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.
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!
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.
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.
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.
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.
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