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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to another episode
of the startup therapy podcast.
This is Ryan Rutan joined as
always by Will Schroeder, the
founder and CEO of startups.
com.
Will, as startup founders, I
think we all sort of love to
romanticize the, what if it's
part and parcel with what we
do, but, but recently I give
it a couple of milestones
where you sat back a little
bit and really put some time
and thought into what if.
On the, what ifs, like, what if
I had done something different?
Like what it's, so it'd be
fun today just to kind of
walk through some of that.
Cause I think as founders, we
all face these things and it can
create a lot of consternation
can create a lot of regret.
And so let's, let's unpack
this and give people a
realistic view of what the F.
With the what ifs,
I think, I think people like
in our business and startups,
we are in the business of what
if, what if we had done this,
what if we had raised capital,
what if we had sold, what if we
had started early, what if, I
think it's fascinating because
for me personally, and Ryan,
you and I've talked about this
a lot in the past year, you
know, I just turned 50 in this
past year, which, which puts
me at over 30 years Of being
able to analyze the what ifs,
you know, at some point the
what ifs actually had a lot
of data points.
Yeah What data points and my
career is a little unusual
similar to yours in that all
we've really been have been
entrepreneurs We've been able
to look at so many different
points of life and be able
to say, you know I could
have gone left but I went
right and how did that go?
What's also interesting about
our perspective is we live
with everyone else's what ifs.
You know, we get to
live thousands of other
lives, lie on the wall
to lots of what
ifs you bet.
And so that gives us a unique
point of validation that most
founders, and certainly a lot
of the founders listening don't
get, which is for us, it'd be
like, Oh, I could have sold
and I would have been so happy.
Now we sold it, saw a
ton of people who sold
are miserable, right?
Like we get to see the what ifs.
I'm really fascinated
because this was unexpected.
When I turned 50, I, you know, I
took some time to just process.
And I do that every
year around my birthday.
You know, I just take some
time, process the past year.
Usually what I'm surprised
by is how much stuff
you can do in a year.
Right?
Like, I don't think
we give nearly enough.
That
was just a year ago, right?
Yeah.
Oh, that and that and that
and that happened this year?
Yeah.
You can live a
lifetime in a year.
Uh, depending on
how you spend it.
Anyway, so, uh, I was looking
back, you know, longer term for
the first time, a, a big, uh,
crux, and I was looking back 30
years more than 50 years, right?
Because I was looking
at my career years.
And one of the things that
surprised me, that I didn't
expect, didn't even see coming,
was how few what ifs I had.
Okay, so if, if I were to define
that, if I were to lay that out,
I would say that there's the
safe route and then there's the
what if, right, the blue pill,
red pill kind of situation,
right, and more often than
not, I always took the what
the hell, let's see what, let's
see where this ridiculous path
goes, I found that fascinating
that while that leads to all
kinds of trouble, I mean, by
definition it is not safe,
While it leads to all kinds of
trouble and it didn't always
end well, I mean, I would say
statistically it ended poorly
more than it ended well, but at
no point could I come up with
a lot of things in life, both
personally and professionally,
where I didn't roll the
dice, where I didn't take
that path and say, Screw it.
Let's see what happens.
Yeah.
So just hang on.
It's because for everybody
listening, people might
get a little confusing,
but you picked a path.
So there's the, what if
to the alternate, right?
I think what we're saying is
that in general, where it was
like the follow the standard
path or take this, take on
risk, take on, take on unknown.
You took on risk.
You took on unknown.
Right?
So what we're saying
is that while we don't
know exactly what if.
Will had gone to work for
Nationwide Insurance and
had a corner office and,
you know, just did the
nine to five career thing.
But we can guess a little bit
better at those what ifs because
it's what most people do, right?
So, so just for everybody
listening, that's what we're
comparing and contrasting
this to, uh, which is Will
with briefcase, uh, and,
and lots of polo shirts.
Oh, right.
Just pause there for a second.
I've got to give you in the
audience a great visual.
Before I started my first
company when I was 19 years
old, I worked at a law firm.
And I mean, that sounds
so prestigious, right?
It was not okay.
And I'm going to make
it so much worse.
Right before I started,
uh, blue diesel, my first
company, I needed a temp
job in my only skill.
Like I went to a temp
agency to get a temp job.
I'm like 19 years old.
Yeah, my only marketable skill.
I drove here.
I can type.
Oh no, even better.
Yeah, that's right.
No, the story gets better.
I did not drive there
because I didn't own a car.
So get this.
This is, I mean, this is
such a low that I can't
wait to share with you.
I'm looking for a temp job.
I have every bit of
maybe 20 in my bank.
And so the lady calls me up
and she says, Hey, good news.
We found a job for you.
You're going to love this.
At Nationwide Insurance.
Yeah.
It's so funny that
you just said that.
Of course, of course.
That's actually what it was?
I just went with the odds.
Largest employer
in Columbus, Ohio.
So just like, I just
went with numbers.
There's two stages.
I'll whip through this, but
it's just a funny story.
So, they're like, yeah, but
you have to have a suit.
We assume you have a suit.
And I'm like, that's
a big assumption.
I do not.
Right?
That's where I got
my special suit.
Where I um, I went to Goodwill.
And like, I only had 20
to my name, so like, this
was a big investment,
right?
But wait, Will, how were
you gonna make sure that you
could balance that budget
against needing this suit and
obviously a Hawaiian shirt for
Hawaiian shirt Fridays, right?
Like, no way
you'd just spend all
that on the suit, right?
I buy a suit from Goodwill.
For $8.
It's a three piece tweed
suit from the seventies.
That is wildly ill-fitting also.
Oh, what 19-year-old is
wearing a three piece suit?
, like total
vest?
None.
None.
Okay.
But this, this is, this is the
visual I wanted to give you.
I also didn't own a car, so
the only way I could get from
my, my campus apartment all
the way down to nationwide.
Ryan, do you remember the meme?
I'm late for business?
Business guy on
rollerblades.
Uh, yes.
Oh my god.
You were business
guy on rollerblades.
Brother.
That's amazing.
And the only thing that
was better was I had a fake
briefcase that I had to carry
with me on rollerblades!
I mean, it is the meme, right?
So I was actually Did you
buy the briefcase that day
too?
Dude, picture this.
I can't remember briefcase.
Even a briefcase was just like
a facade of a briefcase.
That's what I'm saying.
It was like a pizza
box with a handle
on it,
painted black.
Picture me in the Dead of
August, it's like a hundred
degrees outside, in a wool
three piece suit that's tweed,
rollerblading with a briefcase.
TAP!
TAP!
TAP!
No.
Yeah.
Oh
god.
No, so That might have
been the best thing that
happened in Columbus in 1993.
Let me tell you, it
was And probably doing
tricks on my way down.
So Of course!
Let me, let me chase the
temp job didn't work out.
.
Oh, so I, I just finished
this, this story, although
that was the story.
Um, I show up, it is an
office of just me in a hundred
very angry women, and they
saw me as like fresh meat.
To like, lay everything,
like all their issues on.
Sure.
So I show up, they're like,
You're the new typist.
Cause whoever went on
maternity, I'm like, I guess.
It was almost like
out of a movie.
They handed me like a ten
foot tall stack of papers.
And they're like, type
this by four o'clock.
You're waiting for John Candy to
walk in with the coffee, right?
Like, what is happening?
It was
so bad.
It was, I mean, I typed
the hell out of it.
And, and those ladies loved me.
But, let me tell ya.
Also, this is totally
inappropriate.
I've never gotten so many
back rubs in my life.
I, I was like, I, I know
like totally out of bounds,
but I was like, these
ladies are like really nice.
Treated so well there.
So when I think about
the, what if, and I think
about alternate universe,
that actually happened.
I actually lived my alternate
universe and it wasn't
okay.
Look for everybody listening
to the podcast right now, if
you want to start fan fiction
around this, I say we create
a graphic novel of will who
never escaped the typing pool.
Maybe let's do it.
Ryan at startups.
com email me, let's get
chat GPT writing this
thing for us tomorrow.
You know, when I look back at
that alternate universe, and
that was basically what I was
doing before I started my first
internet company, I look back in
that and I say, holy cow, like.
Had I just kept down that path,
and that was the only way I
could eat at the time, right?
Like, it wasn't, like, I
had a lot of career options.
And had I stayed down that
path, like you said, not hard
to think about where that goes.
Like, that's got a pretty
specific trajectory,
and I was on it.
You'd be giving back ribs.
Probably.
And so, anyway, When we think
about that, okay, when we
think about, shit, you know,
what are all the what ifs?
My what if moment at that
point was, you know, I, I
changed course and started
an internet company.
I dropped out of school, right?
Like, that was a hard 180.
From where I was at the time.
Now, had, had I not done that,
I could've made up a what if.
Man, if I just started that
internet company like I thought
I could've, I could've started
a company and it would've grown
to be whatever, and it would've
been like, this huge outcome.
Which kind of brings
me to my other point.
Which is, when we think and
look back on the what ifs, the
things we could've, should've
done, we love to romanticize
what that was gonna be.
The upside of what that is.
You know what I mean?
And it's so funny too, because,
you I think that because so
much of it is in our hands
in the founder space, right?
Or we believe that it is, right?
So we, we, we fantasize
and we romanticize
those, those outcomes.
But in the same way that we
do that with like within the
stripes, like what if I had,
if I hadn't sold, if I had
sold, or if I had, you know,
I hadn't taken on that co
founder, if I had, you know,
whatever, but we don't do this
in the, in the other realm.
Right.
So we were like, okay, so
if you'd stayed in that
typing pool, somehow we're
not going to romanticize
that in the same way.
It's not like, and then.
Will was CEO and chairman of
nationwide insurance, because
that's the same Delta that
we typically romanticize.
We're like, we go all the way.
We were like, this thing would
have been the next Facebook,
but weren't you running
like a local digital agency?
Like, forget about that.
It was going to be Facebook.
Right.
So it is, it is so funny, man.
Like how, how skewed
that gets and like.
We can't even call it
rose colored glasses.
It's like a rose colored
space mounted telescope.
Right.
It's yeah.
Yeah.
Yeah.
But, but I think what's
fascinating about that is we've
got this ability to take the
what if and apply an outcome
that we can't possibly forecast.
I'll give you the most
popular ones, right?
The most popular one
without question is what
if I had raised capital?
What if I had raised capital?
If I just raised capital,
you know, or if I just do
raise capital, then all of
these great things would
have happened with capital.
And I'm thinking to myself,
no they wouldn't have, right?
Like, do you understand
how that actually works?
That doesn't mean
everything's a failure.
Obviously, there's
great capital stories.
That doesn't mean yours
was going to be a great
capital story, right?
Like, that's the
part I don't get.
It wasn't just based on math.
It wasn't going to be
right without knowing
anything else about it.
Wasn't going to be
if I just started the
opportunity, you know, it would
have been could have become X.
And I always think about that
in terms of Facebook, kind
of maybe the most popular.
I could have done that of
all time with the answer
being categorically.
No, you couldn't.
Yeah.
So At the time, this is
a great example being the
Winklevoss brothers, right?
You know, like, this
story's been fictionalized
so many times, who knows
what's true anymore.
But their idea that, like,
had evil Mark Zuckerberg not
stolen the idea, which is
the bullshit of all time,
we would have had Facebook.
No, you wouldn't have.
Yeah, no, Cameron Tyree,
you wouldn't have.
And they're super smart
guys, so I'm not taking
anything away from them.
That
was Mark's journey.
It'd be like you and I saying,
if that Ryan day hadn't taken
that head coaching job, you
and I could have, you know, co
head coached the Buckeyes to a
national championship this year.
That would have been amazing.
Probably not.
Definitely
not.
Right?
So capital being,
being one, right?
The idea being the other.
If I just started this
idea, et cetera, I look
at it the opposite way.
I actually, I'm so jaded by
this bullshit of romanticizing
the what if that I'm
almost more shocked that
the people who did do it.
Did do it.
I'll give you an example.
You were hanging out with us
at like around that same time.
Do you remember when a friend of
ours that used to do marketing
here, Derek Ray was here.
Yes.
Yeah.
Yeah.
And so Derek and I, good
friends, are good friends
with, uh, Sean Rad,
the founder of Tinder.
A long time ago, Sean used
to work for Derek, uh,
like in a previous job.
And then Sean kind of came on
as the, the, the CEO and then
Derek kind of worked for Sean.
And then, uh, my wife, Sarah
was Sean's first employee.
Right?
You know, so I introduced
Sean to Sarah and had the most
hilarious interview of all time.
Around that time, Derek and I
are talking, he's single at the
time, and we're talking about
this new app that everybody's
talking about called Tinder.
And Derek's like, it works
amazingly well, right?
Like this thing is crushing it.
And I remember Sarah
was like, you know, Sean
started that, right?
And he's like, his
just face goes white.
He's like, gotta be
kidding me, right?
Now, this was one of those
cases where like, even Sean
couldn't have believed, right?
That Tinder would become Tinder.
It was gonna do what it did.
He was almost living his
own alternate reality.
Like, I think I told you
about this, but like, years
later, uh, Sean and his
girlfriend at the time came
over for dinner with Sarah
and I. We were just catching
up on how things had gone.
You know, I think I told you
about his sale, or not sale,
the handshake deal that wasn't,
you know, the most, the biggest
misunderstanding in business
history between him and IAC.
Even Sean!
You know, like anybody
else was kind of surprised
it went that way.
Like, you know, even
the guy that started it.
And when I say that a million
people could be like, Oh,
I could have done Tinder.
Look, dude, even the guy who did
it was surprised he did Tinder.
Hey, you could have done it
where he actually did do it.
Don't believe it, right?
It's one more version of
armchair quarterbacking.
And it's yeah, just as
unbelievable and ludicrous.
Well, I also think that there's
there's a part of it like
when we're thinking about that
upside It always cracks me up
that that same upside never
seems to have any consequences
attached to it, right?
In other words, like, oh
I could have started it.
Oh cool You know what you could
have also done in the process?
Lost your spouse through
divorce, alienated all your
friends, had a heart attack,
lost all your money Like we only
talk about the the best cases of
it But that's what I'm saying.
Like when I think,
uh, perfect example.
So after my rollerblading slash
typing career, right, I transfer
into this internet thing.
And now when I tell the
story, I actually just told
it on Reddit this morning.
Right.
And it was like, it was
like people were going
crazy on Reddit over it.
Surprisingly.
Positively, which I've
never seen happen.
When I was telling this story,
It's a cool story now, like,
Guy risks, it's a fundamental
founder story, right?
Risks everything, starts
with nothing, becomes
something, blah blah blah.
And I'm like, okay, yeah.
The story played out, the
what if played out, But do
you know how much it cost me?
To tell that story like how
much emotional strife I went
through how much I lost in
the way Like do you know
the part where I didn't see
my family for four years or
celebrate Christmas ruining
the fantasy?
Yeah Yeah, exactly.
Exactly.
That's what I'm a point when
when we create the fantasy It's
so convenient the
reason that's a problem.
It's like when I when I
look back in time And I
decide to buy stocks after
I can see what they've done.
My portfolio is amazing
every time I buy the dips.
When I trade on a reverse
time heuristic, it's
perfect every time.
It's amazing how
good I am at it.
It's amazing.
And it also
forgets to calculate
a few things.
And by the way, like as
we're going through this
stuff, like, you know, as
you're listening, whatever,
it's important to start to
build this mental model.
So you could model
against what if.
Because what if is a dangerous
place to go if you don't
understand the realities of
what if what if it's so much
fun to say in that I became
a billionaire and blah blah
blah what if isn't as fun but
it's more practical when you
start to say well what would
that have cost me 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.
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.
I want to tell a story of
where I have a what if,
except I actually know
what it would cost me.
Okay.
As we're growing blue diesel.
We merge into another agency,
that agency grows bigger, um,
and we get to a point where
we're at like 700 million
in revenue, where we're
planning on going public.
This is like 2001, 2002,
if I get my dates straight,
it's a long time ago.
I hated it.
I hated working there, right?
Um, nothing wrong with the
people, nothing wrong with the
clients, I hated the services
business because we were an
agency, and I hated the work
that we did, which was services
for pharmaceutical companies.
I got no problem with
pharmaceutical companies
as much as they're all
hated in their own way.
Um, just boring, right?
Like, I just couldn't get up
in the morning and being like,
I want to sell more Prozac.
I will make the world
a happier place.
But, um, I just, I
couldn't get pumped.
While the whole company is
super pumped about going
IPO and becoming bigger.
I'm like, I need to get
the fuck out of here,
like, I have no interest
in any of this, and this is
sucking the life out of me.
So, so, uh, here's what I'm
gonna paint the, the what if,
the what if was, had I stayed
there, uh, we ended up selling
it to Dan Snyder, who owns
the Washington Commanders.
Um, and then my business
partner, Blaine, who's
one of the best operators
I've ever seen, stayed on.
And took it public.
Did what I would
have been my what if.
Ryan, here's where
that's interesting.
Blaine and I get together
on a periodic basis.
And we compare notes as to what
it took and what it earned.
To go that path.
To stay with it,
run it through IP.
Because he did it.
Like, he lived my
alternate life.
He made Gobs more money, as
you tend to when you take
companies public, right?
Tends to be one of the outcomes.
But holy shit, what it
cost him and what he went
through to get there, I would
never be willing to endure.
Now, I can't say whether Blaine
would, I mean, he did it, right?
So, you know, I'm
not speaking for him.
I'm saying, knowing what I know,
it would have ruined me, right?
Like, I just can't
see that happening.
Not a trade off you
would want to make.
Also, I was 27, hold on, just
one thought, I was 27 when I
made that call, I would have
eaten up from 27 to 37, that's
how long it would take to see
that through, I would have eaten
up maybe the best years of my
life from like a, like being
single and doing, you know,
fun stuff, to put into that,
and it wouldn't have bought
me a single thing, because I
didn't do any of that, and I
had, I got everything I wanted
anyway, right, so I can't
say I lost something, because
it was nothing I needed.
Yeah, I think it's, it's, it's
so hard, especially when you
look at a, at a situation like
that, where there is a kind of
a big and binary outcome, right?
I do this, I get
a bunch of money.
I didn't do that.
I didn't get that
bunch of money.
Right.
I enjoyed a bunch
of other stuff.
Those are the things that are
a lot harder for people to see.
But I think that one of the,
one of the challenges is
that when we're going back,
like when we're doing the
revisionist history, every risk
that we look at that pays off
looks glamorous in hindsight.
The reality is.
In the moment, most of them
are fucking terrifying.
Yep.
Right?
You're, you're about to,
if you can even see it.
Sometimes you don't see it.
In that case, you saw it.
You were like, stay, and we
push for IPO, go, and I can
just do my own thing, and
I can feel good about it.
Great.
In some cases, we don't
even necessarily know
that we're at that much
of an inflection point.
Sometimes we do,
sometimes we don't.
Maybe like, hey, let's take
on that, that seed round,
which doesn't seem like
a huge inflection point.
But it's going to then mean
that you're going to do your
series a and your series B
and your series C. And now
you're set on a path where
there's only one outcome.
And so they, they look great in
hindsight a lot of the times.
And again, like somebody said
at one point, but it's like
the difference between being
brave and stupid depends
on the outcome, right?
So when we're only looking
at the outcomes where we
know people, one, of course,
every one of those decisions,
every risk that was taken.
Is going to look really
glamorous, but the reality
is, in, in the moment,
they are anything but.
I gotta say, and maybe this is
a factor of age and experience,
when I see success, my very
first reaction is, is this.
At what cost?
Yeah, yeah, yeah, 100%.
Like, what, what was
given up to get that?
Yep, because, uh, at this point,
just because I've been around
long enough, I've met countless,
um, successful people.
But I also, because of the
position that we're in and
the relationship we have
with those folks, I get
to see what it costs them.
And I'll go back to, it
costs them marriages, it
costs them relationships
with their children, it
costs them sometimes their
sanity, their happiness,
their ability to be happy.
Uh, not in every case, right?
I'm not saying it's all bad.
I'm saying, you don't
get to those levels.
without insane amounts of cost.
You just don't.
And by the
way, that was when
it worked out.
Right.
So we're, we're now
talking about that was
the success, right?
Cause all those same things
can also be true when you fail.
All right.
So yeah, no, no guarantees here.
So we want to be
careful about that.
We're not saying that risk is
necessarily the path, right?
We're, we're exploring the,
what if we'd gone the other way?
It's
kind of wrapped
that part of Ryan.
What I'd say is even in
the upside, there's a
phenomenal amount of cost.
And we, we have the danger of.
Romanticizing our own
outcome, choosing our own
adventure, so to speak, and
it always goes well, right?
Like, it doesn't always go well,
and even when it does, there's
a tremendous amount of cost.
So there's a bit of a danger
in looking at the what if
as if, one, you were even
going to get there, and two,
it was going to end without
the cost you think it does.
I was going to say, there's
a fascinating other side
to this that I think we
should dig into, which is,
we also romanticize what the
downside would have been.
And I think we get
that wrong too.
You know what I mean?
A hundred percent.
Right.
And I think that like at the
beginning, the calculus looks
something like, okay, what risks
I take to avoid failure, right?
Like how do I avoid failure?
Which, yeah, you want to,
you want to manage the
downside to some degree.
Um, but it's, it's not
really what we're trying
to do there, right?
What we're trying to do is, is
means that like, that we can
trust that we'll survive it.
Right.
Because I think that once,
once we've been through
enough failure and his
startup founders, we're,
we're no, there's, there's
very few degrees between
us and, and separation
between us and failure,
we've all experienced it.
You realize that that is
what it comes down to, right?
It is, it is surviving it and
being around to keep going.
Right.
We talked about this in
the last podcast, right?
It's like that ability to
tolerate some level of risk
is really what you're saying
is, can I absorb this amount
of risk and keep moving?
Right.
And generally speaking, the
downside isn't what we think
it's going to be either.
I think that
also prevents us from
getting to the what if.
I'll give an example that you
and I have a shared experience.
So when we bought Zirtual.
com out of essentially what
was an overnight shutdown,
it was a complete shitshow.
We were on the tail end of
someone else's nightmare.
The worst thing could possibly
happen is your business
is growing like crazy, and
then some bizarre funding
event happens where the
floor falls out from under
you, and overnight you have
to shut the thing down.
That is kind of the worst
case scenario as far as like
didn't see that one coming.
And so, so we certainly feel
for the founder on that.
However, let's talk about how we
looked at the what if of that.
Okay.
Yeah.
So we bought that company
in an overnight sale, right?
Like, I mean, when we say
overnight, some of you have
heard the story on the podcast,
but we literally mean overnight.
Like it started at 10 p.
m.
It ended at 9 a. m. We all
of a sudden owned a company.
With 450 employees, uh,
that we had zero diligence
on on Monday morning.
Now, when I say a lot
of people that week,
but a lot of phone time,
but let's talk about what
actually happened or said
differently, how we process the
what if of that risk so that
folks can understand that if
you use a fairly reasonable.
Gauntlet, if you will, when
you put stuff through it, you
can get to a better outcome.
For example, Ryan, when we first
looked at the asset, again, this
was in a condensed period of
time, but even let's say just
the next day after we're like,
Oh shit, we, do you remember how
we were just downside modeling?
Yeah, that's all, that's all
we were looking at because
what we're trying to figure
out is like, okay, it's going
through a catastrophic failure,
but is this failure terminal?
right?
Like what is survivable of this?
Can the, can the employees
stick around or not?
Cause we didn't know
that at the time, right?
Because there were,
there were some labor law
issues, all kinds of stuff.
Can the employees
stick around or not?
If not, then what,
what do we do?
Can, can we staff up 450?
So what's, what's the
downside look like?
If none of those people
can stay, what do we do?
Are the clients going to stay?
How many of them
are going to stay?
If it goes to zero income,
Do we still want this?
What's the likelihood
of that happening?
Right?
So we were just looking
at, if you continue the
trajectory that this thing is
on, which was down into the
right, what happens, right?
And so if we play that out and
we downside model that, what
do we need to be prepared for?
And are we willing
to tolerate that?
Are we willing to adapt
around the likelihood that it
continues on that trajectory
for at least a while?
Let's
play that out.
Let's run a scenario.
Just cause I want folks to
be able to use this, uh, this
mechanism for themselves.
I think it's
incredibly valuable.
A lot of people look at
risk modeling like, let me
see what the threshold is
at which point I walk away.
And I get that, that's a
reasonable thing to do.
We look at it a bit differently,
which is, hey, what is
the, like, okay, yes, the
downside is significant,
and that would hurt.
But could we absorb it?
Not, do we not want it?
But in the worst, worst, if
the thing goes to zero, can we
friggin figure something out?
And the answer is usually yes.
Okay, that's way different than,
Hey, this might take a loss.
Of course it might take a loss.
Like literally anything
could take a loss, right?
We work took a loss.
It was the biggest funding
event in history at the time.
Um, so of course,
anything can take a loss.
What we're saying is, do we
have the confidence that if this
thing starts to nosedive and
we're pulling back on the stick
that maybe we can't pull it up
but we can at least crash land
it and figure it out from there?
Yeah, are we resilient
or are we not?
Right?
That's, that's kind of the
question in that moment.
Right, right.
And so we looked at it and
we said, okay, worst case
scenario, all the clients bail.
All of them, there's
thousands by the way.
All the clients bail.
Worst case scenario, all
the virtual assistants bail.
Not awesome either because
you kind of need them in
order to earn the money.
So we look at it and say,
well, what would we be
left with at that point?
We'd have the domain, we'd
have the site traffic, we'd
have the infrastructure
of how billing works.
So, we know how to hire people.
It's not like, even if they
all left, like, we couldn't
figure out how to hire humans.
Uh, it would be hard.
Not exactly how we planned
our day, but we could do it.
Could we get more clients?
Well, guess what?
Most of the clients that
would have just left have
nothing to do with the
clients that have just shown
up the website tomorrow.
So as far as they're
concerned, business as usual.
As concerned, business
as usual, right?
So for the most part, we knew
there would be some level of new
clients coming in the door, even
if we lost all the other ones.
So when we're modeling that
downside, we're modeling it
from the standpoint of not,
Oh, we don't want to take risk.
It's, hey, even if we
have to start shit from
scratch, we can do it.
Yeah.
Yeah, I think that's the thing.
I think you started to
use a kind of a crashing
airplane analogy before,
and it's a good one, right?
Because if the plane's crashing,
and everything's gone, the
crew's gone, the fuel's
gone, the engines are gone,
you're still going to try to
pull up on the stick, right?
Yep.
things you can do to minimize
that impact at that point.
And you're constantly
recalculating.
I think that's the, one of the
misnomers about how to handle
risk is that you can somehow
do all of that in the moment.
You really can't like there
is that moment you, then you
have to make some decisions.
You have to start moving forward
because risk is dynamic, right?
Because, and we knew that
in that situation, perhaps
one of the most dynamic risk
situations I've ever been in,
because it was at that point,
a. Rapidly depreciating asset
because the number of, of,
of staff that we're going to
stick around after day one,
day two, day three, day four of
paused operations is going to
go exponentially off a cliff.
Same thing with clients,
same thing with web traffic.
If they show up at a site
where they can't buy anything.
Right.
So all of that starts
to compound, but.
That's why you have to recognize
that it's a dynamic situation.
Do you willing to jump in
there and to your point,
say, what's the worst?
Can we absorb that?
Knowing that that's the
worst and knowing that we're
going to fight to make it not
happen in the first place.
I think folks see this the most
now with, with their startups.
They say, Oh, if we do X,
Y, and Z and the startup
fails full apocalypse.
Yeah, not exactly right.
Yes.
The startup goes away.
Yes, that actually
does happen, right?
But you don't go away, right?
Like it sucks.
You have to let people
go, which is awful.
I'm not, I'm not
saying anything's okay
about this at all.
Right.
It sucks, but then
you go do other shit.
So I'll give you
another example.
So years before that, you
know, I started a company
called afford it raised a
bunch of money from some
high profile investors
like Bessemer and founders
fund and all these folks.
And, uh, it imploded it.
I mean, we raised like
A million dollars.
It wasn't like a ton of money,
but it went away and it sucked.
I mean, it ripped my heart out.
Like, I love when people go
back and like, Oh, we only
raised a million dollars,
so it wasn't that bad.
It could have been
a billion dollars.
It did not matter.
Like I ran myself through the
floor for a very long time.
At the time, you look
at that, and you think
that's the only outcome.
Oh, if this fails, then
this I'm branded for life.
I'm this scarlet
letter of failure.
Do you know I look back on that,
and that was like 15 years ago?
I can barely
remember it happened.
I can barely
remember it happened.
It was like, it was
the bane of my life.
It was the end of my existence.
And it's a footnote
in how I remember
my life, right?
Now, some people might say
that's a trauma response, Will.
I'll take it!
Even
better!
I don't
have to
live
with it on a daily basis.
It's under the rug,
right where it belongs.
Super convenient.
No, but I'm saying like, It's
the same way like, you're a
junior in high school, and
someone doesn't ask you to
prom, and your whole life
is over, your whole life is
ruined, and then you go back
later in life, you can't even
remember who that person was.
What we suck at, as humans,
is modeling past the present.
We have this amazing
ability, and it's not
always good, to model the
future in the what ifs.
In the most fucked up
way Like, like never a
practical, never come true.
And I, I think as founders,
Ryan, that's dangerous.
It's dangerous to have
a broken forecasting
model in a lot of ways.
The way we're talking about
it is, well, I mean, I guess,
look, if all you're doing is,
is playing revisionist history
and you're using it, uh, as some
sort of cathartic process, or
maybe to ignite your midlife
crisis and you end up buying
the sports car, whatever.
Cool.
Yeah.
Right.
I think it becomes a problem
when you start to use
those past what ifs to make
decisions now that will have
impact off into the future.
You'll see this a lot.
I know there's, it's
a common problem with
inexperienced traders just
to use something that.
People really understand.
Well, you miss a couple of
trades and you're like, ah,
if only I'd gotten to that
one with them, if only I'd
gotten to that one at the
time, well, now I've got to
get into this one so that I,
well, this one isn't necessarily
going to do what those did.
Right.
But all of a sudden you're like,
put it all there because it's
going to do the same thing.
No, probably not.
Right.
And so I think that when we use
inaccurate heuristics, right.
Meaning that the revisionist
history and, and all of what
it could have been instead
of just what it was, right.
All right.
You can use what it was.
You can't use what it was
and what it never became
to dictate some future
outcomes for something else
that's entirely different.
That's where it starts to
get really, really dangerous.
And we see founders
do this a lot, a lot.
I agree.
And here's the, I want
people to get comfortable
with what if, right?
I want them to be able to live
with what if by doing so, I
want to make sure that, that
they don't romanticize what
it, what it could be, you
know, uh, improperly or build
an apocalyptic case of the
downside, which actually Is
never the way it's going to be.
It's like when people
talk about global warming.
And they're like, and then the
seas will rise and everything.
Like, as if no one's going
to do anything about it.
Like, people are just going
to sit in their homes and just
watch the water rise and be
like, Oh shit, I guess in a
couple years we'll all be dead.
I guess we'll all
eat boiled fish now.
I'm like, come on.
The world responds, that's
the whole thing, right?
And so, here's what I'd say.
When I think about how I would
love every founder to look at
whatever their milestone is,
whatever it's, you know, 50, a
hundred, whatever your like age
or life milestone is, I want you
to be not terrified of failure
of doing something wrong.
I want you to be
terrified of regret.
I want you to be terrified of
not challenging what if, not
looking at the hardest things
in their face and saying, fuck
it, I'm going to do it anyway.
When you look back and you
play back your highlight reel
of regret and failure, only
one of those, you'll look
back and say, man, I wish
I did things differently.
If you look back on regrets,
you'll always have regrets.
If you look back on failures,
but you always pushed,
you'll never have regrets.
And to me, that's a
sign of life well lived.
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.
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I hope to see you inside.