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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 Will Schroeder,
my friend, the founder
and CEO of Startups.
Dot com.
Well, we talk to lots and
lots of founders, right?
And we hear lots and lots of
founder origin stories and
so many of them track back
to early, early days, right?
Childhood.
Yep.
And so fun today to explore
like what's so unique about.
Childhood that most
founders do trace their
origin stories back there.
Why it seems that a lot of
the seeds for entrepreneurship
or foundership are
planted before we've even
made it to high school.
Right.
And I, you and I have
heard a lot of stories.
We have a lot of stories.
Why don't you open up with one?
I've got a lot of stories.
I love origin stories.
I love origin stories, right?
Like I love hearing how
founders, you know, kind
of came from nothing and
kind of built something.
What's fascinating about
it is how all those stories
sound so unique and yet they
all follow the same pattern.
Yeah,
yeah,
right.
You know, it's unique stories,
but with a very,
very common theme.
Yeah, exactly, exactly.
And again, they're extraordinary
in their own right, because
when someone starts with nothing
and then builds something, that
always makes for a great, you
know, rags to riches story.
Yeah.
Except It, like, it's so, the
same types of moments in time
seem to have happened to so
many founders, uh, early in
childhood that you start to say,
hey, there's something there.
Yep.
Right?
Like, there's something about
those formative years where
something really important
clicked for those folks.
And I think what we can talk
about, you know, we talked about
some of these stories, but we
can also talk about what is
it that clicked and how can we
get this in front of more kids
and get more kids clicking?
Right?
You know, how to
make this a thing.
How do we drive more clicks?
Something to think about a lot.
I love that.
Uh, and, and so, you know,
so we can talk about it.
So, let me give you
an origin story.
Where I grew up in, uh, in, in
Southern Connecticut was kind
of like a, a blue collar area.
Connecticut's generally
considered like a really rich
state, uh, not where I lived.
It was interesting.
It was like in my neighborhood,
there were probably no
less than 70 to 100 kids.
Kind of stacked.
These were old school houses,
typical eighties movie, right?
Like just roving gangs of,
of, of unsupervised children,
so many unsupervised children,
which, which is kind of,
you know, the setting for
this, these were a bunch of
homes that were all built
after the second world war.
So you had two family
homes that were maybe 800
to a thousand square feet
on the top and bottom.
And so now stack those
next to each other, and
now picture an entire grid.
Those are a lot of kids
getting let out, you know,
on a Saturday morning.
And so, so tons of kids
in the neighborhood.
And there's this, this
one kid, this kid's about,
uh, eight years old.
And, uh, uh, little boy,
uh, great kid, but had this
really Tough situation that
everybody in the neighborhood
was very familiar with.
Uh, he had grown up, he had
never met his father, so he had
a single mother, and the single
mom was gone all the time.
So picture, and this is like an
80s kind of era, an eight year
old kid completely on his own.
Completely on his own.
Also, without any You're just
reciting the intro
to Stranger Things.
It really does, it kind
of resonates, right?
Yeah.
And then there's this odd,
this odd event that seemed
to happen at the power plant.
Anyway, so this kid, on
a given day, like, around
like, um, dinner time, you
know, lights go down, uh,
whatever, would basically try
to figure out whose house he
could go to to get dinner.
Because there was
no dinner at home.
There's no parents at home.
And so, in very 80s fashion,
he would just kind of float
from like, you know, kid's
parent to kid's parent.
And that's kind of how he ate.
They also, around that time,
uh, everybody kind of knew
this, it was kind of sad, had
gotten evicted from their house.
So, they were basically
squatting on a, the floor
of a neighbor's apartment.
So this little 8 year
old kid, this is what's
interesting, because I
have an 8 year old kid.
So I think about this,
like, like, Pretty
easy to contextualize,
yep.
I know, to think of this in like
his terms when I think about
this, I can't picture an 8 year
old boy, like my 8 year old
boy, dealing with any of this.
This kid's super independent,
comes home, basically he's
sleeping on the floor of
a neighbor's apartment for
like a couple years, wakes
up in the morning, And, uh,
he's a cardboard box that
has all of his clothes in it.
That's his dresser, right?
Puts on his clothes, whatever.
He's like a, like,
pretty good natured kid.
On this particular day, though,
he goes, um, goes to school.
Back then, Heh, alright, if
you didn't appreciate this.
Back then, school lunch cost
a dollar at a public school.
You, you bought what's
called a lunch ticket.
And, uh, anyway, so, he
goes to the bus stop.
And on this particular
day, he's got a quarter.
On most days, on most days,
his parents didn't give
him money for lunch, so he
just had to figure it out.
Like, that was his thing, right?
And what's interesting about
that is, on this particular day,
he's like, I've got a quarter.
How do I make a quarter work?
Because I can't go to
school and buy anything.
So, he's at the bus
stop in the morning.
He goes across the
street to a market.
In Connecticut, they're
all called delis.
And he goes to the deli.
And he walks in, and
he looks around what he
can buy for 25 cents.
And he spots a pack
of Now and Laters.
Do you remember Now and Laters?
They were like, I
still love Now and Laters.
That's why they call them that.
I, I never understood why it
was called Now and Laters.
Like the candy doesn't
really change as you eat it.
Like it's the same thing
all the way through.
It's because I like them now
and later.
Yeah, and so, so he decides to
buy a thing of Now and Laters,
and if you recall, Now and
Laters were, uh, Five to a pack.
Six.
Six to a pack, alright.
I thought it was five two,
I thought it was five two.
Uh, I looked it up, it was six.
Anyway, so he buys some Now
and Laters, and the idea is,
this is, I mean, pretty clever
for an eight year old, that
he can basically ration his
food, and of course he's eight,
so he thinks it, it being all
sugar, can ration his food
throughout the day, okay?
Uh, just kinda how
he handles business.
So he gets on the bus.
And something really
interesting and life
changing happens to this kid.
He's, he's sitting in the
back seat, and one of his
friends says, uh, Hey, can
I have a now and later?
And here's the part they
kind of don't tell you about
in these origin stories,
is how humiliating that is.
Right, because think about it,
man, like, the kid's saying,
can I have a now and later?
And the kid's being kind,
he's just, you know,
asking for a now and later.
What he doesn't realize, that's
that eight year old boy's lunch.
Yeah, that's the kid's
Kellewerk intake for the day.
Right.
Exactly.
So, so what the kid does
is he basically says, Hey,
you know, kind of pauses.
And so his friend says to him,
well, Hey, I'll pay you for it.
And he's like, okay.
And he's like, how much?
And with the kid thought
this eight year old boy
thought was how much
should you pay for them?
So he says back to me, he
says, Oh, uh, 25 cents.
So his friend produces a
quarter because it's a lot,
a lot of money to him, right?
Gives him a quarter
takes the pack.
And then a magical
thing happens.
Takes one.
Gives it back.
Hands the rest of it back.
Oh
man.
And concept of margin
is revealed.
Exactly, right?
And so this little year old boy
has no idea what just happened.
But another friend sees this
happening and he joins in
and says, hey, I want one.
Gives him a quarter, right?
By the end of the bus ride, this
kid has sold all six pieces.
Right?
Buck fifty later, he's
got money for lunch and money
to
buy twice as much
inventory for tomorrow.
Mind blown, right?
And so, the coolest, the
coolest part about the story
though is, this kid goes
into the lunchroom that day.
In hands of a lunch lady, the
first dollar he's ever earned.
The
first dollar
he's ever earned.
The meal he paid for.
Exactly, and the pride
that comes with that.
And this is where it
all starts, right?
Where it begins.
Goes and he gets a
french bread pizza, which
you know, it's gross.
Oh man.
And he gets, uh, in
a chocolate milk.
But here's what's interesting.
He takes it, he goes like
into the corner of the
lunchroom where nobody
can see him, and he cries.
Yeah.
Right?
That, that was a lunch
he wasn't expecting.
But they weren't sad tears.
Yeah,
they were happy tears.
Of course, because at eight
years old, this little boy knew.
He'd never go hungry again.
It
doesn't have to anymore.
I have agency.
That's it.
I can change circumstances I
don't have to accept and deal
with what was handed to me
if I was handed a quarter I
don't have to sit at a quarter.
I can turn that into something
else and it is such an
amazing feeling And it's
amazing as like as parents.
Well, we see this a lot too
when our kids go through some
of these same realizations
Albeit, uh, none of them
have ever had to go, you
know, hungry or wonder where
their lunch was coming from.
But to watch a child understand
that they now have some level of
control over their environment
is something truly special.
It's unbelievable.
And so this eight year
old boy goes on to create
hundreds of millions of
dollars of value because he,
you know, understands this
early in his life and employs
hundreds of people and, and
changes countless lives.
And, you know, Ryan, as
you know, the reason I
know this kid's story so
well is because it's me.
Right.
I thought it was Willy
Wonka this whole time.
Are you serious?
No.
No.
Right.
I am well acquainted with
now and later the sweet
story of Will Schroeder.
Yeah.
Yeah.
Now and later.
Right.
And I like to tell that story.
You know, it's interesting,
but I want to mention this.
I told that story for the
first time at the, uh,
entrepreneurship class I teach
in my kids middle school.
And as it happens, my 13 year
old daughter, Summer, was in
the room when I told the story.
And that story goes on to
talk about, I had a very
bizarre origin story.
I went to college for a
year as a fake student.
I basically, you know, like,
every weird thing that you could
possibly do and all the things
you'd have to overcome, I did.
But Ryan, you know, I think
you'd appreciate this.
Afterward, uh, Summer
rode home with me.
And she's like real
quiet in the car.
And she's thinking, I can
tell like her, her, her
mind is spinning, right?
Finally, she's like, Dad,
I just have to tell you, I
had no idea what it took for
you to, to create the life
that you've created for us.
And I'm so incredibly thankful.
And I'm so proud of you.
Amazing to see that kind
of gratitude and maturity.
I gotta say, like, 40 years of
grinding was worth a few seconds
of that gratitude.
Isn't it funny?
Isn't it funny though, like,
what some of the actual payoffs
to entrepreneurship are?
Alright, of course there's the
obvious ones, like, if you made
money, that's great, right?
You bought a house,
that's great.
But there are so many
of these other beautiful
little nuanced moments.
Throughout our careers
that make all of this
stuff worth it, right?
From that first time a client
says yes to hearing your kid,
tell you how proud they are
that you clawed your way out of
nothingness and made something
out of it simply because you had
this magical realization that.
I can change the world.
I can choose my path, right?
I don't have to take
what was handed to me.
And that's really
what it's about, man.
It's about, you know, in this
case, you know, I'm literally
teaching kids, but it's about
those formative years when
the mold hasn't been set yet.
And we can take these kids
in any direction we want,
you know, from, from bad to
good, unfortunately, right?
Yeah.
But what rarely happens,
this is what I think is
fascinating, obviously what
we'll unpack, is what rarely
happens is somebody makes
such a big deal about teaching
kids The value of agency.
Yeah.
This idea that I can form the
world how I want it to be.
I don't have to take the
script that was given to me.
And then, of course,
the tools to do it.
And I think we should
talk about both.
I think we should talk
about what the sense of
agency actually means.
Yeah.
You know, and also why,
like, why it's not being
taught or, you know, how hard
it is for kids to get it.
But then, you know, let's
also talk about after that.
I want to get into What kind of
tools do kids need in order to
understand agency and be able to
kind of forge their own destiny?
Yeah, that's the
crux of it, right?
If we ask the question like,
so what is it about childhood
that drives that gear that
to go on and do these things?
How do we go from selling, you
know, candy in elementary school
to building startups as adults?
And it becomes fairly clear
that entrepreneurship begins
In that moment, when we
realize we can choose our
own path, even if we're only
a hungry eight year old kid.
But you know what's weird, Ryan?
We're usually not told.
Here's what we hear.
Usually not.
Are we ever?
Right, right.
It's usually one end of
the spectrum, which is
this amorphous claim,
you can be anything.
Yeah, yeah.
Which is totally untrue.
Which, yeah, that's, talk
about choice paradox, because
they didn't even have the
choice, you can be anything.
You mean any, any, anything?
Yeah, great.
Well, that helps me to
point myself nowhere.
There are so many things
that is not true, right?
Now, I know someone's going
to push back and say, oh,
you don't want to tell a
kid they can't be anything.
I'm not saying that.
I'm saying that what you
want to say is there are
some things that you can
become, but what's important
is that you make them happy.
Right?
They're a product of
your vision, of your
intent, of yourself.
Not, here was 12 options
and pick one and that's it.
Even worse in my case, I
remember taking that exam,
like that little test out
of freshman or sophomore
year of high school.
And it was like four
questions, right?
Like what could we possibly
derive from four questions?
But the, the, the things
that came out for me were,
uh, I should either be a
lawyer Or a forest ranger.
And so I thought, like,
well, I guess You would've
been a great forest ranger.
If environmental I
got the beard for it.
If environmental law had
been a thing, then maybe I
would've leaned that direction.
But, like, that
wasn't even an option.
It was like, do you want to be
a lawyer or a forest ranger?
I guess.
But back that up, man.
It started with, here
are preset scripts.
And you pick one, that's
it.
You pick it, right?
Doctor, lawyer, fireman,
policeman, right?
Like, that's it.
Those were the choices, right?
And there was no sense that
I had any choice really
in the matter outside of
like choosing one of those
things that were predefined.
And that even that was going
to be narrowed down based
on a couple of arbitrary
things like I like being
outside, ergo forest ranger.
And I have a good sense
of logic and language.
Ergo, lawyer.
Come
on!
How many more things can you
do with those skill sets?
But building that, it takes
time to be instantiated with
this idea of a preset script.
Yeah.
That's sort of the point.
By the time you've made it
through so many grades, assuming
you have, and you know, maybe
on to college and, and beyond,
um, and even in the workforce,
you have just been told over
and over, this is the path.
You show up, you complete this
work, you get this grade, you
get this payment, you get this,
uh, degree, and that's it.
That is life.
You just pick from a script.
And, and dude, that,
that goes back to what
we just talked about.
Like, this is exactly why
the seeds of entrepreneurship
grow during childhood.
Yep.
Because we haven't been far
enough down that path where, you
know, we've, all the curiosity's
been beaten out of us.
And we have not yet been
conditioned to believe that
this is just how it is, right?
Them's the breaks, kids.
These are your choices, right?
Off to the military for you.
To be fair, I'm not
saying it's for everybody.
I'm not saying 100
percent of kids should
learn entrepreneurship.
I was coaching my kids
hockey a couple days ago.
I'm standing next to one
of the parents of one of
the kids that I coach.
And the dad was saying, we
were talking about working at
startups, and he said, man,
that's the polar opposite.
Of what I'm bred to do.
He's like, I grew
up as an attorney.
I was a prosecutor.
And then the first chance I got,
I went to go work for Chase bank
because it was even more secure.
Yes.
He's like, I have no
risk appetite whatsoever.
So that guy should absolutely
not be an entrepreneur,
but, but hang on.
So entrepreneurship, not
for everybody, but agency.
The core of what we're actually
talking about here, everyone
should have agency, right?
That father had agency,
hopefully some level of
agency, chose the path
of becoming, right?
Became the prosecutor and
then said, Hey, I'm going
to use my agency to choose
to go and do something else
that I feel is better for me.
It's more secure, right?
That's agency.
Let's build on
that a little bit,
because I want to get into that.
When we talk about choice, Okay,
I can choose to do this or that.
Let's separate that, it might
be a little bit gray area, but
let's separate that from agency.
I'm gonna put choice as
in, here are my, here's
what's in front of me, and
I just get to pick one.
Agency is, there's nothing
in front of me because I'm
a blank canvas, and I'm
gonna create from scratch.
Yes.
What my world is going to be.
Right.
It's red pill, blue pill.
Screw you.
Right?
Like, I don't want pills.
Right?
I don't want to do my own thing.
Yep.
That's agency.
You bet.
I think that's a hard concept
to, to digest as we get older.
Yeah.
But what's interesting, it's
such an easy concept for kids.
We don't know what can't be.
We, we don't, we don't know.
We don't know that there's
a path we have to follow.
We don't know that there
are binary choices in life.
Right.
It's just that we, we
have that flexibility.
My son, he genuinely believes.
That he's gonna first play in
the NFL, uh, when he's done
with that, ironically, he's
going to become, um, a doctor.
Yeah.
Because he's, he said that,
that I'm gonna understand
injuries really well in the NFL.
Yeah, yes he will.
Yeah.
Yes
he will.
He'll suffer them himself.
And so,
my son will likely not do either
of those things, and I know it's
heresy for a parent to say that.
Yeah.
I just know my son well enough,
I, I, I know what his, his
skills and attributes are.
They're probably gonna
head in another direction,
who knows what that is.
Right?
Yeah.
But here's what I'm saying.
He doesn't know.
That he couldn't do that.
Yeah.
Right?
Like, he doesn't understand the
size requirement for the NFL.
Right?
And, and if he's a copy
of me, he won't make it.
Ha ha ha ha ha ha.
And so, my point is, it's
really interesting to me,
it's fascinating, That his
world is still a blank canvas.
Yeah.
My job, as a parent, I can't
speak to anybody else's job
as a parent, Is to keep that
canvas as open as possible, So
that he keeps asking, what if.
Right?
You know, help him with
direction, help him, you know,
find what he wants, but make
him keep asking questions.
Yes.
Versus shutting him down and
being like, no, this isn't it.
Now, here's what's interesting.
If I contrast that to my
daughter, who's 13, my daughter
has got it all figured out.
She has one plan and
there's no plan B.
Yeah.
She's 13 years old.
She wants to go to Harvard.
She wants to be a cardiologist.
That's it.
And she probably will.
And she probably, yeah,
she's like a perfect straight
A student, like whatever,
and she's smart as can be.
So, that's fine too.
My point is, uh, I'm there to
help them ask questions, I'm not
there to tell them what to do.
Not in that respect.
But I think, within this concept
of agency, Ryan, I think for
us, as parents The more we can
say, what if, or the more we
can say, what do you want to do,
or,
what don't you want to
do?
Yeah, yeah, 100%.
Those explorations
are the things that
matter the most, right?
I think that it's really
about stopping looking for,
like, these kind of hard
coded, discreet answers.
Again, like, where's
the path for me, right?
Do I need that?
And instead, just trying to
remain curious and asking
yourself, you know, letting
them ask themselves, why not?
And come to those conclusions.
The coolest thing about, you
know, our jobs here at startups.
com and what we get to do all
day is all we work with our
people with agency, right?
We almost forget for a second.
If you, if you, if you sat
here long enough, you'd forget
that the rest of the world
has regular jobs because
everyone that we work with
creating their stuff from
scratch, so at some point.
Each of these folks had to have
a moment where they realized
that agency could exist.
Yeah, yeah.
Right?
Where they realized that
maybe the path that life
had prescribed wasn't their
path, who'd have guessed, and
they could create a new one.
What's also interesting
about that, Ryan, I'm curious
your thoughts on this.
Once we understand that
the world is malleable, it
gets Really interesting.
Sure does.
When I was eight, that day
I discovered that life,
my life, is malleable.
Right?
The fact that I didn't have
parents, or I didn't have,
uh, income was a condition,
but it wasn't the answer.
Correct.
And it wasn't a
permanent condition.
Right!
And so, think of how powerful
it is, early on, if we show kids
How malleable the world can be.
Because the reality is
most kids grow up in a
shit situation, right?
We're in the most privileged
country in history in the U.
S. Ryan, you're in Guatemala.
You're not in the most
privileged country.
I'm in nearly the
opposite, yeah.
Right, right.
And you see every day how
hard coded folks lives
in environments feel.
Oh, there's a true
belief that there's no way
to transcend situation here.
Station.
Like, whatever you have,
wherever you started, is
where you're going to end up.
There are very, very
few breakout cases.
And people don't ever seem
to believe that they could
be one of those, right?
You see that it's hard coded.
It is what it is.
And it happens earlier.
You bet.
And there's a cultural
phenomenon that basically
said, look, things suck here.
Right.
And the best you can do
is make it suck less.
That is the polar
opposite of agency.
That is, you've been conditioned
that you are trapped.
And the truth is, if you're
conditioned, you know, it's
the, uh, the, the elephant with,
with the rope around its foot.
Right?
It just, it's always
had that shackle.
Yeah.
And so it feels like it
still can't go anywhere.
That is the worst thing
we can do to a kid.
Take away that hope.
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 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.
In my case, what we have
tried to do with our kids
is to consistently show them
how to take agency, right?
Not not necessarily just as
themselves, but even us as
adults, how that is a constant
and current process that
we're always, always going
through the choice to move to
Guatemala in the first place.
That was a choice that was us
exercising agency and saying,
we wanted to change something
about the situation in which
we were raising our kids.
And we wanted a
different environment.
We've been here six and a half
years and now we are saying
we want to change that again.
And here's why.
And, and there are tough lessons
that live within that, right?
Because to leave here,
there are sacrifices.
Yeah,
there are benefits
on the other side.
And so it's a matter of truly
exercising that agency in the
way that you just described,
which is asking why, staying
curious about things, and
really not having to say, like,
here's all the reasons why, no.
Or here's all the, just
the reasons why, yes.
Because that turns it back into
that binary, binary choice.
And instead, showing them how
malleable life is, and that
with some agency, that you can
try to make it what you want.
You can fail at it too.
And we've made some decisions
where they look at it and
they go, Why'd you do that?
And we're like, we thought
it would be different.
At its foundation, you have to
have this glimmer of optimism
of what's possible, right?
And I think that's so important.
When you take that out of
a child, when you take the
optimism or hope, okay, out of a
child, you forever neuter them.
Yep.
Right, from opportunity.
Now, there's a version of
parents that I get, which
they want to be protective.
I don't, I don't want to instill
this false hope in my child.
They'll never make
it to something.
Yeah.
I get it.
I get it.
Okay?
And I understand
where that comes from.
Who wouldn't want to, quote,
protect their children?
But you're also protecting
them from success.
Right?
You're also protecting
them from agency.
To be able to say,
my situation sucks.
Yeah.
I'm gonna do whatever it
takes to recreate my world.
To make it what I want now
some people will listen to
that and they'll say that's
bullshit Will you've just got
this false hope and it doesn't
work for everybody except one
thing We talked to hundreds
of thousands of entrepreneurs
who did exactly this.
Did
exactly this, yeah.
Right?
Doesn't
work for everyone.
Just works for
everyone we talk to.
Strange.
Yeah.
We're a little biased.
But what I'm saying is like, my
situation was fucked up, sure.
But it's a fraction of where
we see other people come from.
Sure.
Right?
People coming from, especially
from other countries, different
cultural environments, etc.
Dramatically more challenging.
Yep.
Fun fact.
As you know, I was
given a keynote.
at an entrepreneurship
conference last week.
And I told that eight
year old kid's story for
the first time in public.
And it was, it was interesting
to me because I, I, you know, I,
I'm not shy about my background.
Right.
I don't usually go up
and keynote about it.
And I, but I was telling
this, this story of agency.
But what was interesting was
afterward, a whole bunch of
people lined up to talk to me.
And I'm assuming they're
going to want to pitch ideas.
None of it.
I mean, a few.
Most people that came up
to me wanted to talk about
how they had the same
challenges as a child.
And they didn't know they
were allowed to talk about it.
They didn't know there
was a path forward.
First kid that comes
up to me, super smart.
He's like, both my
parents were murdered.
Right?
I mean, whoa, holy shit.
Wow.
Right?
Yeah.
And he explained the situation.
He was very open about it and
vulnerable, which I respected.
But he's like, I didn't
know I could talk about it.
I didn't know that
there was a path.
Now, he's at an
entrepreneurship conference.
So obviously, you know,
he's got an idea where
he wants to take it.
Another woman comes up
to me, probably 2021.
And, uh, she said that her
challenge was that she had
to be able to get off of
her reservation in order to
become an entrepreneur, right?
Like, um, you know, very
strong Indian culture.
And the idea of leaving the
reservation, of becoming
anything but, you know,
someone on the reservation,
not knocking that, by the way,
I'm just saying culturally,
was a big deal for her.
And, you know, that, that
defined her childhood,
that struggle, et cetera.
But I think what's
interesting is It also
accelerates you.
Well, I think there's something
magic that happens, man.
There's something
magic that happens.
It goes from being
when you take hardship.
And you add a little bit
of agency, realization of
agency, that hardship becomes
a foundation that you push
off of hardship of that same
sort without that realization
of agency becomes an anchor
that you just continue to
drag around with you, right?
It goes back.
It's the elephant
with the rope around.
It's like it doesn't
realize it's not there.
At some point, the elephant
that realize there's some
agency, Ties that rope into
a, into a, into a bow and
celebrates with it, right?
Like at some point it becomes
the thing that actually helps
you move forward instead of
the thing that holds you back.
And I think the difference there
is simply a dash of agency.
You know, what's interesting
too is for a lot of founders,
I think they say this with
like, like a bit of humility,
but I will say the reason
I'm a founder is cause I'm
totally unemployable, but
think about that for a second.
Had I not been able to, to,
to create my own path, I
would not have survived well
in a corporate environment,
in a lot of environments,
really, you just, you'd say
the same thing, but in a very
different context, you'd say.
I'm unemployed because
I'm unemployable.
Right.
Very different.
Right.
Again, like that, that
agency changed that
story.
I would never want to manage me.
Um, that, that would be my
greatest nightmare, but, but
my, my point is, I think for
a lot of, uh, entrepreneurs,
part of what drives them,
they want to create a
world on their own terms.
Yeah.
Let me be like specific
about what some of these,
these parameters are.
Some people look at it
like, Oh, I want to create
a business to make money.
Sure.
I get that.
But a lot of folks are saying.
I want to create a business
so I can travel all the time.
Yeah.
Right?
I can be nomadic.
Okay?
Other people saying, I want
to start a business because
for who I am, maybe the color
of my skin, or my gender,
or you know, whatever it is,
that I'm being persecuted
for what I'm trying to do.
So fuck all of you guys.
I'm going to go do my own thing.
I'm going to hire
whoever the hell I want.
I'm going to work with
whoever the hell I want.
I'm going to do whatever
the hell I want.
And they want to create
that agency for their life.
As well they should.
Yeah, yeah.
It's so important to, to you
and I, Ryan, to give people
not just the sense of agency,
but, but I want to transition
here, but the tools to do it.
It's one thing to say you
can be anything or you can
create your own world, blank
canvas, blah, blah, blah.
But if we don't give
you the actual tools to
do it, what good is it?
Ryan, when you think
about the tools that we're
teaching founders, and in
this case, let's say, uh,
teaching kids, and your
own kids for that matter.
Sure.
You know, what are
some of the tools that
matter the most to you?
I think some of it just
goes back to like that,
that hope and desire for
something different is okay.
Right.
That doesn't necessarily
feel like a tool unless
you don't have it.
And then all of a
sudden it sure does.
It feels like the shovel
that digs you out of the
landslides are covered in.
So I think that, you know,
it's the, if we go back to like
some of the tools, right, I
was the kid with the proverbial
lemonade stand, right?
Six, seven years old.
I didn't have a lemonade stand.
I had a lemonade wagon.
So mine was a slight deviation
from the normal model, but
that's because you were the, uh,
you're the original food truck.
I quite literally, man, because
we lived in a developing
neighborhood and we lived
at the end of a cul de sac.
Nobody was going by my house.
I couldn't set up a
lemonade stand, right?
And the rents at all my friend's
driveways were way too high.
So I grabbed the radio flyer
wagon and igloo cooler that
my dad had for softball
practice that he coached.
And I filled the damn
thing with lemonade, right?
Started hauling it around.
Selling it to the
construction workers who
were, who were working on
the, the various lot sites.
Uh, and so like, I learned
a lot of lessons or a lot of
tools that came out of that.
But I think one of the biggest
tools wasn't, it wasn't
the money that I earned
that bought me a super,
super sweet ET bicycle.
Uh, it wasn't that
it was the knowledge.
That I could create something
from nothing you bet right
that I could I could do that
right and so it was these the
early learnings that propel
you into so I'd be like the
the tools are really being open
to trying, right, especially
in an age where you're still
relatively fearless, you're
afraid of certain things, but
you're not afraid of failure,
right, don't care about.
Yeah.
Less
consequence.
Look, I think the, the mindset
shifts are, are perhaps the
most important tools to me.
It's mostly going to come back
to like the mental models that
all of a sudden you realize,
especially the ones you've been
handed, even at a young age are
largely broken and don't have
to see everything through that
lens that you've been handed.
So casting away the lens was
probably the biggest tool
that I developed at that age.
When I sold that first
pack of Now and Laters,
unwillingly, that was the tool.
I realized that if I had a
product that someone wanted,
I could sell it for more
than I paid for it, right?
Now, while that sounds
dead obvious now, it was
not to 8 year old me.
I did it by accident.
But I caught on quickly.
Yeah.
Right.
That's the thing.
But you do, right?
Like I, it's funny now
that I'm thinking about it.
One of my, one of my
lessons at that same stage
was agency with an agency.
Right.
So I had the agency to go in and
to, to create the lemonade wagon
after a couple of days, this
thing happened where some of the
guys weren't buying it anymore.
And I could have just accepted
that like, they're not
thirsty and want, but I took
agency within that situation.
I wouldn't ask like,
Hey man, you, you, you
bought from me yesterday.
You haven't bought
for a couple of days.
And he said, yeah,
you know, your, your
lemonade's a little sweet.
I like it a little, I like
it a little more sour.
I'm like, okay.
Heard feedback similar to that
from a couple other people.
Asked my dad if he could
take the, the, the, the 15
bucks I'd made so far and
go buy me another igloo.
Bought me another
cooler next day.
Mixed up the, mixed up
the sour batch, right?
Less sugar.
So you, so,
building at the rent,
the tool you learned
was customer discovery.
Yeah, exactly.
These are the tools I'm
talking about, right?
These are the fundamental
utility belt of a founder.
One is opportunity, one
is finding profit, one
is customer discovery.
The other was you realized
that in order to get more
customers, you had to go get
them versus them come to you.
And here's what's fascinating
about all these tools.
You only need to
learn them once.
Yeah, yeah.
Right?
You only need to
learn them once.
To some degree, I am
still always a seven year
old kid pulling around a
wagon full of lemonade.
I'll give you a funny story.
Uh, I might have told you this
once before, but, um, my old
business partner, uh, Blaine
Walter, they tell this story
about, uh, the CD player.
Yes.
Right.
So, so, uh, for folks
in the audience that
haven't heard this one.
Great story.
So my old business partner,
um, when I ran the agency, uh,
his dad had started a Cardinal
health, you know, which is one
of the, uh, I think it's like 15
largest country company started
as a little grocery store.
It did in Columbus, Ohio.
Uh, anyway, uh, he's, he's
the son of the founder.
He told me this great story
about him and his brother
and his brother is like, I'm
going to say 12 years old and
he wants to buy a CD Walkman.
So you got to figure this is
like late eighties, right?
And his dad, who's one of
the most stoic CEOs, right?
I've only met his dad
maybe a half dozen times.
And when Bob Walter looks
at you, he doesn't look at
you, he looks through you.
And what I mean is his level
of intensity is unbelievable.
A brilliant man,
a brilliant man.
But his intensity
even scares me.
Okay, and I'm not even his kid.
Anyway, here, but this is such
a dad entrepreneur thing to do.
So he says to the
older, uh, brother.
He said, look, I'll give
you the rest of the money.
I'll advance you
on your allowance.
But if you don't pay it back
with interest, how awesome
is that with interest?
Okay.
I'm going to
repossess it from you.
So no surprise, a month
goes by, falls behind in his
payments on his allowance.
And dad being the CEO
and founder that he is
repossesses the disband,
but that wasn't enough.
The important lesson was that
he sold it back to Blaine
for 50 cents on the dollar.
Right.
And Blaine was like, I never,
I never needed to learn a
lesson about debt ever again.
That was it.
How amazing is that story?
Will, is that the origin
story for Afford It?
Is that where you decided
to sell electronics
on weekly payments?
Right, I wish, I wish.
And so, but what I'm saying is
like, these little lessons that
seem, you know, trite at the
time, are incredibly powerful
and they form this tool belt
that most kids don't have.
Most kids don't understand what
the tools would be to be able to
identify a problem and solve it.
When we do this entrepreneurship
class, again, this is middle
school, the first thing we do,
uh, is we open up, uh, the,
the, the class is designed
to build a pitch deck and
at the end pitch it shark
tank style to a bunch of
founders and the kids love it.
But the first thing we do,
first day, um, this is actually
tomorrow, is we talk about,
um, identifying problems.
And I always tell them, I
said, all of you are worried
that you don't have an
idea for a company, but you
all have ideas right now
because you all got problems.
I give them the tool, I teach
them the tool, that every
problem is an opportunity.
That all products
come from a problem.
And we map back to, you know,
every product in their life
started with somebody's problem.
Now they have that tool.
Now instead of saying, oh, I
haven't invented something,
as if the invention.
They have this new tool that
says, wait a minute, I need
to look for problems, and
problems are everywhere.
And a lot of those problems
affect me, personally,
which make them very good
problems for me to solve.
Now they have that tool and this
series of tools, uh, problem
identification, trying to
figure out how to make a profit,
sourcing things, selling things.
Once you have those tools
early on, all of a sudden the
world gets very interesting.
I remember one of the lessons
that I took from that then
was that where you apply those
tools starts to matter a lot.
Cause I went on to like do
a bunch of other things to
make money from an early age.
I realized like, okay,
this is interesting.
I can go solve people's
problems and make money.
Then I realized at some point,
not all problems are worth
solving because it's not
just about the money, right?
You start to understand
like, okay, I could go
do this, but I'd rather
spend my time doing that.
And so that not all problems,
I think it was one of those
fun realizations for me was
just because I could spot
something as an opportunity.
i.
e.
I saw a problem, understood
that it was worth solving
from a monetary standpoint,
found the solution and
could get paid for it.
That wasn't actually the
pinnacle of the exercise.
All right.
That making sure that it was
something that I love doing.
Like we, we joke around
all the time, right?
Like, you know, if, if
we had built lawyers.
com into the startups.
com, I wouldn't have nearly
as much fun with what I do.
Nothing against
lawyers, except yeah.
Something against lawyers.
Yeah.
Yeah.
Yeah.
We need less of you, but we're
about to have less of you.
But, but that said, that
said, I think about all of the
tools, just like you described,
Ryan, that I developed as
a kid and how by developing
as a kid, they also made me
more advanced as an adult.
A while back, one of my
friends, uh, we were kind
of going deep on this.
And he said to me, how do
you think you learned sales?
He said, you're, you're, you're
a very charismatic salesperson.
Like you're very good
at communicating what's
important to you, et cetera.
And I said, the way
I got good at it.
was because I was
forced to listen.
And what that meant was, and
this is, and it kind of ties
into the story almost exactly,
when I said I'd have to run
around to figure out, you know,
where I was gonna eat dinner
tonight, it was a sales pitch to
that kid's mom that I was worthy
of, of having dinner there.
And honestly, It was
the 80s, people weren't
that, like, cool, right?
Like, they were fine with
telling you to fuck off.
And so, I would have to
basically charm the mom or dad
for a brief period of time.
But to do that, I had to listen.
Which kids don't
necessarily have to do.
But I had to listen as
to what was important
to them, you know, etc.
So that I could know to say
the right things, right?
And not come across
like an asshole.
That's sales!
Right.
Literally the
foundation of sales.
Now it came from a bit
of a fucked up place,
but I didn't need
to learn it again.
Oh, and again, it came from
a fucked up place, but that
little bit of agency that
you discovered along the way,
turn that into a powerful
tool instead of something
that was going to hold you
back in the future, right?
I think it's, it's so important.
We get into a point.
Okay.
Listen, now I've got
this tool called sales.
Yeah.
Okay.
Maybe one of the most
powerful tools you can have
as a founder.
What are we not selling?
We're selling people on the
idea of the work for us.
We're selling people on the
idea to buy our product.
We're selling investors
on giving us money.
We're selling all the time.
Constantly
in a lot of people.
And I say this in a good way.
Have never had to sell?
Because there was never a
consequence if they didn't.
You could say, well, I
tried to talk my parents
into getting me a Nintendo.
And if you didn't, you'd
be disappointed, but
you were fed, right?
So, like, the stakes
weren't that high, okay?
Now, uh, when I say that,
when you've been conditioned
to sell for a long time,
you just naturally do things
that most people don't do.
I would put
listening at the top.
If I'm a good salesperson, it's
because I'm a good listener.
And it's important to me
to make sure the other
person is happy, right?
Versus, let me just tell
you why I want something.
Right.
A good salesperson says,
I'm going to come from a
position of knowing why you
want something, and then
working backward from there.
Yeah.
But once you figure that
out, you can apply it
to a thousand things.
I would go around,
around this time.
I loved building forts, which
obviously also had an early
path, but I love building forts.
I think, I think you've
actually in this, in the
course of this call, you have
completed the, uh, the 10 by
10 grid of 80s child bingo.
And
anyway, so.
But one of my things
would, would be, I'd come
up with like, a plan for
what this fort would be.
And then I would go recruit all
the kids in the neighborhood.
And if you grew up with
me, you know exactly this.
We're always recruiting, right?
It's like a startup.
Selling the vision of what
this thing could be, explaining
why you're gonna work for
sweat equity to do this.
And then convincing everybody
at the same time to show
up at the same place and
work under a shared vision.
And I loved it.
I loved it, right?
And, and we always had these
cool forts and these cool
situations that would have
never existed had someone
not pulled this all together.
But all of those things I
was learning, especially the
recruiting and things like
that, here's why I think you
should come and carry all
this plywood from, away from a
construction site in the middle
of the night so that we can go
build a fort with it, right?
Here's why it'll benefit you.
But what's great about
teaching and learning those
things, um, at that age is
that there Easy to learn.
Yeah.
Because you don't know
why you wouldn't do it.
Right.
Right.
What's amazing about
that, despite being easy
to learn at that age, the
transferability and value of
those skills as we age just
increase over time, right?
It just becomes more
and more valuable.
We get to exercise
them on bigger and
bigger stakes outcomes.
And it's interesting because a
lot of people never had to sell.
I'll give an example.
So my daughter, she's smartest
can be, but she doesn't
have to sell anything.
Now, to be fair, in a couple of
instances, I think I told you
this when she wanted a puppy,
my, this is like a few years
ago, my daughter went and made
like the most comprehensive
PowerPoint presentation
with slides in fact,
this become a thing
because, because I get
pitched PowerPoints by
my kids all the time.
It's hysterical, but
like who started this?
Like, it wasn't like, I was
like, what you're going to need
to use to build a presentation.
They figured it out.
Right?
It's a thing.
And so, uh, she, Summer, my
daughter, uh, pulls my wife and
I, uh, into the living room.
And she's kinda nervous.
She is nervous, right?
A lot, a lot, a lot
on the line here.
A lot lot at stake.
But, she's all business, okay?
And she, uh, she, she opens up
her presentation, and to her
credit, it was very well done.
As a dad, you know, as a parent,
like, this was such a moment.
I was like, I, I, I
thought two things.
This is one of the
coolest things ever.
And there's no way your mom's
going to let you get a puppy,
no matter what's on here, right?
Anyway, so she gives the
presentation and she has
like facts and figures.
And she's like, and did you
know that one in four, uh, four
puppies actually don't shed?
She's already thinking about
what my wife's, uh, you know,
objections are going to be.
Controls heart rate
and blood pressure.
It
was, it was amazing.
Now, the reason I bring that
up is because, not because
she's a great salesperson.
I bring it up because the
whole presentation was
clearly designed to, to
think through our objections.
It wasn't about what she wanted.
It was about what we wanted.
And that's what
made it effective.
Learning what triggers
work, like, and kids
are amazing at this.
I mean, like, there is a
natural gear that kids have too.
And it goes back to something
we talked about before, which
is like wanting to have some
control over part of life.
This is quite literally
what childhood is about.
It's about pushing the
boundaries so you understand
where they exist, which ones
are flexible, which ones
aren't, and trying to have some
control over your environment.
And this is what
childhood is about.
Watching them navigate it
is a masterclass in how to
experiment, how to learn.
And how to accelerate the
learnings and how to leverage
the learnings into the things
that you want to get, right?
It's absolutely amazing.
My son's only eight and
he doesn't have this gear.
He is incredibly charming.
He's going to make a
phenomenal salesperson.
Right?
However, he's still eight
and he's also very selfish.
So he'll come to me crying
and he'll be like, Mommy won't
give me something, right?
And I was, and, and, and
I prod him a little bit.
I'm like, well, uh, what
did you say that made
mommy want to do it?
He's like, what do you mean?
I was like, well, you
told her what you wanted.
You give her a list.
What does she want?
Yeah,
right.
And he's like, huh,
but again, you could
see the wheels turning.
And the next time he goes back,
he'll open with, Hey, mom,
here's, here's why I think
this would be good for you.
So the next time he goes back,
he's going to be like, Hey,
mom, you know, here's why I
think this is good for you.
Once he figures that out, once
he, you know, kind of dials
in that tool, he's dangerous.
Yeah, right.
That goes everywhere.
They learn what works.
Like, yeah, my seven year
old Jack has learned that
with me, it's often an
emotional sale, right?
Like when he appeals to that,
like when he wanted peacocks,
which we have now, as you know,
whether we want them or not,
how did he appeal to me?
He appealed to me by telling me
he believed that I could do it.
I told him, I don't know
if I could find this.
Like I'm, I'm just bullshit.
And I'm like, I know, I know
exactly where to get them.
Like, I don't know if I
could, you know, I don't
know if they have them here.
I don't know if they
survive in Guatemala.
And he's like, anybody
could do it, dad, it
would be you nailed it.
And so now I'm not
bidding against him.
I'm bidding against myself.
I'm like, no, I really, I
don't think I could do that.
And I, you're, you're
probably wrong.
And I'm not as good
as you think I am.
Like,
you got me.
It's amazing.
And to his credit, he was right.
I did it.
And they're lovely
creatures here.
I know the ones that live
next to you, not so much fun.
Yeah.
Mine are my neighbors.
My neighbors has, has like 300
animals on a two acre property.
So what, what's
interesting to me though,
Ryan, it took a
second to process.
I already knew that fact.
But like, hearing it
out loud exactly like it
sounds and made, made it,
made it, it funny again,
what's interesting to
me is as we teach these
tools, as we plant these
seeds, they keep growing.
Yeah.
Right?
And they become these,
these phenomenal things.
A hundred percent.
But if we don't plant the
seeds, right, we get nothing.
We harvest nothing.
If we don't plant the
seeds, we get nothing.
Right.
At all.
In fact, what ends up
happening is that we actually
end up making it so that
the seeds get harder and
harder to plant every year.
Every year that we restrain
agency, every year that we don't
teach the tools, we put our
kids, we put all kids in this
position to have less agency
in the world, to have less
tools to do what they want.
So if we want to do something
that's more important than
anything, as founders, as
parents, it's to give every kid
every bit of agency we possibly
can, every tool we possibly
can, and keep pushing them to
get out there to do their own
thing on their own terms, and
let them be who they're suppo
Overthinking your startup
because you're going it alone?
You don't have to.
And honestly, you shouldn't.
Because instead, you can
learn directly from peers
who've been in your shoes.
Connect with bootstrap founders
and the advisors helping
them win in the startups.
com community.
Check out the startups.
com community at www.
startups.
com to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.