A Timeless Collection of Infinite Wisdom with Jim O'Shaughnessy

Barry speaks with Jim O'Shaughnessy, Founder and CEO of O'Shaughnessy Ventures LLC. Prior to founding O'Shaughnessy Ventures, Jim was the Founder and Chair of OSAM (O'Shaughnessy Asset Management) which was acquired by Franklin Templeton in 2021. He also served as Senior Managing Director and Executive Director of Systematic Equity for Bear Stearns. His book "What Works on Wall Street" was a New York Times bestseller. On this episode, Barry and Jim discuss his path through the world of business, the power of well-chosen words, and his new book "Two Thoughts: A Timeless Collection of Infinite Wisdom."

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Episode Transcript

Speaker 1 (00:02):
Bloomberg Audio Studios, Podcasts, radio news. This is Masters in
Business with Barry Ritholts on Bloomberg Radio.

Speaker 2 (00:16):
This week on the podcast What a delight extra special
guest Jim O'Shaughnessy. His book that I came to know
him with first was What Works on Wall Street, which
has been just a perennial seller. I think it's in
its fourth or its sixth edition and really influenced several

(00:38):
generations of quants. On finance, O'Shaughnessey Asset Management became a
leader indirect indexing eventually was bought by Franklin Templeton, leading
him to launch O'Shaughnessy Ventures, O'Shaughnessy Fellowships, Infinite Loops podcast,
just so many different things. New book is delightfully titled

(01:02):
Two Thoughts, a timeless collection of infinite wisdom, and reflects
many of the insights and just thoughtfulness that Jim shows
in everything he does. I always find it delightful to
have him on the show, and you can tell how
much I appreciate him just by the conversation meanders wherever

(01:26):
it goes, and I occasionally look at my list of questions,
but really I just want to see where Jim's mind
is going to take it and come along for the ride.
I thought this was delightful and I think you will
also with no further ado my conversation with Jim O'Shaughnessy Barry.

Speaker 3 (01:43):
I am always looking forward to these conversations. That's great
to be back.

Speaker 2 (01:48):
It's a pleasure for me. Also, you and I.

Speaker 3 (01:50):
Go way back, way way back.

Speaker 2 (01:52):
And it's kind of funny, Like twenty five years later,
I was like, oh, how do you know Jim. Oh,
we met in the green room of TV, you know,
right after the dot com crash. It was kind of
it was kind of funny. But let's talk a little
bit about all the different businesses and ventures that you're
you're involved with. So I knew you right around the

(02:15):
time you were getting ready to depart bear Sterns. You
at bear Stearns for like.

Speaker 3 (02:21):
A decade or so, no, about five and a half years.

Speaker 2 (02:24):
Okay, so the in the mid two thousands, and you
had the great insight and business acumen to tap out
of bear Sterns in two thousand and seven with all
of those options that you had and exercise the option
sell them and launch your showing. Essy asset management. So

(02:47):
you went on the way out, you went on the
way into starting the new firm. Tell us a little
bit about the early days leaving bear Stearns and setting
up OSAM.

Speaker 3 (02:58):
So first, let me correct everyone assumes that I saw
the Great financial crisis coming and therefore wanted to spin
out of bear Stearns. Yeah, what do they say if
the story conflicts with the legend, print the legend. The
legend really isn't correct. Though, we had begun conversations with

(03:23):
bear Stearns folks months and months before the financial crisis
came on the scene, and it was essentially a very
amicable parting. As you note, when we spun out, we
kept all of our bear Stearns accounts, continued to work
with all their private client service people over there, So

(03:44):
it was very very amicable. But of course, because the
Great financial crisis came along and bear had those CDO
funds that had a little bit of a problem. Was
it was just irresistible for Newspece people to say. I
had one reporter sit with me for an hour and
a half and all she kept doing was, come on,

(04:06):
tell me the truth, tell me the truth, tell me
the truth.

Speaker 2 (04:09):
You know, It's funny because when we look at certain
books that get the timing of things right or completely wrong.
People forget a book just doesn't appear wholesale out of
thin cloth. It's the idea has to come along, and
then then you got to get a publisher that wants
and unless you're gonna self publish, then you got to
write it so that it's like a one or two

(04:30):
year lag. I would imagine pulling out a substantial division
from a major brokerage firm doesn't happen overnight. It's going
to be like a six or twelve month.

Speaker 3 (04:42):
Process, absolutely, because you have to have everyone with the
oars going in the same direction. You want to make
sure that it is agreeable and everyone is whether they're
unhappy that you're going, they're happy with the deal that allowed.

Speaker 2 (05:00):
You to go.

Speaker 3 (05:01):
And so I took extra time to make sure that
that happened because I loved the folks over at Bear
and it was really just my own desire to be
an entrepreneur again, and they really got that and so
very amicable. But as you know, those things take a
long time to get negotiated out.

Speaker 2 (05:21):
Yeah, you know, to me, the thing I'm I was
always kind of sad about with the fall of Bear
Stones eventually picked up for pennies by Jamie Diamond and
JP Morgan Chase and then even Lehman brothers. I know
a lot of great people in a lot of different divisions.
You know, we all have mentors all over the street
that even if they're a counterparty or if they're a salesperson,

(05:46):
there were things to learn from folks. And Bear and
Lehman were two like giant storied names. And I mean,
obviously there was a massive disruption throughout society, but the
tragedy that a lot of lay people don't know are
really good people doing really good work get they're the

(06:08):
collateral damage from someone else's screw up.

Speaker 3 (06:11):
Totally agree, and the you know, obviously just my personal opinion,
but I think at that particular point in time, all
of the investment banks were bankrupt or insolvent.

Speaker 2 (06:24):
And well some were a little more insolvent than others.

Speaker 3 (06:27):
Yeah, I agree, I agree, And so it was almost
a bit like luck of the draw that Lehman and
Bear were the ones to go.

Speaker 2 (06:36):
Down there went down early enough that would be salvageable.
And then a little known story that a lot of
people are unaware of. When I was writing Bail Out
Nation and doing my homework, it turned out that JP
Morgan Chase had a little derivatives flare up like years earlier.

(06:56):
And I don't remember if it was Jamie Diamond or
one of his lieutenanenans, but someone said, hey, this is
a mess, and this is really potentially damaging. And it
might have been Diamond who said, sell it all. I
don't care the price, if you have to take a
ten or twenty percent haircut. I want all this, well
of the books. And that's what they did. And so
when the world went to hell, they were They picked

(07:19):
up Washington Mutual, they picked up Bear Sterns. They got
to cherry pick the best of the best at pennies
on the dollar. And that's why JP Morgan is the
monster success it is today.

Speaker 3 (07:30):
Well, Jamie is a super smart guy, and that does
not surprise me at all. You know, the joke around
Bear Stearns at the time was that Jamie really the
real reason he wanted to buy Bear.

Speaker 2 (07:43):
Was he wanted the building right right, which is now
overshadowed by their brand new headquarter no park. But that
was a great octagonical building which we could see out
from our farm's windows on Brian Park with the glass.

Speaker 3 (07:59):
It was a beautiful.

Speaker 2 (08:00):
And and you walk in and it's like, you know,
they used to be Wall Street and then there was
you know, the Morgan, Stanley and Lehman brothers sort of
off of Midtown. Yeah where, and then this was just
all right, so very prescient before Vanderbilt was even a thing.

(08:21):
That's right, And there they are now when Vanderbilt is
a monster. So so let's bring it back to to
what you're doing. So you leave there you launch. Oh, Sam,
you've already had great success with what works on Wall Street?
What made you think? I think we're gonna develop a
series of quantitative approaches to managing money?

Speaker 3 (08:45):
Wow? Uh so that was a dinner when I was
a teenager. My grandfather had been very successful. He was
an oil speculator, uh huh, and he kind of beat
the pledge guys by about seven years. He proceeded to
give away the vast portion of his fortune during his

(09:06):
own lifetime.

Speaker 2 (09:07):
What was it really a fortune?

Speaker 3 (09:09):
It really was, no kidd. And what he couldn't give
away he put into a foundation, the Iao'shaughnessy Foundation, which
I think today is still about one hundred million dollar foundation,
No kidd, but he made his five kids the trustees,
and so once a quarter there would be a dinner

(09:31):
and it would rotate. I was brought up at Saint Paul,
and so during the Saint Paul rotation, I got lucky
enough at I think I was sixteen to get invited
to the adult table. And of course, like i'd want
it to be an adult, I loved going to my parents'
cocktail parties and talking to adults, and so I was
really excited. And literally I was put down next to

(09:55):
my uncle John and my dad, and I'm listening and
they're talking about IBM, but they're just talking about the CEO.
They're not talking about how.

Speaker 2 (10:05):
Much do they make?

Speaker 3 (10:06):
How much do you have to pay for every dollar
of earnings or sales or evida? And I kind of
raised my hand and said, Dad, Uncle John, don't you
think it might be a better idea to look at
it by the numbers? And they dismissed me. This is
nineteen seventy six, right, So I got yeah, exactly, well exactly,

(10:28):
and so I decided, you know what, I'm going to
go look into this. So I took myself down to
the James J. Hill Research Library in downtown Saint Paul,
and I thought I was going to be really ambitious,
but I am potentially the world's laziest man. So when
I saw the five hundred of the S and P,
the S and P tear sheet book, I'm like, oh,

(10:51):
I'm not gonna be able to do that. So I
alighted on the Dow thirty sucks right? Did the research
found very compelling evidence that what it's pe is really
matters to your returns going forward. Very very high valuations
tended to crash and burn, Very very cheap valuations tended

(11:12):
to do well. But of course, you know Barry, I
was sixteen seventeen, much more interested in girls, and so
after college, got married young, I was like, I've got
to revisit all this, and got the data set from
Compu's stat and essentially that became what works on Wall Street.

Speaker 2 (11:34):
So wait, would you study in college?

Speaker 3 (11:37):
So the reason I am an economics I have a
degree in economics. The reason for that was I had
maybe six more credits, four to six more credits in
economics than I had in history. So history absolutely well, listen,

(11:58):
I think a good knowledge of history is absolutely vital
if you want to be a good investor, right yeah.
I mean, like one of the Roman wits said, he
who does not understand what happened before they were born
remains forever a child, And essentially I didn't want to

(12:19):
remain a child. If you look back at the market's history,
guess what. History doesn't repeat itself.

Speaker 2 (12:26):
But it rhymes.

Speaker 3 (12:27):
I mean, you go back to Isaac Newton losing a
fortune in the south Sea bubble, and like, literally I
always do this joke because people get it. It's like
people were so in love with that stock. Poets wrote
poetry about it. One went fill the south Sea goblet
ful the God's shill of our stocks. Take care europea

(12:50):
please accepts the bull, but Jove with joy puts off
the bear. And I used to when I was still
at OSAM, I used to say, I'm totally a quant
but if if somebody writes a poem about a stock
you owned.

Speaker 2 (13:02):
That's a high. That's amazing, and it's funny. You and
I both have a love of quotations. And the I
tried repeatedly to track down the source of history doesn't repeat,
but it rhymes. It's always attributed to Mark Twain or
someone else, and I've never been able to really verify that.

Speaker 3 (13:25):
Yeah, quote investigator.

Speaker 2 (13:27):
I love that site.

Speaker 3 (13:28):
Yeah, it's pretty good. They can normally get you to
the original sighting of the text. What's funny about that, though,
is almost inevitably it's somebody you've absolutely never heard of.
That's right, And I think that's why people like when
that sounds like something Mark Twain would say.

Speaker 2 (13:46):
Right.

Speaker 3 (13:47):
But then there's also the Mark Twain Oscar wild I
mean there's a bunch of them. Like any quote that
you really love and you don't know who did it,
people tend to say Mark Twain Oscar.

Speaker 2 (14:00):
The one from Twain that stands out is and I'm
gonna mangle this. It's not the things we know that
get us into trouble. It's the things we know for
sure that just ain't show.

Speaker 3 (14:10):
Yeah. That was actually a character of Mark Twain's, Oh really,
And he spoke like a Southerner of the late a
nineteen hundreds, and I think his last name was Ward.
The character's last name was Ward Twain. I mean, he

(14:31):
has some of the great actual quotes that are really his.
What I love is like if you pick up a
dog in the street that is starving and feed it.
It will love you. If you do the same for
a human, it will bite you. This is the principal
difference between a dog and a man, which A.

Speaker 2 (14:52):
Is true and B leads to the newer line, if
you want a friend on Wall Street, get a dog. Yeah,
it's really true. We're going to talk more about quotes
and books in a moment. Before we do that, I
just want to bring up the first book, What Works
on Wall Street. That book not only has been through

(15:13):
multiple editions, it's had legs, It's influenced an entire generation
or two of quants. What was the most surprising thing
about what you found in the book and then its
subsequent reception in finance?

Speaker 3 (15:31):
So, I think the most surprising thing was a number
of people at various firms that I was investigating working
for before starting my own I mean, I had my
own company, but I was getting a lot of offers,
primarily because they knew the book was coming right many
of them when they saw the galleys of the book,

(15:54):
the manuscript, the first thing they said to me, Bary
was we would love to hire you, but you cannot
publish this view you're giving it away, right exactly, going
to go there exactly. And I was like, no, no, no, no, no,
you you can have the greatest truth in the world.
You can scream it from all the rooftops, you can

(16:15):
take full page ads in the Wall Street Journal. Most
people are just gonna go, eh, they're not gonna do it.

Speaker 2 (16:22):
It's so true. You know. My takeaway from my first book,
which is now fifteen years ago, was there would be
these debates about what led to the crisis, what were
the factors? What were And I'm like, no, no, We've
solved that. I've addressed that. Let's let's move beyond that.

(16:42):
And the arguments didn't stop. People just kept on debating it.
And my takeaway was, oh, you could just drop a
truth bomb on people's laps and if they don't want
to believe it, they're not gonna believe it. And that
was like, maybe I was naive, but you're one hundred
percent right. The fact that they thought you were giving
the secret away you could here's a secret to investing.

(17:06):
Not maybe you'll do okay with it, but nobody's going
to really adapt.

Speaker 3 (17:12):
Well, you know what's funny is I would say to
these people It was one of the like when I
started out, and actually What Works wasn't my first book,
invest Like the best was, which showed you really how
to clone your favorite money managers right by looking at
the biggest difference between their portfolio factor distribution and then
using those as screens to get a portfolio much like

(17:33):
your manager. Note we used to update the clones versus
the manager. Last time we did it was years and
years ago. But the thing that I found really interesting
was all of the clones were beating the managers that
they cloned.

Speaker 2 (17:48):
Was that case of the fee or was that cos
they're not great sellers?

Speaker 3 (17:52):
It was because of our very human emotional decision makings.
Almost always under extreme stress, models don't get stressed, you know,
they don't get hungover, They never fight with their spouse.
They just keep applying those criteria. You're in, you're out.
And I think that the you know, we went through

(18:15):
some tough times after that book came out, and and
people have different ways of dealing with stress, and one
of them is not being good at selling.

Speaker 2 (18:24):
So there's been a number of studies and I don't
want to talk about my book, We're going to talk
about your book, But some really fascinating things you learn
are when you look at the academic research fund manager.
Fund managers are actually surprisingly good buyers, yes, but they're
terrible sellers. And part of the reason is the emotionality

(18:46):
of the sale. They tend to panic out when they shouldn't,
or through the opposite, hold on right to the bitter
end when they.

Speaker 3 (18:54):
Really should well. And also it's just because it's just
part of our human os, part of our human operator system.
I remember when Enron was going through difficulties and I
was set to speak with a classic manager, right, a
fundamental guy, and we were going to share the stage.
And the first question went to me and it was like,

(19:16):
are you do you own Enron? And my answer was no,
the numbers are pretty bad and so we don't. And
he looked at me kind of you know, with the
chuckle ugh you quants, you know, and then he launched
into this description of not only did he hold, he

(19:38):
bought more and then he gave this as the explanation.
I went to a barbecue at the cfo's house. The
CEO was there, the CFO, and I looked them in
the eye and I said, is there trouble? And they
assured me there wasn't and I'm just kind of like

(19:59):
sitting over there with Oh, okay, just don't touch this one.

Speaker 2 (20:03):
Maybe we could get a short put on this that
just like I'll tell you something, it's really funny. And
this just goes to how naive and stupid I am,
or especially was early in my career. I would listen
in on quarterly calls, and I would believe every word
I heard, like, these guys aren't going to lie to

(20:25):
their investors. Everything's gonna be great. And I very quickly learned, oh,
you're a terrible judge of people. You'll buy anything that
a slick salesman is selling you. You just have to stop.
And I just stopped listening to calls because I'm an idiot.
I believe what they say. I would rather look at

(20:45):
the numbers and yeah, I know the numbers can lie,
but not as easily as you know that.

Speaker 3 (20:51):
That's also a really big part of human os default
to trust.

Speaker 2 (20:56):
Well, we're social.

Speaker 3 (20:59):
Right, right, were domesticated primates. We grew up in groups
where trust was really really important. So your average human
defaults to trust. And by the way, that's not a
bad default for the vast majority of people. It probably
works better to trust who you're listening to, right, And

(21:20):
so one of the things that we're looking at in
one of our divisions at O'Shaughnessy Adventures right now is
voice software AI that does stress analysis on any type
of media. So obviously earning calls present themselves as kind
of number one. Yeah really and I got to tell you,

(21:42):
Barry Wow.

Speaker 2 (21:44):
Exciting way stuff.

Speaker 3 (21:45):
Oh my god.

Speaker 2 (21:46):
Now how much of that is nervousness about speaking to
a large audience and nervousness because they know something and
they don't want to disclose it.

Speaker 3 (21:54):
So, as you might guess, you do baselines. You take
a recording where clearly either you know, you get some
tape that was before the call or you know, a
speech that had nothing to do with earnings, and that
creates your baseline, and then you get to see very

(22:15):
very quickly, like Spike, we don't have any worries.

Speaker 2 (22:21):
Spike, Wow, that sounds like fun.

Speaker 3 (22:24):
Yeah, it is fun, And we're not sure how we're
gonna do it because we don't offer asset management services
to people outside of O'shaughna's Adventures. That was a deal
that we made with Franklin Templeton that we would not launch, but.

Speaker 2 (22:38):
You could still do a little Come on, don't don't
you get the itch sometimes to say, hey, x y
Z stock is wildly overvalued and the CFO is full
of it. Let's put on some let's buy some deep
out of the money puts. We'd see where this goes.

Speaker 3 (22:54):
You know, if you can keep a secret, we might
try that with some of our internal capital.

Speaker 2 (23:00):
Let me know, I'm right there with you. I love
the idea of that. Where did the title come from?

Speaker 3 (23:06):
So it came from a group of my teammates at OSV.
Essentially I have been a quote junkie all of my life.
Same so I have kept I Barry have notebooks filled
with oh really, from way back when I I think
the first time I started it, I was twenty one.

(23:28):
And so I just love them and I think that
you know, they can pack a lot of a punch
if you if you put them together right, if you
curate them right, et cetera. If you read what Works
on Wall Street, I open every chapter with it.

Speaker 2 (23:42):
I do that a lot. Also, I writ it's fun.
Let me let me ask you one other question about
the title. So one of the things that's fascinating if
you're if you like music or poetry or even I'm
gonna go into the weed Shakespearean iamic pentameter. Okay, so

(24:05):
there is a rhythm too, and I'm gonna write this
down so you know, even if if you get this,
I want you to know there is a rhythm to
the phrase A timeless collection of infinite wisdom. That reminds
me of another book title. And I'm curious if it

(24:25):
was in your mind when you came out with this.

Speaker 3 (24:28):
Oh you got me on that one.

Speaker 2 (24:30):
A heartbreaking work of staggering genies, A timeless collection of
infinite wisdom. It just leaves off in that same rhythm.

Speaker 3 (24:41):
I don't know if that was a wasn't purpose behind
recause I've always loved that title.

Speaker 2 (24:50):
Heartbreaking work, stagger and and it's like you could go
with you a different It's a staggering work of heartbreaking
gene It's like you could flip it around, but this
phrase theology just left that left right out.

Speaker 3 (25:03):
I am incredibly lucky to have just extraordinarily talented teammates.
We have a lot of writers on the team, we
have a lot of editors, and you know they would
just go at it like, what about this title? What
about because we had to call it two thoughts because
this started very on a whim.

Speaker 2 (25:24):
Well, I know you have been tweeting for I don't
know ten years, not just a quote. And I was
doing that for a long time, just throwing a quote
up that I thought was relevant. Sometimes I would stagger
them out, like you can plan a tweet six months
in advance. Hey, I don't know what's going to be happening
in August, but I think this is relevant. You have

(25:46):
been doing two tweets for forever.

Speaker 3 (25:48):
Yeah, And so it was kind of like, you know
Ken Stanley's book Greatness can't be planned, This is a
perfect example of that. So I just thought, you know,
what the heck, I'm going to put up two thoughts
and I'll see if I like it, if I keep
doing it, I'll just keep doing it right. And then
all of a sudden, like the people that got attracted

(26:09):
to it were there was a lot of people, and
then I started getting dms on Twitter basically saying hey,
if you would do this in a newsletter, I would subscribe.
And then one of my colleagues was like, well, let's
do the newsletter, and in the newsletter, why don't we say, hey,
would you like a book? And that's what happened. Literally,

(26:33):
we iterated, iterated, iterated, and ended up publishing the book.

Speaker 2 (26:38):
Huh. So that's really interesting that that's the genesis of
the two thoughts. When you're picking a pair of thoughts
from the same author, are you looking for things that
compliment each other? Are you looking for their most to
most profound statements? How are you selecting A and B

(26:58):
for this author?

Speaker 3 (27:00):
Yeah, it's a little bit messy to be really honest,
because I'll usually start with the notebooks that have all
my handwritten quotes out when I copied the quote over,
and sometimes I'll think, Ooh, I found like the perfect
one quote from this author, And then I'll spend some

(27:21):
time going through the rest of their work, etc. Finding
one that would compliment it. But then sometimes some of
the best two quotes that work the best they don't
compliment each other. In other words, it's kind of like, hey,
you know history rhymes, But then the second quote is

(27:43):
but always keep your eyes on the horizon, right, Like.

Speaker 2 (27:47):
Hmmm, two very different, two very different things.

Speaker 3 (27:51):
And so I wasn't precious about it at all, literally,
because it just grew out of me thrown. Two quotes
from the same author are up on Twitter, and so
you know, after the fact, people start asking like, well,
did you plan it that way? And the honest to
God truth is no, I did not organically grew up ratically. Hey,

(28:12):
if you do something, my experience has been tacking into
what works. Yeah, and you know it's not quite direct mail,
no where. Hey, we're getting a response from this, but
not that. It's not exactly an ab test, but hey,
people seem to like this, Let's give them more. Yeah,
and that's what happened here. You know, like one of

(28:32):
the best growth factors in investing is momentum, and if
you see something gaining momentum, this is this is a
really important idea for me. I always listen to the
market because if I have one opinion and the market
has a different opinion, I'm wrong probably most of the time.

(28:53):
And so momentum in this regard. You see all the
dms increasing, Hey, when are you going to do the
book for the Hey, where's the newsletter? Etc. And I'm like, Okay,
this is truly emerging from beneath, not from me saying
you know what I'm gonna do a two quotes book
and it's gonna be great. No, this was all others

(29:15):
in the marketplace saying to me, hey, Jim, do a
two thoughts book.

Speaker 2 (29:19):
A grassroots groundswell. So let's talk about knowing that you've
had all these quotes over the decades, how did you
begin to think about organizing this? Just quotes this Bartlett's
Book of Quotations, and that's alphabetical. Yeah, and you know
that's a research piece, but you're putting this out as

(29:40):
less of an encyclopedia more of a nonfiction. How'd you
think about how you wanted to structure it and organize it.

Speaker 3 (29:47):
We went back and forth on that forever, and then
we decided, okay, let's separate it by broad groupings like thinkers, writers,
author you know, dynamos, people who founded companies and were
incredibly successful. And we in the hardcover of the book,

(30:12):
we made sure that each one was color quote coded,
because really, the book is not meant for you to
sit down and read all the quotes. It's really meant
to have on your coffee table, have on your desk
and just open it up randomly. It's what I do,
and just read the two quotes because you'll see two

(30:33):
quotes on each page and kind of think about them.
And because people are and by the way, that's the
way everyone I've ever talked to as a copy of
the book, that's the way they're using it. And so
it was the kind of the you know, a lot
of people do morning pages, do that kind of thing
in the morning they write. And the number of people

(30:57):
who've either emailed me, texted me, or dm me on
Twitter saying I absolutely love this for my morning writing,
right because they'll open it randomly, right, they'll they'll contemplate
the quote, they'll write it at the top of their
their morning writing and then that's what they talk about.

Speaker 2 (31:16):
It inspires them. So based on that, let me suggest
we need a two quota day desktop calendar where you like,
do you remember those old ones where I just pull
you know, just it was almost like a giant pad
of mine. Mine.

Speaker 3 (31:31):
Mine was a far side.

Speaker 2 (31:33):
I was about to say that I still have this
in my head, this School for the Gifted where he's
pushing on the and the door says, well like from
that exact same exactly. I had one of those, and
I had a Calvin and Hobbes and it's just a
different one every other one of my favorites. Absolutely, that's
so funny. So let's talk about what are real quotes

(31:56):
and what or not. And I have a very vivid
recollection of putting a quote that supposedly was Thomas Jefferson
in Bailout Nation, and like a year after the book
was published, I got an email from someone saying they
liked the book. Ps, this is an urban legend. Thomas

(32:17):
Jefferson never said this. And that's how I ended up
eventually tracking down Quote Investigator because I was so horrified
and one person said something nobody ever mentioned it again,
and it was like, all right, so the good news
is the bad news is what a screw up. The
good news is nobody noticed. How did you go about

(32:39):
the process of validating and verifying that the quotes were
real and genuine. It's not just Mark Twain, it's Albert
Einstein and George Carlin apparently said all these things. They
never said compounding is the eighth wonder. Einstein never said, yeah,
I know.

Speaker 3 (32:58):
So there. I was very lucky to have a very
diligent team, and they identified a host of sources. We
use Quote Investigator, but we used others as well. To
try to get the veracity of the author and the
quote right now. Having said that, I'm sure that there

(33:20):
are still some examples in there where we got it wrong,
and so we even put a little thing in there saying,
you know, yeah, all errors are our own, right. But philosophically,
I have a little bit of a different view of this.
I think that we all too often because we anthromorphize

(33:43):
things to the extent where if Albert Einstein said this,
then it's important I invert that and I say, it
doesn't matter who said this. Let's stay with the compounding
of the eighth wonder of the world. You know what,
you and I know that's true, actually is true. We
know that's true. And so what's more important that idea

(34:06):
getting into somebody's head, or that Barry Ridholts or Jim
O'Shaughnessy actually said that. To me, it doesn't really matter. Now.
I'm not trying to diss the people who want to
be exact. They should be. You want to be accurate,
absolutely correct, But with me, it's always more like I'm

(34:27):
fascinated by the thought or the message that's being communicated.
That's what I want people to focus on now, obviously,
we want it to be attributed to the right person.
You know, Banksy had a really funny quote. I don't
think we put it in the book, but I put
it up on Twitter a lot, And it's any kind
of philosophical statement sounds better if you put the name

(34:50):
of a dead famous philosopher after it. And he put
Plato and then and then waved beneath it he wrote,
no Banksy, And so I thought that was really funny.
But you know that's probably what's actually happening, right. It's like, Hm,
I want people to really take this seriously. So I'm
going to make sure that Einstein said this, so that

(35:12):
you know, it doesn't add to what the what the
thought is inspiring in you.

Speaker 2 (35:19):
You know, that kind of reminds me of the Abe
Lincoln line, don't believe everything you read on the internet. Right,
But let me let me invert the question. In your
research process, did you find a quote that you knew
and loved and thought, oh, this is great and it
fits this person so well, and then subsequently you discover oh,

(35:39):
it wasn't by that person. Yes, and any come to mind.

Speaker 3 (35:43):
Well, we had quite a few, actually, Eleanor Roosevelt quotes
that were not Eleanor Roosevelt, and we had a lot
of well, not going back over the obvious ones Einstein,
you know, TWAINN. Twayne, George Carlin, oscar Wilde, etc. And

(36:08):
if we love the quote, we would put it in
under the actual author's name. And I can't think of
one that's great right now where we did that. But
it's really funny too because the reaction we did this.
We did a test on our company slack. I put
the same quote when we found one of these and

(36:30):
it was originally attributed to Eleanor Roosevelt, and it actually
ended up being a woman who was a friend of
hers and often in the White House, but who no
one had ever heard of, at least no contemporary person
had ever heard of. So I put them both up
on our company slack and I said, what do you

(36:51):
guys think of the first one? Lots of emojis and everything,
And then I put it up with the other woman's name,
the less famous author, actual author crickets. And so to me,
there's obviously something being activated in our brain that says, ooh,

(37:11):
must be important because Eleanor Roosevelt or Albert Einstein said it,
and I always try myself to be neutral on that.
I always try to focus on what is being said,
not who is saying it.

Speaker 2 (37:26):
And to give you the behavioral finance spin on that,
that's the halo effect. You're giving credit to a person
for success in one area, and you're allowing that to
spill over to the quote, whether or not they said
it or not. It's not quite social proof, but hey,
if it's Oscar Wilde or Mark Twain, we know they

(37:48):
were wordsmith's and brilliant, and hey, if they said it,
it must be must be good, right, And I wonder
if that's why people, you know, attribute thing to George
Carlin and to say nothing of Einstein. So you co
wrote this book. Tell us a little bit about your
co author, Vatsill Kowshk. How did you guys handle the workload?

(38:12):
Did you? Was he more organizational and you're more philosophical.
I know you're deep down inside a philosopher. Tell us
how did you go about putting the work together.

Speaker 3 (38:22):
So Vatsil was the first employee of Infinite Loops, my podcast,
and he is an amazing guy. He is multi talented.
He's a great builder of tech, but he also reads extensively,
And it was actually Vasil who came to me and said, okay, Jim,

(38:46):
you got all these guys and women texting you saying
we want a book. He goes, let's do the book.
And so what he handled was almost exclusively the vetting,
the process of making sure who I had attributed the
quote to was correct. But then he also did a

(39:08):
bit of curating. You know, he decided, with ultimately my approval,
you know, we don't think this group really goes in there.
We'd much prefer this group. So he was very instrumental
on the actual curation of the quotes. Where I was,
as you say, much more philosophical. If there was one

(39:31):
that I absolutely loved and he just wasn't finding a
place to fit it in, then I would say, well
try harder.

Speaker 2 (39:39):
All right. So I know, I know there are certain
authors you really appreciate, but I'm curious what thinkers, what philosophers,
what books found their way into the gestalt of this book,
What really influenced your approach to this.

Speaker 3 (39:59):
So it was not necessarily because hint, there'll probably be
another version of this book coming out. It could be
this book, right, So some I held in abeyance because
I really wanted them to go into the second book.
But you know, I admire greatly all of the Age

(40:22):
of Enlightenment authors and thinkers. You know, you're Adam Smith's,
You're you know, all the people who were like way
to tick. We could actually do things that we might
call the scientific method and really test all of our beliefs,
much to the chagrin of the ruling churches of the

(40:44):
time period. And so Voltaire always big, big fan of
his work, and you know, but I didn't go at
it from that vantage point. What I really want I
wanted to do because of the nature of the book.
In other words, I never expected anyone to sit and

(41:06):
go from the front page to the last page. If
I had, I would have done it differently. Then I
would have tried to tell a story, an overall story
with the quotes, something we might actually try with the
one of the next versions of the book, but with
this one, since I knew I wanted it to be
kind of a jumping off point for people to get

(41:27):
an idea to think about it, I just was very
much not you know, I'm not going to make it
obvious and.

Speaker 2 (41:34):
I'm not gonna.

Speaker 3 (41:36):
Follow them in sequential order or you know, this group
all are together and absent from other places in the book.
So yeah, I mean like you'll get a very good
idea for some of my favorite thinkers by just looking
at who I'm doing quotes by.

Speaker 2 (41:56):
Why a book? Why not some other media? You're so,
you know, digital forward and have been for a long time.
I always find I like physical books. But you know
you and I are from an earlier generation. Everything seems
to be moving in a different direction.

Speaker 3 (42:14):
It is, but number one, like if you look at
Ojenasy Ventures, it's everything that I love, like infinite books,
the publisher, infinite film, I love movies, the fellowships, which
you know all about. But I think that it's not

(42:35):
just people of our generation who like beautiful books. In fact,
the people who were the most excited about it were
younger people because we took a great deal of care
to make it beautiful, and we had the printer from
Italy do the printing, and it's got color and the

(42:58):
spine isn't glued. So the number of younger people, and
when I say younger, anyone probably under thirty five. The
notes that I would get saying this is the most
beautiful artifact and I heard that term more than once
artifact artifact. So there, so one was a friend and

(43:20):
so I called him and I'm like, why are you
calling this an artifact? And he goes because I'm beginning
to look at these hardcover books as works of art, right,
and so that was surprising to me. But I love
I love books, you know, I have big libraries at

(43:40):
my house. What I mostly by the way Berry read
on Kindle for iPad rightly, But if I love a book,
I always buy the hard copy. And if I really
love a book, I buy the hard copy for my
library and three paperbacks to give to and and so

(44:02):
one of the things, it's kind of like vinyl, right,
we grew up on vinyl. That's how we made our
mixtapes everything else. But guess what, a lot of young
people are going back and sampling vinyl. So I gues
everyone seems to like it.

Speaker 2 (44:15):
There's there's a certain tactile, yeah, feel I used to
love the multi album art, which not only do you
not get with the same way with small CDs, but
when you move to streaming, you don't even know the
names of half the songs on an album because it
just all kind of comes through it's a different experience, Yeah,

(44:36):
very much so. So let's talk a little bit about
both O'shaughnessee Ventures and O SAM. I sort of look
at them as part of a continuum on your on
your career. You let your son Patrick take over as
CEO of O'Shaughnessy Asset Management. He was a key driver

(44:58):
of Canvas, which was built on top of a database
that you've been refining since the nineteen nineties. How do
I have that?

Speaker 3 (45:06):
Yeah, yeah, And actually you might remember I started the
first online investment advisor called netfolio. That's right in nineteen
ninety nine, two thousand. I was just, you know, twenty
three years too early. And I also made the mistake
of making it B to C, whereas that was a

(45:26):
huge mistake. Should have gone B to B because I
later learned, you know, I was a level playing field guy,
and like people can just buy their no loads and everything.
But the more the data presented itself to me, the
more I came over to the side where advisors are
earning every dollar you pay them because the results, the

(45:50):
outcomes were just so much better. So we started building
the tools that became Canvas. During the Great Financial Crisis,
I'm like, okay, we're probably not going to sell another
long only US stock portfolio over the next three years,
so let's really attack the data. Let's clean it. By

(46:13):
the way, really hate it by my research team for
that entire period, right because it's really.

Speaker 2 (46:18):
My numbering bad.

Speaker 3 (46:20):
But by the way, now that's a great use case
for AI. It can do it much faster. It can
do it. You know, you can free your staff to
not have to do that laborious, mind numbingly dull type
of work so that they can work on better research,
more interesting topics. But yeah, and as we were doing it,

(46:45):
and Patrick walked into my office and he's like, you know, Dad,
we he actually did say this to me. I know
it became lower, but he goes, we built the death
star to kill a mouse here. I'm like, what do
you mean. He goes, Well, our clients, the rich Holts

(47:05):
wealth managements of the world could could use this and
it would be amazing for their business. Now, obviously, because
I had already tried with metfolio, I was like, let's
do it. So yeah. Building out the actual technology though,
that was a multi year effort. It took us a

(47:26):
long time.

Speaker 2 (47:27):
But what you know, our mutual friend Dave Knadig has
been a supporter of direct indexing and ETFs obviously for
a long time, and my complaints were always, yeah, but
it's cludgy. Yeah, but I get these two hundred page,
you know, quarterly appointments and it's not very fine tunable.

(47:49):
And and I'll never forget when Batana came back to
the office having seen a demo. If he had hair,
it would have been on fire. That's what it was.
That's what it was like. He was jumping up and
down and just the demo is like, oh, wow, this
is slick, and wow, this really looks good. I can't

(48:10):
believe it's that definable. It's that user and like the
deeper you went into it, it was just every step
along the way there was a ton of stuff. What
was the vision when you originally were building this, was it, Hey,
let's pump this up and sell it, because I know
you guys never were really shopping this around. Yeah, it

(48:30):
kind of fell out of the blue.

Speaker 3 (48:31):
Yeah, No, we it was not to pup it up
and sell it at all. It was we wanted to
have the absolute best software for the way we managed money.
And there was really nothing off the shelf that suited
our needs, and so we put on a pretty significant

(48:52):
developer team that had background in portfolio management. This is
key the problem with just a technologist trying to come
into our industry and build a platform like this. They
don't know all of the junk that goes on underneath.
We do because that's what we do, right. They don't

(49:15):
think about, well, who's the clearance agent, who's the custodian,
all of those types of things. So by actually having
people very very with very deep domain knowledge in asset
management the way it really works, that was a huge
help in us building out the software. But the original
thing Barry was, we wanted to serve you our clients

(49:37):
better and faster. And then when we saw that the customization,
that the tax management, that all of that would be
really appealing to not only our advisors but to our advisors' clients,
that's when it clicked Wow, like kind of our aws
moment was huh, we think other people might really like

(50:01):
this too.

Speaker 2 (50:02):
No. Absolutely, the tax side of it was a game changer.
And when I was doing some recent research for another project,
I just started going through the list of trillion dollar
asset managers that either bought or built a direct index, sir.
And when you see ten or twenty of the largest
farms in the world or moving in the same direction, hey,

(50:25):
pay attention to something.

Speaker 3 (50:26):
Customization is the future.

Speaker 2 (50:28):
We are leaving.

Speaker 3 (50:29):
We are leaving one size fits all, and the ability
to customize your client's portfolio down to their specific needs
is really it really is a game changer, especially on
the tax alfa that you can generate.

Speaker 2 (50:48):
So you mentioned your AI earlier. I know you've been
appointed chairman of the board at Stability AI. Up to
I was, so that's no longer. So let me rephrase
that question mentioned AI earlier. How do you see AI
transforming either the investment management industry or venture capital? What

(51:08):
is the role of AI going to be going forward?

Speaker 3 (51:12):
I truly believe that AI is the most powerful technology
that has ever come on the scene during my career, wow,
and it is going to be used primarily for replacing arduous, boring,
mind numbing type activities that humans are currently doing the

(51:36):
AI can do. Let me give you an example in
our publisher. If you work with a legacy publisher, you're
done with your manuscript, you sent it and you probably
had this experience right typos, typos, typos, but it didn't
get back to you, probably for a couple of months.
With infinite books, it'll probably get back to you the

(51:58):
next day because we have an AI that takes all
of those typos, fixes them, it prints it in Galley format.
Because non authors might not believe this, but an author,
when they see their work in the way it's going
to look as a book, it kind of freaks you out.
You start reading it differently, very much so. And so

(52:21):
we'll have that that will go back to the author.
All the typos will be gone, and any incongruity in
the manuscript will be noted. We won't touch it because
we want to leave it to the author to make
whatever changes they want. But if it says, hey, Barry,
in chapter one you said this, but in chapter four

(52:41):
you said the exact opposite thing, which one do you want?
And then finally we have plagiarize of routines where you know,
a million little pieces where you have to go on
and get scolded by Oprah. Will should never happen again
because some times people aren't pleasiarizing intentionally. They are maybe

(53:05):
doing it for a memory something they read, et cetera.
And wouldn't it be far better for everyone concerned if
you just bring that to the author's attention and they
can fix it.

Speaker 2 (53:16):
So you have a lot of interest. So it's not
just venture investing, it's AI, it's publishing, it's fellowships where
you find somebody who you sponsor for a year and
you know, sort of a MacArthur genius grant. Where can
you go? What can you do with this? You know,

(53:36):
where do you really focus your time and effort? What
most interests you?

Speaker 3 (53:41):
So I'm going to cop out and give you the answer.
All of it interests me, Barrier, Okay, we have it true.
But I'm very lucky in that we have a senior
person at the head of each one of these verticals,
and so I let them. I'm very big on higher
vring people with super high agency and who are really

(54:04):
really bright, mostly brighter than me, and I let them
run with what they want to do. They always keep
me informed as to hey, we might be trying this
big change, and then I sign off there. But I mean, basically,
the verticals were all areas that I loved. I love movies,

(54:24):
I love books, I love media, I love podcasts, etc.
And they were also areas where I felt that there
was a lot of arbitrage opportunity available. For instance, like
most legacy publishers are operating under best principles, but they're
operating under the best principles from nineteen twenty five, not

(54:46):
twenty twenty five. And so there is so much that
can be improved in the process to make the author
a good deal, happier, to make the reading public have
access to their own authors work sooner than they might otherwise.
But also because of the technology, we are able to

(55:08):
offer a much better deal to our authors. Our authors
typically will take seventy percent of the royalties after the
costs have been cleared, so we can still make a
great deal of money at the thirty percent that we maintain.
But there's also cross polonization. Right, there's a great podcaster

(55:33):
who is going to be a great author. There is
a great author who might be a great podcaster or
will do the whole thing for them. We'll set them
up on a sub stack, we'll give them a podcast,
we'll publish their book. What we really want to focus
on is ideas that ended up in slush piles in

(55:54):
days of yore. A lot of great writing is there
and so we want to be able to not only
see that, but publish the best of it.

Speaker 2 (56:03):
So you're publishing books, you're hosting your own podcast, Infinite Loops.
I'm kind of intrigued by the idea of investing in movies,
which tend to be a black hole of losses. You know,
it's like restaurants, plays, and films tell us what you're

(56:24):
doing cinematically.

Speaker 3 (56:26):
So cinematically we started our little mantra is Crawl Walk Run,
and so, you know, it was odd for me because
you know, I had a very established reputation in asset management,
and here I'm the total underdog. I mean, like we
are the rebel Alliance, if you will, going up against

(56:48):
some very very tough competitors. So on the film side,
we started with documentaries. Uh huh. One of our first
Flip Side, actually premiered at the Toronto Film Festival, got
amazing reviews, got bought out by a distributor, and so
that went very very well. We are now commissioning documentaries

(57:12):
with some younger talent that isn't really bound up by
the way Hollywood currently does things.

Speaker 2 (57:19):
And get a little more nimble, like.

Speaker 3 (57:23):
Much more nimble, much faster, much more responsive.

Speaker 2 (57:27):
Someone had shot a film on an iPhone sort of
is a little bit of a publicity stunt, I want
to say, eight or ten years ago, But that's really
very feasible today, isn't.

Speaker 3 (57:40):
Oh absolutely, And when you add in all of the
things that ai I mentioned, all of the laborious stuff
that you get rid of with publishing, same is true
in film. So this is going to sound weird, but
you know what eats up like huge amounts of time
and is ridiculous boring color matching. Well, when things are

(58:04):
filmed over a variety of days or locations or what
have you. One day's cloudy, one day's sunny, you've got
to have that match up so that your film appears
of a piece. So it's more than just continuity. Absolutely,
the next step they step beyond that, and there's just

(58:24):
so much that can be done with the visual part,
with the editing ais that we have always going to
have a human editor, but we are giving them tools
that just makes them able to do their job in
a much more creative way because they don't have to

(58:44):
take that hour or two hour and do the Niggadly,
I've got to move this to here, and that to
their They literally can press a button and it happens.
So what we're finding is a great amount of the
workflows in these industries are time consuming, boring, and just

(59:07):
like they take forever, and we can fix that to
the point where they no longer take forever. And the
people were working with absolutely love it because they can
spend their time making that edit like supreme right, we're
giving them back time that they can use artistically.

Speaker 2 (59:30):
So so many people have been pessimistic about AI. It's
gonna kill jobs, it's gonna damage society. You won't know
what to do to believe, to trust, we'll all be
out of work. I don't get the sense that you're
looking at AI that way. You seem to think that
this or sounds like you're finding this is just an

(59:52):
incredibly useful tool and it's gonna make all of us
more productive and more creative.

Speaker 3 (59:57):
Precisely, you know, we always frightened when some new technology
comes on the scene. And by the way, this goes
back forever, like when the Latites right, the Ludites right,
It goes back to Ned Ludd and who broke up
all the machines because they were going to take their jobs.
While he ended up working on one of those looms,
and he vastly preferred his new job because he didn't

(01:00:19):
have to do it the old horrible way. Same thing's
going to happen here, but it happens all the time, right,
So when records first came out, you know that symphony
orchestras took full page ads in newspapers saying that isn't
real music. Real music is live and you have to

(01:00:39):
hear it live or you're listening to a counterfeit. Right,
So when this type of advance comes along, you always
axiomatically people get freaked out. I think, you know, AI
is not going to take your job. A human being
using the AI tool will because they are going to

(01:01:02):
be so much more proficient at what they're doing. They're
going to have so much more time to focus on
the really high value stuff and not have to worry
with all the stuff that you know they had to
do in the past. But now we can automate it
through AI workflows. So I subscribe to what they call

(01:01:24):
the Sentataur model. You remember the mythical be sure half horse,
half man. That's what is going to happen with AI.
It's going to be AI plus human being. That's where
all the great stuff is going to come. Right now,
we're going to see a tsunami of slop that's going

(01:01:44):
to be just AI generated and people will think, oh,
that's good enough, right, and so going forward, you can
create a huge edge by having good taste and curating
itll but I can guarantee you almost all of that
is going to be human using AI as a tool

(01:02:05):
to make their jobs better, easier, more creative. The way
I look at it is, you know, Steve Jobs famously
said computers were bicycles for your mind. AI is a
rocket ship for your mind. Huh.

Speaker 2 (01:02:18):
I like the way you phrase that. You know. Someone
once asked me, you know what's the secret to putting
out the daily reads? And my answer was curate viciously exactly.
And you you know, AI. I don't think in our
lifetime and probably not our kids' lifetime, is going to
reach the point where it can be a taste maker.

Speaker 3 (01:02:40):
We believe, passionately believe that if you have good taste
and you are a great curator, your future looks incredible
because you'll be able to use these tools. You won't
have to spend all the time that you used to
and that's going to even make It's going to be
the rocket ship to give you get you to the

(01:03:01):
next level of your good taste and curation.

Speaker 2 (01:03:03):
So a couple more questions before we get to our
final question, and that is first, I have to ask
you about the O'Shaughnessy Fellowship, what I've been calling your
MacArthur Reward. Tell us a little bit about the support
you offer for young entrepreneurs. What inspired you to start

(01:03:25):
this program. I know we've had at least one O'shaughnessee
Fellowship person, Kyle Scanlon, as a guest on the show,
maybe one other. I'll have to go through the list
and see what motivated you to create this program and
how has it been running.

Speaker 3 (01:03:43):
So it's running really, really well. We have the applications.
We're now in our third year. The applications are much
more numerous and the quality of the applicant I mean
very literally. If I could, would give most of our fellowships.
But the real reason that I did it was because

(01:04:06):
I had become convinced that geography, time and space have
all collapsed and in the old days, you know, you
and I would know each other still because we both
live here in New York and we both are in
the same business. But other than that, like prior to
the Internet, prior to what I call the human Colossus,

(01:04:27):
we couldn't find those geniuses elsewhere. We can now, and
I believe that it is absolutely imperative to show the
world that there are a ton of brilliant people in
this world, many of them young, who don't have an
opportunity to demonstrate what they have to offer to the world.

(01:04:51):
Now we can find and more importantly, fund them. And
the way we do it is it's totally no strings funding.
So if you're a fellow, you get one hundred thousand
dollars over a one year period to work on your project.
If you're a grantee, you get ten thousand. We have
obviously many more grantees than we have fellows, but just

(01:05:14):
the blossoming of the way the groups work together. Like
I thought that it would take us at least five
years to build like a really cool network of super smart,
switched on people, it's already happened. We have we have
in person meetings once a year, and the last one

(01:05:36):
we had I'll just give you a quick example. We
have a scientist who is developing an in home way
to test your babies poop to make sure that it's okay.
She had no idea how to market this. Another fellow
was sitting right next to her. He's a writer, he's
a thinker, and he knows all about this, and literally,

(01:06:00):
or the course of an hour and a half, he
gave her a completely different marketing plan that she adored.
She came over to me and she said, I can't
believe that in an hour and a half he totally
changed the way I'm going to bring this to market.

Speaker 2 (01:06:15):
Huh.

Speaker 3 (01:06:16):
So the cross polonization and the synthesis of these great
minds is really a thing to behold. I'm just very,
very excited about what's coming out.

Speaker 2 (01:06:27):
And before we get to our favorite questions, I want
to throw you a curveball.

Speaker 3 (01:06:32):
Curveball.

Speaker 2 (01:06:33):
So, since we first met back in a CNBC green
room in the early two thousands, so a few decades ago,
you've had a fairly unique perch on the world of
finance and investing in asset management. How has financial media

(01:06:53):
and asset management changed over the course of your career.

Speaker 3 (01:06:58):
Well, at the beginning of my career, kind of squawk
box on CNBC was the gold standard and the format
they used at that time. I used to co host
with Marcain's All the Time.

Speaker 2 (01:07:12):
I've done a few times.

Speaker 3 (01:07:13):
Back then it was a three hour program in which
the portfolio manager or these strategists that we were talking to,
was given like twenty minutes to actually articulate their thesis
about why they were bullish or bearish, why they liked
this particular group or that particular group. So one of

(01:07:35):
the things that I saw happening when that changed was
we were not giving the audience like that kind of treatment,
which is really really incredible treatment. It was a three
hour period that gave you enough time to actually talk
things out. Now what's happened. Podcasts like yours really have

(01:07:59):
come along and you've replaced that aspect, And so you know,
I would bemoan when I saw that happening with Squawk especially, Oh,
I would really wish that they could return to the
old format. But then you and many many other my
son with as absolutely came in and filled the void.

(01:08:20):
So I think what investors are able to get access
to now is just it. Dwarfs are the early days
when you and I met in that green room. They
have so many podcasts they can choose from the can
they can still watch financial media. Then there's the YouTube people.

(01:08:42):
But like everything, you've got to aggressively curate somebody like you.
You know, you're way up here and you're kind of
the gold standard. But how many shows have you done?
You you have proof of work.

Speaker 2 (01:08:55):
I'll tell you a funny story. So we're July will
be an years. It's five hundred and fifty shows. The
Origin story. I don't know if I ever told this
on my own podcast. I'm pretty sure i've told it elsewhere.
It's coming back from a conference in Vancouver, Canada, and

(01:09:15):
I had to either change planes in Chicago or Montreal.
I and remember coming back to New York and I'm
in the lounge and I want to say it was
CNBC and they were interviewing Bill Ackman. I could be wrong.
Maybe it was Einhorn. I don't remember, but it was
a fund manager like that who back then was not

(01:09:36):
There's no Twitter, they weren't doing a lot of TV.
They like, you really don't go on TV unless you
were marketing or had a really good quarter. And I
just remember hearing the worst like it was a five
minute hit, not a twenty minute hit. That's right, And
when you have five minutes, it's what's your favorite stocks,

(01:09:58):
when the head gonna cut, where the dew going to
be next year? Thanks for coming by, and the moment
that guy walks out of the building. Those answers are stale.
And so I was flying back after you changed planes.
I bumped into a friend and I was kind of
like grinding my teeth and he's like, what's on your mind?
You look like you're annoyed, and I relate the story,

(01:10:20):
and he said, what questions would you ask? And the
questions we're about to ask I'm about to ask you
those were some of the questions. Who are you? How'd
you get that way? What are you reading? Who your mentors?
How did you develop your philosophy? If you were giving
me advice as a college grad, what would you tell
me if I wanted to go, like just off the

(01:10:42):
top of my head, sure, just because I wanted the
person to have to use the word you used earlier,
agency and control over the story, but also express what
they've learned over the decade exactly, and thirty seconds doesn't
give you that. So on that note, let's let's jump

(01:11:02):
to our speed rounds, to our favorite questions that we
ask all of our guests. I think this is probably
the third or fourth time I've had you do these.

Speaker 3 (01:11:12):
I hope I don't give answer.

Speaker 2 (01:11:13):
Hey, listen, We'll have AI go through it and find
out how you're how you're thinking has evolved.

Speaker 3 (01:11:18):
Let's there we go.

Speaker 2 (01:11:19):
I love that, right, So starting with what's keeping you
entertain these days? What are you watching or listening to?

Speaker 1 (01:11:27):
So?

Speaker 3 (01:11:27):
Uh, mostly listening to the normal group of podcasts that
you would yours, my son's, my own.

Speaker 2 (01:11:37):
But do you find listening to your own is a
challenge in that it sucks up time that you can't
listen to others, or you don't want to listen to
somebody you're going to interview and you don't want someone
else's questions.

Speaker 3 (01:11:50):
So my dirty little secret is that I very very
seldomly listen to my own. I do read the transcripts
just to make sure, Oh I really screwed that up.
I got to fix that.

Speaker 2 (01:12:03):
Transcripts don't come across the same way.

Speaker 3 (01:12:05):
I know, I know, I know, but I prefer to
give my active listening time to like your podcast and
and Patrick's. In terms of reading, I continue to read
very very broadly My favorite, uh sort of literary fiction
author is David Mitchell, who wrote Cloud Atlas. Oh really,

(01:12:25):
and I've.

Speaker 2 (01:12:26):
Started Reade into a movie. Yeah.

Speaker 3 (01:12:28):
Yeah, the book's much better than the movie. And I
love Howard Bloom's work.

Speaker 2 (01:12:35):
You know, the He's Closing of the American Mind.

Speaker 3 (01:12:38):
No, no different guy, sounds like right. Howard is a
very fun, eccentric genius who sort of started life as
a scientist and now takes all of what he learned
there and applies it to the social world or the
business world.

Speaker 2 (01:12:54):
Closing of the American Mind, entertaining ourselves.

Speaker 3 (01:12:57):
One of his would be the Lucifer principle, about how
all of our evolutionary things that are driving a lot
of our actions have profound implications for markets, for societies,
for all of these things. And like, he's got a
great book caming Reimagining the Beast where he talks about capitalism, saying, hey,

(01:13:22):
capitalism is hands down the winner, but we can still
improve it, and we should improve it. And here's how
I think we should. So love his work. Read pretty
much any paper I can get my hands on having
to do with advances in AI and and that sort

(01:13:43):
of thing. For fun. I just saw the new Bob
Dylan movie. Loved it and Complete Unknown, And I also
love the way Timothy Challow may the lead in that.
I loved his speech when he got up and said,
you know what, I could say, oh shucks, and I'm nothing,

(01:14:05):
but I want to tell you something. I am aspiring
to greatness. I want to be great. And I love
actually seeing the younger generation start saying things like that,
because it's so for so often, you know, we we
you know, wasn't really anything. Come on, false humility, false humility,
just like it stands out, doesn't it jar when you

(01:14:29):
hear it? And it's like when I heard him give
that speech, I'm.

Speaker 2 (01:14:32):
Like, right on.

Speaker 3 (01:14:34):
That's where I love hearing from a young actor or
a writer or whatever. I Hey, I aspire to this.

Speaker 2 (01:14:41):
Don't we all aspire to greatness? Or we should, like
you get one run, make it make it worth.

Speaker 3 (01:14:49):
Something, make it worthwhile. And so I was very happy
to see that again just for total fun. I love
Billy Bob Thornton. So we really enjoyed Land. Man.

Speaker 2 (01:15:01):
You know, you're like the third or fourth person who
told me how much they love that, sir.

Speaker 3 (01:15:05):
It is so much. It's just fun and so You're
probably not gonna learn a lot by watching it. Other
than that Billie Bob Thornton choose up every scene that
he appears in. He's such a good actor.

Speaker 2 (01:15:19):
Always is every time I see him me too. He's
a delight. You know. You have such an interesting background.
I'm curious if you had any mentors help shape your career.

Speaker 3 (01:15:31):
I did. I had a gentleman who was when I
was very, very young. I'm not gonna mention his name
because some of his kids might be listening, but we'll
go with Jim. He was also a Jim and he
probably did more for me when I was young and

(01:15:53):
filled with you know, vinegar and very definitive beliefs. And
I'll tell you all, I'm going to proselytize this is
the way to do it. And he was really really
good at saying, Uh, Jim, you might want to take
that a step back, because what do you really want?
I want people to know about this, Okay, but what's

(01:16:15):
the broader implication here? Process over outcome? Okay, Well, why
did you talk a little bit more about that? Why
don't you talk about the way that people can actually
take what you're saying to them and make them useful
in their own life. So he was an amazing mentor
to me because he was very patient, wicked sense of humor,

(01:16:38):
and always good at reminding me that you might want
to take it back an ouch or two.

Speaker 2 (01:16:45):
That's great. Let's you mention a few books, any other
favorites you want to mention before we get to our
favorite questions.

Speaker 1 (01:16:53):
The the what?

Speaker 3 (01:16:55):
Let me reference our infinite books. We have a list
that you can get anywhere. You can go to Twitter,
you can go to our substack, and it's kind of
our seminal books, you know, books like the Beginning of
Infinity by David Deutsch I think is a masterpiece. Beginning
of Infinitinity by David Deutsch, who's a quantum physicist in

(01:17:16):
the UK. I love all of his work, but I
also think people should be reading things like my perennially
read The Dowdy Jing by Lautsu. It packs a wallup man,
because you can read the whole thing in an hour.
But I used to joke, you know, I started reading
that when I was eighteen, and I read it every year,

(01:17:38):
sometimes multiple times every year, and I finally started to
understand it when I was about fifty five.

Speaker 2 (01:17:44):
I was gonna say it's a different book each time
you read it. It really is.

Speaker 3 (01:17:47):
It's like heraklitis. You know, no man steps in the
same river twice because it's not the same man and
it's not the same river.

Speaker 2 (01:17:55):
Absolutely, all right. Our final two questions that we ask
all of our guests what sort of advice would you
give to a recent college grad interested in a career
in either investing, quantitative analytics, or venture capital.

Speaker 3 (01:18:12):
Understand the leverage that you get from all of the
new AI tools. It gives you several advantages. The older
people on those desks might not be rapidly adopting those tools.
And if you walk into a job interview with some

(01:18:36):
mastery of them, what they're doing in terms of what
they can uncover for VC, for traditional long only or
long short management is staggering. Get a deep domain knowledge
there as it fits into your particular passion, be it

(01:18:57):
investing or an analysis, etc. But that would be my
number one piece of advice.

Speaker 2 (01:19:05):
Wow, And our final question, what do you know about
the world of investing today that would have been helpful
back in the nineteen nineties when you were first starting out.

Speaker 3 (01:19:15):
People don't change, markets change, And when I really really
came to understand that was after actually the Great Financial Crisis.
I went through the crash in nineteen eighty seven, I
went through the other bear markets, but I didn't really

(01:19:38):
lock in on the fact that markets change millisecond by millisecond,
human behavior barely budgees millennia by millennia. Arbitraging human nature
is the final moat. Arbitraging human nature is the final moat.

(01:19:59):
That's fantastic place to end it. Jim, thank you so
much for being so generous with your time and for
being just such a great colleague, mentor source of wisdom.
Like it's been my privilege to know you my whole career.

Speaker 2 (01:20:17):
I remember, I want to say it was like the
late two thousands, sitting at an outdoor on a Starbucks.
I remember one of my well don't we know each other?
And it was it was just like one of those
small world moments. And you've always been just so thoughtful,
so inspiring, and your insights just I know so many

(01:20:43):
people you've had such a positive impact on. It's just
a delight and a pleasure to.

Speaker 3 (01:20:49):
Know you well right back at Youbury. It's been my
great pleasure knowing you all of these.

Speaker 2 (01:20:56):
Years, so this mutual admiration society has to come to.

Speaker 3 (01:20:59):
An It's a bromance.

Speaker 2 (01:21:03):
We have been speaking with Jim O'Shaughnessy, founder and CEO
of O'shaughnessee Ventures. If you enjoy this conversation, well check
out any of the five hundred previous ones we've had
over the past ten, almost eleven years. You can find
those at iTunes, Spotify, YouTube, Bloomberg, or wherever you find

(01:21:25):
your favorite podcast. Be sure and check out my new book,
How Not to Invest The Bad Ideas, numbers and Behaviors
that Destroy Wealth, coming wherever you get your favorite books
on March eighteenth, twenty twenty five. I would be remiss
if I did not thank the crack team that helps
put these conversations together. Anna Luke is my producer, Meredith

(01:21:48):
Frank is my audio engineer. Sage Bauman is the head
of podcasts at Bloomberg. Sean Russo is my researcher. I'm
Barry Rutults. You've been listening a Master's in Business on
Bloomberg Radio.