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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 the episode of
the Startup Therapy Podcast.
This is Ryan Rutan
joint, as always by my
friend, the founder,
and CEO of startups.com.
Will, Schroeder will, we are
300 episodes in and we are
still staring down one of
those same questions that
every founder faces early
on, like, how do you lead?
How do you do confidently?
You've never done any
of this shit before.
Yep.
Right.
Today, I think it would be fun
is like, let's go back in time.
Right.
You started your thing at 19.
I was right around
that same spot.
Yep.
You were terrified to call
yourself a CEO and a founder.
I didn't even know I should
call my, I think I called
myself a president because
I think that was the only
title I knew at the time.
Right.
That thing.
Yeah.
Yeah.
Yeah.
I was like, oh, that sounds
like the, the, the guy, right.
Uhhuh.
So let's, let's unpack a
little bit of the blueprint
that you use to turn that
just raw uncertainty into
rock solid confidence.
Because like one of those
things that like everybody
believes is like, some people
are just born with it, right?
Right, right.
Or maybe it's Maybelline, right?
No, it's, it's a
practice skill, right?
We get there.
It's like, look, go back
to the early podcasts,
300 podcasts later.
You and I are super
confident to do this because
we've done it 300 times.
First couple episodes we were
anything but they're terrible.
I hated the sound of my voice.
We wouldn't record video
'cause we hated what we
looked like on video.
Like, it was like,
it was so bad.
Right now we don't give a shit.
Yep.
If I were to look at this and,
and I was talking to a founder,
uh, last week, this is usually
where these episodes come from.
It's, you know, we interact with
lots of founders and we hear
things and we were like, oh,
we should unpack that a bit.
And I was talking to a
founder and she was saying
she's like, like kinda like,
like kinda mid thirties.
So she's been at this
for a little bit.
Right.
You know, not like fresh
outta college kinda thing.
And she was like.
I'm just starting to
get my, my confidence.
She's like, but, but you've
always, you know, for as long
as I've known you, you've
always been confident, right?
Like, like that's 'cause I was
already 40 when you met me.
You've always been old.
But like she said, how
did you get that way?
And I was like, well, I
didn't start that way.
That's the part that I
think is, is more like myth.
Yeah.
'cause I felt that, I saw that
myth like when I was starting at
19, Ryan, here's what I thought.
I thought there were some
Oompa lump of factory of
confident people where they
just stamped these people
out and they became the cover
models of Forbes, right?
Like right.
They just gave you gray hair
and they just like made you
the president of BCO and
you just had confidence.
And I didn't know
where it came from.
I didn't know how it was
developed, and I just knew
that I didn't have it.
Now what's interesting is.
You know, I was 19 so I wasn't
even around long enough to
know where you would get it.
Like I had just
shown up to the game.
But the other side of that was
interesting was I also happened
to pick a career that was
startups, which was easily the
biggest cauldron of insecurity
you can possibly jump into.
Yeah.
And I think it
compounds and Right.
When you talk to, when you
talk to other founders,
how often do you meet
fully confident founders?
Very rarely.
I think in a lot of cases when
I do run into the very confident
and early stage, the ones that
look very confident, I think we
gotta draw a line between like
confidence in hubris, right?
There's a difference
between, between just, I
have plenty of that thinking,
you know, everything and
actually knowing everything.
Yeah.
But I think that, you know,
I think this is, and this is
probably a kind of a macro
point to this entire episode.
Which is, there's a
difference between confidence
and certainty, right?
I think that as founders,
one of the things that
we're trying to say is like,
well, I'm not confident
because I'm not certain.
Gotta separate those
two things, right?
Because that person that
you see who's just got that
self inflated confidence
and it's not, not real yet.
That's not from
certainty, right?
Right.
It's just uncertainty,
well masked.
And if you're trying
to predicate your.
Certainty or your
confidence uncertainty.
This is where it starts
to go wrong, right?
This is why we're like,
well, I just really don't
know, so therefore I can't
come off confidently.
Well, that's not where
it comes from, right?
It comes from trying and
failing and doing it.
All this stuff we're
gonna talk about today.
Um, there's a roadmap.
To answer your question very
briefly, very few of the ones
who I think are actually gonna
go anywhere, start off with
a lot of confidence, right?
They start off doing something
else.
I agree.
So when I was first starting,
I had zero confidence.
I'm 19 years old, I'm going
to start an internet company.
When nobody had ever heard
what the internet was, I
was a horrible student.
And I, and I only say that,
not that that's totally
relevant, but I didn't
have like the benefit of
also being a star academic.
Right?
So like some people, they come
into the world and they're
really good at something.
Like our oldest daughters, for
example, are just like geniuses.
Yes.
Like they're just stacking up
as on everything that they do.
Everything, which is
the repetition talent
across the board, right?
Which is the repetition
that builds competence.
I had none of that.
I graduated bottom of
my class in high school.
I got rejected from every
college I applied to.
Like things weren't going well.
Like there were not a lot
of confidence builders
going on in my life.
And so I assumed that,
like I said, that there
were people who were.
Born confident, those people
became the confident people
like, like there's people
that were born good looking
right and that that's just it.
Okay.
And that confidence
was just something guys
like me didn't have.
What I didn't understand was
that's not the way it works.
It's like building muscle.
Yes, some people are just
bigger than others, but
generally it takes lots
and lots of repetition.
Lots of dedication to build
that muscle that is confidence.
And so again, let's talk about
the actual roadmap to do it.
Yeah.
And I think for people who,
you know, have developed
some confidence and some
experience that usually
those go hand in hand.
They'll appreciate what some
of these categories are.
And I think for people that
are early in their career,
just, you know, kinda lack
confidence, they're dying to
know where these categories are.
Like, just point me in the
direction of confidence.
Show me how to do this.
So, uh, where
should we start?
When I said before the,
the, the founders that I
talked to, I believe are
going somewhere, they don't
start with competence, they
start with something else.
And to me, I think one
of the key ingredients to
developing cur uh, competence
over time is curiosity.
Right?
Curiosity leads.
To confidence, right?
And it starts with the level
of confidence to be curious
in the first place, right?
It takes some level of
confidence to be curious
to ask the question.
'cause I think a lot of
people associate asking
with, with weakness and
it's just not right.
Asking is not weakness.
Asking is
power's
actually authority?
Yeah.
Yeah.
It's power.
It's how you do it, right?
Like I had this thing.
Early on when I was first
getting started, where I didn't
realize it was like a superpower
because I just, again, I
exactly what you just said,
I associated asking questions
with, you don't know and you're
stupid, or you know, whatever.
Right.
But at some point I got so good
at asking questions, I. That
it put me in the power position
when I walked into a room.
Here's how it worked out.
Percent.
I'm 19 years old.
I've still got pimples
from high school, right?
Like I, I, I do not look like
someone with authority at all.
And I was not fitting
suit briefcase
with nothing in it.
Very exactly.
My very ill-fitting
suit, my empty briefcase.
Like I was, it is, it is gross.
And, and at a time when young
CEOs didn't exist, so like
nobody was giving me credit that
you might be Mark Zuckerberg.
I didn't think he was born yet.
I walk into a room.
And what came across
as natural curiosity.
When I would talk to
clients, I would say, well,
what does work for you?
Right?
Because I didn't know, I
actually had no idea how
their business worked, right?
So I would just ask, so,
so what does work for you?
And they would say, well, you
know, um, we sell really good
to this constituent really
well with this constituency or
this, this, um, demographic.
I remember I didn't know
what that word meant.
And, and I'd be like,
so what does the
demographic mean to you?
Literally ask you.
Yeah, that's it.
Explain to me, in the middle of
a meeting, and I'm a marketing
company, define this to me.
Yeah.
How do you define demographic?
It turned out that when
I was asking questions,
I had the room.
In the same way, a prosecutor
in a courtroom asking the
questions has all the power.
Yeah.
Because when someone's asking
you a question, it puts you on
the defensive in a strange way.
Right?
Not that they, they're trying
to, but it puts you in a
position where you're the
one demanding an answer.
You get to steer you.
You have the helm at that point.
And that's one thing where
it kind of gives you a little
bit of power and that that's
great, but more importantly,
you're learning, right?
You find out what a demographic
is, you find out that's pretty
important when you're gonna
start a marketing agency.
And when you get really good,
just naturally at asking
questions of everything,
of everything, dude.
In other words like, Hey client,
how does your business work?
Hey, employee, why is it
that you do things that way?
Hey, advisor, how is it that
you got to this outcome and
how would I do the same?
Peppering everybody?
And by the way, Ryan,
it's exactly what
I'm doing right now.
Yeah.
As you know, I I, to
this day specifically.
With building this house.
You know, as some of our
listeners know, I'm been in the
process of building a house.
I knew nothing about how
to build a house, right?
Nothing about how to build
a house doesn't matter.
But I re I've always wanted
to build one that's been
a, a huge passion of mine.
But exactly this skill is what
gave me the confidence to do it.
So I was like, I wanna
design the house.
I want to, um.
Build everything
inside the house.
And by the way, I don't know how
to build any of these things.
So I wanna become an architect,
a general contractor.
I wanna become a cabinet
maker, I wanna become
an electrician, I wanna
become a network installer.
I want like all of those
things, and I wanna do them
at the same level or better
as the people who do them.
Yeah.
And I put on the scope of.
An office building and the way
I did it, I would get involved
with these trades and I would
say, well, what about this?
Well, what about this?
Well, what about this?
And they're like, damn, this
dude asks a lot of questions.
That's how I learned.
I. Cabinet.
Cabinet guy would come to me
and say, Hey, this cabinet's
gonna, this kitchen's gonna
cost a hundred thousand
dollars to making a number.
Right?
And I'd say, why?
He's like, what do you mean why?
Like literally line by line.
What are all the costs that are
involved in getting it to there?
Yeah.
And he's like, well, you
know, you, you have to
use this material and
this material and that.
And I'm like, well, why do
you have to use that material?
Couldn't you use another one?
Annoying as fuck.
Right.
But.
That's what made me confident.
Yeah.
Because you can ask
as many questions
as you want.
A couple things, when I went
back to like, especially
the early days, right?
When I was back in that
lacking confidence space, one
of the things that occurred
to me was that I didn't feel
comfortable asking questions.
Right?
And then I started to
look at the type of
questions I was asking.
Well, I think part of it was
this, like illustrating that
I don't know what I'm doing.
Right.
It was that the whole thing
of like, I dunno what the
word demographic means.
I don't want to ask
that question right now.
And then I looked at the way
I would've asked the question.
So the way the question
has sort of appeared in
my mind that kept me from
asking in the first place.
Okay.
And a lot of times it was
the what questions, right?
What do you mean the why
questions on the end?
If you just reframe it as
why, like what is demographic?
That's a problem, right?
If you're about to hire somebody
who probably should know the
answer to that, but if you
ask like, to your point, why,
why is this important to you?
Sure.
Why does this matter?
Why do you feel like this
is the key thing for what
we're doing right now?
Right?
All of a sudden it goes from
being somebody who you're
like, oh, they don't know
what they're talking about
to, Ooh, insightful question.
With a couple of
words changed, right?
Yep.
So a big part of this, I
think, for if you're, if you're
still in that position where
you're struggling to feel
confident enough to even ask
the question, ask yourself, are
you asking the right questions?
Are you wording the
question correctly?
Because simply rewording the
question, reframing the question
in so many cases, takes you
from sounding like somebody
who has no idea what they're
talking about, to somebody who's
sitting in a position where
they can ask down upon the ye
of little knowledge, right?
Where it's like, right, right.
Well, why would
you do it that way?
Right?
All of a sudden that
contractor's like,
they don't know.
They don't know
that you don't know.
What they know is that you're,
they're being questioned
about their methodology.
They're being questioned
about how they're going
to approach something.
Right.
They have no idea what your
reference level of knowledge is.
Also, people love to talk
about themselves, right?
They
sure, as should do.
That's
the ninja move there, right?
Like when I was single
and I'd go on dates
again, naturally curious.
I would just ask my dad a
million questions, right?
Yeah.
And she would come away from
the date being like, wow, like,
Will's a super engaging, like,
you know, interesting guy.
Yeah.
'cause we just talked about you
the whole time, which was fine.
You the whole time, right?
That's, that, that
was my preference.
Right.
I know nothing
about him, but yeah, literally,
I, like, I would remember I'd,
I'd come back from dates and
I'd think to my, I, I laugh
to myself like, this girl
actually has, knows nothing
about me, nothing about it.
Didn't ask a single person.
You might remember my name,
but I literally like, like
her relationship with her dad
and everything else like that.
Yeah.
I have an FBI level
dossier on her.
Yeah.
But I think it's a superpower.
There's nothing unique about it.
Either use it or you don't.
Yeah, that, and that's the
thing, like it isn't it, it
is also not a complicated
superpower, right?
It's not like the ability
to do complex mathematical
calculations in your head.
Anybody can ask a question.
Yep.
Anybody can ask a question.
And again, like there
are some probably higher
level formulations of
certain questions kind of
doesn't matter at the end.
As long as you're asking,
you're probably learning.
Let me ask you this
though, at at what point.
Maybe this is more of an
internal thing, so like,
because one of the places
I like to ask a lot of
questions is internally, right?
With within the team, right?
Yeah.
As you're starting to
lead a hundred percent.
Right.
This isn't all just
outward facing stuff.
As you get to the internal,
we're trying to lead the teams.
We're trying to be confident
in that leadership.
At what point do you feel
like you cross the line
from learning and growing
into slowing things down?
Right at, at some point, like
if you just keep asking your
contractors questions at the
house, they're not building
anything because they're
just, you're just asking.
Yeah.
Yeah.
Like how do you balance
those two things?
There's a limit.
To how many questions that
are even reasonable, right?
Like, and if you think about
it like this, if we were to,
we were to stack rank value,
not if you're 7-year-old
son.
No sir, absolutely not.
He knows no boundary.
It's
insane If you stack rank the
value of questions, and let's
say I've got 10 questions.
The first three questions I,
I'm gonna ask have 70% of the
value of what I need to know,
and the rest I may not need.
Right.
So I always think about it like,
let me get the fir the first big
ones outta the way and see if
the other ones are necessary.
Oh, on occasion though, I
don't know if you find this,
but on occasion though, the
thing, I think like the top
three there ends up coming out
like some nuance in the answer
that end up being, that's
what I'm saying, being like
absolute gold somewhere like,
not even within the top three,
but like somewhere where like
becomes a follow on question,
uh, in interviews.
When you're interviewing people,
most people aren't naturally
curious or, or empathetic.
I'm paraphrasing.
They generally don't give
a shit about other humans.
So when they interview, they're
really bad at interviewing.
They don't pick up
on social signals.
They, they don't understand
how to like double click
to the the why behind that.
I'll give an example.
Years ago I stumbled upon my
favorite interview question
because I was naturally curious.
Uh Right.
I had heard a couple of
previous interview people,
these were developers
back in the day, right?
Kind of bitching about
their current companies.
And I thought to myself like,
man, the person I wanna hire
probably isn't the person
that's gonna like sit around
bitching about my company.
Instead of like the generic
interview question, which was
something along the lines of,
you know, where do you wanna
be in 10 years, kind of thing.
I would ask the question,
what did you dislike about
your current job that you
would never want to do again?
Open up the door, open up the
flood gates to complaints.
Oh yeah.
Now, now, right.
And then, and then listen
to them to recite the job
description to you, and
you're like, okay, yeah.
Pass.
I never wanna work with people.
I don't wanna work
with annoying bosses.
I'm like, ah, you're not gonna
work out here well at all.
Yep.
What's interesting is
the value of where you
can go with questions.
Yeah.
What it allows you to
do as it relates to
building your confidence.
Once you know that you can
ask questions, it allows you
to go into any situation.
And be armed and ready, right?
Yep.
So I can go into like, again,
giant house that I'm building
and be like, Hey, I don't
know anything about how, you
know, plumbing works, right?
But I'm about to, uh, yeah.
And I, and I know because
I know I'm good at
investigation and questions.
Uh, that I can make that
work when I do meetings with
people, just like, you know,
meetings with random people
that I've never met before.
We're doing a lunch or
dinner, you know, whatever
the occasion calls for.
I know I'm gonna ask them a
thousand questions, and so
I'm never nervous walking
into a meeting, even if I
have no idea who this person
is or what the background is.
Sure.
Because I've got the
arsenal, the tool belt.
To learn everything
I need to know on the
spot when I get there.
Exactly.
Yep.
I think it's powerful.
Um, and it built a huge
amount of confidence for me.
Alright, so
curiosity, superpower
questions, super tool.
Yep.
This is how we begin to
build that confidence.
So as we start to grow that
confidence, so now we're,
we're learning some stuff.
Let's talk about what happens
when we actually start to,
to do some things right.
Because there's, there's,
we start at that point where
it's like, okay, I don't know
how, I don't know anything.
Right.
And then there's the, I'll
figure it out moment, and then
you start asking the questions.
You start learning.
But then there comes a point
where it's like the, okay, I
didn't know how, I do know how
now, but I haven't done it yet.
So then we gotta get to
that part where, okay,
I'll figure it out.
I'm gonna go try it.
Yep.
I'm willing to make the attempt.
I don't think a lot of people
understand that confidence, like
we said earlier in the episode.
Is a conditioning exercise.
I mean, you get something,
you're constantly
conditioning that muscle.
We look at it like this
confidence is a destination
a mile from here, and I just
don't know how to walk a mile
or you know, get a mile, right?
Like, no you don't.
Right, you will someday if you
start with walking 10 feet.
And tomorrow you walk
11 feet and the next day
you walk 12 feet and you
just keep chipping away.
Exactly.
And what that looks like here,
and I didn't know this at the
time, I certainly know it now,
and watch countless founders
through the same journey.
It's all these little wins
where you challenged yourself
to do something that you
didn't think you could do.
Lemme give you an example.
Yes.
So I'll, I'll stick with
with me early in the agency
days because that was
just younger part of me.
I remember like one of the.
Earliest meetings I was in.
This will give you this, give
you sense for how old we are.
The, the client said to
me, there's this new thing,
hold, hold, hold your hat.
There's this new thing called
e-commerce, and I remember, I,
I remember he emphasized the e
be because it wasn't commerce.
Now, Ryan possibly mean,
it was called e-commerce.
And I was like, eCommerce, do
you mean electronic commerce?
He's like, yes, we want
electronic commerce.
I mean.
I'm, I can't even make this up.
Like it was this stupid,
but again, it all
that starts somewhere.
So he is basically said, I
wanna sell shit on the internet.
But at the time, no one was
selling stuff on the internet.
Like, no idea.
Like it really wasn't
a thing, right?
This is like 94, like, you
know, people would start, but
this was early and I certainly
had no idea, no idea, right?
Um, had to sell something on
the internet, but I remember
the context of the meeting.
This client was so excited.
That they wanted to do
e-commerce, that I was excited.
And when they asked if I
could do it, I was like, yes.
Now I didn't say it because
I was trying to lie.
I said it because he
was so excited about it.
I felt like ashamed
that I couldn't like.
Answer his call.
I want to go
figure it out.
Right?
So far I hadn't like, figured
out a lot of things in life yet.
I'd figured out a few, but like,
not like this, where there was
like a very intentional call to
action where a human was saying,
can you do this by this date
and I'll pay you or not pay you.
And I was like, oh, shit.
Yes.
So I say yes.
Long story short, I end up
going and finding the resources.
I found a developer
that, that could, that
could build e-commerce.
Uh, funny side story, Ryan.
The person that I found had,
uh, there was a letter to the
editor about Joel's textbook
exchange, and he was like,
Hey, I hear you can sell.
I hear, I hear Joel is selling,
um, textbooks on the internet.
Is that a new thing?
Is that possible?
I mean, how funny is this?
Right?
It turn out, the person that
was asking about it was Joel
from Joel's textbook exchange
and he and he, he sent a
letter to the editor of the
campus newspaper to essentially
have them print an ad about.
Textbook.
Yep.
There you go.
So I somehow played Joel.
Somehow I somehow
got ahold of him.
I was like, well, if you
know how to do a textbook
exchange, then you know what
a shopping cart is, right?
And he was like, yeah, sorta.
I was like, can you build one?
And he said, yeah.
I was like, you're hired.
He was like my first employee,
but, but we got it done.
We shipped the e-commerce.
Yeah.
And I was like, oh.
So part of growth is challenging
myself to do things that
I couldn't do yesterday.
Hmm.
I wonder if this will
ever come up again.
Like 10.
I mean, like
I, this goes back to something
I was saying earlier, right?
It's not about certainty.
Confidence isn't only aligned
with what you've already
done, it's about what you
believe you can do next.
Right.
Understand.
Again, if we fix confidence
to just what we're certain
of, like, I've already done
this so I can do it again,
you're gonna miss out on most
of what it is to be a founder.
'cause we have to go do
a bunch of shit that's
never been done before.
You bet's the whole point.
Right?
So it's not about,
yes, of course.
Having done something
that leads up to that.
Right.
If you'd never built a
website at all before saying
yes to building e-commerce.
It might have been
a step too far.
Right.
But you'd taken a bunch
of little steps up
to that point, right?
Like, hello world.
I coded some HTML.
Yep.
All the way through, you know,
building, you know, multi-page
sites and, and, and complex
navigations, all this stuff.
And then you're just
layering things on.
So back to your point, it's a
lot of little victories that
start to stack up into, okay,
what's the next thing that
I need to do that I haven't
yet, that I'm not sure how
to, but that I believe I can.
That's confidence.
That's what I'm
doing with my kiddos.
Now what I'm teaching them
are these micro challenges.
They have the benefit of
their dad giving them a
very deliberate framework.
Like I'm not just saying,
Hey, randomly do this.
I'm like, this leads to this.
And fortunately, my, my kids
have a very natural appetite
for this stuff, right?
They, they, they
like challenges.
And so what I explained
to them, I said, in
order to get from here to
there, it's not one step.
It's a hundred steps in that
direction, some of which
take you off path and some
of which put you back on.
But the goal is to just
keep chipping away at steps.
So as this relates to,
to our community, to
our founder community.
Take a look at what you're
going to do today, tomorrow,
and ask yourself what
you're doing right now.
Where could you be
challenging yourself more?
Right.
This is a bit of a meat
heady example, but if you're
bench pressing and you're
normally gonna bench press
180 5, put 2 0 5 on the
bench and just press it.
And part of your is like,
well, I can't do that.
And you never will until you
put it on the bar and try
and, and that's the point
you have to intentionally.
Keep pushing yourself
further than you could,
than you would otherwise
go in order to level up.
You know something that's
really funny about everything
we talk about here is
that none of it is new.
Everything you're dealing
with right now has been done a
thousand times before you, which
means the answer already exists.
You may just not know
it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems all
dayLong@groups.startups.com.
So if.
Any of this sounds familiar.
Stop guessing about what to do.
Let us just give you the answers
to the test and be done with it.
Well, let's stop
for just a second
and I wanna talk about
the line between ambition
and recklessness, right?
Yeah.
Like between well-served
confidence and, and, and hubris.
Right?
So, going back, like you
said, you know, you hadn't
done that thing before,
hadn't done eCommerce before,
but you'd heard about it.
You knew it was
sort of possible.
There was some talk about it.
So this wasn't coming out
of thin air, but like.
For founders who are facing
these situations where
it's like, what can I feel
okay attempting, what can
I feel good about trying?
How do we start to draw that
line?
I think we start at the,
the very least is if again,
uh, pardon my meathead
bench example, but, but
if my bench is 180 5, if I
don't do something that's
incrementally more than that,
I'm using the bench example
just 'cause it's very numeric.
Right.
If I don't put more on
the bar to try Yeah.
I will never get further.
Okay.
Now, correct.
Do I put twice as much on
the bar and crush myself?
No.
The, the idea is that I'm
pushing a little bit further,
so this is, again, in the client
world, I'm making a slightly
bigger commitment than I
would have time for right now.
That's actually how you
grow in the, um, the product
knowledge world, right?
Let, let's say that, um, part of
what you need to do as a founder
is you need to become, um,
adept at learning finance, okay?
No, you're not gonna become
an entire CFO, but you
can learn how an income
statement works, right?
Yeah.
Yeah.
You can say, I'm
just gonna learn the.
Basics of where Yep.
Income goes, where
expenses goes, and how
profit ever happens.
Right?
That's it.
I'm not gonna try to
learn more than that.
Yep.
But that's more than
I know right now.
That's 10 more
pounds on the bar.
That's how you do it.
What about the case?
The case?
Because.
I totally get the case
for incrementality, right?
Yeah.
And I, I teach
this all the time.
We talk about this all the time.
If you've never tried
this, don't dump $10,000
into it the first month.
You've never tried
this marketing channel.
You've never worked
with this developer.
Just like try to take
little, little bites.
What about the case where we're
about to engage in something
that we've not done it?
All before, and there are plenty
of these things in fandom.
Yeah.
And we don't necessarily
have any incremental
bar to work from.
Right.
Because let's, let's use, let's
use your, your bench example.
I have never bench
press in my entire life,
which is nearly true.
I have done it a few
times, but not very many.
So if, if you say,
can you bench 2 0 5.
I either have to say yes or no.
I don't have anything
to base that off of.
Sure.
I don't know if I can bench 180
5, so I don't know that two.
Oh, five's a stretch.
Yeah.
How do we approach that?
You start with the
bar, you start again.
Instead of saying, I
can't do it at all.
You start with what's
the smallest thing
that I can possibly do?
And I have found, this is Ryan.
This is my absolute
superpower that I've owned so
incredibly well, especially
over the last few years.
Again, as we were talking about
building this house, when we
were doing the architecture,
this is like so specific,
like when we were doing the
architecture, I was watching
the architect and like going
through the ideas and I gave
him like a caveman painting
and he gave me back something
that looked nothing like what I
wanted, not even remotely close.
And, and while I was watching
him do what they call the
massing, which is when
they're coming up with the
initial concepts, I was
working with their, um.
3D modeler and the 3D modeler
goes into the 3D program and
does, you know, some renderings.
And I was like, how do
you do that Again, this
is question guy, right?
I was like, what are you using?
And he's like, I'll use a
program called Sketch Up.
I'm like, oh, okay.
That's interesting.
I've used a little bit of Sketch
up downloaded tomorrow morning.
Yeah, exactly.
I'm like, so I'm not gonna be
able to just like jump in this
program and become an architect.
Right?
Like it is just
not how it works.
Yep.
But you know what I can do?
I can jump in this program.
And Ryan, I remember when
I showed you SketchUp.
I was like, the first thing
you need to do is draw a box.
That's it.
That draw a box, right?
And you can ex an extruding in
any direction you want.
Again, this sounds so tiny,
but this is exactly how this
is, this is the, the, the
hidden move to all of this.
I was like, okay, I
just need to draw a box.
And every house is
just a series of boxes.
Right.
It becomes more, but once I know
how to draw one box, I can draw
another in another, in another.
Yeah.
And I'll draw better boxes
over time, so on and so forth.
Uh, my daughter, uh, I, I
haven't told you this yet,
is about to teach me guitar.
She's been taking
lessons for years.
She's fairly adept.
Right.
And I've always wanna learn
to play one's sitting in
the cornerback there.
Well, it's been, is that, is
that thing moved in 10 years?
That actually is a prop.
It's a real guitar and I
have no idea how to play it.
And people ask me all the time
like, oh, oh, you're a musician.
I'm like, I'm not.
I'm just a guy that ha happens
to have a, a guitar in the
back of his, his office.
And when we sat down on this
weekend, she talked about it.
She's like, dad, you know,
I really want to teach
you how to play guitar.
I said, teach me one chord.
Just like start there and I'll
play it over and over and over.
Then teach me too.
Right?
I think, Ryan, this is a long
way answering question, but I
think when people try to learn
or do anything, especially when
it comes to being a founder.
They try to do too much
and by way of that, they
don't do anything at all.
They get on the bench and they,
they try to push 180 5 when
they should be pushing 35 and
they're like, oh, I can't bench.
No, you can't bench
that much 'cause you
haven't started with 35.
Yeah.
Yeah.
We see this in so
many different way.
Like fundraising's probably a
really easy one to pick on here
because people call me like,
I need $5 million to build
everything I ever want to build.
Okay, cool.
$5 million Dream House.
What does pitching a tent
on the land look like?
Right?
How can we just
occupy the space?
What's exactly, what's the
least you can do that will
make a meaningful difference
between where you are today and
where you could be tomorrow?
Yep.
And I think that it's just,
it gets really hard because
again, we, we spend so much time
pitching the vision and putting
confidence behind that and
showing how big and wonderful
this thing can be that we forget
that we have to talk big, but
act really, really small and it
just makes life so much easier.
Right.
I think every week I see at
least two founders between
my Monday and Friday sessions
who come out with what,
you know, an amazing plan.
Lots of stuff, really cool
things they're gonna accomplish,
but they're biting off way more
than they could possibly chew.
Yeah.
Because of that, they don't
really know where to start.
They don't have the
competence to start.
'cause they're like, well,
there's just so much.
I'm like, well there isn't
really, to your point.
Yeah.
A full architectural rendering
is a shit ton of stuff.
It's a lot of work.
Started with a box
or a lot it started
with, yeah, I got asked
this question yesterday.
I was on site, we were
going through inspections.
You and I were talking about
this and the electrical
inspector was like, wait,
you designed like all the
electrical in this house?
Like, and it's, it's a
super complicated house.
I'm like, yeah.
And he is like.
How I was like drawing lines
one circuit at a time, right?
Like I understood what
a 15 amp circuit was.
I was like, oh, I'm gonna
need another one of those.
Oh, it turns out every,
every light circuit
is typically 15 amps.
So I'll just, uh, copy paste
that to, and I was like,
on and on, and I learned
one circuit at, at a time.
He was like.
That seems super obvious when
you say it, but I would've never
thought to do it like that.
I was like, that's why
it's a engine move.
Alright, so, so, uh,
let's keep going.
So I, I would say in making
those big plays, I think making
enough of the small ones, Ryan,
is what gives you the confidence
to make a big one, right?
And, and sometimes you don't
even realize you're making the
big one until you know, until
it becomes something else.
Sometimes the big one just
really isn't obvious because
it is just a collection
of the small ones.
Right?
But, but I, I think that's it.
So let's, let's back
up for a second.
Right.
So we started with, we started
with curiosity and saying that,
like, asking the questions,
curiosity, uh, starts to build
some of that early confidence.
And then we have to go
between the curiosity and
the actual action where we
say, okay, now I'm gonna, I'm
gonna, I'm gonna take what
I've learned, I'm actually
gonna do something with it.
The next thing that I think
is that, that, that ends up
needing to happen is that
we gotta get really good at.
Being wrong.
Right.
Which is to say that like a lot
of those little things, like
sounds, we're gonna go try.
Yeah.
Is they're not gonna
work and that's okay.
Right?
Because true confidence, again,
I'm gonna say this, this will be
the last time I say this today.
True confidence is
not certainty, it's
resilience in motion.
This is what it is, right?
Confidence comes from
saying, I don't know, but
I'm willing to find out.
I found out and
I'm willing to try.
I'm willing to try and I'm
willing to be wrong and
sometimes get it right.
So that's what I
wanna talk about.
Now.
I wanna talk about like how
do we get good at being wrong?
I found it easy,
comes naturally to me.
Well, I got the
wrong part down Pat.
Um, yeah, I'm super good at it.
When you were going into
your career, how did
you see being right.
Versus being wrong like that.
It's o like what would've told
you that it's okay to be wrong.
Yeah.
You know, interesting.
Because not a lot, I think
as I entered my career,
nothing, in fact, I've talked
about this before, but you
know, we came from like an
achievement household and a
performance culture, right?
I performed well in school,
was a, was a, uh, you know,
strong student athlete, merit
scholar, all that stuff, right?
Right.
And that was what
was celebrated.
So it was always like.
What's the standard
pass It, don't be wrong.
Be right as much as you can.
There's a real penalty
to being wrong.
Get to university.
It's the same game.
Everybody's, you know, vying for
some level of, of outcome at the
end of that, and that's related
to how well do you perform here.
Right, right.
So none of it.
Was, was, was taught as I
was, you know, being prepared
in the traditional way.
Contrast that to the fact
that I had started multiple
businesses, you know, from
my lemonade wagons to lawn
mowing, to snow removal, to the
cattle company, to the little
software database and, and
practice management system that
I built up into university.
When I began my
digital agency at.
19. Right.
Those things were, were
what taught me it was okay
to be wrong sometimes in
extremely brutal ways.
Right?
I think I've shared this
one before and I'm, I'm not
proud of this, but one day
I made a decision between
going out to feed my cows.
When they were still very,
very young and I needed to
bottle feed them at this
point.
Hold on, back up.
Just so everybody knows,
Ryan, you're not being
metaphorical right now.
You're from Ohio.
I'm not being metaphorical.
I was literally, I used to,
I found an arbitrage play
where I could buy male dairy
calves from dairy farmers for
$10 a piece, put $50 worth
of milk replacer into them,
put 'em out the pasture.
A bag of grain for 25
bucks and sell these
things for seven to $800.
Right, right.
So at 10 years old, this
was a fantastic business
in a big level up.
A huge level up.
Right.
But so I, I decided one
morning on a Saturday morning
that I didn't wanna wake
up at five o'clock so that
I could go feed before I
went to basketball practice.
And I thought, I'll do it
after basketball practice.
Well, you may know will.
Basketball is a winter
sport and winter is cold.
Um, and young animals
are very vulnerable.
I came back to find one of my
five dead, his name was Star.
I was still naming
at that point.
That's how, that's how
tender and naive I was.
Never do that.
Um, and uh, so I learned
the cost of being wrong.
I learned the cost of
being wrong there, but
I also learned that.
That is gonna happen.
Sometimes you're
gonna make decisions.
And it didn't stop
me from doing it.
It didn't stop the other
four from being viable.
It didn't stop me from
making money that year.
It didn't stop me from deciding
to buy more the next year.
Right.
Um, and so I think it was all
those little things, man, you
just start to stack up this,
this ability of being wrong.
I
think we came from
an era of bravery.
I. And when I mean bravery,
I, I mean bravery being
like, you have to be
brave and bold and Right.
And that bravery, uh, was
an attribute of being right.
And here's A BMW
or here's a BMX bike kid.
Go prove that you're brave.
Right.
Exactly.
We were given challenges
and please don't wear a helmet.
Please don't have it.
Um, it reminds me
of a great quote.
And, and of all the places that
quote comes from, it comes from
one of my favorite games, which
is the Civilization series.
Right.
I do not wanna recount
how many hours I have on
steam to civilization,
but
it's probably longer
than the last.
I saw a screenshot once.
I'm
actually wondering how many
people you have working
on that simultaneous.
'cause it's more hours
than you've been alive.
Seriously, as if
I'd never slept.
There's a quote
that that pops up.
You know, whenever you hit
certain milestones, Uhhuh,
and, I mean, I'm such a nerd
that I can tell you it's
the military tradition, uh,
civic, and uh, the quote.
Is bravery is, is knowing you're
the only per, is being the only
person that knows you're afraid.
And I love that quote.
Bravery is the person
that knows you're afraid.
And I think that goes to that.
That speaks to what we're
talking about, right?
Yeah.
Which is this idea that I'm
brave enough to be wrong.
I. And I'm the only person
that's willing to admit that I
have no idea what's happening.
Right.
Like I felt the more I could
be brave by being wrong, the
more unstoppable I became.
Right?
I, I, yeah.
I really, genuinely,
genuinely believe that as I
got good at making mistakes,
like you're talking about,
I was like, oh, damn.
If I'm willing, like, you know,
Ryan, you and I are working on
some landing pages right now if
I'm willing to just try 'em all.
And not try to have the
right answer and just
let the answer find me.
By virtue of elimination,
I am unstoppable.
Now, it doesn't mean I'm,
I'm gonna be victorious.
It means the opposite,
where I'm afraid to make
decisions or take leaps.
Yeah.
I'm afraid to be brave
because I'm afraid
to be wrong.
Yeah.
Right.
Which isn't, yeah.
Which isn't really competence.
I mean, this is one of
the things where, like,
I think I, I talked about
this early, the difference
between confidence and hubris.
Bravery is, there's still a
belief that you can, but it's
based on something, right?
As, as somebody else
famously said, the difference
between bravery and
stupidity is the outcome.
The
outcome, right?
We know.
We know after the fact,
but I think it does.
It takes a level of
confidence to say, yes,
I'm willing to try this.
It takes a bigger level
and a more important level
of confidence, I think,
to say, and I'm willing to
live with those, with the
consequences of being wrong.
Huge
part of it for sure.
Just a couple weeks ago, we had
a little situation at school
and my, my 7-year-old comes to
me and he's, he's visibly upset
and as he starts to tell me
the story, he's starts to cry.
He's telling me about something
where a, a thing happened and
he tried to intervene and then
through the intervention he got
in trouble, uh, for standing
up in the way that he did it.
We talked about all the,
the ways he could have kind
of softened his response
a bit, but that wasn't
really the important part.
He goes, at some point he
says, but wasn't it brave to
try to do the right thing?
And I said, yes, it
absolutely was brave to
try to do the right thing.
He's like, but bravery
doesn't stop there buddy.
You gotta be brave enough
to accept what happens
the minute you say, yes,
I'm willing to try this.
Yes, I'm willing to do it.
I'm willing to jump.
You've gotta be willing.
You have to be brave enough to
accept what the fall feels like.
Not sure that landed all that
well with the 7-year-old.
Maybe he'll remember it
someday, but that's okay.
I said it planted seeds,
shook his head at the time
and he stopped crying shortly
thereafter.
Yeah, right.
So given what we do for a
living specifically as founders,
I don't know that I'd give
the same advice to doctors.
Ah, just get some
surgeries out there.
See how it goes.
Wing it.
You're gonna be wrong, but
this is a valve replacement.
We're gonna cut the wrong valve.
Yeah.
You know, like whatever.
Um, yeah.
Or, or legal, you know,
file some motions and
see where it goes.
You know what I mean?
Yeah.
Right.
Like, uh, not quite the same
thing, but for what we do,
because there is not a certain
path in most of what we do.
You can't be the person that
always does the surgery, right?
Or, or always wins
the legal argument.
That actually doesn't
work in our business.
So if you wanna be good at what
we do, which is jumping into
the unknown with no possible
knowledge of what the answers
are going to be, which is
all of us by the way, right?
That's not specific to like,
you just happen to not know
because you're 22 years old,
it's no one knows because
you're going to a market.
With a product that's never
been invented before, a
market that doesn't exist in
a team that's never done it
before, how do you possibly
know what these answers are?
Yeah.
So in order to be able to
have the confidence to to go
through that, you have to be
able to say, I don't know.
Right?
I actually don't know what the
answer is gonna be, but what I'm
gonna do is I'm gonna try every
version until the right answer
presents itself and be good.
That be good.
Being confident we may
fail, we may try everything
and everything fails.
It happens.
Ryan, you and I fail at a
million things we just do.
Yes.
Right.
But I think our perseverance
toward failure is what helps
us unlock the things that work.
It
absolutely is.
I mean, this is where
the learnings come from.
I, I, I know that like,
fundamentally people get this,
but I think we can, we forget,
and again, I'm gonna go back
to something I referenced
earlier, which is we get
so used to having to pitch.
So let's, let's, I can
tie this back to like an
investor pitch, for example.
Yeah.
Where we have to be.
So certain of ourselves,
we have to present this
future that clearly
doesn't exist yet, right?
We gotta go make it true.
We need somebody's
money to go do that.
And so I think one of the
questions that founders seem
to struggle with is like,
how do they stay credible
with your team, with your
partners, with you know,
your clients with investors?
While sort of openly admitting
uncertainty and, and I just
saw this done really well
a couple weeks ago now.
Founder was sharing
their deck with me.
They ran me through the pitch.
They openly exposed a
bunch of places where
we thought this would be
true, and it wasn't at all.
We were completely wrong.
I like that movie and
here's what we learned and
here's how we're doing it.
And then here's what we also we
did wrong, and here's what we
learned from that, and here's
what we're doing with that.
And they did such a beautiful
job of showing the vulnerability
and showing and building
credibility by saying,
yeah, we screwed this up,
because of course we did,
because there was no right
answer to this at the time.
We had to go seeking
the answer right now.
I think if you're doing
things like, you know, like
you're making silly mistakes.
Sure.
What would a silly
mistake look like?
Like, well, we're only
going to accept PayPal.
You're an in-person cafe.
That might be a
weird choice, right?
That somebody could
give you advice on that.
You don't need to go try
that to figure it out.
Somebody else is gonna tell you
No, probably just get a normal
POS like everybody else does.
It'll be fine.
Right, right.
But that's not most of the
type of decisions we're
dealing with as founders.
It's things that we.
Don't know.
And that quite possibly
neither does anyone else,
because we're doing something
nobody's ever done before.
And that's okay.
We've gotta chip away the,
the way I see it, Ryan, like.
Confidence is built, not born.
It is a muscle that
you have to develop.
So when folks think about
like, I wanna be this
confident leader, awesome.
The way you do that
is 1% at a time.
It's not like a a you,
you flip a switch and you
wake up tomorrow and you
are a confident leader.
Every confident leader.
Became a confident leader
because they were willing
to put themselves out there.
They were willing to ask
questions, they were willing
to challenge themselves,
make those big plays.
They were willing to be
wrong so many times so
that they could have the
advantage of being right.
And over time with enough
big plays, with enough, uh,
confidence that they built,
they chipped away at, they
became the leaders that you
see today, the people that
stand up and can say, this is
what the future is because.
I've built it before because
I've tried everything before.
So I think for a lot of
folks that are thinking
about, Hey, I'm not confident
enough, that's okay.
That's okay.
You won't be more
confident tomorrow.
You'll be 1% more confident
tomorrow if you challenge
yourself and ask the questions.
But over time, if you keep
chipping away at it like
anything else in life,
you will become exactly
the leader you need to be.
And one day you're gonna wake
up and you're gonna look around
and say, I am confident as hell.
Hallelujah.
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 bootstrapped
founders and the advisors
helping them win in the
startups.com community.
Check out the startups.com
community@www.startups.com
to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.