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2:00

APSA. approval. Bloomberg audio studios. Podcasts, Radio News. This

2:03

is Masters in Business with Barry

2:05

Ritholtz on Bloomberg Radio. This week

2:07

on the podcast, what a delight.

2:10

What a delight! Extra special guest

2:12

Jim O'Shaughness. His book that I

2:14

came to know him with first.

2:17

was what works on Wall Street,

2:19

which has been just a perennial

2:21

seller. I think it's in its

2:23

fourth or its sixth edition, and

2:26

really influenced several generations of quants

2:28

on finance. Oh, shown to see,

2:30

asset management became a leader in

2:33

direct indexing, eventually was bought by

2:35

Franklin Templeton. leading him to launch

2:37

OSHA on a Sea Ventures, OSHA

2:40

on a Sea Fellowship's infinite loops

2:42

podcast, just so many different things.

2:44

His new book is delightfully titled

2:46

Two Thoughts, a timeless collection of

2:49

infinite wisdom and reflects many of

2:51

the insights and just thoughtfulness that

2:53

Jim shows in everything he does.

2:56

I always find it delightful to

2:58

have him on the show and

3:00

the show. You can tell how

3:02

much I appreciate him just by

3:05

the conversation meanders wherever it goes

3:07

and I occasionally look at my

3:09

list of questions but really I

3:12

just want to see where Jim's

3:14

mind is going to take it

3:16

and come along for the ride.

3:19

I thought this was delightful and

3:21

I think you will also with

3:23

no further do my conversation with

3:25

Jim O'Shaughness. Barry, I am always

3:28

looking forward to these conversations. That's

3:30

great to be back. It's a

3:32

pleasure for me also. You and

3:35

I go way back, way, way

3:37

back. And it's kind of funny

3:39

like 25 years later. I'm like,

3:41

oh, how do you know Jim?

3:44

Oh, we met in the green

3:46

room. you know right after the

3:48

dot-com crash is kind of it

3:51

was kind of funny but let's

3:53

talk a little bit about all

3:55

the different businesses and ventures that

3:58

you're you're involved with so I

4:00

knew you right around the time

4:02

you were getting ready to depart

4:04

Bear Stearns. You had Bear Stearns

4:07

for like a decade or so?

4:09

No, about five and a half

4:11

years. Okay, so in the in

4:14

the mid 2000s, and you had

4:16

the great insight and business acumen

4:18

to tap out of Bear Stearns

4:20

in 2007 with all of those

4:23

options that you had and exercise

4:25

the option, sell them and launch

4:27

your shortness the asset management. So

4:30

you win on the way out,

4:32

you win on the way into

4:34

starting the new firm, tell us

4:36

a little bit about the early

4:39

days leaving Bear Stearns and setting

4:41

up OSAM. So first let me

4:43

correct the, everyone assumes that I

4:46

saw the great financial crisis coming

4:48

and therefore wanted to spin out

4:50

of Bear Stearns. What do they

4:53

say? If the story conflicts with

4:55

the legend, print the legend? The

4:57

legend really isn't correct though. We

4:59

had begun conversations with Bear Stearns

5:02

folks months and months before the

5:04

financial crisis came on the scene.

5:06

And it was essentially a very

5:09

amicable parting. As you note, when

5:11

we spun out, we kept all

5:13

of our Bear Stearns accounts. uh...

5:15

continued to work with all their

5:18

uh... private client service people over

5:20

there uh... so it was very

5:22

very amicable but of course because

5:25

the great financial crisis came along

5:27

and bear had those CDO funds

5:29

that a little bit of a

5:32

problem it was it was just

5:34

irresistible for news people to say

5:36

I had one reporter sit with

5:38

me for an hour and a

5:41

half and all she kept doing

5:43

was come on tell me the

5:45

truth tell me the truth tell

5:48

me the truth you know it's

5:50

funny because when when we look

5:52

at certain books that get the

5:54

timing of things right or completely

5:57

wrong people forget A book just

5:59

doesn't appear wholesale out of thin

6:01

cloth. It's the idea has to

6:04

come along and then you got

6:06

to get a publisher that wants

6:08

it unless you're going to self-publish.

6:10

Then you got to write it.

6:13

So it's like a one or

6:15

two year lag. I would imagine

6:17

pulling out a substantial division from

6:20

a major brokerage firm. doesn't happen

6:22

overnight. It's going to be like

6:24

a six or 12 month process.

6:27

Absolutely, because you have to have

6:29

everyone with the oars going in

6:31

the same direction. You want to

6:33

make sure that it is agreeable

6:36

and everyone is whether they're unhappy

6:38

that you're going, they're happy with

6:40

the deal that allowed you to

6:43

go and so I took extra

6:45

time to make sure that that

6:47

happened because I loved the folks

6:49

over at Bayer and it was

6:52

really just my own desire to

6:54

be an entrepreneur again and and

6:56

they really got that and so

6:59

very amicable but as you as

7:01

you know those things take a

7:03

long time to get negotiated out.

7:06

Yeah you know to me the

7:08

thing I'm I was always kind

7:10

of sad about with the fall

7:12

of bare stones eventually picked up

7:15

for pennies by Jamie Diamond and

7:17

J.P. Morgan Chase and then even

7:19

Lehman Brothers. I know a lot

7:22

of great people in a lot

7:24

of different divisions. You know we

7:26

all have mentors all over the

7:28

street that even if they're a

7:31

counterparty or if they're a salesperson.

7:33

There were things to learn from

7:35

folks, and Bear and Lehman were

7:38

two, like, giant-storied names. And, I

7:40

mean, obviously, there was a massive

7:42

disruption throughout society. But the tragedy

7:44

that a lot of lay people

7:47

don't know are really good people

7:49

doing really good work Get they're

7:51

the collateral damage from someone else's

7:54

screw up totally agree and the

7:56

you know, obviously just my personal

7:58

opinion But I think at that

8:01

particular point in time all of

8:03

the investment banks were bankrupt or

8:05

insolvent and well some were a

8:07

little more insolvent than others yeah

8:10

I agree I agree and and

8:12

so it was almost a bit

8:14

like luck of the draw that

8:17

Lehman and Bayer were the ones

8:19

to go down right Bayer went

8:21

down early enough that it was

8:23

salvageable and then a little known

8:26

story that a lot of people

8:28

are unaware of when I was

8:30

writing bailout nation and doing my

8:33

homework It turned out that J.P.

8:35

Morgan Chase had a little derivatives

8:37

flare-up like years earlier. And I

8:40

don't remember if it was Jamie

8:42

Diamond or one of his lieutenants,

8:44

but someone said, hey, this is

8:46

a mess and this is really

8:49

potentially damaging. And it might have

8:51

been Diamond who said, sell it

8:53

all, I don't care the price,

8:56

if you have to take a

8:58

10 or 20% haircut, I want

9:00

all this off the books. And

9:02

that's what they did. And so

9:05

when the world went to hell,

9:07

They were, they picked up Washington

9:09

Mutual, they picked up Bear Stearns,

9:12

they got to cherry pick the

9:14

best of the best at... pennies

9:16

on the dollar and that's why

9:18

JP Morgan is the monster success

9:21

it is today. Well Jamie is

9:23

a super smart guy and that

9:25

does not surprise me at all.

9:28

You know, the joke around Bear

9:30

Stearns at the time was that

9:32

Jamie really the real reason he

9:35

wanted to buy Bear was he

9:37

wanted the building. Right, right. Which

9:39

is now overshadowed by their brand

9:41

new headquarters. I know. But that

9:44

was a great octagonical building which

9:46

we could see. from our farm's

9:48

windows on Brian Park with the

9:51

glass turret. It was a beautiful

9:53

building. And you walk in and

9:55

it's like, you know, there used

9:57

to be Wall Street and then

10:00

there was, you know, the Morgan

10:02

Stanley and Lehman Brothers, sort of

10:04

off of, uh... Midtown, Times Square,

10:07

Times Square, right? And then this

10:09

was just, all right, so very

10:11

prescient before Vanderbilt was even a

10:14

thing. That's right. And there they

10:16

are. Now one Vanderbilt is a

10:18

monster. So, so let's bring it

10:20

back to what... you're doing so

10:23

you leave there you launch oh

10:25

Sam you've already had great success

10:27

with what works on Wall Street

10:30

what made you think I think

10:32

we're gonna develop a series of

10:34

quantitative approaches to managing money wow

10:36

so that was a dinner when

10:39

I was a teenager my grandfather

10:41

had been very successful He was

10:43

an oil speculator. Uh-huh. And he

10:46

kind of beat the pledge guys

10:48

by about 70 years. He proceeded

10:50

to give away the vast portion

10:52

of his fortune during his own

10:55

lifetime. Was it really a fortune?

10:57

It really was. No kidding. And

10:59

what he couldn't give away, he

11:02

put into a foundation, the I.

11:04

A. O'Shaughnessy Foundation, which I think

11:06

today is still about a hundred

11:09

million dollar foundation. No kidding. But

11:11

he made his five kids, the

11:13

trustees. And so once a quarter,

11:15

there would be a dinner and

11:18

it would rotate. I was brought

11:20

up in St. Paul. And so

11:22

during the St. Paul rotation, I

11:25

got lucky enough at, I think

11:27

it was 16, to get invited

11:29

to the adult table. And of

11:31

course, like, I'd want it to

11:34

be an adult. I loved going

11:36

to my parents' cocktail parties and

11:38

talking to adults. And so I

11:41

was really excited. And literally I

11:43

was put down next to my

11:45

uncle John and my dad and

11:48

I'm listening and they're talking about.

11:50

IBM, but they're just talking about

11:52

the CEO. Uh-huh. They're not talking

11:54

about how much do they make?

11:57

How much do you have to

11:59

pay for every dollar of earnings

12:01

or sales or evada? And I

12:04

kind of raised my hand and

12:06

said, Dad, Uncle John? Don't you

12:08

think it might be a better

12:10

idea to look at it by

12:13

the numbers? And they dismissed me.

12:15

This is 1976, right? So I

12:17

decided- What's a plan? Yeah, exactly.

12:20

Well, exactly. And so I decided,

12:22

you know what? I'm gonna go

12:24

look into this. So I took

12:26

myself down to the James Jay

12:29

Hill Research Library in downtown St.

12:31

Paul. And I thought I was

12:33

gonna be really ambitious, but I

12:36

am- potentially the world's laziest man.

12:38

So when I saw the 500

12:40

of the S&P, the S&P tear

12:43

sheet book, I'm like, oh, I'm

12:45

not, I'm not going to be

12:47

able to do that. So I

12:49

lighted on the Dow. 30 stocks,

12:52

right? Did the research found very

12:54

compelling evidence that what its PE

12:56

is really matters to your returns

12:59

going forward? very very high valuations

13:01

tended to crash and burn very

13:03

very cheap valuations tended to do

13:05

well but of course you know

13:08

Barry I was 16 17 much

13:10

more interested in girls right and

13:12

so after college got married young

13:15

I was like I've got to

13:17

revisit all this and got the

13:19

data set from Compu Stat and

13:22

essentially that became what works on

13:24

Wall Street. So wait, so what

13:26

would you study in college? So

13:28

the reason I am in economics,

13:31

I have a degree in economics.

13:33

The reason for that was I

13:35

had maybe six more credits, four

13:38

to six more credits in economics

13:40

than I had in history. So.

13:42

Although you might have been a

13:44

historian. Yeah, absolutely. Absolutely. Well, listen,

13:47

I think. good knowledge of history

13:49

is absolutely vital if you want

13:51

to be a good investor right?

13:54

100% yeah I mean like one

13:56

of the one of the Roman

13:58

wits said he who does not

14:00

understand what happened before they were

14:03

born remains forever a child. And

14:05

essentially I didn't want to remain

14:07

a child if you look back

14:10

at the markets history guess what?

14:12

History doesn't repeat itself, but it

14:14

rhymes. I mean you go back

14:17

to Isaac Newton losing a fortune

14:19

in the South Sea bubble and

14:21

like literally I always do this

14:23

joke because people get it. It's

14:26

like People were so in love

14:28

with that stock. Poets wrote poetry

14:30

about it. One went, fill the

14:33

South Sea Goblet full, the God's

14:35

shell of our stocks, take care.

14:37

Europa, please, accepts the bull, but

14:39

Jove with joy, puts off the

14:42

bear. And I used to, when

14:44

I was still at OSEM, I

14:46

used to say, I'm totally a

14:49

quant, but if somebody writes a

14:51

poem about a stock you own,

14:53

sell it. Right. Right. That's amazing.

14:56

And it's funny. You and I.

14:58

You and I. both have a

15:00

love of quotations. And I tried

15:02

repeatedly to track down the source.

15:05

of history doesn't repeat but it

15:07

rhymes it's always attributed to Mark

15:09

Twain or someone else and I've

15:12

never been able to really verify

15:14

that. Yeah quote investigator I love

15:16

that site yeah it's pretty good

15:18

they can normally get you to

15:21

the original citing of the text

15:23

what's funny about that though is

15:25

almost inevitably it's somebody you've absolutely

15:28

never heard right that's right and

15:30

I think that's why people like

15:32

when that sounds like something Mark

15:35

Twain would say right and but

15:37

then there's also the Mark Twain

15:39

Oscar Wild I mean there's a

15:41

bunch of them like any quote

15:44

that you really love and you

15:46

don't know who did it people

15:48

tend to say Mark Twain right

15:51

screw wild. The one from Twain

15:53

that stands out is, and I'm

15:55

gonna. mangle this. It's not the

15:57

things we know that get us

16:00

into trouble. It's the things we

16:02

know for sure that just ain't

16:04

shut. Yeah, that was actually a

16:07

character of Mark Twain's. Oh, really?

16:09

And he spoke like a southerner

16:11

of the late A 1900s. And

16:13

I think his last name was

16:16

Ward. He has some of the

16:18

great actual quotes that are really

16:20

his. What I love is like,

16:23

if you pick up a dog

16:25

in the street that is starving

16:27

and feed it, it will love

16:30

you. If you do the same

16:32

for a human, it will bite

16:34

you. This is the principal difference

16:36

between a dog and a man.

16:39

Which A is true, and B

16:41

leads to the newer line. If

16:43

you want a friend on Wall

16:46

Street, get a dog. And it's

16:48

really true. We're going to talk

16:50

more about quotes and books in

16:52

a moment. Before we do that,

16:55

I just want to bring up

16:57

the first book, what works on

16:59

Wall Street. That book not only

17:02

has been through multiple editions, it's

17:04

had legs, it's influenced an entire

17:06

generation or two of quants. What

17:09

was the most surprising thing about

17:11

what you found in the book,

17:13

and then it's subsequent... reception in

17:15

finance? So I think the most

17:18

surprising thing was a number of

17:20

people at various firms that I

17:22

was investigating working for before starting

17:25

my own, I mean I had

17:27

my own company but I was

17:29

getting a lot of offers primarily

17:31

because they knew the book was

17:34

coming right? Many of them when

17:36

they saw the galleys of the

17:38

book, the manuscript, the first thing

17:41

they said to me, Barry, was

17:43

we would love to hire a...

17:45

you but you cannot publish this

17:47

you're giving it away exactly exactly

17:50

exactly and I was like no

17:52

no no no no no you

17:54

you could have the greatest truth

17:57

in the world you can scream

17:59

it from all the rooftops you

18:01

can take full page ads in

18:04

the Wall Street Journal most people

18:06

are just gonna go me they're

18:08

not gonna do it it's so

18:10

true you know the My takeaway

18:13

from my first book, which is

18:15

now 15 years ago, was there

18:17

would be these debates about what

18:20

led to the crisis, what were

18:22

the factors, what were. And I'm

18:24

like, no, no, we've solved that.

18:26

I've addressed that. Let's move beyond

18:29

that. And the arguments didn't stop.

18:31

People just kept debating it. And

18:33

my takeaway was, oh, you could

18:36

just drop a truth ball on

18:38

people's laps. And if they don't

18:40

want to believe it, they're not

18:43

going to believe it. And that

18:45

was like. maybe I was naive

18:47

but you're 100% right the fact

18:49

that they thought you were giving

18:52

the secret away you could you

18:54

could here's a secret to investing

18:56

not maybe you'll do okay with

18:59

it but Nobody's gonna really adapt.

19:01

Well, you know, what's funny is

19:03

I would say to these people

19:05

it was one of the like

19:08

when I started out and actually

19:10

what works wasn't my first book

19:12

in West like the best was

19:15

which showed you how to clone

19:17

your favorite money managers Right by

19:19

looking at the biggest difference between

19:21

their portfolio factor distribution and then

19:24

using those as screens to get

19:26

a portfolio much like your manager

19:28

right note. We used to update

19:31

the clones verse the manager last

19:33

time we did it was years

19:35

and years ago right but the

19:38

thing that I found really interesting

19:40

was all of the clones were

19:42

beating the managers that they cloned

19:44

was that because of the fee

19:47

or was that because they're not

19:49

great sellers it was because of

19:51

our very human emotional decision-making almost

19:54

always under extreme stress. Models don't

19:56

get stressed, you know, they don't

19:58

get hung over, they never fight

20:00

with their spouse, they just keep

20:03

applying those criteria year in, year

20:05

out, and I think that the,

20:07

you know, we went through some

20:10

tough times after that book came

20:12

out, and people have different ways

20:14

of dealing with stress, and one

20:17

of them is not being good

20:19

at selling. So there's been a

20:21

number of studies and I don't

20:23

want to talk about my book,

20:26

we're going to talk about your

20:28

book, but some really fascinating things

20:30

you learn are when you look

20:33

at the academic research, fund managers

20:35

are actually surprisingly good buyers. Yes.

20:37

But they're terrible sellers. Yeah. And

20:39

part of the reason is the

20:42

emotionality of the sale. They tend

20:44

to panic out when they shouldn't

20:46

or through the opposite. Hold on.

20:49

right to the bitter end when

20:51

they really should well and also

20:53

it's just because it's just part

20:55

of our human OS part of

20:58

our human operating system right I

21:00

remember when Enron was going through

21:02

difficulties and I was set to

21:05

speak with a classic manager right

21:07

a fundamental guy and we were

21:09

gonna share the stage and the

21:12

first question went to me and

21:14

it was like are you do

21:16

you own Enron and my answer

21:18

was no the numbers are pretty

21:21

bad and so we don't and

21:23

he looked at me kind of

21:25

you know with the chuckle ugh

21:28

you quants you know and then

21:30

he launched into this description of

21:32

not only did he hold he

21:34

bought more and then he gave

21:37

this as the explanation I went

21:39

to a barbecue at the CFO's

21:41

house. The CEO was there, the

21:44

CFO, and I looked them in

21:46

the eye and I said, is

21:48

there trouble? And they assured me

21:51

there wasn't. And I'm just kind

21:53

of like sitting over there with,

21:55

oh, okay, just don't touch this

21:57

one. Maybe we could get a

22:00

short put on this. That just

22:02

like, I'll tell you something is

22:04

really funny. And this just goes

22:07

to how naive and stupid I

22:09

am or especially was. Early in

22:11

my career, I would listen in

22:13

on quarterly calls. And I would

22:16

believe every word I heard. Like

22:18

these guys aren't going to lie

22:20

to their investors, everything's going to

22:23

be great. And I very quickly

22:25

learns, oh, you're a terrible judge

22:27

of people, you'll buy anything that

22:29

a slick salesman is selling you,

22:32

you just have to stop, and

22:34

I just stop listening to calls

22:36

because I'm an idiot, I believe

22:39

what they say. I would rather

22:41

look at the numbers. And yeah,

22:43

I know the numbers can lie,

22:46

but not as easily. big part

22:48

of human OS, default to trust.

22:50

Well, we're social, we're social primates,

22:52

right? We grew up in primates,

22:55

yep. We grew up in groups

22:57

where trust was really, really important.

22:59

So your average human defaults to

23:02

trust. And by the way, that's

23:04

not a bad default. For the

23:06

vast majority of people, it probably

23:08

works better to trust who you're

23:11

listening to, right? One of the

23:13

things that we're looking at in

23:15

one of our divisions at Oshaw

23:18

City Ventures right now is voice

23:20

software AI that does stress analysis

23:22

on any type of media. So

23:25

obviously earning calls present themselves as

23:27

kind of number one. Yeah really.

23:29

And I gotta tell you Barry.

23:31

Wow. Exciting stuff? Oh my God.

23:34

Now how much of that is

23:36

nervousness about speaking to a large

23:38

audience? and nervousness because they know

23:41

something and they don't want to

23:43

disclose it. So as you might

23:45

guess, you do baselines, you... take

23:47

a recording where clearly either you

23:50

know you get some tape that

23:52

was before the call or you

23:54

know a speech that had nothing

23:57

to do with earnings and that

23:59

creates your baseline. And then you

24:01

get to see very very quickly

24:03

like spike We don't have any

24:06

worries spike Wow that sounds like

24:08

fun. Yeah, it is fun and

24:10

we're not sure how we're gonna

24:13

do it because we don't offer

24:15

Asset management services to people outside

24:17

of us honestly ventures That was

24:20

a deal that we made with

24:22

Franklin Templeton that we would not

24:24

launch but you could still do

24:26

a little come on doesn't don't

24:29

you at the edge sometimes to

24:31

say, hey X, Y, Z, stock

24:33

is wildly overvalued and the CFO

24:36

is full of it. Let's put

24:38

on some, let's buy some deep

24:40

out of the money puts and

24:42

see where this goes. You know,

24:45

if you keep a secret, we

24:47

might try that with some of

24:49

our internal capital. Let me know.

24:52

I'm right there with you. I

24:54

love the idea of that. Deep

24:56

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24:59

It's what makes Stiefel one of

25:01

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terms and conditions that apply to

27:39

the welcome bonus. Where

27:43

did the title come from? So

27:46

it came from a group of

27:48

my teammates at OSV. Essentially, I

27:50

have been a quote junkie all

27:52

of my life. Same. So I

27:55

have kept, I bear have notebooks

27:57

filled with quotes. Oh really? From

27:59

way back when I, I think

28:01

the first time I started it,

28:04

I was 21. Uh-huh. And so

28:06

I just love them and I

28:08

think that, you know, they can

28:10

pack a lot of a punch

28:13

if you put them together right,

28:15

if you curate them right, etc.

28:17

If you read what works on

28:19

Wall Street, I open every chapter

28:22

with a quote. I do that

28:24

a lot also. Right. Right. Let

28:26

me, let me ask you one

28:29

other question. about the title. So

28:31

one of the things that's fascinating

28:33

if you're if you like music

28:35

or poetry or even I'm gonna

28:38

go into the weeds Shakespearean in

28:40

i amic pentameter. I love all

28:42

those. Okay so there is a

28:44

rhythm to and I'm gonna write

28:47

this down so you know even

28:49

if you get this I want

28:51

you to know. There is a

28:53

rhythm to the phrase a timeless

28:56

collection of infinite wisdom that reminds

28:58

me of another book title, and

29:00

I'm curious if it was in

29:02

your mind when you came out

29:05

with this. Oh, you got me

29:07

on that one. A heartbreaking work

29:09

of staggering genius. A timeless collection

29:11

of infinite wisdom. It just leaps

29:14

off in that same rhythm. I

29:16

love that connection. I don't know

29:18

if that was a... No, at

29:20

least it wasn't purposeful. Really? Wasn't

29:23

purposeful? Because I've always loved that

29:25

title. Oh, it's a great title.

29:27

A heartbreaking work. Yeah. And it's

29:30

like you could go with a

29:32

different, it's a staggering work of

29:34

heartbreaking. It's like you could flip

29:36

it around. Yeah. But this phraseology

29:39

just leapt that leapt right out.

29:41

I am incredibly lucky to have.

29:43

just extraordinarily talented teammates. We have

29:45

a lot of writers on the

29:48

team, we have a lot of

29:50

editors, and you know, they would

29:52

just go at it. Like, what

29:54

about this title? What about? because

29:57

we had to call it two

29:59

thoughts, because this started Barry on

30:01

a whim. Well, I know, I

30:03

know you have been tweeting for,

30:06

I don't know, 10 years? Not

30:08

just a quote, and I was

30:10

doing that for a long time,

30:12

just throwing a quote up that

30:15

I thought was relevant, sometimes I

30:17

would stagger them out, like you

30:19

can plan a tweet six months

30:21

in advance. Hey, I don't know

30:24

what's gonna happen in August, but

30:26

I think this is relevant. You

30:28

have been doing two tweets for

30:31

forever. Yeah. And so it was

30:33

kind of like, you know, Ken

30:35

Stanley's book Greatness Can't Be Planned.

30:37

This is a perfect example of

30:40

that. So I just thought, you

30:42

know, what the heck? I'm going

30:44

to put up two thoughts and

30:46

I'll see if I like it,

30:49

if I keep doing it, I'll

30:51

just keep doing it, right? And

30:53

then all of a sudden, like,

30:55

the people that got attracted to

30:58

it were... There was a lot

31:00

of people and then I started

31:02

getting DMs on Twitter basically saying

31:04

hey if you would do this

31:07

in a newsletter I would subscribe

31:09

and Then one of my colleagues

31:11

was like well, let's do the

31:13

newsletter and in the newsletter. Why

31:16

don't we say hey, would you

31:18

like a book? and that's what

31:20

happened literally we iterated iterated and

31:22

ended up publishing the book so

31:25

that that's really interesting that that's

31:27

the genesis of the two thoughts

31:29

when you're picking a pair of

31:31

thoughts from the same author are

31:34

you looking for things that complement

31:36

each other are you looking for

31:38

their their most two most profound

31:41

statements how are you selecting A

31:43

and B for this author Yeah,

31:45

it's it's a little bit messy

31:47

to be really honest Because I'll

31:50

usually start with the notebooks that

31:52

have all my handwritten quotes out

31:54

when I copied the quote over

31:56

And sometimes I'll think ooh I

31:59

found like the perfect one quote

32:01

from this author and then I'll

32:03

spend some time going through the

32:05

rest of their work etc. finding

32:08

one that would complement it but

32:10

then sometimes some of the best

32:12

two quotes that work the best

32:14

they don't complement each other in

32:17

other words it's kind of like

32:19

hey you know history rhymes but

32:21

then the second quote is but

32:23

always keep your eyes on the

32:26

horizon. Right? Like, hmm. Two very

32:28

different, two very different things. And

32:30

so I wasn't precious about it

32:32

at all. Literally, because it just

32:35

grew out of me throwing two

32:37

quotes from the same author up

32:39

on Twitter. And so, you know,

32:42

after the fact, people started asking,

32:44

like, well, did you plan it

32:46

that way? And the honest to

32:48

God truth is, no, I did

32:51

not. Organically grew out of it.

32:53

Hey, if you do something, my

32:55

experience has been. Tacking into what

32:57

works? Yeah. and you know it's

33:00

not quite direct mail no where

33:02

hey we're getting a response from

33:04

this but not that it's not

33:06

exactly an AB test but hey

33:09

people seem to like this let's

33:11

give them more yeah and and

33:13

that's what happened here you know

33:15

like one of the best growth

33:18

factors in investing is momentum and

33:20

if you see something gaining moment

33:22

this is this is a really

33:24

important idea for me I always

33:27

listen to the market Because if

33:29

I have one opinion and the

33:31

market has a different opinion, I'm

33:33

wrong. Probably. Most of the time.

33:36

And so momentum in this regard

33:38

you see all the DM's increasing.

33:40

Hey, when are you going to

33:42

do the book for this? Hey,

33:45

where's the newsletter, etc. And I'm

33:47

like, okay, this is truly emerging

33:49

from beneath, not from me saying,

33:52

you know what, I'm going to

33:54

do a two quotes book and

33:56

it's going to be great. No,

33:58

this was all others in the

34:01

marketplace saying to me, hey Jim,

34:03

do a two thoughts book. grassroots,

34:05

groundswell. So let's talk about knowing

34:07

that you've had all these quotes

34:10

over the decades, how did you

34:12

begin to think about organizing this?

34:14

Just quotes. We, we, this Bartlett's

34:16

book of quotations and that's alphabetical.

34:19

Yeah. And you know, that's a

34:21

research piece, but you're putting this

34:23

out as less of an encyclopedia

34:25

and more of a nonfiction. How

34:28

did you think about how you

34:30

wanted to structure it and organize?

34:32

We went back and forth on

34:34

that forever, and then we decided,

34:37

okay, let's, let's separate it by.

34:39

broad groupings like thinkers, writers, authors,

34:41

you know, dynamos, people who founded

34:43

companies and were incredibly successful. And

34:46

we in the hard cover of

34:48

the book, we made sure that

34:50

each one was color coded. Because

34:53

really the book is not meant

34:55

for you to sit down and

34:57

read all the quotes. It's really

34:59

meant to have on your coffee

35:02

table, have on your desk, and

35:04

just open it up randomly, it's

35:06

what I do, and just read

35:08

the two quotes, because you'll see

35:11

two quotes on each page, and

35:13

kind of think about them. And

35:15

because people are, and by the

35:17

way, that's the way. everyone I've

35:20

ever talked to as a copy

35:22

of the book, that's the way

35:24

they're using it. And so it

35:26

was the kind of the, you

35:29

know, a lot of people do

35:31

morning pages, do that kind of

35:33

thing in the morning they write.

35:35

And the number of people who've

35:38

either emailed me, texted me or

35:40

DM me on Twitter saying, I

35:42

absolutely love this for my morning

35:44

writing, right? Because they'll open it

35:47

randomly, right? They'll contemplate the quote,

35:49

they'll write it at the top

35:51

of their morning writing, and then

35:54

that's what they talk about. It

35:56

inspires them. So based on that,

35:58

let me suggest... We need a

36:00

two quoted day desktop calendar where,

36:02

you know, like, do you remember those

36:05

old ones? Where you just pull, you

36:07

know, just, it was almost like a

36:09

giant pad of posted notes. Mine was

36:12

a far side calendar. I was about

36:14

to say that. I still have the,

36:16

in my head, this. school for the

36:19

gifted where he's pushing on the and

36:21

the door says pull like from that

36:23

exact same exactly I had one of

36:26

those and I had a Calvin and

36:28

Hobbs and it's like a different one

36:30

every day another one of my

36:33

favorites absolutely that's so funny

36:35

so let's talk about what are real

36:37

quotes and and what are not and

36:39

I have a very vivid recollection of

36:41

putting a quote that supposedly was

36:44

Thomas Jefferson in bailout nation

36:46

and like a year after

36:48

the book was published I

36:50

got an email from someone saying

36:53

they like the book the

36:55

book p.s. This is an

36:57

urban legend. Thomas Jefferson never

36:59

said this. and that's how

37:01

I ended up eventually tracking

37:03

down quote investigator because I

37:05

was so horrified and one person

37:07

said something nobody ever mentioned

37:10

it again yeah and it was like

37:12

all right so the good news is the

37:14

bad news is what a screw up the

37:16

good news is nobody noticed how

37:18

did you go about the

37:20

process of validating and verifying

37:22

that the quotes were real

37:24

and genuine. It's not just

37:26

Mark Twain, it's Albert Einstein

37:28

and George Carlin, apparently said

37:30

all these things they never

37:32

said. Compounding is the eighth.

37:34

Wonder of the world. Einstein

37:37

never said that. Yeah, no,

37:39

I know. So there I

37:41

was very lucky to have

37:43

a very diligent team and

37:45

they identified a host of

37:47

sources. We used quote investigator,

37:49

but we used others as

37:51

well to try to get

37:53

the veracity of the author

37:55

and the quote right. Now,

37:57

having said that, I'm sure.

37:59

that there are still some examples

38:02

in there where we got it

38:04

wrong. Right. And so we even

38:07

put a little thing in there

38:09

saying, you know, all errors. Yeah,

38:11

all errors are our own, right?

38:14

But philosophically, I have a little

38:16

bit of a different view of

38:18

this. I think that we all

38:21

too often, because we we anthropomorphize

38:23

things to the extent where if

38:26

Albert Einstein said this, then

38:28

it's important. I invert that, I

38:30

invert that, and I say, it

38:32

doesn't matter who said this, let's

38:35

stay with the compounding is the

38:37

eighth wonder of the world. You

38:39

know what? You and I know

38:41

that's true. It actually is true.

38:44

We know that's true. And so

38:46

what's more important, that idea getting

38:48

into somebody's head, or that Barry

38:51

Riddholtz or Jim O'Shahness actually said

38:53

that. To me... It doesn't really

38:55

matter. Now I'm not trying to

38:58

diss the people who want to

39:00

be exact. They should be. You

39:02

want to be accurate. Absolutely correct.

39:05

But with me, it's always more

39:07

like I'm... fascinated by the thought or

39:09

the message that's being communicated. That's what

39:11

I want people to focus on. Now

39:13

obviously we want it to be attributed

39:15

to the right person. You know Banksy

39:18

had a really funny quote. I don't

39:20

think we put it in the book

39:22

but I put it up on Twitter

39:24

a lot and it's... any kind of

39:26

philosophical statement sounds better if you

39:28

put the name of a dead

39:30

famous philosopher after it and he

39:33

put Plato and then and then

39:35

waved beneath it he wrote no

39:37

Banksy and so I thought that

39:39

was really funny but you know

39:41

that's probably what's actually

39:44

happening right it's like hmm I

39:46

want people to really take this

39:48

seriously so I'm gonna make sure

39:50

that Einstein said this so that

39:52

you know it doesn't add to

39:55

what the what the thought is

39:57

inspiring in you you

39:59

know that kind of reminds me

40:01

of the Abe Lincoln line,

40:03

don't believe everything you read

40:05

on the internet, right? But

40:07

let me, let me in

40:09

the question, in your research

40:11

process, did you find a quote

40:14

that you knew and loved and

40:16

thought, oh, this is great

40:18

and it fits this person

40:20

so well, and then subsequently

40:22

you discover. Oh, it wasn't

40:24

by that person. Yes. Any

40:26

come to mind? Well, we had

40:28

quite a few, actually, Eleanor Roosevelt

40:31

quotes that were not Eleanor

40:33

Roosevelt. Really? And we had

40:35

a lot of, well, not

40:37

going back over the obvious

40:39

ones, Einstein, you know, Twain,

40:41

George Carlin, Oscar Wilde, Oscar Wilde,

40:43

etc. And if we love the

40:46

quote, we would put it

40:48

in under the actual author's

40:50

name. And I can't think

40:52

of one that's great right

40:54

now, where we did that.

40:56

But it's really funny too, because

40:58

the reaction, we did this, we

41:01

did a test on our

41:03

company Slack. I put the

41:05

same quote when we found

41:07

one of these. And it

41:09

was originally attributed to Eleanor

41:11

Roosevelt. And it actually ended up

41:13

being a woman who was

41:15

a friend of hers and

41:17

often in the White House,

41:19

but who no one had

41:21

ever heard of, at least

41:23

no contemporary person had ever heard

41:25

of. So I put them both

41:28

up on our company Slack

41:30

and I said, what do

41:32

you guys think of the

41:34

first one? Lots of emogies

41:36

and everything. And then I

41:38

put it up with the other

41:40

woman's name. The less famous, actual

41:43

author. Crickets and so to

41:45

me there's obviously something being

41:47

activated in our brain That

41:49

says ooh must be important

41:51

because Eleanor Roosevelt or Albert

41:53

Einstein said it and I always

41:55

try myself To be neutral on

41:58

that I always try to

42:00

focus on what is being

42:02

said, not who is saying

42:04

it. And to give you

42:06

the behavioral finance spin on

42:08

that, that's the halo effect. You're

42:10

giving credit. to a person for

42:12

success in one area and

42:14

you're allowing that to spill

42:16

over to the quote whether

42:18

or not they said it

42:20

or not. It's not quite

42:22

social proof, but hey, if it's

42:25

Oscar Wild or Mark Twain, we

42:27

know they were wordsmiths and

42:29

brilliant and hey, if they

42:31

said it, it must be

42:33

good. Right. Or and I

42:35

wonder if that's why people

42:37

attribute thing to George Carlin and

42:40

to say nothing of Einstein. wrote

42:42

this book tell us a

42:44

little bit about your co-author

42:46

Vatsal Kowshik how did you

42:48

guys handle the the workload

42:50

did you was he more

42:52

organizational and you more philosophical I

42:55

know you're deep down inside a

42:57

philosopher tell us how did

42:59

you go about putting the

43:01

work together so Vatsal was

43:03

the first employee of infinite

43:05

loops my podcast and he

43:07

is an amazing guy He is

43:09

multi-talented. He's a great builder

43:11

of tech, but he also

43:13

reads extensively. And it was

43:15

actually Vassal who came to

43:17

me and said, okay, Jim,

43:20

you got all these guys and

43:22

women texting you saying we want

43:24

a book. He goes, let's

43:26

do the book. And so

43:28

what he handled was almost

43:30

exclusively the vetting. the process

43:32

of making sure who I

43:34

had attributed the quote to was

43:37

correct. But then he also did

43:39

a bit of curating, you

43:41

know, he decided with ultimately

43:43

my approval, you know, we

43:45

don't think this group really

43:47

goes in there, we'd much

43:49

prefer this group. So he was

43:52

very instrumental on the actual curation

43:54

of the quotes, where I

43:56

was, as you say, much

43:58

more philosophical. If there was

44:00

one that I absolutely loved

44:02

and he just wasn't finding

44:04

a place to fit it in,

44:06

then I would say, well, try

44:09

harder. All right. So I

44:11

know there are certain authors

44:13

you really appreciate, but I'm

44:15

curious. What thinkers what philosophers

44:17

what books? Found their way

44:19

into the Gestalt of this book

44:21

what what really influenced your approach

44:24

to this so It was

44:26

not necessarily, because hint, there'll

44:28

probably be another version of

44:30

this book coming out. Could

44:32

be 10 more versions of

44:34

this book, right? So some I

44:36

held in abeyance because I really

44:39

wanted them to go into

44:41

the second book, but... You

44:43

know, I admire greatly all

44:45

of the Age of Enlightenment

44:47

authors and thinkers. You know,

44:49

your Adam Smiths, your, you know,

44:51

all the people who were like,

44:53

way to tick, we could

44:55

actually do things that we

44:57

might call the scientific method

45:00

and really test all of

45:02

our beliefs, much to this

45:04

grin of the ruling churches of

45:06

the time period. And so

45:08

Voltaire, always big, big fan

45:10

of his work. And you

45:12

know, but I didn't go

45:14

at it from that. vantage

45:16

point. What I really wanted to

45:18

do because of the nature of

45:21

the book, in other words

45:23

I never expected anyone to

45:25

sit and go from the

45:27

front page to the last

45:29

page. If I had, I

45:31

would have done it differently. Then

45:33

I would have tried to tell

45:36

a story, an overall story,

45:38

with the quotes, something we

45:40

might actually try with... the

45:42

one of the next versions

45:44

of the book. But with

45:46

this one, since I knew I

45:48

wanted it to be kind of

45:51

a jumping off point for

45:53

people to get an idea

45:55

to think about it, I

45:57

just was very much not,

45:59

you know, I'm not gonna

46:01

make it obvious and I'm not

46:03

gonna follow them in sequential order

46:05

or, you know, this group

46:07

all are together and absent

46:09

from other places in the

46:11

book. So. Yeah, I mean

46:13

like you'll get a very

46:15

good idea for some of my

46:18

favorite thinkers by just looking at

46:20

who I'm doing quotes by

46:22

Why a book? Why not

46:24

some other media? You're so

46:26

you know digital forward and

46:28

have been for a long

46:30

time I always find I like

46:33

physical books but you know you

46:35

and I are from a

46:37

earlier generation everything seems to

46:39

be moving in a different

46:41

direction. It is but number

46:43

one like if you look

46:45

at Ojana Sea Ventures it's everything

46:48

that I love like infinite books

46:50

the publisher infinite film I

46:52

love movies the fellowships which

46:54

you know all about but

46:56

I think that it's not

46:58

just people of our generation

47:00

who like beautiful books. In fact,

47:02

the people who were the

47:04

most excited about it were

47:06

younger people. Because we took

47:08

a great deal of care

47:10

to make it beautiful. And

47:12

we had the printer from Italy

47:15

do the printing and it's got

47:17

color and the spine isn't

47:19

glued. So the number of

47:21

younger people, and when I

47:23

say younger, anyone probably under

47:25

35, the notes that I

47:27

would get saying this is the

47:30

most beautiful artifact. And I heard

47:32

that term more than once,

47:34

artifact, artifact. So there, so

47:36

one was a friend. And

47:38

so I called him and

47:40

I'm like, why are you

47:42

calling this an artifact? And he

47:45

goes because I'm beginning to look

47:47

at these hard cover books

47:49

as works of art, right?

47:51

And so that was surprising

47:53

to me, but I love

47:55

books, you know, I have

47:57

big libraries at my house. I

47:59

mostly, by the way, Barry, read

48:02

on Kindle for iPad, right?

48:04

If I love a book,

48:06

I always buy the hard

48:08

copy. And if I really

48:10

love a book, I buy

48:12

the hard copy from my library

48:14

and three paperbacks to give to

48:17

friends. And so one of

48:19

the things, it's kind of

48:21

like vinyl, right? We grew

48:23

up on vinyl, that's how

48:25

we made our mixed tapes,

48:27

everything else, but guess what? A

48:29

lot of young people are going

48:32

back and sampling vinyl. So

48:34

everyone seems to like it.

48:36

There's a certain tactile feel.

48:38

I used to love the

48:40

album art, which not only

48:42

do you not get with the

48:44

same way with small CDs, but

48:46

when you move to streaming,

48:48

you don't even know the

48:50

names of half the songs

48:52

on an album because it

48:54

just all kind of comes

48:56

through. It's a different experience. Yeah,

48:59

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Please visit mumu.com for full

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disclosures. So let's talk a

51:29

little bit about both O'Shaughnessy

51:31

Ventures and O'SAM. I sort

51:33

of look at them as

51:35

part of a continuum on your

51:38

on your career. You let your

51:40

son Patrick take over as

51:42

CEO of O'Shawnessy Asset Management.

51:44

He was a key driver

51:46

of canvas, which was built

51:48

on top of a database

51:50

that you've been refining since the

51:52

1990s. Do I have that? Yeah,

51:55

yeah, and actually, you might

51:57

remember I started. the first

51:59

online investment advisor called NetFolio.

52:01

That's right. In 1999, 2000,

52:03

I was just, you know,

52:05

23 years too early. And I

52:07

also made the mistake of making

52:10

it B to C, whereas

52:12

that was a huge mistake.

52:14

Should have gone B to

52:16

B because I later learned.

52:18

You know, I was a

52:20

level playing field guy and like

52:22

people can just buy their no

52:24

loads and everything. But the

52:27

more the data presented itself

52:29

to me, the more I

52:31

came over to the side

52:33

where advisors are earning every

52:35

dollar you pay them because the

52:37

results, the outcomes were just so

52:39

much better. So. we started

52:41

building the tools that became

52:43

canvas during the great financial

52:45

crisis. I'm like, okay, we're

52:47

probably not going to sell

52:49

another long only US stock portfolio

52:52

for the next three years. So

52:54

let's really attack the data.

52:56

Let's clean it, by the

52:58

way, really hate it by

53:00

my research team for that

53:02

entire period, because it's really

53:04

mind numbingly bad. But by the

53:07

way, Now, that's a great

53:09

use case for AI. It

53:11

can do it much faster.

53:13

It can do it, you

53:15

know, you can free your

53:17

staff to not have to do

53:19

that laborious, my numbingly dull type

53:22

of work so that they

53:24

can work on better research,

53:26

more interesting topics. But yeah,

53:28

and as we were doing

53:30

it, and Patrick walked into

53:32

my office and he's like, you

53:34

know, dad. We, he actually did

53:36

say this to me, I

53:38

know it became lore, but

53:40

he goes, we built the

53:42

death star to kill a

53:44

mouse here. And I'm like,

53:46

what do you mean? He goes,

53:49

well, our clients, the Rittold's wealth

53:51

management of the world, could

53:53

use this and it would

53:55

be amazing. for their business.

53:57

Now obviously, because I had

53:59

already tried with NetFolio, I

54:01

was like, let's do it. So

54:04

yeah, building out the actual technology

54:06

though, that was a multi-year

54:08

effort. It took us a

54:10

long time. You know, our

54:12

mutual friend Dave Nautig has

54:14

been a supporter of direct

54:16

indexing. and ETFs obviously for a

54:19

long time and my complaints were

54:21

always yeah but it's cludgy

54:23

yeah but I get these

54:25

200 page you know quarterly

54:27

appointments and it's not very

54:29

fine tunable and and I'll

54:31

never forget when Battenac came back

54:33

to the office having seen a

54:36

demo uh... he if he

54:38

had hair it would have

54:40

been on fire like that's

54:42

what it was that's what

54:44

it was like he was

54:46

jumping up and down and just

54:48

the demo is like oh wow

54:51

this is we wanted to

54:53

have the absolute best software

54:55

for the way we managed

54:57

money and there was really

54:59

nothing off the shelf that

55:01

suited our needs and so we

55:03

put on a pretty significant developer

55:06

team that had background in

55:08

portfolio management. This is key.

55:10

The problem with just a

55:12

technologist trying to come into

55:14

our industry and build a

55:16

platform like this, they don't know.

55:18

all of the junk that

55:20

goes on underneath. We do

55:22

because that's what we do,

55:24

right? They don't think about,

55:26

well, who's the clearance agent,

55:28

who's the custodian, all of those

55:30

types of things. So by actually

55:33

having people very, very... with

55:35

very deep domain knowledge and

55:37

asset management, the way it

55:39

really works, that was a

55:41

huge help in us building

55:43

out the software. But the original

55:45

thing Barry was we wanted to

55:48

serve you our clients better

55:50

and faster. And then when

55:52

we saw. that the customization

55:54

that the tax management that

55:56

all of that would be

55:58

really appealing to not only our

56:00

advisors but to our advisors clients

56:03

that's when it clicked. Wow

56:05

like kind of our AWS

56:07

moment was huh. We think

56:09

other people might really like

56:11

this too. No, absolutely. The

56:13

tax side of it was a

56:15

game changer. And when I was

56:17

doing some recent research for

56:19

another project, I just started

56:21

going through the list of

56:23

trillion-dollar asset managers that either

56:25

bought or built a direct

56:27

indexer. And when you see 10

56:30

or 20 of the largest farms

56:32

in the world... or moving

56:34

in the same direction, hey,

56:36

pay attention. Something's going on.

56:38

Customization is the future. We

56:40

are leaving one-size-fits-all. And the

56:42

ability to customize your client's portfolio

56:45

down to their specific needs is

56:47

really, it really is a

56:49

game changer, especially on the

56:51

like tax alpha that you

56:53

can generate. So you mentioned

56:55

your AI earlier. I know

56:57

you've been appointed chairman of the

57:00

board at stability AI Up to

57:02

I was so that's no

57:04

longer so let me rephrase

57:06

that question So you mentioned

57:08

AI earlier. How do you

57:10

see AI transforming either the

57:12

investment management industry or venture capital?

57:14

What is the role of

57:16

AI going to be going

57:18

forward? I truly believe that

57:20

AI is the most powerful

57:23

technology that has ever come

57:25

on the scene during my career.

57:27

Wow. And it is going to

57:29

be used primarily for replacing

57:31

arduous boring mine numbing type

57:33

activities that humans are currently

57:35

doing the AI can do.

57:37

Let me give you an

57:39

example. If you work with a

57:42

legacy publisher, you're done with your

57:44

manuscript, you send it and

57:46

you probably have this experience.

57:48

Typos, typos, typos, typos, typos,

57:50

but it didn't get back

57:52

to you probably for a

57:54

couple of months. With infinite books,

57:57

it'll probably get back to you

57:59

the next day. Because we

58:01

have an AI that takes

58:03

all of those typos, fixes

58:05

them. prints it in galley

58:07

format because non-authors might not

58:09

believe this but an author when

58:12

they see their work in the

58:14

way it's gonna look as

58:16

a book it kind of

58:18

freaks you out you start

58:20

reading it differently very much

58:22

so and so we'll have

58:24

that that will go back to

58:26

the author all the typos will

58:29

be gone and any incongruity

58:31

in the manuscript will be

58:33

noted we won't touch it

58:35

because we want to leave

58:37

it to the author to

58:39

make whatever changes they want But

58:41

if it says, hey Barry, in

58:44

chapter one, you said this,

58:46

but in chapter four, you

58:48

said the exact opposite thing,

58:50

which one do you want?

58:52

And then finally, we have

58:54

plagiarism routines, where a million little

58:56

pieces, where you have to go

58:58

on and get scolded by

59:00

Oprah, well, should never happen

59:03

again. Because sometimes people. aren't

59:05

plagiarizing intentionally. They are maybe

59:07

doing it from memory, something

59:09

they read, etc. And wouldn't it

59:11

be far better for everyone

59:13

concerned if you just bring

59:15

that to the author's attention

59:17

and they can fix it?

59:19

So you have a lot

59:21

of interest. So it's not just

59:23

venture investing, it's aye, it's publishing,

59:26

it's fellowships where you find

59:28

somebody who you sponsor for

59:30

a year and... you know,

59:32

sort of a MacArthur genius

59:34

grant. Where can you go?

59:36

What can you do with this?

59:38

You know, where do you really

59:41

focus your time and effort?

59:43

What most interests you? So

59:45

I'm going to cop out

59:47

and give you the answer.

59:49

All of it interests me,

59:51

Barry, or I wouldn't have it.

59:53

True. But I'm very lucky in

59:56

that we have a senior

59:58

person at the head of

1:00:00

each one of these verticals.

1:00:02

And so I let them,

1:00:04

I'm very big on hiring

1:00:06

people with super high agency and

1:00:08

who are really, really bright, mostly

1:00:10

brighter than me. And I

1:00:12

let them run with what

1:00:14

they want to do. always

1:00:16

keep me informed as to

1:00:18

hey we might be trying

1:00:20

this big change and then I

1:00:23

sign off there but I mean

1:00:25

basically the verticals were all

1:00:27

areas that I loved I

1:00:29

love movies I love books

1:00:31

I love media I love

1:00:33

podcasts etc etc. And they

1:00:35

were also areas where I felt

1:00:38

that there was a lot of

1:00:40

arbitrage opportunity available. For instance,

1:00:42

like most legacy publishers are

1:00:44

operating under best principles. but

1:00:46

they're operating under the best

1:00:48

principles from 1925, not 2025.

1:00:50

And so there is so much

1:00:53

that can be improved in the

1:00:55

process to make the author

1:00:57

a good deal happier, to

1:00:59

make the reading public have

1:01:01

access to their authors work

1:01:03

sooner than they might otherwise,

1:01:05

but also because of the... technology,

1:01:07

we are able to offer

1:01:09

a much better deal to

1:01:11

our authors. Our authors typically

1:01:13

will take 70% of the

1:01:15

royalties after the costs have

1:01:17

been cleared. So we can still

1:01:20

make a great deal of money

1:01:22

at the 30% that we

1:01:24

maintain. But there's also cross-pollinization,

1:01:26

right? There's a great podcaster

1:01:28

who is gonna be a

1:01:30

great author. There is a

1:01:32

great author who might be a

1:01:35

great podcaster, or we'll do the

1:01:37

whole. thing for them. We'll

1:01:39

set them up on a

1:01:41

sub stack. We'll give them

1:01:43

a podcast. We'll publish their

1:01:45

book. What we really want

1:01:47

to focus on is ideas that

1:01:50

ended up in slush piles in

1:01:52

days of year. A lot

1:01:54

of great writing is there.

1:01:56

And so we want to

1:01:58

be able to not only

1:02:00

see that, but publish the

1:02:02

best of it. So you're publishing

1:02:04

books. You're hosting your own podcast,

1:02:07

Infinite Loops. I'm kind of

1:02:09

intrigued by the idea of

1:02:11

investing in movies, which tend

1:02:13

to be a black hole

1:02:15

of losses. You know, it's

1:02:17

like restaurants, plays, and films. Tell

1:02:19

us what you're doing cinematically. So

1:02:22

cinematically, we started, our little

1:02:24

mantra is crawl walk run.

1:02:26

And so, you know, it

1:02:28

was odd for me because,

1:02:30

you know, I had a

1:02:32

very established reputation in asset management.

1:02:34

And here I'm the total underdog.

1:02:37

I mean, like, we are

1:02:39

the Rebel Alliance, if you

1:02:41

will, going up against some

1:02:43

very, very tough competitors. So

1:02:45

on the film side, we

1:02:47

started with documentaries. One of our

1:02:49

first flip side actually premiered at

1:02:51

the Toronto Film Festival. Amazing

1:02:53

reviews got bought out by

1:02:55

a distributor And so that

1:02:57

went very very well. We

1:02:59

are now commissioning documentaries with

1:03:01

some younger talent that isn't really

1:03:04

bound up by the way Hollywood

1:03:06

currently does things and Meaning

1:03:08

a little more nimble like

1:03:10

much much more nimble much

1:03:12

faster much more responsive much

1:03:14

faster much more responsive much

1:03:16

faster much more responsive much faster

1:03:19

much more responsive sort of

1:03:21

as a little bit of

1:03:23

a publicity stunt, I want

1:03:25

to say eight or ten

1:03:27

years ago, but that's really

1:03:29

very feasible today, isn't it? Oh,

1:03:31

absolutely. And when you add in

1:03:34

all of the things that

1:03:36

AI, I mentioned all of

1:03:38

the laborious stuff that you

1:03:40

get rid of with publishing,

1:03:42

same is true in film.

1:03:44

So this is going to sound

1:03:46

weird, but you know what eats

1:03:48

up like huge amounts of

1:03:50

time and is ridiculously boring.

1:03:52

Color matching. Really? When things

1:03:54

are filmed over a variety

1:03:56

of days or locations or

1:03:59

what have you, one day is

1:04:01

cloudy, one day sunny, you've got

1:04:03

to have that match up

1:04:05

so that your film appears

1:04:07

of a piece. So it's

1:04:09

more than just continuity. Absolutely.

1:04:11

It's the next step beyond

1:04:13

that. And... There's just so much

1:04:16

that can be done with the

1:04:18

visual part, with the editing

1:04:20

AIs that we have, always

1:04:22

gonna have a human editor,

1:04:24

but we are giving them

1:04:26

tools that just makes them.

1:04:28

able to do their job in

1:04:31

a much more creative way because

1:04:33

they don't have to take

1:04:35

that hour or two hour

1:04:37

and do the niggly, I've

1:04:39

got to move this to

1:04:41

here and that to there.

1:04:43

They literally can press a button

1:04:45

and it happens. So what we're

1:04:48

finding is a great amount

1:04:50

of the workflows in these

1:04:52

industries are time consuming, boring,

1:04:54

and just like they take

1:04:56

forever. And we can fix

1:04:58

that to the point where they

1:05:00

no longer take forever and the

1:05:03

people we're working with absolutely

1:05:05

love it because they can

1:05:07

spend their time making that

1:05:09

edit like supreme, right? We're

1:05:11

giving them back time that

1:05:13

they can use artistically. So so

1:05:15

many people have been pessimistic

1:05:17

about AI. It's gonna kill

1:05:19

jobs, it's gonna damage society,

1:05:21

you won't know what to...

1:05:23

to do, to believe, to

1:05:25

trust, we'll all be out of

1:05:28

work. I don't get the sense

1:05:30

that you're looking at AI

1:05:32

that way. You seem to

1:05:34

think that this, or it

1:05:36

sounds like you're finding, this

1:05:38

is just an incredibly useful

1:05:40

tool, and it's gonna make all

1:05:43

of us more productive and more

1:05:45

creative. Precisely. You know, we

1:05:47

always get frightened when some

1:05:49

new technology comes on the

1:05:51

scene, and by the way,

1:05:53

this goes back forever forever,

1:05:55

and who broke up all the

1:05:57

machines because they were gonna take

1:06:00

their jobs while he ended

1:06:02

up working on one of

1:06:04

those looms and he vastly

1:06:06

preferred his new job because

1:06:08

he didn't have to do

1:06:10

it the old horrible way same

1:06:12

thing's gonna happen here but it

1:06:15

happens all the time right

1:06:17

so when records first came

1:06:19

out you know that symphony

1:06:21

orchestras took full page ads

1:06:23

in newspapers saying that isn't

1:06:25

real music is live you have

1:06:27

to hear it live or you're

1:06:30

listening to a counterfeit. Right?

1:06:32

So when this type of

1:06:34

advance comes along, you always

1:06:36

axiomatically people get freaked out.

1:06:38

I think, you know, AI

1:06:40

is not going to take your

1:06:42

job. A human being using the

1:06:44

AI tools will. because they

1:06:46

are going to be so

1:06:48

much more proficient at what

1:06:50

they're doing. They're going to

1:06:52

have so much more time

1:06:54

to focus on the really high

1:06:57

value stuff and not have to

1:06:59

worry with all the stuff

1:07:01

that, you know, they had

1:07:03

to do in the past,

1:07:05

but now we can automate

1:07:07

it through AI workflows. So

1:07:09

I subscribe to what they call

1:07:12

the Senator model. You remember

1:07:14

the mythical bees, half horse,

1:07:16

half horse, half man. That's

1:07:18

what is... going to happen

1:07:20

with AI. It's going to

1:07:22

be AI plus human being. That's

1:07:24

where all the great stuff is

1:07:27

going to come. Right now?

1:07:29

We're gonna see a tsunami

1:07:31

of slop that's gonna be

1:07:33

just AI generated and people

1:07:35

will think, oh, that's good

1:07:37

enough, right? And so going forward,

1:07:39

you can create a huge edge

1:07:41

by having good taste and

1:07:43

curating it well. But I

1:07:45

can guarantee you almost all

1:07:47

of that is going to

1:07:49

be human using AI as

1:07:51

a tool to make their jobs.

1:07:54

better, easier, more creative. The way

1:07:56

I look at it is,

1:07:58

you know, Steve Jobs famously

1:08:00

said computers were bicycles for

1:08:02

your mind. AI is a

1:08:04

rocket ship for your mind.

1:08:06

I like the way you phrase

1:08:09

that. You know, someone once asked

1:08:11

me, you know, what's the

1:08:13

secret to putting out the

1:08:15

daily reads? And my answer

1:08:17

was, curate viciously. Exactly. And

1:08:19

you know, AI, I don't

1:08:21

think in our lifetime and probably

1:08:24

not our kid's lifetime is going

1:08:26

to reach the point where

1:08:28

it can be a tastemaker.

1:08:30

We believe, passionately believe, that

1:08:32

if you have good taste

1:08:34

and you are a great

1:08:36

curator, your future looks incredible. Really?

1:08:38

Because you'll be able to use

1:08:41

these tools. You won't have

1:08:43

to spend all the time

1:08:45

that you used to. And

1:08:47

that's going to even make

1:08:49

it. It's going to be

1:08:51

the rocket chip. to give you,

1:08:53

get you to the next level

1:08:56

of your good taste and

1:08:58

curation. So a couple more

1:09:00

questions before we get to

1:09:02

our final question, and that

1:09:04

is first I have to

1:09:06

ask you about the O'Shaughnesse Fellowship,

1:09:08

what I've been calling your MacArthur

1:09:11

Award. Tell us a little

1:09:13

bit about the support you

1:09:15

offer for young entrepreneurs, what

1:09:17

inspired you to start this

1:09:19

program. I know we've had

1:09:21

at least one O'Shaughness. fellowship person

1:09:23

Kyle Scanlon as a guest

1:09:25

on the show. Maybe one

1:09:27

other, I'll have to go

1:09:29

through the list and see

1:09:31

what motivated you to create.

1:09:33

this program and how has it

1:09:35

been running? So it's running really,

1:09:38

really well. We have the

1:09:40

applications. We're now in our

1:09:42

third year. The applications are

1:09:44

much more numerous and the

1:09:46

quality of the applicant. I

1:09:48

mean, Barry. Literally if I could

1:09:50

I would give most of them

1:09:53

fellowships. Right. But the real

1:09:55

reason that I did it

1:09:57

was because I had become

1:09:59

convinced that geography time and

1:10:01

space have all collapsed. And

1:10:03

in the old days, you know,

1:10:05

you and I would know each

1:10:08

other still because we both

1:10:10

live here in New York

1:10:12

and we both are in

1:10:14

the same business. But other

1:10:16

than that, like... Prior to

1:10:18

the internet, prior to what I

1:10:20

call the human colossus, we couldn't

1:10:22

find those geniuses elsewhere. We

1:10:24

can now. And I believe

1:10:26

that it is absolutely imperative

1:10:28

to show the world that

1:10:30

there are a ton of

1:10:32

brilliant people in this world, many

1:10:35

of them young. who don't have

1:10:37

an opportunity to demonstrate what

1:10:39

they have to offer to

1:10:41

the world. Now we can

1:10:43

find and more importantly fund

1:10:45

them. And the way we

1:10:47

do it is it's totally no

1:10:50

strings funding. So if you're a

1:10:52

fellow you get $100,000 over

1:10:54

a one-year period to work

1:10:56

on your project. If you're

1:10:58

a grantee you get 10,000.

1:11:00

We have obviously many more

1:11:02

grantees than we have fellows. just

1:11:05

the blossoming of the way the

1:11:07

groups work together. Like I

1:11:09

thought that it would take

1:11:11

us at least five years

1:11:13

to build like a really

1:11:15

cool network of super smart

1:11:17

switched on people. It's already happened.

1:11:19

We have we have we

1:11:21

have in-person meetings once a

1:11:23

year and the last one

1:11:26

we had, I'll just give

1:11:28

you a quick example. We

1:11:30

have a scientist who is developing

1:11:32

an in-home way to test your

1:11:34

baby's poop to make sure

1:11:36

that it's okay. She had

1:11:38

no idea how to market

1:11:40

this. Another fellow was sitting

1:11:42

right next to her, he's

1:11:44

a writer, he's a thinker, and

1:11:47

he knows all about this, and

1:11:49

literally, over the course of

1:11:51

an hour and a half,

1:11:53

he gave her a completely

1:11:55

different marketing plan that she

1:11:57

adored. She came over to

1:11:59

me and she said... I can't

1:12:02

believe that in an hour and

1:12:04

a half, he totally changed

1:12:06

the way I'm going to

1:12:08

bring this to market. So

1:12:10

the cross-pollinization and the synthesis

1:12:12

of these great minds is

1:12:14

really a thing to behold. I'm

1:12:17

just very, very excited about what's

1:12:19

coming out. And before we

1:12:21

get to our favorite questions,

1:12:23

I want to throw you

1:12:25

a curveball. Curveball. So since

1:12:27

we first met back in

1:12:29

a... CMC Green Room in the

1:12:31

early 2000s. So a few decades

1:12:34

ago, you've had a fairly

1:12:36

unique perch on the world

1:12:38

of finance and investing and

1:12:40

asset management. How has financial

1:12:42

media and asset management changed

1:12:44

over the course of your career?

1:12:46

Well... At the beginning of my

1:12:49

career, kind of squawk box

1:12:51

on CNBC was the gold

1:12:53

standard. And the format they

1:12:55

used at that time. I

1:12:57

used to co-host with Markanes

1:12:59

all the time. Sure. I've done

1:13:01

that a few times. Back then,

1:13:03

it was a three-hour program.

1:13:06

in which the portfolio manager

1:13:08

or the strategist that we

1:13:10

were talking to was given

1:13:12

like 20 minutes. I recall

1:13:14

to actually articulate their thesis about

1:13:16

why they were bullish or

1:13:18

bearish, why they liked this

1:13:20

particular group or that particular

1:13:22

group. So one of the

1:13:24

things that I saw happening

1:13:26

when that changed was... We were

1:13:28

not giving the audience like that

1:13:31

kind of Treatment which is

1:13:33

really really incredible treatment It

1:13:35

was a three-hour period that

1:13:37

gave you enough time to

1:13:39

actually talk things out Now

1:13:41

what's happened? Podcast like yours clearly

1:13:43

have come along and you've replaced

1:13:46

that aspect And so, you

1:13:48

know, I would bemoan when

1:13:50

I saw that happening with

1:13:52

Squok, especially, oh, I would

1:13:54

really wish that they could

1:13:56

return to the old format, but

1:13:58

then you and many, many other,

1:14:01

my son with advice like

1:14:03

the best, came in and

1:14:05

filled the void. So I

1:14:07

think what investors are able

1:14:09

to get access to now.

1:14:11

Is just it dwarfs are the

1:14:13

early days when you and I

1:14:15

met in that green room?

1:14:17

They have so many podcasts.

1:14:19

They can choose from they

1:14:21

can they can still watch

1:14:23

financial media Then there's the

1:14:25

YouTube people right? But like everything

1:14:28

you've got to aggressively curate Somebody

1:14:30

like you you know you're

1:14:32

way up here and you're

1:14:34

kind of the gold standard,

1:14:36

but it how many shows

1:14:38

have you done you you

1:14:40

have? Proof of work. I'll tell

1:14:43

you a funny story. So where

1:14:45

July will be 11 years,

1:14:47

it's 550 shows. The origin

1:14:49

story, I don't know if

1:14:51

I ever told this on

1:14:53

my own podcast. I'm pretty

1:14:55

sure I've told it elsewhere. It's

1:14:58

coming back from a conference in

1:15:00

Vancouver, Canada. And I had

1:15:02

to either change planes in

1:15:04

Chicago or Montreal. I don't

1:15:06

remember coming back to New

1:15:08

York. and I'm in the

1:15:10

lounge and I want to say

1:15:12

it was CNBC and they

1:15:14

were interviewing Bill Ackman. I

1:15:16

could be wrong. Maybe it

1:15:18

was Einhorn, I don't remember,

1:15:20

but it was a fun

1:15:22

manager like that who back then

1:15:25

was not, there's no Twitter, they

1:15:27

weren't doing a lot of

1:15:29

TV. you really don't go

1:15:31

on TV unless you were

1:15:33

marketing or had a really

1:15:35

good quarter and I just

1:15:37

remember hearing the worst like it

1:15:40

was a five-minute hit not a

1:15:42

20-minute hit that's right and

1:15:44

when you have five minutes

1:15:46

it's What's your favorite stocks?

1:15:48

When the Fed's gonna cut?

1:15:50

Where's the Dow gonna be

1:15:52

next year? Thanks for coming by.

1:15:55

And the moment that guy walks

1:15:57

out of the building, those

1:15:59

answers are stale. And so

1:16:01

I was flying back after

1:16:03

you changed planes, I bumped

1:16:05

into a friend, and I

1:16:07

was kind of like grinding in

1:16:09

my teeth. And he's like, what's

1:16:12

on your mind? You look

1:16:14

like you're annoyed. And I

1:16:16

relate the story. And he

1:16:18

said, what questions would you

1:16:20

ask? And the questions we're

1:16:22

about to ask, I'm about to

1:16:24

ask. What's your favorite stocks? When

1:16:27

the Fed's going to cut?

1:16:29

Where's the Dow going to

1:16:31

be next year? Thanks for

1:16:33

coming by. And the moment

1:16:35

that guy walks out of

1:16:37

the building, those answers are stale.

1:16:39

And so I was flying back

1:16:42

after you changed planes, I

1:16:44

bumped into a friend, and

1:16:46

I was kind of like

1:16:48

grinding in my teeth. And

1:16:50

he's like, what's on your

1:16:52

mind? You look like you're annoyed.

1:16:54

And I relate this story. And

1:16:56

he said, what questions would

1:16:58

you ask? And the questions

1:17:00

we're about to ask, I'm

1:17:02

about to ask you, those

1:17:04

were some of the questions.

1:17:06

Who are you? How did you

1:17:09

get that way? What are you

1:17:11

reading? Who are your mentors?

1:17:13

How did you develop your

1:17:15

philosophy? If you were giving

1:17:17

me advice as a college

1:17:19

grad, what would you tell

1:17:21

me if I wanted to go?

1:17:24

Like, just off the top

1:17:26

of my head? Sure. Just

1:17:28

because I wanted the person

1:17:30

to have... to use the

1:17:32

word you used earlier. Agency

1:17:34

and control over the story, but

1:17:36

also express what they've learned over

1:17:39

the decades. Exactly. And 30

1:17:41

seconds doesn't give you that.

1:17:43

So on that note, let's

1:17:45

jump to our speed rounds

1:17:47

and do our favorite questions

1:17:49

that we ask all of our

1:17:51

guests. I think this is probably

1:17:53

the third or fourth time.

1:17:55

I've had you do these.

1:17:57

I hope I don't give

1:17:59

the same answers. Hey listen,

1:18:02

you'll have AI go through

1:18:04

it and find out how your

1:18:06

how your thinking has evolved. Let's

1:18:08

describe that. There we go,

1:18:10

I love that. Right? So

1:18:12

starting with what's keeping you

1:18:14

entertained these days, what are

1:18:16

you watching or listening to?

1:18:18

a challenge in that it sucks

1:18:21

up time that you can't listen

1:18:23

to others or you don't

1:18:25

want to listen to somebody

1:18:27

in an interview and you

1:18:29

don't want someone else's questions

1:18:31

in your head. So my

1:18:33

dirty little secret is that I

1:18:36

very very seldomly listen to my

1:18:38

own. I do read the

1:18:40

transcripts just to make sure

1:18:42

I really screwed that up

1:18:44

I got to fix that

1:18:46

transcripts don't come across the

1:18:48

same way I know I know

1:18:51

I know but I prefer to

1:18:53

give my active listing time

1:18:55

to like your podcast and

1:18:57

Patrick's in terms of reading

1:18:59

I continue to read very

1:19:01

very broadly my favorite sort

1:19:03

of literary fiction author is David

1:19:05

Mitchell who wrote cloud Atlas oh

1:19:08

really and I've started reading

1:19:10

to a movie. Yeah, yeah.

1:19:12

the books much better than

1:19:14

the movie. So one else

1:19:16

said that, yeah. And I

1:19:18

love Howard Bloom's work, you know,

1:19:20

the, he's- Closing of the

1:19:22

American Minds? No, no, different

1:19:24

guy, sounds like, right? Howard

1:19:26

is a very fun, eccentric

1:19:28

genius, who sort of started

1:19:30

life as a scientist and now

1:19:33

takes all of what he learned

1:19:35

there and applies it to

1:19:37

the social world or the

1:19:39

business world. Closing of the

1:19:41

American mind? would be the

1:19:43

Lucifer principle about how all

1:19:45

of our evolutionary things that are

1:19:48

driving a lot of our actions

1:19:50

have profound implications for markets.

1:19:52

for societies for all of

1:19:54

these things and like he's

1:19:56

got a great book gaming

1:19:58

reimagining the beast where he

1:20:00

talks about capitalism saying hey capitalism

1:20:02

is hands down the winner but

1:20:05

we can still improve it

1:20:07

and we should improve it

1:20:09

and here's how I think

1:20:11

we should so love his

1:20:13

work Read pretty much any

1:20:15

paper I can get my hands

1:20:17

on having to do with advances

1:20:20

in. AI and that sort

1:20:22

of thing. For fun, I

1:20:24

just saw the new Bob

1:20:26

Dylan movie, loved it. A

1:20:28

complete unknown. And I also

1:20:30

loved the way Timothy Shalomé, the

1:20:32

lead in that. I loved his

1:20:35

speech when he got up

1:20:37

and said, you know what?

1:20:39

I could say, ah, shucks

1:20:41

and I'm nothing, but I

1:20:43

want to tell you something.

1:20:45

I am aspiring to greatnessness. I

1:20:47

want. to be great. And I

1:20:49

love actually seeing the younger

1:20:51

generations start saying things like

1:20:53

that because it's so for

1:20:55

so often, you know, we,

1:20:57

you know, oh, wasn't really

1:20:59

anything. come on false humility false

1:21:02

humility just like it stands out

1:21:04

yeah doesn't it right jars

1:21:06

when you hear it it's

1:21:08

like when I heard him

1:21:10

give that speech I'm like

1:21:12

right on that's where I

1:21:14

love hearing from a young actor

1:21:17

or writer or whatever I

1:21:19

hey I aspire to this

1:21:21

don't we all aspire to

1:21:23

greatness or at least so

1:21:25

right we should like you

1:21:27

get one bite of the apple,

1:21:29

you know, one run. Make it

1:21:32

make it worth something. Make

1:21:34

it worthwhile. Yeah. And so

1:21:36

I was very happy to

1:21:38

see that again. Just for

1:21:40

total fun. I love Billy

1:21:42

Bob Thornton, so we really enjoyed

1:21:44

Landman. You know, you're like the

1:21:46

third or fourth person who

1:21:48

told me how much they

1:21:50

love that. It is so

1:21:52

much. It's just fun. And

1:21:54

so you're probably. I'm not

1:21:56

going to learn a lot by

1:21:59

watching it, other than that Billy

1:22:01

Bob Thornton chews up every

1:22:03

scene that he appears in.

1:22:05

He's such a good actor.

1:22:07

Always is, every time I

1:22:09

see him. Me too. Me

1:22:11

too. He's a delight. You know,

1:22:14

you have such an interesting

1:22:16

background. I'm curious if you

1:22:18

had any mentors help shape

1:22:21

your career. I did. I

1:22:23

had a gentleman who was,

1:22:25

when I was very, very

1:22:27

young. I'm not going to

1:22:30

mention his name because some

1:22:32

of his kids might be

1:22:34

listening, but we'll go with

1:22:36

Jim. He was also a

1:22:38

Jim. And he probably did

1:22:41

more for me when I

1:22:43

was young and filled with

1:22:45

vinegar and very definitive beliefs and

1:22:47

I will tell you all I'm

1:22:49

gonna proselytize this is the way

1:22:52

to do it and he was

1:22:54

really really good at saying uh

1:22:56

Jim you might want to take

1:22:58

that a step back because what

1:23:00

do you really want I want

1:23:02

people to know about this okay

1:23:04

But what's the broader implication here?

1:23:07

Process over outcome. Okay, well why

1:23:09

don't you talk a little bit more

1:23:11

about that? Why don't you talk

1:23:13

about the way that people can

1:23:16

actually take what you're saying to

1:23:18

them and make them useful in

1:23:20

their own life? So he was

1:23:22

an amazing mentor to me because

1:23:25

he was very patient, wicked sense

1:23:27

of humor and always good at

1:23:29

reminding me that. You might want to

1:23:32

take it back a notch or

1:23:34

two. That's great. Let's, you mention

1:23:36

a few books, any other favorites

1:23:38

you want to mention before we

1:23:40

get to our favorite questions? The,

1:23:43

the, what, let me reference our

1:23:45

infinite books. We have a list

1:23:47

that you can get anywhere. It's,

1:23:49

you can go to Twitter, you

1:23:51

can go to our sub stack,

1:23:54

and it's kind of our seminal

1:23:56

books, you know, books like The

1:23:58

Beginning of Infinity. I think is

1:24:01

a masterpiece. Beginning of Infinity

1:24:03

by David Deutsch, who's a

1:24:05

quantum physicist in the UK.

1:24:07

I love all of his

1:24:10

work, but I also think

1:24:12

people should be reading things

1:24:14

like my perennially read the

1:24:16

Tao de Jing. by Lau.

1:24:19

It packs a wallop, man,

1:24:21

because you can read the

1:24:23

whole thing in an hour.

1:24:26

But I used to joke,

1:24:28

you know, I started reading

1:24:30

that when I was 18

1:24:32

and I read it every

1:24:35

year, sometimes multiple times every

1:24:37

year, and I finally started

1:24:39

to understand it when I

1:24:42

was about 55. I was

1:24:44

going to say it's a

1:24:46

different book each time you

1:24:48

read it. It really is.

1:24:51

It's like Heracles. You know,

1:24:53

no man steps in the

1:24:55

same river. Our final two

1:24:57

questions that we ask all

1:25:00

of our guests, what sort

1:25:02

of advice would you give

1:25:04

to a recent college grad

1:25:07

interested in a career in

1:25:09

either investing, quantitative analytics, or

1:25:11

venture capital? Understand. the leverage

1:25:13

that you get from all

1:25:16

of the new AI tools.

1:25:18

It gives you several advantages.

1:25:20

The older people on those

1:25:23

desks might not be rapidly

1:25:25

adopting using those tools. And

1:25:27

if you walk into a

1:25:29

job interview with some mastery

1:25:32

of them, what they're doing

1:25:34

in terms of what they

1:25:36

can uncover for like VC,

1:25:38

for traditional long only or

1:25:41

long short management, is staggering.

1:25:43

Get a deep domain knowledge

1:25:45

there as it fits into

1:25:48

your particular passion, be it

1:25:50

investing or. analysis, etc. But

1:25:52

that would be my number

1:25:54

one piece of advice. Wow.

1:25:57

And our final question, what

1:25:59

do you know about the

1:26:01

world of investing today that

1:26:04

would have been helpful back

1:26:06

in the 1990s when you

1:26:08

were first starting out. People

1:26:10

don't change. Markets change. And

1:26:13

when I really, really came

1:26:15

to understand that was after

1:26:17

actually the great financial crisis.

1:26:19

I went through the crash

1:26:22

in 1987. I went through

1:26:24

the other bear markets, but

1:26:26

I didn't really lock in.

1:26:29

on the fact that markets

1:26:31

change millisecond by millisecond, human

1:26:33

behavior barely budges millennia by

1:26:35

millennia, arbitraging human nature is

1:26:38

the final mode. That's fantastic

1:26:40

place to end it. Jim,

1:26:42

thank you so much for

1:26:45

being so generous with your

1:26:47

time and for being just

1:26:49

such a great... colleague, mentor,

1:26:51

source of wisdom, like it's

1:26:54

been my privilege to know

1:26:56

you my whole career. I

1:26:58

remember, I want to say

1:27:00

it was like the late

1:27:03

2000s sitting at an outdoor

1:27:05

in Starbucks. Yeah, I remember

1:27:07

it well. I remember it

1:27:10

well. Don't we know each

1:27:12

other? It was just like

1:27:14

one of those small world

1:27:16

moments and you've always been

1:27:19

just so thoughtful, so inspiring,

1:27:21

so inspiring. and your insights

1:27:23

just I know you so

1:27:26

many people you've had such

1:27:28

a positive impact on it

1:27:30

it's just a delight and

1:27:32

a pleasure to know you

1:27:35

well right back atchberry I

1:27:37

it's been my great pleasure

1:27:39

knowing you all of these

1:27:42

years so so this mutual

1:27:44

admiration society has to come

1:27:46

to an end it's a

1:27:48

bromance we have been speaking

1:27:51

with Jim Oshonasy founder in

1:27:53

CEO of oceanacy ventures if

1:27:55

you enjoy this conversation? Well,

1:27:57

check out any of the

1:28:00

500 previous ones we've had

1:28:02

over the past 10, almost

1:28:04

11 years. You can find

1:28:07

those at iTunes, Spotify, YouTube,

1:28:09

Bloomberg, or wherever you find

1:28:11

your favorite podcast. Be sure

1:28:13

and check out my new

1:28:16

book, How Not to Invest,

1:28:18

the bad ideas, numbers, and

1:28:20

behaviors that destroy wealth. Coming

1:28:23

wherever you get your favorite

1:28:25

books on March 18th 2025,

1:28:27

I would be remiss if

1:28:29

I did not thank the

1:28:32

crack team that helps with

1:28:34

these conversations. Together Anna Luke

1:28:36

is my producer Meredith Frank

1:28:38

is my audio engineer. Sage

1:28:41

Bauman is the head of

1:28:43

podcast at Bloomberg. Sean Russo

1:28:45

is my researcher. I'm Barry

1:28:48

Rittoltz. You've been listening to

1:28:50

Masters in business on Bloomberg

1:28:52

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