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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 joined
as always by Will Schroeder,
my friend, the founder
and CEO of startups.
com.
Will sometimes a lot of the
times, most of the time being
a founder feels like we're like
swinging and missing over and
over and over and over again.
But you know, the truth is
our careers aren't about
being consistently right in
like really big ways, right?
Like it's about, you know,
eventually connecting
with a bigger one, but
just as much about like.
Regularly connecting with the
small ones, like, and I know,
I know you want to share a
story today and, and like,
let's tee it off with that,
which is that, uh, Mark Cuban
once famously said, I think
it was basically just, you
only need to be right once.
Yeah, I may be off by
a word or two there.
So I'm not quoting that.
I'm paraphrasing Mark Cuban,
but that was the basic premise.
We got to be right.
Once and sometimes that doesn't
even mean a really big right.
It just means enough of
the right kind of right.
But I think that's interesting
because I don't think as
founders, uh, that we understand
how asymmetric our wins are.
The opposite of asymmetric.
Yeah, sequential whereby
we show up at a job coming
out of college and we keep
working that job and every
year we get paid more.
Right.
Just this kind of sequential
compounding style of success.
As folks know, this is
nothing like that, right?
Just like you could go 10
years working at this thing
and actually have less
money than when you started.
Quite frequently the outcome.
Exactly.
And we're in this
interesting thing where
we have our whole career.
Let's say like our professional
active career could span
50 years reasonably, right?
At any time in that 50 years,
we could have our moment.
The problem is we don't know
what it is, but I think, I think
there's like a false narrative.
That's like, well, if I haven't
hit it by the time I'm 25 or
30, which is usually only like
relegated to people that are
that age, that things like
that, that I'll never hit it.
And so I think let's dig into
how wrong that is, like how
really in this business, you
only need to be right once at.
Any point in the timeline at
any point in the timeline,
so we mentioned Cuban, okay?
So a lot of people don't
actually know, remember,
or care where Mark Cuban
actually made all his money.
They hear he's a billionaire.
Yeah, he owns the Mavericks.
Yeah, exactly, exactly, right?
I don't know.
But I bet if you ask the
average person on the street,
how did he make his money?
How did he become a billionaire?
They can't tell you.
Yeah.
And here's why.
Mark Cuban made all of
his money in 1998 when a
company called broadcast.
com, a company you've never
heard of went public and
then essentially got sold
to Yahoo a year later.
So for 5.
7 billion,
which by the way, at that
time, like for a startup
company, that, that was.
A banana's valuation.
I mean, it's
crazy now, back then,
that was unheard of, okay?
Now, just real quick,
because I love, I love,
uh, internet history.
So, with Broadcast.
com, Cuban wasn't, he
didn't even start Broadcast.
com, until he was 37 years old.
Okay, now I, I think
that's interesting because
a lot of people think
like, Oh, he was probably
24 and blah, blah, blah.
No, he
wasn't a 37 year old in
the dorm room, I hope.
Yeah, exactly.
And where I think this is
interesting is a lot of folks,
specifically folks that are
37, are like, oh, I'm later
in my career, it's too late.
It's like, dude, this guy,
like, the biggest, most
important decision he made
wasn't until after he was 37.
Now, fortunately, because he
just hit at exactly the right
time, which is part of this, he
ends up selling again, you know,
his stake, he had a co founder,
but his stake in this wildly.
Overblown valuation to Yahoo,
which at the time was one of
the few, like, companies that
survived the dot com crash
and everything else like
that, so the money was good.
But by the time Cuban
became a billionaire,
he was 41 years old.
Now, Ryan, what did we
say the vintage was?
99 ish?
98, 99 that that happened?
It IPO'd in 98, I think, and
then Yahoo did the buyout in 99.
Okay, well, let's
stick
with that.
25 years ago.
25 years ago.
Now here's what's even more
interesting than the fact
that he was 41, let's say
that he became a billionaire.
He's been a billionaire
for 25 years.
Yeah, that's one of those
things they don't tell you,
right, like never rest on your
laurels or you can't rest on
your laurels unless they're 5.
7 billion worth of
laurels, then you can
rest on them for a while.
You can actually sit on that
for a good amount of time.
Now the reason we chose
Mark Cuban as the person
to kind of like feature
around this is because Cuban
has clearly been Wildly
active in investing, right?
I mean, he made actually a great
investment in the Mavericks
which which worked out Okay,
but definitely didn't have
the kind of payday that he had
before that and you know, he's
obviously famously on Shark
Tank So he's investing tons
of stuff now to be fair for
folks that aren't aware Shark
Tank investments are generally
like the worst investments ever
and they all tend to fail And
most of those deals never get
done and I, I love shark tank.
So I'm not knocking it.
I'm just saying like, yeah,
there's no way Mark was going
to get rich on that one.
But my point is he's a
very active investor, Ryan.
I don't know if you know this,
Mark Cuban is in our cap table.
So yeah, yeah.
He's been in there
since clarity.
Yeah.
Yeah.
He invested in clarity.
Every time we have an investor
relations meeting, I
expect Mark to be there.
And he, he never is
like, I always call it.
I'm like, Mark, are you, are you
on the call Mark right here now?
And, Mark, I can guarantee
you're not going to make
another billion dollars from us.
Not off that one.
Just locking that in now.
Anyway, so, here he is, this
wildly successful founder,
and he makes, you know,
over a billion dollars.
He's 41 years old.
Now he has 25 years since
then to do any deal you could
possibly imagine, right?
The guy's wildly connected,
wildly active, etc. And has
never done it again since.
All the resources you could
possibly need, right?
Exactly, right?
Why?
Why hasn't he done it again?
And why, generally speaking,
do most people never, ever,
ever repeat the success that
they had in any capacity?
I think that's There's a lot
of randomness involved, right?
There's a lot of chance
particle collision that
makes these things happen.
Dig into that.
When you think about how random
it is, what comes to mind?
The lottery, right?
Like, you don't, you don't ever
hear anybody worrying about
something like, hey, how do we
become a three peat lottery?
And we're like, oh,
you've only done it
once, you failure, right?
Well, I didn't really have
that much to doing it in
the first place, right?
It wasn't really
something I did.
Uh, and so therefore, yeah,
it's, it's, look, it's
not quite that random.
And I think that there is
something else important.
I know we're going to get
put a little bit later, uh,
but it's, it's the fact that.
Success at this level is very
rare, but success within a
startup doesn't have to be
success at this level, right?
You don't have to be
that right, right?
Mark Cuban was right
once at that level.
He's also been right on a lot
of other things that would have
also made him wealthy enough.
Yep.
We can argue about whether he
could have done that without
the resources from the first
really, really right or not.
But that's what it
comes down to, right?
It's the, that level
of rightness requires.
a lot of good fortune, really
incredible timing, most of which
is actually out of your control,
right place, right time, right
idea, right level of input and
kind of tenacity and sticking
to it and just being around long
enough so that you are there
at that right moment, right?
Right.
And
you know, part of it
too is understanding.
I think this is the hardest
thing for a lot of folks is
understanding that we are in a
wildly asymmetrical business.
Like I mentioned before, which
means We don't have like year
over year consistent wins.
It's just generally
not how, how it works.
We have lots of usually
losses and misses and
failures, which then lead to.
One, hopefully, you know,
one phenomenal win, but the
reality is we don't know when
that that win is going to
come, if it's going to come
right, if yeah,
that's, that's it, if
right, right.
And so that when isn't just in
our career, it's when in the
startup, the startup hit that
level of trajectory, right?
So like you could be in
year six of your startup.
And it's doing two
million in ARR, and you're
just getting by, right?
You have just enough cash
just to pay people, and
you're just getting by.
And you're thinking, ah, well,
that was my shot, I missed
it, etc. Maybe, or, maybe your
hit isn't going to come until
year 14.
I think that's the real
misconception here, is that
there's sort of two paths.
One is this sort of stacked
linear geometric growth, like
where it's just like, you know,
we just grew year over year
over year and I understand
how compounding math works.
And so eventually we get big
just by every year growing
a little bit bigger, right?
Or there's the, we,
we start, we pitch the
idea, we go get funded.
And somehow in the first
three to four years, we
have this crazy, crazy
spike that crazy spike.
Can never come.
It could come in the
first three years.
It could come in year 12, right?
It's again that that that
level of success is Incredibly
reliant on the principles
of chaos and randomness
That's what I'm saying.
And I think that's the hard
thing for us to wrap our heads
around, you know We're like,
well, it wasn't successful in
the first three years like some
of these things are so I guess
that's it I guess you know it
we missed and maybe that's true.
You know, maybe you actually
missed or Maybe the business
you are building takes 15
years to hit that, that metric.
And that's fine too.
Now again, can you
survive that long?
Do you have the capital?
Do you have the, you
know, the resources?
Maybe not.
But what I think is interesting
is that for a lot of
founders, we have this feeling
like this one must be it.
It's like, no, dude,
like this is one of many.
Right?
Like hopefully, you know, if
you're so fortunate, you start
one startup and that's your
hit actually, to be fair, that
happened to me, to be fair,
that happened to me, right?
Like the first startup I started
did extraordinarily well.
And if I'm being honest,
I've never built anything
bigger since, which is
ironic because like it was my
biggest.
Like,
I have exponentially more
experience, more resources,
more cash than I had back then.
Yeah.
And I've never been
able to replicate like
that level of growth.
Now, there's some things I
didn't want to replicate,
but, but, but that's,
that's over there.
Right?
Absolutely.
Yeah.
Yeah.
I can't say it was my
big, biggest success in,
in all regards, but it
was the biggest payout.
Now, what was also interesting
about that though, about
that first success is that it
set up all my other success.
And I feel like folks
don't really understand
how valuable a base hit
early in the game can be.
And a base hit means either a
business that became profitable,
and you can, you know, kind
of leverage those profits,
or you had some sort of, you
know, small windfall, etc.
You'll hear something like, ah,
well, they only made 200, 000.
So, you know, It
wasn't a big hit.
Yes, but would you
say no to 200, 000?
Wait, no, no, no, but I think
what's interesting is we're
so hyper focused that this is
going to be the runaway hit,
especially early in our careers.
We don't realize how valuable
a base hit could be to
our overall trajectory.
Let's, let's go back to, let's
go back to Cuban for a second.
What a lot of people
don't know, cause I don't
even know what broadcast.
com was, is that.
Cubans sold a business, I
think when he was like 24
or 25, like pretty early,
for 6 million dollars.
Like, way earlier than
that, almost like, like
10 15 years before that.
Which gave him the latitude
to be able to make some bets
that could become a broadcast.
com, right?
And that's what I think is
fascinating, like, early in
my career, I made some money
so I could pay off my debts.
Right?
So that I, I wouldn't have to,
uh, constantly, you know, be
servicing all the debts that
people tend to have in life.
Which set me up to be able
to make other bets, right,
that I would have never
been able to make if I was
servicing all those debts.
And, and I, I think those,
those small hits, if you
will, give you that luxury.
Those small hits, while
they don't seem like a big
deal at the time, that they
don't let you retire, they
set up the fact that you can
do things and make swings
that could be the big hits.
How do you see it in
terms of small hits?
Right?
So there's, there's that version
of a small hit, which is a
couple million dollar exit or
500, 000 exit, whatever it is
you, you, you pay off your debt.
What about the small hits
that are just ongoing?
Are we talking just about
small, but still relatively
significant kind of one off hits
or the accumulation of just.
Every year we're able to
put a little away or every
year we chip away at this.
Are we drawing a
distinction there?
Are you, are you saying that
like kind of doesn't matter?
You know, what's interesting
is I remember having this
conversation, uh, with a really
successful founder years ago.
And we were talking about
like, what was the inflection
point in our careers where we
got the most amount of like
value out of life, if you will.
Let me be specific.
I felt like when I was able
to put 20, 000 in the bank,
Mind you I'm like 21 years old
time, but when I was able to
put 20, 000 in the bank that
probably Impacted 80 percent
of my life going forward.
And a lot of people like
they're like 20, 000
bullshit, blah, blah, like,
no, you don't understand.
It's all relative man.
It depends on where you are.
Like would, would 20, 000, if
you had 0 right now, would 20,
000 set you up for a long period
of time based on your life?
Now, probably not.
You've got, you've got family,
kids, lots of stuff going on.
But at that time.
It was a big deal, right?
Like you said, it's
the inflection point.
It sets a new baseline, right?
The foundation just got
a little bit broader.
Well, let me be specific
when people hear that their
immediate reaction is, well,
you know, I can't pay bills
and retire in 20 K. That's not
what I'm talking about at all.
Right.
What I'm saying is being able
to keep playing baseball.
Exactly.
Right.
Like, yes, I needed
active income.
I wasn't gonna
retire in 20, 000.
Um, but once I had 24,
yeah, yeah, yeah, yeah.
Like once I had 20, 000 in
the bank, I could take a
swing at something, and if
I missed, which I would, I
had just enough cash to get
back to the plate, right?
When you don't have that
cash, and the miss is game
over, go back to, you know,
Best Buy or wherever you
were working before, then
that's a game changer.
It's, it's an extra life.
Go, let's switch off sports
analogies for a minute.
You're, you're, we're
video gamers now.
You've got an extra life, right?
So I can survive, I can survive
a startup death and come
back and keep going, right?
Like we can, we
can miss payroll.
We can lose a client.
We can get sued,
whatever it might be.
We now have a 20k buffer
between us and the abyss.
It was interesting because early
in my career, like my expenses
were stupid low because I was
coming out of college, right?
But I, I bought a
house, uh, back in 1997.
seven, give or take, and I
spent 167, 000 in that house.
Now, uh, when people hear
that now, I mean, you got
to understand that was
a long time ago, right?
So like that, that same house
was probably worth three
to four times that, that
amount now in today's terms.
So just, you know, do the math.
But that's how much I
spent on it back then.
Right?
And that was all the
money in the world to me.
I was living in a campus
apartment prior to that.
So like, and my rent
was 250 a month.
So like, relative to where I
was, that was a big expenditure.
However, I was able to
get in front of that debt.
I was able to pay
off my college debt.
I was able to pay off my house.
I was able to pay off my car.
So I had no debt.
So I've essentially had next
to no debt for almost 30 years.
Now, That has a
compounding effect too.
That's what I'm saying.
What people don't understand
is they're like, Oh, you have
to make millions of dollars
to have these opportunities.
You don't.
You don't need to have
thousands of dollars
spent in the right places.
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.
It's funny because I think
that in, in a lot of ways.
Founders think of like the small
wins as stepping stones, right?
That they somehow need to lead
to bigger and bigger wins.
Yep.
Or if we're not gaining,
like the size of the
wind doesn't change.
If I just keep having the same
size win over and over and over
again, it's not a good thing.
I would, I think we would
both disagree with that, uh,
patently, but on the other
side of it, I think that it's.
It's, they are more
than stepping stones.
Yes, they're stepping.
So if you just keep repeating
them, they're there, they
have their own value, but
it's that safety net, right?
It's right.
It's what it buys you, right?
And it's not just a stepping
stone towards the next step.
It's it enables that step in
and of its own, right, right
again, because you now have
this buffer between you and just
not being able to play anymore.
Right.
What was it?
Gretzky said, I miss a
hundred percent of the shots.
I don't take.
Right.
Right.
Same thing.
Like if we're, if we're not
out there, if we're not in
the startup game, like there
is no chance at a big outcome
if we're not playing at all.
You bet.
And so I think that that's
what these, these small,
tiny, geometric, sequential
wins bias the ability to be
around for the bigger one.
That's what I think
is interesting because
again, people are saying,
Hey, you know, I need to
have this massive win.
I'm working at this startup
and it's not going to
have this massive outcome.
And I'm like, I get it.
But will it get you on base?
Will it give you some
breathing room so you can take
a bigger swing after that?
If so, it's a win.
Because I think if all we
try to do is optimize for
I'm gonna do this one thing
and it's gonna be the total
cash out and I'll never have
to do anything else again.
You're
likely gonna fail.
Right.
Refer to our previous episode
optimized for the, the, the,
the probability of the outcome,
not just the size of the outcome
we, you and I spent almost an
hour on that one because it's,
it's so absolutely valuable
to understand that as startup
founders that you really do
need to think through like,
yes, yeah, a big one is great.
Right.
But if your probability
of hitting that massive
win is, is really low.
And the probability of getting
any base hits or smaller wins
because of the way you're
thinking, because of the way
you're approaching business,
because you're aiming for
that big, big, big win, right?
It's that thing that my dad
used to say, you know, aim
for the moon, sure, but keep
clearing the fence, right?
Because if you just
consistently clear the fence.
You can keep clearing the
fence, even if you never
get to the moon, something
good still came out of it.
Right.
But I think that when we, when
we go all the way, let's shift
gears for a second and go back
to something we were talking
about before a little bit,
which is that we often think
like this has to happen by our
twenties or our thirties, or
it's never going to happen.
Right.
Right.
Right.
Let's talk about like, when
does this actually happen?
Right.
When, when, when does it occur?
And, and when too late,
is there too early?
Right.
What, what happens here?
And I think you, you and I
were talking before the show, a
couple of additional examples.
Walton comes to
mind, Sam Walton.
Right?
Right.
How old was he when
he started Walmart?
Over 40 Reed Hoffman from
LinkedIn was over 40.
Yep.
Warren Buffett made 99
percent of his net worth
after 50 It also helps to
start as Warren Buffett at
50, but but but this is a
young person's game
Step one live to a hundred
step to become Warren Buffett.
What's interesting is there
is an Incredible and I I
had it maybe you did too an
incredible bias to believing
that our success If it's going
to happen, it's going to happen
at an inordinately young age.
It wasn't
necessarily that I
thought it was going to
happen at a young age.
But I did believe that I
would have a lot more to
do with the win, the timing
of it than I actually did.
Right?
I thought it wasn't necessarily
that I was young, I did,
but that was relative to
how old I was at the time.
And it was more so that like,
I was going to have a lot to
say about the timing of it.
Right, right.
Well,
I mean, that goes back to
the Cuban thing, right?
Yeah, the guy's been a
billionaire for 25 years, right?
Yeah, obviously he has the
wherewithal to do what he
did before again It just
doesn't work like that.
It's like like Bill Gates is
one of the most successful
entrepreneurs in history He's
never built a second Microsoft.
Yeah, right like in the reason
for that is Is because it's damn
near impossible to replicate,
to kind of like falsely
build, if you will, fate.
Yeah.
Right?
Like, like, some of this,
and I don't believe in luck.
I, I, I, when it comes
to entrepreneurs, I do
not believe in luck.
Good, good fortune
is the closest we can get.
Good fortune, right?
Timing matters, right?
Like, doing the right thing
at the right time matters.
There's a lot of businesses
that had I built it at
a different time it just
simply wouldn't have worked.
And there's businesses that I
did build at the wrong time.
Again, we go back to
Affordit versus Affirm.
That would work
pretty well right
now.
For all the other
businesses that are
killing it in that space.
And so, there's a lot of
factors that go into it.
What I think is interesting
is, when I talk to people
earlier in their careers, in
their 20s and 30s specifically,
they have a bit of a sense
that, like, this is it.
Like, if I haven't nailed
it by this point, I
must be out of the game.
And I gotta say, that
mentality is fairly new.
And in, you know,
let's rewind back.
Really, I think the internet
era, the startup internet
era, ushered in this
expectation of young wealth.
Of, I can be exponentially
wealthy at a very young age.
Because, what I always thought
was interesting is, in the,
in the early 90s, when I
was kind of growing up in my
career, and, uh, I remember
I was just buried in Forbes
magazine, Fortune magazine.
Yeah.
And it was all these
silver haired foxes.
I was gonna say, yeah,
wasn't anybody that didn't
have wrinkles on the cover?
It was all these folks that
were like, the, the new
young gun at IBM is now 57.
And there was this expectation,
now most of this of course is,
you know, more sequential kind
of corporate ladder stuff,
but there was this expectation
that much later in your career
you had all the success, but
then internet came around.
And internet threw everything
off, and I know people are
gonna say, Oh, prior to
that you had Bill Gates and
Steve Jobs and Mike Dillon.
Yes, sort of.
And four other people.
Yeah, right, right.
But those were total freak
outliers that nobody, There
was no pattern to it that
anybody was expecting.
Here's one, man.
Just think about it this way.
In that same period of time, how
many lottery winners were there?
Far more than there were people
who did that with business
and the odds of the lottery
are like 220 million to one,
right?
You bet.
Okay.
There you go.
Yeah,
right
But like all of a sudden
in the 90s you had a lot
of pioneers of wealth that
were young Again, this is
kind of us dating ourselves,
but like Marc Andreessen
was my folk hero Right.
Mark Andreessen started
Netscape, had one of the most
successful IPOs, I think it
was 95 if my history is right.
Sounds right.
Um, and was on the cover
of Time Magazine back when
people read magazines.
And he was in a throne, right?
And it was like, this is it.
And I remember
when that came out.
And I remember seeing that.
And I remember thinking.
Everything's about to change.
You could
just feel it.
You could just feel it.
And it did.
And that gave way to like
the Mark Zuckerbergs.
You know, like the next
generation, etc. And I
remember there was a story
years ago where Zuckerberg met
Andreessen for the first time.
And I don't know if he was
just being sarcastic, except I
don't think he has that gear.
Mark Andreessen was explaining
that I had started a company
called Netscape, blah, blah,
blah, and Zuckerberg was
like, I've never heard of it.
Right.
And I just thought that
was like, like, that
might even be true.
It sounded like something he
would say, but like, I just
thought that was hilarious.
That this guy was like handing
over a mantle to the next guy.
And that was like, that'd
be interesting if it wasn't
truly sarcasm, that'd be
an interesting Harbinger
that AI will be capable of
that at some point then.
Mark can do
it.
Yeah, yeah, exactly.
And so I, you know, where
this gets interesting
is the expectation of.
I should be wildly
successful by 20 something.
I should be wildly successful.
That's fairly new
in our culture.
It is.
And I think that the thing
that I think it was both
exciting, that time was
super exciting, right?
It was, it was a wonderful
time to be alive.
It was a wonderful time
to be an entrepreneur.
And I loved most of it.
And interesting.
I'm trying to think now
back to some of the other
founders that I know, the
same vintage and then like the
generation immediately after.
I feel like it became
more of a problem for
the generation after.
Yeah, I feel like we came up
at a time where we were still
starting things and trying when
that still wasn't the narrative.
Yeah.
And the narrative changed.
I think for the people
that came after that, the
problem was, this wasn't just
something that was possible.
All right.
And like, you could be really
wealthy at this young age.
You'd have this massive
success at this young age.
Did that went from being
a Highly unplausible
possibility to the path, right?
Like it's Zucker die, right?
Like I gotta, I gotta do this
or like, or I'm not successful.
This became the new watermark
instead of the holy shit.
We landed on the
moon moment, right?
That's what it should have.
That's my point too.
Like, those outcomes
are such outliers.
Like, I specifically remember
when Instagram sold for a
billion dollars, and they
were like three years into it.
Yeah, yeah.
And I was like, oh, shit.
Yeah.
Right?
Like, now everyone's gonna think
that System, you just confused
everyone else on the planet now.
You just screwed it up.
Like Like that is such a
freakish outlier, right?
Like, yes, it did happen.
It doesn't mean it does happen.
And there's a dramatic
difference there.
And I think all of a sudden
expectations get out of whack.
And again, it
would be different.
If the line of corpses of
people that thought that was
true weren't so insanely long
and the line of people who
actually got to see it become
true were so insanely small.
And I think those expectations
have, have real consequences.
They do.
And let's stick on that for
a second, because I think one
of the consequences there is
there are a lot of businesses
that would still be around
that aren't simply because
they tried to push for that
super, super elevated track.
They're right.
We got to go, we got
an IPO in the next four
years or we're out.
And the vast majority of them
ended up on the latter half of
that, which is that they're out.
And so I often find myself
wondering, like, what if those
business had just stayed around?
What if they had just
enjoyed like a more linear
type of success and just
built really good product?
Where would we be now?
All right.
As, as a tech community, as,
as, as the founder community,
as the planet, like what would
have happened if less of those
had gone moonshot or else?
Right.
And just said,
build good business.
I'm, no way of ever knowing
that, but it is something
that I think about.
To be fair, that's how
most businesses operate.
Right.
I'm, I'm so fascinated by like,
you know, what we call the
small business, uh, community,
which is by the way, like 99
percent of businesses, right?
It's most, you know, we
are the freak show within
the world of building
businesses, not everybody else.
And, and when I think about
that, I often think about when
in, in 97, when we're, when I
was building my digital agency.
Uh, we connected up with
a traditional agency and
we merged the agencies.
Okay.
The traditional agency,
an agency called GSW had
been around for at least
20 years, like probably
longer, but at least 20 years
doing more or less the same
business for a long time.
Right.
They were like, maybe like
an eight to 10 million
business as far as billings.
Right.
And not terrible.
Right.
Good business for, for the,
the, for GSNW, you know, they
built great lives around it.
But that year, uh, in, in
97, you know, we had that
chance to pitch Eli Lilly.
Uh, we won a quarter billion
dollars a year worth of bill
billings, and that became
a very different business.
Yep.
There was the hockey stick.
For them, 20 plus years
into running their business.
And, and, here's what's funny.
Of the GS& W, the W's, uh,
Rick Weissheimer, he had
retired the year before,
because he had turned 55.
Holy shit.
That's way closer.
Wow.
That's scary.
Okay.
Um,
don't do the
comparative math there.
We'll you're way
younger than he is now
at the, at the time.
I'm like, are we putting up
a tombstone for this guy?
And I'm like, damn,
that's a few years away.
Anyway, my point is like, I
look at it and I'm like, those
guys, We're basically putting
themselves in a position
to have this you only need
to be right once moment by
being around that whole time.
Now, to be fair, they
were happier than hell.
Yeah.
How the business
had gone, right?
They were like, oh, this
sucks that we've been
running for 20 years, it's
not worth a billion dollars.
No.
They were like over the moon.
Yeah.
Right?
Living good lives.
Living great lives, right?
And planning for retirement,
you know, as you should.
But what's interesting to
me is that Because they kept
that longevity, it turned
out that year 21 would be
the year that would make
those guys worth hundreds of
millions of dollars, right?
And it blows my mind to
think about, like, how many
companies are like, Well,
we've been in this for two
years and it's not taking
off, so, you know, we're out.
Right?
Like, I guess it's
dead in the water.
Watertight yet.
Like, what are
you worried about?
And I think there's this, this,
this just broken narrative
that like good businesses
have to be good businesses
within the first few years.
Yeah.
As if, as if the velocity
to success is somehow
makes it more successful.
Right.
As if like, The, the pace at
which you get there, honestly,
do we care if Usain Bolt ran
that his, his top a hundred
meters at age 18 or at age 23?
No, it's a phenomenal
accomplishment regardless
of when that happens.
The pace at which you
get to your best year
ever matters a lot less.
Okay.
I would, if it's your last
year on the planet, you're
like, I finally did it.
Ah, you're gone.
Like, yeah, that
would kind of suck.
But like, let's, let's be real.
Like it doesn't matter.
How quickly you
get to that point.
Yeah, you get to
that point.
I agree.
And I guess what I'm saying is
like, I see a lot of businesses.
And this is really my point
where the business just
needed time to breathe, man.
Yeah, the business
just needed time.
Like, there's no way in year
one through five, it was
ever going to be the business
that was supposed to be.
It was never meant to be the
business it was supposed to be.
It's growing up, learning
what it needs to do.
Right, right.
Years 5 through 10.
Still, not the business
it was supposed to be in.
Now I'm not saying
this is every case.
I'm saying the fact that folks
don't even like, like give
it that timeline is bananas
to me because most of the
rest of the world absolutely
expects that timeline.
Weird tie all to this
together for just a second.
This is going to be funny.
Okay.
So on that note, you
got the GSW guys, right?
Like, so they built
a great agency.
It was a good agency
for a long time.
It was a great business had
nothing else ever happened.
They would have been
totally fine with that.
They led great lives.
They were on their
way to retirement.
They were happy people.
Cool.
They did not know that
there was going to become
a fundamental change in the
market that would allow that
business to grow that way.
Right.
Digital wasn't on their
mind because sometimes
it's not even just the fact
that we don't know when we
don't actually know what.
Yep.
Because 20 years ago when they
started, they can be like,
okay, we're going to run this
thing for 20 years, digital
is going to come around and
then we're going to hockey
stick up and then we're out.
Cool.
Cause they didn't
see that coming.
Sometimes your biggest successes
are really just kind of do come
out of nowhere, but by virtue
of still being around, you're
there to take advantage of that.
And here's where it gets tied
together and really funny.
Like I looked down at my
mug and I realized I'm
holding a lesson right now.
Do you, can you
see what that is?
The leaning tower,
leaning tower.
That was a fuck up.
Right.
This architect's claim
to fame was objectively
his worst build ever.
He didn't set out to do this.
He built a bad foundation.
The damn thing tipped over.
Right.
And that became his big win.
Arguably one of the most
recognizable buildings on the
planet that otherwise would
have just been a nondescript
tower that they would have
let fall down a long time ago.
Right.
Ironically.
It should have, and they've
kept it up at the ankle, right?
So like, you just don't know.
So in addition to just
like not knowing when, not
knowing what is actually
going to be the thing.
Like we can guess and we
can, obviously we, we need
goals and we're trying
to hit those things.
We're trying to create
outcomes, but we don't
necessarily know exactly what
else is going to come along.
Right?
Nobody was talking about
including AI in every part of
their business four years ago.
Now I can't talk to a
restauranteur who's not
like, here's how we're
trying to involve AI in
our onboarding process.
I'm like, you sell hot dogs.
Yep.
What are you talking about?
Like, you know,
with AI now, cool.
Right.
Didn't see that coming.
It's crazy.
Look, you can't predict.
No.
When your moment's going to be.
That's the whole point.
Right.
The point is being in the
game long enough to be
there when your moment,
if your moment comes.
Yes.
But if you're trying to force
feed it, if you're trying to
get a, give it an artificial
timeline, as if you have some
control over exactly when and
how that's going to happen.
Right.
At that big exit.
You're kidding yourself.
You're deluding yourself.
Nobody's been able to do it.
People have been able to build
companies that became great
things and that's awesome.
But no one's been able to
do it artificially despite
everything, so to speak, right?
And I think for, for founders,
if we really believe that we
want to hit our big asymmetric
moment, we just have to
consistently be in the game.
And sometimes it takes a really
long time and you know what?
It's worth it because again, all
we have to be in our career for
the entire longevity is right.
Exactly.
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