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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to another episode
of the Startup Therapy podcast.
This is Ryan Rutan, joined
as always by my friend,
the founder and CEO of
Startups.com, Will Schroeder.
Will, founders love to tell
us That they're almost ready.
And I think you and I would
agree that almost ready is
where startup dreams go to die.
The only thing that
makes us ready is
contact with the market.
So we'll, let's talk about why
founders think that getting
more prepared and starting
later feels responsible,
but I think you and I would
say that's probably just
fear with nice veneers on.
It is, and, and what's
interesting to me about
that is we actually believe
that we can plan- Yeah
for problems, right?
Yeah.
That, that if we just wait long
enough, if we just plan enough,
right, if we get enough, uh,
of our ducks in a row, so to
speak- Yes … then we'll be
able to avoid the problems.
Which, which brings me
to the Mike Tyson quote,
which only you can deliver.
If you would indulge me,
on your version of Mike
Tyson's famous quote.
Everybody had a plan till
I punched them in the face.
It was better earlier.
You're better.
Oh.
Honestly, when I did that,
when I did that a few days
ago in jest- … like, it was
better, but now on, on- Yeah.
… on, on, on the spot, like,
I feel really bad that I
did… I'm sorry, Mike.
Please don't find me and
change my plans or my face.
Everybody has a plan until they
get punched in the face, which,
you know, mirrors the quote,
"No plan survives first contact
with the enemy." It works in
the same way, which is, like,
all the planning in the world
will not mean jack shit, because
until you get out there and
start doing this and take real
lumps with real customers and
product and everything else
like that, and investors, you
can't plan your way into it.
Yet, yet, but we believe that's
not true.
Yeah, we think so.
Well- Right?
… I mean, look, it comes
from an okay place, right?
I think that in so much of life
we've been told that you have
to prepare for all these things.
Everything had a prerequisite
up until this point.
Then you go to start, right?
Like, you know, before you
got the job you wanted, you
had to do the grunt work.
Before you got to any of
the grades you wanted,
you had to do… Right?
Everything had, like, some sort
of a, a starter set that you
had to complete so that you-
Yeah … could level up into.
Right.
But the thing is, in the
startup space, readiness is not
a prerequisite for starting.
Readiness- Yeah … is
the result of starting.
Readiness is what happens-
… sometime after we've started,
often long after we've
started, and we're like,
"Okay, I started six years ago.
Now I'm ready.
Now we're ready.
Now it's actually working."
If I think about really where
you and I both started, you
know, early in our careers-
Yeah … like, you know, very
early in our careers, before we
realized that there should've
been maybe something else we, we
should have considered, right?
Yeah.
Like, I found out that I
had started a business after
I had started a business.
After you had
started the business.
Yeah.
And just, like, to give you
a sense for, for what ends
up happening, this is like,
I'd just turned 19 years old.
Like, so like three years ago.
And so, like, I got into
this thing where, um,
I'd built some software.
This is 1993.
I mean, we are going into a
frigging time machine here.
Yes, we are.
Um, I'd just built some
software on this new
diabolical piece of software
called Microsoft Access.
Oh.
Oh.
On
floppy disk, right?
You were- And so- You were
at home programming databases
Yeah, right?
I always learned
how relations work
Just not the human kind.
Just- Yeah, exactly Just the
Those do not go together.
I built the software, and
I built it for the company
I was working for to be,
to do contact management.
And this is going back so
far that before we had the
c- this contact management
software that, that I was
building, they were just files.
We just had- Yeah
manila folders with, you know,
people's information on them.
Every time you called
somebody, you just wrote
it on the call sheet.
Anyway, so I build this
software, and, and I
roll it out, you know,
within our company.
And then one day, I get
a call from one of the
companies we were partnered
with, and the, the CEO calls
me and says, "Hey, can we
get some of that software?"
And I was like, "I could
sell it to you." Yeah.
A- and he was like, "Well,
fine. Yeah, just, like,
name your price." And guess,
Ryan, this was my price.
This was 1993 going into 1994.
My price to license my software
$1500.
Oh.
All of it at once?
That was the all in- Was that,
was that payable over time?
Was there a layaway option?
Oh, oh yeah.
Yeah,
uh, it was, like, you'd
have to understand where I
was in life at that point.
I was making $5 per hour.
Yeah.
So $1500- Yeah … was
like a billion dollars.
Yeah.
And, and I'm 100% sure, uh,
when I told that CEO what
the price was, he didn't
understand the pricing.
Like- Yeah … he
was like, "For what?"
Yeah.
Right?
For, for, per seat?
Per year?
Per what?
What do we mean?
Exactly.
Exactly.
Yeah.
Like, like, and he still didn't
understand- Yeah … that I
was actually gonna give him all
the software and install it,
'cause everything was custom.
And install,
yeah.
Probably maintain it, teach
people how to use it, you know?
Okay, s- right.
So all of a sudden I realize
that someone's willing to
pay me to sell them software.
Yes.
And I was like, "I wonder
if more people would be
willing to pay me." Yep.
And so that kind of is how I
fell into becoming a founder.
See, I didn't, I didn't know
I was gonna become a founder.
No.
It wasn't like, "I'm gonna go
build software, and then I'll
find somebody that needs it,
and then I'll sell it to them,
and then I'll be a found-" no.
It was just like, eh,
you just did a thing.
Yeah.
You started something,
and it turned into
something else, right?
Which is how it
always works anyways.
We just don't usually
see it that clearly.
I'm gonna give you
another example that's
way more ridiculous, okay?
And absolutely irresponsible,
but I'm gonna tie
these two together.
Okay.
Years ago, on Christmas Eve
of all time, uh, Sarah, my
wife, and I were down in, uh,
in The Bahamas, and I'd always
wanted to go scuba diving.
She was terrified of the water,
like, of doing that, so she
was like, "I'll sit on the boat
and get a tan- Yeah … while
you figure that out." I'll live
while you go do that.
So g- this is how
bad it is, right?
They take us out on the boat,
and there's, like, these
three just dudes, right?
That are explaining us to
the, the group of us there,
like, how scuba diving works.
Yeah.
And maybe the worst explanation
you can possibly imagine.
And, uh, the only thing I
remember that they even said
was that if you get in trouble,
tap your, uh, your tank.
Uh-huh.
And that's how, you know,
it'll make a sound, and
that, that's how people will
know you have a problem.
That way we know to head
back to shore really fast
before the authorities show up.
Yes.
We'll know the last
time we saw you.
And so I jump in with my
instructor, and they do the
first thing where you submerge,
and then you're trying to
pressurize and whatever.
Yeah.
And I get it wrong, of course
my head explodes, right?
I get back up to the top,
you know, I re-pressurize,
I go down again.
Well, the next time, time
I go down again, I'm fine.
And I just stayed down
there for 45 minutes.
Yep.
With no training whatsoever.
Right.
Right?
I just swam to the bottom
of the ocean, and just…
It was amazing, actually, right?
Now I say that to say, if
you had said, "Will, the
only way that you can scuba
dive is that you have to go
through all this training,
you have to be in the pool-
Yeah … and everything else,"
which you should, by the way.
I just wanna Yeah.
I wanna be clear.
If I thought the whole time
that I would never be able to
do it unless I went, unless
I waited and planned and
did all these things- Yeah
I would've believed
that that's true.
There is another version, which
I don't recommend to anyone,
where I could also just jump in-
Yeah … swim to the bottom of
the ocean, and figure it out.
That version is told
by a Will who's not
here to tell that story
today, I think.
That's my twin brother, Phil.
That's the reason you're
not telling that story.
Yeah.
Yeah, yeah.
The reason I tell this story is
I think people believe that they
can learn to swim by reading
and planning about swimming.
Yeah, of course.
Sometimes you just
gotta jump in, right?
You gotta
get your feet wet, yeah.
Correct, right?
There's no, no version of,
of swimming is, it happens
on, on dry land, right?
And there's a lot
that you can do.
And by the way, this
isn't life and death, like
submerging yourself in water.
There's a lot that you can
do that you don't realize,
and this is where I wanna
tie it back together.
When I was 19 years old, and
you were damn near, you know,
you were college age too when
you were getting started- Yep
I didn't know that there
was something to plan for.
There wasn't.
Literally, I, in the same
way like I just answered
a question, right?
You built a little software to
scratch your own itch, right,
at the time when you were
working with that company.
I've told this story before.
I was walking in the halls
at OSU, and a previous
upperclassman from a couple
grades ahead of me at my, at
my high school bumped into me.
And he's like, "Hey." And
then just like, we had a
two-minute conversation.
He goes, "Wait, you know
computers, right?" Do you
remember when people used
to ask that, when that was
actually a legitimate question?
My grandmother
t- till, till her last day
was like, "Will does something
in computers." In computers.
Like, thanks Grandma.
You know computers, right?
And I said- Yep … "Yes."
He's like, "Great.
We need a website.
Can you make us one?" I said,
"Sure." And then I went to,
you'll appreciate this, Will,
I went to Micro Center and
bought probably Frommer's
HTML or something, right?
Like, I, I don't remember
which one it was.
Uh-huh.
But I bought
O'Reilly's somebody.
Bought an HTML book and,
like, that weekend I figured
out how to code a site, and
by that following Thursday
I had built their website.
But there wasn't like, I
wasn't like, "Okay, let
me go get ready." And, and
look, I, yes, I read a book,
but the book was just to
know how to do the thing.
It wasn't, I wasn't sitting
around prevaricating going,
"I wonder if this is really
the right time to launch
a web design agency."
Number one, I'd never
heard of such a thing,
because I had never heard
of such a thing, right?
Uh, fun fact, I got a text
message from Micro Center not
two hours ago about the Memorial
Day sale that's still going on.
And for all you nerds in the
audience, some of you know
Micro Center because they've
got a regional presence in
places, but Micro Center is
the old school, still exists
version of independently owned
computer store, where you go in
there and the people there are
very much the kind of people
you would, it's the people
that would've been working at
RadioShack back in the day.
Ryan, whenever I get to
go there, and I get to go
there, like, once a year
because I need something
very specific, I'm like, I
have so many warm memories.
And the best part about
this, every time I check
out and I give them my phone
number, they always ask you,
"Are you still at 171 West
Maynard Avenue on campus?"
I'm like, "Yes,
I am." Yes, I am.
Yes, I am.
Um- 40 years later … besides,
it's been a while.
But anyway, I think what's
interesting about that is if
someone had told you- Here's
what you need to do before
you're allowed to do this,"
you would believe them. I
would've. And I think we tell
ourselves that, "I need to get
all these, these ducks in a row.
I need to w- Yeah.
What about, what
about your branding?
Have you thought about how
much time this is gonna take?
You know, have you, have you,
have you- Right … launched
your… Do you have a,
a charter of accounts?
Have you… Are you
gonna go LLC or S corp?
What are you gonna do?
Yep.
Like, all of these things that
could've gotten in the way,
and some of those th- become
necessary at some point, sure,
once you figure out if any of
this works at any level, right?
Had I gone and done all of
that stuff and then figured
out I actually couldn't code a
website, that would've been kind
of a waste of time, wouldn't it?
I mean, but you figured out…
Tha- and I think that's the
part that folks are missing.
So I, I think part of what
concerns me when people say, "Is
now the right time to start?"
We get aw- asked an
awful lot about this.
Yes.
My answer is always,
"No, you're wrong."
Mm-hmm.
The right time should've start-
would mean you already started.
Yeah.
If you're asking the question,
you're already too late.
Yeah.
That doesn't mean you can't
get started tomorrow, but
that's sort of the point.
But I think, like, waiting
is basically stalling, right?
I think that- Yeah … when
people are, are trying to plan
for what, you know, what could
happen and like, "Oh, you know,
we just wanna have this perfect,
you know, plan to get started,"
it's a massive step backward.
I don't think people
understand the cost of
waiting in this game.
I don't think so either, and
as we were talking about this,
I was starting to realize
there's more of a cost to
it than I had even maybe
previously associated, which
is that, like, every day lost
is a day lost or whatever.
Y- yes, but it's not just that,
and it's like, yeah, if, you
know, starting today is better
than starting tomorrow, yes,
but, like, each day that you
don't start is, is not just
you didn't start, it's the loss
of everything that would've
happened in that period.
Yeah.
So there's actually this
negative compounding
effect for the, the longer
that you wait, and- Yeah
and you've got plenty of reasons
and excuses and all this stuff.
Planning is great, and, and you
should plan a little, right?
Like, I planned to go get a
book, and then I planned to
build a test site, and then I
planned to build their site.
That was okay, but, but
planning in that case was
valuable because those plans
specifically led to action.
If plans don't lead to
action- Right … it's
just theater, right?
And, and we don't need that.
Yeah.
We just don't need that.
We do teach a lot of planning
at startups.com, right?
Sure.
Just to be clear, like, you
know, we teach people h-
doing o- idea validation.
We teach them, you know, how
to- Yes … uh, plan to go do
a capital raise, et cetera, but
that's a little bit different.
That's the act of doing.
Yes.
Right?
While planning.
Yes.
It is, I'm building websites for
clients while I'm figuring out
what it means to build an agency
to build websites for clients.
Yes.
Right?
Like, I'm learning by doing,
and that's the part that
I don't, I don't think
folks fully appreciate
in this particular job.
I think a lot of people
are like, "Hey, for every
other job, you have to get
education, degree, whatever
in order- Right … to go
do it." This isn't that job.
There isn't a parallel.
There isn't a parallel where
you have to wait and learn
and prepare to do this job.
You prepare to do this job
by doing this job Right.
It's very specific.
Let me draw a line here,
'cause I, I think there's
an important thing here.
Uh, you said, you said
something great there, which
is, like, around, like,
we're, we're getting people
to do stuff, and we're,
we're having people planning.
I wanna draw a line here,
though, because there's still,
like, you can still stall
and look and feel productive
because there are documents,
there are meetings, there are
research, there's strategy.
But nothing is being tested.
Nothing is being tested.
Stuff is being done, but
nothing's being tested,
nothing's being proven, right?
I think- Right … actually
starting something, but I
mean, like, getting in front
of customers, talking to the
actual people you wanna sell
to, talking to people you
wanna solve the problems for.
That type of launch
forces response.
Right.
Response starts to create
learning, and learning is where
the actual progress comes in.
So I think that we can be doing,
even… So even if you have a,
an action bias and you're like,
"Oh, no, no, I'm not stalling
at all. I am doing so many
things right now." Okay, cool.
What have you learned?
"Well, I learned how
to put together a
chart of accounts." No.
That's cool if what you wanna
become is an accountant.
Not cool- … if what you wanted
to become was a founder, right?
Again, like, it has a place,
but it's not what we're trying
to, to force function here.
I also wanna point out, and
I don't think folks really
appreciate this, there is
a massive cost to waiting.
I think folks think, "Well,
if I wait, that's okay
because I'm building up
this other resource." That
resource is education, network
connections, capital, et cetera.
And all of that sounds like it
would make sense, but what you
don't understand is w- the time
you're taking to do that has a
direct cost- Yes … to the time
you're not getting shit done.
Here's the one thing that
I didn't appreciate early
in my career, 'cause I
just hadn't seen it yet.
I didn't understand how
important it was, going
back to your Mike Tyson,
to get punched in the face,
meaning, like, like, to fail,
until I actually did it.
So I'll give you an example.
Early in my career, I'll
never forget this, and this
is a character you know
that, that we've worked
with for a long time.
Uh, early in my career, I
go and I'm pitching one of
our first clients, right?
Mm-hmm.
It was Harrison House,
if, if you remember, like,
like, ba- back in the day.
Yeah, yeah, yeah.
And so anyway, I'm pitching
the client, and they need a
website and all these things.
One of my good friends, uh,
you know, g- guy you know
well from college, uh, is
standing there right with me.
And as I'm giving the pitch, the
client is, "Well, can, can you
do an e-commerce site?" Right?
And I was like, "Absolutely."
And as I was saying
that- … almost, like, on
cue like a Seinfeld episode,
he's like, "Absolutely not."
And I looked at him and
I was like… And he
was just being honest.
He was like, "Well,
yeah, no, we've actually
never done that before."
Yeah.
Right?
And I was like, "Bro." Yeah.
And I remember walking out
of the meeting and being
like, "You don't get speaking
lines anymore." Yeah, yeah.
Like, "You're not allowed
to talk in meetings."
And he's like, "What?
What did I say?" Like-
"You have mime makeup
at home?
Because you're wearing it
the next few-" Yeah, exactly.
I was
like… It was so like…
He was like, "What did I
do?" I was like, "You're
not allowed to say no-
Yeah.
"…
to a client." And I remember
he was so blown away by that.
But here's, here's why
it was a lesson for me.
I learned that lesson
when he said no.
Yeah.
Right?
Yeah.
It never occurred
to me to say no.
Yeah.
And I didn't realize
how important it was
to know that- Yes
until I watched someone do
it- Someone do it … like
a crash test dummy.
Yeah.
And then I was like, "Jesus, I
need to never do what that guy
just did." And I watched the
look on the client's face, the
sense of like disappointment
and almost shock- Uh-huh.
Yeah … that he
was being so honest.
Yes.
Now, we would end up
getting that account, and
we would end up building
exactly what they needed.
E-commerce.
We just figured it out.
Yes.
But had I not been out there
getting that experience, like
being able to see it firsthand,
in this case again kind of at
his expense, I would've never
learned that lesson, right?
Which wound up paying
massive dividends-
Yes
…
throughout my career- Yep … in
learning how to deal with, "Hey,
we don't have that capability."
Yeah.
"But it doesn't mean we
couldn't." You know, something
that's really funny about
everything we talk about here
is that none of it is new.
Everything you're dealing
with right now has been done a
thousand times before you, which
means the answer already exists.
You may just not know
it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems all day
long at groups.startups.com.
So if any of this sounds
familiar, stop guessing
about what to do.
Let us just give you the
answers to the test and be
done with it.
Stick with us for just a second.
Let's play this out
in a different way.
Now imagine instead of just
being in that conversation with
this mutual friend of ours,
imagine you were sitting back
at the office whiteboarding,
going, "All right, so how should
we handle client communications?
What should we say?
What shouldn't we?
Let's make up some
rules around- Yep
how we handle stuff."
Yep, yep, yep, yep.
Will you ever get this right?
No.
You learn more from one ugly
customer interaction than from
50- Like 40 years … internal
strategy sessions, right?
Every single time.
Actually, stick with that
'
cause, 'cause I, I think
we can pull a lot more out
of, out of that example.
Had we been in the whiteboard
session and we were to
say, "Hey, should we offer
e-commerce to clients?"
Yeah.
Our friend would've
vehemently been like,
"No, we can't do it." No.
Yeah, we can't.
"It, we should never bring it
up- Yeah. "… because a client
will never go for it." Right?
Now, now stick with this
for a second because I
think this is fascinating.
He would genuinely believe,
and have full reason to
believe, that no client would
say yes and that we could
not provide that service.
Yeah.
And if we limited the scope
of our experience to the
scope of that room- The
answer would've been no.
The answer would've
been no, right?
Like very, very vehemently
as I said, right?
Yes.
And, and I couldn't
argue otherwise.
Until you just go do it, until
you just go out there and you
say to the client, "Hey, yeah,
we can absolutely do it,"
and the client goes, "Cool."
And all the planning you
would've held out for, right?
Yes.
This, we'll have to go higher
for this and build that
expertise, et cetera, just
went out the frigging door
because you said one word: sure.
Like- Yep … that was
it.
Oops.
Yeah.
It's amazing.
This is the cost
of inaction, right?
Yeah, the cost of inaction.
Or this is the cost of, of
planning versus doing, right?
Like- Right … have you,
have I, have any founders
ever discovered anything about
their capacity by preparing?
Or did we discover-
Nope … it all by being
forced to perform, right?
I never learned that I was
capable of something I didn't
think I was capable of while
I was sitting around wondering
if I was capable of it, right?
Yep.
Yep.
It happened when I was out
there going, "Shit, I probably
can't catch that guy, but
it's, you know, minute 89,
I'm gonna try. I'm gonna run
him down." And I did, right?
Yep.
Sometimes I didn't, and
that's okay, but, like, if
I had just thought about it,
guess what would've happened?
I certainly wouldn't
have caught the guy.
This past weekend, uh, I had
a contractor out at, you know,
the new house that I'm building.
Wait, new house?
You just gave me PTSD.
You mean the old house that
you've been building, right?
That's, that's a
frigging vintage.
Yeah.
Um, and as we're walking
around it, I'm explaining to
him all the different systems
of the house, and I've given
you this tour a million times.
Like, you know, I'm like,
"Hey, this is how the
electrical systems work and
the geothermal systems work,
and, you know, this is h-
how I architected this and
whatever." I can give this
tour.
Right.
Yeah, exactly.
And so at some point he, he
says to me, he's like, "How did
you learn all of this?" Uh-huh.
Right?
Uh, like, "How did you learn
how to do the electrical
system or lay out geothermal or
build cabinetry or whatever?"
Yeah.
I was like, "It's easy. I
just did it." See the burn
on this hand?
You see the cut
over here, right?
And I wasn't being flippant.
I was like- No … the reason I
know how all of this stuff works
is because I actually did it.
I didn't say to myself,
"Oh, well, I can't possibly
design an electrical system
for a full house, right?
So I guess I just
can't do it." Uh-huh.
I'm like, "Of course
I can do it." Yeah.
Now, doesn't mean I know how to.
Right.
But I can learn.
It's the same way I feel
about entrepreneurship.
The reason I know how to do so
many aspects of this founder
world is 'cause I just did them.
Do them.
Yeah.
Right?
I- if you were to zoom out
and you were to take a look at
our depth of expertise across
so many disciplines- Yeah
right?
Yeah.
So I- I'm gonna take it across
the spectrum, and just so folks
understand, you know, that
are thinking about getting
into this, first understand
how deep our expertise
is across so many things.
So we have expertise,
like actual usable market
expertise, in marketing,
in finance, in fundraising,
in product development, in
engineering, in sales, in
like all of these things.
We've done these, like
professionally at like a, a- Yes
… pretty significant level, right?
Now, you might look at that
and say, "Well, yeah, but
how did you learn all of
those?" I took zero classes,
and I'm pretty much sure
you're in the same boat.
Yeah.
Well, I took a couple classes.
I'm not sure they aligned
with anything I actually
learned, but yeah.
You know, the best classes
I took, the one class that I
took that was game changing
for me- was Econ 101.
Yeah.
Great class.
I'll never forget, when I
got into econ, and I say
this because I, I'm saying,
like, it's, it's amazing
at how sometimes there's
just an unlock moment.
Yeah, yeah.
You just start to see
something in a way you
didn't see it before.
You go, "Oh, okay.
Yes." I just saw the
Matrix.
Like, I got this Econ
101, this dry, awful book.
And I remember reading about
supply and demand for the first
time, and I remember, uh, do you
remember the concept of utility?
Oh, yes.
Like, the amount of value,
like- Yep … like, goes down
as you have more of it, right?
The amount of utility you get.
And the example they
always use is, is a pizza.
Yep.
The first p- slice of pizza
has maximum utility, and then
the value of each additional
slice goes down exponentially.
Um, and- Until the next
morning, and then you find-
I was gonna say- … that
last leftover slice, the
utility on that one's pretty
damn high, to be honest
the way I
feel about vodka.
And so anyway, point is it
was one of those things where
that education, like that
unlock, it was, felt more like
a gateway, made me go, "Wait
a minute, so, like, the market
has a lot of demand and not
enough supply?" And it sounds
stupid when I'm saying it now.
Yeah.
But 18-year-old Will- Uh-huh
his head was exploding.
Yeah.
I was like, "Wait, so I
could, like, supply more
stuff and people will give
me money for it," right?
Yeah.
And I was like,
"
Done." My dreams
have all come true.
Right, right.
And so, but what was interesting
was that I was a theater major.
I clearly had, like, I did
not go to school, like,
as a, as a business major.
Yeah.
How'd you- Like, I thought I
was gonna go make movies or
something, which would've been
really cool … turn the wrong
way on campus one day?
How'd you end up
in an econ class?
Yeah,
exactly, right?
And so anyway, my point is I
think we have this idea that
there's this schooling, like,
all this prep that gets into it.
Yeah.
But the reason that you and I
have such a significant amount
of practicing domain knowledge
in completely different
careers- Yes … right, is
because we actually did them.
We didn't say, "Oh, well,
I'm, I'm marketing, guys,
so I guess I couldn't
possibly code anything."
Yeah, yep.
Right?
Like- Could- don't need to
understand finance at all
because numbers, you know?
Like…
Right, right.
Yeah.
Like, what fascinates me,
and this is really what I,
what I wanna dig in on for a
second, is how extensible we
are as humans, push ourselves
or allow ourselves to be.
Okay?
So let me, let me, let me build
on that a little bit more.
So imagine here I am
19-year-old Will, and at
that time I have no skills
whatsoever, or so I think.
I don't have any learned skills.
My market rate was
$5 an hour, right?
So it's not the market was
rewarding me for anything.
But it turned out that there
was a ton of stuff that I was
good at- But I hadn't tried.
Yeah.
I- this always fascinates
me, by the way, 'cause
I'm like, what if I am a
world-class concert pianist,
but I've never been given
the opportunity to find out?
Yeah.
Like, like, don't you find
it's kind of convenient
that the people that go
on to become, like, these,
these world-class whatever-
Yeah … often are groomed
from families that did- Yes
… specifically that, right?
Yeah.
Like, come on, right?
Like- As if they have the
corner on the market for
growing pianists, right?
Like, come on.
Yeah, that's what I'm saying,
right?
Don't you find that, like,
a, a little bit coincidental?
Definitely.
Which, which implies that that
resident experience and talent
can exist in any of us if we
allow ourselves to unlock it.
So fast-forward five, six
years later, and now I'm
running a pretty large company.
Yeah.
Right?
And I remember thinking to
myself, "How did this happen?"
Yeah.
Right?
I mean, like, like how was it
that with no training, with no
experience, with no anything, I
was able to excel at this level?
And here's the answer:
because I just did it.
You did it.
Yeah.
Right?
And that sounds trite, but
that actually is the answer.
Like, the reason I was able to,
to be a CEO and all these things
at a young age is 'cause I was
willing to just do it and not
sit around thinking about it.
You know what I mean?
Yeah.
There was this quote, and I,
and look, I am always careful
with these things because
they can be misleading.
Are you gonna do it in a voice?
I wasn't going to.
Now maybe I shall.
Let me think about it.
I'm not gonna
remember it exactly.
It was essentially the, the
world stands aside for they
who know where they're going.
But as founders, we don't always
necessarily know where we're
going, but more importantly,
the world stands aside when
people start going, right?
When you start moving.
Yep.
Yep.
When you start moving, people
start to get out of the way.
Things start to
congeal around you.
Things start to happen.
Things start to mold to what
you're trying to make happen,
as opposed to when you're just
sitting still, just thinking,
just planning, lots is changing,
but nothing is changing around
you necessarily, and I think
that's, that's really important.
A- and I wanna back up for
a second 'cause I love this,
this last d- part of the
discussion around this massive
amount of domain expertise
we have, and it is true, and
I like, I, it's crazy to get
into a group of founders.
Like, get seven or eight
founders in a room and,
like, I dare you to find
something that nobody's done
or hasn't tried or doesn't
understand something about.
You can have a conversation
about damn near anything
you want at a pretty-
Right … high level.
But I think it's important
for us to go, but it wasn't
always like that, and it
certainly wasn't like that
when we started, right?
And I think that's the
important part here.
The reason that that is true
isn't because we're a bunch of
know-it-all polymaths, right?
It was because we didn't know
stuff, but we didn't let that
stop us, and by not stopping,
now we know stuff, right?
Yep.
So the knowing stuff is the
by-product of the doing.
It isn't that we were able to do
because we knew a bunch of shit.
We didn't… I knew
shit when I started.
I knew jack shit when I started.
L-
let's unpack that some more.
Yeah.
Because the only way
to learn is to fail.
Yes.
And planning is typically
trying to avoid failure,
which sounds wonderful.
Isn't that funny?
It sounds wonderful, right?
It does.
It doesn't work- Yeah … but
it sounds wonderful, right?
Yeah.
It sounds like something
you would want to do
and you'd want to avoid.
Now, we spend time, you and
I, planning all the time.
Yes.
But here's the difference.
We plan with failure
as part of the method.
Yes.
We launch a landing page
series, and we're like,
there's no version we're like,
"Oh, my God. We got to plan
to make sure it's perfect."
Uh-huh.
We do our best.
Yep.
Right?
But we know that it's
going to fail, but
we're okay with it- Yep
because, um, we'd prefer it
didn't, but we understand when
it does, that helps direct
us, okay?
Now we know what to do.
Before that, it's purely
a theoretical exercise.
Correct.
If I'm sitting around, you and I
can beat up a landing page path.
Yep.
We can beat it up, and we can
go, okay, as much sense as we
can make out of it right now,
and luckily, we get to that
pretty quickly at this point.
But you can spend lots-
Yep … of time doing that.
The reality is it's
all theoretical.
It is all theoretical
up until that point,
until you release it.
Then once you start to see
where it fails, now you
know exactly what to fix.
Right, right.
It's like building a
sandcastle at the beach, right?
You don't know which part of
the wall to reinforce until the
waves start to crash, and then
you're like, "Okay, we got to…
More sand here, Jack.
More sand there, Hannah," right?
You have to start to plug
the holes, but you can't see
the holes during planning.
The holes appear during
actual market action.
I would also argue that
planning is a weak way to learn.
And now, this isn't an-
Yeah … anti-planning ra- rant.
Or anti-learning,
yeah.
Yeah, yeah, exactly.
This is more about you
can't plan your way
into the launch, right?
No.
Yes, by all means,
do some planning.
But when you're not launching,
every day that goes by where
you are not in the market-
Learning from failure.
And that failure comes
in so many forms.
It's comes in how, how
the market reacts to your
product, how investors
react to your pitch- Yeah
how staff reacts to your
shitty leadership style.
Yeah.
Right?
Like, all of these
things, right?
Yep.
These are all the
things you need.
These aren't the things
that you're trying to avoid.
No.
Now, of course, like, you,
it'd be great if you just
built the perfect product
and ev- investor said yes
and everybody that works with
you loves you, but that's
just not the way this works.
And frankly, the only way
you get to the point where
those things start to
click is by failure, right?
Yeah.
And people hate that, because
we are fundamentally conditioned
to avoid failure, right?
Like, you have to get an A on
the test the first time- Yeah
… or you don't get the grade.
Right.
See, if we took tests, like, you
know, if we were grown up, if
you will, through the academic
system the way you're supposed
to be grown up as a founder,
we wouldn't study at all.
Nope.
You would take the test,
you would fail miserably,
you would learn from what
grades you didn't get right,
and you'd take it again.
Yeah.
And you'd fail miserably
again, and you'd keep taking
it until you understood.
Boy, that certainly sound
dangerously like fairly accurate
and useful educational reform.
Well…
Yeah, I, I know.
Imagine that.
Let's stay away from that.
The idea is because you only
get one shot at it, your
studying and your preparation-
Yeah … are the ke- the
essential ingredient, right?
Yeah,
yeah.
But startups don't
work that way.
No, they don't.
It's also a case where you don't
know what the right answer is.
You can't study for it.
Dude, the failure is… It's
so hard, 'cause we watch
founders do this all the time.
They try to avoid failure.
They pause.
They're like, "We're gonna…
more, one more feature, one
more twist, one more that,
one more whatever." Yep.
And you and I are sitting there
going, avoiding failure is
literally trying to avoid the
very mechanism that creates the
answer to this question, right?
This is where the
answer comes from.
And I think, man, the, the
more time goes by, the more
I, I, I see it clearly.
Like, the founders who we
see doing the best, that
is a subjective thing, but
the ones that we see moving
fastest, moving smoothest,
like, just actually getting
stuff done, building great
businesses, aren't the ones
who are failing less at all.
They're the ones
who are metabolizing
failure faster, right?
Yeah.
They are able to
just go out, repeat.
I'm looking at more as, like,
fault tolerance than failure.
Failure is pretty specific,
and it means that it didn't
work at all in a lot of cases.
Sometimes that is true, but more
often what we're dealing with
is just fault tolerance, right?
Which is like, okay, that didn't
do as much of what we want it to
do, or that didn't work as fast
as we wanted, we didn't make
as much money, or that didn't
solve the problem in the way
that the- the- the user wanted.
Most of the time it's not
truly failure, it's just,
it's not adequately reaching
the mark that we want it
to, which I guess could
be couched as failure.
But I don't know.
I'm trying to put a nicer spin
on it so people not to feel
like they have to fail, because
apparently there is resistance
to failure, so I'm just trying
to take that off the table.
Think of how many aspects of
our lives where, that have
conditioned us to avoid failure.
For example, again-
Pretty much all
the rest of them … we'll
go back to academics, right?
E- exactly.
Academics are not conditioned
around try as many times as
you can in different versions.
Yeah.
And only by trying will
you get an A, right?
In o- in other words, only by
experimenting will you get an
A. Like, in this case it's no,
if you remember this specific
answer and you recite it at
this specific time, you win.
Yeah.
It's just that simple.
And if, if you follow that
formula, you win every time.
This doesn't have that formula.
Right.
Or let's take it to a job.
You go get employed for a job.
There's no version where they're
like, "Hey, junior doctor, just
experiment around a little.
Cut some stuff up.
See, see who dies, see who
lives, and like, you know, kind
of see if you can figure out
who should stay and
who should get cut."
That is sort of how
medicine started, but yes.
Yeah, well, yeah.
It's how medicine's
still running.
As kids, when we're, we're
growing up with parents, it's
the moment you do something
wrong, it's slap on the hand,
you know, metaphorically,
and you're just constantly,
like, gun-shy about doing
something wrong- Yeah, yeah
because you're constantly
penalized for doing anything
but what's right And then all
of a sudden, for the first
time, someone's like, "None of
what you learn, none of your
construct applies here," and
you just don't believe it.
You're like, "Wait, I can
just do whatever I want at
my own pace, and if it goes
wrong, I'll learn more?"
Yes.
Yes.
Okay, that makes no
sense whatsoever, right?
Yes, because everything
you've learned- Yeah … has
been pointed toward a
different construct, and
here's the difference.
Up until now, everything that
you've tried to do, whether it
was grow up as a human, whether
it was get a job, whether it
was go through academia, et
cetera, had a right answer.
This does not have
a right answer.
The right answer has to be
discovered through failure.
You have to make enough bad
product decisions to find
out what the good one is.
You have to make enough bad
investor pitches to find out
what the right, uh, model is.
You have to hire enough
of the wrong people- Yep
to find out who the
right people are.
Yep.
Right?
Like, it would be so cool if
you could just go through life
and only make good decisions
because you planned so well.
The way you know that your
spouse is the right one
for you is because you
had so many shitty spouses
or partners before that,
and you're like, "Damn."
One last anecdote.
I had three girlfriends before
my wife, not at the same time.
And in each case, right,
like- Good distinction.
Good distinction … I
had long-term girlfriends.
Yeah, yeah.
Like, they went okay.
I'm like a pretty easygoing
guy, but like, but there
was always some issue.
And so I always assumed that
in a relationship, you just
argue all the time, right?
I just assume, like, people
get shitty and, like,
snippy or whatever, right?
So in my mind, because
that's the only experience
I had, I assume that's
how relationships work.
And then I met my wife,
and we don't ever argue.
Uh-huh.
Like, it doesn't
even occur to me.
Like, if my wife said something
crass to me, not like in a
joking way, but like, like
actually meant it- Yeah
I would be so
fundamentally confused.
Right?
And we've been together
for 20 years- Yeah … so
it's not like, you know,
this is a new thing.
Yeah, it's not like the
opportunity hasn't arisen.
Yeah, ex- oh my God,
right, and we're both
very Type A personalities.
So it, it's not like
either of us are, are coy
about our feelings, right?
Yeah, yeah.
But what I'm saying is, until
you get out there and you meet
enough spouses, this could,
uh, this is about people
really, co-founders- Could
be co-founders, could be, yep
… could be coworkers- Yep … and
partners and whatever, you don't
really understand that you kinda
gotta crack a bunch of eggs-
Yeah
…
you know, break a bunch of
eggs, before you find the
one that you're looking for.
Yep.
Right?
And I think people are
terrified of that notion.
"No, I just wanna find
exactly the right person."
Yeah.
Good luck with that.
It's so funny because that
attitude, that mentality, is
actually what almost guarantees
you, you won't find what you're,
you're looking for, right?
At some point- Right … you
have to realize that the
failure is the structural steel
that becomes the scaffolding
for, like, everything that we
build from that point forward.
You gotta get, you
gotta know those things.
That's what sets the limits.
That's what sets the tolerances.
That's what sets the,
the, the min and the max.
And then you can actually
start to understand how you
operate within that system.
And until then, you're,
you're just guessing.
I think science tells
us exactly how good we
are at guessing, right?
We're gonna get it right
less than half the time.
Which is fine.
Here's where I would
say, I, I'm kinda tongue
in cheek saying this.
Here's where I really
want people to wait and
plan as long as possible.
When they're my competition.
I want my competition- Oh, yeah.
… to spend as much time on
the whiteboard- We love it.
Yes … as much time getting
their degree, as much time
as, as they can making sure
all their ducks are in a
row before they launch.
Yeah.
Please, competition-
Yes … keep doing that.
Because while you're doing that,
I'm gonna be actually building.
I'm gonna be getting
the customers you're
just talking about- Yeah
on a whiteboard, right?
I'm gonna be raising
the capital, I'm gonna
be recruiting the team.
We're gonna be out here
turning signal into revenue
while you guys are polishing
degrees and theories.
Fantastic.
Yeah, yeah.
Good luck with that, right?
And the reason I say that is you
don't wanna be my competition
in this scenario, right?
Yeah.
Like, you don't wanna be
the person that's sitting on
the sideline contemplating-
… while the actual person
who's gonna make this happen
is- Yeah … out there
making it happen, right?
It like, again, this goes
back to the cost of waiting.
Yeah.
The cost of waiting
is, is to be the person
that got sidelined- Yes.
Yeah
…
by the person that didn't
sit around waiting.
I mean, it's, it's
significant, you know?
Yeah.
No, it's, it's absolutely true.
No, like, it really does.
Like, it, startups don't reward
planning in that way, right?
They don't reward- At
all … preparation.
They reward- Right … action.
They reward motion.
Now, motion without any
planning, without any thought,
without any idea, like
you're just kicking up dust.
When the dust settles-
Yeah … if nothing's changed,
then also nothing happens.
So y- sure.
Sure.
But I think, you know, if I
have to pick one end of the
spectrum that I'm gonna lean
towards, there's, there's
somebody who's out there doing
stuff, and there's the other
person, you're asking, "What
have you launched so far?"
And they're like, "Lots
of finger tents," right?
Lots of pinning.
Great.
Okay, cool.
How's that going?
Yeah, yeah.
We're not an
industry of planners.
And again- No … this
isn't anti-planning.
Just, just to be clear, just
to, to, to give you a sense
for, like we own bizplan.com
that we've run for 20 years.
It's literally a business
planning tool that we built-
Yep countless copies of, right?
Clearly we think that there's
something to planning, but
not at the expense of action.
Right.
Planning never happens
at the expense of action.
Planning is something
that is supported-
Should create action.
It should create action.
You should plan enough to know
what to do next, and you should
not plan any further than that.
Correct.
And, and I think the reason
this should be a massive sigh
of relief for so many founders
is because they're saying
they're going, "Well, if I
just get to this point, again,
if I get the degree, if I get
the cash, you know, once I get
married," you know, you name it.
Whatever this, this made
up milestone is, here's the
great news: It doesn't matter.
Yeah.
It doesn't make a
lick of difference.
None of those milestones,
no matter how much you think
otherwise, are gonna make a
lick of difference, and none
of them even remotely compare
to actually taking action.
So I think if, if folks in
the audience are thinking,
they're on the fence, right?
You know, "Maybe I should
wait a little bit longer."
The biggest mistake you
can make right now is
waiting one more day.
Because you jump in tomorrow,
you start taking action, you
start learning, start learning
faster than your competition,
that's what's gonna drive
your company, not sitting
around and planning for it.
For all of us that are,
that are sitting around and
planning, we become the losers,
and later is for losers.
If you wanna win, get in
the game, get in right now.
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.