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." See omnystudio.com/listener https://omnystudio.com/listener for privacy information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

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• 2:40Speaker 03

  This is Masters in Business with Barry Ritholtz on Bloomberg Radio.

• 2:47Barry Ritholtz?

  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 generations of quants on finance. O'Shaughnessy Asset Management became a leader in direct 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.

• 3:29Barry Ritholtz?

  His new book is delightfully titled, 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 he answers wherever 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.

• 4:13Speaker 05

  Barry, I am always looking forward to these conversations. It's great to be back.

• 4:18Barry Ritholtz?

  It's a pleasure for me also. You and I go way back.

• 4:21Speaker 05

  Way, way back.

• 4:23Barry Ritholtz?

  And it's kind of funny, like 25 years later, I was like, oh, how do you know Jim? Oh, we met in the green room of TV.

• 4:29Speaker 05

  Yeah.

• 4:30Barry Ritholtz?

  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 time you were getting ready to depart Bear Stearns. You were at Bear Stearns for like a decade or so?

• 4:52Speaker 05

  No, about five and a half years.

• 4:54Barry Ritholtz?

  Okay, so in the mid 2000s and you had the great insight and business acumen to tap out of Bear Stearns in 2007 with all of those options that you had and exercise the options, sell them and launch your Shawnessy Asset Management. So you win on the way out, you win on the way into starting the new firm. Tell us a little bit about the early days leaving Bear Stearns and setting up OSAM.

• 5:28Speaker 05

  So first, let me correct the, everyone assumes that I saw the great financial crisis coming and therefore wanted to spin out of Bear Stearns.

• 5:39Barry Ritholtz?

  Take the win.

• 5:40Speaker 05

  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 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 it was very, very amicable. But of course, because the great financial crisis came along and Bear had those CDO

• 6:21Speaker 05

  funds that had a little bit of a problem, it was just irresistible for news people to say. I had one reporter sit with me for an hour and a half and all she kept doing was, come on, tell me the truth, tell me the truth.

• 6:39Barry Ritholtz?

  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 gotta get a publisher that wants it unless you're gonna self-publish. You gotta, then you gotta write it. So it's like a one or two-year lag. I would imagine pulling out a substantial, um, division from a major brokerage firm doesn't happen overnight. It's gotta be like a six or 12-month process.

• 7:13Speaker 05

  Absolutely. Because you have to have everyone, uh, with the oars going in the same direction. You wanna make sure that, uh, it is agreeable and everyone is, whether they're unhappy that you're going, they're happy with the deal that allowed you to go. 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, and they really got that. And so, very amicable, but as you, as you know, those things take a long time to get negotiated out.

• 7:51Barry Ritholtz?

  Yeah, that, you know, to me, the thing I'm, I was always kinda sad about with the fall of Bear Stearns, eventually picked up for pennies by Jamie Dimon and J, JP Morgan Chase. And then even Lehman Brothers. I, 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, or if they're a salesperson, 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.

• 8:29Barry Ritholtz?

  But the tragedy that a lot of, of laypeople don't know are really good people doing really good work, get, they're the collateral damage from someone else's screw-up.

• 8:41Speaker 05

  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.

• 8:54Barry Ritholtz?

  Well, some were a little more insolvent than others.

• 8:57Speaker 05

  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 down.

• 9:07Barry Ritholtz?

  Right. Bear went down early enough that it was salvageable. And then a little-known story that a lot of people are unaware of, when I was writing Bailout Nation and doing my homework, it turned out that JP Morgan Chase had a little derivatives flare-up like years earlier. And I don't remember if it was Jamie Dimon or one of his lieutenants, but someone said, hey, this is a mess and this is really potentially damaging. And it might have been Dimon who said, sell it all. I don't care the price. If you have to take a 10% or 20% haircut, I want all this off the books. And that's what they did. And so when the world went to hell, they were, they picked up Washington Mutual,

• 9:50Barry Ritholtz?

  they picked up Bear Stearns. 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.

• 10:00Speaker 05

  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 was he wanted the building.

• 10:14Barry Ritholtz?

  Right, right. Which is now overshadowed by their brand-new headquarters on Park. But that was a great octagonical building, which we could see out from our firm's windows on Bryant Park with the glass turret on the top.

• 10:29Speaker 05

  It was a beautiful building.

• 10:30Barry Ritholtz?

  And you walk in and it's like, you know, there used to be Wall Street, and then there was, you know, the Morgan Stanley and Lehman Brothers, sort of off of a...

• 10:40Speaker 05

  Midtown, Times Square.

• 10:42Barry Ritholtz?

  Yeah, not my favorite part, Times Square, right. And then this was just, all right, so very prescient before Vanderbilt was even a thing.

• 10:51Speaker 05

  That's right.

• 10:52Barry Ritholtz?

  And there they are. Now one Vanderbilt is a monster. So let's bring it back to what you're doing. So you leave Bear, you launch O.SAM. You've already had great success with what works on Wall Street. What made you think, I think we're going to develop a series of quantitative approaches to managing money?

• 11:15Speaker 05

  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 70 years. He proceeded to give away the vast, uh, portion of his fortune during his own lifetime. Was it really a fortune? It really was. No kidding? And, uh, what he couldn't give away, he put into a foundation, the I A O'Shaughnessy Foundation, which I think today is still about a hundred million dollar foundation. No kidding?

• 11:53Speaker 05

  And, but he made his five kids the trustees. And so, once a quarter, there would be a dinner and it would rotate. I was brought up in St. Paul. Right. And so during the St. Paul rotation, I got lucky enough, and I think I was 16, to get invited to the adult table. And of course, like, I'd want it to be an adult. And 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 my Uncle John and my dad, and I'm listening. And they're talking about IBM, but they're just talking about the CEO. Uh huh. They're not talking about, how much do they make? How much do you have to pay

• 12:37Speaker 05

  for every dollar of earnings or sales or EBITDA? And I kind of raised my hand and said, Dad, Uncle John, uh, don't you think it might be a better idea to look at it by the numbers? And they dismissed me. This is 1976, right? So what's a pawn? Yeah, exactly. Well, exactly. And so I decided, you know what? I'm gonna go look into this. So I took myself down to the James J. Hill, uh, Research Library in downtown St. Paul. And I thought I was gonna be really ambitious, but I am potentially the world's laziest man. So when I saw the 500 of the S and P, the S and P, uh, tear

• 13:19Speaker 05

  sheet book, I'm like, oh, I'm not, I'm not gonna be able to do that. So I lighted on the Dow. Stocks, right? Right. Did the research, found very compelling evidence that what its PE is really matters to your returns going forward. Very, very high valuations tended to crash and burn, very, very cheap valuations tended to do well. But of course, you know, Barry, I was 16, 17, much more interested in girls. Right. And so after college, got married young, I was like, I've got to revisit all this and got the data set from CompuStat and essentially that became what works on Wall Street.

• 14:03Speaker 05

  So, so wait, so what, what'd you study in college? So, the reason I am in 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. Otherwise you might've been a historian and not a. Absolutely. Well, listen, I think a good knowledge of history is absolutely vital if you want to be a good investor, right? A hundred percent. Yeah, I mean, like one of the, one of the Roman wits said, he who does not understand what happened before they were born remains forever a child. Huh.

• 14:47Speaker 05

  And essentially, I didn't want to remain a child. If you look back at the market's history, guess what? History doesn't repeat itself, but it rhymes. For sure. 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 full, the gods' shell of our stocks take care. Europa, 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

• 15:30Speaker 05

  somebody writes a poem about a stock you own, sell it." That's a top, right? That's a high. That's amazing. And it's funny, you and I both have a love of quotations.

• 15:39Barry Ritholtz?

  And 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.

• 15:55Speaker 05

  Yeah, Quote Investigator.

• 15:57Barry Ritholtz?

  I love that site.

• 15:58Speaker 05

  Yeah, it's pretty good. They can normally get you to the original citing of the text. What's funny about that, though, is almost inevitably, it's somebody you've absolutely never heard of.

• 16:10Barry Ritholtz?

  Right, that's right.

• 16:11Speaker 05

  And I think that's why people like when, that sounds like something Mark Twain would say, right? But then there's also the Mark Twain, Oscar Wilde, I mean, there's a bunch of them. Any quote that you really love and you don't know who did it, people tend to say, Mark Twain, Oscar Wilde.

• 16:30Barry Ritholtz?

  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 true.

• 16:40Speaker 05

  Yeah, that was actually a character of Mark Twain's.

• 16:43Barry Ritholtz?

  Oh, really?

• 16:44Speaker 05

  And he spoke like a southerner of the late 1900s. And I think his last name was Ward, the character's last name was Ward. Twain, I mean, he 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.

• 17:21Barry Ritholtz?

  Which A is true, and B leads to the newer line, if you want a friend on Wall Street, get a dog.

• 17:30Speaker 05

  Yeah.

• 17:31Barry Ritholtz?

  And it's really true. We're gonna talk more about quotes in books in a moment. Before we do that, I just wanna bring up the first book, What Works on Wall Street. That book not only has been through 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?

• 18:01Speaker 05

  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, the manuscript, the first thing they said to me, Barry, was, "We would love to hire you, but you cannot publish this book."

• 18:31Barry Ritholtz?

  You're giving it away. I knew you were gonna go there.

• 18:35Speaker 05

  Exactly. And I was like, "No, no, no, no, no. You can have the greatest truth in the world. You can scream it from all the rooftops. You can take full-page ads in the Wall Street Journal. Most people are just gonna go, 'Meh, they're not gonna do it.'"

• 18:52Barry Ritholtz?

  It's so true. You know, my takeaway from my first book, which is now 15 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 move beyond that." 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 100% right. The fact that they thought you were giving the secret away, you could, "Here's a secret to investing."

• 19:37Barry Ritholtz?

  Maybe you'll do okay with it, but nobody's gonna really adapt.

• 19:42Speaker 05

  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

• 19:51Barry Ritholtz?

  Oh, really?

• 19:52Speaker 05

  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 your manager.

• 20:04Barry Ritholtz?

  Right.

• 20:05Speaker 05

  Note, we used to update the clones versus the manager. Last time we did it was years and years. Years ago.

• 20:11Barry Ritholtz?

  Right.

• 20:12Speaker 05

  But the thing that I found really interesting was all of the clones were beating the managers that they cloned.

• 20:19Barry Ritholtz?

  Was that because of the fee or was that because they're not great sellers?

• 20:22Speaker 05

  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 hung over, they never fight with their spouse. They just keep applying those criteria, year in, year out. And I think that the, you know, we went through 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.

• 20:54Barry Ritholtz?

  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 the, some really fascinating things you learn are when you look at the academic research. Fund manager, fund managers are actually surprisingly good buyers.

• 21:11Speaker 05

  Yes.

• 21:11Barry Ritholtz?

  But they're terrible sellers.

• 21:13Speaker 05

  Yep.

• 21:13Barry Ritholtz?

  And part of the reason is, is the emotionality of the sale. They tend to panic out when they shouldn't, or do the opposite, hold on right to the bitter end when they really shouldn't.

• 21:25Speaker 05

  Well, and also it's just because I, it's just part of our human OS, part of our human operating system.

• 21:30Barry Ritholtz?

  Right.

• 21:31Speaker 05

  I, 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, are you, do you own Enron? And my answer was no, the numbers are pretty bad. Um, and so we don't, and he looked at me kind of, you know, with the chuckle. Ah, you quants, you know? And then he launched into this, uh, description of not only did he hold, he bought more. And then he gave this as the explanation. I went to a barbecue at the CFO's house.

• 22:17Speaker 05

  The CEO was there, the CFO, and I looked them in the eye and I said,

• 22:24Speaker 05

  Is there trouble? And they assured me there wasn't. And I'm just kinda like sitting over there with, oh, okay, just don't touch this one.

• 22:33Barry Ritholtz?

  Right, maybe we could get a short put on this. That's just like, I'll tell you something that's really funny. Um, 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 gonna lie to their investors. Everything's gonna be great. And I very quickly learned, oh, you're a terrible judge of, 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 the numbers.

• 23:17Barry Ritholtz?

  And yeah, I know the numbers can lie, but not as easily as a CEO or CFO.

• 23:21Speaker 05

  That's also a really big part of human OS, default to trust.

• 23:26Barry Ritholtz?

  Well, we're social primates, right?

• 23:30Speaker 05

  We're domesticated primates.

• 23:32Barry Ritholtz?

  Yep.

• 23:33Speaker 05

  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 so, one of the things that we're looking at in one of our divisions at O'Shaughnessy Ventures right now is, uh, voice software AI that does stress analysis on any type of media. So, obviously, earning calls present themselves as kinda number one.

• 24:11Barry Ritholtz?

  Yeah, really.

• 24:12Speaker 05

  And I gotta tell you, Barry, wow.

• 24:14Barry Ritholtz?

  Exciting stuff?

• 24:15Speaker 05

  Oh, my God.

• 24:16Barry Ritholtz?

  Now, how much of that is nervousness about speaking to a large audience? And nervousness because they know something and they don't wanna disclose it?

• 24:25Speaker 05

  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.

• 24:35Barry Ritholtz?

  Right.

• 24:35Speaker 05

  Or, you know, a speech that had nothing to do with earnings. And that creates your baseline.

• 24:42Barry Ritholtz?

  Uh huh.

• 24:42Speaker 05

  And then you get to see very, very quickly, like, Spike! We don't have any worries, Spike!

• 24:52Barry Ritholtz?

  Wow, that sounds like fun.

• 24:54Speaker 05

  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'Shaughnessy Ventures. That was a deal that we made with Franklin Templeton that we would not launch.

• 25:08Barry Ritholtz?

  But you could still do a little, come on, doesn'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 and see where this goes.

• 25:24Speaker 05

  Yeah, you know, if you can keep a secret, we might try that with some of our internal capital.

• 25:30Barry Ritholtz?

  Let me know, I'm right there with you. I love the idea of that.

• 25:33Speaker 00

  At KKR, we've spent 50 years understanding what matters to our clients and companies. From pioneering private equity to investing across credit, real assets, insurance, and sports, KKR has built the experience to navigate complexity, the judgment to recognize opportunity, and the conviction to create lasting value. Because when people and institutions are counting on us, understanding what matters isn't just important, it's everything. KKR, understanding what matters. Visit kkr.com/whatmatters.

• 26:05Speaker 02

  This is the Bloomberg Tech Minute brought to you by ChatGPT. I'm Carol Muster. Millions of Americans are taking peptides, short strings of amino acids that can act as biological signals for cells. Peptides like insulin can occur naturally in the body, or they can be synthetically introduced to induce a biological process, as happens with semaglutide, the active ingredient in Ozempic. Now Bloomberg's Anika Inamputi reports peptides may be exploring their next frontier, the brain. People are taking peptides for mental clarity and cognitive benefits as alternatives to psychiatric medications and to gain a competitive edge or stave off the effects of aging. Both insulin and semaglutide are approved by the U.S. Food and Drug Administration.

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• 27:27Barry Ritholtz?

  Where did the title come from?

• 27:30Speaker 05

  So it came from a group of my teammates at OSV. Essentially, I have been a quote junkie all of my life.

• 27:40Barry Ritholtz?

  Same.

• 27:41Speaker 05

  So I have kept, I, I, Barry, have notebooks filled with quotes.

• 27:46Barry Ritholtz?

  Oh, really?

• 27:46Speaker 05

  From way back when I, I think the first time I started it, I was 21.

• 27:52Barry Ritholtz?

  Uh huh.

• 27:52Speaker 05

  And so I just love them. And, 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 a quote.

• 28:07Barry Ritholtz?

  I do that a lot also. I find that's fun. Let me, let me ask you one other question about the, the title. So one of the things that's fascinating, if you're, if you like music or poetry, or even, I'm going to go into the weeds, Shakespearean I amic pentameter.

• 28:27Speaker 05

  I love all those.

• 28:28Barry Ritholtz?

  Okay, so there is a rhythm to, and I'm going to write this down. So you know, even if, if you get this, I want you to know, um, 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 was in your mind when you came out with this.

• 28:53Speaker 05

  Oh, you got me on that one.

• 28:54Barry Ritholtz?

  A heartbreaking work of staggering genius. A timeless collection of infinite wisdom. It just leaps off in that same rhythm.

• 29:04Speaker 05

  I love that connection.

• 29:05Barry Ritholtz?

  I don't know if that was a.

• 29:06Speaker 05

  No, at least it wasn't in the back of mine. No, wasn't, wasn't purposeful.

• 29:10Barry Ritholtz?

  Cause I, I've always loved that title.

• 29:13Speaker 05

  Oh, it's a great title.

• 29:14Barry Ritholtz?

  A heartbreaking work of staggering. And, and it's like, you could go with a different, it's a staggering work of heartbreaking genius. Like you could flip it around.

• 29:22Speaker 05

  Yeah.

• 29:22Barry Ritholtz?

  But this phraseology just leapt, that leapt right out of me.

• 29:27Speaker 05

  I, I am incredibly lucky to have in. 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.

• 29:48Barry Ritholtz?

  Well, I know, I know you have been tweeting for, I don't know, 10 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 gonna be happening in August, but I think this is relevant. You have been doing two tweets for forever.

• 30:12Speaker 05

  Yeah. And so it was kinda 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 gonna 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 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.

• 30:56Speaker 05

  Literally, we iterated, iterated, iterated, and ended up publishing the book.

• 31:02Barry Ritholtz?

  Huh, so that's really interesting. 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 complement each other? Are you looking for their most, two most profound statements? How are you selecting A and B for this author?

• 31:24Speaker 05

  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 time going through the rest of their work, et cetera, finding one that would complement it. But then sometimes... Some of the best two quotes that work the best, they don't complement each other. In other words, it's kind of like, hey, you know, history rhymes.

• 32:06Speaker 05

  But then the second quote is, but always keep your eyes on the horizon, right? Like, hmm.

• 32:13Barry Ritholtz?

  Two very different.

• 32:14Speaker 05

  Two very different things. And so I, I, I, I wasn't precious about it at all. Literally because it just grew out of me throwing two quotes from the same author 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.

• 32:34Barry Ritholtz?

  Organically grew out of it. Hey, if you do something, my experience has been tacking into what works.

• 32:41Speaker 05

  Yeah.

• 32:41Barry Ritholtz?

  And, you know, it, it's not quite direct mail.

• 32:45Speaker 05

  No.

• 32:45Barry Ritholtz?

  Where, hey, we're getting a response from this, but not that. It's not exactly an A B test, but hey, people seem to like this. Let's give them more.

• 32:53Speaker 05

  Yeah. And, and that's what happened here, you know, like one of 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. And so momentum in this regard, you see all the DMs increasing, hey, when are you going to do the book for this? Hey, where's the newsletter, et cetera? And I'm like, okay, this is, this is truly emerging from beneath, not from me saying, you know what, I'm going to do a two quotes book and it's going to be great.

• 33:37Speaker 05

  No, this was all others in the marketplace saying to me, hey, Jim, do a two thoughts book.

• 33:43Barry Ritholtz?

  A grassroots groundswell. So, 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? We, we, this Bartlett's Book of Quotations and that's alphabetical.

• 34:00Speaker 05

  Yeah.

• 34:00Barry Ritholtz?

  And you know, that's a research piece, but you're putting this out as less of an encyclopedia and more of a, um, nonfiction. How'd you think about how you wanted to structure it and organize?

• 34:11Speaker 05

  We went back and forth on that forever. And then we decided, okay, let's, uh, let's separate it by broad groupings like thinkers, uh, writers, authors, um, you know, dynamos, people who founded companies and were incredibly successful. Um, and we, in the hardcover of the book, um, we made sure that each one was color quoted, uh, because really the book is not meant for you to sit down and read all the quotes in it.

• 34:46Barry Ritholtz?

  Right.

• 34:46Speaker 05

  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, cause you'll see two quotes on each page, um, and kind of think about them. And because people are, and by the way, that's the way everyone I've ever talked to has a copy of the book. That's the way they're using it.

• 35:10Barry Ritholtz?

  Mm-hmm.

• 35:10Speaker 05

  And, 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 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.

• 35:32Barry Ritholtz?

  Right.

• 35:32Speaker 05

  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.

• 35:39Barry Ritholtz?

  It, it inspires them. So based on that, let me suggest, We need a two-quote-a-day desktop calendar where, like, do you remember those old ones?

• 35:49Speaker 05

  Of course I do.

• 35:50Barry Ritholtz?

  Where you just pull, you know, just, it was almost like a giant pad of, uh,

• 35:55Speaker 05

  Mine, mine, mine was a Far Side calendar.

• 35:57Barry Ritholtz?

  I was about to say that. I still have this, in my head, the School for the Gifted, where he's pushing on the, and the door says, "Bull." Like, I, from that exact same calendar.

• 36:09Speaker 05

  Exactly, exactly.

• 36:10Barry Ritholtz?

  I had one of those, and I had a Calvin and Hobbes, and it's like a different one every day.

• 36:14Speaker 05

  Another one of my favorites.

• 36:15Barry Ritholtz?

  Absolutely, that's so funny. So, let's talk about what are real quotes and what are 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, uh, they liked the bo, the book, "P.S. This is an urban legend, Thomas Jefferson never said this." And, um, that's how I ended up eventually tracking down Quote Investigator, 'cause I was so horrified, and one person said something, nobody ever mentioned it again.

• 36:54Speaker 05

  Yeah.

• 36:55Barry Ritholtz?

  And it was like, alright, so the good news is, the bad news is, what a screw-up, the good news is, nobody noticed, how did you go about 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.

• 37:13Speaker 05

  Sure.

• 37:13Barry Ritholtz?

  Apparently said all these things they never said.

• 37:16Speaker 05

  Right.

• 37:16Barry Ritholtz?

  Uh, "Compounding is the eighth wonder of the world."

• 37:19Speaker 05

  Wonder of the world, right.

• 37:20Barry Ritholtz?

  Einstein never said that.

• 37:21Speaker 05

  Yeah, no, I know. Um, so, there I was very lucky to have a very diligent team, and they identified a host of sources, we used Quote Investigator, uh, but we used others as well, uh, to try to get the veracity of the author and the quote right. Now, having said that, I'm sure that there are still some examples in there where we got it wrong.

• 37:48Barry Ritholtz?

  Right.

• 37:48Speaker 05

  And so, we even put a little thing in there saying, you know, it all errors-

• 37:52Barry Ritholtz?

  Hey, we did our best.

• 37:53Speaker 05

  Yeah, all, all errors are our own, right? Um, but philosophically, I have a little bit of a different view of this. I, I think that we all too often, because we, we anthropomorphize things to the extent where-

• 38:10Speaker 05

  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 is the eighth wonder of the world. You know what? You and I know that's true.

• 38:25Barry Ritholtz?

  It actually is true.

• 38:26Speaker 05

  We know that's true. And so what's more important? That idea getting into somebody's head? Or that Barry Ritholtz 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.

• 38:43Barry Ritholtz?

  You want to be accurate.

• 38:44Speaker 05

  You want to be accurate, absolutely correct. But with me, it's always more like, I'm 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, um, any kind of philosophical statement sounds better if you put the name 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.

• 39:27Speaker 05

  Right? It's like, hmm, I want people to really take this seriously. So I'm going to make sure that Einstein said this. So that, you know, it doesn't add to what the, what the thought is inspiring in you.

• 39:43Barry Ritholtz?

  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, it wasn't by that person.

• 40:04Speaker 05

  Yes.

• 40:05Barry Ritholtz?

  And any come to mind?

• 40:06Speaker 05

  Um, well, we had quite a few, um, actually Eleanor Roosevelt quotes.

• 40:14Barry Ritholtz?

  That were not Eleanor Roosevelt.

• 40:15Speaker 05

  Not Eleanor Roosevelt.

• 40:16Barry Ritholtz?

  Really?

• 40:17Speaker 05

  And we had a lot of, well, not going back over the obvious ones. Einstein, you know.

• 40:24Barry Ritholtz?

  Twain, Carlin.

• 40:26Speaker 05

  Uh, George Carlin, um, Oscar Wilde, et cetera.

• 40:30Speaker 05

  And if we love the quote, we would put it in under the actual author's name. And I can't, 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 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.

• 41:13Speaker 05

  And I said, what do you guys think of the first one? Lots of emojis and everything. And then I put it up with the other woman's name.

• 41:23Barry Ritholtz?

  The less famous actual author.

• 41:25Speaker 05

  Actual author, crickets. And so to me, there's obviously something being activated in our brain that says, ooh, 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.

• 41:50Barry Ritholtz?

  And, 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.

• 42:06Speaker 05

  Exactly.

• 42:07Barry Ritholtz?

  It's not quite social proof, but hey, if it's Oscar Wilde or Mark Twain, we know they were wordsmiths and brilliant. And hey, if they said it, it must be valuable.

• 42:17Speaker 05

  Must be good.

• 42:17Barry Ritholtz?

  Right. Or, or, and I wonder if that's why people, you know, attribute thing to, to George Carlin and to say nothing of Einstein. So, so you co-wrote this book. Tell us a little bit about your co-author, Vassil Kaushik. How did you guys handle the, the workload? Did you, was he more organizational and you more philosophical? I know you're. Deep down inside a philosopher. Tell us, how did you go about putting the work together?

• 42:46Speaker 05

  So Vassal 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 Vassal who came to me and said, "Okay, Jim, you've 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.

• 43:30Speaker 05

  But then he also did a 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 that I absolutely loved and he just wasn't finding a place to fit it in, then I would say, "Well, try harder."

• 44:03Barry Ritholtz?

  All right. So 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?

• 44:23Speaker 05

  So it was not necessarily because, hint, there'll probably be another version of this book coming out.

• 44:32Barry Ritholtz?

  Could be 10 more versions of this book, right?

• 44:34Speaker 05

  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 of Enlightenment authors and thinkers. You know, your Adam Smiths, your... Or, you know, all the, the people who were like, wait a tick. We, we could actually do things that we might call the scientific method and really test all of our beliefs. Uh, much to the chagrin of the ruling churches of the, uh, time period. And so Voltaire, always big, big fan of his work.

• 45:15Speaker 05

  Um, and you know, but I, I didn't go at it from that, uh, vantage point. What I really wanted to do because of the nature of the book. In other words, I never expected anyone to sit and 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 an idea, to think about it.

• 45:54Speaker 05

  I just was very much not, you know, I'm not going to make it obvious and I'm not going to, uh, follow them in sequential order. Or, you know, this group all are together and absent from other places in the book. Um, 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.

• 46:20Barry Ritholtz?

  Why a book? Why not some other media? You're so, you know, digital forward and have been for a long time. Um, I, I always find, I like physical books, but you know, you and I are from a earlier generation. Everything seems to be moving in a different direction.

• 46:39Speaker 05

  It is, but, um, number one, like, if you look at O'Shaughnessy Ventures, it's everything that I love. Um, like infinite books, the publisher, uh, infinite film. I love movies, uh, the fellowships, which you know all about. Uh, but. I think that it's not just people of our generation who like beautiful books. In fact, the people who were the most excited about it were younger people.

• 47:09Barry Ritholtz?

  Oh, really?

• 47:10Speaker 05

  Because we took a great deal of care to make it beautiful.

• 47:14Barry Ritholtz?

  Mm-hmm.

• 47:14Speaker 05

  And we had the printer from Italy do the printing. And it's got color and the spine isn't glued. So the number of younger people, and when I say younger, anyone probably under thirty-five. Uh, the notes that I would get saying, "This is the most beautiful artifact."

• 47:36Barry Ritholtz?

  Uh-huh.

• 47:36Speaker 05

  And I heard that term more than once, artifact, artifact. So there, so one was a friend and 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."

• 47:53Barry Ritholtz?

  Right?

• 47:54Speaker 05

  And, and so that was surprising to me, but I love, I love books. You know, I, I, I have big libraries at my house. Um, what, I mostly, by the way, Barry, read on Kindle for iPad.

• 48:10Barry Ritholtz?

  Really?

• 48:11Speaker 05

  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 friends.

• 48:24Barry Ritholtz?

  Huh.

• 48:25Speaker 05

  And, and so 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 everyone seems to like it.

• 48:39Barry Ritholtz?

  There's, there's a certain tactile

• 48:41Speaker 05

  Yeah.

• 48:42Barry Ritholtz?

  feel. I, I used to love the

• 48:44Speaker 05

  Me too.

• 48:45Barry Ritholtz?

  all the 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 at once.

• 48:59Speaker 05

  It's a different experience.

• 49:00Barry Ritholtz?

  Yeah, very much so.

• 49:03Speaker 02

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• 50:25Barry Ritholtz?

  So let's talk a little bit about both Oshaunesi Ventures and OSAM. I sort of look at them as part of the continuum on your, on your career. You let your son Patrick take over as CEO of, of Oshaunesi Asset Management. He was a key driver of Canvas, which was built on top of a database that you've been refining since the 1990s. Do I have that right?

• 50:54Speaker 05

  Yeah, yeah. And actually, you might remember I started the first online investment advisor called Netfolio.

• 51:02Barry Ritholtz?

  That's right.

• 51:02Speaker 05

  In 1999, 2000. I was just, you know, 23 years too early. And I also made the mistake of making it B to C, whereas that was a 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 outcomes were just so much better. So we started building the tools that became Canvas during

• 51:47Speaker 05

  the great financial crisis. I'm like, okay, we're probably not going to sell another long only US stock portfolio for the next three years. So let's really attack the data. Let's clean it. By the way, really hated by my research team for that entire period.

• 52:05Barry Ritholtz?

  Right.

• 52:05Speaker 05

  Because it's really mind numbingly bad. 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, 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 lore, but he goes, we built the Death Star to kill a mouse here.

• 52:47Speaker 05

  And I'm like, what do you mean? He goes, well, our, our clients, the, the Ritholtz 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 NetFolio, 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 long time.

• 53:15Barry Ritholtz?

  What, what, you know, I, our mutual friend, Dave Nodig, 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 200-page quarterly appointments and it's not very fine-tunable. And I'll never forget when Batner came back to the office, having seen a demo. If he had hair, it would have been on fire. Like, that's what it was like. He was jumping up and down. And just the demo was like, oh, wow, this is slick. And wow, this really looks good. I can't believe it's that definable.

• 54:00Barry Ritholtz?

  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.

• 54:18Speaker 05

  Yeah, no.

• 54:18Barry Ritholtz?

  Kind of fell out of the blue.

• 54:19Speaker 05

  Yeah, no, it was not to pump 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 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?

• 55:02Speaker 05

  They don't think about, well, who's the clearance agent? Who's the custodian? All of those types of things. So by actually having people 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, 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.

• 55:47Speaker 05

  We think other people might really like this, too.

• 55:50Barry Ritholtz?

  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 10 or 20 of the largest firms in the world all moving in the same direction, hey, pay attention, something's going on in that space.

• 56:15Speaker 05

  Customization is the future. 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 like tax alpha that you can generate.

• 56:36Barry Ritholtz?

  So you mentioned you were AI earlier. I know you've been appointed chairman of the board at Stability AI.

• 56:42Speaker 05

  I was.

• 56:44Barry Ritholtz?

  So that's no longer, so let me rephrase that question. So you mentioned AI earlier. How do you see AI transforming either the investment management industry or venture capital? What is the role of AI going to be going forward?

• 56:59Speaker 05

  I truly believe that AI is the most powerful technology that has ever come on the scene during my career.

• 57:08Barry Ritholtz?

  Wow.

• 57:09Speaker 05

  And it is going to be used primarily for replacing arduous, boring, mind-numbing type activities that humans are currently doing, the 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 send it in, you probably had this experience.

• 57:36Barry Ritholtz?

  Typos, typos, typos.

• 57:37Speaker 05

  Right, typos, typos, typos. But it didn't get back to you probably for a couple of months.

• 57:42Barry Ritholtz?

  Right.

• 57:43Speaker 05

  With infinite books, it'll probably get back to you the next day.

• 57:47Barry Ritholtz?

  Really?

• 57:48Speaker 05

  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 gonna look as a book, it kinda freaks you out. You start reading it differently.

• 58:07Barry Ritholtz?

  Very much so.

• 58:08Speaker 05

  And so 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 wanna 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 you said the exact opposite thing, which one do you want?" And then finally, we have plagiarism routines, where, you know, a million little pieces where you have to go on and get scolded by Oprah, well, should never happen again. Because sometimes people aren't plagiarizing intentionally.

• 58:52Speaker 05

  They are maybe doing it from memory, something they read, etc. 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?

• 59:04Barry Ritholtz?

  So you have a lot of interests. 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, where do you really focus your time and effort? What most interests you?

• 59:29Speaker 05

  So I'm gonna cop out and give you the answer. All of it interests me, Barry, or I wouldn't have it.

• 59:36Barry Ritholtz?

  True.

• 59:37Speaker 05

  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 hiring people with super high agency and who are really, really bright. ...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, I love books, I love media, I love podcasts, et cetera.

• 1:00:17Speaker 05

  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 1925, not 2025. 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 author's work sooner than they might otherwise. But also, because of the technology, we are able to offer a much better deal to our authors.

• 1:01:00Speaker 05

  Our authors typically will take 70% of the royalties

• 1:01:05Barry Ritholtz?

  Wow.

• 1:01:05Speaker 05

  after the costs have been cleared. So, we can still make a great deal of money at the 30% that we maintain. But there's also cross-pollinization, right? There's a great podcaster who is going to be a great author. There is a great author who might be a great podcaster. Or, we'll do the whole thing for them. We'll set them up on a Substack, 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 days of yore. A lot of great writing is there.

• 1:01:46Speaker 05

  And so, we want to be able to not only see that, but publish the best of it.

• 1:01:52Barry Ritholtz?

  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 doing cinematically.

• 1:02:14Speaker 05

  So cinematically, we started, our, 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, I, I mean, like, we are the rebel alliance, if you will, going up against some very, very tough competitors. So on the film side, we started with documentaries. 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.

• 1:02:57Speaker 05

  We are now commissioning documentaries with some younger talent that isn't really bound up by the way Hollywood currently does things.

• 1:03:07Barry Ritholtz?

  Meaning a little more nimble, light, fast, responsive.

• 1:03:12Speaker 05

  Much, much, much more nimble, much faster, much more responsive.

• 1:03:15Barry Ritholtz?

  Someone had shot a film on an iPhone, sort of as a little bit of a publicity stunt, I want to say eight or 10 years ago, but that's really very feasible today, isn't it?

• 1:03:28Speaker 05

  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 ridiculously boring? Color matching.

• 1:03:50Barry Ritholtz?

  Really?

• 1:03:51Speaker 05

  When, when things are filmed over a variety of days or locations or what have you, one day is cloudy, one day is sunny, you've got to have that match up so that your film appears of a piece.

• 1:04:05Barry Ritholtz?

  So it's more than just continuity.

• 1:04:07Speaker 05

  Absolutely.

• 1:04:08Barry Ritholtz?

  It's the next step beyond that.

• 1:04:09Speaker 05

  It's the next step beyond that. And there's just so much that can be done with, with the visual part, with the editing AIs that we have. Always gonna 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 take that hour or two hour and do the niggly, oh, I've got to move this to here and that to there. 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

• 1:04:51Speaker 05

  consuming, boring, and just like they take forever. And we can fix that to the point where they no longer take forever and the people we're 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.

• 1:05:18Barry Ritholtz?

  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 it sounds like you're finding this is just an incredibly useful tool and it's gonna make all of us more productive and more creative.

• 1:05:45Speaker 05

  Precisely. You know, we always get frightened when some new technology comes on the scene and, by the way, this goes back forever, like when-

• 1:05:54Barry Ritholtz?

  The Luddites, right?

• 1:05:55Speaker 05

  The Luddites, right? It goes back to Ned Ludd and who broke up all the machines because they were gonna take their jobs while he ended up working on one of those looms and he vastly preferred his new job because he didn't have to do it the old horrible way. Same thing's gonna 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 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

• 1:06:40Speaker 05

  out. I think, you know- AI is not going to take your job. A human being using the AI tools will. Because they are going to 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 AI, I subscribe to what they call the cenotar model. You remember the mythical beast?

• 1:07:14Barry Ritholtz?

  Sure.

• 1:07:15Speaker 05

  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 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 it well.

• 1:07:45Barry Ritholtz?

  Right, right.

• 1:07:45Speaker 05

  But I can guarantee you, almost all of that is going to be humans using AI as a tool 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.

• 1:08:06Barry Ritholtz?

  I like the way you 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.

• 1:08:18Speaker 05

  Exactly.

• 1:08:18Barry Ritholtz?

  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 tastemaker.

• 1:08:28Speaker 05

  We believe, passionately believe, that if you have good taste and you are a great curator, your future looks incredible.

• 1:08:38Barry Ritholtz?

  Really?

• 1:08:38Speaker 05

  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 next level of your good taste and curation.

• 1:08:51Barry Ritholtz?

  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 Award. Tell us a little bit about the support you offer for young entrepreneurs. What inspired you to start this program? I know we've had at least one O'Shaughnessy 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's it been running?

• 1:09:31Speaker 05

  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, I would give most of them fellowships.

• 1:09:49Barry Ritholtz?

  Hire them all.

• 1:09:50Speaker 05

  But, the real reason that I did it was because 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, 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

• 1:10:35Speaker 05

  to demonstrate what they have to offer to the world. 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 $100,000 over a one-year period to work on your project. If you're a grantee, you get $10,000. We have obviously many more grantees than we have fellows. But... Just 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.

• 1:11:17Speaker 05

  We have, we have, we have in-person meetings once a year. And the last one we had, I'll just give you a quick example. We, we have a scientist who is developing an in-home way to test your baby's 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, over 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

• 1:12:01Speaker 05

  changed the way I'm gonna bring this to market."

• 1:12:03Barry Ritholtz?

  Huh.

• 1:12:04Speaker 05

  So, the, the cross-pollinization and the synthesis of these great minds is really a thing to behold. I, I'm just very, very excited about what's coming out.

• 1:12:15Barry Ritholtz?

  And, and before we get to our favorite questions, I wanna throw you a curveball.

• 1:12:20Speaker 05

  Curveball.

• 1:12:21Barry Ritholtz?

  So, since we first met back in a CNBC green room in the early 2000s, so a few decades ago, you've had a fairly unique perch on the world of finance and investing and asset management. How has financial media and asset management changed over the course of your career?

• 1:12:46Speaker 05

  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 Mark Haines all the time.

• 1:13:00Barry Ritholtz?

  Sure, I've done that a few times.

• 1:13:01Speaker 05

  Back then, it was a three-hour program. In which the portfolio manager or the strategist that we were talking to was given like 20 minutes.

• 1:13:12Barry Ritholtz?

  I recall.

• 1:13:13Speaker 05

  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 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.

• 1:13:46Barry Ritholtz?

  Clearly.

• 1:13:46Speaker 05

  Have 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.

• 1:14:04Barry Ritholtz?

  Right, Patrick. Absolutely.

• 1:14:06Speaker 05

  Came in and filled the void. 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. They can, they can still watch financial media. Then there's the YouTube people.

• 1:14:29Barry Ritholtz?

  Right.

• 1:14:30Speaker 05

  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 it, how many shows have you done? You've, you have proof of work.

• 1:14:43Barry Ritholtz?

  I'll, I'll tell you a funny story. So, we're, July will be 11 years. It's 550 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. I was coming back from a conference in Vancouver, Canada, and I had to either change planes in Chicago or Montreal. I don't 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, there's no Twitter, they weren't doing a lot of TV. They're like, you really.

• 1:15:31Barry Ritholtz?

  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 20-minute hit.

• 1:15:42Speaker 05

  That's right.

• 1:15:43Barry Ritholtz?

  And when you have five minutes, it's what's your favorite stocks? When the Fed's gonna cut? Where's the Dow gonna be next year? Thanks for coming by. And the moment that guy walks out of the building, those answers are stale.

• 1:15:54Speaker 05

  Totally.

• 1:15:55Barry Ritholtz?

  So I was flying back after you changed planes. I bumped into a friend and I was kinda like grinding my teeth. And he's like, what's on your mind? You look like you're annoyed. And I relate the story. 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 are 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 top of my head.

• 1:16:31Speaker 05

  Sure.

• 1:16:31Barry Ritholtz?

  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 decades.

• 1:16:44Speaker 05

  Exactly.

• 1:16:45Barry Ritholtz?

  And 30 seconds doesn't, doesn't give you that. So on that note, let's, let's jump to our speed rounds.

• 1:16:52Speaker 05

  All right.

• 1:16:52Barry Ritholtz?

  And do our, 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.

• 1:17:00Speaker 05

  I hope I don't give the same answers.

• 1:17:01Barry Ritholtz?

  So, hey, listen, we'll have AI go through it and find out how your, how your thinking has evolved. Let's describe that.

• 1:17:07Speaker 05

  There we go. I love that.

• 1:17:08Barry Ritholtz?

  Right? So, um, starting with, what's keeping you entertained these days? What are you watching or listening to?

• 1:17:14Speaker 05

  So, uh, mostly listening to the normal group of podcasts that you would, yours, my son's, my own, uh, but, uh...

• 1:17:25Barry Ritholtz?

  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 wanna listen to somebody you're gonna interview and you don't want someone else's questions in your head?

• 1:17:39Speaker 05

  So, so my dirty little secret is that I very, uh, very seldomly listen to my own. I do read the transcripts.

• 1:17:47Barry Ritholtz?

  Right.

• 1:17:48Speaker 05

  Uh, just to make sure, ooh, I really screwed that up. I gotta fix that.

• 1:17:51Barry Ritholtz?

  Transcripts don't come across the same way as a spoken word.

• 1:17:54Speaker 05

  I know, I know, but I, I prefer to give my active listening time to like your podcast and, and Patrick's. Um, 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? Um, and I've started re- Made into a movie, right? Yeah, yeah. The book's much better than the movie. Someone else said that, yeah. Um, and, uh, I love Howard Bloom's work, uh, you know, the, he's- Closing of American Minds? No, no, different guy. Sounds like, right? Right. Howard is a very fun eccentric genius. Uh huh. Who's sort of started life as a scientist and now takes all of what he learned there

• 1:18:39Speaker 05

  and applies it to the social world or the business world. Closing of the American Mind? Or entertaining ourselves to death? No, no, one of his would be, uh, the Lucifer Principle. Oh, really? 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, Taming, uh, uh, Reimagining the Beast, uh, where he talks about capitalism. Huh. Saying, hey, 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.

• 1:19:21Speaker 05

  Um, read, uh, pretty much any paper I can get my hands on, uh, having to do with advances in AI, uh, and, and that sort of thing. Uh, for fun, I just saw the new Bob Dylan movie. Loved it. Mm-hmm. Um, and- A complete unknown. A complete unknown. And I also love the way Timothy Chalamet, the lead in that. Yep. I loved his speech when he got up and said, you know what? I could say, aw shucks, and I'm nothing, 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

• 1:20:04Speaker 05

  it's so, for so often, you know, we, we, you know, oh, wasn't really anything. Come on.

• 1:20:11Barry Ritholtz?

  False humility.

• 1:20:12Speaker 05

  False humility.

• 1:20:13Barry Ritholtz?

  It stands out, yeah.

• 1:20:15Speaker 05

  Doesn't it, right?

• 1:20:15Barry Ritholtz?

  It jars when you hear it.

• 1:20:16Speaker 05

  It jars when you hear it. And it's like, when I heard him give that speech, I'm like, right on. That's what I love hearing from a young actor or writer or whatever. Hey, I aspire to this.

• 1:20:29Barry Ritholtz?

  Don't we all aspire to greatness?

• 1:20:31Speaker 05

  I think so, right? We should.

• 1:20:32Barry Ritholtz?

  Like, you got one bite of the apple.

• 1:20:35Speaker 05

  You really do.

• 1:20:36Barry Ritholtz?

  Make it worth something.

• 1:20:37Speaker 05

  Make it worthwhile.

• 1:20:39Barry Ritholtz?

  Yeah.

• 1:20:39Speaker 05

  And so I was very happy to see that again, just for total fun. I love Billy Bob Thornton, so we really enjoyed Landman.

• 1:20:49Barry Ritholtz?

  You know, you're like the third or fourth person who told me how much they love that series.

• 1:20:53Speaker 05

  It is so much, it's just fun. And so you're probably not going to learn a lot by watching it, other than that Billy Bob Thornton chews up every scene that he appears in. He's such a good actor.

• 1:21:07Barry Ritholtz?

  Always is. Every time I see him in something.

• 1:21:09Speaker 05

  Me too, me too.

• 1:21:09Barry Ritholtz?

  He's a delight. You know, you have such an interesting background. I'm curious if you had any mentors help shape your career?

• 1:21:19Speaker 05

  I did. I had a gentleman who was, when I was very, very young. I'm not going to 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 filled with vinegar and very definitive beliefs. And I will tell you all, I'm going to proselytize. This is the way to do it. And he was really, really good at saying, ah, Jim, you might want to take that a step back. Because what do you really want? Well, I want people to know about this.

• 1:22:01Speaker 05

  Okay, but what's the broader implication here? Process over outcome. Okay, well, why don't 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.

• 1:22:26Speaker 05

  And always good at reminding me that you might want to take it back a notch or two.

• 1:22:33Barry Ritholtz?

  That's great. Let's, um, you mentioned a few books. Any other favorites you want to mention before we get to our favorite questions?

• 1:22:41Speaker 05

  The, the, what, let me reference our infinite books. We have a list that you can get anywhere. It's, 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 it's a masterpiece.

• 1:23:00Barry Ritholtz?

  Beginning of Infinity.

• 1:23:01Speaker 05

  By David Deutsch, who's a quantum physicist in the UK. I love all of his work, but I also think people should be reading things like, my perennially read The Tao Te Ching by Lao Tzu. It packs a wallop, man, because you can read the whole thing in an hour.

• 1:23:21Barry Ritholtz?

  Right.

• 1:23:21Speaker 05

  But I used to joke, you know, I started reading that when I was 18, and I read it every year, sometimes multiple times every year, and I finally started to understand it when I was about 55.

• 1:23:31Barry Ritholtz?

  Right. I was gonna say, it's a different book each time you read it.

• 1:23:34Speaker 05

  It really is. It's like Heraklitus, you know, no man steps in the same river twice because it's not the same man and it's not the same river.

• 1:23:43Barry Ritholtz?

  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?

• 1:24:00Speaker 05

  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 use of those tools, and if you walk into a job interview with some mastery of them, what they're doing in terms of what they can uncover for like VC, for traditional long-only or long-short management, is staggering.

• 1:24:39Speaker 05

  Get a deep domain knowledge there as it fits into your particular passion, be it investing or analysis, et cetera. But that would be my number one piece of advice.

• 1:24:53Barry Ritholtz?

  Wow. And our final question. What do you know about the world of investing today that would have been helpful back in the 1990s when you were first starting out?

• 1:25:03Speaker 05

  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 1987. I went through the other bear markets. But I didn't really lock in on the fact that markets change millisecond by millisecond. Human behavior barely budges millennia by millennia. Arbitraging human nature is the final mote.

• 1:25:42Barry Ritholtz?

  Arbitraging human nature is the final mote. 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. I remember, I want to say it was like the late 2000s, sitting at an outdoor on a Starbucks.

• 1:26:11Speaker 05

  Yep.

• 1:26:12Barry Ritholtz?

  In Park Avenue.

• 1:26:13Speaker 05

  I remember it well.

• 1:26:14Barry Ritholtz?

  Hey, 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 people you've had such a positive impact on. It's just a delight and a pleasure to know you.

• 1:26:37Speaker 05

  Well, right back at you, Barry. I, it's been my great pleasure knowing you all of these years.

• 1:26:44Barry Ritholtz?

  So, so this mutual admiration society has to come to an end?

• 1:26:48Speaker 05

  It's a bromance.

• 1:26:51Barry Ritholtz?

  We have been speaking with Jim O'Shaughnessy, founder and CEO of O'Shaughnessy Ventures. If you enjoy this conversation, well, check out any of the 500 previous ones we've had over the past 10, almost 11 years. You can find those at iTunes, Spotify, YouTube, Bloomberg, or wherever you find your favorite podcasts. 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 18, 2025. I would be remiss if I did not thank the crack team that helps put these conversations together. Anna Luke is my producer.

• 1:27:36Barry Ritholtz?

  Meredith Frank is my audio engineer. Sage Baumann is the head of podcasts at Bloomberg. Sean Russo is my researcher. I'm Barry Ritholtz. You've been listening to Masters in Business on Bloomberg Radio.

• 1:28:07Speaker 01

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