Episode 363 - The (Underappreciated) Risk of Individual Stocks

26 Jun 2025 · 49 min

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Rational Reminder Podcast - Episode 363 Summary

Episode Title

The (Underappreciated) Risk of Individual Stocks

Hosts: Benjamin Felix, Cameron Passmore

Episode Overview In this episode, the hosts delve into the risks associated with holding concentrated positions in individual stocks. They emphasize the importance of diversification and discuss various studies that highlight the dangers of stock picking. The episode reveals how the odds are stacked against individual investors aiming for long-term success through concentrated stock portfolios.

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Key Points Discussed

Introduction

  • Welcome and In-Person Meeting: The hosts discuss their recent in-person meetings and the benefits of collaboration.
  • Advisor Adoption of Indexing:
  • Slow adoption of indexing among financial advisors due to cultural and compensation dynamics.
  • Rising demand and awareness of indexing among younger advisors and investors.

Main Discussion

Risks of Individual Stocks

  • Concentrated Portfolios: Many investors hold between 3 to 7 individual stocks, which increases risk.
  • Example of Nortel: Illustrates the dangers of holding onto a stock due to perceived tax implications and the illusion of "free" stock.
  • Skewed Return Distributions:
  • Data from JP Morgan's "The Agony & Ecstasy" report: 44% of stocks in the Russell 3000 index experienced catastrophic losses.
  • Individual stocks are often riskier than perceived, particularly recent winners.
  • Behavioral Biases:
  • Overconfidence and Familiarity Bias: Investors often overestimate their ability to pick winning stocks and underestimate risks.
  • Idiosyncratic Risk: Unique risks associated with individual companies that do not offer a positive expected return.

The Concept of Diversification

  • Benefits of Diversification:
  • Reduces risk without decreasing expected returns.
  • Identified as the only "free lunch" in investing.
  • How Many Stocks for Diversification:
  • Traditional views suggest that 20-30 stocks are sufficient, but newer research indicates that significantly more (250+) may be necessary for effective risk reduction.

Research Highlights

  • Bessembinder Study: Shows that only 45% of actively managed funds outperform the market after fees.
  • Recent Studies:
  • A 2023 study found the median return of individual stocks is negative compared to the market over 10 years.
  • Stocks performing well in the past are more likely to underperform in the future.

Psychological and Economic Barriers to Diversification

  • Investment Biases: Include representativeness bias, endowment effect, and status quo bias, which impede decision-making.
  • Economic Factors: Taxes associated with selling appreciated stocks can deter investors from diversifying.

Conclusion

  • The hosts conclude that individual stocks are inherently risky, and while a few stocks may yield extraordinary returns, the likelihood of picking them is low. Diversification is a critical strategy for mitigating risks and should be approached thoughtfully.

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Important Quotes

  • On Diversification: "Diversification reduces risk without reducing expected return."
  • On Individual Stock Risks: "Picking any one stock is more likely to lead to a bad outcome than a good one."

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Additional Resources

  • Papers Discussed:
  • *The Agony & The Ecstasy* - JP Morgan
  • *Why Indexing Works*
  • *Underperformance of Concentrated Stock Positions*
  • *How Many Stocks Should You Own?*

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Links

  • [Rational Reminder Website](https://rationalreminder.ca/)
  • [Listen on iTunes](https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582?mt=2)

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Final Thoughts This episode serves as a critical reminder for investors to assess their portfolios carefully, understand the risks of individual stocks, and consider the power of diversification in their investment strategies.

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Transcript

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0:03This is the Rational Reminder Podcast, a weekly reality check on sensible investing and financial decision-making from two Canadians. We're hosted by me, Benjamin Felix, Chief Investment Officer at PWL Capital, and Cameron Passmore, CEO at PWL Capital. Welcome to episode 363. Great to be back on. Great to see you, Ben. Great topic today. Great to see you too. It's a rare week where we've seen each other twice in person. In person. And you had a chance to get back to your home studio, but it is nice. We had a great day here in the office actually to have lots of people in. And so Tessa was in, your sister, which is always fun, and lots of other people.

0:39Yeah, that was good. We tried to do a weekly breakfast, but the breakfast place we would go to shut down, unannounced to us. They had to travel and stuff. So we finally got back to it today at a local diner. So fun to get that tradition back and seeing people again, which is good. Work from home is great. Working home is very productive and efficient. But being in person, you pick up on stuff and kind of get a different gauge on the temperature of everybody. Yeah, it's a different feel for sure. It has been nice to run into people in the office. Also very nice to be able to work from home. Oh my gosh, absolutely.

1:08I got a question for you around this, but something I've been thinking about lately as we've been talking to lots of advisors about their futures and whether or not they might want to join the movement that we're part of, is you got to think with the low level of adoption of index funds, dimensional, whatever markets work, systematic framework, you got to think awareness of that is increasing inside the advisor community. However, the uptake is so slow. So I just kind of have an open question, like are there advisors out there? Do you think that are actually wanting to make this transition? But often in some of the larger firms, you might be the black sheep if you do that.

1:45So you might be ostracized, you don't have the support you want. There might be perhaps compensation, conflicts of interest because there's so much more total overall revenue from active portfolios versus index funds. It's a dynamic I just find interesting. That piece I think is getting better because even in the old mutual funds channel where I started, where you couldn't sell a fee-based fund if you wanted to, and you couldn't sell an ETF if you wanted to, those channels are much more open now to fee-based products and to ETFs in some cases. That's not even conflict at that point. That was just a structural inability to use those types of products.

2:20That's gone away. I have talked to advisors who are in that channel or similar channels or similar environments and are realizing that maybe this index investing thing does make a lot of sense because you focus on the planning, you focus on the client, which is what people on those channels are trained to focus on anyway. But there's just this weird actively managed fund thing going on. But I think there's more awareness coming about the benefits, not just to the client's performance or expected performance, but also to the overall quality of the relationship that an advisor can have with a client when the investing piece is kind of treated as solved or whatever you want to call it, the way that we treat it.

2:57Not to mention the demand side. There has to be more consumers demanding this. The awareness has to be going up. We're playing a small part of that, but I listened to David Chilton's podcast yesterday and he mentioned the power of index funds and he highlighted this podcast and your YouTube channel on that in its conversation with Amanda Lang, which is a great conversation. But that awareness is increasing all the time. It's the demand side. And I'd also add, you look at the people that we've been fortunate enough to meet and have joined our team as young advisors. The young crowd certainly understand this and get it.

3:30Yes, we have a buy sample granted. That's why they wanted to come here. But the young people are so aware of this has been my experience. So I just find the dynamic interesting. And if there are advisors out there that might want to be part of a team that does things this way, we'd be open to a conversation. And it's been happening. Since Dimensional came to Canada in 2003, they've been slowly adding more and more advisors in Canada. Lots of people that we now know, Cameron, but even 10 years ago, a lot of those people that are in that community were not investing this way. We know from the data too, that shift is happening.

4:03It's just happening more slowly in Canada. Sure is. So the topic for today? Main topic today is the risk of individual stocks. It's just kind of antithetical to index funds. It is. Should we get into it? Let's get into it.

4:20A lot of investors hold concentrated positions in individual stocks. That can happen a lot of different ways. I have a line here that's kind of a joke, but it can happen when you hear Charlie Munger say that diversification is for the know nothing investor without realizing that he's talking about you, kind of a dig at people because Charlie Munger has said that. But I think a lot of people hear that and say, well, that's not me. I'm not the know-nothing investor. I'm going to hold a concentrated portfolio because Charlie Munger said so. But of course, Munger, when he was alive and Buffett are very different from most people.

4:54I think a lot of people do hear Buffett and Munger talk about diversification being silly and concentration being smart, if you know what you're doing. People hear that and think, well, I know what I'm doing, so I'm going to concentrate my portfolio. So that's one that is kind of like an overconfidence type thing, I guess. Then there are other reasons like being part of a company that went public and holding onto your stock either because you wanted to, because that's what everyone else was doing or because you were in a lockup or whatever and the price went up. All of a sudden, you've got this huge position in a single stock.

5:22Or even just like a lot of people get a portion of their compensation in employer stock. So it could be other things like owning stock in an employer that has just performed so well over time that it becomes a big part of your portfolio. I mean, I can imagine working at NVIDIA and receiving equity compensation. And then all of a sudden it's like, oh, wow, I've got a very concentrated position. Or if you sell it and you got a low cost base. I'm sure I mentioned that discussion around a client that held Nortel a long time ago. I don't know if you have. It's a cool story. This goes back to Nortel soared in what, 2001 to actually get the price, doesn't matter.

5:54I think it was like in the low 100s. I said one client that had this huge concentration position in that single stock Nortel and all I can't sell is the tax will be so expensive. That was the tax advisor's advice. My colleague at the time did the math and said, well, if it goes down below whatever,$91, you will evaporate all the tax savings. So, if you think there's a chance it goes below 91, you should sell because it's irrelevant. Oh, no, no, no. Went back and forth, back and forth. The advisor went right to the wall, convinced them to sell. So they sold almost at the peak. We all know what happened to the Nortel share price.

6:29One of those types of stories where you look back and it's like, wow, a lot of those employees had huge concentrated positions in their employer stock. And they just loved the company, which is great. I think they'd done a butterfly transaction from Bell. I guess Bell owned Nortel and it spun out. So a lot of people viewed the Nortel shares as free money, which of course it wasn't. Interesting dynamic that's 20 plus years ago. Yeah, it's a great example. It's super relevant to the topic that I'm going to go through here. In any case, however you end up getting there, owning this concentrated position in a single stock, and to the point of the example you just gave, I don't think people are aware of how risky individual stocks are.

7:07We know that in aggregate, and this is kind of the Scott Cederberg stuff, but other people have covered this idea too. In the long run, in aggregate, stocks are probably a bit safer for long-term investors than I think a lot of people realize. But I think individual stocks are way riskier. than most people realize. One interesting thing that comes out of some of the research that I'll talk about here is that that is especially true for stocks that have performed well in recent history. The chances of an individual stock that's performed well in recent history underperforming in the future, the chances are greater and the magnitude is also greater.

7:39Which stocks do people tend to own concentrated positions in? Well, the ones that have done well recently, not the ones that have done poorly. What I want to do in this episode is detail how risky individual stocks are, which again, I don't think most investors appreciate that, and also cover how many stocks are needed. There's no single right answer here, but I'm going to talk through just how to think about how many stocks are needed for a portfolio to be diversified and why it's more than the commonly cited 20 to 30 stocks, which is a number that I hear thrown around quite a bit. That's a number that is based on research, but it's based on research that's from many, many years ago when we didn't know quite as much about financial markets, when risk was framed in a different way.

8:20One of the reasons I think this is an important topic is that it's pretty well documented that individual investors do quite commonly hold concentrated portfolios. I saw some research showing that at least in their sample, individual investors on average held between three and seven stocks, which is crazy. I don't have really good data on this to confirm what does it look like. If you go to Questrade accounts across Canada or TD, direct brokerage accounts across Canada. What are those portfolios? I would love to know. I don't have those data. But if you talk to people who don't invest in index funds, but invest in stocks, or if you look at the investing subreddits where people are talking about the stocks they invest in and their portfolios, that three to seven number actually doesn't seem too crazy.

9:01That's anecdotal, but the three to seven is based on research. But anecdotally, it's not actually that crazy for me to believe that it's good data. I guess they haven't heard of a Bessembender. They probably have not. Or they have, and they think that they're holding the three to seven stock. You're right. That's the thing with Bessembender. It cuts both ways. Cuts both ways, yes. That concentrated portfolio behavior that is more pronounced, and there's a paper on this too, that is more pronounced for investors who overweight the unlikely probability of a big win relative to the much more likely probability of losses or underperformance.

9:33If that's you, I suspect it's not many of our listeners, but if it is you, listener holding a concentrated portfolio of stocks, you're going to want to hear us out in this episode. Do you think it's the human's tendency to like stories over math? Stories of stocks can be very compelling, which can drive your conviction. I know there's no evidence. I'm just thinking of what could cause that. Well, there's no evidence of that exactly, but if you go up a level of abstraction, there is evidence that people overpay for growth. I think stories are probably a big part of that. Narratives matter. Individual stocks, of course, are exposed to something called idiosyncratic risk, and that's risk specific to that company, what its CEO happens to tweet or whatever random thing that happens specific to that company, separate from what's happening to the broader market or even to similar companies.

10:20It's a type of risk that does not have a positive expected return. In general, and this is pretty basic portfolio theory thinking, investors should try to avoid idiosyncratic risk by diversifying their portfolios. A broadly diversified portfolio, like take a total market index fund, is primarily exposed to market risk, which is again, a risk with a positive expected return. Now, the cool thing about diversification is that it reduces risk without reducing expected return. You're reducing your idiosyncratic risk. You're not reducing your portfolio level expected return, which is why diversification has been referred to as the only free lunch in investing.

11:00Typically, if you want more expected return, you have to take more risk. Or if you want less risk, you have to reduce your expected return. Diversification is the exception. Exactly. Now, if diversification is the only free lunch in investing, I've got another joke here. I don't know. See how it goes. Then portfolio concentration is like ordering fugu prepared by an amateur chef. Fugu is like poisonous puffer fish. if you prepare it wrong, then it's... Another joke's funny. Okay. If you had to explain a joke, it didn't really land. In my YouTube video on this topic, I did have a clip from the Simpsons with an amateur chef very nervously preparing fugu.

11:39And I'm pretty sure Homer ends up getting poisoned. So maybe it was better with a visual aid. Such a great episode. So a concentrated portfolio, what does that actually mean? We have to put some definitions around it. I'm going to call it a portfolio with a single position that makes up 10 % or more of its holdings by weight. Now, that is a figure that's based on one of the papers that I'm going to reference later in the episode. The most concentrated position would be holding one individual stock or maybe levering up an individual stock, I don't know. But one individual stock is as concentrated as you can get in a single position.

12:11And then each additional stock after that makes the portfolio more diversified. The reason that concentrated portfolios are problematic is that they allow the idiosyncratic risk, that uncompensated random risk of the individual company to have a meaningful influence on the outcome of the portfolio as a whole, which isn't great. That wouldn't be terrible if most stocks performed really well. If every individual stock earned the market returns, oh, who cares? We don't need to diversify. But the data on individual stock returns, they're pretty sobering. You mentioned Bessem Bender, Cameron, and that's some of the data I will talk about, but there's a bunch of interesting research on this.

12:46One of the most accessible, and this one's been around for a long time too. I think Bessenbender does reference it in his paper, or at least he acknowledged it when we talked to him. But JP Morgan puts out this occasionally updated report called The Agony and the Ecstasy. And it's all about individual stock returns. They look at the range of outcomes for individual stocks and they slice the data up different ways in various issues of this report. I think they've been doing it since 2005. They've come up with a few different versions of it. In the 2021 issue, one of the data points that jumps out at me, I just find fascinating, is the frequency of catastrophic losses.

13:22That's defined as a 70 % decline in price from peak to trough, which is never recovered from. We're talking about the Russell 3000 here. 3 ,000 stocks in the US market that make up a huge portion of the US market. 44 % of companies that appeared in the Russell 3000 index from 1980 through 2020 experienced a catastrophic loss. Some sectors like energy, they slice it up by sectors, energy, information, technology, they have even higher frequencies of catastrophic losses. Staggering number, 44 % of the stocks that appeared in the Russell 3000 index, which is representing most of the US market over this 1980 to 2020 period experienced losses of 70 % or more that they never recovered from.

14:04And the question is, how do you behave when that happens? That's part of the question, but it's also just, what does that do to your financial future if that was your one stock. Exactly. Because it doesn't recover. So even if you behaved well and held onto it, it doesn't mean it's coming back like a typical market return. That's what I'm saying. We don't get that mean reversion that tends to make stocks in aggregate, the stock market a little bit safer for long-term investors than I think people generally think. This idiosyncratic risk or the potential for catastrophic losses that you never recover from, it just makes individual stocks a lot riskier than I think people imagine them to be.

14:37I don't think it should be too surprising. The first time I read that statistic, I was like, wow, I didn't expect it to be that high. But capital markets are highly competitive. They're driven by creative destruction. Some companies are going to succeed to the point where they displace companies that had previously been successful. And some companies are going to fail or at least struggle to compete. And that'll be reflected in their prices. We know in aggregate stock returns are positive and we expect that to continue for the same reason, creative destruction. but within those positive aggregate returns, there are going to be a lot of losers.

15:10Another interesting point from the JP Morgan report is that despite the S &P 500's incredible performance of the index as a whole, hundreds of companies cumulatively have been removed from the index over time due to business distress. That's also an interesting point because if you took that diversified portfolio of companies that were removed from the S &P 500, I think they've probably performed quite well, but it does drive home the point of creative destruction. The other issue is the skewness point. The idea that by number of stocks, there are much more losers than there are winners. The winners tend to win really big, but there aren't as many of them.

15:42Over the 1980 to 2020 period, 42 % of stocks included in the Russell 3000 had negative absolute returns. Negative. 42 % of stocks. 66 % of stocks trailed the market, trailed the Russell 3000 as a whole. 10 % did beat the market by accumulative over the full period, 500 % or more. Then the JP Morgan report, they call those mega winners. That phenomenon, the distribution that I just described, that's called positive skewness. Most stocks perform poorly. A few do exceptionally well. I think the investors holding individual stocks are overweighting the probability of holding a mega winner and underweighting the much more likely probability of holding a loser.

16:26It's so interesting to think of why. Is it the greed? Is it the over-optimism? is it you have an optimistic bias in general? If you look at this evidence, is it glass half full or glass half empty? That's an interesting question. It takes all those characters to make a market. It's so interesting to think of what goes on. Then when you think of who's on the other side of the trade, that's where my head goes. When you're buying or selling, there's someone on the other side, you have no idea who it is, but it's likely someone pretty sophisticated. Just by volume of trading, it probably is someone sophisticated.

16:57I assume if you get one right and it's a massive winner, must be so intoxicating. That builds up your confidence. We all get it. It's an incredible phenomenon. I've already released a YouTube video on this topic and the comments were fascinating because there were people who have beaten the market by picking stocks. They think that I'm completely insane for saying that you can't beat the market by picking stocks. Of course, they'd think that based on their own experience. Then there are also a lot of people who have lost a lot of money picking stocks. They're saying, yeah, this video makes a lot of sense.

17:28Then in some cases, there are little comment discussions where the people who have made money picking stocks are debating with the people who have lost money picking stocks, whose experience is more representative of what people should expect. But it's hard when you have a lived experience that's like, I picked stocks and I beat the market. Being convinced that you were lucky or that you won't be able to repeat that outcome again in the future, that's not easy to convince somebody of. Because like, hey man, I lived it, I did it. in the video here, we can show the distribution of stock returns from 1980 to 2020.

18:00We'll pull the chart up. But what you can see is that most stocks underperform, as we've been saying, a relatively small portion match or beat the market and a few do exceptionally well. That's the positively skewed distribution. That means as per what Bessenbender talked about when he was on, if you're selecting a small number of individual stocks for a long-term portfolio, it is much more likely that you pick stocks that underperform than you pick stocks that outperform. That's why diversification makes sense in general and why total market index funds in particular, which hold all the stocks in the market, are so hard for active management to beat.

18:35That intuition is detailed in a 2017 paper, Why Indexing Works, which shows using just a simple toy model that when the distribution of returns is positively skewed, randomly selecting a subset of securities from the index dramatically increases the chance of underperforming the index. And then that simple model is of course validated by Bessem Bender's paper, Mutual Fund Performance at Long Horizons, where he finds that the pre-fee returns of only 45.2 % of actively managed US equity mutual funds beat the net of fee returns of SPY, an S &P 500 ETF, over the same period. That to me is crazy, that only 45 % of pre-fee mutual fund returns before fees beat the net of fee returns of SPY.

19:19Wow, pretty fee. Yeah, I know. It's wild. And that's just the skewness. That's the skewness of returns. You add in fees and it looks much worse. But the fact that you're more likely to underperform before fees because of the skewness, and those are much more diversified portfolios. Actively managed funds tend to be fairly concentrated, but relative to 10 stocks that an individual investor might hold, they're much more diversified. To your point, Cameron, about what is driving this, I think one of the reasons is likely that investors holding individual stocks think they know the companies that they own and that they understand the distribution of potential outcomes, the risks and opportunities that that investment represents.

19:58I would call that familiarity bias. Investors are more comfortable with what they know. There's probably some illusion of control bias too, where investors feel like they have some level of control over the outcome because they've done research or because, I don't know, maybe they work at the company or they know the management or whatever. The reality that investors have to understand is that the factors that drive underperformance and the catastrophic losses that we've mentioned are really unpredictable. The JP Morgan study has some interesting data on this. They look at how things like commodity price risks that cannot be hedged away, changes in government policy, deregulation and re-regulation of industries, foreign competition, trade policy, and fraud by company employees in their sample are some of the completely unpredictable things that have caused past business failures.

20:43Their commentary on this is that these are just things that no matter how well a business is run or how well you understand it, they can completely blindside its profitability, which can lead to big stock price declines. Another thing is the declines happen quickly and unexpectedly. Another one of the comments on my video on this is that, oh, you've never heard of a stop loss. I guess if you have that in place, maybe it'll help on the downside. But I think these declines happen quickly and unexpectedly. The 2024 issue of JP Morgan's report, they show a chart with a sample of companies that have experienced catastrophic losses, and they've got the magnitude of the loss on the y-axis and the maximum monthly rate of decline on the x-axis.

21:23It shows that companies of all sizes have experienced big losses that happen really quickly. The average monthly losses are just enormous. By the time that it's going down, it's in many cases going to be too late. The other thing is once it's going down, people will want to hold onto it until it's recovered. Until it comes back up, that's the disposition effect. But with the catastrophic loss data, we know that in a lot of cases, once the stock goes down like that, there's a good chance that it never recovers, or even continues to decline. I think another interesting point is that from the JP Morgan report again, people often believe that this company, whatever it is, I don't know, maybe Bell is a good recent example, that catastrophic losses can only happen to companies with weak financials or overvalued companies or companies within certain risky sectors.

22:11But the reality is they happen across sectors. They happen to profitable companies. They happen to companies with moderate debt ratios and to companies with reasonable valuations. I think that's another just important point is that investors have to realize that even a well-run and successful business can suffer the catastrophic losses or extreme underperformance. Another interesting one from that report is that investors will use analyst consensus. I've talked to real people who do this. Well, I think I'm going to hold the stock as the analyst consensus said strong buy. So JP Morgan looks at that too.

22:44They find that the vast majority of catastrophic losers in their sample actually were consensus buys or strong buys from analysts prior to their declines. No way to hide from that potential for loss. Going back further in time, so that JP Morgan study was going back to 1980, the 2018 Bessenbender study to stocks that outperformed treasury bills. They look at all US stocks that existed in the CRISP database from 1927 through 2016. They do find pretty similar results to what JP Morgan found. 42.6 % of common stocks have a lifetime buy and hold return that exceeds one month treasury bills. which is crazy.

23:24People have heard those data from Besseminder before and from us talking about these data. More than half the time, you're better off holding risk-free treasury bills than individual stocks over that time period, which is wild. 30.8 % of individual stocks in this sample beat the value-weighted market, the index. That's pretty similar to the J.P. Morgan study. More than half of the stocks in the sample deliver negative lifetime returns. That one is higher than the JP Morgan study. I think that's probably because it includes all stocks in this case, including the tiny ones that are in the CRISP database that are not in the Russell 3000.

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23:59It also extends to the lifetime of stocks rather than the 1980 to 2020 sample period that JP Morgan used. The data in Besseminder's study are a little bit better at the 10-year horizon compared to the lifetime horizon. At the 10-year horizon, 49.5 % of stocks beat treasury bills, 37 % beat the market. But still, brutal numbers if you're picking stocks hoping to beat the market. Then there's also the global skewness data. Bessenbender has his US paper. He's also got a global stocks paper. The skewness in global stocks is even worse than it is in US stocks. You're not making a compelling case to stock pick.

24:35Well, I don't think there is one, really. It's kind of the idea. This is a cool paper. There's a 2023 paper, Underperformance of Concentrated Stock Positions. They use a set of all US stocks, but they exclude the smallest stocks from 1926 to 2022. The way that they describe their data is that in more recent history, it looks like the Russell 3000, but they also go back further in time when there were fewer stocks in their index, but they have a size cut off. They take a slightly different perspective, but they're again looking at concentrated positions. So the author finds that the median 10-year US single stock return in their sample is a cumulative negative 7.9 percentage points relative to the market.

25:16That's about 0.82 percentage points in annualized terms. And also that 55 % of individual stocks trail the market at the decade horizon. They also show how the volatility of a portfolio changes with an increasing weight in a concentrated position by modeling various portfolios consisting of the market index and an increasing allocation to an individual stock. And what they find, this is where that 10 % being the definition of a concentrated portfolio comes from. They find that portfolio volatility is relatively unaffected by single stock positions at weights up to 10%, but then increasingly affected thereafter.

25:53And the effects are more pronounced for individual stocks with higher idiosyncratic volatility, which makes sense. If you hear all this pessimistic data and think that, well, nobody would buy a loser stock. I only buy winning stocks, or I only hold my stocks have been performing well. This is the fascinating data point from this paper. Stocks with top 20 % performance over the past five years have a median cumulative return over the following 10 years of negative 17.8 percentage points relative to the market. That's an annualized 1.94 percentage points. 60 % of these stocks, as opposed to 55 % of all stocks, trail the market at the decade horizon.

26:31And recent winners, like the stocks that, like I said earlier, I would argue are the ones that are more likely to make up a larger portion of investor portfolios. Those ones perform worse, not better at the 10-year horizon. Pretty interesting. That applies across all industry groups and also among both the smallest and largest stocks. Like you said, Cameron, I'm not making a great case for investing individual stocks. I think the important takeaways from these studies are that positive skewness in individual stock returns means that you're much more likely to pick a loser than a winner when you're selecting an individual stock.

27:03And the effects of skewness are more extreme at longer horizons. So that means that the chances of being a successful long-term buy and hold investor with only a few stocks is increasingly unlikely at longer horizons. However, like we said, Bessemender cuts both ways. If you do pick the rare winners, the results can be extremely positive. And the other thing is underperformance can happen quickly, unexpectedly, and irreversibly. A lot of stocks not only underperform the market, but they suffer catastrophic losses that they do not recover from, unlike a diversified portfolio, which tends to bounce back.

27:38It is worth emphasizing that it is true that a small number of stocks perform exceptionally well. It's just really hard to pick them before the fact. And past winners are more likely to underperform than outperform in the future. Some level of diversification probably makes sense, as we know. That's another interesting question, though, is how much diversification makes sense. Individual stocks are risky, fine. So we should diversify, fine. How many stocks should you own? What is a diversified portfolio? There are a couple of papers, very highly cited papers from the 1970s and 80s that find kind of a 20 to 30 stock portfolio is sufficient for diversification.

28:17And the way that they approached is that beyond that point, the risk reduction benefits diminish. Now that 20 to 30 stock finding has colored the beliefs of many investors. The problem with it is that it assumes that volatility is the only measure of risk that matters to investors. They show that the volatility reduction benefits of additional stocks levels off after 20 or 30. I would argue that what matters to investors is the expected distribution of long-term wealth outcomes, not the short-term volatility. If you think about a more concentrated portfolio has a small chance of holding the mega winner and a much larger chance of holding the losers, even if they have similar volatilities, I don't know if they would, but say they have similar volatilities, the difference in wealth accumulation between the worst and best concentrated portfolios is going to be huge.

29:04It's going to be enormous at long horizons. Reducing volatility is for sure a good thing. That's one of the things that diversification can help with. The other interesting thing is that at very long horizons, even small differences in volatilities can have big impacts on long-term wealth accumulation. Really interesting. We talked about this in some of our earlier way back episodes about concentration versus diversification in factor investing. We talked to Wes Gray about that. Wes Gray, exactly. It is a very interesting topic. There is a 2022 study by Roni Israelov, how many stocks should you own?

29:39They simulate long-term wealth outcomes for portfolios with varying levels of concentration. They find that the 25th and 10th percentile outcomes, so basically the worst outcomes in their simulations, improve quite dramatically until around 250 stocks are included. Then the incremental benefits of diversification really decrease after that. The average portfolio in their simulations multiplied wealth 19 times over 25 years on average, but an investor with just 25 stocks had a one in 10 chance of receiving less than a 12 times multiple. An investor with 250 stocks had a one in 10 chance of achieving less than a 17 times multiple of wealth.

30:20See that distribution is a lot wider. The left tail is a lot worse with a more concentrated portfolio. The worst outcome is less bad. The best outcome is also less good, which is interesting because that's not necessarily a good or bad thing. It does make the choice about how diversified a portfolio should be a preference more than a prescription. You can't just say, well, you should have this many stocks. but I think it's worth highlighting that when risk is measured as the variability of terminal wealth, the diversification benefits of adding more stocks does continue far beyond that 20 to 30 holdings that sometimes get cited.

30:53If you're confident you can pick winning stocks before the fact, portfolio concentration can make sense, but the odds are stacked against you. The track record of active management in general does leave much to be desired as we know and as we mentioned with Bessenbender's research. It is worth saying that some investors may be comfortable with that risk. They may be willing to accept a wider range of long-term outcomes, including a good chance of trailing the market or even suffering a catastrophic loss in exchange for a smaller chance at extreme outperformance. It's like a preference for a lottery-like payoff, which you can't say is right or wrong, but I think it is just a risk that needs to be properly understood for anybody holding a concentrated portfolio or for holding a single stock.

31:35Bessenbender's do stocks outperform on treasury bills, he simulates long-term returns for 20 ,000 portfolios of randomly selected 5, 25, and 50, and 100 stock portfolios. He finds at the 10-year horizon that even 100 stock portfolios outperformed the market only 47.5 % of the time. That was a crazy finding from his paper too. Now, there are a few different ways to interpret that result. One way is that, well, hey, it was only a little worse than a coin flip that you would have beaten the market before costs. The other is that you had more than a 50 % chance of trailing the market. Now, the nice thing about total market index funds, and even I think I would group dimensional funds into that category because they still own that broad cross-section of all the stocks in the market.

32:18The nice thing with that approach is that you know you're going to get the market return in the case of dimensional plus or minus some factor premiums, but you know you're going to get the market return even if you don't know what the market's going to be. With a really concentrated portfolio, you might still get the market return, but it's going to be plus or minus the active return from portfolio concentration. And that range of outcomes for the active return is going to be a lot larger with increasing portfolio concentration. And the distribution of outcomes of all the concentrated portfolios is going to have lots of losing portfolios and a few big winners.

32:51And that skewness will decrease as you increase the diversification of the portfolio. There is research from Vanguard showing that active share, which is not the same thing as concentration, but it is related. We actually have an episode with Martin Kramers, who created that measure coming up. Vanguard has research showing that higher active share results in a wider dispersion of benchmark relative returns for actively managed funds. It becomes a question of how confident you are that the stocks you pick will be winners rather than losers, while keeping in mind that the distribution of individual stock returns is pretty intimidating.

33:26Another interesting point here is that portfolio concentration can have asymmetric effects on performance. There's a 2022 paper, Fund Concentration, a Magnifier of Manager Skill. The author finds that increasing concentration has a pronounced positive impact on performance for outperforming funds, which makes sense. If you take more concentrated funds that have done well, they will have done well more so than more diversified funds. But the opposite is true for underperforming funds. And this is a really interesting point though, higher levels of concentration generally hurt the poorly performing funds more than it helps the outperforming funds.

34:02This is another interesting point on the concentrated positions thing. We talked about a few different paths that you could have taken to end up with a concentrated position, but most of those paths lead to both or some combination of economic and psychological barriers to diversifying. I think the biggest economic barrier, we talked about this earlier with the Nortel example, is taxes. You own a stock that increased in value substantially, leading to it being a concentrated position, there's probably a large tax bill associated with selling it. An important thing about it in that case is that the taxes generally don't go away, at least not in Canada.

34:35In the US, there can be some estate planning, but in Canada, the tax bill doesn't go away. The only thing you can do is control whether you realize the gain now or later, because it's coming no matter what. Deferring taxes can be a good thing, but in this case of a concentrated stock position, it is being traded off against taking a large amount of idiosyncratic risk. There are some strategies in Canada like tax efficiently donating the appreciated securities that can make sense. If you're going to make a donation anyway, then this can make sense. Donating them for the sake of donating them when you wouldn't have otherwise, that's not really helping you with your tax bill.

35:10It sort of is, but you're also giving away the assets. But if you're going to make a donation anyway, this can be a very tax efficient way to do it. But that said, it's a relatively complex planning and it's got to be approached very carefully and in the context of the overall financial plan. Another less common economic constraint that can still be relevant is control. Some large shareholders of a company that have a concentrated position may need to maintain their large position in order to maintain voting control of the company. That's obviously a much harder one to overcome. The psychological constraints to diversifying include the representativeness bias where people ignore the types of base rate probabilities that we've discussed in this episode and assume that their past performance with a single stock is indicative of its expected range of outcomes.

35:53There's also the endowment effect where people prefer things that they already own. There's the status quo bias to stick with the thing that you're already doing. I own this stock, so I'm just going to keep holding it. It's easier to not make a decision than it is to make one. And in the case of a stock that's fallen in price, we also have the disposition effect. So managing those biases with respect to diversifying a single stock position can be challenging. A couple of things that can help. One is imagining that the amount you have invested in the single stock is in cash and asking yourself if you would buy the stock today.

36:25And then another one, and this is one that I got from someone who I told the first one to, and I kind of took it away and thought about it. And they came back and said, I tried doing that. I tried imagining that it was cash and I wouldn't have bought it, but it didn't help me sell. I was still stuck. And so they came up with something that did work for them, which was creating a systematic plan to dollar cost out of the concentrated position. So it avoids the psychological impact of making one big decision and having it not work out. Makes sense. I'm still in the cash camp. I find that one pretty effective.

36:55I like that model too, but it doesn't work for everyone. And if it doesn't work for someone and dollar cost averaging out, if someone says, I just can't do it, I can't sell the whole position. I like putting something systematic in place. It's tough being a human. Well, it's tough investing as a human. Humans are not designed to be long-term investors in these abstract financial instruments that we call stocks. So stocks are extremely risky, as I hope we have articulated. Most of them by number underperform the market. Many of them have negative long-term returns or more extreme catastrophic losses, and a smaller portion of them have extremely high returns.

37:32Picking any one stock is more likely to lead to a bad outcome than a good one. And counterintuitively from one of those papers, that is even more pronounced for stocks that have performed well over the last five years. So the simple answer is to overcoming individual stock risk is of course diversification. The extent of diversification that makes sense depends on your preferences for skewness. Some people might want skewness. Also your conviction in your stock selection ability and your willingness to bear the risk of a wider range of potential outcomes. And then getting out of a single stock position.

38:04It can have economic and psychological challenges, but those can be overcome with thoughtful planning. And that's something that we've seen many clients do. All right. You've convinced me. Mission accomplished. That's good. I'm a changed person because of this. Glad you're convinced you're going to go sell all of your Tesla and NVIDIA shares. That's right. I'll get on that right now. So I have to ask you, where did this idea come from for this? I'm just curious in the process. I'm guessing a lot of listeners have a similar question. Where did the idea for the specific topic come from? I don't know.

38:38Did this come out or does it come from a client or from a comment or just came to you? I can't remember. Some people think there's some sort of master communications plan behind all this. And we've said many times, no, this is a pretty messy omelet making station. I'd love it if someone came to me and said, Dan, you should make a video about this, then I could do it. So here's my next question. So you come up with a topic. what's your process to then go and discover it? Because you referenced many papers and studies here. What's your next piece of the process? For this one, I think it might've just been that there were a few papers that I had read on this, like the Bessem Bender papers that everybody's read.

39:15Everybody. I mean, maybe not everybody. I've read them. But they're familiar with a lot of people. It's fair to say that. Yeah. And then there are the JP Morgan studies that I've read those before Bessem Bender had written his 2018 paper. I'm aware of those. They're connected and they're slightly different data, slightly different ways of presenting the analysis. Then there's the more recent one, there's the 2023 paper, the underperformance of concentrated stock positions. How do you find them? Do you go to SSRN and search or you chat GPT? How does that process happen? I have no idea. Sometimes it'll be something as simple as I'll be looking somebody up as a potential rational mind or guest.

39:52And when I do that, if I've seen a few papers from somebody and I'm like, this person could be interesting. So I'll go and look them up on SSRN or on their university website if they're at a university. And I'll go and just flip through their papers, their working papers and their published research. And in many cases doing that, they don't rank well on Google academic papers. And so I'll find a paper that I hadn't seen before. I think that's how I found the underperformance of concentrated stock positions. and then I go and read it and it's like, oh, it's another interesting perspective on that topic, on individual stock risk.

40:22For this video, there were enough unique perspectives. The Bessenbender paper, there's the JP Morgan studies. There's the Antipedisto paper that I hope I pronounced the name correctly. That's the underperformance of concentrated stock positions paper. And then the Roni Israelov paper on how many stocks you should own. That's probably enough content to talk about for a video. So then I just write it up into a video. So you read them, you think about it, you get your outline, catalog the studies. I assume you get them saved in a database or something, you cross-reference. There's no database. It's just interesting how it all comes together.

40:56They're linked in my Google document. I do have all of my past video scripts and Rational Reminder episodes in a Google Drive folder. I will go back and reference them. What was that study that we talked about? And I'll go back. It's not quite a database and it's not very well-structured, but it is there. Are you using AI much to help you to do all this? Off and on, I still find it pretty useless. Some people will probably be so offended to hear that, or they'll think that I'm an idiot for not being able to use it properly, but it makes serious, serious mistakes. It's a little bit useful for finding obscure studies.

41:31It's also useful for finding studies when you don't have keywords, but you have a more abstract idea of a topic that you want to read about or whatever. It's kind of useful for that, but honestly, like using Google Scholar is also pretty good. I do use it quite a bit, but I don't trust it. So this helped you craft a YouTube video script and then you repurpose it effectively here, correct? Most of our podcast episodes like this, where we're like delivering a topic or a video essay or whatever, usually I write that, even if I don't end up making a video on my channel on the topic. I'll write it as if I were going to.

42:10I just find it works well to think about it that way because I have like a target length that works well, both for the podcast and for the YouTube channel and structuring the narrative. I find thinking about it as if I were going to speak it works well. But yeah, typically I'll write it as a video and then we do it as a podcast episode. And do you ever have writer's block or do you ever find yourself, man, I don't have a topic. Like I got to scramble. Hasn't happened yet. It's been eight years or whatever. I don't know. Maybe one day. That would be pretty terrifying. Because it's not like we're recycling all the same topics over and over again.

42:44A lot of the common themes, yes, but it's not like a greatest hits. It just keeps going on repeat. I did a video years ago on individual stocks and I went back and read that script after I'd written most of this one just to see if I had any other ideas in there that I hadn't already covered in this video. And it was actually strikingly similar to that past one. So maybe I am recycling ideas now. Have we talked about your appearance on the Morningstar podcast here? I don't think we have. You and I haven't. I did mention it in one of the episodes with Dan, but that was a while ago. So yeah, I was on Morningstar's The Long View podcast with Christine Benz and Amy Arnott.

43:23It was a good conversation. You should check it out. I found you super chill. almost like you had some sort of, I don't know, relaxant or something. You're so chill and easygoing. You're like, ah, sure. I found some of your answers so refreshingly normal. You had not told me that. It was a good conversation. It was really smooth. I called you the velvet fox or something. You're just so smooth and you seem chilled on the conversation. They were great, but your answers are very straightforward and they're well done, of course. Your answers are great. It was a good conversation. They do a good job.

43:53I've been aware of their podcast forever, but I've binged listens to a few of them. We've got some good episodes. Separate topic, Ben. We've talked about bringing not so much the show, but us hitting the road, doing meetups in various centers. So I put it out there to listeners. If there's advisors out there that might want to meet up in a different city, we're just thinking of getting back to, remember we did some meetups in Montreal and Toronto and Ottawa, which we would do those of course, but perhaps go broader. So if there are people in different cities across the country that might like to help us coordinate something, let us know.

44:24We can do an RR type meetup, or we could also do an advisor meetup. Let's be clear about it. Totally happy to do meetups and meet people that are listeners and stuff like that, but we would love to meet advisors that are potentially interested in joining our firm. That's one of our big objectives. And one of the reasons that we did our deal with OneDigital is to give us the capital to acquire like-minded advisors across Canada that can contribute to what we're building at PWL. So if those people are out there and want to meet up, let us know. And my last question, which might be the most important one, are the premium t-shirts back in stock?

44:58I don't know. I have not asked Angelica or Jackie, but let's check it out in the store here. Sold out. Sold out still. I just know we got a shipment in the office. I didn't know if there's any shirts in there. All sizes are sold out. That's wild. I knew they were going to be hot. I knew it. You were right. I predicted the market on this one. We got pictures of people in them and I know Will, a friend of my, a good friend of my daughter's, loves it. He's also a big fan, so shout out to Will, but loves this shirt. They're cool shirts. They look great, well-made. The contrast with the white and the black, it's such a good nerdy inside joke.

45:32I was talking with a doctor at a medical appointment, not cancer-related, just to check up. Although we did talk about that, obviously. He was like, what do those letters in your shirt mean? Because I was wearing the premium t-shirt. And I was like, it's an asset pricing model. It's a finance thing. I don't know. and he's like, well, no, can you try and explain it to me? So I went through each premium of what it means and he's like, huh, it's really interesting. Look at you, always selling. I have nothing to sell, just talking about asset pricing models. It's a real conversation starter. Which is what everyone should do with their doctor.

46:08Yeah, I guess so. Okay, anything else going on? I know your renovations are progressing well in your front yard, so that's exciting. I'll have to come check it out. progressing is, I don't know if I'd quite use that word. They have progressed. So funny. Okay. Anything else? I don't think so. I don't know if I answered the question about the premium t-shirts, but they are coming back. We have ordered more. They will be restocked. As of the time we're recording this, they have not been restocked, but maybe by the time the episode's released, I don't know. All right. Cool. Well, beautiful June day in Ottawa.

46:40Love the summers. It's a bit humid. I grew up on Vancouver Island, BC, where the summers are also nice, but we don't have the humidity out there. So my travels this past month, I went from Vegas, which is super hot and bone dry. It was 41 degrees one day. Then I went to conference in South Carolina where it's super hot and like 100 % humidity. And now I think we must be close to that here in the auto area. It's humid. I remember the first time I was in Texas and the first time that I was in Vegas, it was just such a different feeling when you walk into the hot air. It's like, whoa. Oh, it just cooks you, but there's no humidity.

47:13You don't sweat from walking around. but man, it's hot. Give them that there. They know how to do hot. All right. Great topic. Great chat. Good to see you. As always. Good to see you. And everybody, thanks for listening. Thanks for listening.

47:45advisory services in the United States of America are offered exclusively by One Digital Investment Advisors, LLC. One Digital and PWL Capital are affiliated entities. However, each company has financial responsibility for only its own products and services. Nothing herein constitutes an offer or solicitation to buy or sell any security. This communication is distributed for informational purposes only. The information contained herein has been derived from sources believed to be accurate, but no guarantee as to its accuracy or completeness can be made. Furthermore, nothing herein should be construed as investment, tax, or legal advice, and or used to make any investment decisions.

48:22Different types of investments and investment strategies have varying degrees of risk and are not suitable for all investors. You should consult with a professional advisor to see how the information contained herein may apply to your individual circumstances. All market indices discussed are unmanaged, do not incur management fees, and cannot be invested indirectly. All investing involves risk of loss and nothing herein should be construed as a guarantee of any specific outcome or profit. Past performance is not indicative of or a guarantee of future results. All statements and opinions presented herein are those of the individual hosts and or guests, are current only as of this communication's original publication date, and are subject to change without notice.

49:00Neither One Digital nor PWL Capital has any obligation to provide revised statements and or opinions in the event of changed circumstances.

49:10Thank you.

From the publisher

What if holding just a few “winning” stocks is riskier than it seems? In this episode, Ben and Cameron explore the hidden dangers of concentrated portfolios and unpack the data that makes a strong case for diversification. Drawing from research by Hendrik Bessembinder, J.P. Morgan, and others, Ben lays out the harsh reality behind individual stock returns: the odds are stacked against long-term success. From skewed return distributions and catastrophic losses to behavioral traps like the endowment effect and familiarity bias, this conversation breaks down why most stock pickers lose—and why diversification remains the only “free lunch” in investing. Whether you're holding onto a single stock for tax reasons, overconfidence, or just inertia, this episode is a must-listen reality check on portfolio risk. They also share thoughts on advisor adoption of indexing, the slow shift in Canada, and how a Rational Reminder YouTube video sparked debate between stock pickers and indexers in the comments section. For anyone navigating concentrated positions—voluntarily or otherwise—this episode is packed with data-driven insight and real-world takeaways.



Key Points From This Episode:

 

(0:00) Welcome to Episode 363: catching up in person and the value of working together in-office.

(1:07) Why advisors are slow to adopt indexing—and how culture, compensation, and inertia play a role.

(2:58) Demand is rising: indexing awareness among young advisors and investors continues to grow.

(4:08) Main topic: The hidden risks of individual stock concentration.

(5:40) The Nortel example: taxes, timing, and the illusion of "free" stock.

(6:51) Individual stocks are far riskier than most people realize—especially recent winners.

(9:09) Most investors hold between 3–7 stocks. Why that’s a problem.

(11:29) Portfolio concentration = fugu prepared by an amateur chef.

(12:45) Diversification reduces risk without reducing expected return.

(14:04) JP Morgan’s “Agony & Ecstasy” report: 44% of stocks suffer catastrophic losses.

(16:26) Why investors overweight the chance of a big win and underweight the risk of losses.

(17:07) The reality of skewed returns: a few big winners, many losers.

(24:35) The 2023 study on concentrated stock positions: recent top performers underperform the most.

(28:40) How many stocks do you need for real diversification? Way more than 20–30.

(32:00) Wealth dispersion and the long-term consequences of concentration.

(35:24) Why even 100-stock portfolios only beat the market 47.5% of the time.

(36:55) Taxes, control, and psychological hurdles make diversifying even harder.

(38:14) Diversification depends on your preference for risk and skewness—but beware the odds.

(39:08) Behind the scenes: Ben’s research process and content development workflow.

(43:14) Ben’s guest appearance on Morningstar’s The Long View.

(44:00) Meetups, t-shirt scarcity, and what’s next for PWL outreach.

 

Links From Today’s Episode:

Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p

Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582.
Rational Reminder Website — https://rationalreminder.ca/ 

Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/

Rational Reminder on X — https://x.com/RationalRemind
Rational Reminder on TikTok — www.tiktok.com/@rationalreminder

Rational Reminder on YouTube — https://www.youtube.com/channel/

Rational Reminder Email — info@rationalreminder.ca
Benjamin Felix — https://pwlcapital.com/our-team/

Benjamin on X — https://x.com/benjaminwfelix

Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/

Cameron Passmore — https://pwlcapital.com/our-team/

Cameron on X — https://x.com/CameronPassmore

Cameron on LinkedIn — https://www.linkedin.com/in/cameronpassmore/`

Episode 346: Hendrik Bessembinder - https://rationalreminder.ca/podcast/346



Papers From Today’s Episode: 

 

‘The Agony & The Ecstasy’ - https://privatebank.jpmorgan.com/nam/en/insights/latest-and-featured/eotm/the-agony-the-ecstasy

‘Why Index Works’ - https://www.top1000funds.com/wp-content/uploads/2017/07/Why-indexing-works.pdf

‘Underperformance of Concentrated Stock Positions’ - https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4541122

‘How Many Stocks Should You Own?’ - https://ndvr.com/journal/how-many-stocks-should-you-own

‘Fund Concentration: A Magnifier of Manager Skill’ - https://discovery.researcher.life/article/fund-concentration-a-magnifier-of-manager-skill/67964b7ccc9d3cae87761f6ef19241a0

 

Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)

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