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Conor Boyle
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Bill Browder
I'm NFL linebacker TJ Watt and this.
Robert Rosenkrantz
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Conor Boyle
Welcome to Intelligence Squared where great minds meet. I'm Head of Programming Conor Boyle. Today's episode is with businessman and philanthropist Robert Rosencrantz. Rosencrantz joined us to discuss the themes of his new book the Stoic Capitalist in conversation with fellow businessman and author Bill Browder. Let's join Bill now with more.
Bill Browder
Hello, I'm Bill Browder. I am here to interview for Intelligence Squared Robert Rosenkrantz, my friend and we're here to talk about his book the Stoic Capitalist. This is a great book. I've read it twice in fact I had a chance to read it in process and I had then a chance to read it as it was polished up and I would say that this book is kind of like a rorschach test in that each person who reads it sees a different book. On one hand, this book is about it's sort of a how to book, how to become successful. On another hand, it's a book about sort of philosophy of life. On the other hand, it's a book about all different subjects and Robert's view on the world. And so I wanted to delve into all these things. But to start out with, I want to just define for the audience who you are. You are the CEO of and I guess owner of, of Delphi Insurance, which is a very large insurance company.
Robert Rosenkrantz
Well, I was the owner. I did sell it a few years ago.
Bill Browder
Even better. So you can do all these other great things that we're going to talk about. When we were discussing what you should call this book, I thought that this is the subtitle of this book, which wasn't actually done here, is the most successful person on Wall street you haven't ever heard of. And part of the reason you haven't heard of you is that you're a modest man. You're not announcing yourself to the world. But I'm hoping that we can sort of break through some of that modesty and get to some of the unbelievable stories in the book. But before we get to all the big Wall street success, I want to just start a little bit so people can get to know you. With your personal background, where do you come from? You didn't come from blue blood successful family. You came from something else. And that was one of the things that struck me first when I read the book. And maybe we could talk a little bit about your family and your upbringing and sort of what drove you to become successful.
Robert Rosenkrantz
Well, Bill, thank you very much. And you've been a big part of bringing this book to where it is today, including suggesting the title the Stoic Capitalist. I think it was the Stoic Financier when you saw it. And this is a huge improvement. So thank you. And it's a particular pleasure to be at an Intelligence Squared podcast, because I've been involved with intelligence squared for 20 years, and it's had a transformative effect on my life and I think the lives of many people who've listened to what we've done with this program in America, which is now rechristened Open to Debate. In any event, going back to your question about my childhood, it was a difficult childhood in many ways. My parents were incredibly insecure financially. My mother was a clerk in a drugstore. My father was unemployed when I was seven years old. And they did not hide from me any of their financial insecurities. They were worried about the lights being cut off or the gas being cut off or the telephone being cut off. And that's what I kind of grew up with. But for me, that became a kind of, you know, there's a stoic idea the obstacle is the way. And that circumstance, which many people would find an obstacle to me was a stimulus, almost required me to take full responsibility for my own life. And that became a vital principle. Another quote obstacle was that my parents really had some pretty bad ideas. My mother was a communist. I don't know if she was a member of the party, but she certainly believed all that. And she was quoting Karl Marx continuously. And the philosophy didn't sound right, right to me. And she was also emotionally off the rails a lot. So again, what do you do with an obstacle like that? Well, what I did was critical thinking, subjecting what my parents had to say, which clearly wasn't working out for them very well, to critical thought. And that became a success factor and then a kind of distrust of emotions. And that also the idea of privileging rationality over emotions became a critical success factor for me in life as well.
Bill Browder
So then you went to Yale, and I guess Yale wasn't taking a lot of lower middle class or lower class Jewish boys from the Upper west side. What was that like at Yale?
Robert Rosenkrantz
Well, I do want to tell a story before I got to you, I started my schooling in public school, first grade. And I had a first grade teacher who thought I was particularly able and urged my parents to enroll me in a private school because she didn't think I'd be challenged enough in public schools or what in Britain you'd call state schools. And my parents said, well, thank you, but there's absolutely no way we can afford school fees. And this teacher took it on herself to get me IQ tests, to get me admitted to a private day school, to get me a full tuition scholarship, and announced all of this as a kind of a feta complete of my parents. I raced through that school. So I was the youngest kid in my class at Yale and I graduated when I was 19. So Yale was a terrific place for me academically. I really liked it a lot. And by excelling there, it really gave me the confidence to feel like I could compete in a much larger environment than the relatively narrow world that I grew up in. But it was awkward as a younger kid from a very different background than the typical Yale student of the day.
Bill Browder
Because back then it wasn't like it is today, with culturally diverse and economically diverse student body. This was really sort of the upper crust of America. Unless you were well to do, you kind of didn't end up at Yale, right?
Robert Rosenkrantz
Well, there was sort of two Yales in my day. About half the kids were legacies from maybe 20 great prep schools, and they came from, you know, this corridor from Boston to maybe Philadelphia. And that was sort of half of Yale. The other half were sort of valedictorians from high schools all around the country. They were more Jewish, more Irish, more Italian. They were much brighter than the first half. But that didn't count for much in Yale's pecking order.
Bill Browder
And you did take a math class from a very famous American mathematics professor.
Robert Rosenkrantz
I did. And his name was Browder, and I believe he was your dad.
Bill Browder
That's right.
Robert Rosenkrantz
And he was. He was actually a young superstar. He was teaching. He taught my honors calculus course. I think he was in his late 20s at the time, and he had.
Bill Browder
A very important message for you. Maybe we could talk about that for a second, because I think this is crucial, where our paths collided and had something to do with your subsequent success.
Robert Rosenkrantz
Well, I did consider majoring in mathematics, and I asked your dad about it, and he sort of gently suggested that maybe economics would be a better idea for me. And he was absolutely right, because the qualities that it took to really excel in mathematics just was a level of ability that I didn't have. And economics turned out to be an absolute natural for me. It came very easily. I was really fascinated by the kinds of questions the discipline was asking, and I had a flair for the theory and the logic behind the answers. And so that education, combined with then subsequently Harvard Law School, really stood me in very good stead.
Bill Browder
I would argue that he did you an unbelievable economic favor. Having grown up in a family of mathematicians, I can tell you that you're probably like a thousand times better off than you would have if you had followed them. So he may not have felt like at the time when he was pushing you away from math, but you really hit the ball out of the park by following.
Robert Rosenkrantz
Yes, it was great advice, and I thank you. I thank him and I thank you. By inference, we don't have time to.
Bill Browder
Go through every different stage of your career, but. So you went to law school and you didn't become a lawyer. You ended up working in finance and you worked at Oppenheimer. And there's a great story in your book, and there's a bunch of great stories in the book, but I'm going to focus on the few that are the ones that really jumped out at me. And there's a story about how you were in Oppenheimer, which wasn't the best of all the investment banks. And you weren't in the best part of Oppenheimer, but you figured out an arbitrage. And the arbitrage was, if I'm not mistaken, in the silver market. And I really love this story. Maybe you could tell this story to our listeners.
Robert Rosenkrantz
Well, it was really like a multidimensional arbitrage in a way. I had written my honors thesis at Yale on covered interest arbitrage, which is a way of arbitraging interest rates between two different markets. And as a tax law, I did actually practice law for two years as a tax lawyer. So I was quite familiar with the income tax code. And there was kind of an arbitrage between ordinary income and capital gains and an arbitrage between the relationship of the silver price on two different points in time versus the interest rates, the value of money over those points in time. And I was able to put all of that together in a way that created a nice profit for the firm, around 5% of its profit pre tax, but on an after tax basis increased their after tax income by like 45%.
Bill Browder
So how old were you then? At the time?
Robert Rosenkrantz
I was about 26, I want to say.
Bill Browder
So a 26 year old guy comes in, sort of a nobody comes in, and on an after tax basis generates like half the firm's profits. Would that be a fair. I guess it is fair, a fair description.
Robert Rosenkrantz
But the book goes on to make an interesting point about this, which is that the senior partner in the firm, Leon Levy, who was my mentor and an incredibly valuable person to have known so early in my career, came into my office to congratulate me on the steel and say what an important contribution it made to the firm. And I had this weird thought which was like, where is it written? And I'm running a race and he's standing at the finish line handing out the prizes. So even at that young age, I wasn't looking for him to give me approval. I wasn't looking for his esteem. I knew that this was an important contribution. I knew it was something other people wouldn't do. But I wasn't thinking about how to get a promotion or how to be a partner in the firm. I was thinking, how do you get to be Leon Levy? How do you get to own a firm like this? And that kind of outsized ambition coupled with A kind of a rational self esteem was really a very key success factor for me. And the book develops a lot of the ideas that I think would help other people kind of grasp and realize some childhood dreams that may seem way, way out of scale with where they're starting from.
Bill Browder
And needless to say, at that moment in time, even though you made the firm half their profits, that wasn't the moment that you got financially rewarded in any kind of spectacular way. It was, you were just like, you know, maybe given a good bonus and thank you very much. But the next story in your book, which really made an impression on me anyways, was how you transition from being an employee to being your own boss by starting your own firm. And the book starts with this meeting with a guy named Mailman. Mailman. That name doesn't mean anything to us now. It was probably a big name back in the day. His name was on hospitals and schools and so on. And the reason why this story, which you're going to hopefully tell us in a second, impressed me so much, was that this was the very dawn of the private equity industry, of the LBO leveraged buyout industry. And you go to meet with this guy to have some important meetings at the Pierre Hotel. You're a young guy, you have big ambitions, and you go there to discuss how he and you could be partners in a business to buy companies. And it would be great for you to share how he or you together turn the model of private equity on its head. What was everyone else doing and what did you guys decide to do and why was that interesting?
Robert Rosenkrantz
It was definitely the most courageous business judgment or decision I've made in my life. I was about 35 years old. I had done one successful buyout transaction of a company called Big Bear Stores, in which Joe Mailman was the major investor. It worked out very, very well for him and. But he wasn't happy because he felt like he had put up most of the money, I had done most of the work, and Oppenheimer got most of the rewards. So he was proposing to basically, with a group of friends, give me the capital to start a firm of my own. And the way the typical structure in those days, which persists to these days, is what's called a carried interest, where the guy who does the work, the general partner, gets 20% of the upside as his recompense for doing it. And Joe pushed back against that. He said, well, it sort of puts you in a heads, you win, tails I lose position. It gives you incentive to take excessive risk. I Said, Joe, you know, you're right. And I made a proposal that astonished him. I said, I've accumulated about $400,000 in liquid assets.
Bill Browder
What would that be in Today's money?
Robert Rosenkrantz
About $4 million in today's money money. And I said, I'll put every penny of it up, and I don't want to carry an interest at all. I'll absorb 50% of all the losses out of my $400,000, and I want 50% of the gains now. What that meant was that a 20% loss of the firm's capital would have wiped me out entirely. And he thought it reflected an extraordinary self confidence on my part, a lot of courage. And he agreed to those terms. Well, the first deal we lost $100,000. The second one we made 100 million. So it kind of averaged out.
Bill Browder
Let's not jump too fast over the 100 million, because that's another story that really, again, in my Rorschach test here, I love the stories of deals. And the deal that you just described is called the Old Fort deal. And I would love for you to explain how you turned it was like some small number of millions of dollars into $100 million. And again, $100 million back then is a lot different than $100 million.
Robert Rosenkrantz
Yeah, no, inflation is roughly 10x.
Bill Browder
You made a billion dollars in today's money.
Robert Rosenkrantz
Exactly. Yes, I guess I did. And the way we did it was.
Bill Browder
Basically what was Old Fort.
Robert Rosenkrantz
Okay, so Oldfort was a random group of companies. It had garbage dumps, it had concrete block making companies, it had stone quarries. But it had one business that I really liked, which was the lawn and garden business. It was the largest packager of organic gardening materials. Peat, humus, topsoils, potting soils and the like. And I really liked that business, first of all, because it was, I thought, recession proof. It was benefiting from social trend away from chemicals and toward organics. And I had a kind of a roadmap that was given to me by the founder's son of how to sell off the bits that I wasn't interested in and end up with the lawn and garden business.
Bill Browder
Why did the founder. Why did the founder's son tell you about this? And why were they actually. Let's back up.
Robert Rosenkrantz
Okay.
Bill Browder
How much were they selling the business for?
Robert Rosenkrantz
I bought the business for around $18 million. We put up a million and a half dollars in cash, borrowed the rest.
Bill Browder
A million and a half dollars in cash. And so somebody lent you like 90% of the value of the business. Yep.
Robert Rosenkrantz
And that was not atypical in those early days of leverage buyouts. You could borrow 90%, so you put.
Bill Browder
Up a $1.5 million, the rest of the money. And then you could. But why would they. And then. And why was the seller's son telling you that you could sell off pieces of it, which would obviously bring you back your $18 million or whatever.
Robert Rosenkrantz
It wasn't so obvious, but it did.
Bill Browder
But why did he want to do that?
Robert Rosenkrantz
Okay, so he was the black sheep of this family. His father was this ramrod, straight German Catholic guy in Fort Wayne, Indiana. The son was a kind of hard drinking womanizer, was banished to run some minor subsidiary in Denver. And what particularly galled the father was that the son was a better businessman. So he made a fortune in oil, and he made another fortune in banking in Colorado. And he knew his relationship with his father was much too fraught to ever buy this company himself. And he and I were on the board of company and the oil business together. And he just threw the opportunity to me. But this was a very early example of what's now called an industry consolidation play. So we sold off all the bits we didn't like.
Bill Browder
And how much did you get for the bits you didn't like?
Robert Rosenkrantz
Basically enough to pay off all the debt.
Bill Browder
So you bought it for 18 million, you put a million and a half in, you bought it for 18 million, you sold off a bunch of stuff, you get back all 18 million. So at that point, you're 18.
Robert Rosenkrantz
So at that point, I own this company free and clear. It's making about 5 million a year by that point, which again, like $50 million a year in today's money. And the business, although was the largest in the country, you couldn't ship this product very far. So it was sort of like a regional monopoly. And I used the money that I was making from that, plus the proceeds of initial public offering buy up companies all around the country. So we became the 1 national supplier of this product. And if Kmart wants to run a sale or any major national garden chain, we were the only people they could deal with.
Bill Browder
So you've got this business, you roll up some other stuff, you go from 5 million to some other million of earnings, and then you sell it for 100 million. So you put up 1.5 million, you sell it for 100 million. Now you've got real money.
Robert Rosenkrantz
Exactly.
Bill Browder
And with real money, what was your next big play?
Robert Rosenkrantz
Well, my next big play really was by that point, the leveraged buyout business had sort of changed. People were twigging to it, realizing that it could be a very lucrative activity. And so capital was flooding into it. People were starting big institutional pools of capital and, and the prices were going higher for buying companies. The amount of equity you needed was substantially more, the potential returns much less. And I then pivoted to the idea of buying a company where I could really make a big difference in the, in the earning power of the business. And that was the purchase of an insurance company which ultimately became Delphi. We invested $20 million in that, ultimately, many years later, sold it for about $3 billion. And that was my principal asset.
Bill Browder
This is like alchemy. One and a half to 120 million to 3 billion. It's really a hugely impressive business.
Robert Rosenkrantz
But what I want to come back to though is yes, the business success was substantial, but what the book is about is not really. I mean, it talks about some of the principles that helped me do this. Principles of rationality, principles of controlling emotion, principles of allocating time, principles of interviewing people and how to build a quality organization, how to motivate people, how to negotiate. There are a lot of skills along the way that the book explains and it explains it in ways that I think could be applied to people not just trying to pursue ambitious financial careers, but any ambitious careers running any kind of company, any kind of enterprise, any kind of activity where success is going to be a matter of long term commitment.
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Bill Browder
Well, there's one great story within your Delphi thing which I want to which comes to some of these other issues, which is you talk about you have this large pool of capital and you have to allocate it to different managers and but somehow you had a nose for so everyone was throwing their money at Bernie Madoff back in the day and he had the consistent returns every month. And one of the stories I love here is as you were interviewing money managers, you somehow sniffed out that he was a fraud when nobody else did. How do you sniff out frauds? How do you find dishonesty? How do you understand whose fraud forthright and who's not? Because, as you say, that applies not just in investments. That applies in every other aspect of life.
Robert Rosenkrantz
It was actually relatively easy in the Madoff case, and it was odd to me that so many other professional investors didn't do what I did. And the thing that made it particularly easy was he was operating as, quote, managed accounts, which means if you had money with Madoff, you got confirmation slips of every trade. Friend of mine shared with me three months of trading, and I pulled a couple of these confirmation slips at random, and I saw that every purchase was at the high at the low of the day, every sale at the high of the day. Nobody can trade like that. And then my friend was like 1% of the total. So multiply by 100. There wasn't that much volume traded. So it was just clear to me that this was a flurry of confirmation slips. But the point is, it took me about 15 minutes to do this, and any professional investor could have done it, and they didn't.
Bill Browder
But so there was nothing. So it wasn't like in a meeting, you looked him in the eye and he was twitching his tweets.
Robert Rosenkrantz
I never even met him, to be honest.
Bill Browder
Yeah, never even met him. Interesting. Interesting. Well, it's really something because everybody else got sucked into that mess.
Robert Rosenkrantz
And, well, Mark Twain has famous quote, it's easier to fool people than to convince them that they've been fooled.
Bill Browder
All right, we've talked a lot about business, but you're not just a businessman. You've done a lot of other things. And let's sort of broaden the conversation. One of the things which I've seen, which I find fascinating, is your passion for art. And again, you haven't followed the traditional path of an art collector, of an art connoisseur. You've kind of broken into, just like you did with private equity, setting up a new model. You've broken into a new area of art that nobody else is doing. Let's talk about some of the things you're doing in the art world.
Robert Rosenkrantz
Well, my current passion in the art world, and it's been a very serious interest of mine for decade, is art that uses. That's video art, art that uses technology, art where the artists are trying to create immersive experiences. And it struck me that it's the natural language for younger people. They get all their information from screens. They do all their communicating on devices. So it was their natural form of expression. And there was huge amounts of creativity that was stimulated by all of the technological progress. So I really got very interested in it. It's a hard area to collect in because you need a lot of technological sophistication. The top collectors have dedicated spaces to show this. So it's mostly museums, only a handful really of collectors. But one of the things I talk about in the book as an ingredient of the well lived life is using your financial resources, if you've been able to accumulate them in ways that benefit society, and creating the kinds of institutions you think that the society can use. Which was sort of, to me a heroic form of philanthropy that people like Carnegie and Rockefeller practiced. And on my own little, much more modest scale, I'm trying to do something like that field of video art. And I bought a venue on the Lower east side of Manhattan. We're calling it Canyon. I hope to open in the next year or so and have a dedicated space so that people can engage in this kind of art in ways that museums just find it difficult to support.
Bill Browder
Well, I'm very much looking forward to the opening, so I can participate as well. You're also involved in philanthropy and particularly science and longevity. And you've just mentioned to me before we started this that you've just returned from a big conference on longevity in Saudi Arabia. And I think that it's all very interesting, your view on longevity, how you're involved and what kinds of things are you up to that would make people live longer, make you live longer, maybe make me live longer.
Robert Rosenkrantz
Well, the next to the last chapter in the book is called you Can Make More Money, you Can't Make More Time. The final chapter is called maybe youe Can Make More Time. And again, this is kind of an application of some stoic principles. It's the idea that time is our most precious resource. And particularly the time when we're in good health and can enjoy life to the fullest. And most people recognize that, but they don't necessarily take on board that their health spans are a matter of their own decision making. They sometimes think it's just genetics or just luck. We kind of know that eating well and that exercise are good for us and will prolong the period that we're healthy before we get the diseases of old age. But it takes certain discipline to do that. It takes a certain mindfulness. And if you're beset by emotional problems, if you're completely stressed out, if you're angry, if you're not of clear and calm mind, it's very hard to have the discipline that it takes to do the things that everybody knows are worthwhile. But turning more to the science, most of the resources that we devote to medical research are curing specific diseases. And practically no resources in relative terms are devoted to understanding why we age in the first instance, what's going on with our cells at a molecular level that makes them over time become vulnerable to disease. And, and that's the project that I'm really excited about. Lifespans don't interest me very much, but health spans do. The period where we're in really good health and if we can create 10 or 15 years of extended good health for people, that to me is the greatest gift that science can give human flourishing and an absolutely worthy philanthropic goal.
Bill Browder
And you have been very generous in this area. I think we should talk about that. Let's not hide it.
Robert Rosenkrantz
Well, the money is one thing, but it's really thinking about how to go about it. So one of the projects, and the one I'm probably proudest of is called Impetus Grants. And they're like NIH grants to scientists in laboratories working on longevity projects. But, but unlike the NIH, it's two page application rather than 100, it's three weeks to decide rather than nine months. And it's absolutely tolerant of, embraces risk, provided that if the thing works out, it really moves the field forward. We had over 1,000 applications, we gave 35 grants and it's only a year, but there are already some very promising results.
Bill Browder
And among those 35 grants, what's the one that excites you the most right now?
Robert Rosenkrantz
Well, this is a little odd, but a lot of longevity experiments were done with a kind of worm called C. Elegans, which has a natural lifespan of 15 days. And the reason they do it is because you get very quick results. We backed a project to see if we could get this worm to live for a year. Well, a year hasn't gone by. Only 250 days have gone by, but 65% of them are still alive. So 17x extension of lifespan, the biggest by far that's ever been achieved.
Bill Browder
I'm going to take whatever they're taking. What is it that you're doing with the worms?
Robert Rosenkrantz
Well, because these worms are so easy to experiment on, there have been dozens and dozens of interventions that have proven helpful. This investigator decided to use them all, just throw absolutely everything against it and see if it had a cumulative effect. And it seems to be doing it. So there's a guy who's actually doing this called Brian Johnson who's doing absolutely everything. So he's like the human C. Elegant Swarm.
Bill Browder
Yeah, no, but I've seen him. I've seen him. I don't want to look like him. He's like blue, you know, that's not. Well, we're almost out of time here. And so let's just finish off by talking about. I mean, there's so much advice in this book and so much valuable advice. If you could distill to two or three things, advice you would give a young person who's sitting in university somewhere in the world and looks at your life and says, that's really cool, what this guy has achieved, what advice would you give them? Two or three things that. If you had to distill it. And there's like 100 things in this book, but two or three things to be successful, to have a good life, to live a life of meaning.
Robert Rosenkrantz
Well, I would say it's really the application of a number of these stoic principles. It's the idea of really using reason to control emotion, really being thoughtful about your time. It's the idea of focusing on the things that really matter and doing them with intensity and not getting distracted about things that don't really matter. And there are techniques in the book for how do you distinguish between an opportunity that's really worth pursuing and one that's merely distracting? And so those are, I'd say, some of the key ideas that I would say in terms of what a young person needs to do to succeed. But the biggest idea, really, would be to find something in life that engages all of their creativity, all of their energy, all of their faculties. Because in the final analysis, you're going to be competing with people who enjoy what they're doing. If it's work for you, it probably is not going to succeed at the same level as if it's play, if it's fun, if it's stimulating, if it's interesting. And so I think you really have to find something that gives you that sense of satisfaction, that you can be fully committed and energized by it.
Bill Browder
Good answer. Robert Rosenkrantz, author of the Stoic Capitalist. Thank you very much for a great conversation, and I urge everybody to go out, buy and read this book.
Robert Rosenkrantz
Well, thank you very, very much, Bill. Real pleasure.
Conor Boyle
Thanks for listening to Intelligence Squared. This episode was produced by myself, Connor Boyle, with production and editing by Mark Roberts.
Bill Browder
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Host: Conor Boyle
Guests: Robert Rosenkranz (businessman, philanthropist, author of The Stoic Capitalist), Bill Browder (financier, author)
Date: May 10, 2025
In this compelling episode, Bill Browder interviews Robert Rosenkranz about his new book, The Stoic Capitalist, exploring how Stoic philosophy intersects with the worlds of business and capitalism. The conversation traverses Rosenkranz’s humble background, his meteoric rise in finance, principles of rationality in decision-making, his approach to philanthropy and longevity, and how Stoic ideas can help guide young people and leaders to a meaningful and successful life.
[03:44–07:32]
Rosenkranz grew up in a financially insecure household:
“That circumstance, which many people would find an obstacle, to me was a stimulus, almost required me to take full responsibility for my own life.” (Rosenkranz, 05:34)
Early demonstration of critical thinking and rationality:
[07:32–14:15]
Entered Yale on a scholarship after an elementary school teacher championed his abilities.
Found Yale to be a culture shock socially, but academically empowering.
Considered mathematics but was gently redirected to economics by Professor Browder (Bill’s father).
"He sort of gently suggested that maybe economics would be a better idea for me. And he was absolutely right, because the qualities that it took to really excel in mathematics just was a level of ability that I didn't have.” (Rosenkranz, 10:39)
Legal career quickly segued into finance. Early at Oppenheimer, he combined arbitrage and tax law knowledge to generate major profits for the firm, without seeking external validation.
“Even at that young age, I wasn’t looking for him to give me approval... I was thinking, how do you get to be Leon Levy? How do you get to own a firm like this?” (Rosenkranz, 14:15)
[15:47–25:26]
Pivotal moment: Chose to structure his own private equity deals with unusually high personal risk, declining the typical “carried interest” fee.
“I said, I'll put every penny of it up, and I don't want to carry an interest at all. I'll absorb 50% of all the losses out of my $400,000, and I want 50% of the gains.” (Rosenkranz, 18:18)
Detailed breakdown of the Oldfort deal:
“So at that point, I own this company free and clear... I used the money that I was making from that, plus the proceeds of initial public offering, to buy up companies all around the country.” (Rosenkranz, 23:02)
Next, purchased Delphi Insurance: $20 million investment, sold years later for $3 billion.
[25:26–29:27]
Discussion shifts from anecdotes to the deeper lessons in his book:
Notably, he avoided the infamous Madoff scandal by applying simple, rational checks rather than following the crowd.
“I saw that every purchase was at the low of the day, every sale at the high of the day. Nobody can trade like that... it took me about 15 minutes to do this, and any professional investor could have done it, and they didn’t.” (Rosenkranz, 30:17)
[31:39–34:20]
“One of the things I talk about in the book as an ingredient of the well lived life is using your financial resources... in ways that benefit society and creating the kinds of institutions you think that the society can use.” (Rosenkranz, 33:03)
[34:20–39:01]
Interested in extending healthspan rather than lifespan.
“Most people recognize that [time is our most precious resource], but they don’t necessarily take on board that their health spans are a matter of their own decision making.” (Rosenkranz, 35:16)
Describes his support for innovative “Impetus Grants” for longevity research—risk-tolerant, fast, and flexible grantmaking.
[39:35–42:01]
“You really have to find something that gives you that sense of satisfaction, that you can be fully committed and energized by it.” (Rosenkranz, 41:39)
On Overcoming Adversity:
“That circumstance, which many people would find an obstacle, to me was a stimulus, almost required me to take full responsibility for my own life.” (Rosenkranz, 05:34)
On Rationality Over Emotion:
“The idea of privileging rationality over emotions became a critical success factor for me in life as well.” (Rosenkranz, 06:48)
On Career Advice from a Mentor:
“He sort of gently suggested that maybe economics would be a better idea for me. And he was absolutely right.” (Rosenkranz, 10:39)
On Self-Esteem and Ambition:
“I was thinking, how do you get to be Leon Levy? How do you get to own a firm like this? And that kind of outsized ambition coupled with A kind of a rational self esteem was really a very key success factor for me.” (Rosenkranz, 14:15)
On Risk and Integrity in Business:
“I'll put every penny of it up, and I don't want to carry an interest at all. I'll absorb 50% of all the losses out of my $400,000, and I want 50% of the gains.” (Rosenkranz, 18:18)
On Avoiding Investment Fads:
“I saw that every purchase was at the low of the day, every sale at the high of the day. Nobody can trade like that... it took me about 15 minutes to do this, and any professional investor could have done it, and they didn’t.” (Rosenkranz, 30:17)
On Philanthropy and Living Well:
“...using your financial resources, if you’ve been able to accumulate them, in ways that benefit society and creating the kinds of institutions you think that the society can use.” (Rosenkranz, 33:03)
On Purpose and Fulfillment:
“You really have to find something that gives you that sense of satisfaction, that you can be fully committed and energized by it.” (Rosenkranz, 41:39)
The conversation is candid, intellectually rich, and punctuated by humor and humility. Rosenkranz’s measured, thoughtful responses reflect his commitment to rationality and mindful living, in line with Stoic philosophy. Browder’s probing questions draw out practical lessons and memorable stories, making abstract concepts highly relatable.
This episode is an engaging deep-dive into how ancient Stoic principles can inform not just personal well-being but also groundbreaking business and philanthropic achievements. Rosenkranz illustrates both with vivid anecdotes and distilled wisdom, showing that controlling emotions, rigorously applying logic, and keeping one’s time and purpose in clear focus are keys not just to financial success but to living a meaningful life.