We Study Billionaires - The Investor’s Podcast Network - RWH064: A Soulful Path To Stellar Returns w/ Nima Shayegh

Episode Date: December 21, 2025

William Green talks with Nima Shayegh of Rumi Partners about Lou Simpson’s investing wisdom and the power of ignoring noise to achieve outstanding returns. IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:06:41 - How Nima Shayegh came to see investing as the ultimate intellectual adventure. 00:10:31 - Why investors must go beyond numbers to grasp deep truths about businesses. 00:16:56 - What riding in a Tesla taught him about the awesome experience of quality. 00:21:05 - Why investors should harness intuition & emotions but avoid ego. 00:36:31 - How to succeed by owning resilient businesses & ignoring macro forecasts. 00:39:26 - What qualities made Nima’s mentor, Lou Simpson, an investing legend. 00:49:27 - How Lou taught Nima to avoid noise, distractions & the lure of a flashy office. 00:59:03 - Why Nima’s portfolio is dominated by stocks like AppFolio & Brookfield. 01:13:08 - What he learned from having dinner with Charlie Munger. 01:30:26 - Why we should surrender to uncertainty & should welcome volatility. 01:39:55 - What investors can learn from surfers about the value of self-reliance. 01:41:35 - Why he named his investment firm after a 13th-century Sufi mystic. Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Join the exclusive ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Inquire about William Green’s ⁠⁠⁠⁠Richer, Wiser, Happier Masterclass⁠⁠⁠⁠. Read Concentrated Investing by Allen Benello, Michael van Biema, Tobias Carlisle. Read Small is Beautiful & A Guide for the Perplexed by E.F. Schumacher. Read Jalal ad-Din Muhammad ar-Rumi’s book, The Ultimate Rumi Collection. Check out William Finnegan’s book Barbarian Days. Check out William Green’s book, Richer, Wiser, Happier. Follow William Green on ⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠. Related ⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast. Ad-free episodes on our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Premium Feed⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. NEW TO THE SHOW? Get smarter about valuing businesses in just a few minutes each week through our newsletter, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Intrinsic Value Newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Check out our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠We Study Billionaires Starter Packs⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Follow our official social media accounts: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X (Twitter)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Browse through all our episodes (complete with transcripts) ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Try our tool for picking stock winners and managing our portfolios: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Finance Tool⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Enjoy exclusive perks from our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠favorite Apps and Services⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn how to better start, manage, and grow your business with the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠best business podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. SPONSORS Support our free podcast by supporting our sponsors: Simple Mining Linkedin Talent Solutions HardBlock Alexa+ Unchained Amazon Ads Vanta Shopify Abundant Mines Horizon Public.com - see the full disclaimer here. Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

You're listening to TIP. Hi, folks, it's a great pleasure to be back with you on the richer, wiser, happier podcast. The conversation you're about to hear was a total joy for me. My guest is a high-flying young hedge fund manager named Nima Chay, who's one of the most talented and thoughtful investors I've met in recent years. In some ways, this episode is an unusual one. For one thing, Nima is still in his 30s, which makes him possibly the youngest fund manager I featured on.

the podcast. Also, as you know, I've tended to interview a lot of investors who are already very well known, people like Howard Marks, Ray Dalio, Bill Miller, Terry Smith, Rick Reader, Chris Davis, and the like. By contrast, Nima has flown almost entirely under the radar. As far as I'm aware, this is the first extensive, wide-ranging interview that he's ever given. Nima runs a relatively small hedge fund called Rumi Partners, which is named after the 30 century Persian poet and mystic Rumi. He works on his own in California, managing money for a fairly small group of wealthy, limited partners. He's not really focused on marketing or gathering a huge amount of assets. Rather, I would say he follows in the tradition of investors like Nick Sleep and

K. Sakaria, who really were devoted entirely to the essential challenge of generating superb long-term returns. Nemer, much like them, does it by investing in a very concentrated portfolio, in his case, fewer than 10 stocks. His approach to investing also owes a great deal to his mentor, the late great Lou Simpson, who was one of the most successful stock pickers of all time. Nima spent several years working for Lou, who was hailed by Warren Buffett as one of the investment greats. In today's episode, you'll hear a lot about what Nima learned from Lou about the art of long-term investing. I think you'll soon see why I'm so impressed with Nima and why I regard him as one of the rising stars of the investment world. He's not just an excellent stock picker,

but also a really interesting thinker. And I regard him as unusually wise and prematurely wise, both about markets and life. In any case, I hope you enjoy our conversation. Thanks so much for joining us. where your host, William Green, interviews the world's greatest investors and explores how to win in markets and life. Hi, folks. I'm absolutely delighted to welcome today's guest, Nima Shai. Nima is a very talented hedge fund manager who runs an investment firm in California called Rumi Capital Partners, which is named somewhat idiosyncratically after the great 13th century Sufi poet and mystic Rumi. Nima is definitely one of the most thoughtful people I know in the investment world, and he and I have had several fascinating conversations privately over the last few years, but he typically flies under the

radar. So it's really a rare gift to have him on the podcast. It took a lot of cajoling and coaxing of the last couple of years to get him on the podcast and to have this opportunity to share his insights more broadly with you, our listeners and our viewers. So Nima, it's lovely to see you. Welcome. Thanks so much for joining us. Thank you so much for the invitation. It's a real honor. It took a while, but we're here together in the end. So thank you. It's great to see you. I wanted to stop by asking you about your family background because I think it's fair to say that your parents weren't yearning for you to go to Wall Street or become a kind of swaggering hedge fund manager, right? What kind of environment did you grow up in and how did it shape the person you would become? Yeah, thank you for the question. My parents came to the U.S., they came to Southern California following the Iranian Revolution. And like many Persian families of that era, they basically had to come here and start from scratch.

I was the first generation to be born and raised in the U.S. And, you know, my family is full of intellectual curiosity. many people were educators, multiple people have authored books. My family has a handful of really talented musicians, but almost no one. Very few people in my family were all that interested in business. Dinner conversations in my house would sort of migrate to philosophy or classical music, definitely not interest rates or the stock market. So business was never really part of my orbit whatsoever.

And I think that the initial spark of interest in investing was sort of born out of insecurity, if anything. I remember seeing how both the dot-com bust and the 2008 financial crisis impacted so many people around me, people that I loved. And there's this particular discomfort when you have no understanding for something like that, which is happening and sort of reshaping society. You don't know why it happened, you don't know what's going to happen, and really having just no sense. And so I sort of made it a priority to learn a little more about this world.

And as I started to learn more, it really felt like this very natural extension of, you know, my temperament and interests. And ironically, it's not all that different from those same sort of dinner conversations that we were having, which on the surface, may have been about literature, poetry, or something like that, but really it was about observing human nature, understanding human psychology and sort of seeking the essence of things, what's the nature of things, seeking, you know, trying to figure out what's really going on. Now, at the same time, in Persian culture, there's this running joke that you can be anything you want as a profession, anything you want, any kind of doctor or engineer that your heart desires. And so when I decided to become an investor, there really wasn't much precedent for that. I would be, I would tell that to someone

in my circle and you could see, you know, the response would be something like, so you want to be like a bank teller? And I would say, no, you know, I want to invest in the stock market. And you could just see on their face some concern like I had just confessed to like a gambling problem. But from the very beginning, investing was, felt like the ultimate kind of intellectual adventure. It was this microcosm where you could practice your discernment and your creativity and your temperament and your reasoning. And you got this objective feedback loop, which was so appealing. It was incredible. It was sort of an amazing thing that you could professionally pursue your natural curiosity. So we were chatting right before this conversation about your high school years and that you

were a somewhat eccentric high school student and already very independent. Can you talk a little bit about that? Because it seems like in some way, that's something that all of the best investors have in common is this kind of willingness to diverge from everybody else. Yeah, it's a little embarrassing when I reflect on it now, but a little funny as well. When I was thinking about what led me to investing, I was kind of playing back all of these different parts of my life. And one of the commonalities is that it was always really difficult for me to buy into something that my heart wasn't in it fully. And I remember on many occasions in high school, you know, once you turned 18,

I learned that you could actually just go sign yourself out and you didn't need a parent note anymore. You could just say the reason you were leaving and sign your name and leave. And so there were many occasions where I would not be all that interested in whatever it was that we were studying and I would sign myself out and I would ditch school. And ironically, it wasn't that I would ditch school and go smoke cigarettes on the side of the building. No, I would go to Barnes & Noble and read something much more, you know, fascinating. And I think that that natural inclination to go deep in areas that I was very interested in

was a bit of a foreshadowing to investing for sure. It's funny. I was pretty similar at high school. I went to Eaton, right, where, you know, was just a bit of, you know, I was very, very disciplined. Like, if you showed up late, you were in trouble. And if your work wasn't good, you got literally what was called a rip. They would rip the piece of paper.

And you would have to show your homework to your housemaster. And I, in my last year, I was only taking three subjects, like English, Spanish, and history. And I just decided my history teacher was boring, so I didn't show up to history anymore. I just decided I was going to teach myself. And in some weird way, as a journalist, as a writer, that's a really useful characteristic, just say, no, I'm going off and doing my own thing. And so I think it's one reason actually why I was really fascinated by great investors is there is an element of kind of, you know, diverging from the crowd and deciding, no, I'm just going to crack the code for myself. You guys just make more money than we do as writers. I'm not sure, but I think it's definitely true that this, this willingness to think for yourself was definitely hammered into me as a child, not so much with investing for sure, but this tendency to,

not accept what is the commonly held view or the mainstream view or what the news media is talking about all the time or the narrative, but to try to figure out what's actually going on. And my parents certainly instilled that in me pretty early. And you went to UCLA and then studied mathematics and economics. So in some way, there was a part of you that was kind of very left hemisphere oriented, as you've explained it to me in the past, and sort of convinced that if you could master things like maths and statistics and economics, you'd have these skill sets to understand reality. And my sense is that you gradually came to realize that actually

comfort in numbers and logical reasoning and the like was not going to cut it. Can you talk a little bit about that evolution? Yeah, absolutely. The way that it's actually come together for me is this idea of branches and roots. Rumi has this quote that I love where he says, maybe you're searching among the branches for what only appears in the roots. And I think that that quote has a lot of significance for investors. And when I just reflect on the investment industry broadly, I noticed it both in myself,

but I noticed it in the industry in general. And it's this idea that if you can just get more precise, if you can quantify reality, if you can sort of measure things, the industry today has swung so far in the direction of quantification. You see it in, you know, expert calls and credit card data and web scraping technology. We have these extremely powerful tools today that can measure and try to predict what's going on. But it's still the case, as it's been for much of the last century, that almost no one compounds capital at very high returns for all that long. Despite the fancy tools, despite having tons of incentives, despite working really hard,

it's just still very difficult. And so I reflect on this and I wonder, what is it that we're missing? What is it that we're missing? What is it that I'm missing? Because I started out as being really technical and really focused on mathematics and quantification and if everything is about reason and science. And sure, but it felt like I was just lost in the branches and I missed the roots. And so what is it about what are the branches and roots as it relates to investing? So the branches are what everyone can see and measure. It's last quarter margins. It's this week's unit growth. It's next month's inflation print. You know, it's all of these quantifiable pieces of information that are devoid of reality. devoid of context. And so what would be the roots? The roots of a business are all of these

qualitative forces that are causal to the future economics of a business. You know, Lou Simpson used to always say that all investing is figuring out the future economics of a business. And that statement might sound easy enough to just blow right past it, but it actually creates an extraordinarily high bar. You know, most investors tend to to fixate on the current economics, the current branches. They fixate on the present reality. But every once in a while, you can get a really deep sense for what the future economics of a business might be. And in those cases, it's usually the case that you have a sense for the roots. And so what are the roots? The roots could be something like the motivation of management, the culture of the company,

the quality of the product, the alignment with customers. None of that shows up on any spreadsheet. You can't model it, you can't quantify it, but they're actually the most real parts of a business. So the question to me became, if the roots are what truly matter, why isn't everyone focused on them? And the challenge from my perspective and actually the opportunity is that the roots require some intuition. So it wasn't all about getting better at Excel and suggesting that the stock market, investing in the stock market requires intuition. I think makes many people uncomfortable because it feels subjective and it feels squishy and it feels, you know, very hard to communicate. But it's precisely those qualitative invisible factors that live upstream from the financials that everyone else is sort of focused on.

As you mentioned, you wrote this piece, Roots and Brunches. And I think it was originally a speech that you gave at Columbia, maybe in our friend Chris Begg's class in 2023, but then it became a shareholder letter of yours. So I've read it in both. places. And you quoted in there, I think Robert Persig talking about pre-intellectual awareness and this, you talked about this ability to apprehend essence being suprarational. Can you talk a little bit about that sense that it's kind of super rational? There's something there's something pre-intellectual in it. It's something I sometimes have talked about with Chris Begg as well, that he has this sense that we have an embodied ability to tell whether something is true or not.

Like when you meet a CEO and you're trying to decide, do I trust this person? Is this person actually honorable or not? So I think that in most cases, the roots of a business are too hard to tell. It's sort of, it's not obvious. And I think the first thing to note is that you only really want to swing when it's pretty obvious. In Buffett's parlance, you know, there's no call stress. but there are some cases where you can know with some confidence what the roots of a business are.

And in Persian, we have this very old expression that is probably more than a thousand years old. And it is Cheshmede, which literally translates to eye of the heart. And it's this idea that the heart is more than merely this organ that pumps our blood. it's actually a faculty of perception, and it's capable of grasping non-material truths. And whether we like it or not, we live in a reality that's qualitative. And seeing with a qualitative perspective is so important I found in investing. And in terms of the pre-intellectual awareness, sometimes intuition is framed as this sort of superpower that you have to develop. And I think that it's less about developing or sort of achieving a superpower and more about

clearing away everything that's muddying or perception. I truly believe that all human beings have this capability to discern and perceive non-material qualitative truths. These are things like trustworthiness and sincerity and ambition and beauty. You know, these are qualities that you can't. model them and you can't quantify them, you can't measure them. But there's something pre-intellectual that can actually grasp and recognize those qualities when you're in the face of them. You had a lovely example of this when we spoke a couple of weeks ago where you were talking

about the experience of, I think, going into the mall of a parking lot in a Tesla in like the full autonomous driving mode. Can you talk about that a little bit? Yeah. I mean, this is actually quite timely because or Tesla got an update just this morning and I was out, you know, testing it. It's version 14.2, which is the latest update that the company has rolled out. And, you know, it's hard to explain what makes this product special. But overwhelmingly, when I take my in-laws for a ride, or my parents or friends who are not familiar, there's this kind of moment of awe. And the example that I was talking about before was that we were driving to Costco one evening and I clicked the button in the car and it's navigating through all of these construction zones

and it pulls over for emergency vehicles and it gets on the highway and it gets off the highway. I haven't touched the steering wheel or pedals the whole ride. And then it pulls into the parking lot of Costco and there's plenty of open spaces that it decides I'm going to skip these open spaces and I'm going to go a little further and see if I can find an even better spot. And then it just pulls in perfectly and it stops. It finds its own parking spot. And I'm thinking, this is almost a miracle that this exists. And very few people, I think, understand the power of that technology without having felt had a direct perception of it themselves. And I think that that is one example of coming face to face with quality. You know,

there's plenty of other examples. I'm sure the first time that we all touched an iPhone, we thought this is some incredible, you know, black magic. And the first time you got same-day delivery from Amazon, where you order a book and it shows up to your doorstep in two hours, you know, some of these customer experiences, it's worth just listening to them because they tell you something about the quality of what's leading to that experience. You had a lovely word for it that you mentioned a while back that you and a friend and investor friend had talked about the quality of blown awayness. Yes. Yes, blown awayness is that experience that I'm referring to. And unfortunately, it's not an industry term that you can quantify one out of ten, but I think it tells you a lot about the

quality of something that you're encountering. And it's anything as simple as, you know, your favorite restaurant. You have a perception that tells you when the quality of that restaurant has either improved or deteriorated. There's something within you that knows. And oftentimes it's emotional, it's physiological. We all have this commonly held dogma that you're supposed to turn off your emotions when you're an investor. And I'm not sure that that's always right. Yeah. And it's very related to both Robert Persig and Ian McGilchrist talking about left brain. There's a lovely thing. I think you've quoted in one of your letters where Persig writes about dynamic quality and he describes it as the pre-intellectual cutting edge of reality.

So I think we have this sense, this sense that there's something there where, you know, like my friend, the end of the hour would say, you know, that the quality has its own frequency. Like you can tell when you're in the presence of something, usually that's extraordinarily high quality. But yeah, it's hard to explain it in spreadsheet terms. And there's something lovely. I think you once quoted something from Rumi to me where he said something along the lines of the soul has been given its own ears

to hear things that the mind does not understand. And so it's kind of hard, right? It's like in the same way that Nick Sleep and Case Zakaria, Zach, were becoming obsessed with Persig. And I think I wrote in my chapter about them that, you know, on Wall Street it wasn't really popular to be, you know, having all of this mystical mumbo-jumbo about motorcycles and maintenance and the like. And yet there's something real there that tends to be, I think,

underestimated by very left brain, very logical, very numbers driven people on Wall Street. Absolutely. And I think that there's even more to that. You know, this idea that we should shut off our emotions as investors, I think is a mistake. You know, in my judgment, it's not so much emotions per se that get us into trouble. I think it may be the human ego that really gets us into trouble. And there's a subtle difference, right? You know, the human ego is like this armor that we build that tries to protect us against the uncertainties of life. It's the part of us that operates from fear. It's the part of us that, you know, when we realize how middle we actually control in life, we develop this ego to try to protect ourselves. It's sort of

self-preservation. And when we make investment decisions from that place, of course we will make terrible mistakes because the ego is what distorts our perception. We already have this capability to discern quality. We have that Cheshmedel, but we develop this egoic perception that kind of muddies the mirror of being able to see clearly, distorts our perception. And when I look around our little microcosm of investing, I see this ego showing up all over the place. You know, it could come in the form of self-preservation. For example, I can't own that because it'll make it harder to raise money. You know, you hear that all the time. Or I can't sell this losing position because it will be admitting to my clients that I made a mistake. And the ego is unable to admit error. The ego thinks

it already knows. So then the behavior becomes, well, I'm just going to hold on to this losing position, even though I know, you know, it's not the right thing to do. And I think another way that this egoic perspective shows up in the investment world is this illusion of control. And I'm as guilty of this as anyone. You know, early on as an investor, it was very natural to think, If you just build that perfect spreadsheet, or if you make the hundredth customer call, then you're getting closer to reality. And we usually have to learn the hard way that reality seldom bends to the whims of our spreadsheet. And all that activity may be simply masking or inability to just say, I don't know what's going to happen. The map is not the territory.

and by contrast, emotion can be incredibly beneficial to investors. It might be blasphemous to say, but I don't think investors are using their emotions enough. In my experience, when you discern whether the CEO sitting across from you is trustworthy or not, or whether you've experienced the craftsmanship of a product, these are all pre-intellectual. there's a direct perception and you sort of know it when you see it.

Even subtle emotions can tell you something important. What I mean by that is when I reflect on my ownership of a business, right? Like you've owned a company for a few years, when you reflect on just how that feels within you, that can tell you a lot. When you own something for a few years and you find yourself becoming more and more impressed with the business as time has gone on, that's a certain. signpost by itself because the normal experience is that you own something for a few years and the mediocrity of it just becomes more and more evident and it just took you a while to figure

it out. So when you notice that you're actually becoming more and more impressed and you notice that emotion within yourself, that is something to listen to, I think. I want to go back in time a little bit in the chronology of your career because in some ways you started out in a very different place in a very different kind of environment where you came out of college, having left UCLA, and you got hired at PIMCO, which is a very powerful firm with enormous amounts of money under management. I think at the time 2014 to 16, when you were there, it was the world's biggest bond firm and had been co-founded famously by Bill Gross, clearly a brilliant, very eccentricly talented, difficult, demanding guy by his own admission. I was reading an article about him in the Wall Street Journal today from

2014, co-written by Gregory Zuckerman. And he quoted Gross saying, sometimes people will say gross is too challenging and maybe so. I would say if you think I'm challenging now, you should have seen me 20 years ago. So it was a kind of famously hard charging intense place, not the sort of place where you would talk about your emotions and your intuition and about Rumi and the like. And in Zuckerman's article, he was talking about how people on the investment team there would literally arrive at 4.30 a.m. and stay for 12, 13 hours or more. What was it like as a 22-year-old kind of new to the business, a kind of hungry-driven, smart young investor? And this is sort of so, it's so not like a, I mean, obviously, they're brilliantly clever, highly educated people,

but it wasn't a sort of soulful, ruminative, contemplative kind of environment. It was sort of the opposite. Yes. And I think, you know, Rumi actually has a quote, which is that all things are known through their opposites. So I think in some ways, that experience working at a place with that sort of intensity was what clarified and sort of gave me a sense for what I wanted to be doing long term. And, you know, the experience of PIMCO, I was very lucky because I was hired there directly out of undergrad. So I was the youngest analyst on the team by some years. And it was this intense environment. And you're right, we would get to the office 445, 5 a.m. You would have a suit and tie on. It's usually dark when you arrive in the office. It's usually dark when you leave the office.

There's this culture that you're kind of expected to have a smart sounding cogent opinion on every little economic development, every little piece of news that's related to one of your companies. And I was so lucky to have had that kind of experience where you essentially have an ability to fly around the country to meet with executive teams as a 22-year-old to get access to any piece of research. You know, we had central bankers would come and advise us on the economy. You know, former central bankers would come and advise us on the economy. And so you would think that we had every possible resource. We had PhD computer scientists that would come, you know, run correlations on different asset classes. We had hundreds of analysts that were flying around

the country to meet with companies and form opinions on specific securities. You would think that we would have every possible resource there is to compound capital at extremely high rates. And yet, I think six months in, I was, reflecting on this. And it was a little confusing to me why people like Warren Buffett and Charlie Munger and Lou Simpson and the like were able to compound capital at 20 plus percent for decades, despite being essentially a person in a room without a computer. Whereas we're sitting here in our very large offices, working really hard, you know, cortisol is in the air with great pedigrees and our ties on. And we're compounding at, you know, basis points above.

the benchmark. Not to say that that's not an admirable thing to do, but it just felt like I wasn't missing something in some ways. Now, I was incredibly lucky that there were certain people at PIMCO that took an interest in my development, and they really wanted to teach me how to think about things the right way. And so from that perspective, it was an incredible learning experience in one that I wouldn't trade for anything. There was a lovely line, I think in one of your shareholder letters. I just read all of your shareholder letters over the last couple of days and you wrote somewhere, why in this age of information overload where data gushes like a digital waterfall, is investment success still so elusive? Why does Warren Buffett with his egg muffins and bridge

games outperform the armies of well-paid analysts with six monitors each? Which I think gets at this question that you were wrestling with at Pimco. There's something really strange about this game, right, that as you put it in that shareholder letter, you have these web scrapers kind of predicting weekly revenues or algorithms discerning the emotions of people's posts on X, and you have every tool. And yet there's something that's missing. And we'll talk in a minute about Lou Simpson, which is sort of the opposite of that. But what did you conclude about why these incredibly smart people who in many cases, I mean, literally, I think Muhammad L. Arian was paid over $100 million a year. Bill Gross who was paid over $200 million a year. I mean, these were the smartest, incredibly intense

people with every resource. Why isn't that reflected in outrageous returns like Warren's? I think it's a complex problem. And when I reflect on what is the root quality going on here, I think a lot of it has to do with risk aversion, and that's across the spectrum. That's not just the investment products that we were managing. It actually goes into the institutional level. It goes to, you know, many of the people overseeing these institutions. There's very little tolerance for volatility. No one wants to look wrong for any short period of time, even if it means that your longer term results will be much better. There's very little tolerance for discomfort of any kind. And so the

bias and the incentive structure is to just operate in a way that will keep the assets. And if that means slightly less performance over time, I think that that's a trade-offs that this industry has made for better or worse. And for better, you know, it allows for people with a different orientation

to have better results. Let's take a quick break and hear from today's sponsors. All right. I want you guys to imagine spending three days in Oslo at the height of the summer. You've got long days of daylight, incredible food, floating saunas on the Oslo Fjord, and every conversation you have is with people who are actually shaping the future. That's what the Oslo Freedom Forum is. From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering its 18th year bringing together activists, technologists, journalists, investors, and builders from all over the world. many of them operating on the front lines of history. This is where you hear firsthand stories from people using Bitcoin to survive currency collapse, using AI to expose human rights abuses, and building technology under censorship and authoritarian pressures. These aren't abstract ideas. These are tools real people are using right now.

You'll be in the room with about 2,000 extraordinary individuals, dissidents, founders, philanthropists, policymakers, the kind of people you don't just listen to but end up having dinner. with. Over three days, you'll experience powerful mainstage talks, hands-on workshops on freedom tech, and financial sovereignty, immersive art installations, and conversations that continue long after the sessions end. And it's all happening in Oslo in June. If this sounds like your kind of room, well, you're in luck because you can attend in person. Standard and patron passes are available at Oslof Freedom Forum.com with patron passes offering deep access, private events, and small group time with the speakers. The Oslood Freedom Forum isn't just a conference. It's a place where ideas

meet reality and where the future is being built by people living it. If you run a business, you've probably had the same thought lately. How do we make AI useful in the real world? Because the upside is huge, but guessing your way into it is a risky move. With NetSuite by Oracle, you can put AI to work today. NetSuite is the number one AI cloud ERP, trusted by over 43,000 businesses. It pulls your financials, inventory, commerce, HR, and CRM into one unified system. And that connected data is what makes your AI smarter. It can automate routine work, surface actionable insights, and help you cut costs while making fast AI-powered decisions with confidence. And now with the NetSuite AI connector, you can use the AI of your choice to connect

directly to your real business data. This isn't some add-on, it's AI built into the system that runs your business. And whether your company does millions or even hundreds of millions, NetSuite helps you stay ahead. If your revenues are at least in the seven figures, get their free business guide, demystifying AI at netsuite.com slash study. The guide is free to you at netsuite.com slash study. NetSuite.com slash study. When I started my own side business, it suddenly felt like I had to become 10 different people overnight wearing many different hats. Starting something from scratch can feel exciting, but also incredibly overwhelming and lonely. That's why having the right tools matters. For millions of businesses, that tool is Shopify.

Shopify is the commerce platform behind millions of businesses around the world and 10% of all e-commerce in the U.S. from brands just getting started to household names. It gives you everything you need in one place, from inventory to payments to analytics. So you're not juggling a bunch of different platforms. You can build a beautiful online store with hundreds of ready-to-use templates, and Shopify is packed with helpful AI tools that write product descriptions and even enhance your product photography. Plus, if you ever get stuck, they've got award-winning 24-7 customer support. Start your business today with the industry's best business partner, Shopify, and start hearing... Sign up for your $1 per month trial today at Shopify.com slash w

Go to Shopify.com slash WSB. That's Shopify.com slash WSB. All right. Back to the show. Yeah, you mentioned somewhere that when you look at the history of investing, you see that there were these very long periods of outperformance for a lot of the great investors,

which are very uncomfortable, right? They're emotionally very uncomfortable, you know, whether it was John Maynard Keynes or, Ben Graham or Warren and Charlie. Can you talk a little about that? Because I think, I think that's one of the things that makes outperformance so difficult is, as Monash Papry once said to me, you know, the most important quality of a great investor is the ability to take pain. Yes. I think that studying investment history at any level makes it clear that over the course of a multi-decade investment journey, there will be these large periods of underperformance and

large declines inside of those periods. Just glancing casually at some of the notable investment records of history, this just becomes quite obvious. You could look at the 1930s and great investors like Ben Graham's fund, I think, declined by 70%. And he was still making distributions out of his fund. And so I think the starting capital was down maybe 80% by the end. You know, the personal portfolio of John Maynard Keynes, I think declined by 80% in the 1930s in the portfolio that he was managing at Cambridge declined by like half. You could go to the 1970s where, you know, Charlie Munger had 80% of his capital in two stocks. I think it was the blue chip stamps and the New America fund. And they were both very cheap stocks.

But his portfolio declined by more than half in two years. And those two years alone made the prior seven years of returns, I think something like zero cumulatively. Even Shelby Davis, I was reading recently, I think his personal portfolio in the 1970s declined by 60 percent because he had margin debt at that time. In the last few years of the 1990s, Lou Simpson himself was. 50 or 60 points behind the S&P 500, and that little stretch of performance actually wiped out like a decade of outperformance against the market. And of course, you know, Berkshire Hathaway

itself has declined by 50% multiple times over the years. So the list goes on and on. You know, I'm kind of a nerd in looking at these old records because they fascinate me. But we know, we know that these periods of extreme volatility and underperformance are just very normal. So the question then becomes, given that reality, how should you structure your environment for that inevitability? How should you structure your life and your business and your environment? And what I found is that when you have a truly long-term orientation, you start to just have to surrender in some ways. You simply stop engaging with certain kinds of questions. For example, will there be a recession next year? Is the market about to crash? Is AI a big bubble that's about

to pop? You know, is the U.S. fiscal situation unsustainable and going to lead to a crisis at some point? These are all very interesting questions, but over a long time horizon, they just don't matter that much. And spending a lot of time sort of ruminating on these kinds of questions has been an expensive distraction for many people over many years. As far as I'm concerned, there will be severe bare markets over time, and there might be even one or two every decade. And I've found that it's not worth having a lot of anxiety about when those periods come. It's much better to just know that they will come. There's a story about Lou Simpson. that I, that really was instructive to me about this. And it was his experience in 1987. So he went

into the 1987 period thinking that stocks were very overvalued. And I think many smart people at that time believe that stocks were very overvalued. He couldn't find anything to do. So he actually took his portfolio to 50% cash early in 1987. And you might think this is incredible. This is you know, clairvoyance, what amazing market timing. And when he reflects on that period, she sold stocks at the highs and paid his taxes. And then the market crashed and he sort of deployed a little more capital. But the market stepped back so quickly that he didn't deploy his capital fast enough. And so he made the right decision at the highs, but didn't make the right decision at the bottom. And this to me was very instructive because you have to make multiple

decisions correctly to really take advantage. And I think in his estimation, he thinks that he added some value net of all of that. But it may have just been better to remain fully invested and just roll with the punches. And so that's kind of the approach that I've taken to thinking about this. Yeah, just to close the loop on this idea of your willingness to ignore macroeconomic prediction, there were a couple of lines I really like from your shareholder letters that I wanted to highlight one of them from a recent shareholder letter. You said, one of the enduring amusements of this profession is how reliably investors are shaken by what is, in fact, a recurring patent, right? This pattern of market meltdowns and dips and predictions of gloom and doom. And you said, what if we simply

chose not to partake in the theatrics? And I think that's a really important question, just this decision, as you put it, it's a liberating question to say, no, I'm willing to free myself from geopolitics and macroeconomics and all of that. And what you said, which I'm quoting because I think it distills an enormous amount of practical wisdom. You said, we are focused on owning individual businesses whose long-term reinvestment dynamics are resilient to changes in macroeconomic conditions. Do you want to comment on that in any way? I think it gets such a profound and essential truth about investing, that if you're, that you can make this very conscious decision just to focus on businesses that are resilient to changes in macroeconomics rather than saying, I'm going

to try to predict what's going to happen. Yeah, I mean, I think that this work is, it's almost unnervingly simple. You know, the investment business is really quite simple. And at the end, at the end of the day, it's about trying to understand the economic reality of a business. And as they said, Lou used to say all the time that it's about predicting, it's about understanding the future economics of a business. Now, to the extent that the macroeconomy is going to have a huge impact on the future economics of this business, then it may not be a great business. to the extent that going into a recession is going to hurt the business or to the extent that there will be competitive onslaughts at some point or a product might fail, for example,

things can happen in businesses all the time. And I think the idea is to own specific businesses that are resilient despite the inevitable sort of turbulence that life presents. And I think it really simplifies life to opt out of a lot of these things that are outside of our control. I want to go back and talk him in much more detail about Lou Simpson, who's clearly been, in many ways, the formative influence in your life as an investor. So you moved to Naples, Florida in, I think, 2016 and worked until 2019 with Lou at his firm SQ advisors. And for people who don't know, who've just heard us mentioning him, Lou was head of investments for GEICO, this auto insurance company that's now owned by Berkshire Hathaway completely. And he was there for 31 years, I think,

from 1979 to 2010 and crushed the market over that period by a huge margin. And you recommended to me a book that I read a chapter on Lou yesterday, a book by your friend Alan Bonello on concentrated investing, where he talks about the circumstances when Buffett first hired him. And Buffett said, after meeting him, asked him about his personal portfolio. And then after meeting him said something like, stop the music, we found our guy. And he later said, simply put, Lou is one of the investment greats. This is from a letter, I think, that Buffett wrote in 2010. Tell us about what it was like when you first met Lou, because in some ways, the culture

that he created was diametrically the opposite of the culture that you had said. seen at Pimco. And this isn't a criticism of Pimco. It's just he embodied something very, very different. Absolutely. You know, every time I think of Lou, the memory that always comes is the first time that we met. And I was in my mid-20s at the time. And as I said, you know, as you mentioned, I was working at a more or less traditional investment firm, which was Pimco. And, you know, I remember the energy that I carried with me at my first job was this sort of over-analytical habit. I had this formality, this intensity.

And when I arrived in Chicago to meet with Lou for the first time, I carried a lot of that energy with me. The context of our meeting was actually to discuss a company that I thought he might be interested in my mind, I imagined this very intimidating investment legend was going to rigorously cross-examine, you know, every little detail of my investment thesis. And so mostly out of insecurity, I lugged along with me to Chicago, this very thick stack of research material with charts and valuations and everything. I was ready, I was sort of ready to go to battle, intellectually speaking. And I remember,

I remember stepping into the elevator with my suit and tie on and, you know, your heart's beating a little faster than usual, and I lugged along my data points with me and my thick stack of research. And it's one of those long elevator rides up where your ears are sort of popping along the way. And I remember thinking I'm going to be met by an assistant or ushered into some kind of waiting area. And instead, you know, the door's open and it's just Lou himself standing in the hallway, very unassuming, no formality, no pretension. And he led me into an office that was really the polar opposite of the office that I had just been in, you know, the day before. There were no blumerg terminals. There was no, you know, financial TV on. It was like the

library of a scholar, you know, a comfortable chair, a couple piles of reading material, and this just very calm presence that immediately struck me. And he looked at me as he led me inside and he said, you know, make yourself at home. Let me make you a coffee. And I remember that that line just sort of stopped me in my tracks because here was someone who had compounded capital at world-class rates for decades.

Someone who Warren Buffett had praised many times over the years. And someone that I had been studying from afar since college. My idea of passing time between classes in college was to pull up an old Berkshire Hathaway 13F. And in some of those early years, you could actually scan down and see which holdings belong to Lou and which holdings belong to Warren. And so I would sit there at the UCLA coffee shop trying to reverse engineer why Lou bought Freddie Mac or Moody's, you know, why he bought Nike in the early 90s and held it for 20 years or more. And now, Now, here he was this person behind these decisions, stepping away to make coffee for a probably

visibly nervous 20-something-year-old kid who hadn't done anything yet and who was so early in his compounding journey. And I remember thinking to myself, you know, I should be making you the coffee. And when he returned, he didn't launch into some kind of monologue. He didn't try to assert how smart he was. she would ask these questions with this very sincere curiosity. And it was this remarkable receptiveness for someone with his experience and with his reputation. And, you know, that first meeting left such a deep imprint on me because it kind of opened a window that there was just a different way of being in this work.

It didn't have to be this hard charging zero-sum way of operating, this kind of hyperactive way of operating. Lou carried himself with remarkably little ego, and that was so different from the archetype of person that you typically run into in the investment world. The normal experience is that you come across folks who are very bright, very hardworking, but for whatever reason, they insist on puffing up their accomplishments and telling you all about their most recent investment win and their assets under management and, you know, all this sort of thing. And Lou was just so different from this. Some of his most extraordinary achievements would just sort of slip out accidentally after having known him for years. He seemed deliberately uninterested in indulging that

kind of self-congratulatory aspect of himself. He was quick to say, I don't know, when someone would disagree with him or challenge one of his beliefs on a company, he wouldn't get defensive, he would simply say, yeah, you know, maybe you're right. I should think about that more. And I truly believe that his humility was, you know, his lack of egoism was the reason why he was a good investor, was a big reason why he was a good investor, because it gave him a clearer perception of reality. The one conversation that I ever had with him, I think I may have told this before, this was when I had a Zoom breakfast with Charlie Munger and a few people like Lou were on the call. And Lou already, you know, who passed in in 2022 was already obviously pretty

unwell, I think. And he was so lovely on the call. And it was a very, it was a very strange call because I got asked all our homework is going to be to study your book, Rachel, why is happy? And then we'll discuss it. So I'm in this sort of embarrassing position where it's like, oh, here I am. I'm going to teach Lou and Charlie about how to invest. And there was a moment where somebody, you know, Charlie was very dominant through the conversation. And then someone turned to Lou and said, what do you think of the book, Lou? And Lou was really lovely about it, like very, very polite and charming and said how helpful it is to have stories of greater vests like, because we learned through stories. And then we were talking about Alibaba, which he and

Charlie had just been buying. And Charlie had been saying, oh, I'm all in. And Lou said something like, well, I just bought it yesterday. So it's bound to go down 50% immediately. And there was something sort of so self-deprecating about it. Like he wasn't there to tell you, I just And I asked him, why did you buy it? And he was saying, well, you know, it's a, it's a dominant business in a fast-growing country and it's extraordinarily cheap. But it was funny because it did go down 50%. And so in a way, it was like very typical of him that he was so humble and self-deprecating. And in a way, maybe it was also a recognition of the fact, this is a really hard game. And you are going to, you know, you are going to go through these periods where just stuff happens.

Yeah, absolutely. You know, it brings to mind, a friend of mine offered me a definition of humility that I think is remarkably precise. I think it's the best definition of humility that exists. He said that humility is the awareness, it's your awareness of your utter dependence on all that exists and your interdependence on everyone around you. And the opposite of humility, of course is like a self-centered perspective to think that we did it all alone, that we're the ones in control. That clouds your perception,

it distorts your judgment. And this dynamic was so clear when Lou talked about his portfolio. You know, when everyone else would pitch their great ideas, Lou would say things like, you know, I think the portfolio is just okay, maybe it's a little tired. And this is, you know,

this is one of the best investors of all time and he's just sort of ho-hum about his portfolio, whereas if you went into the Monday morning meeting of many large investment firms, you would hear people pounding the table on probably mediocre ideas in many cases. And I think there's something that's objective about his humility. It allows you to see things clearly. And his humility wasn't performative. It wasn't like this inauthentic, humble bragging. It came from a real awareness in how little we have. actually control. And I think, you know, Buffett's line about the Ovarian Lottery, I think, captures that spirit so well. We all like to believe that we are the sole cause of our own success,

that things are so deterministic. But in truth, you know, so much of anything that goes right in life in investing is really just the beneficence of life. There's a really lovely line also in Alan Bernal's book that I remember seeing before many years ago from Lou where he said, we are sort of the polar opposites of a lot of investors. We do a lot of thinking and not a lot of acting. A lot of investors do a lot of acting and not a lot of thinking. And I'm wondering what you learned from him about the importance of detaching ourselves from the noise and distractions and the kind of casino element of Wall Street. Yes, I think Lou lived a pretty balanced life in the years that I knew him. He would read broadly.

He had this amazing sense of humor. You know, he would make it a priority to exercise. He would, in the mornings, he would go for a long walk or he would go for a swim. I remember on one occasion, it was definitely in the middle of the week, and I think the market was open. And I think our portfolio was probably down quite a bit that day. And he just called me up and he said, you know, there's this new exhibition at MoMA in Chicago. Do you want to go with me? I said, great. And we just spent the afternoon wandering around, you know, looking at art.

You know, this is very different from the kind of experience that you might have at many, many investment firms. So I, you know, I won't claim to have all the answers about this, but what I do know is that if you intend to have a long-term investment journey and you have surrendered to a lot of this volatility, I know that if you're constantly sprinting and you're always wired and you're reactive to every little data point and you're just staring at ticks on a screen, maybe that will help your results for the next month or two months or six months. But over the long term, it will completely destroy your health. It will destroy your physical and mental health. It will strain your relationships. And ironically, it will make the investment

decisions worse at some point. And it's sort of perverse that the harder you push, the harder you try at investing, the shorter your runway. And in the end, you know, compounding is all about the number of years. And so I think creating space in your life is something that I learned from him and something that's invaluable. So much of modern investing is preparing a memo or updating a model. You know, there's so much reactivity. And to his point, you know, so much, so much, so little time is intentionally devoted to reflection. And it's not intuitive for most people to think that going for a walk may be better for your portfolio than, you know, adding another scenario to your Excel model. Yeah, you've mentioned in the past that sometimes your best investment insights

feel like these gifts of serendipity. They're not, they're not always the result of mechanical rigor. But I remember also you talking to me about the importance of actually kind of structuring your life in a very conscious way to give yourself this kind of spaciousness and lack of noise. And you were saying that it's not just how you schedule your day and how much meditation you do and the like. It's also your choice of who your limited partners are and your fund and who's on your team, if you have a team or the kind of businesses you hold. Can you talk a little bit about that? Because it seems to me this is such an important part of actually creating a kind of countercultural lifestyle that gives you a sort of unexpected edge in investing. Yes, edge is a funny concept.

Just maybe we'd talk about another time. My view is that whatever you build, whether it's an investment partnership or anything else, it ultimately lives downstream from how you choose to live and the values that inform that. And so I've always tried to ask myself, what are you actually optimizing for? Because if what I'm doing is not in alignment with the answer, my personality is such that I will not last very long. I'll start to feel that imbalance internally somewhere, even physiologically. And in investing in particular, the power of compounding reveals itself when you stay in the game for a really long time.

Long gravity carries most of the freight here. So for me, the first principle in deciding what to do was to ask to build the house that you want to live in long term. You know, that was really critical. And I can't tell you the number of times I've seen someone very talented, you know, lovely person, build this sprawling investment business only to privately resent a lot of the complexity that comes along with it. Less time becomes devoted to the craft of investing. More time is spent managing people or fundraising or doing administrative tasks. For me, personally, the craft of investing was the part that I loved. That's how I wanted to spend, you know, the majority of my time. And that

meant that the structure had to be exceedingly simple and free from unnecessary complexity. The work had to fit my temperament and, you know, it had to sort of match your energy in some sense. So today, I run one portfolio. There's fewer than 10 holdings. I might find one or two new ideas in a year. The rest of the year is spent, you know, quote unquote, sharpening the axe. That simplicity gives you an enormous amount of space for reflection, to try to think clearly, space to make long-term decisions without distractions, space to have close relationships with every one of Rumi's partners. In more than six years, we haven't had a single redemption, which I think is some kind of record for a strategy that's sort of flinging up and down depending on the year.

but it's really a reflection of having found, you know, I'm so grateful to have found partners who are truly high quality and are aligned in, you know, our goals and and our thinking. I think there's always an inherent tension, though. And it's something that I've been wrestling with for a long time. And it's this idea that if you can help more people, of course, that's intrinsically better. It's something I spent so much time wrestling with because what greater fulfillment is it than to be of service to people that you have real relationships with? From that perspective, it's like the more the merrier. But there's always this balance that is this counterbalance to be mindful of. And I don't think that you can scale

close real relationships infinitely. The moment that you stretch something beyond its natural equilibrium, I think it exacts a payment from some part of your life, whether it's your work, whether it's your personal life. And, you know, stretching something can dilute what makes it work in the first place. And it's something that I just continue to think about. When you founded Broomie Capital Partners, I think it was October 2019. So it's probably a few months after SQ advisors closed or after Lou decided to close the firm and, and, you know, and retire. Do you remember his advice to you? Because it seems like in some, I mean, I remember reading that he typically had something like eight to 15 stocks, I think at Geico. What did he advise

you as you launched your career as a fund manager? His main focus was to, you know, his main advice to me was to focus on producing results rather than doing a lot of the things that you're told you should be doing, like getting a fancy office and putting together a pitch deck and running around and trying to raise money from all these people. And I'm so grateful that he gave me that advice because the first couple of years gave me so much space that I think benefited both in the process, but also the relationships with the people that did invest with me from day one. And I started Roomy not too long before COVID and not too long before another decline in 2022. And the experience of these periods were so serene.

You know, not to say that it's always comfortable to watch your account balance is declining, but it was about as easy as you might expect because you felt this alignment across the ecosystem that just made things much more seamless. And I suspect if I would have raised a lot of institutional capital out of the gate, that probably some percentage of that capital would have left during one or these periods. And maybe that experience would have been, you know, uncomfortable. And you would have felt like you disappointed people and that sort of thing. And I think his advice to just focus on producing a good outcome for the people who trust you was wise.

That word alignment seems very central to you, right? I was looking the other day at the founding principles of Rumi partners and you talked about a culture rooted in alignment and elsewhere you write about investing in a small number of exceptional businesses whose leaders are similarly driven by a core sense of alignment. And I think you're very aligned in your fee structure as well, right? Like you have a small management fee that gets smaller as you get more assets under management, so the shareholders benefit from the growth in scale. And you get an incentive allocation. Basically, if you beat a 5% annual hurdle, the compound, so it's cumulative. So if you fall behind it, it becomes harder and harder to catch up with the rabbit.

And there's a lovely line that you repeat a lot in your shareholders, where you say, I'm wholly uninterested in being rewarded for simply existing. So you're not trying to gather lots of assets and then just collect fees. Can you talk about the importance of that sense of alignment? Because I see it also in the companies that you invest in, that something like Brookfield, which has always been one of your two or three biggest positions, I remember you commenting once about how they would invest billions of their own capital alongside their shareholders' capital if they sell up a huge infrastructure fund, say. So it seems like alignment is a very central theme for you?

Very much. And the concept of alignment is another root quality that can't be quantified and it can't be measured. What happens in the investment world is that we try to set up rules and juristics to sort of force alignment. So they'll say, you know, what percentage of the company does the CEO own? Sure, you know, if they own a lot of stock, that's great. But not necessarily.

I think for certain kinds of companies, certain kinds of people, the output doesn't matter so much. Like if Warren Buffett owned a little less Berkshire-athaway stock, I don't think his behavior would change all that much. If you gave him some big incentive plan to incentivize him to compound, I don't think it would change his behavior that much. So alignment is something that, you know, I think it's best done. You have to sort of embody it first, and then the output of that is just the output. So in the case of Rumi, I wanted to emphasize that this is a performance-oriented partnership. It's not about raising capital. It's not about having a good couple of years.

It's about compounding capital for multiple decades. And I'm thinking in a quite long time horizon when I make investments. And what that means is that you also have to find businesses where the managers of those businesses have a similar orientation. So if you can align that time horizon and that sense of patience and that goal over across the ecosystem, whether it's Bruce Flat at Brookfield is thinking about the next 20 years, and then Rumi is thinking about the next 20 years, and Rumi's limited partners are thinking about the next 20 years.

If you can create alignment across that ecosystem, the odds of compounding, the odds of a good outcome, I think, are dramatically improved. How does a company like Brookfield or Appfolio, which have been two of your biggest positions since inception, how do they embody what you're looking for in terms of management, but also what you're looking for in terms of what you call long duration reinvestment runways? Because it seems like a focus on the potential for reinvestment is always almost like the defining quality that you're looking for in a business? You know, I think Charlie said it best, where the longer you hold something, the closer you will get to the intrinsic reinvestment return

of the business. And so if you intend to own something for a very long time, it's imperative that the business itself is generating high returns. Not to say that it's generating high returns on a reported basis, but it has an ability to reinvest at high returns. Because if you're just throwing off cash and you have to either dividend it out or buy back stock, it's not intrinsically compounding the business. So I'm looking for businesses that have this intrinsic ability to compound capital over time. And so I basically won't buy things or add to things unless I'm convinced in that the direction of the future economics, the direction of the compounding of intrinsic value is long-lived. So that excludes all kinds of things from the funnel. I tend not to buy things

just because they look statistically cheap. You know, these ideas that they seem like they'll be okay just for the next few years, but they'll likely face some kind of existential threat over the next few years. So I won't buy a melting ice cube, regardless of valuation. I won't buy bad business models or people that I don't believe are aligned or talented. Some people can do this well. Some investors can do this well. I'm not one of them. Now, in terms of the long-duration reinvestment, I think something like AppFolio is a good example of that. It's a business that sells software to real estate property managers. And ultimately, the product is a significant entropy reduction in the real estate industry. So it saves property managers a lot of time. It reduces

the need for labor. It just simply makes their lives easier. And the product allows you to fulfill many tasks, whether it's collecting rents or screening new tenants or scheduling maintenance or executing a lease. And because it sits in the middle of all these workflows and the employees that the property management company are all trained on this product, it touches, you know, it creates an incredible stickiness. And it touches, it sort of enjoys this center of gravity in the real estate market. That stickiness when you have customers for 10 years, 20 years in many cases, many privately held software companies will take advantage of that stickiness by cutting costs, by stopping the innovation, by leveraging up the balance sheet,

you know, jacking up prices. But AppFOLio's ethos, it sort of embodies a partnership approach. It's by far the most customer-oriented culture in the market. And to be in a position like that allows them to take a much longer-term view. So they tend to add functionality that is impactful for the customer. And because they're sitting in the middle of all these workflows, they can continuously develop new features and functionality that's increasing their potential for pricing power.

And as they add these features, they can charge a small sliver of the value created. And as you grow in the market, the vertical software business is such that you gain a reputation. There's what's called referenceability, which allows you to gain incremental market share. When someone's making a purchase decision, they're usually calling over to a friend of their in the industry and saying, what do you use? And they say, oh, I use AppFullio. And so the product becomes kind of the standards in the market increasingly as you get bigger. And as long as you're treating customers well, you have these relationships for a long time. And so it's really a win-win sort of ethos and allows them to reinvest capital for the next decade.

It's interesting because they're obviously very customer-focused and not that Wall Street focused, right? Like there was a sense, I think in one of your shareholder letters, you wrote about how they would have an investor day and they wouldn't they wouldn't webcast it, they wouldn't have a transcript, they would have earnings calls and they would have no, no Q&A session in the earnings call. Can you talk about that? Because it seems like in the same way that you're having to be fairly stubborn and obstinate in focusing on the long term, on long term compounding of wealth, you're also favoring businesses that are kind of an ornery in saying to Wall Street, no, no, we're perfectly happy to suppress our short-term earnings because we're trying to build value over time.

It's exactly right. And I think that part of, I may be just drawn to it because I notice, I notice when someone's doing special, they don't always have to go in and broadcast it to Wall Street. Nowfolio certainly fits the bill there. You know, it's an extremely non-promotional culture. They don't provide long-term financial guidance. And that frustrates, you know, Southside analysts and many other funds because they basically want the company to do their work for them. They don't have Q&A on their quarterly calls, as you mentioned. The calls, you can listen to one of their calls. It's like 10 minutes of prepared remarks. And then they say, all right, thank you very much. See you next quarter. And people are left like, you know, what happened?

And for that reason, the stock has been largely misunderstood by the market for years. and the shares have also been closely held by a handful of long-term owners for a long period of time. You know, I think at one point it was more than 50% of the company was held by, you know, people on the inside. And that illiquidity and lack of promotionality creates a situation where the shares historically have traded with a fair amount of volatility. I was recently looking back at this and it was sort of interesting that the company has been public. for around 10 years now. And over those 10 years, it's compounded quite nicely. I think the long-term compound return has been more than 30% a year for a decade.

But over those 10 years, more than half of the trading days of those 10 years were spent in a drawdown of more than 20%. So it's like you hold this stock that's bouncing around, and more than half of the time, you're sort of experiencing this drawdown, which I think may. makes it quite difficult for people to own something like this. Let's take a quick break and hear from today's sponsors. No, it's not your imagination. Risk and regulation are ramping up,

and customers now expect proof of security just to do business. That's why VANTA is a game changer. VANTA automates your compliance process and brings compliance, risk, and customer trust together on one AI-powered platform. So whether you're prepping for a SOC 2 or running an enterprise GRC program, VANTA keeps you secure and keeps your deals moving. Instead of chasing spreadsheets and screenshots, VANTA gives you continuous automation across more than 35 security and privacy frameworks. Companies like Ramp and Riter spend 82% less time on audits with Vanta. That's not just

faster compliance, it's more time for growth. If I were running a startup or scaling a team today, this is exactly the type of platform I'd want in place. Get started at Vanta.com, slash billionaires. That's vanta.com slash billionaires. Ever wanted to explore the world of online trading but haven't dared try? The futures market is more active now than ever before and plus 500 futures is the perfect place to start. Plus 500 gives you access to a wide range of instruments, the S&P 500, NASDAQ, Bitcoin, gas, and much more.

Explore equity indices, energy, metals, 4X, crypto, and beyond. With a simple and intuitive platform, you can trade from anywhere, right from your phone. Deposit with a minimum of $100 and experience the fast, accessible futures trading you've been waiting for. See a trading opportunity, you'll be able to trade it in just two clicks once your account is open. Not sure if you're ready, not a problem. Plus 500 gives you an unlimited, risk-free demo account with charts and analytic tools for you to practice on. With over 20 years of experience, Plus 500 is your gateway to the markets. Visit Plus500.com to learn more.

Trading in futures involves risk of loss and is not suitable for everyone. Not all applicants will qualify. Plus 500, it's trading with a plus. Billion dollar investors don't typically park their cash in high-yield savings accounts. Instead, they often use one of the premier passive income strategies for institutional investors. Private Credit. Now, the same passive income strategy is available to investors of all sizes thanks to the Fundrise income fund, which has more than $600 million invested in a 7.97% distribution rate.

With traditional savings yields falling, it's no wonder private credit has grown to be a trillion dollar asset class in the last few years. Visit fundrise.com slash WSB to invest in the Fundrise income fund in just minutes. The fund's total return in 2025 was 8%, and the average annual total return since inception is 7.8%. Past performance does not guarantee future results, current distribution rate as of 1231, 2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income funds prospectus at fundrise.com slash income. This is a paid advertisement.

All right. Back to the show. Can you talk about this general topic of a willingness to hold stocks for a long time? Because obviously, your fund isn't that old. It's six and a half years old, but there are these stocks that you've held since the very beginning that I assume you'll continue to hold for many years. But when you look at a lot of the great investors, you've written in the past about how, for example, Ben Graham owned Geico from 1948, or Phil Fisher and Motorola from 1955, or Buffett bought the Washington Post in 1973, or Tom Russo bought stocks like Nestle and

1986. Or Lou Simpson bought Nike in 1993, or Charlie, I think, bought Costco in 1997. And they would just kind of hold. Same thing with Chuck Acre with his American Tower investment in 2002. Can you talk about the challenge of holding exceptional businesses when even the most exceptional businesses go through these periods that are pretty awful? Absolutely. It's something that I like to spend some of my free time doing, which is to reverse engineer the great investments of the great investors. And not just those periods where things are going great, but I'm really keen to understand those long stretches of time where nothing happens. And it's hard for you to sit on your hands. And you start to see everything else going up and you start to think, you know,

this, you know, my current companies are not doing so well. And you get seduced by greener grass over there. And I think so much about so much of holding a business for a long period of time is to be able to see what you have clearly. You know, Rumi has the quote where he says to be able to look at the thorn but also still see the rose. And so to have a balanced understanding of what you have and not to be swayed by these long periods of underperformance. You know, Costco is an example that I find to be quite striking because Charlie bought the stock, I think, in the early 90s, and he held it until his death. You know, he held it for decades. And within that period, you could look and say, wow, you know, I think the stock has compounded

in the high teens for multiple decades. And so it was a wonderful outcome. But there was a period, I think, between 2000 and 2010, where the stock didn't move at all. I think it was basically flat. And I wanted to understand this case because it's very few people would think of something like Costco flatlining for an entire decade. But really what happened was that they went into the late 90s and they were very ambitious. They thought they could grow new stores at 10 or 15% a year and their comps, you know, their same store sales would grow in the high single digits. And all of that would sort of roll up with operating leverage. you'd get to mid-teens, earnings per share compounding.

And, you know, that sounds great. But what happened is that in the early 2000s, they realized that they sort of over, they sort of overshot on their ambition, and they had to rein it in. So their store growth went down a little bit, and their same store sales were getting impacted by a number of, you know,

company-specific issues, including competition from folks like Sam's Club and Walmart. And the stock declined quite a lot, and it went from, I think, 50 times earnings in the late 90s down to 12 times earnings somewhere in the early 2000s, maybe 2003, 2004. And I would, you know, very few investment firms would be able to hold a stock like that for the whole way. Because throughout that period, it's so easy to say, well, Sam's Club is going to come kill them and this business has low margins. And you can concoct all

of these narratives to shake yourself out of the position. And I think what I once asked Charlie, what did he see that allowed him to own something like this for such a long period of time? And his answer, the first thing he did was actually remind me, don't forget that in markets where Sam's Club was opening stores across the street, we were actually cutting our prices. So you can imagine, you know, the very sharp Wall Street analyst is doing his channel checks and looking at what's going on in the stores. And he would find, that this business doesn't have any pricing power, because everywhere that Sam's Club's coming, they're cutting their own prices. So what kind of good business is Costco if they have to cut their

own prices? But of course, these were all temporary dynamics. And Charlie's answer was that the product quality was improving. The management was ethical. You know, the culture was meritocratic. These are all root qualities that wouldn't ever have shown up in any spreadsheet or in any you know, fancy research report. But the root qualities were what allowed him to own the stock for multiple decades and never get shaken out of it. Yeah, it's really interesting. I was reading your account of your dinner with him, which I think was just a few months before he passed away at the age of 99 back in late 2023. And I was really struck by the fact that all of the things he talked about that enabled him to stay in Costco for all those years were really qualitative, right? So unwavering

commitment to customer trust or employee loyalty or product excellence or ethical people or meritocratic culture or whatever. So it really reinforces what you were saying before about trying to look for qualities that aren't necessarily expressed in a spreadsheet, but they do exist, but you have to be attuned to recognizing them. And you said something really nice in one of your shareholders where you discussed this. You were talking about the difficulty of going through these periods of stagnation for a stock. And you wrote, this may be precisely why attractive long-term returns are available to those of the different temperament orientation and structure. I think that gets at something really important that you need this kind of intellectual understanding of why you

want to be patient. But there is an element of temperament that, you know, as Charlie would talk about, the ability to defer gratification, that if you don't have that deferred gratification gene, it's really hard. But then there's also this issue of structures. that you actually have to have structured your investment firms so that your shareholders will allow you to be long term, which I think almost nobody has been able to do. Like that, you know, you have like Josh Tarasov has like there. You have to be kind of slightly ornery to sort of say, well, I'm just not in the asset gathering business.

And so I'm probably happy to sit and just quietly compound money. Yeah. I think it's a really tricky problem. and I think so many of these questions with investment, they are what's called a diversion problem. In the 1970s, there was this gentleman named E.F. Schumacher, and he wrote a few books that I really enjoyed over the years. Schumacher himself was actually a protege of John Maynard Keynes. And one of the books he wrote was called Smallest Beautiful. Another book that he wrote, that he wrote is actually called Guide for the Perplexed, which of course is paid homage to the same

title by Maimonides. Yeah. And, you know, in Guide for the Perplexed, she talks about the difference between convergent problems and divergent problems. And a conversion problem would be like one where the solutions to the question increasingly converge on a single answer. So classic example would be, you know, how should we create a two-wheeled, human-powered means of transportation? And so people will put solutions forth, and increasingly you'll learn that it's the bicycle. And the bicycle has been the answer, the conversion answer for quite a long time. Divergent problems are different. Divergent problems are those where they don't converge on a single solution. In fact, many solutions become polar opposites. And the classic example here

would be asking, you know, how should we educate our children? And so one group of people might say, well, you should give the children immense freedom so they can explore and nurture their own interests. And another group of people might say, no, you need discipline. You actually need rigorous discipline and following the rules, and that's how they'll learn. And so at the extremes, you've created a divergent problem where the answer to how should you educate our children is either freedom or discipline. And you're sort of on two different ends of the spectrum. And, you know, I'm not sure that this idea is all that new. I think Aristotle said it best when he said that every virtue is in the middle of two vices. But so much of investing sits at this point, you know,

to your point about urgency versus patience, about working hard versus letting go, about, you know, trust versus skepticism, concentration versus diversification. you know, generalist versus specialist. All of these questions, you sort of learn that you need both and you need them in some kind of harmonious proportion, which only intuition can tell you, you know, how much of each you need. And so with something like building an investment firm, it's really, of course, you need some capital to start. So you can't just go off and start, especially when you're young in most cases. But if you spend, all your time doing that, then your actual investment performance will suffer. And so there's this,

there's this line that needs to be found between the two. You know, another one is to have a network versus to be independent. That's another classic divergent problem that one has to solve when they're in this investment business. Yeah, well, you and I have talked a lot about that in the past because you obviously spend a great deal of time, or have spent a great deal of time over the is chatting with friends like Chris Begg and Josh Tarasoff and the like, these really smart people about investing. And there is some crossover in some of your holdings and your approach. And yet at the same time, I remember we were talking about Carvanna at some point. And you said, yeah, I didn't tell them I was investing in Carvanna. Can you talk about that? Because Carvanna is a really

interesting example of something where you actually took a different approach that you do have these really exceptional long-term businesses, but then sometimes you'll buy something where there's tremendous asymmetric upside potential, but that it's pretty hairy and it's not something you really want to talk to people publicly about. So again, it gets at this kind of conflict between having a network where you share ideas and actually being quite secretive because you don't want people to judge you and you have to defend yourself. Can you talk about Cavanagh through that lens? Yeah, well, first of all, I'll say, you know, I'm incredibly grateful to have a small circle of friends in this work, people that I respect enormously, not just for their talent. You know, some are peers, others are mentors. And having a circle like that can be incredibly valuable. You know, it gives you access to thoughtful perspectives. It can create a healthy intellectual tension. It sharpens your own thinking. But like we were just saying, like almost, everything investing, this one, there's a paradox to manage.

Meaning, if you rely too heavily on a network, you risk groupthink and you risk outsourcing your judgment. And that robs you of the conviction that you need when markets become volatile. And I always think of that old Templeton line where he says, the best, I think he said that the best performance is produced by a person, not by a committee. But on the other hand, if you isolate yourself completely, you risk missing important perspectives and you risk falling in love with your own ideas, creating an echo chamber. And so I try to live in that kind of in-between place, you know, what in Buddhism they might call

the middle way, where you're open to, you're open and receptive, but at the end of the day, you're trusting your own judgment, your own instincts. And so one of the most helpful evolutions on that point is letting go, for me was letting go of what, you know, might call investor idol worship. Because when you're just starting out, it's very natural to sort of subjugate your own intellect because the people that you respect, you put them on a pedestal to assume that becomes they're famous because they have a great track record or manage a large fund. You know, they must know better. And of course, it's good to have enormous respect for those who come before you, but usually you have to learn the hard way that investment judgment is deeply personal. And I notice that all the time, even with people that share an almost identical philosophy where it's like we're

finishing each other's sentences in many cases, we still end up on disagreeing all the time about specific businesses and position sizing and how to weigh certain kinds of risks with a specific company. And so investment judgment is deeply personal. And I think, you know, Carvana is probably one example of this. You bought it. I think that, you know, it had obviously had this amazing period of expansion and then it got kind of crushed in, I think, 2022. And a lot of people thought it was going bankrupt. And the stock, I think, fell about 93% before you bought it. You told me a great story at one point about someone saying to you, you know, how do you avoid things like Carvanna? and having to kind of keep your mouth shut because you were quietly buying Carvana.

Talk about the discomfort of that, of like being willing to go buy something like that. Like, what was it that you saw in it that embodies this kind of, this sort of slightly more speculative part of your portfolio where you're willing to take things where there's less certainty and less of a guarantee of excellence? So I'll preface this by saying my preference is always for a large, large holding in something where the risk of impairment is basically deemed remote. And I would prefer the whole portfolio to just be, you can participate in a tax-deferred way in low-risk compounding for many years. You know, that's much better. But every once in a while, you may find something where

you can have potentially the same impact as a large, successful position. But even when the position size, the starting position size is sort of immaterial. And I will occasionally own something where you have a smaller position and it's deemed to be highly asymmetric. You know, Warren Buffett has his rules of investing about, you know, don't lose money, don't forget rule number one. And I might add it a little addendum in there that says if you must lose, if you may lose money, just make sure it's not that much. Make sure it's just a little bit. And stylistically, I think on this point, I've learned a share amount from people like Bill Miller and, you know, another good friend of mine is Quincy Lee, who's done some of this over the years, being able to sort of migrate

in and out different styles. Even Charlie Munger, you know, when I spoke with them, she's done this to a certain degree. He had his large Costco holdings, but he also, you know, bought something like Tenneco in the early 2000s, which was a distressed auto supplier, you know, not a good business, but he was able to buy it at a very low price and sort of participate in this big outcome. In terms of Carvana, the story there really began when I was working with Lou because we were shareholders of Carmex. And I think at one point we owned around 5% of Carmex equity. And I still remember being in Chicago, walking down Michigan Avenue, listening to the Carvona Road Show and just being completely struck by the thoughtfulness and ambition of this management team. And at the time, my own sort of investment palette was not really geared towards companies that

were so early in their growth, you know, growing hundreds of percent, burning so much capital. And so I decided to just watch, watch and see from the sidelines. And over the next few years, they really executed flawlessly. They extended into new markets. They turned their inventory faster. They increased delivery speeds. They improved profitability in specific codes. cohorts, they created like an in-house infrastructure, in-house logistical infrastructure that

was vertically integrated, first party. And they could create, you know, scale economics and sort of create this much better customer experience in the used car market. And while I was working with Lou, a colleague of mine, Orman, a good friend of mine, he created this web scraping tool. It was sort of an early web scraping tool that could compare apples and apples, cars on Carvana versus Cars on Carmex. And it was clear that Carvano was underpricing the industry by like $1,000 per unit. And that's significant for a product where the gross margins are like $2,300 for Carmex over the years. And so it felt like in a market that transacts, you know, 30 to 40 million used cars per year,

and this business was poised to compound and had this long reinvestment runway and these people were very focused. And so I watched from the sidelines as the stock front rose 20 times in just a few years from there. And then, you know, in 2022, a combination of bad luck and mis-execution basically brought the business to a sudden halt. They made this big acquisition. They took on a lot of debt in order to do it to sort of finance themselves to sustain this rapid growth rate. And the mistake happened, the bonds, when the mistake happened and the business sort of turned the other way, the bonds got down to 30 cents. The stock declined by, you know, 90 something percent. By the time we bought our first shares, the stock had declined from $370, $370 to $25. And I think the short interest at the time was 75% of the free float. So everyone thought basically this business was going to go bank. And actually, you know, my timing was not so great because I bought the stock at 25 and just a few months later it had gone to $3.50 or something. So it went down by another 85% or so after I bought it.

And during this period, I definitely was not talking it up to people that I knew. I was talking about it. So I would bring it up just to talk about it. I wanted to see if there was, there were different perspectives. But I didn't want to, I didn't want to say that. I liked it and I didn't want to say that I owned it because there were certain times during this ownership where the stock would be up or down, you know, 70% in a day because of some headline. And what I wanted to prevent myself from was having a lot of inbound inquiries from people, even though I want to be helpful. I knew that it would be challenging for my psychology to try to respond and defend. It would create commitment bias. And really, I think the moral of

story is that stocks can do anything in the short term, you know, literally anything. And to spend a lot of time trying to predict if or when they might go down by a lot, I think has been challenging. I'm curious to know how you handle the emotional, psychological side of the game of investing, particularly as a very concentrated investor. I think you own about nine stocks. And you'll often have maybe 90% in six or seven of them. And so obviously there are periods where it's really volatile. I mean, it gives you more of a chance to outperform, but also more of a chance to underperform in certain ways. And, you know, in, I mean, your returns have been excellent since, since you started the fund. But you did have that year in 2022, where I think you were down about 42%.

And then, you know, the next year you come. One percent. Yeah. And then the next year, you're back up about 70 percent. And I'm, and I'm just wondering, I know you meditate. you always seem to have a reasonably chill kind of temperament to me. I'm curious how you actually, what you've done in practical terms to deal with just the sheer emotional intensity of the game. So I think maybe it's two things. The first is, as I mentioned, it's really studying history. It's recognizing that these periods are normal.

And so when they come, you shouldn't be surprised. You should just know that every investor has had their due. over a 30, 40, 50 year record. Every investor gets their time. And so when it came in 2022, it didn't last that long. But I was mentally preparing for it to last for five or 10 years. I just knew that every investor has these periods. And so buckle up.

That's what was going on in my mind. So part of it, I think, is just intellectually understanding that it's normal and constantly reminding yourself of it, constantly reminding your partners of it. it's easy to become complacent when you notice your capital accounts, it's just rising, you know, month after month to think that it's, you know, this game is easy. And I think that these, these moments where things are going really well are an opportunity for humility. And when moments, when the moments are going poorly, it's an opportunity for trust to sort of recognize that this is normal and to trust, to trust the process. In practice, I try to, you know, I won't

claim to have it all figured out, first of all, but I try to find some harmony between different aspects of life, whether that's work, family, health, you know, inner life. That may mean exercising, that may mean making space for meditation. I think, you know, my family, which I joked about in the beginning, has no interest in business, is sort of a blessing in some ways because spending time with people that you love who have absolutely no idea what the stock market is doing can be great. And those things sound trite, but they really do restore a sense of perspective and a sense of proportion to this whole process. I was very struck also in reading your shareholder letters. There's a lovely section in one of them, I think, about the willingness to

surrender in the face of uncertainty, which is sort of philosophically very appealing to me because I spend a lot of my time worrying about uncertainty. I'm going to quote this because it's kind of really elegant. You wrote, surrender also demands that we embrace uncertainty. To surrender is to accept that markets are fickle and anything can happen year to year. The unknown cannot be tamed. Attempts to control or predict it will only drain our limited resources. There will be years when our portfolio experiences sharp declines, likely for reasons few expected. Rather than fearing this inevitability. My recommendation is to surrender to it. And then you talk about how for you, part of the meaning of surrender is actually to stay fully invested and not trade around your

core positions and just focus on the quality of the businesses that you're invested in. I think that's such an interesting insight. I've been thinking about this a lot recently because I, you know, there's a part of me that's sort of a pessimist that I always think of that line from Yates where he says things fall apart, the center cannot hold, mere amicies loosed upon the world. And I always have this sense when everything's been going well, oh my God, it's all going to fall apart. And so there's a part of me that having ridden this bull market for the last 16 years, sort

of keeps thinking, I really don't want to give back 50%. And then the last couple of weeks, I've really been thinking about this, probably after a conversation with Nick's sleep, where he said, you know, just don't fiddle, William. Just leave it be. If you give back 50%, you'll just buy cheap stuff. And I'm like, yeah, why am I even worrying? Like I, instead of trying to fight this thing or predict this thing, I should accept the fact that my entire approach to investing anyway is built on taking

advantage of disruption. Like, why am I, why am I bracing with this sense of pain and fear at the prospect of disruption when it's inevitable because we live in an uncertain world? And you should just sort of set yourself up to kind of deal with it. And so you'll survive it. Does that raise any thoughts for you? It's such a great point. And the more that I've thought about this, the point on surrender, I think surrender goes hand in hand with trust.

In some sense, when you, the reason why we can all intellectually say that it's normal to go down 50%, but we don't want it to happen. It's because we, you know, in some ways we don't trust that will do the right thing when that happens. you know, there's a lack of trust in the self. And I think that the experience in 2022 was illuminating in some ways because on one hand, in 2020, 2021, it was as though everyone's a long-term investor, you know, everyone wants to own these stocks for 10 years because month after month that's just getting richer and richer and richer and people are very excited. But then in 2022, you could just see the time horizons shrink. And suddenly, everyone wants to learn a lesson. person. Everyone is, you know, I shouldn't have owned this. What was I thinking? And in some cases,

those were true. But in other cases, it was merely a reaction to price action. And ironically, I think that had we not had 2022, our returns since inception were actually be worse. Like, if you just took Rumi's portfolio at the end of 2021 and just wrote it for the expected returns that I thought we were going to get at that point, it would have been okay if it was just linear up to the right. It would have been nice and comfortable. But I think the opportunity that a down market gives you is the ability to coil the spring because you can start, you can recycle your capital. You can sell things that are down 30, 40 percent to buy things that are down 70, 80, 90 percent. And that actually benefits you over the long run. And that's why Warren Buffett and Lou Simpson and

so many people over history have tried to make this point that volatility is your friend. It's the friend of the investor. And the hang up, I think, is that even if we know that, do we trust our ability to make the right decision when that moment comes? And I think if you trust that when we're down 50%, that I'll know what to do, then what's there to fear? You can just sort of let it come. Yeah, it's funny because the reality is I look back to 2008, 2009. I didn't sell anything. I bought some stuff. I didn't, I didn't, I didn't, I didn't panic, even though I lost my job in the middle of the period as well. And then in 2022, I think I didn't sell anything and I bought Berkshire like four times. And it's,

you know, I'm not trying to say this to in self-congratulation. It's like, so why am I so afraid of like a repetition of pain when actually I sort of, I'm kind of okay in, in periods of pain. I think because I'm sort of, to some degree, a pessimist who always sort of expects it. And so I'm positioned to be able to take advantage. I don't know. So I mean, some of it is just managing our own kind of weird psychology, I guess. Right. Absolutely.

I think managing the psychology, structuring the environment, you know, the experience in 2022, I hate to put it this way, but it really wasn't a big deal. It really wasn't. It was, it just felt like a normal run of the mill time. and I remember the day that Carvana hit $3.55.5. I was out on a hike that morning. And it really just, it wasn't all that big a deal. Now, if it was a huge position, maybe it would have felt like a bigger deal. But it started out as a smaller position and I sort of added it to it on the other side. I added to it at 10 and I added to it at 40. And so on the way back the other way, I made it in a bigger position. So yeah, I think this, this is a difficult. balance to find, you know, between sizing something to the point where it becomes psychologically difficult versus small enough where you can sleep at night but still have an impact on the portfolio if things work out. You said something very interesting to me recently when we chatted

a few weeks ago as well where you talked about avoiding fear-based decisions. And you were saying that you, with something like Carvanna, for example, you trimmed out out folio to buy Carvana and then later Carvanna soars and you trimmed Carvanna a little bit. But you were saying because you are always running pretty much fully invested, you're not really making fear-based decisions. You're selling something because you find something that you love more. Can you talk about that? Because there's a really interesting nuance there, I think.

That's not something we usually discuss. Yeah, someone was asking me recently, how do you sell? And it's the classic difficult question to answer. And what just emerged was that I sell based on my cell decisions are like a love versus fear question. And suboptimal cell decisions, in my opinion, are fear-based decisions, which are, you know, I had a 10% position and now it's 12%. That's too big. What if it goes down? I'm going to pare it back to 10. This kind of thinking happens all the time in the name of sort of risk mitigation and in the name of rebalancing the portfolio. And if that's the case, you sort of never get the full benefit of one of these great investments.

So what's a love decision? A love decision is something where you feel compelled. You feel sort of called to own more of this business over here. But because you run fully invested, you have to get the capital from somewhere. And it's much more of a positive decision rather than a negative decision. A negative decision says, this is too big. I am scared. What if it goes down?

a positive decision says, I really need to own more of this because it's so great, I got to get the capital from somewhere. And I think that, you know, sell decisions come in a few flavors. You can either sell because you made a mistake, which happens, of course, from time to time. You can sell for opportunity cost reasons, which is what I'm talking about here. There's opportunity cost of capital. You'd prefer to own one business over the other. There's also the sell decision, which comes when, something is sort of egregiously overvalued, meaning, you know, you may not make money for a long time. You may have negative returns for a very long time from here. I'm not sure that that has ever happened in my experience over these first six years. So that's super overvaluation. I haven't seen that yet when I'm studying these specific businesses. So really, I think 80 plus percent of the time, it's an opportunity cost, kind of a calculation.

I was struck when I was looking at your letters the other day that you talked about surfing a couple of times in, you know, you often have these quotes. And there was one quote at the end of your January 20205 shareholder letter from John Cabot Zinn, this great meditation teacher who said, you can't stop the waves, but you can learn to surf. And then at the end of your January 2020s letter, you had a quote from William Finneger in the great. New Yorker writer who wrote this book called Barbarian Days, a Surfing Life, which has a longer quote, but I'll read it because it's kind of cool, where he said, surfing always had this horizon, this fear line that made it different from other things. You could do it with friends, but when the waves got big, when you got into trouble, there never seemed to be anyone else around. And then he said, the waves were the playing field. They were the object of your deepest desire. At the same time,

they were your adversary, your nemesis, even your mortal enemy. They were your refuge, your happy hiding place, but also a hostile wilderness, a dynamic in different world. And I was curious, given that you have both of these quotes about surfing and that you live in California, like, what's the parallel between investing and surfing and managing a fund that's been helpful to you to think through? Yeah. I will claim to be a great surfer.

I love to surf. I do think that there are plenty of parallels in surfing and investing. Surfing really demands a surrender, this idea that you're not going to predict what's going to happen, but you have to sort of be open and receptive. And, you know, I had one experience actually down in Costa Rica with Chris Ney. And there was a lesson, there was an investment lesson which came, ironically when I was out there waiting for a wave and I saw one coming and I sort of look to my left and look to my right and being not a great surfer I'm always looking for someone to tell me this is the right wave to take and I was looking and everyone was sort of focused on their own there was everyone was playing their own game they were sort of in their

own heads and I was waiting for this validation they wanted someone to tell me this is the right one and I just end up deciding that this is a great wave and I took it and it ended up being a lovely ride, but it really sort of reinforced this idea that no one's coming to save you, particularly in investing. And that idea of investor idol worship, it's easy to think that by following someone else's path, by investing in the way that someone else invests, that that's the right path. But ultimately, it comes down to you and you have to make your own decisions and you have to trust your own judgment and you have to develop your own discernment. There's no substitute for that.

Before I let you go, we've talked a bit about the poet Rumi. We've mentioned a few quotes from him along the way. It was an unusual decision in many ways to name the firm after a 13th century Sufi mystic when you founded the firm in 2019. How has he been a really important figure for you, both as an investor and in life. And I guess this is related to the general sense of why it's been helpful to you as an investor to have this kind of deep spiritual life where you're thinking about things like the trust and surrender and a willingness to into your periods of contraction and getting beneath the facade and seeing the underlying reality, all of the sort of things that Rumi talked about.

you know, Rumi, as you say, he was a 13th century Persian mystic. And one of the things that I always find fascinating about him is that in the late 90s, early 2000s, Rumi was actually the best-selling poet in the United States. So he sold more copies than Shakespeare, Homer, you know, Dante, Milton, you know, take your pick. And it raised a question, which is, what are all these Americans doing reading the poetry of a Persian mystic from 800 years ago? And I think that part of it, I think part of it is that Rumi's ideas are universal.

He speaks to something timeless in the human condition, which is this deep yearning to see beyond the surface and to discover meaning beneath appearance. And one of the mainstays of Rumi's teaching, as you say, is this constant sort of provocation he provokes you to see past appearances and ask what's actually real, what's going on, what's the truth. And, you know, he was also astonishingly prolific. He composed, I think, 60,000 lines of verse, something like that. And yet he wasn't even a professional poet.

You know, I think he would laugh at the idea that people are now calling him a poet. He was a spiritual guide, and he had disciples, and many of his poems were actually spoken, you know, spontaneously when he was in this ecstatic, meditative state. And some of his, you know, some of his companions would write things down that he wrote. And as to why I chose him as the namesake of my partnership, you know, what I think makes him timeless is his ability to embed deep truths about existence into the most ordinary everyday imagery, whether it's a garden or the sun or a candle or a moth. He points you from the obvious and the visible towards the invisible and the essential. And that way of seeing always resonated with me as an investor.

Because investing at its core is an act of perception. It's about seeing beyond the narrative and what the news is talking about and what other investors are talking about to try to grasp the essence of the business. What is it that actually makes it tick? And Rumi, you know, that's all Rumi was about. And is there a favorite line or saying of his that you live by? Like, you know, before, for example, we were talking about about this willingness to live with paradox and contradiction. I was thinking of this line of his that you sometimes quote where he said life is harmony among opposites, which seems like a lot of what you're doing is trying to find harmony between these things like, you know, being aggressive and having a sense of urgency and being patient and

slow moving and the like and having a circle of friends you talk to, but also thinking for yourself. Are there things like that that really, in terms of your inner monologue day to day that you live by because you were taught them by Rumi? You know, there's one quote of his that is one of my favorites, which is, if you are irritated by every rub, how will your mirror be polished? And, you know, he's talking about, on one hand, he's talking about something that's probably pretty obvious to everyone, which is that if you take everything personally, if you're sort of oversensitive, then, you know, you're missing the lessons, you're missing sort of the teachings of these moments that irritate you. But what he is actually talking about was the way that our egos distort our ability to see clearly. So what is it about a mirror? You know, in the ancient world, mirrors were not made of glass.

They were actually made of bronze. And the craftsman of those years would, you know, I think for tens of thousands of years, 10,000 years they were probably made this way, where a craftsman would combine copper and tin and create bronze. and before glass mirrors existed, you would just polish the surface of these mirrors and polish it and polish it and polish it until the bronze became reflective. And if the metal that you were polishing was left uneven or corroded, then when the light came into the mirror, it would sort of scatter in every direction.

It wouldn't actually reflect clearly. You couldn't see clearly. And that to me, this metaphor about us as mirrors, human beings as a mirror that needs to be polished because we're essentially, we start out as this base metal, which is not reflective and is not beautiful. But with polishing, you can sort of reflect, you can sort of reflect the reality. That is such a precise metaphor for the human condition. And that unevenness and the corrosion of an unpolished mirror is essentially akin to the distortions that are caused by our own egoic perspectives.

when we when we need to appear superior, when we fear being wrong publicly, when we fear public humiliation, when, you know, our perception of reality becomes worked and we stop seeing things as they truly are. And I think this has plenty of parallels to investment because when we're making decisions from that place of fear and ego, then of course we make these terrible decisions. So yeah, I mean, that's my roomy quote. Yeah, I love that. I want to One of the reasons why I love talking to you is that I think I tend to have this sense that investing is like this beautiful subset of worldly wisdom, as Charlie would say, and that it sort of includes everything. And it's just this lovely microcosm where you can, you know, you can study like

human nature and psychology and philosophy and spirituality. Like it's all part of it. And I was reminded when we talked last time, you quoted a conversation you'd had with, I think, the author of Vaclav Smil, who when you told him what you did, he said, oh, you're a money massager. And actually, I think this conversation is proof that you are much more than a money massager. Yeah, he, I called him about, you know, I was doing some work on the renewable energy business. At the end of it, we had this long conversation and he said something like, so what is it that you do again? And I said, you know, I'm an investor. And he said, ah, so you're a money massager. And I think that, you know, it's so, it's, it's classic that the perception of what this business is is like we're sort of sitting around

just massaging this portfolio of securities. It's not a real profession. I don't feel like it is actually a real profession. It's sort of a beautiful means of exploring your curiosity and hopefully serving people while you do it. On that note, it's just been a real delight chatting with you. And I hope I'll see you soon whether, well, we'll definitely see each other in Omaha, I hope. But hopefully I'll see you in New York before then. Absolutely. It was a pleasure. Thank you. Thanks so much. It was real delight. All right, folks. I hope you enjoyed today's conversation with Nemeshaye. As we draw to the end of 2025, I wanted to take the opportunity to wish you a very happy holiday and a wonderful new year. I also wanted to take the opportunity to thank the fabulous

team at the Investors Podcast Network, which makes it possible for me to host this podcast. That includes Bianca, Searle, Camille, Katrina, Noel and Jasmine. And I'm especially grateful to my terrific editors, Jadilla Lampa and Christine Romero, who not only do an excellent job editing the audio and video versions of the podcast, but are also unbelievably patient in putting up with how late I always am with my deadline. So thank you for your tolerance, your talent, and your kindness. I really appreciate it. It's also a total pleasure to work with my friends Stig Brodison and Preston Pish, who co-founded the investors' podcast network more than a decade ago, I couldn't have been luckier in becoming partners with them. They've just been a total delight. So thank you. I'm

really grateful. And it's been fantastic to get to hang out in the last year with my fellow podcast hosts, Clay and Sean and Daniel. And I've also been particularly fortunate to get to work closely with my friend and fellow podcast host, Carl Grieve, who's been an invaluable partner in helping me to create the richer, wiser, happier masterclass. He's just been a lovely and hugely capable partner on this project. So thank you. On a separate note, I'm excited to announce that I'm about to launch after many delays and much pondering, a new YouTube channel. You can find it by looking for this handle, apparently, which is at William Green, Markets and Life. And in the coming weeks and months, I'll be sharing pretty regularly some of my favorite video clips from interviews that I've done with many great podcast guests.

So these are people like Rick Reader, Tom Russo, Monich Pabry, Joel Greenblatt, Ray Dalio, Samantha McElmore, Chris Blumstran, and many others. And I think I'll also share some clips from my appearances on other people's podcast. So hopefully there'll be plenty of interesting stuff there that if you're deeply interested in this whole topic of the intersection between investing and life and how to think and how to live, you'll find helpful and life enriching. I'm really grateful to my friend and collaborator Weld Royal, who will be helping to run my YouTube channel. Weld has been an invaluable partner over the last year.

She officially is my chief of staff, although given that I am the only person on staff, I'm not sure really what that means. But she's just been great to work with, and I'm very grateful to her. And also, I'm really grateful to Jeremy Stickney, a renowned YouTube expert, who's given me and Weld, a lot of great advice that will attempt to follow. And my wonderful daughter, Madeline Green, has helped with the design of the YouTube homepage for this channel. and also designed the thumbnails for all of the videos, I think. So it's just a real pleasure to work with your own kit. What could be better in life? I think for me anyway, whether it's as good for her, I don't know.

Anyway, I hope you'll check out this new channel, which as I say is at William Green Markets and Life. And feel free to subscribe. And likewise, feel free, as always, to follow me on X at William Green 72 and to connect with me on LinkedIn, if you like. And do let me know how you're in. during the podcast, I'm always really delighted to hear from you, especially if your messages are full of praise and warmth. If you don't like the podcast, just keep it to yourself or mention it on YouTube.

That's fine. And in any case, thanks so much for listening and take good care and stay well. And I wish you and your family a very happy, healthy and prosperous, joyful new year. Thanks for listening to TIP. Follow richer, wiser, happier on your favorite podcast app and visit the Investorspodcast.com for show notes and educational resources. This podcast is for informational and entertainment purposes only and does not provide financial, investment, tax or legal advice. The content is impersonal and does not consider your objectives, financial situation or needs.

Investing involves risk, including possible loss of principle, and past performance is not a guarantee of future results. Listeners should do their own research and consult a qualified professional before making any financial decisions. Nothing on this show is a recommendation or solicitation to buy or sell any security or other financial product. hosts, guests, and the Investors Podcast Network may hold positions in securities discussed and may change those positions at any time without notice. References to any third-party products,

services or advertisers do not constitute endorsements, and the Investors Podcast Network is not responsible for any claims made by them. Copyright by the Investors Podcast Network, all rights reserved.