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, failure is one of those things that's omnipresent
in the founder space.
We talk about it a lot.
We talk about failing fast.
We talk about all this stuff around failure, and it's
funny if we think about it, this podcast is an
exercise in exactly that, like a founder's willingness
to fail and then to just.
Keep going anyways, because our first couple episodes
of this podcast, which we'll never see the light of day,
were abject failures, right?
They were failed, so pieces of content, but we kept going.
And so as you think about failure across your 30 plus year
career doing this stuff, how good have you gotten it failing?
I'm so good at failing.
I'm the heman master of the universe at failing.
And, and I'm proud to say that, and I don't say that to
be like controversial, right?
Like, oh, he's proud to fail, right?
Or like, I'm shielding this.
Like, you know, otherwise regret.
In fact, you know, we'll talk about that.
It's the actually the opposite.
Like I say that because you have to have a lot of balls
to fail and then fail again.
And then fail again and just keep on coming back.
But if you do.
Keep pretending that you're sure it's gonna work
the next time, rightly.
Absolutely, man.
Yep.
And actually let me modify that a bit.
I'm never sure it's gonna work.
No, that's, that's why I said pretend.
That's why I said pretend.
Yeah,
yeah, yeah,
yeah.
You're telling everybody else, you're like, okay team, we're
gonna do it this way this time.
And we're like, is it gonna work this time?
Like, yes, we, it's going to right.
You have to hope it will.
Yes.
Ly you have somewhat believe that it might.
Yeah, I agree.
Well, and the truth is you just don't know.
Right?
And I think that's what we're gonna talk about is what's
it like for a founder to get really, really good at failing?
I think I, I would argue it's maybe one of the
greatest superpowers you can possibly have.
Yep.
I wanna talk about where it comes from.
I wanna talk about like how we've developed it, how we use
it in our everyDay@startups.com and at some degree
in our lives as well.
And.
Why I think most founders, especially new founders,
are just looking at it the wrong way.
I actually, I'll go zoom out.
I think most people in life have have a misappropriated
version of failure.
They, they logically say, I have to avoid failure at the
expense of doing anything.
Right?
Yeah.
And I think that's the real problem, right?
When you spend your time trying to avoid.
Failure.
You're, you're missing out on a lot, but you're trying to
optimize for something that you can't possibly optimize for.
Right.
Which is success, which is like, if you knew what
to go and do, then Sure.
But we don't, most of the time, especially in our space,
to me, it's like hearing a founder say like, they,
they just, they wanna make sure that they're right.
Like that's not a lecture that we get.
Right.
Saying that you wanna be right, which is essentially saying.
I want to avoid failure it be tantamount to a boxer
saying, I'm just going to avoid all the punches.
Right.
Yeah.
Right, right.
Yeah.
Your job is not to never get hit.
Your job is to take the hit.
Right.
Keep your guard up and finish the damn round.
Right.
That's what you gotta do.
That's what being a founder is.
Yeah.
Let's set the tone.
We always say this, you're going into a market
that's never existed.
Yes.
With a product that's never existed, with a
team that's never existed.
Right.
Yeah.
And you also probably don't know shit.
Correct.
So.
Combine all of those things.
Where is the basis for certainty in this business?
It does not exist.
We're not in the success business, man.
We are in the error, rapid error correction business.
That's what we're in.
And I think like if we, if we pull somebody into our world,
we talk about this a lot.
Like we transplant someone from the real world, right?
Yeah.
Into our weird matrix world, right?
And they look at what we do for a living.
They're like, this makes no sense.
Because it doesn't, okay.
But they will logically say, they'll logically say.
I don't wanna do something like that because I don't
know the right decision.
Yeah.
I wanna go to my job.
In fact, I was talking to a buddy of mine.
This is actually just is so timely over this weekend.
I was talking to a buddy of mine that I've known him
since middle school, right.
Uhhuh.
So a very long time.
He started out in the startup world.
He was one of the guys that, uh, helped start price line, if
you remember Price line back in.
Yeah, yeah, yeah.
You know, wait,
you went to middle school with William Shatner?
Me and Billy.
And so he's clearly, you know, had that, that side.
Yep.
But he works for McKeson now.
He's a corporate attorney for McKesson.
He has the safest job in the world.
Yeah.
It's, and he was talking to me about how proud
he was of his safety.
He knows better.
Right?
He's like, I've been on the other side of things where
like I have no idea where my next meal's coming from.
And he's like, I'm in my fifties now, dude.
I'm not even trying to do that.
Right.
That is a very logical way
Sure.
Of looking at the world, right.
Our version of looking at the world is we run
the other direction.
Yeah.
Right, and, and I think when people start to do that, and
a lot of the folks that are listening to this podcast,
you know, for folks listening, if this is one of your first.
Time's listening to the podcast, we have two
segments of our audience.
One segment of our audience just decided they wanna build
a startup five seconds ago, and that might be you and the
other segment of our audience are very, very, very senior
and seasoned, and they just listen to these episodes,
just nodding their head the entire time, and it's a bit
of a trip down memory lane.
Yeah,
so I, I think, Ryan, let's speak to both of
those folks for a second.
Sure.
For the folks that are the grizzled veterans,
you know exactly what we're talking about.
There's no way you could have become a grizzled veteran on
the, I only get a right move.
Right.
That doesn't happen on a whiteboard.
It does not.
And for the folks just getting into this, I think
this is an important episode for you because I think
it's important for you to understand how important.
Learning failure is okay.
Yeah.
And so, Ryan, when you think about like, the
problem of avoiding failure as a concept, right?
For, again, these younger folks, how would you
describe that problem?
What, what is the problem when you start avoiding failure?
You're steering a parked car, right?
Like nothing's gonna happen.
I will spit my drink out.
Sorry about that.
I've never heard that term.
I didn't intentionally time that, I promise.
Yeah, that was well done.
So, but that's what it is, right?
Like you're just sitting around, nothing's gonna happen.
Right.
I hate seeing and I watch it happen a lot, right in
my getting customer session on Mondays and Fridays, it's
a constant refrain because nothing stalls a startup
like founders who need like perfect information before
they make the decision, right?
They want to know before I decide that this will
be the right decision.
It's not how it works, right?
I've realized lately that so much of my feedback
that I'm giving people has this undercurrent of,
and you're probably gonna fail, and that's okay.
And that's okay.
Right, right.
And like things like people trying, like belaboring
the point of we just, we figured out like these five
ICPs, we don't know which one to go after first.
I'm like, put 'em in a hat.
Draw one doesn't matter.
Right?
Pick somewhere, rule 'em in, rule 'em out.
You gotta start somewhere.
The minute you're wrong about one means you can
move on to the next one.
Means you can move on to the next one, means you can
move on to the next one.
If you just sit around in your boardroom talking about
which one you think is maybe gonna be the best choice,
nothing's happening, right?
Nothing is happening.
It's amazing because again, we come from worlds where
you don't have that luxury.
Okay.
Yeah.
No barista at Starbucks can just start making all the drinks
and see which one works and just hand them to customers.
Correct.
And be like, oh, well, uh, didn't work.
Didn't work.
You'd be fired in a day.
People don't like scalded milk latte.
Got it.
You like, you just don't get that luxury.
Now in our world, it goes the polar opposite direction
of what people are used to and what their logical
comfort zone would be.
We look at a problem and we say, okay, there's 10 different
ways we can go with this.
We actually don't know which one is the right answer.
Yep, we're smart.
We can kind of say, yeah, this is probably more likely
to be right than the others.
So
we often don't know and, and we're talking about.
Everything.
Just so like, it's not amorphous in what we're saying.
We're talking about hiring decisions, co-founder decisions,
investor decisions, product decisions, marketing decisions,
HR decisions, like you name it, there is a tremendous
amount of uncertainty.
And if in every case you're like, well, we can't get
it wrong, you will lose.
You will lose, and you'll, you'll lose too.
You and I because we are willing to make bad decisions.
Exactly.
And we know how to come back from 'em, which is interesting.
Yeah.
I think that's, that's an important part of it.
To me, again, it's so painful to watch because indecision
in a startup earns interest and it compounds daily.
Like the longer you go without making those decisions,
that the worse it gets.
And I think that one of the things that,
that I've always found.
Is for me, like the thing that can make me more comfortable.
If I'm really looking at a decision, I'm like, I
really just don't know.
Ask yourself what the consequences are gonna be.
We've talked about this a lot on the podcast.
It's like sometimes that monster you think that you're gonna
face just ends up not being that big of a deal, and most
decisions aren't irrevocable.
Right.
It's like we're not asking you to put a
tattoo on your forehead.
Right.
And even that is replicable, right?
You can, you can change that.
So I think that one of the things that you can become a
little bit more comfortable in terms of failure is knowing
that you don't have to continue a long way down this path.
And so for me, it's breaking that down and
saying, okay, I don't know.
But here's how I can go find out in the shortest
period of time with the least amount of resource
and all that stuff, right?
And then it's just iteration is the, is the tuition
we pay for learning, man.
This is how we get to understand what is actually gonna work.
We, we pay in small failures so that we can earn really,
really useful truths.
And if we don't do that, we're dead, man.
We're just dead in the water.
You said something interesting.
You said, you know, this concept of slaying the monster.
Yeah.
I think early on, if you haven't been put in that position where
you've been required to fail on a regular basis, or more
specifically, like most of the world does not come up in a
society that rewards failure.
Correct.
There's no version where the teacher gave you the
test that you got an F on.
Trust me, I tried and was like, congrats.
You've nailed failure,
right?
Yeah.
You, you now know how to not algebra.
Awesome.
Yeah, exactly.
Exactly right.
Like there's, there's no version of that barista making
all the, the coffees wrong in being like, you know what?
You've learned so much today.
Let's, you know, let's, let's promote you.
Right?
That's right.
You a manager.
There's no version of our lives.
And even in, and I would, I take this further
in our relationships.
When people are dating or trying to find their, their
mate or your parent of their children, whatever.
Yep.
Now, those are big decisions, don't get me wrong
a
hundred percent, but they're so, so fearful of
making the wrong decision.
Yep.
They never make the right decision.
And again, I think this permeates all
aspects of our lives.
I say this as a prelude.
I think that as humans, we are conditioned to not fail to
fear failure in that monster that comes with failure.
It's fascinating when you start to conquer that monster.
Right the first time, you know, you get knocked
down and you get back up.
You're like, wait a minute, I can get back up.
And it's this really fascinating mentality.
You know, people call it resilience, eh,
that's part of it.
Right?
Resilience.
You could be really resilient in an environment where you didn't
necessarily always fail or that everything was on the line.
Not a lot of consequence.
I think about my kids being resilient and they're not.
But I think about they would be resilient and I think like,
well, they're in a consequence re environment, like no
matter what failure they had.
They'll always be taken care of.
Yeah.
Yep.
There's a safety net there.
So it's, yeah, it's not real failure.
They haven't learned real, real failure yet.
But when you have all the consequence, like you tend
to have in a startup for the first time, you're
really looking failure, like you're looking down the
barrel of that gun being.
Holy crap.
Like if I get this wrong, the consequences is all over me.
Right.
And I think that prevents a lot of people from
starting from challenging failure or like from, you
know, like Dede defeating that beast, so to speak.
The monster that as you described it.
Yep.
Which I think is really AP prop.
Yeah.
So go back in time a little, I'm trying to do this right now.
Go back in time a little bit and, and.
See what you recall.
Like this is a muscle, but I think there's also, there does
seem to be a little bit of founder, DNA attached to this.
Mm-hmm.
But I've definitely seen people turn the corner on this too.
Like even if they weren't comfortable with it, I wasn't
to the point we were making before, like I've realized that
this is baked into my feedback.
I'm unintentionally doing it.
It's just such a part of how I think in startup mode.
Yeah.
That it just comes through.
And so clearly, like it's a well-developed
muscle at this point.
It's just muscle memory.
I'm just, it just, it just happens, but.
If you go back far enough in time, like do you
recall when this was?
When this was still like something you had to force
yourself into or It felt really uncomfortable because at this
point I don't even notice that there's a discomfort around it.
Yeah.
It was Jason Barker.
Remember the Jason Barker story where he used to beat
me up every single day.
It's really strange 'cause we had a kid,
did we talk about this?
Yeah.
There was like the tough kid in the school.
I wasn't there yet.
I was still outside of the school system at that point.
But the tough guy in the middle school was Jason Barker.
What, what is going on here?
I swear it was, it was just a pseudonym, right?
And so
badass name.
So Jason Parker used to beat me up every single day.
I was probably first or second grade, right?
Yeah.
I was like very young.
And every single day I would come home crying mind, like,
this is like back in the eighties where like parenting
worked a lot differently.
Yeah.
And, and I would come home crying and my dad would
be like, you know what, you're a wimp, right?
Like, come back to me like when you won a fight.
Like that, kind of like tough love.
Right?
And so obviously I was, there's no helicopter parenting that
hadn't been invented yet.
So every day, like it was his job, Jason Barker would just.
Beat my ass.
Right.
Every frigging day for a very long time.
I'm, I'm guessing it was at least a year, and every day
I would go home and every day I'd be like, well, I
can't beat him, so I'm just gonna take the L. Right.
Yeah.
Every single time.
One day, not any specific day or for any specific reason.
I remember I was getting my daily ass beating, like
adrenaline pumped through my little body for the first time.
And I remember flipping Jason over and just
getting on top of him.
Just wailing him, right?
Yeah.
And I was like, oh.
Lemme try that again.
Right?
And, and I say that because I remember like
the level of adversity.
I mean, when you're that young, it's like your
whole world is right.
Your whole world is being pummeled.
And I remember the visceral reaction Yeah.
Of finally getting on top of my failure.
I mean, quite literally in this case.
And, and beating that monster.
And I remember I got plain as day man.
I remember that feeling.
Like, if I can do this
Yeah.
Then what else can I do?
Yeah.
Right.
And at the time it meant up beating up other
kids in the playground.
But, but I remember it, it's still the sense of,
it was the first time that I felt like, man.
Like all that failure, which was really me learning to defend
myself turned into a strength.
And it did.
It did.
And I've never lost a fight again.
That's good.
I, I don't imagine that happens very much anymore.
I mean,
thank God.
No.
'cause I, you talked to Jason.
I did not get very big that not offended Well, for me, but,
but I guess what I'm saying is when I think about that,
again, you know, when, when you're asking the question,
the first thing that jumps in my mind, that was exactly,
you know, what that personal kinda like failure felt like.
Yeah.
And again, overcoming that failure.
Now kind of a weird and a very eighties way to do it.
Still,
yeah,
it taught me like it was getting beat all those times
that taught me how to win, and once I did and I had conquered
that failure, it was like a superpower in something
that I would reach back into, not the fighting part.
Time and time.
In time.
Again, there's a confidence that comes with beating failure.
There is, and I think it's very interesting because in,
in that case, you were sort of forced into that failure, right?
You didn't choose, you weren't like, I think I'm
gonna go try this fight every day of the week.
That fight came to you was not, but here's what's cool about it.
Here's what's interesting.
I've seen this with a lot of founders, myself included.
At some point you turn the corner on that and all
of a sudden you go like, you can be proactive.
You can choose to go and do something.
Yep.
That you will probably fail at.
Right.
But without that fear, without the hesitation.
Right.
That's, I think that's the really amazing thing that
starts to happen, and I've heard you say this before, but it's
that failure breeds success.
It does.
And let me build on that.
So as I'm going through those, you know, formative
parts of childhood,
yeah.
I had a tremendous amount of failures and hardships.
Sure.
But because I was able to kind of fight through and overcome
them, and a lot of times when people kinda like talk through
that journey, when you hear like overcome, you think of like
rocky at the top of the stairs.
Right.
Do an eye of the tiger.
Overcome is sometimes far less glorious.
Yeah.
Most
overcome is sometimes fro across the beach.
Right.
You know, to get the other side right.
It's not as glorious as it sounds, but when you've
put yourself in a position where you are in a position.
Where you've gotten through that, you actually do
know what the downside is.
Yeah.
You actually do know what that monster actually is
versus what you put it together in your mind.
And I think when that's the case, you're like, man,
I've started with nothing.
I've started with less than nothing.
Yeah.
So I know exactly what it means to go back to that.
And I don't want to,
don't
want to.
I can't.
Yep.
How did it work for you?
When, when, when you look back, uh, please don't tell me that
Jason Barker also beat you up.
No.
When you look back, when you think about, uh, where you were
in life and, and like where the first time you had a failure
meaningful enough that at the time you didn't think you'd
come back, but you did, and all of a sudden it clicked,
you know, something that's really.
Funny about everything we talk about here is
that none of it is new.
Everything you're dealing with right now has been done
a thousand times before you,
which means the answer already exists.
You may just not know it, but that's okay.
That's kind of what we're here to do.
We talk about this stuff on the show, but we actually
solve these problems all dayLong@groups.startups.com.
So if any of this sounds familiar, stop guessing
about what to do.
Let us just give you the answers to the test and be done with it.
It's funny, I'm gonna go back to probably very similar age.
I would've been 10, and this was a, this was a
very personal failure.
I failed to do some of the things I was supposed to.
I failed, was trying to.
Expand my little growing cattle business at the time.
Right.
And I loved your
farm stories, by the way.
They're great stories.
They're super, like for me, I mean, of course it's super
visceral, but like, I think it's something that just like,
they just feel easy to me.
They just feel easy to understand.
Right.
There's just something so basic about what happens there.
And this is one of those like life and death stories, right?
So I had tried to expand and I, I wanted to grow the, the
operation a bit bigger because I started making fairly.
Good money at that point, right?
Yeah.
At 11 or 12.
And like the, the cash had gotten real to the point
where I had to file a C corp the, the year after because
I needed a tax shelter.
Wow.
So, which is great, right?
That's fun.
But what happens is I start to try to expand this thing, right?
And it came with all kinds of challenges, right?
I got myself cash strapped in the beginning 'cause I,
I overbought and then there was a, a longer winter.
All these things happen, right?
So everything's going.
I love that
you're leveraged on inventory at 11.
Right, like
classic founder story.
I did, I leveraged myself, and then we had a longer
winter than usual, so I had to feed longer than
expected and it, it got ugly.
I was literally shoveling driveways and plowing people's
driveways to make cash to pay for feed for cows, right?
That's where I was at, so I had to have a side
hustle for my side hustle.
What ends up happening is that because I, I was.
Over my toes and all these things.
I wasn't paying as much attention.
I probably wasn't caring for things as much as I should.
One of them got sick and then spread some sickness, the others
and two of them ended up dying.
Right?
And that was one of those moments where like, I failed
and I failed hard, and it felt really bad, right?
These things weren't.
Pets, but they all still had names.
At that point.
You're 12, right?
Like you don't, you don't know how to completely
disassociate from that.
And so that was one of those things where then I was like,
I really questioned whether I ever wanted to do that again.
Right?
Because I'd put myself through all this hardship.
Everything just felt like it sucked.
Then, you know?
The spring eventually came and things got a little bit
easier and I, I made peace with the mistake I had made
and I told myself I would never compromise like that again.
I would make sure that I planned all that stuff, but
it was one of those learnings.
Right.
I understood now about like cashflow management.
I understand now about inventory management.
I understand now about Yeah.
Right.
Planning for contingencies and business stuff, right?
Yeah.
So lots of little, little lessons came there from
that failure and it sucked, but like I never would've.
Come to that same conclusion just by sitting
around and like planning.
Right.
You, you can't ab test a thought experiment, right?
It doesn't work.
Right.
The, the deltas that we create and start a plan don't
come from brainstorms, man.
They, they come from bruises in most cases in your case,
quite, quite literally.
Uh, in my case, it was an emotional bruise in your case.
Uh, it was one straight in the eye.
But yeah.
And it's funny 'cause they so many of these lessons
and I think when we talk to lots and lots of founders,
a lot of these lessons.
Came at early ages, and a lot of them weren't necessarily,
mine happened to actually be related to a business I
was running at a very young age, but a lot of times they
were just, it was just some other version of getting
comfortable with some version of ass whooping and failure
and overcoming it and then saying, Hmm, if I can do that.
I can probably just do whatever else I want to.
Let me just keep trying.
I agree.
I also, Ryan, I don't wanna overlook the fact
that you have to do this.
Yes.
Like it, this isn't like a luxury, like you can't
run a startup and just always get it right.
You can't even run a startup and get it half right.
Correct.
And I love when people look at successes of companies, you
know, successful founders, and they're like, oh, they must have
made all the right decisions.
Show me any successful founder and I will show you
a trail of tears a mile wide.
Right of all of the things that that went wrong in
order for them to get there.
And you get this later on in a cute documentary or
how I built this podcast or something like that.
And you get the real story when you actually meet that
founder over a couple drinks
Uhhuh
and you get the unfiltered, you know, not safe for work,
not safe for television story.
Yeah.
And it is way more graphic and it is way more awful and
you see it very personally.
I think that for the founders that are out there that, that
are in our category of kind of doing this for the first time.
When they hear something like embrace failure,
it sounds like a trope.
Yeah.
Yeah,
right.
It
does.
Yeah.
But I don't wanna do that.
Uh uh Like I just wanna do all the successful stuff.
Right.
And like you don't have a choice.
Yeah.
Like the reason we're saying embrace isn't 'cause we love
getting punched in the face.
It's because getting punched in the face is the job.
Yeah.
Right.
That's literally what we do for a living.
And if you can't learn to get good at it, I think your
boxing analogy was phenomenal.
If you can't.
Like take the hits, you won't win any fights.
It's that simple.
That's right.
Now if, if we get out of, you know, metaphors and analogies
and things like that, if we get into really specific
things, if you're gonna do marketing as an example, yeah.
There are 20 different things that you need to do.
Yeah.
Only one of them is correct.
There's no goddamn way You are gonna know which
one of those is correct.
When I used to run an ad agency, one of the things I
used to say to my clients is, you pay me to be less wrong.
Right.
I never said, you pay me to be right.
Right.
Like, you know, if you gimme money, we're
always gonna be right.
You pay me because I know how to be less wrong than
you would be on your own.
But both of us are gonna be wrong.
Yeah.
You'll just pay to be, to be hopefully less
wrong.
I'm gonna be wrong for less time than you would've been.
Exactly.
I mean, every breakout we've ever had started as some version
of like an embarrassing version one that we shipped anyways.
Right?
Yep.
That's the key.
We shipped it anyways.
You just going back to the whole, you know, trying to
steer the, the parked car until we're in motion, nothing
is actually gonna happen.
Right.
I have bet To ship a page that converts it 0.3% rightly, and
then, then two weeks later it needs to be converting at three.
Right.
I'm never gonna figure that out.
Just by sitting there and extrapolating or simulating
or guessing, right.
You just have to put rubber to road before
anything's gonna happen.
It's the same response I give people when they're talking
about bringing on a co-founder.
You know?
Yeah.
The, the most tired one now is I'm trying to bring on the
technical co-founder, and I'm gonna say, I'm, I'm worried
about hiring the wrong person.
And I was like, you probably are hiring the wrong person.
Yeah.
And that is part of the process, which is why I always talk about
vesting and cliffs and how to unwind this thing in the divorce
papers before you get married.
Yep.
Because.
Like, there's no way you could possibly know this
is the right co-founder.
You can run all the checks and be totally wrong.
In the same way, if investors really knew how
to make good investments, why do they make bad ones?
Yeah.
If they're so good at making good investments, why do
they ever make a bad one?
Yep.
Right.
And why is it the, the portfolio strategy suggests
that you need to make 20 investments to maybe have two
uhhuh,
why don't you just make 20 good investments if
you're so good at this?
Right.
It's not the way this works,
not how it works,
not the way this works.
And because of that, we're not in the business where we get
to say, oh, I'll just, I'll just hire the right people.
I'll find the right co-founder, I'll get the
right investors, et cetera.
So I think that brings us to the next thing.
Which is okay, we get it.
You've pounded us over the head that like you can't
make the right decisions.
So then what?
So I just go around making a bunch of bad decisions.
Doesn't that like totally lead to failure?
It does sort of, and what I would say is building this
skill of failure is maybe one of the greatest skills I know
personally that I've ever built.
And I said that, you know, at the top of the,
the show is like, I'm really good at failing.
And what I really mean by that is I'm really good at
recovering from failure.
Yeah.
Yep.
Very few people have both the ability and more specifically
the confidence to go into something saying, yeah, I'm
gonna take a bunch of hits.
Doesn't matter.
It does not matter.
I gotta say, and, and I referenced this, you know,
because, uh, we write, we write like a newsletter paper about
this before, you know, we do these episodes and I said, it's
the, uh, the closest thing to a, uh, a potion of vulnerability.
Which brings me back to my Dungeons and Dragons years.
Uhhuh
and being able to be good at failure means not that I have
like this displaced confidence that's is like, I just somehow
for, for no reason believe that I like will always be right.
Right.
That I already know I'm gonna be wrong.
That's the big difference.
Yep.
I already know I'm gonna be wrong.
So I focus on the fact that when I am, which is likely going to
happen, here's how I'll recover.
Yeah.
And I think that's the mastery of the skill.
That's how it's tooled.
And I think over time, you know, uh, it becomes a reflex, right?
Recovery becomes a reflex because again, it's anticipated,
it's expected, and then, you know, we just get used
to that bounce back, right?
Yep.
We, we know we're probably gonna be wrong.
We wanna find out.
How we were wrong, why we were wrong, which direction
we were wrong in, and then we adjust, right?
Like I think back to, just like to, to go
back to childhood again.
One of the, the, the comments that I would get over and
over again, one of the reasons I was a desirable
player on, on a soccer team wasn't because I was faster
than most of the other guys.
It wasn't because I was, uh, more skilled than the
guys I recovered faster than my competition.
Yeah.
One of the comments that we get all the time is like, my output
was nearly the same regardless of how well I was playing or
poorly, like didn't matter if I was having a bad day,
didn't mean I would continue to have a bad day, right?
Coaches would constantly comment on this like,
you know, you can make a mistake and you get right.
Your head gets right back in the game.
You can burn yourself out in the first half, but you'll get
back in in the second half.
You'll keep coming back in.
It's because maybe I was just too dumb not to.
I don't know.
There's a point at which we just go like, and I heard
you say it a minute ago.
This doesn't just mean I'm have misplaced confidence, right?
But we decide where to apply our effort and then we
recover as quickly as we can.
And we get back in, we see like, okay, that wasn't working.
Let me, let me, let me try this again.
And I think that's again, to, I think it has to become a muscle,
it has to become a reflex really, that we just recover.
Resilience is one of those things.
I've, I've heard that before.
You know, I'll take resilience over brilliance
and, and particularly like when the clock runs long.
I think that does matter.
Uh, but I, I think that to your point, that's what starts to
decide the difference between a, a founder who's really going
to lament and failure, and one that's just gonna be like,
this is part of the process.
Think about from this, uh, perspective, think of how
dangerous a competitor is that isn't worried about failing.
Yeah.
That's terrifying.
Yeah.
A competitor with lots to lose.
Look, it's for as smart as they are, they have
a weakness built in.
Yep.
But a competitor that's willing to lose and keep
coming back, that person is dangerous as hell.
Yeah.
That person is dangerous as hell.
It's funny, I had this conversation with somebody a few
weeks ago, was that that classic thing of one of my competitors,
uh, just got funded.
Now I'm scared of what's gonna happen with them.
I was like, well, maybe.
I was like, but you've been around for, for five years.
They've been around for two.
Yes.
They just got But they just got funded.
Yeah, probably.
'cause they needed it.
Right.
You've established a business, you have recurring revenue,
you're, you have a more stable position than they do now.
They have something to lose.
But so does this company.
Right?
They have a, they have a run rate.
I said actually, of the competitors in your space,
there's another one that I'd be more concerned about because
they're more like you, right?
Yeah.
They've been around, they've proven that they can recover.
They're not moving as fast as this funded company,
but that's one of those signals that like everybody
gets really worried about.
They get scared, oh, they're gonna come.
They're gonna, they're gonna take us out.
All that means is they've got a budget to fail against.
So, yeah, there's some truth to that.
And you know, we've done whole episodes on this.
It's like, at which point you think you've seen exactly how
the story's gonna play out.
It never plays out that way.
No.
Again, I'll go back to investors 20 investments, two successes.
Yeah.
If the people who put the money in all the companies
are always the ones that are successful, then why are
most of them unsuccessful?
And let's take that a step further 'cause I can, I never
wanna overlook this one.
Most investors.
Most investors, I'm talking venture capital investors.
Are unsuccessful.
Right.
Most investors are unsuccessful at what they do.
They suck at what they do.
Yeah.
Right.
Now, this isn't me like, you know, bone
to pick with investors.
Just math
numerically.
Exactly.
Yeah, exactly.
You can't fake it.
There is a quadrant that they all pay attention to,
and in the top quartile, the Sequoias, A 16 Zs of the world.
Right.
Are there year after year, all the time.
Right.
And then there's frigging everybody else.
Everyone else,
right.
Yeah.
In that bottom quartile of investors.
Are the worst investors.
Yeah.
Now I say that to say they're probably pretty smart people.
Yeah.
Like generally if you put them, you know, uh, compared
to other humans out there doing their job, they're
probably pretty smart people.
However, the nature of this business does
not breed certainty.
In look, these investors do diligence.
They try to do everything possible to hedge for success.
Yet they consistently fail over and over and over.
They even have the benefit of only picking the best players.
Right.
It's not like they get stuck with like a a 12th
round draft pick kind of
thing.
Yeah,
right.
You gotta take one of these two.
Like, I don't want either of those two.
Like the top 10% of companies that are out there raising
are the ones that are gonna get a check from anybody.
Yeah.
And then a percentage of those are like the top ones
that'll wind up getting a check from Sequoia, et cetera.
But Sequoia has a, a list of failures, a mile long.
Right.
And that's Sequoia, right?
They're by far the best at what they do.
There is a great VC that invested in us years ago,
uh, called Bessemer and you know, very storied fund,
one of the oldest funds.
And I invested in one of my companies.
And I remember when I went to pitch them initially,
they had this great thing and it was basically
their wall of mistakes.
And it was all of the companies they passed on
and it was on their website if I, if I recall too.
Right.
And I thought, how smart, like, how, like humbling.
Yeah.
Um, which you don't see a lot in the VC world.
Um, how humbling to say we make lots of mistakes.
Yeah.
But guess what?
The successes we make, the ones where we, you know, find
that, that success they make up for, for the other ones.
Isn't that kind of what we do though?
That's exactly it.
You have to measure the failures, right?
If you quit after your first failure, the measure's not gonna
land in in your favor, right?
But if you continue to fail small, and then eventually you
win big, it bears out, right?
And I think this is super important.
I'm, I'm always thinking in terms of like, how can we
create the smallest blast radius within failure, but at a really
high blast frequency, right?
Like, I want lots of little explosions and I
wanna limit the damage.
Why?
Because this is how we get there.
Right.
I do love to break these things up and I think this
is part of how you get more comfortable with it.
Right.
I'd rather push ten one percent risks than one 10% risk.
Right?
Right.
Like, how can we test really small and, and again, default
to reversible decisions?
My thinking has always been, if I can roll it
back, let's roll it out.
Like what are we waiting for at this point?
If, if we build on that though, we've also taken
this same skillset and holy shit, is it portable
to the rest of your life?
You know, as I've been building a house, a house, I should
not be able to build that.
I have no, like, prior capability to build,
but I designed the house, I architected
the house to an extent.
I gcd the house.
I was the master carpenter for the house.
I've never been a master carpenter for a house.
The master carpenter builds every single
thing in a house, right?
That's what I did.
And it's a good sized house.
So like when we're talking about the scale of it, like
if, if you're gonna pick up like your first starter
project, it ain't a cabin.
And so just the scale of, it's also kind of overwhelming.
And I say this to say, the reason I was willing to do
that in a trade that I've never been in, I mean, I did all of
this for the very first time.
The reason I was willing to do it is 'cause I knew I
was good at failing and I've made plenty of mistakes.
Yeah.
No lack of mistakes.
Right?
And some of those, those are fairly expensive,
but I'm kind of like, so.
I'll figure it out and go for it.
And all the people in that world, uh, the other
contractors and all the folks that are involved in
it are blown away by this.
Like they are blown away that someone's willing to just roll
the dice on all these things and figure it out later.
Like, but that's not what we do.
I'm like, that's what I do.
That's what I do.
I'm really good at it.
Right?
Yep.
And what I tell them, I'm not good at being successful.
I'm good at being, making failures and
then figuring it out.
These guys are not good at failing.
Right.
Like, they get one thing wrong and they're done for the day.
Yeah.
Like, well, don't know what to do here.
It's time to go in for the day.
I'm like, okay.
And the one other thing I, I wanna apply this to, because
I still think it, it, it's important, it's really led to
me having no regrets in life.
And when I say that.
There are situations in life that turned out regrettably.
Yeah.
But when I say no regrets, I mean there's never a time
where I should have said yes and didn't say yes.
Yeah,
right.
There's never a time when I can look back and say, ah, man,
coulda, woulda, should have.
I said yes to everything.
To everything and lived a wonderfully colorful
experiential life.
I see you doing it with your family all the time.
Yeah.
You guys just explore like it's nobody's business.
It's the coolest thing, and it comes from
this sense of why not?
Yeah, yeah.
Right.
Why not?
Yeah.
I have.
Endless tales that started off with why not?
And that's the tapestry of my life and I'm,
I'm very proud of it.
I think one of the other ways that I've become more
comfortable with this over time, but before I make
the decision, like before I dive into something, right?
Like whether that's adventuring around the world or building
business, whatever it is, right?
I do try to think through, I may not know what the outcome
of the decision's gonna be, but there are a few things
that I can control, right?
I can cap my losses in time.
I can cap my losses, losses in cash before I begin.
Right.
And I can set some kill switches and I can sort
of decide the stop rules.
Yeah.
Before emotion shows up.
Before anything could, could kind of take me off
of my game as it were.
Right.
And make me worse at failing.
Right.
So part of being good at failing is, is sort of having
a plan for how failure happens.
Right?
Right.
You see the same.
I do.
And, and it's funny 'cause I apply that whenever I'm
gambling, I don't gamble a ton.
Uhhuh.
I always go by the famous Alex Trebek quote, which
says, uh, winning doesn't bring me a lot of pleasure,
but I fucking hate to fail.
Yeah,
right.
I hate to lose.
Right.
I, I was like, I just picture Alex Trebek saying that it
cracks me up every time.
But like when my wife and I, uh, go to the casino
and we go to the tables, we play blackjack every time.
'cause we can play forever.
And, uh, we always be a small amount.
Like we, we never go high stakes or anything else like that.
Yeah.
And.
I always say the same thing as we're playing, wanting
to stop taking my chips, and my wife never wins.
She just takes all my chips.
The, the second is I said, let's bet small and win big.
Let's, let's make lots and lots of small bets.
And over time those compound and that's how we win.
And it, and it somehow works.
It somehow works.
Maybe we're just lucky.
But I'll say this, the reason it works for me.
And I think for founders in life is because if you're
willing, like you said, I love you said the kill switch.
If you're willing to make those small bets over and over and
over, you know your limits.
You know your, your kill switch is you become invincible.
Yes.
You become the person that's willing to go and go and go,
and no one can knock you down.
They can knock you back,
Mario, with the invincibility star.
Exactly man.
They can never knock you down.
And if you're willing and able to keep coming back over
and over and over again, no matter what happens, you are
as close to invincibility as you can possibly get
in the startup space.
When you show up as a founder with as Mr. And
Mrs. Invincibility, no one can stop you ever.
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
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