September 2026 Random Ramblings
Andrew Walker’s central market call is that equities have not ignored higher rates, but still do not look fully adapted to them. The 10-year yield moved from 4.2% at the beginning of the year to 4.6% at August-end and 5.1% by September 24, while the S&P 500 remained near record highs. Refinancing lags and slow portfolio reallocation could delay the impact, but “the financial burden is coming your way.”
The refinancing calendar may matter more than today’s apparently healthy free cash flow. Companies termed out debt during 2015-22, insulating earnings when rates first rose; debt issued around 2021-23 may roll between 2028 and 2031. A company refinancing 3.5% debt at 8-10% could discover that today’s cash generation materially overstates its future economics.
Higher rates have reset the arithmetic of special situations, even when investors’ instincts have not caught up. A guaranteed $100 merger consideration received in one year is worth roughly $95 at a 5% interest rate—and less after allowing for break and liquidity risk. Investors trained when “capital is free, time value is low” may mistakenly see a stock at $94 as an unusually wide spread.
The disappearance of prolonged bear markets could reflect stronger safeguards—or a system accumulating hidden fragility. Circuit breakers, rapid Federal Reserve support, and less cyclical business models may explain why the global financial crisis, COVID correction, and 2025 tariff scare reversed relatively quickly. Walker nevertheless wonders whether repeated rescue creates a market that can open down 5% and, after “wire after wire goes off,” be down roughly 20% by lunch.
Great investment records may disproportionately belong to overconfident survivors rather than proving overconfidence is optimal. Concentration and leverage give the overconfident investor the variance required to reach the top, while failed counterparts disappear from view; Archegos is the stark specimen of accumulated success ending near zero. Confidence also attracts LP capital, further strengthening the selection effect.
Outgrowing a mentor is a natural consequence of accumulating judgment, not necessarily a repudiation of the mentor. Ian Cassell’s account of separating from Skip leads Walker to Buffett moving beyond Ben Graham and to the warning that certainty can initially look like wisdom: some mentors are “often wrong, never doubting.” Walker’s practical response is to journal market and portfolio views so he can compare what he thinks now with what he actually thought years earlier.
1. Rising rates are exerting gravity with a long fuse
Walker’s starting dislocation: the 10-year yield rose from 4.2% at the beginning of the year to 4.6% at August-end and 5.1% by September 24, yet the S&P 500 remained around all-time highs and the major indexes were up roughly 12-13%. “Interest rates are financial gravity,” but the apple has not visibly fallen.
His historical comparison comes from valuation work around 2011, when long rates were near 2%. Companies could borrow around 4% while equities appeared to yield roughly 10%, suggesting an excessive equity-risk premium; the subsequent decade brought strong earnings but also substantial multiple expansion as markets adjusted to cheap capital.
One possible lag is behavioral: savers do not instantly redirect marginal dollars merely because bond yields become more attractive. Walker concedes that large asset managers, rather than households, control much of the money, so consumer inertia may be an incomplete explanation; the point is a hypothesis, not a market-timing claim.
The more concrete lag sits in corporate liabilities. Companies extended maturities during 2015-22, but debt issued around 2021-23 may refinance during 2028-31; replacing 3.5% coupons with 8-10% debt would reduce future free cash flow and alter capital allocation. The market should discount that immediately, yet Walker wonders whether it “slowly adapt[s] to gravity.”
2. Elevated indexes conceal widening stress underneath
The surface remains healthy—economic growth and profits are good—but Walker sees a narrowing margin of safety as prices stay elevated and rates rise. His deliberately hedged conclusion is not that a crash is imminent; it is that “there’s a lot of volatility on the horizon” and the financial burden has yet to arrive fully.
Stress is already visible in rate-sensitive pockets: leveraged small caps, the Russell 2000, and housing have struggled, while biotechnology first fell sharply and then recovered strongly. The dispersion matters because “when markets are at all-time highs, there’s always a crash somewhere.”
Housing is his clearest specimen. Smart investors have begun revisiting builders, and Berkshire’s purchase of 200 million Lennar shares caught his attention with the company trading around tangible book value. He treats that position as small for Berkshire and not dispositive, but notes that depressed housing names possess several potential operating and valuation levers.
3. Special situations now demand an explicit cost of time
Walker’s merger-arbitrage arithmetic is blunt: if a transaction pays $100 in one year and rates are 5%, a literally guaranteed claim should trade around $95 today. Because no deal is guaranteed, the correct price must sit lower still to compensate for closing probability, corporate liquidity, and the downside if the transaction breaks.
That makes a supposedly obvious $94 opportunity much less obvious. After discounting the $100 consideration and incorporating break risk through position sizing and Kelly-style upside/downside analysis, the quoted price may already imply roughly a 90-95% probability of completion rather than an extraordinary return.
The contrast with 2015 is formative: when rates were near 2%, a very safe $100 deal might trade at $98 or $99 because “there wasn’t much money measuring time.” Generalists who came of age during 2010-20 may still carry the embedded assumption that “capital is free, time value is low”; Walker says pod shops are generally better at estimating cost of capital, making this more a generalist-versus-specialist event-investor issue.
Walker connects regime conditioning to Buffett launching his partnership despite warnings from his father and Ben Graham that the Dow had never been higher. Their caution reflected the market that shaped them; Buffett believed profits and circumstances had changed. The broader lesson is that inherited assumptions can remain invisible long after the underlying regime turns.
4. Shorter bear markets may be producing a more brittle system
Walker contrasts modern reversals with Black Monday, 1929, the Great Depression, and the brutal 1972-74 decline. His emblem of 1974 is Buffett’s line about feeling like “an oversexed man in a harem,” swapping stocks at five times earnings for alternatives at four times because bargains were everywhere.
Even 2000-02 was not uniformly bearish: expensive dot-com stocks collapsed while many value names performed well, helping create reputations that endured for decades. For the global financial crisis, Walker says the market peaked in October 2027 and describes the episode as running from July 2000 to March 2009—“about 9 months”—an internally inconsistent dating he does not resolve. COVID’s fall lasted about two months, and the 2025 tariff panic less than one.
Possible explanations include circuit breakers, expected Fed liquidity, fiscal support, and a corporate mix less dominated by deeply cyclical steel and automobile businesses. Walker offers no firm answer: “Maybe we just live in a wonderful world, we’ve been lucky,” or perhaps falling rates from the early 1980s through 2022 continually supported valuations.
The antifragility counterpoint is the uncomfortable one. Repeated intervention may suppress small failures while making the system increasingly brittle; zero-day options and other market-structure features could amplify the eventual break. Walker disclaims expertise but imagines an opening down 5% cascading toward 20% by lunchtime—and wonders whether rising rates now make sustained bear markets more plausible.
5. Confidence creates legends, casualties, and eventually distance from mentors
A friend’s taxonomy divides investors into the overconfident and those with imposter syndrome. Walker places himself in the latter camp: even after doing the work, he must remember, “You are an expert,” because “there’s no secret expert who knows everything” waiting to reveal the real answer.
Yet the great investors he can readily name appear highly confident, sometimes overconfident. Reading about Buffett in his twenties and thirties complicates the humble-Omaha image; episodes involving GEICO and Salmon Brothers also remind Walker how often precarious situations turned favorably. Alternative outcomes could have produced very different legends.
Survivorship bias supplies his leading explanation. The overconfident investor embraces concentration, leverage, or both, generating the variance needed for spectacular success—and spectacular disappearance. Bill Hwang’s concentrated, increasingly leveraged Archegos bets are the clear example: success compounded until it effectively collapsed overnight. The same confidence can also attract the LP capital required to become prominent.
Ian Cassell’s Stock Picking gives the mentorship version. Cassell learned from Skip, then developed beyond Skip’s fixed style; similarly, Buffett moved beyond Graham. Walker says Graham apparently gave a speech sometime in the 1970s, shortly before he died, favoring simple market-wide rules that, if the account is right, resemble early factor investing. Mentors initially possess “oceans and oceans of knowledge,” but a 20-to-zero experience advantage becomes 20-to-five, their fallibility becomes visible, and “often wrong, never doubting” stops looking like wisdom.
Walker’s unresolved question is whether mentees advance because mentors stop evolving, because students evolve faster, or because previously hidden risk finally surfaces. His practical safeguard is written memory: use the blog and a journal to record market and portfolio thinking, then use ChatGPT to compare today’s beliefs with the views he actually held years ago.
Full transcript
You are about to listen to the end of a value podcast with your host, me, Andrew Walker. Today is my monthly random chatter. Before I get into it, if you watch the video, you'll see me holding the wire. Why am I holding the wire? Because this is the wire to my microphone, and I forgot to connect it before starting the recording. My laptop intercepted the microphone instead of using my actual audio, so the audio quality will probably be pretty bad. I'll try to fix it during the editing, but I wanted to warn you.
Speaking of disclaimers, there is no investment advice on this podcast. That's always true, but it's especially true today because I'm just winging it, and I'm a person who can't remember to plug in his microphone. I'm going to chat for 30 minutes about a bunch of things that have been on my mind, so we'll get to that in a second.
What am I talking about today? I'll start by talking about the market in general. Interest rates have been rising sharply for most of the past year, especially in the last few weeks, so I'll share some thoughts on interest rates, financial gravity, and why we don't really see gravity starting to pull things down.
Then we'll move on to a brief discussion of how crashes and bear markets seem to have disappeared over the last 25 or even 40 years. Where did they go? Why did they disappear? Are markets more fragile today because of this? Maybe I'm not going to discover anything new, but these are just some things that have been on my mind.
I'll also have a brief discussion of interest rates in special situations. I think a lot of investors who grew up in the 2010s were trained in one direction, and they may not have adapted to the interest-rate environment we're in today.
Then I'll discuss overconfident investors versus impostor investors. I'll explain that when we get there. Finally, I'll discuss mentoring, largely driven by Ian Cassell's book Stock Picking. There was some discussion about mentors, and it keeps going through my head. I love this book, and I've been thinking about it, so I wanted to write these thoughts down on paper.
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2. Two stories: Muse and rates
Let's dive in and start by talking about markets. I think it's around noon on September 24 when I'm recording this. Over the last couple of weeks, there have been 2 stories that have generally dominated the markets.
The first is generative AI, specifically Muse, which is topping the charts and all that stuff. That's causing a lot of sell-offs because of consumer inertia and so on. I've blogged about it 3 times in the last week, so you know what? I know we live in a world where audio is changing rapidly, but you can just go read those posts, especially the article I published this morning about consumers, consumer inertia, selling out, and the differences between them.
3. Interest rates are financial gravity
The other dominant story in the markets right now, and what I'm going to discuss in this podcast, is interest rates. I don't want to say interest rates are outrageously high—we live in a hyperinflationary world or something—but they have been going up rapidly.
If you look at 10-year bonds, at the beginning of the year they were at 4.2%. At the end of August, they were at 4.6%, and now they're at 5.1%. They've risen rapidly in the last 3 weeks. That's another big story because interest rates are financial gravity.
I think Warren Buffett said that interest rates are to asset prices what gravity is to an apple. I think it was Warren Buffett, although you can correct me if I'm wrong. Interest rates serve as financial gravity.
I've written before about how, around 2011, when we were in the ZIRP era, long-term interest rates were around 2%. If you ran a DCF—and I worked at a valuation consulting firm—you looked at the stock price in the DCF and said, “Either there are huge questions about terminal value here, we're completely wrong in all our modeling, or the stock prices are wrong.”
These companies were borrowing at 4% and their stocks were yielding 10%, so you thought, “That's too much of a risk premium on stocks.” Or I guess you could say the equity risk premium had been destroyed.
What happened then is that over the next 10 years, stocks had a great run. Earnings were growing pretty well to a large extent, but there was also a lot of multiple expansion.
Right now, the S&P 500 is hitting all-time highs. The Russell and the S&P 500 are up 12% to 13%. The Russell has been a little weak over the last month, partly because of these interest rates. A lot of things in the S&P 500 and the Russell are more sensitive to interest rates, but the economy is doing well, stocks are pretty high, and interest rates just keep going up.
I wonder if interest rates are gravity, as Warren Buffett says, but in the same way that if you throw something really high in the air, it keeps going up and up and up, then it slows down, and eventually it falls. I'm not talking about a sharp drop, but I wonder if interest rates work with a little bit of a lag when it comes to the stock market and this long-term perspective.
I can imagine a few ways that could happen. It could take a little bit of time, just as it takes people time to think about things. Consumers aren't perfect. It's a kind of consumer-inertia trade: they don't look at things right away and say, “The S&P 500 dividend yield is 4%, bond yields are 3%, and I need to move more of my money into stocks.” It takes time for that shift to happen.
I wonder if, when yields go up, it also takes time for people to look around and say, “My extra money is going into bonds, not stocks.” I wonder if this is a long-term thing. I don't know, because it describes a lot of what consumers do, and most of the money is managed by really big asset managers. So maybe that's too much. This is my monthly time for random conversations; I'm just thinking about it.
4. Does gravity work on a lag? The coming debt refi wave
Another way this could work over the long term is that corporations were very good from 2015 to 2022. They really turned their debt into long-term debt. The banks weren't as good; that's what happened with Silicon Valley Bank, First Republic, and everything else. They had a lot of floating-rate exposure, and they blew up.
Most corporations actually increased their debt and moved from long-term to medium-term fixed rates. So when rates started changing, it didn't affect them.
But what happens when most corporate debt is on a 5- to 10-year horizon? What happens when all this debt issued from, say, 2021 to 2023 starts to mature from, say, 2028 to 2031? If they're paying 3.5% on this debt now, they roll it over, and interest rates have suddenly gone up to 8% or 10%.
I wonder if that's one of the reasons why the lag effects are kicking in. The free cash flow they're generating now is being amplified by this interest-rate differential. The market has to be very efficient; it must take this into account. All I'm talking about is the market slowly adapting to gravity.
It has to adapt immediately. When interest rates go up, it has to say, “Hey, interest rates went up from 4.9% to 5%. Well, every business costs—I don’t know how much it would be—then 3% less.” I wonder if it works more slowly. Likewise, I wonder if it includes something like, “Hey, the free cash flow that the company is generating today is actually going to be lower in 2 years because they’re going to refinance at a much higher interest rate.”
I wonder if it will take some time for that to happen. There’s also capital allocation; managers are valuable, too. I wonder if this is some kind of refinancing wave that’s happening.
5. Index highs, pain underneath: housing, small caps, biotech
With that in mind, I said stocks are still touching or close to all-time highs. Last month was pretty tough for biotech, for example, and for the Russell 2000. You can see that there’s always a pattern: when markets are at all-time highs, there’s always a crash somewhere.
Earlier this year, it was SaaS. Now, small-cap leveraged companies have really been hit, and the housing sector has really suffered. I have a lot of smart friends who tell me, “Look at the names of real estate companies.”
It just happened to me at my desk a few days ago. Berkshire bought 200 million shares in Lennar—maybe 3 days ago or something. Lennar, a large developer, is trading just above tangible book value, right at book value.
So, Berkshire sees problems in the housing sector. They’re huge, and $200 million is nothing to them. They have a lot of money to invest, but a lot of smart investors are saying, “Hey, a lot of housing companies are starting to look testy, and there are a lot of different levers that can help these companies.”
The housing sector and small-cap leveraged companies have a lot of challenges. Biotech has come back really strong, and if you’ve been following me for the last 18 months, you know I follow biotech a lot. Biotechnology fell very, very quickly. I think there were some serious problems with gross revenues and all sorts of other things, but even when it’s at a historically high level, there’s a lot of pain underneath it.
Consumer and energy names—there’s still some value in them. Well, it’s hard for me to say there’s still some value in the assets. I think there are possibilities if you think they won’t be appreciated.
My bottom line here would probably be this: I don’t think stocks are ignoring rates, but it doesn’t look like they’ve really adapted to current rates. Growth is good now. I think there’s a lot of volatility on the horizon, and I would say that overall, the margin of safety in stocks is getting narrower and narrower as prices remain elevated.
I see a lot of risks looming for stocks, and interest rates continue to rise. Even though the profits are still good, I think the financial burden is coming your way.
6. Rates and special situations: merger arb isn't free money anymore
Another quick note about interest rates. I’ve written about this before, but interest rates have an interesting effect on special situations. If you announce a merger and it’s guaranteed to happen, but you say, “Hey, it’s going to take a year to complete the deal,” and interest rates are 5%, then if the merger price is 100, you’re trading for about 95.
That’s assuming there’s a guarantee that it will happen. Nothing is ever guaranteed, so you’ll trade just below 95 to account for the fact that there’s only a 99% chance it will happen. And, by the way, why should we think that Company A would buy Company Y as if it were the U.S. government?
There will be some corporate liquidity risk, and all these discounts are right, but it will happen at 5%. I think it’s interesting. The environment you grow up in often influences the way we think about things.
I still see people announcing a deal. In 2015, when interest rates were at 2%, the deal would be announced and the stock would trade at 98 or 99 if the deal was at 100. Basically, it would trade all the way up to that deal, especially if it was a really safe deal, because interest rates were effectively zero. There wasn’t much money in measuring time.
I’m being approached today, especially by station wagons. I think they’re the generalists; a lot of them come to me. The deal is done for 100, and they’ll say, “Oh, the stock is trading at 94. Isn’t this an opportunity?”
I’ll say, “I don’t think that’s a possibility. There is a risk of the deal breaking, so you have to factor that into your Kelly criterion, your upside and downside potential, and all that.” Then you just have to discount that 100 back to the present. Once you do that, it looks like this deal is trading at 90% to 95% implied.
Again, I think it’s more of a generalist than a specialist event-investor issue. I think pod shops are pretty good at estimating the cost of capital because they’re shrinking, but it’s just ridiculous.
You come of age in 2015, and there are assumptions. The assumptions you make determine how you invest. If you came of age in the 2010–2020 regime, the assumption was, “Hey, capital is free and the time value is low.” That assumption changes when interest rates rise. It’s interesting to think about.
I think about mentors, and we’ll talk about them later, but when Warren Buffett launched his partnership, the 2 most important people in his life—his father and Ben Graham—both said, “Hey, this is probably not the best time. The Dow Jones has never exceeded that number.”
Buffett launched it anyway. First, who cares what the market does? He’s Warren Buffett. He’s going to win. Second, he thinks they live in a different world. It had been 20 years, profits had increased, and all that.
7. Where did the crashes and long bear markets go?
That’s an assumption they made and developed in the market, based on what they did, and interest rates are similar. Those are my 2 things. Let’s move on to something else I want to talk about—market-related stuff.
I was just thinking: crashes and long bear markets—where did they go? You read history and see these days of big crashes. You think of Black Monday, when the markets dropped about 25% in 1 day. You think of the crash of 1929 that led to the Great Depression, when, again, stocks were down about 33% or something in a day.
Those were such big crashes. When you read history books, you hear about these long bear markets that are just brutal—the Great Depression. The markets were in a bear market for 10 or 15 years during the Great Depression.
You read about the late 1960s to the early 1980s, when the markets were crashing to zero. There was this brutal bear market from about 1972 to 1974. You heard Buffett talk about how he was an oversexed man in a harem because everything was so cheap in 1974. He was selling stocks at 5 times earnings to buy stocks at 4 times earnings and all that.
These were long, long slumps. I was just thinking about this. There was a little bear market, let’s say, from 2000 to 2002 with the dot-com bubble, but a lot of that was due to the inflation of the dot-com multiples. In fact, a lot of things that were more value-oriented sold very well in 2000 to 2002.
I’ve talked about this before. A lot of the value-investing legends today built their track records in 2000 to 2005, when the market was doing nothing and all these value stocks were tearing it up. They’ve lived on this for over 20 years.
Let’s fast-forward. You have a global financial crisis, and the market peaks in October 2027. It gets a little bit depleted when Bear Stearns and all that happens, but the peak of the global financial crisis was, let’s say, from July 2000 to March 2009. That’s about 9 months.
Since then, you have COVID, but the COVID correction in 2020 lasted maybe 2 months. It was from the end of January to the end of March, when everything hit rock bottom. You had tariff hysteria in 2025, but that was less than a month.
I wonder if the crashes are over. Maybe it’s because the markets are better. We have circuit breakers and Fed liquidity. People know that the Fed will provide liquidity. Why don’t we see these long recessions and bear markets anymore?
I don’t have an answer. Maybe we just live in a wonderful world, we’ve been lucky, and the economy has generally been good. I know many people who, both during crashes and over the long term, would point out that the Fed over-indexed and over-engineered markets and provided too much support.
Maybe people can say, “Hey, the reason we don’t have prolonged bear markets anymore is because of structural changes.” If you think about the 1970s, you had a lot of cars and a lot of steel, and they were really cyclical. You’re going to have a long bear market when the economy suffers.
Whereas today, you have a lot of really capital-intensive businesses, whether it’s technology companies before they went through the hyperscaler boom or McDonald’s, which is completely franchised at the moment. Perhaps they’re a little more recession-resistant.
I’m sure there’s a little bit of all of that, but it’s interesting to feel like we have a whole generation, or multiple generations, of investors who haven’t experienced anything more than a quick drop for a few months. I don’t know why the bear markets have gone away, and I think about what happens if we ever get into a really big bear market.
8. Fed put, fragility, and one big break
I think he has everything I say. I think that’s really interesting to think about.
And, you know, I think the other side of the question is that if you read something like Antifragile—and I realize I’m starting to sound a little bit like a guru—the market was over-engineered by the Fed. The economy, at the point when a recession starts, gets fiscal support, Fed support, all that. The moment the market falls, you get support from the Fed.
So what happens in a fragile system is that when you have all this support, it actually becomes more and more fragile, and you can have bigger breakdowns, right? Something that becomes increasingly brittle will have a larger breakdown, whereas something that is antifragile will have lots of small breakdowns, but that actually makes it stronger over time.
I was wondering—and there are other things that contribute to this, like zero-day options and all that stuff—if the market is prone to waking up one day and opening down 5%, and by lunchtime, wire after wire goes off and you’re down about 20% or something. I don’t know. Listen, I don’t claim to be an expert on market structure. It’s just something I was thinking about, and it all has to do with the structure of the market, rising interest rates, and the lack of huge recessions.
Hey, maybe the reason we haven’t had a long bear market is because, if the last one ended in the early 1980s, since then we’ve had this whole market backdrop from the 1980s to 2022 where interest rates were going down, or remained very low. Interest rates are rising slightly now.
So maybe the answer is, “Hey, Andrew, the reason we haven’t had a sustained bear market is because interest rates are falling, and we’re about to have a lot of long-term bear markets.” Even if stocks go up in the long term, they can really sell off, and one of the reasons they sell off is because financial gravity is starting to take hold.
9. Overconfident investors vs imposter syndrome
Okay. That was a long conversation about markets. Let me move on to investing.
I was talking about general things for investors. I was having dinner, I meant to say beer, but I don't drink, so I was having dinner with a friend, and he said, “Listen, there are 2 types of investors, and every investor falls into 1 of these 2 camps. There are overconfident investors, and there are investors who have imposter syndrome.”
I can’t tell you how much I’ve thought about that phrase. Every time I meet a friend, I’m like, “Does this guy have imposter syndrome, or is he overconfident?”
Let me just clarify. When I talk about imposter syndrome, I don’t mean an imposter in the sense of, “Oh my God, he’s pretending to be someone else.” I just mean imposter syndrome in the sense that, when you think about what’s going on in your head, you’re like, “Oh my God, I’m not really that good.” You have a lot of self-doubt and so on.
So I was thinking about which camp investors fall into. I’ll tell you right now: I know I’m a very nice man on the podcast. You may think otherwise, but I firmly belong to the imposter camp.
I’m still an 18-year-old teenager reading an SEC document. Often, when I pull the trigger on a deal, I remind myself, “Hey, you worked hard on this. You are an expert.” There’s no secret expert who knows everything and can tell you, “These are the real tricks.”
I hope you have some self-confidence. I hope you’re on the front lines, you’ve worked hard, and you need to believe in yourself and keep doing it. But I have to constantly remind myself of this.
So I think I have imposter syndrome. If you think I’m overconfident, well, maybe I am, but I don’t think so. I think I have imposter syndrome.
I was thinking about great investors. I was just thinking about a list of great investors, and I’m having a hard time coming up with anyone who wasn’t overconfident, or at least overconfident about something. Maybe that doesn’t speak well of me, since I consider myself to be suffering from imposter syndrome.
But, you know, empirically, all investors with great track records are overconfident. And the one who always comes to mind first is Buffett. He’s the GOAT.
At first I thought, “Oh, Buffett, he’s homespun, he’s humble, he lives in Omaha. He must have impostor syndrome.” Go and read "Snow White". Read about Buffett in his 20s and 30s, what he does and what he tells companies. This person is overconfident and embodies overconfidence.
So I wondered, why are all the great people overconfident? I think one of the answers might be, “Hey, Andrew, they’re big. They’re not overconfident; they’re just really confident.” That’s probably the case with Buffett, isn’t it? He’s great, he knows it, and he’s confident.
But there are other people who are respected whom I would put more in the overconfident camp. Even in Buffett’s case, when you read "Snow White," it’s interesting how many times things change for the better. I mean, Salmon Brothers—you know, something is happening with GEICO, and he’s like, “I just wrote a check to GEICO. This could be the end of me.” How many times does something change for the better?
John Malone has a lot of those stories if you read Cable Cowboy and all those books. Something changes for the better, and instead of being legends with a huge track record, they’re going nowhere, right? He’s the main character, but I was thinking about overconfidence and why all the great players, I think, are overconfident or have traits of overconfidence.
10. Survivorship: Archegos and Situational Awareness
I think the obvious answer is survival, right? We are all flipping coins in some sense, and if you’re going to do something, the overconfident investor will seek concentration and leverage, or both, which means high variance.
All the big players who are overconfident end up on the list of big winners, but we don’t see all the overconfident people who have hit 0. You can even see some overconfident people losing their alpha because they’re overconfident, because they’re too focused.
I think you would point to Bill Hwang from Archegos, right? Concentrated, leveraged bets continue to grow, grow, grow. They continue to buy on the way up. I don’t know what the exit strategy was there, but he goes from killing it to basically 0 overnight, right?
Situational awareness during the summer. There’s a great example with a concentrated AI thesis, and they just keep betting, betting, pushing and pushing. In the end, it basically doesn’t fall to 0 because, as I understand it, they still have a good track record and all that, but it’s pretty close to falling to 0.
It’s staggering. It’s like a manic state of madness. I mean, the public record is practically destroyed. Generally, these are just 2 examples, but I think it speaks well to overconfidence.
There’s a gray area of people who are not overconfident but who aren’t impostors, either. The other thing I thought was that big people have to raise money at some point, and maybe overconfidence also helps a lot in fundraising. Investors and LPs and everybody else want to invest in people who are overconfident.
So maybe you can’t attract an incredible number of fans and become one of the greats without a decent amount of money, and maybe overconfidence helps with money, too. So, yeah, I don’t know.
And look, there are counterexamples and outliers. My friend just mentioned overconfidence versus impostor syndrome, and my first thought was, “I’m an impostor.” Then I started trying to imagine how many great people are impostors, and I thought, “Oh, this is not good.”
11. Mentors: Ian Cassel's Stock Picker and Skip
The last thing I was thinking about—and then I’ll wrap up, because I guess I’m almost out of my time limit—is that a couple of weeks ago I had Ian Cassell come over to talk about his book, Stock Picking. You could hear it on the podcast.
I’ve had people with books on the podcast. Some of them I really like. You can hear them on the podcast. I really, really like Dean's books, and they really made me think about a lot of things.
In 1 of the chapters, he talks about his mentor. I think his mentor’s name was Skip, and he talks about how Skip taught him a lot. Eventually, he and Skip drifted apart because, if I remember correctly, he says, “Hey, I was growing and developing as an investor, and Skip was kind of a guy who stayed the same, right?”
He doesn’t say it’s bad. He doesn’t say he doesn’t like Skip as a person. This Skip, if you’ve read the book, has his flaws. But he just says, “Look, Skip had a style. He stuck to his style, and I kind of developed into my own style, so they started to diverge a little bit.”
It made me think about the fact that if you have a mentor, your mentor is always going to be the most impressive person in the world to you at first, or at least very impressive. Over time, they’re always going to become less impressive as you get to know them. You realize that they’re human and they have their flaws.
When you’re a day-one analyst, you don’t have a lot of skills or knowledge, and they seem to have decades and oceans and oceans of knowledge and experience. Then you start to accumulate some of that yourself.
If they have 20 years of experience and you have 0, they literally have infinitely more experience. Then, 5 years later, they have 20 years and you have 5, so they have 5 times more experience. Some of that experience is in different markets.
The knowledge gap and the skills gap are narrowing. Everything is different.
12. Even Buffett outgrew Ben Graham
In any case, why? I mentioned Buffett and Ben Graham earlier. Graham was Buffett’s mentor, but Graham is literally a legend. He founded value investing, but Buffett eventually moved on from Graham. So if Buffett can move beyond the founder of value investing and find new things—not that he thinks Graham is ignorant—then Buffett will evolve from that, just like everyone evolves from their mentor.
By the way, one of the reasons Buffett went away from Graham is that Graham apparently gave a late speech sometime in the ’70s, right before he died, where he said, “I’m no longer a fan of complex securities analysis. I like simple rules that apply to the entire market.” If you think about it, that’s kind of factor investing and quantitative investing. He was always quantitative; he tried to buy things on the net-net. But simple rules that apply to the entire market are the beginning of factor investing. So not only did he follow value investing and investment styles, but he was also, if you believe this, at the beginning of the factor-investing scene. I think it’s really interesting.
13. Wrapping up
Anyway, why am I saying all this? Well, I suppose people naturally move on from their mentors. Again, if Buffett does it, everyone will do it at some point. Is it because the mentor is not developing? That's how Ian Frampton describes his method in his book "Skip", and in the end he evolves and finds new things. Is it because the mentor is not developing, or maybe because you’re developing faster? I’m just curious, and I’m thinking about it.
I’ll say one more thing about mentors: you turn to mentors mostly because you’re early in your career and they know more. I think with mentors, it’s easy to find a mentor who’s overconfident because they’re often wrong, never in doubt. That thing about never doubting can really draw you to someone and make you want to be like them, make you want them to be your mentor, or make you want to follow in their footsteps. Maybe when you get to know them, you realize that they never doubt, but they are often wrong, and maybe that’s why you start to grow.
There are a lot of people who have mentors who are often wrong, never in doubt, and overconfident. They’re doing great when they’re 40, but it’s just a few flips of a coin. Then, when they’re 45 or 50, the coin goes the other way, and you have huge failures and so on. Maybe that’s one of the reasons why the mentees start to develop, because they see, “Oh, this person took a lot of risks, and those risks haven’t happened yet, but they could be about to happen.”
14. Journaling as a way to keep evolving
I don’t have the answers to any of these questions. I’ll tell you one thing that I’m working on developing. It’s funny because a lot of mentors and a lot of people I talk to insist on this, and I often support it, but I’m trying to do better. The blog serves as a diary for me in many ways, but I’m trying to write down more things and journal a little bit more, especially thoughts about the market: “Here’s what I think about the markets. That’s where I’m at in my head right now, where I’m thinking about the portfolio, all that stuff.”
That’s one way I try to do it. That way, I can use ChatGPT, and I don’t have to look at my notes. I can just compare how I feel today to how I felt a few years ago. I think about journaling and continuing to develop and push myself.
So, with that, I conclude my monthly September reflections.
I have some really interesting podcasts planned. I can't wait to share them with you. As always, thank you for listening to me, just randomly chatting for about 30 minutes into the microphone. I can't wait to talk to you soon. I can't wait for these podcasts, and we'll definitely see you next month with new thoughts.
A small caveat: Nothing in this podcast should be considered investment advice. Guests or the host may have positions in any of the stocks mentioned in this podcast. Please do your own research and consult a financial advisor.