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August 8, 2024 40 mins

Maria sits down with Bill Perkins, the legendary energy trader, to talk about his approach to risk in business, poker, and life.

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Episode Transcript

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Speaker 1 (00:15):
Pushkin. Hey everyone, and welcome back to Risky Business, our
podcast about making better decisions. Today I am joined not
by my usual co host Nate Silver, but by an

(00:36):
incredible guest, Bill Perkins. Bill is someone who I met
through the world of poker, but he is actually so
much more than a poker player. He is a hedge
fund manager, energy trader, of venture capitalist, an author Diewood
Zero was amazing book that he wrote that came out
a few years ago, and now he is also the

(01:00):
co founder of Skyfi. He also produces movies. I mean,
I think there are lots of things that lots of
things that Bill had done, and I've probably forgotten a
few caps that he's born over the years. But Bill,
thank you so much for joining us on Risky Business.
It's such a pleasure to have you here.

Speaker 2 (01:18):
Yeah, it's great to be here. I love talking to you.

Speaker 1 (01:21):
Likewise likewise, you know, it was very funny. We had
already kind of thought that you'd make a really, really
good guest, and then Ivan Boski died and he was
obviously the man on whom the Gordon Gecko character in
Wall Street was based. And you've said before that Wall
Street had been kind of an early inspiration for you,

(01:42):
and I was like, you know what, we really should
get Bill on on the show. So Bill, we're going
to talk a lot about risk and about how you
think about risk and in general, how you've thought about it,
how your thinking has evolved over your life. But let's
start at the beginning. So let's go back to New
Jersey for a while and talk about growing up and

(02:05):
when you first became aware that you know, life is
a series of risky decisions.

Speaker 2 (02:09):
Wow, that's a really good question. It's like you're kind of.

Speaker 3 (02:15):
At a subconscious level or intuitive level, you're aware a
risk even as a kid, right, Like if you take
the morality out of it, Like there's a cookie.

Speaker 2 (02:22):
In a jar, you're not supposed to go eat it.

Speaker 3 (02:25):
You take the cookie and somehow no camera know nothing,
but your parents know you took the cookie. Obviously you're
not smart enough to deduce like it can only be you, right,
And there's chocolate smudges on your shirt, and so there's
some sort of punishment associated with that, and you realize, Okay,
if this is my reward, if I take this risk
and get caught, there's this punishment as you're being socialized

(02:46):
into what to do not to do right, and you know,
kids try it out and test it out, and so
you're making these intuitive risk reward decisions as a kid, right,
and the consequences associated with that are actually training you
in later life to be risk averse sometimes right, even
if it was socializing you from a bad behavior to

(03:07):
a good beaver, let's say, not bad behaver, but behavior
they want you to do versus the behavior you want
to do right, and you start realizing like, wow, this
risk it hurts, it feels bad.

Speaker 2 (03:19):
I'm punished, I can't go out.

Speaker 3 (03:21):
I think you know, we all get traded, like trained, like, oh,
fail bad, right.

Speaker 2 (03:28):
I think there's a lot of yeah, society.

Speaker 1 (03:30):
Society definitely says fail fail e cools bad, right.

Speaker 3 (03:33):
Not until you get sports like baseball where it's like,
oh it's okay, you bat in three hundred, you're a
superstar or something like that. But by and large, emotionally
you're getting trained fail bad right. The shame even in
you know, like do you ask this girl out she
says no. You know, you get ridiculed or whatever. And
there's so many situations in your life where your very

(03:54):
results oriented, not expected value oriented, not like, if I
did this one hundred times, am I better off in
life taking this action even though there's this pain associated
with these losses?

Speaker 2 (04:04):
Right?

Speaker 3 (04:05):
And so I was fortunate to have a dad, although
a very tough and hard dad, was very very willing
to take risks because of the er he grew up in,
like and very much like, we're already at the bottom, right,
We're already this has already thought of us. You're already

(04:25):
you know, not expected to succeed, et cetera. You know,
he grew up in an era when you know, racism
was the law. It wasn't just like a thing or
a feeling or these.

Speaker 2 (04:36):
Group of people was the law. And so he didn't
give a fuck.

Speaker 3 (04:41):
He was one of those don't give a shit, I'm
gonna do X, Y and Z people, which kind of
unshackles you from this kind of emotional risk, aversion right
in a lot of areas that I got from that,
which then allowed when I later when my brain developed
to like, go, oh, what is the expected value of
this action to actually.

Speaker 2 (05:02):
Have my emotions align up with that? Right?

Speaker 3 (05:06):
So, you know, I find a lot of people they'll
get the but they still can't stomach the losses right,
the variance.

Speaker 1 (05:13):
Right, Yeah, I mean I think that from a psychology
a standpoint, one of the things, and you know, my
PhD was in risky decision making and one of the
findings that I come back to over and over and
over that I find, even me, even though I know it,
the loss of version is just such an incredibly powerful thing.
And this, of course is some of Danny Conneman's seminal work.

(05:35):
You know, would you rather have a sure thing or
you know, be with this loss? There's just something emotionally
where even though I know what the right answer is, right,
and I know and I know what I'm supposed to decide,
there's a part of me that says, yeah, but you know,
sometimes I just want the share thing. And if that's
true even on the page, now, let's translate that to

(05:57):
real life and to our real life decisions. And I
do think that that's a really big handicap that our
brains have when it comes to assessing risk and choosing
things that actually matter for our life life outcomes.

Speaker 2 (06:10):
Yeah.

Speaker 3 (06:11):
I think it's also the scenario dependent. I think some
of these things are rational, right, Like it depends on
what loss you're trying to vert. If you're trying to
not lose this image and you're like the wile risk taker,
maybe you over index to taking bad risks, right, because
it's just loss of version. So let's identify with the
losses right first, and then it's like, wow, I don't
want to lose this reputation of being this big bad ass,

(06:33):
I don't care trader. And then you just do the
riskiest thing exactly, and so now you've done the wrong
thing by being too risky.

Speaker 1 (06:42):
Right, Yeah, I think you said several things here that
I would love to dive a little deeper into because
I think that they should alight on your career. But
also just a light on risk in general. So people
have different priorities, right when you're calculating expected value, when
you're calculating risk, when you're calculating loss, you're not doing

(07:02):
it in a vacuum.

Speaker 2 (07:04):
Right.

Speaker 1 (07:04):
My calculation is different from your calculation, especially when it
comes to our lives. So when you said, sometimes it's
actually quite rational to want to want to, you know,
avoid a loss, and other times it's not. Are you
thinking as a trader right at this point? Are you
thinking as a dad?

Speaker 2 (07:20):
Right?

Speaker 1 (07:21):
Which parts of your life are you talking about and
I'd actually love to hear more from you on this
because you've also taken some risks in the past that
you know, maybe the U of today wouldn't take.

Speaker 3 (07:35):
Yeah, there's definitely you know, I have a saying that
humans don't net present value well and don't future value well.
Like our brains aren't really wired for that. They're wired
for like immediate, what's going on? Now, let me survive,
let me eat, let me do what's going on?

Speaker 2 (07:49):
You know.

Speaker 3 (07:49):
The first thing about risk reward is getting the variables right.

Speaker 2 (07:53):
Right. If it's like this.

Speaker 3 (07:56):
Decision, like if I'm going to move to the city
and I get a new job but it pays more,
but if it doesn't work out, you know, I don't
know people whatever, It's like, there's a lot of variables
to figure out. Okay, am I getting how these variables
switch in the you know, like zero in one case, right,
And so you know, I think the first step is
have a methodology to think about these things and then
you know whether the variables then you know, flip it

(08:18):
out and that takes time. You know, that's not really
it doesn't match the guy's like, oh bear run, you
know what I mean? Cookie eat you know that type
of thing, right.

Speaker 1 (08:28):
Sure, I'd love to hear it kind of specifically in
your case. How that's like, how did you go from
cookie eat, bear run to being someone who actually thinks
about this in a very logical way.

Speaker 3 (08:40):
In trading, we're all trying to avoid the risk of ruin.
You know, Sometimes that there's decisions where I'm like, well,
this is the trade and this is what we do,
and we we you know, sometimes you get got is
kind of like the slang use like sometimes you just
get got. If you're an insurance company, the hurricane's going
to come, right, But you also have to think.

Speaker 2 (09:01):
About the future expected value.

Speaker 3 (09:04):
Of just being alive in that very positive field, right
as being an insurance and so the name of the
game and insurance is to stay in the game. And
sometimes you have to even if all the analysis says,
you know, this is the right bet, this is the
right trade, this is whatever, Like there's another analysis going
is that the future of the future unknown expected value

(09:27):
of being alive in this field outweighs this any individual
bet or risk reward decision, right, And there's so many
other variables, like well, investors are very very path dependent, right,
if you lose for three years and then make for twenty,
you're not going to be around even if you've only
lost a little bit of money, because you're never gonna

(09:48):
get to raise of money to get the fun and
get to capital mass.

Speaker 2 (09:51):
But if you make, you know.

Speaker 3 (09:52):
But if you win for four four years and lose
for five and you'll still be around.

Speaker 2 (09:56):
Like they're very path dependent creatures.

Speaker 3 (09:59):
So there's just little peculiarities of how the system works,
how your brain works, how you have to look at
how other people perceive risk when you're taking risk, Do you.

Speaker 2 (10:09):
Have the right to take the risk? You know?

Speaker 3 (10:13):
Things like that is where I've had to make personal
decisions about the activities I do as and also like
trading decisions like, hey, it may even though this seems
like the right trade and the expected outcome is really high,
the risk of ruin as at our percent that.

Speaker 2 (10:32):
We can't take and the name of the game is
to stand the game.

Speaker 1 (10:36):
I think that's a really smart way of looking at this.
And now I also understand why you've been successful as
a poker player, because I think that that's something that
a lot of poker players. More we can talk about that,
but more successful than I think people give you credit
for as a poker player. And I think that a

(10:57):
lot of poker players understand risk reward, but actually have
that piece of the puzzle missing, which is that the
name of the game is to stand the game. And
a lot of players go broke and they take there's
this thing in the poker community that this perverse pride
and oh, I've been broke x number of times. And
you know, my mentor in poker, Eric Sidell, has always

(11:20):
told me that I think that he thinks that that's
not a great way of looking at it. He's never
been broke, right, that that's not an image you want
to cultivate. But a lot of players they, you know,
they take the risks and they don't they don't realize
that you do have to stay in the game. And
we don't know their names, right, A lot of a
lot of the players that we're very promising people don't

(11:41):
remember who they were anymore. And now some of them
were very successful and then went broke and then we're
able to raise the second funds, so to speak, right
in the poker world. But I think that that's especially
for people who are in kind of risky professions, and
who are more comfortable taking risks. I think staying in
the game avoiding ruin is a really important and often

(12:03):
missing piece of the puzzle. And it's something that you've
done successfully professionally, even though you've taken some very big bets.

Speaker 3 (12:12):
Yeah, you know, And my natural inclination is, you know,
so be it because I have a you know, it's
I consider it a blessing. But like I have a
lower I don't give give a fuck. I mean higher
I don't give a fuck, and lower concern about what
other people think.

Speaker 2 (12:29):
Like I'm not afraid to look like a clown.

Speaker 3 (12:31):
I'm not afraid to express my view that in a
controversial arena, I was very very happy broke with no money,
and so you know, I'm like, I don't want to
go there, but I'm okay with it. And a lot
of other people, you know, they avoid certain risks, whether
it's taking a job or starting a business, not because

(12:51):
they can't stomach the financial aspects of it.

Speaker 2 (12:53):
They can't stomach the emotional.

Speaker 3 (12:55):
Aspects of it, the shame, the ridicule, the feeling like
a failure, et cetera.

Speaker 2 (12:59):
I don't care this is the right trade, Like this
is what we do.

Speaker 3 (13:02):
You know, all boxers get punched in the face, so
all boxers get knocked down, right, you know risk managements
like uh, name of the games, stay in a game?

Speaker 1 (13:10):
How did I actually don't know this? How did you
get into poker? Kind of at the level that you
that you play because to me, and correct me if
I'm wrong, it seems like you've increasingly actually taken the
game seriously. Right, you play for fun, but you also
have studied, you have coaches, You do want to prove
yourself as a good player and not just oh you know,
this is some hedge fun guy who's coming into play poker.

Speaker 3 (13:32):
So I have the curse of two gears zero and
one hundred, right, like one or two and one hundred,
Like I don't have this modern gear.

Speaker 2 (13:40):
So for a lot of the early.

Speaker 3 (13:43):
Part of my uh, you know, let's say public uh
and even private poker thing, it's just like, let me
have fun, let me, let me goof off, let me
let me put people in tough spots and just go
off with the game. And then you know, I got
a challenged publicly to a heads up match with a handicap,

(14:04):
and he was such a massive favorite. He was going
to crush me. But it was a public thing, and
I was like, oh, okay, let's let's let's see if
this old dog can learn new tricks. And I put
it in the work to obviously make that like him
a massive.

Speaker 2 (14:19):
Underdog for the wager we put on.

Speaker 1 (14:22):
And by the way, you're talking about your heads up
match with Landon, tis right. Yeah, And he ended up
taking a buyout, so so you did. You did win
that match in that sense because he realized that it
was no longer a good bet.

Speaker 2 (14:38):
Yeah.

Speaker 3 (14:38):
The funny thing is when they structured that that all
the buyout things, they were worried I would just quit.

Speaker 2 (14:43):
Or not complete the bet.

Speaker 3 (14:44):
They didn't realize like I was going in the lab
and I was coming to crush, Like I'm coming to
win this bet outright and take all the money.

Speaker 2 (14:50):
So they they, uh, and you know I was.

Speaker 3 (14:53):
I was two sessions a day playing at night, like
you know, at least three hours a day.

Speaker 1 (14:58):
Of the only amazing And by the way, and you
have a job as well, No.

Speaker 2 (15:02):
I have a job.

Speaker 3 (15:03):
So it was it was my my wife did not
like that because I'd be up to like one am
hand review, you know, playing playing playing then hand review
and studying and like beating these things into my head
so that I could.

Speaker 2 (15:17):
You know, it actually kind of took the fun out
of poker.

Speaker 3 (15:19):
It was very robotic. You know, a lot of it
was very robotic with you know, random number generator, this
seren al comes up. It's like taking a test.

Speaker 1 (15:27):
And just for people who you know, haven't followed your
your poker career, the way that I have. The hand
that really stands out to me recently, which I think
shows that the old bill who who has captured some
of that fun at the poker table still alive and
well is when you were playing, I believe it was
on a stream at the lodge in a large cash

(15:48):
game and you went all in and you were bluffing,
and then you said, I have a plane to catch
because you were going to your your your buddy's wedding
or something, and so you just you went all in
and then you got up and you said, let me
know if he calls or not, and you just left.

Speaker 4 (16:02):
Yeah.

Speaker 3 (16:03):
I actually I was actually finding out whether he called
or not, watching it on the delay stream while trying
to get into the FBO like at the gate, like wow.
And the funny thing is like that, Wow, this is intense,
like this is real drama because I didn't know what happened.

Speaker 1 (16:17):
And it was real money.

Speaker 2 (16:18):
It was real No, No, it's definitely real money.

Speaker 3 (16:21):
I was so what happened is my friend Andrew Siegel
was opening first time for Tiffany Hattish as a comedian.
He's been a real estate guy his whole life. Like, yeah,
it wasn't a wedding, it was it was it was
a comedy. So he's like, this is his big debut.

Speaker 2 (16:37):
You know.

Speaker 3 (16:38):
He's like, I've been wanting to go on comedy for
a while. So I committed to go to his show
in Arizona. Okay, and we work backwards, you know. Can
I go to lodges? It's fine. I can play with
you guys, but I must absolutely meet my wife at
this time. You can't miss He's the opener. It's not
you can come late and you catch on the show.
You have to catch the opener. And I show up
for my friends. I believe that like half a life

(16:59):
is showing up Like so in these big, expectedly big moments.
If I make a commitment, it really takes something very
serious for me not to show up to you for it.
And so my priority stack showing up my friend fore
beats anything. But you know, I'm like last hand guys,
like I'm stuck. I'm trying to get in there and
trying to get my money and I'm like last hands guys.
I let the producers know because they don't let you

(17:19):
take your phone in outside send the memo when I
have to go at this time. And so that's what happened.
And that was the hand and so a lot of
people's like, did you plan that was angle? I was like, no,
I had to go, and so I put him in
the blender with this big bluff, right.

Speaker 2 (17:33):
I know he has, I know he has.

Speaker 3 (17:37):
I don't overpair, and I just I just was like, oh,
he's going to take a while to think about this.

Speaker 2 (17:44):
I got to get out of here and I just left.
It's great. It's great TV. I guess you know. I
know it's great TV because I was watching sweating. I
was like, wow.

Speaker 3 (17:54):
I just I thought I was like, oh, he's probably
gonna call, and then he folded.

Speaker 2 (17:57):
It was it was yes, it was.

Speaker 1 (18:00):
A beautiful moment, and you were unstuck for the session.
We'll be back in a minute.

Speaker 3 (18:20):
You know, I think to look at risk yourself to
look at variants as well, like singular questions, do you
take the guarantee or do you go?

Speaker 2 (18:28):
Right? How many?

Speaker 3 (18:30):
Like a casino wants you to play for hours? Right,
They're not gonna let you put down twenty million dollars
on what bet? Right like that the variance isn't there
for them, is too risky for them, right. But if
you say, hey, I'm going to play twenty million for
one hundred thousand hands.

Speaker 2 (18:49):
They'll structure that for you. Right.

Speaker 3 (18:51):
And so the question is is in my lifetime how
many of these type of bets this expected outcome am
I going to see?

Speaker 2 (19:01):
Am I going to see one? One hundred of them?
One thousand, ten thousand?

Speaker 3 (19:06):
I think that kind of goes into people's calculus, right,
it should.

Speaker 2 (19:12):
It should, right?

Speaker 3 (19:12):
And so not just the risk like oh I'm fifty
point six percent favorite.

Speaker 2 (19:18):
Everything, Let me just risk everything, you know what I mean?

Speaker 3 (19:20):
Like, but like, oh I'm fifty six point six favorite,
somebody's going to do play this game where you're that favorite.
They're going to do it a zillion times. And you
know it's at a unit that doesn't bank ruby but
it can hurt, you know, like.

Speaker 2 (19:33):
It can handle it.

Speaker 3 (19:34):
And then you get introduced concepts called the Kelly criterion,
like how much do you wager of your stack of
your life given your.

Speaker 2 (19:44):
Given the odds, right?

Speaker 3 (19:46):
And the short simple answer is the percentage of your
bankroll your risk is is the percentage of your edge.
So it's it's fifty one forty nine. You're risking two
percent of your bankroll per per incident.

Speaker 2 (19:58):
Right.

Speaker 3 (19:58):
So I think these questions where they say, you know,
ten million or four million, it's like, my bankroll is
five grand guy, you know what I mean?

Speaker 2 (20:07):
Like you know, like they're like, I'll take the garantee. Right.

Speaker 3 (20:10):
If you say, yeah, you get to run this scenario
a thousand times and then we'll add that up. Then
I think people make a better decision. They'll do the
math decision, right.

Speaker 1 (20:23):
Yeah. I think that that's a really important point that
in life we often don't get enough chances for the
variance to even out because as you know, you know,
the only the only way to fight variance is through volume, right, So.

Speaker 3 (20:39):
Yeah, you need a lot of large numbers. And you
give these single incident questions to people and they're like,
how do I apply the Crawley criterion when the mount
we're wagering here is you know, one thousand x my
bank wroth.

Speaker 1 (20:54):
But so in your professional career, though you've sometimes made
very big taken very big risks on situations, and you're
you're someone who trades on information right, and trades on
events that happen that you see and you believe you
have more information, you understand them better than other people,
and so this is not a situation that's ever going

(21:15):
to repeat, right, Like so for instance, when you in
two thousand and eight, right with Goldman's acts, like that
two thousand and eight isn't going to happen again, Or
when Russia invaded Ukraine. And I talked about this briefly
in the past, but I think that that's a really
kind of important recent news event for you where you
were able to make a lot of money based on

(21:36):
seeing this reacting kind of taking the information the beginning
of the COVID pandemic, Like, there are these inflection points
where something is happening and someone like you, whose job
is to actually be paying attention to these to these events,
to macro trends, can make a decision even though you
know that decision is never going to be repeated, Do
you risk more of your Bankrell? Do you think about

(21:58):
those situations differently?

Speaker 3 (22:00):
Well, the way I think about it this way is
there's the narrative behind it, the story and then the setup.

Speaker 2 (22:06):
And so.

Speaker 3 (22:07):
In my profession, you know, it could be two thousand
and eight crisis, hurricane, a freeze, et cetera. Where you
have this certain expected outcome. You know, this is the
probability event happened, and this is the expected outcome. So
the narrative may change, but I'm going to get a
lot of those different things. I'm not going to see
a two thousand and eight, but I'm going to see
a two thousand and eight risk reward scenario and ev

(22:29):
set up again, right, so.

Speaker 2 (22:31):
I will I will get that.

Speaker 3 (22:33):
And you know that one you're gonna get the law
of large numbers that way, right, You're not gonna get
not getting the law of large numbers in that narrative,
but you're gonna get love of large numbers.

Speaker 2 (22:43):
And that's set up for a lot of traders. It
still hurts, you know, emotionally like that. And that's the
thing with a you know.

Speaker 3 (22:51):
Risk there's a lot of people who are bright, very
smart professors, people brightther than me. That can't be traders
because the emotional UH risk ward does not line up
with the actual UH frequency of you know, good days
or qui bets. So like, if I think you've heard

(23:13):
me say this before, Like they've done studies where the
average person needs five good events, five to seven good
events to make up.

Speaker 2 (23:19):
For one bad event.

Speaker 3 (23:21):
Right, So you know people talk about in relationships, like
if you have a fight and you're in the wrong
with your woman, you can't.

Speaker 2 (23:27):
Just give roses.

Speaker 3 (23:28):
You have to give a roses for five days or
five different treats or something like that.

Speaker 2 (23:32):
Right, if somebody lost, you know, had.

Speaker 3 (23:35):
A bad day or whatever, they need five good days
to like equate to the one the one bad days. Trading,
that's impossible, right, nobody is above sixty percent in trading.
When people have that you know, emotional ratio of needing
five or seven good events to every bad event, it

(23:56):
just won't work out in tradings. And so that will
weigh on their cognitive abilities to make rational decisions in
the future and just drive them crazy.

Speaker 2 (24:05):
It just won't be worth it for them.

Speaker 3 (24:06):
They're miserable, they're angry, it's affecting their family life.

Speaker 2 (24:09):
Et cetera.

Speaker 3 (24:09):
And they're in trading not because they want to punch
buttons in computer They're there to get money to have
a good life, and if it's destroying their life, they
need to they didn't move on.

Speaker 1 (24:19):
Have you become better at managing that emotional side? Or
is that something that you've always been pretty good at?
So is that something that you feels like a part
of your personality or is it or is it a
skill that you've had to develop.

Speaker 3 (24:30):
I think going back to my father and you know,
not necessarily worrying about what people think or whether people like, oh,
you're a loser, you're failure.

Speaker 2 (24:38):
That really helps me because.

Speaker 3 (24:41):
I think people can handle the monetary risk. I think
it's the emotional risk. And in that emotional risk, it's
not like, oh I lost a bunch of money. I'm
an Idiot's like, oh, these guys are going to talk
about me. They're joking about me. You know, market's cruel.
People like to talk smack. There's always haters, and if
you don't give a shit, that kind of disappears, right like,

(25:01):
it kind of disappears. And I've always been kind of
you know, fuck it, we're all going to die type
of guy, like you want to have an adventurous life,
you want to have a great life, you should be
doing these things. And so that has helped me if
I've always had that and I've honed it by like
reading the stoics and getting other people's take on that

(25:23):
attitude to actually be even better. Right, we can always
be a little bit better, And I think the more
I'm like that, the better trader I will be.

Speaker 1 (25:33):
Yeah, No, that makes a lot of sense. And it
also makes sense to me that you would take these
risks in an area where you have an edge. This
is information that you know how to act on better
than almost anyone else. But you wouldn't necessarily take a
risk that was as big and something else. And this

(25:56):
is not This is a way of managing I think
the emotional element. But it's a little bit different.

Speaker 3 (26:01):
Yeah, So the going back to like, you know, risk
reward and how I think about risk, right, because you
have to know what's your risk and what's the reward, right,
And so a lot of times we make decisions and
trying to quilibrate that it costs all decisions. I use
a motorcycle. Actually, my friend Andrew was the first one
who used the motorcycles. Like, I like writing motorcycle. It's

(26:21):
really nice. You see all around you. You feel empowered
or whatever.

Speaker 2 (26:25):
But I think the odds are like one in ten thousand.

Speaker 3 (26:29):
You die if you ride a motorcycle for a year. Right,
That is kind of my benchmark right on. You know,
I do get this reward, it would be enjoyable, but
it's not worth the risk. So I apply that to everything.
So I need to either have a motorcycle type reward
with less risk right to order to do an activity right,

(26:51):
or a much greater reward right. And so one of
those was skydiving.

Speaker 2 (26:55):
Right.

Speaker 3 (26:56):
First time I went skydiving, amazing, adrenaline rush pumped for
a week. Second time it was great, wasn't amazing? And
somebody said, you want to go skydiving again? I was like, no,
the reward is diminished and the risk is still the same.
I'm not going to skydive me Like it's it's not
worth it to me anymore, you know. And so I
use that all the time, Like my friend's like, oh,

(27:16):
we're going to go jump off this cliff and you know,
jump into the water over here when we're on vacation
and I'm looking at the cliff and I'm thinking to myself,
it's okay, It's like it would be fun but riskward.

Speaker 2 (27:29):
Now it's out there, it's not.

Speaker 3 (27:30):
First of all, it's not as fun as riding a motorcycle,
and you know, the risk seems weird, and so always
thinking about the risk reward financially, emotionally, physically, everything at
the time, well, I think leads you to a happier
and more prosperous life. Yeah, absolutely, according to your own values,
right Like some people like I absolutely love riding a motorcycle,

(27:51):
then it's worth it to them. I tell people like
I don't smoke cigarettes because the reward of smoking cigarettes
is like I don't like it enough, right Like I
don't like to me, it's nasty and whatever, and so
there's almost very little reward and the risk is very high.
But if I really love smoking cigarettes, like that fulfilled me.

Speaker 2 (28:08):
It's my fucking cigarett, you know what I mean, Like,
it's just rich reward.

Speaker 1 (28:15):
We'll be back after a quick break. I want to
briefly mention just because I think this is a theme
that informs a lot of what you do. Die with zero,

(28:36):
because that is kind of an underlying theme of that book,
and for people who haven't read it, you can of
course quickly say this thesis although the title of the
book is the thesis in many.

Speaker 3 (28:50):
Ways, right, right, And so I guess the book is
about optimizing your life according to your own values. It's like,
I don't push how you should live. I've thought about
the mental models you should use in order to get
the most out of your life, no matter what fulfills you.
And so the think about the arc of your life
over time, you know, come to conclusions that your choices
and your experiences that you have or is your life.

Speaker 2 (29:12):
That's the summation of your life.

Speaker 3 (29:13):
And you know, you think about what fulfills you in
each time period, and these time periods pass. And so
if I optimize, if my life is the summation of
these time periods, and then I want to use all
my resources that I have, my wealth and health and
time throughout my life to drive fulfillment.

Speaker 2 (29:31):
How do I think about that? Right?

Speaker 3 (29:32):
And so one of the things you know, we were
talking about trying to understand risk reward, you got to
understand variables is when you have an experience, when you
go surfing, et cetera. It's not just the enjoyment of
experience at that time. It pays a dividend in the future.
You talk about it, you make friends, and I call
that the memory dividend, right, Like accessing that memory produces

(29:54):
fulfillment now, right, I crassly joke. Anybody who's masturbated understands
the memory dividend, right, and so they understand it in space, right.
And so when you invest in experiences, you get dividends,
whether that you know, going on you know, walking with
your daughter, doing charitable events, going to clubs, whatever. Most

(30:15):
of the time you talk with your friends, a significant
percentage of that conversation is about things that have already happened,
not things that are concurrently happen and are going to
happen in the future. And so getting those variables right
and thinking about, according to my values, what's the right
risk reward decision, what's the right allocation of my time
at this at this period of my life? How does

(30:37):
that How does this counterfactual regret minimization algorithm for net
fulfillment work? As as I as I progress from my
life from now to the grave, and so that helps
me think about do I show up this, per instance,
fiftieth birthday, Do I do I go to this wedding?
Do I play cards? Or do I watch a movie

(30:59):
with my wife? Or do I do you know, what
do I do? In these situations that don't necessarily have
hard numbers, like a roll of a dice or you
know what I mean, it's a flush draw and I'm
forty percent to make it or whatever it is you
know at the time, or combo draw, whatever it is.
When you don't have these hard numbers, you have to
think about the value system.

Speaker 2 (31:20):
What's the risk reward? I will get this, I won't
get this.

Speaker 3 (31:22):
If I do the ski trip now, I have the
memory dimbdend for ten years versus investing the money and
taking two key strip ten years of my life. But
you know, let's say I'm seventy two ski trips ten
years from now, it doesn't really make sense. You know,
I might not be alive, my knees not might work,
et cetera. If I'm twenty, maybe it does make sense.
Maybe nose to the grindstone, you know, do something else

(31:45):
that's not ski related with a group and then taking
everybody on two ski strips later. Who knows, I don't
know the answer. It's more of a methodology to think
about things in order to get the maximum high score,
and the high score in this case is net fulfillment.

Speaker 1 (32:00):
Yeah, for sure, for sure. I mean some of the
decisions you've made. One of my favorite things that you've
done recently in recent years is your purchase of The
Sugar Shack, which is this iconic painting by Ernie Barnes,
and you paid a record amount of money for that,
record breaking for him. And my favorite thing about the

(32:23):
story was that, so you flew to the auction to
be there in person with your fiance and apparently before
the bidding started you told her that, babe, you know,
if I pass out or anything else happens, just keep bidding.
Those were your instructions, because you're like, we are winning
this thing no matter what. Yeah, we talk. You came

(32:44):
there to buy that painting, and you were bidding against
George Lucas.

Speaker 2 (32:48):
I think, I don't know, I mean, we think we think.

Speaker 1 (32:51):
You were bidding against someone with a lot of money. So,
so walk me through though those instructions and that thinking
that you know, if I pass out, just keep bidding.

Speaker 2 (33:02):
Yeah. So I uh, I wow. I don't get emotional
about this.

Speaker 3 (33:08):
It was one of the things that I felt was
like a treasure. I think a lot of other people
outside of black art collectors or art collectors, are very
familiar with that painting. They've seen it in Good Times, it's
been on an album cover, it's it's in the it's
in the consciousness of America, and it's a unique piece.

Speaker 2 (33:24):
Of American art, not just African American mart but American art.

Speaker 3 (33:28):
Because the narratives in those paintings are only are you
uniquely American? Right, like an ice skating or eating an
apple or whatever, that's global, but the themes going on
in a lot of the African American arts are uniquely Americans,
like jazz a unique American art form, right. And so
with this backstory in this culture and this, you know,

(33:50):
might go like I wanted up one day as a
kid watching Good Times and seeing that painting at the
end of you know, every episode that I watched, you know,
I was like, Wow, I made it. I can I
wanted this piece, and I'd been collecting Barnes earlier. So
one of the risks I avoided was being online. I
didn't want anything go wrong. What if the computer went out,
or being on the phone, what if the phone went down?

(34:12):
What if what if you know, the internet service goes
down or whatever, because I'm on a cell phone. And
I was like, I can't risk it. I can't risk it.
We're gonna fly up the day before. So there's one
risk thing that I eliminated because how am I going
to feel if like I'm bidding and I don't get
to buy and then I don't get it. I would
I would just be distraught. So we flew up the

(34:35):
night before so we could be there. We walked around
our galleries, and we show up into the auction house
and that's all I'm coming to get. I thought it
was going to go for much cheaper than it then
it went. But I started to get suspicious when there
was a film crew filming, like the Barnes on the
on the thing, and so then the document Cody, the

(34:56):
guy who did the Genius documentary about Kanye West, was there.
He's like, he's doing a documentary on Barnes and it's
in the Night and this is Paintings in the Night auction,
which is really reserved for higher price art, but it
has an estimate like of a couple hundred thousand dollars
and I'm just like, what are they talking about?

Speaker 2 (35:17):
And so I knew something was up.

Speaker 3 (35:19):
I think it was a their psychological employ to get
a lot of bidders to show up to think that
they were going to get it going and get the
crowd going.

Speaker 2 (35:26):
And so I saw myself.

Speaker 3 (35:31):
As as my friend Rick Lowe, who's an artist, ran
Project row Houses as a genius Arthur Award. I bought
a piece of art before in two thousand and eight
financial crisis from another artist called Biggers, and he was
angry and I said why, And he says, because the
role of the art to collector is to signal to
the market that these works are worth preserving. You are

(35:51):
a steward of these works, right, And so the art
market sends a signal to the world and everybody that.

Speaker 2 (35:59):
This is the culture. These are the things that are
worth preserving.

Speaker 3 (36:02):
Like when you go to see in museums or what
people commissioned or bought, there are lots of works that
are not there, right, And the people from a thousand
years whatever, they decided what was worth preserving. Right, civilizations
come and go, the art remains, right, And so he
was pissing.

Speaker 2 (36:19):
I took that to heart, and I was like, I am.

Speaker 3 (36:20):
To be the steward of this work. It is not
valued properly, right, like, especially what I'm on board. So
I decided like this, this was it, This is the
piece I wanted, and I to my I was like,
I was very nervous. I was like, listen, if anything
happens to me, just keep bidding, don't worry about me,
keep bidding, because you know, I was worry about you.

Speaker 2 (36:41):
Whatever. And and then off we went.

Speaker 3 (36:43):
I thought, you can hear the auction, there's like somebody
did a cut. They're like it's just erupted, like you know,
hear me go five hundred thousand, you know, just trying
to like clear the.

Speaker 2 (36:53):
Room, and it just keeps going.

Speaker 3 (36:54):
I'm like, holy shit, you know one, you know, and
it's just going crazy. So I was like, okay, let
me get it to a let me scatter the roaches,
you know, get them out of here.

Speaker 2 (37:03):
And this other bidder.

Speaker 3 (37:05):
They had basically the same idea, but uh, I remember
during the middle of it, thinking like they would you know,
between seven and eight million. I took a long pause,
you know, they wait, and I was like, Okay, what
am I going to sell in order to buy this thing?

Speaker 2 (37:23):
Like I need to you know what I mean?

Speaker 3 (37:25):
Who am I going to borrow money from in order
to get liquid to buy this painting?

Speaker 2 (37:29):
And then how high am I?

Speaker 3 (37:31):
You know, like it got into numbers like what am
I selling?

Speaker 2 (37:34):
How am I going?

Speaker 3 (37:34):
Can I actually pull this off? Type numbers? But clearly
this professional bidder representative was was like he was getting annoyed.

Speaker 2 (37:44):
It was like because.

Speaker 3 (37:45):
Nobody expected this, Like you ga saw there's this TV
screen Hong Kong's up there right, you know, the Asian
bidders and all their agents are kind of looking at
us in the screen right this big giants it's like
a big brother screen, a fort wall and this pit
and everybody's looking at me and looking what's going on?

Speaker 2 (38:00):
And they're like what the fuck is going on here?

Speaker 3 (38:02):
You know, like nobody's and this guy has got to
be like, who the hell are you? Like this guy
in like jeans and a ball cabin, you know, just
never seen you before?

Speaker 2 (38:12):
Who are you?

Speaker 3 (38:13):
And he turns to me, he goes, I'm not going
to stop bidding, right, He turns to me, turns around
because I happened to be over here, and he tells me,
I'm not going to stop bidding, and I said, then
I'm going to make you pay, you know, and so
and then off we get again. You know, then the
rounds kept going, right, that was around seven or eight million.
You know, It's like, if you're not gonna stop bidding,
you're gonna pay a lot, buddy, because I want this.

Speaker 2 (38:33):
This is for me, you know. And and and ultimately.

Speaker 3 (38:39):
Fortunately they quit at the number they quit, and it
was amazing.

Speaker 1 (38:44):
That's it's an amazing story. And but and the outcome
actually really nicely summarizes so many of the things that
we were talking about. You know, what you value, how
how you're valuing kind of the risks and the rewards,
and that you were valuing this specific painting for very
different reasons then the professional bidder, who also clearly understood

(39:05):
that this was a remarkable work but also needs to
fill in the museum has other priorities. And that kind
of calculus really really gets to the heart of the thing.
And I love how you mitigated the risks and you know,
the keep bidding. You were even you know, mitigating the
risk of heart attack, yeah.

Speaker 3 (39:21):
Read a heart attack or passing off fate or like
just hyper like whatever could happen like and I know
I don't. I don't get nervous, Like I'm not like
it's like I've gone I've been a situation where you know,
we've had a massive year. My CFO is like, we're
gonna have to turn close the fun. We're gonna let people.
I'm just like, this is what we do.

Speaker 2 (39:38):
I'm going to chop with.

Speaker 3 (39:39):
Of course we made all the money, triple the money back,
et cetera. But you know, people get really down or
really nervous or whatever, and I'm just kind of like,
it is.

Speaker 2 (39:49):
What it is.

Speaker 1 (39:49):
Well, congratulations, I'm going to get that the painting ended
up in the right hands. Bill, thank you so much
for coming on Risky Business and sharing your wisdom with us.
I really really enjoyed this conversation.

Speaker 2 (40:01):
Yeah, thank you for having me. I appreciate it.

Speaker 4 (40:12):
Risky Business is hosted by me Nate Silver and me
Maria Kanakova. The show was a co production of Pushkin
Industries and iHeartMedia. This episode was produced by Isabel Carter.
Our associate producer is Gabriel Hunter Chang. Our engineer is
Sarah Bruger. Our executive producer is Jacob Goldstein.

Speaker 1 (40:30):
If you want to listen to an ad free version,
sign up for Pushkin Plus. For six ninety nine a month,
you get access to ad free listening. Thanks for tuning in.
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