Nima Shayegh on Roots and Branches, Lou Simpson, and Surrendering to Uncertainty

Nima Shayegh

Show: Richer, Wiser, Happier

Episode: https://www.theinvestorspodcast.com/richer-wiser-happier/a-soulful-path-to-stellar-returns-w-nima-shayegh/

Cleaned and reformatted from published transcript or auto-generated captions — punctuation added, filler removed, restructured for readability. Not verbatim. For exact quotes, refer to the original.

Contents

    Growing Up Between Two Worlds

    William Green

    I wanted to start 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 swaggering hedge fund manager. What kind of environment did you grow up in, and how did it shape the person you would become?

    Nima Shayegh

    My parents came to the US — to Southern California — following the Iranian revolution, and like many Persian families of that era, they had to start from scratch. I was the first generation to be born and raised in the US. My family is full of intellectual curiosity. Many people were educators. Multiple people have authored books. My family has a handful of talented musicians. Almost no one was all that interested in business. Dinner conversations would migrate to philosophy or classical music, definitely not interest rates or the stock market.

    The initial spark of interest in investing was 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. There's a particular discomfort when you have no understanding for something that is reshaping society. You don't know why it happened; you don't know what's going to happen. I made it a priority to learn more, and as I started to, it felt like a natural extension of my temperament and interests. Ironically, it's not all that different from those dinner conversations about literature or poetry — really, they were about observing human nature and seeking the essence of things.

    In Persian culture, there's a running joke that you can be anything you want as a profession — any kind of doctor or engineer your heart desires. When I decided to become an investor, there wasn't much precedent. I would tell someone in my circle and the response would be something like, "So you want to be like a bank teller?" I would say I wanted to invest in the stock market, and you could see concern on their face, as if I'd confessed to a gambling problem. But from the very beginning, investing felt like the ultimate intellectual adventure — a microcosm where you could practise your discernment, creativity, temperament, and reasoning, and get this objective feedback loop. It was incredible that you could professionally pursue your natural curiosity.

    William Green

    We were chatting before this conversation about your high school years and that you were a somewhat eccentric, independent-spirited student. Can you talk about that? It seems like in some way that's something all the best investors have in common — this willingness to diverge from everybody else.

    Nima Shayegh

    It's a little embarrassing when I reflect on it, but also a little funny. One of the commonalities looking back is that it was always very difficult for me to buy into something my heart wasn't fully in. I remember that once you turned 18, you could actually just go sign yourself out of school without a parent note. On many occasions, when I was not interested in what we were studying, I would sign myself out and leave. Ironically, I would go to Barnes & Noble and read something far more fascinating. That natural inclination to go deep in areas I was very interested in was a foreshadowing of investing for sure.

    William Green

    I was pretty similar. I went to Eton, where it was very disciplined — if you showed up late, you were in trouble. In my last year, I was only taking three subjects, and I just decided my history teacher was boring, so I didn't show up to history anymore. I was going to teach myself. As a journalist and writer, that's a really useful characteristic — just say no, I'm going off and doing my own thing. I think it's one reason I was fascinated by great investors: there's an element of diverging from the crowd and deciding to crack the code for yourself.

    Nima Shayegh

    I think it's definitely true that this willingness to think for yourself was hammered into me as a child — not with investing specifically, but this tendency not to accept what is the commonly held view or mainstream narrative, but to try to figure out what's actually going on. My parents instilled that early.

    Roots and Branches: The Case Against Quantification

    William Green

    You went to UCLA and studied mathematics and economics. So part of you was very left-hemisphere oriented — convinced that mastering maths, statistics, and economics would give you the skill sets to understand reality. My sense is that you gradually came to realise that comfort in numbers and logical reasoning was not going to cut it. Can you talk about that evolution?

    Nima Shayegh

    The way it has come together for me is this idea of branches and roots. Rumi has a quote I love: "Maybe you're searching among the branches for what only appears in the roots." That quote has a lot of significance for investors. When I reflect on the investment industry broadly, I notice that it has swung so far in the direction of quantification — expert calls, credit card data, web-scraping technology, extraordinarily powerful tools that measure and predict. And yet 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 very long, despite the fancy tools, despite the incentives, despite working really hard.

    I started out as really technical, very focused on mathematics and quantification. But it felt like I was lost in the branches and missing the roots. The branches are what everyone can see and measure: last quarter's margins, this week's unit growth, next month's inflation print — quantifiable pieces of information devoid of context. The roots of a business are the qualitative forces causal to the future economics: the motivation of management, the culture of the company, the quality of the product, alignment with customers. None of that shows up on any spreadsheet. You can't model it, you can't quantify it, but these are actually the most real parts of a business.

    Lou Simpson used to always say that all investing is figuring out the future economics of a business. That statement sounds simple, but it creates an extraordinarily high bar. Most investors fixate on the current economics — the current branches. Every once in a while, you can get a deep sense for what the future economics might be, and in those cases it's usually because you have a sense for the roots. The challenge — and the opportunity — is that the roots require intuition. Suggesting that stock market investing requires intuition makes many people uncomfortable because it feels subjective and squishy. But it's precisely those qualitative, invisible factors that live upstream from the financials that everyone else is focused on.

    William Green

    You wrote a piece called "Roots and Branches" — originally a speech you gave at Columbia in Chris Beg's class in 2023, then a shareholder letter. You quoted Robert Pirsig talking about pre-intellectual awareness, and you talked about this ability to apprehend essence being supra-rational. Can you expand on that? There's something pre-intellectual in it — Chris Beg and I have talked about this too, this sense that we have an embodied ability to tell whether something is true.

    Nima Shayegh

    In most cases the roots of a business are too hard to tell. And I think the first thing to note is that you only really want to swing when it's pretty obvious. In Persian, we have a very old expression — probably more than a thousand years old — cheshm del, which literally translates to "eye of the heart." It's this idea that the heart is more than the organ that pumps blood; it's actually a faculty of perception, capable of grasping non-material truths. Whether we like it or not, we live in a reality that is qualitative.

    Intuition is sometimes framed as a superpower you have to develop. I think it's less about developing a superpower and more about clearing away everything that is muddying our perception. All human beings have the capability to discern and perceive non-material, qualitative truths — things like trustworthiness, sincerity, ambition, beauty. These are qualities you can't model or quantify, but there's something pre-intellectual that can grasp and recognise them when you're in the face of them.

    William Green

    You had a lovely example of this — you were talking about driving to Costco one evening in a Tesla in full autonomous mode. Can you describe that?

    Nima Shayegh

    It's hard to explain what makes this product special, but overwhelmingly when I take my in-laws or parents or friends who are unfamiliar, there is this moment of awe. We were driving to Costco one evening and I clicked the button — the car navigated through construction zones, pulled over for emergency vehicles, got on the highway and off the highway. I hadn't touched the steering wheel or pedals the whole ride. Then it pulled into the parking lot, skipped some open spaces to look for a better one, and just pulled in perfectly. I was thinking: this is almost a miracle that this exists. Very few people understand the power of that technology without having had a direct perception of it. That is one example of coming face to face with quality. The first time you touched an iPhone, or got same-day delivery from Amazon — these customer experiences tell you something about the quality underlying them.

    William Green

    You had a lovely word for it — you and an investor friend talked about the quality of "blown-away-ness."

    Nima Shayegh

    Yes — being blown away. It's not an industry term you can quantify one out of ten, but it tells you a lot about the quality of what you're encountering. It's as simple as your favourite restaurant: you have a perception that tells you when the quality has either improved or deteriorated. Something within you knows, and often it's emotional, physiological. We all have this commonly held dogma that you're supposed to turn off your emotions as an investor. I'm not sure that's always right.

    There's even more to that. This idea that we should shut off our emotions, I think, is a mistake. In my judgement, it's not emotions per se that get us into trouble — it may be the human ego. The ego is this armour we build that tries to protect us against the uncertainties of life. It operates from fear, and when we make investment decisions from that place, we make terrible mistakes, because the ego distorts our perception. We have the capability to discern quality — the cheshm del — but the egoic perception muddies the mirror. It could come in the form of "I can't own that because it'll make it harder to raise money," or "I can't sell this losing position because it would be admitting to my clients that I made a mistake." Another way ego shows up is this illusion of control: the belief that if you build the perfect spreadsheet or make the hundredth customer call, you're getting closer to reality. We usually have to learn the hard way that reality seldom bends to the whims of our spreadsheet.

    By contrast, emotion can be incredibly beneficial to investors. When you discern whether the CEO sitting across from you is trustworthy, that's pre-intellectual. When you reflect on ownership of a business over a few years, how that feels can tell you a lot. When you find yourself becoming more and more impressed as time goes on, that is a signpost by itself — the normal experience is that mediocrity becomes more and more evident over time.

    PIMCO and the Limits of Intensity

    William Green

    You started out in a very different environment. You came out of UCLA and were hired at PIMCO — the world's biggest bond firm at the time, 2014 to 2016, co-founded by Bill Gross. People on the investment team would arrive at 4:30 a.m. and stay for 12 or 13 hours. What was it like as a 22-year-old entering that world?

    Nima Shayegh

    Rumi has a quote: all things are known through their opposites. In some ways, that experience clarified what I wanted to be doing long term. I was the youngest analyst on the team by some years. You would arrive at 4:45 or 5:00 a.m. in a suit and tie. It's usually dark when you arrive; it's usually dark when you leave. The culture expected you to have a cogent opinion on every little economic development, every piece of news related to one of your companies.

    I was lucky to have access that a 22-year-old almost never gets — flying around the country to meet with executive teams, access to any piece of research, former central bankers advising us on the economy, PhD computer scientists running correlations on different asset classes, hundreds of analysts covering specific securities. You would think we had every possible resource to compound capital at extremely high rates. And yet, six months in, I was reflecting on why people like Warren Buffett, Charlie Munger, and Lou Simpson were able to compound capital at 20-plus percent for decades, essentially as a person in a room, while we were sitting in very large offices working incredibly hard with great pedigrees — and compounding at basis points above the benchmark. I was missing something.

    William Green

    There's a lovely line from one of your shareholder letters: "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 McMuffins and bridge games, outperform the armies of well-paid analysts with six monitors each?" What did you conclude about why these incredibly smart, intense people with every resource aren't producing outrageous returns?

    Nima Shayegh

    I think a lot of it has to do with risk aversion, and that goes across the spectrum — not just the investment products being managed, but the institutional level. There is very little tolerance for volatility. No one wants to look wrong for any short period of time, even if it means long-term results will be much better. There's very little tolerance for discomfort of any kind. The bias and the incentive structure is to operate in a way that keeps assets. If that means slightly less performance over time, I think that is a trade-off the industry has made. For better, it allows people with a different orientation to have better results.

    Lou Simpson: A Different Way of Being

    William Green

    You moved to Naples, Florida, and worked with Lou Simpson at SQ Advisers from 2016 to 2019. Lou was head of investments at Geico for 31 years, from 1979 to 2010, and crushed the market by a huge margin over that period. Tell us about what it was like when you first met him.

    Nima Shayegh

    Every time I think of Lou, the memory that always comes is the first time we met. I was in my mid-twenties and working at a more or less traditional investment firm. The energy I carried was an over-analytical habit: formality, intensity. I arrived in Chicago carrying a very thick stack of research material — charts, valuations, everything. I imagined this intimidating investment legend would rigorously cross-examine every detail of my thesis. My heart was beating a little faster than usual.

    I expected to be met by an assistant or ushered into a waiting area. Instead, the elevator doors opened and there was Lou himself standing in the hallway — very unassuming, no formality, no pretension. He led me into an office that was the polar opposite of the office I had been in the day before: no Bloomberg terminals, no financial TV, more like the library of a scholar — a comfortable chair, a couple of piles of reading material. He looked at me and said, "Make yourself at home. Let me make you a coffee." That line stopped me in my tracks. Here was someone who had compounded capital at world-class rates for decades, praised many times by Warren Buffett, someone I had been studying since college — and he was stepping away to make coffee for a visibly nervous 20-something who hadn't done anything yet.

    When he returned, he didn't launch into a monologue or assert how smart he was. He asked questions with sincere curiosity — a remarkable receptiveness for someone with his experience and reputation. That first meeting left such a deep imprint. It opened a window: there was just a different way of being in this work. It didn't have to be this hard-charging, hyperactive way of operating.

    Lou carried remarkably little ego, which was so different from the archetype you typically encounter in the investment world — very bright, hardworking people who insist on puffing up their accomplishments. Some of his most extraordinary achievements would slip out accidentally after you'd known him for years. He was quick to say, "I don't know." When someone challenged one of his beliefs, he wouldn't get defensive — he'd say, "Maybe you're right. I should think about that more." I truly believe his lack of egoism was a big reason he was a great investor, because it gave him a clearer perception of reality.

    William Green

    The one conversation I had with Lou was on a Zoom breakfast with Charlie Munger. He had been buying Alibaba, and Lou said something like, "I just bought it yesterday, so it's bound to go down 50% immediately." Something so self-deprecating. And of course it did go down 50%.

    Nima Shayegh

    A friend of mine offered me a definition of humility I think is remarkably precise — perhaps the best that exists. He said humility is the awareness of your utter dependence on all that exists and your interdependence on everyone around you. The opposite is a self-centred perspective: the belief that we did it all alone, that we're the ones in control. That clouds your perception and distorts your judgement.

    When everyone else would pitch great ideas, Lou would say things like, "I think the portfolio is just okay. Maybe it's a little tired." This is one of the best investors of all time being ho-hum about his portfolio, whereas in the Monday morning meeting of many large investment firms, you would hear people pounding the table on probably mediocre ideas. His humility wasn't performative. It came from a real awareness of how little we actually control. Buffett's line about the ovarian lottery captures that spirit: we like to believe we are the sole cause of our own success, but so much of what goes right is really just the beneficence of life.

    There's a lovely line from Alan Benello's book on concentrated investing, quoting Lou: "We are 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." Lou lived a balanced life in the years I knew him. He would read broadly, had an amazing sense of humour, made it a priority to exercise — long walks or a swim in the mornings. On one occasion, the market was open and our portfolio was probably down quite a bit on the day, and he just called me and said, "There's this new exhibition at MoMA. Do you want to go?" We just spent the afternoon wandering around looking at art.

    What I know is that if you intend to have a long-term investment journey and have surrendered to the volatility, constantly sprinting and being reactive to every little data point will destroy your physical and mental health, strain your relationships, and ironically make the investment decisions worse over time. The harder you push, the shorter your runway. Compounding is all about the number of years. Creating space in your life is invaluable. It's not intuitive for most people to think that going for a walk may be better for your portfolio than adding another scenario to your Excel model.

    Surrendering to Uncertainty: History, Volatility, and the Long Game

    William Green

    You mentioned that studying investment history shows very long periods of underperformance for even the greatest investors — emotionally very uncomfortable periods. Can you talk about that?

    Nima Shayegh

    Studying investment history at any level makes it clear that over a multi-decade journey, there will be large periods of underperformance and large declines within those periods. Ben Graham's fund declined by 70% in the 1930s; he was still making distributions, so the starting capital was down perhaps 80%. John Maynard Keynes's personal portfolio declined by 80% in the 1930s, and the portfolio he managed at Cambridge declined by about half. In the 1970s, Charlie Munger had 80% of his capital in two stocks — Blue Chip Stamps and the New America Fund — and his portfolio declined by more than half in two years, wiping out the prior seven years of returns cumulatively. Shelby Davis's personal portfolio declined by 60% in the 1970s due to margin debt. In the late 1990s, Lou Simpson himself was 50 or 60 points behind the S&P 500, and that little stretch wiped out nearly a decade of outperformance. Berkshire Hathaway itself has declined by 50% multiple times.

    These periods of extreme volatility and underperformance are just very normal. The question becomes: given that reality, how should you structure your environment for that inevitability? When you have a truly long-term orientation, you start to surrender in some ways. You simply stop engaging with certain kinds of questions — will there be a recession next year? Is AI a bubble? Is the US fiscal situation unsustainable? These are interesting questions, but over a long time horizon they don't matter that much, and ruminating on them has been an expensive distraction for many people over many years.

    There's a story about Lou in 1987 that was instructive. He thought stocks were very overvalued and took his portfolio to 50% cash early in the year. When he reflects on that period, he sold stocks at the highs but paid his taxes. Then the market crashed, snapped back so quickly that he didn't deploy his capital fast enough — he made the right decision at the highs but not at the bottom. In his estimation, he may have added some value net of all that, but it may have just been better to remain fully invested and roll with the punches.

    William Green

    There are a couple of lines I really like from your shareholder letters. One said, "One of the enduring amusements of this profession is how reliably investors are shaken by what is in fact a recurring pattern." And you asked, "What if we simply chose not to partake in the theatrics?" And: "We are focused on owning individual businesses whose long-term reinvestment dynamics are resilient to changes in macroeconomic conditions." Can you comment on that?

    Nima Shayegh

    I think this work is almost unnervingly simple. At the end of the day, it's about trying to understand the economic reality of a business — Lou used to say it's about understanding the future economics. To the extent that the macroeconomy is going to have a huge impact on the future economics of a business, it may not be a great business. The idea is to own specific businesses that are resilient despite the inevitable turbulence that life presents. It really simplifies life to opt out of things that are outside our control.

    Founding Rumi Capital: Structure, Alignment, and the Right Ecosystem

    William Green

    When Lou eventually closed SQ Advisers and retired, you founded Rumi Capital Partners in October 2019. Do you remember his advice to you as you launched?

    Nima Shayegh

    His main advice was to focus on producing results rather than doing the things you're told you should be doing — getting a fancy office, putting together a pitch deck, running around raising money. I am so grateful for that advice. The first couple of years gave me so much space that benefited both the process and the relationships with the people who invested from day one. I started Rumi not long before COVID and not long before another decline in 2022, and the experience of those periods was serene. Not that it's always comfortable to watch account balances decline, but it was as easy as you might expect, because you felt alignment across the ecosystem.

    William Green

    That word "alignment" seems very central to you. Your founding principles talk about a culture rooted in alignment. You invest in businesses whose leaders are driven by a core sense of alignment. You have a fee structure with a small management fee that shrinks as assets grow, and an incentive allocation only after a 5% cumulative hurdle. You've written, "I am wholly uninterested in being rewarded for simply existing." How does alignment show up in the companies you invest in?

    Nima Shayegh

    Alignment is another root quality that can't be quantified. In the investment world, we try to set up rules to force alignment — what percentage of the company does the CEO own? But for certain kinds of people, the output doesn't matter so much. If Warren Buffett owned a little less Berkshire, I don't think his behaviour would change. Alignment is something you have to embody first, and then the output is just the output.

    In the case of Rumi, I wanted to emphasise that this is a performance-oriented partnership — not about raising capital, not about having a good couple of years, but about compounding capital for multiple decades. And that means finding businesses where the managers have a similar orientation. If Bruce Flatt at Brookfield is thinking about the next 20 years, and 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 a good outcome are dramatically improved.

    William Green

    Brookfield and Appfolio have been two of your biggest positions since inception. How do they embody what you're looking for in terms of long-duration reinvestment runways?

    Nima Shayegh

    Charlie said it best: the longer you hold something, the closer you will get to the intrinsic reinvestment return of the business. If you intend to own something for a very long time, it's imperative that the business is generating high returns — not on a reported basis necessarily, but an ability to reinvest at high returns. I'm looking for businesses that have this intrinsic ability to compound capital over time. That excludes all kinds of things: I tend not to buy things just because they look statistically cheap, or ideas that will be okay for the next few years but face existential threats thereafter. I won't buy a melting ice cube regardless of valuation.

    Appfolio is a good example of long-duration reinvestment. It sells software to real estate property managers — ultimately a significant reduction of entropy in the real estate industry. It saves property managers time, reduces labour, makes their lives easier. Because it sits in the middle of all these workflows and employees are trained on the product, it creates incredible stickiness. When customers stay for 10, 20 years, many software companies take advantage of that stickiness by cutting costs, stopping innovation, or jacking up prices. Appfolio's ethos is a partnership approach — by far the most customer-oriented culture in the market. As they add features, they can charge a small sliver of the value created. As you grow in vertical software, you gain referenceability: when someone's making a purchase decision, they call a friend in the industry who says, "I use Appfolio." The product becomes the standard increasingly, and as long as you're treating customers well, you have those relationships for a long time.

    William Green

    They're very customer-focused and not Wall Street-focused. They wouldn't webcast their investor days or have transcripts. Their earnings calls had no Q&A. Can you talk about that?

    Nima Shayegh

    I may just be drawn to it because when someone is doing something special, they don't always have to broadcast it to Wall Street. Appfolio fits that bill — an extremely non-promotional culture, no long-term financial guidance, which frustrates sell-side analysts who basically want the company to do their work for them. You can listen to one of their calls and it's 10 minutes of prepared remarks, then they say, "All right, thank you very much, see you next quarter." For that reason, the stock has been largely misunderstood by the market for years. At one point more than 50% of the company was held by insiders; that illiquidity and lack of promotionality creates volatility. Over 10 years the company has compounded at more than 30% a year, but more than half of all trading days over those 10 years were spent in a drawdown of more than 20%. That makes it genuinely difficult to own.

    Holding Through the Long Stretches

    William Green

    Can you talk about the challenge of holding exceptional businesses through these difficult periods? Ben Graham owned Geico from 1948, Phil Fisher owned Motorola from 1955, Buffett bought the Washington Post in 1973, Tom Russo bought Nestlé in 1986, Lou Simpson bought Nike in 1993, Charlie Munger bought Costco in 1997, Chuck Akre invested in American Tower in 2002. What enabled them to hold through the long stretches where nothing happens?

    Nima Shayegh

    I spend a lot of free time reverse-engineering the great investments of the great investors — not just those periods where things are going great, but those long stretches where nothing happens and you start to see everything else going up. So much of holding a business for a long period is being able to see what you have clearly. Rumi has a quote: to look at the thorn but still see the rose — to have a balanced understanding of what you own and not be swayed by long periods of underperformance.

    Costco is quite striking. Charlie bought it in the early 1990s and held it until his death — decades. Over that period, the stock compounded in the high teens for multiple decades, a wonderful outcome. But between 2000 and 2010, the stock barely moved. In the late 1990s they had been very ambitious — they thought they could grow new stores at 10 to 15% a year with high-single-digit same-store sales growth. In the early 2000s, they overshot on their ambition, had to rein in store growth, and same-store sales were getting impacted by competition from Sam's Club and Walmart. The stock declined from perhaps 50 times earnings in the late 1990s down to 12 times earnings around 2003 or 2004.

    I once asked Charlie what he saw that allowed him to own something like this for so long. The first thing he did was remind me: in markets where Sam's Club was opening stores across the street, Costco was actually cutting its prices. The sharp Wall Street analyst doing channel checks would find this business has no pricing power — so what kind of good business is Costco? But those were all temporary dynamics. Charlie's answer was that the product quality was improving, the management was ethical, the culture was meritocratic. These are root qualities that would never have shown up in any spreadsheet or fancy research report. The root qualities allowed him to own the stock for multiple decades and never get shaken out.

    William Green

    You wrote something really nice in one of your shareholder letters: "This may be precisely why attractive long-term returns are available to those with a different temperament, orientation, and structure." There's an intellectual understanding of why you want to be patient, but there's also an element of temperament — Charlie's ability to defer gratification — and then there's structure: you have to have structured your investment firm so your shareholders allow you to be long-term.

    Nima Shayegh

    Many of these investment questions are what E.F. Schumacher called divergent problems. A convergent problem — how should we create a two-wheeled human-powered means of transportation? — increasingly converges on a single answer: the bicycle. Divergent problems don't converge. The classic example is how should we educate our children? One group says give children immense freedom to explore. Another says you need rigorous discipline and following rules. At the extremes, the answers are polar opposites. Aristotle said it well: every virtue is in the middle of two vices.

    So much of investing sits at this point. Urgency versus patience, working hard versus letting go, trust versus scepticism, concentration versus diversification, generalist versus specialist. You learn that you need both, in some harmonious proportion that only intuition can tell you. With building an investment firm, of course you need some capital to start — but if you spend all your time on that, your investment performance will suffer. You need a network, but you also need independence. All classic divergent problems.

    Carvana, Conviction, and the Paradox of Networks

    William Green

    You and I have talked a lot about the tension between having a circle of thoughtful friends to discuss ideas with and thinking for yourself. Carvana is a really interesting example — you have these exceptional long-term businesses, but sometimes you'll buy something with tremendous asymmetric upside that's pretty hairy. The stock fell about 93% before you bought it, and a lot of people thought it was going bankrupt. What did you see in it?

    Nima Shayegh

    Having a small circle of friends in this work is incredibly valuable. It gives you access to thoughtful perspectives, creates healthy intellectual tension, sharpens your thinking. But like almost everything in investing, there's a paradox to manage: if you rely too heavily on a network, you risk groupthink and outsourcing your judgement, robbing you of the conviction you need when markets become volatile. Templeton said the best performance is produced by a person, not a committee. On the other hand, if you isolate yourself completely, you risk falling in love with your own ideas. So I try to live in the middle way — open and receptive, but trusting my own judgement.

    My preference is always for a large holding in something where the risk of impairment is deemed remote. But every once in a while, you find something with potentially the same impact as a large successful position, even when the starting position size is relatively small — highly asymmetric. I will occasionally own something like that.

    The Carvana story really began when I was working with Lou, because we were shareholders of CarMax — I think at one point we owned around 5% of CarMax equity. I remember walking down Michigan Avenue in Chicago, listening to the Carvana road show, and being struck by the thoughtfulness and ambition of that management team. My own investment palette at the time wasn't geared towards companies growing hundreds of percent and burning so much capital, so I watched from the sidelines. Over the next few years they executed flawlessly: extended into new markets, turned inventory faster, increased delivery speeds, improved profitability in specific cohorts, created vertically integrated first-party logistics. A colleague of mine, Armen, built an early web-scraping tool that compared apples-to-apples cars on Carvana versus CarMax and found Carvana was underpricing the industry by around $1,000 per unit — significant in a market with $2,300 gross margins per unit for CarMax. The stock promptly rose 20 times.

    Then in 2022, a combination of bad luck and misexecution brought the business to a sudden halt. They had taken on a lot of debt for a big acquisition. The bonds got down to 30 cents; the stock declined by about 93%. By the time I bought our first shares, the stock had fallen from $370 to $25. The short interest was 75% of the free float — essentially everyone thought it was going bankrupt. My timing was not great; I bought at $25 and just a few months later it had gone to $3.50, down another 85% or so.

    During this period I was definitely not talking it up. I would bring it up just to discuss it, to hear different perspectives, but I didn't want to say I liked it or owned it, because at certain points the stock would be up or down 70% in a day on some headline. What I wanted to prevent was a lot of inbound inquiries, because responding and defending would create commitment bias. The moral of the story is that stocks can do anything in the short term. Literally anything. Spending a lot of time trying to predict if or when they might go down by a lot has been a challenging and usually unproductive exercise.

    The Psychology of Concentration, Surrender, and the Mirror

    William Green

    How do you handle the emotional and psychological side of being a very concentrated investor? You own about nine stocks with perhaps 90% in six or seven of them. Your returns since inception have been excellent, but in 2022 you were down about 42%, then up about 70%. You meditate. I'm curious what you've done practically to deal with the emotional intensity.

    Nima Shayegh

    Maybe it's two things. The first is studying history — recognising that these periods are normal. When they come, you shouldn't be surprised. Every investor gets their time over a 30-, 40-, or 50-year record, and so when 2022 came I was mentally preparing for it to last five or ten years. Constantly reminding yourself of that helps. It's also easy to become complacent when capital accounts are just rising month after month, and I think those moments where things are going really well are an opportunity for humility. When moments are going poorly, it's an opportunity for trust — to recognise that this is normal and to trust the process.

    In practice, I try to find some harmony between different aspects of life — work, family, health, inner life. That may mean exercising, making space for meditation. My family has no interest in business, which is a blessing in some ways: spending time with people you love who have absolutely no idea what the stock market is doing can be great. Those things sound trite, but they really do restore perspective and proportion to the whole process.

    William Green

    There's a lovely section in one of your shareholder letters about the willingness to surrender in the face of uncertainty. 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 part of what surrender means for you is staying fully invested and not trading around core positions. Does that resonate with anything for you?

    Nima Shayegh

    Surrender goes hand in hand with trust. The reason we can intellectually accept that it's normal to go down 50% and yet not want it to happen is that in some ways we don't trust that we'll do the right thing when it happens. There's a lack of trust in the self. The experience in 2022 was illuminating because in 2020 and 2021, everyone was a long-term investor — month after month, just getting richer and richer. Then in 2022, you could see the time horizon shrink. Suddenly everyone wants to learn a lesson; everyone is saying "What was I thinking?" In some cases those were genuine reckonings, but in other cases it was merely a reaction to price action.

    Ironically, had we not had 2022, our returns since inception would actually be worse. The opportunity a down market gives you is the ability to coil the spring. You can recycle capital — sell things that are down 30 or 40% to buy things that are down 70, 80, or 90%. That actually benefits you over the long run. That is why Buffett and Lou Simpson and so many others over history have tried to make this point: volatility is the friend of the investor. The hangup is that even if we know that, do we trust our ability to make the right decision when that moment comes? If you trust that when you're down 50% you'll know what to do, then what is there to fear? You can just let it come.

    William Green

    You talked about sell decisions being love versus fear. Can you explain that framing?

    Nima Shayegh

    Someone asked me recently how I sell, and what emerged was this love-versus-fear distinction. Suboptimal sell decisions are fear-based: I had a 10% position and now it's 12%, that's too big — what if it goes down? I'll pare it back to 10. That kind of thinking happens all the time in the name of risk mitigation or rebalancing. If you do that, you never get the full benefit of a great investment.

    A love decision is where you feel compelled — called to own more of this business. Because you run fully invested, you have to get the capital from somewhere. It's a positive decision rather than a negative one. Sell decisions come in a few flavours: you can sell because you made a mistake, for opportunity-cost reasons where you prefer one business over another, or when something is egregiously overvalued such that you might have negative returns for a very long time. I'm not sure that last scenario has happened in my experience over these first six years. Realistically, 80-plus percent of the time it's an opportunity-cost calculation.

    Rumi, the Polished Mirror, and the Essence of Investing

    William Green

    I was struck that surfing comes up a couple of times in your shareholder letters. There's a quote from meditation teacher Jon Kabat-Zinn: "You can't stop the waves, but you can learn to surf." And one from William Finnegan's Barbarian Days: "Surfing always had this horizon, this fear line that made it different from other things... The waves were the playing field. They were the object of your deepest desire. At the same time, they were your adversary." What's the parallel between investing and surfing?

    Nima Shayegh

    Surfing really demands surrender — this idea that you're not going to predict what's going to happen, but you have to be open and receptive. I had one experience down in Costa Rica with Chris Beg. I was out there waiting for a wave, I saw one coming, and being not a great surfer, I was looking left and right, hoping someone would tell me: this is the right wave. Everyone was focused on their own thing, playing their own game. I waited for validation, then just decided this was a great wave and took it — and it was a lovely ride. It reinforced the idea that no one is coming to save you, particularly in investing. The idea of investor idol worship: it's easy to think that by following someone else's path, by investing the way someone else invests, you'll find the right path. But ultimately it comes down to you. You have to make your own decisions, trust your own judgement, develop your own discernment. There's no substitute.

    William Green

    Naming a firm after a 13th-century Sufi mystic in 2019 was an unusual decision. How has Rumi been important to you both as an investor and in life?

    Nima Shayegh

    One thing I always find fascinating about Rumi is that in the late 1990s and early 2000s, he was actually the bestselling poet in the United States — more copies than Shakespeare, Homer, Dante, Milton. What are all these Americans doing reading the poetry of a Persian mystic from 800 years ago? I think it's because Rumi's ideas are universal. He speaks to something timeless in the human condition — this deep yearning to see beyond the surface and discover meaning beneath appearance. His constant provocation is to see past appearances and ask what is actually real, what is the truth.

    What makes him timeless is his ability to embed deep truths about existence into the most ordinary everyday imagery — a garden, the sun, a candle, a moth. He points you from the obvious and the visible towards the invisible and the essential. That way of seeing has always resonated with me as an investor, because investing at its core is an act of perception. It's about seeing beyond the narratives — what the news is talking about, what other investors are talking about — to try to grasp the essence of the business.

    William Green

    Is there a favourite line of his that you live by?

    Nima Shayegh

    There's one quote that is one of my favourites: "If you are irritated by every rub, how will your mirror be polished?" On one hand, he's saying that if you take everything personally, you're missing the lessons of these moments. But what he's actually talking about is the way our egos distort our ability to see clearly.

    In the ancient world, mirrors were not made of glass. They were made of bronze — a craftsman would combine copper and tin, then polish the surface until it became reflective. If the metal was left uneven or corroded, when light came into the mirror it would scatter in every direction. You couldn't see clearly. That metaphor about human beings as mirrors is so precise: we start as base metal, not reflective, not beautiful. With polishing, we can reflect reality. The unevenness and corrosion of an unpolished mirror is akin to the distortions caused by our egoic perspectives — when we need to appear superior, when we fear being wrong publicly, when we fear humiliation, our perception of reality becomes warped and we stop seeing things as they truly are. When we make decisions from that place of fear and ego, of course we make terrible decisions. That's my Rumi quote.

    William Green

    One of the reasons I love talking to you is I have this sense that investing is like a beautiful subset of worldly wisdom — it includes everything. You study human nature, psychology, philosophy, spirituality. Last time we talked, you quoted a conversation with the author of a book by Vaclav Smil. You told him you were an investor and he said, "Ah, so you're a money massager." I think this conversation proves you are much more than that.

    Nima Shayegh

    He said, "So what is it that you do again?" I said I'm an investor. He said, "Ah, so you're a money massager." The perception of the business is that we're sitting around massaging this portfolio of securities. It's not a real profession. But I don't feel like it actually is — it's a beautiful means of exploring your curiosity and hopefully serving people while you do it.

    William Green

    On that note, it's been a real delight. I hope I'll see you soon — in Omaha, at the very least.

    Nima Shayegh

    Absolutely. It was a pleasure. Thank you.