got
exactly the number of calls

I wanted, which wasn't
too many, but people-

Yep … showed up really,
really well prepared." Yep.

"So here's the booking
link." He never called me.

Yeah, it comes back to here's,
here's the value of my time,

and here's the explicit cost.

But my point is- Yeah

even at $400 an hour,
no one would've gotten

to $25,000, right?

Right.

And, and that's
just one example.

That'd be a lot of hours.

It would take a lot of hours
to consume 25K, and that's

a lot of hours you're not
gonna get out an advisor.

You just aren't.

So here's what I would say.

I love the fact that
founders are really well

conditioned to price their
equity and hold onto it.

I hate the fact that they only
apply that rubric to investors.

Sometimes.

Right?

Which is the only person- To

the one place where
there's actually a clear

value exchange, right?

I know.

Now, you can argue whether it's
an equitable value exchange or

not, but at least it's clear.

You know exactly what

you're getting.

You will get it, right?

Like, like you will-
Yeah … get the money, right?

Yeah, yeah.

It'll be conditional
and everything else like

that, so it's- If you
don't, you won't give

up the equity, right?

Right.

Yeah.

Versus all these other
buckets where like, ah,

what could go wrong, right?

And like, you're just like,
like saying, it goes back to

what I said a moment ago, which
is you're literally saying

to, quote, "an investor", "I
am gonna give you the equity.

You might give me money.

Let's shake on it."

Yep.

Like, what?

So-

Yeah


all I wanna say is like, we have
to use equity to pay for stuff.

If there's nothing wrong
with doing a co-founder

deal or obviously giving
employees equity or, or

giving advisors equity,
that's not the argument here.

No.

The argument is
how you treat it.

The argument is how you-
Yeah … focus on that value

and how you pay for it.

If you're looking at that value
as amorphous, and you're just

willing to give up half the
company or a quarter point to

somebody and not be sure that
you're extracting that same kind

of value as you would from an
investor, you're leaving way

too much equity on the table.

There's never- Yeah … gonna
be a point ever in the history

of you building your company
where you're like, "Man, I wish

I gave away more equity," right?

"I wish I gave Brian
more equity- Yeah … for

those calls," right?

That'll never happen.

Yep.

What will happen is you're
gonna look at every one of those

transactions, and you'll say to
yourself, "Man, I really wish

at that moment I had treated
every single share that I ever

gave away exactly like a dollar
that I was taking back for

it and extracted that value,
because that's the only thing

I have left to show for it.

And in the end, that's
all that matters."

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