Fat Tail

Howard Marks' Book: Chapter 18


Continuation of portfolio management highlights from Howard Marks’ book, The Most Important Thing: Uncommon Sense for the Thoughtful Investor, Chapter 18 “The Most Important Thing Is…Avoiding Pitfalls” Risk, Volatility

“…trying to avoid losses is more important than striving or great investment successes. The latter can be achieved some of the time, but the occasional failures may be crippling. The former can be done more often and more dependably…and with consequences when it fails that are more tolerable…A portfolio that contains too little risk can make you underperform in a bull market, but no one ever went bust from that; there are far worse fates.

“You could require your portfolio to do well in a rerun of 2008, but then you’d hold only Treasurys, cash and gold. Is that a viable strategy? Probably not. So the general rule is that it’s important to avoid pitfalls, but there must be a limit. And the limit is different for each investor.”

Volatility, Psychology, Trackrecord, When To Buy, When To Sell, Clients

“…almost nothing performed well in the meltdown of 2008…While it was nigh onto impossible to avoid declines completely, relative outperformance in the form of smaller losses was enough to let you do better in the decline and take grater advantage of the rebound.”

“In periods that are relatively loss free, people tend to think of risk as volatility and become convinced they can live with it. If that were true, they would experience markdowns, invest more at the lows and go on to enjoy the recovery, coming out ahead in the long run. But if the ability to live with volatility and maintain one’s composure has been overestimated—and usually it has—that error tends to come to light when the market is a its nadir. Loss of confidence and resolve can cause investors to sell at the bottom, converting downward fluctuations into permanent losses and preventing them from participating fully in the subsequent recovery. This is the great error in investing—the most unfortunate aspect of pro-cyclical behavior—because of its permanence and because it tends to affect large portions of portfolios.”

“While it’s true that you can’t spend relative outperformance, human nature causes defensive investors and their less traumatized clients to derive comfort in down markets when they lose less than others. This has two very important effects. First, it enables them to maintain their equanimity and resist the psychological pressures that often make people sell at lows. Second, being in a better frame of mind and better financial condition, they are more able to profit from the carnage by buying at lows. Thus, they generally do better in recoveries.”

Volatility is not the true risk; the true risk lies in what investors do / how they behave during volatile periods.

Mistakes, Creativity, Psychology

“One type of analytical error…is what I call ‘failure of imagination’…being unable to conceive of the full range of possible outcomes or not fully understanding the consequences of the more extreme occurrences.”

“Another important pitfall…is the failure to recognize market cycles and manias and move in the opposite direction. Extremes in cycles and trends don’t occur often, and thus they’re not a frequent source of error, but they give rise to the largest errors.”

“…when the future stops being like the past, extrapolation fails and large amounts of money are either lost or not made…the success of your investment actions shouldn’t be highly dependent on normal outcomes prevailing; instead, you must allow for outliers…"

“…the third form of error doesn’t consist of doing the wrong thing, but rather of failing to do the right thing. Average investors are fortunate if they can avoid pitfalls, whereas superior investors look to take advantage of them…a different kind of mistake, an error of omission, but probably one most investors would be willing to live with.”

“The essential first step in avoiding pitfalls consists of being on the lookout for them…learning about pitfalls through painful experience is of only limited help. The key is to try to anticipate them…The markets are a classroom where lesson are taught every day. The keys to investment success lie in observing and learning.”

“The fascinating and challenging thing is that the error moves around. Sometimes prices are too high and sometimes they’re too low. Sometimes the divergence of prices from value affects individual securities or assets and sometimes whole markets – sometimes one market and sometimes another. Sometimes the error lies in doing something and sometimes in not doing it, sometimes in being bullish and sometimes in being bearish…avoiding pitfalls and identifying and acting on error aren’t susceptible to rules, algorithms, or roadmaps. What I would urge is awareness, flexibility, adaptability and a mind-set that is focused on taking cues from the environment.”

Correlation, Diversification, Risk

“There’s another important aspect of failure of imagination. Everyone knows assets have prospective returns and risks, and they’re possible to guess at. But few people understand asset correlation: how one asset will react to a change in another, or that two assets will react similarly to a change in a third. Understanding and anticipating the power of correlation – and thus the limitations of diversification – is a principal aspect of risk control and portfolio management, but it’s very hard to accomplish…Investors often fail to appreciate the common threads that run through portfolios.”

“Hidden fault lines running through portfolios can make the prices of seemingly unrelated assets move in tandem. It’s easier to assess the return and risk of an investment than to understand how it will move relative to others. Correlation is often underestimated, especially because of the degree to which it increases in crisis. A portfolio may appear to be diversified as to asset class, industry and geography, but in tough times, non-fundamental factors such as margin calls, frozen markets and a general risk in risk aversion can become dominant, affecting everything similarly.”

Hedging, Expected Return, Opportunity Cost, Fat Tail

“…a dilemma we have to navigate. How much time and capital should an investor devote to protecting against the improbable disaster? We can insure against every extreme outcome…But doing so will be costly, and the cost will detract form investment returns when that protection turns out not to have been needed…and that’ll be most of the time.”


Montier on Exposures & Bubbles


Below are some wonderful bits on bubbles and portfolio construction from James Montier. Excerpts were extracted from a Feb 2014 interview with Montier by Robert Huebscher of Advisor Perspectives – a worthwhile read. Cash, Expected Returns, Exposure

“The issue is…everything is expensive right now. How do you build a portfolio that recognizes the fact that cash is generating negative returns…you have to recognize that this is the purgatory of low returns. This is the environment within which we operate. As much as we wish it could be different, the reality is it isn’t, so you have to build a portfolio up that tries to make sense. That means owning some equities where you think you’re getting at least some degree of reasonable compensation for owning them, and then basically trying to create a perfect dry-powder asset.

The perfect dry-powder asset would have three characteristics: it would give you liquidity, protect you against inflation and it might generate a little bit of return.

Right now, of course, there is nothing that generates all three of those characteristics. So you have to try and build one in a synthetic fashion, which means holding some cash for its liquidity benefits. It means owning something like TIPS, which are priced considerably more attractively than cash, to generate inflation protection. Then, you must think about the areas to add a little bit of value to generate an above-cash return: selected forms of credit or possibly equity-spread trades, but nothing too risky.”

Dry powder is generally associated with cash. But as Montier describes here, it is possible that in certain scenarios cash is not the optimal dry-powder asset.

His description of creating a perfect dry-powder asset is akin to creating synthetic exposures, something usually reserved for large hedge funds / institutions and their counterparties.

Interestingly, anyone can (try to) create synthetic exposures by isolating characteristics of certain assets / securities to build a desired combination that behaves a certain way in XYZ environment, or if ABC happens.

For more on isolating and creating exposures, see our previous article on this topic

Hedging, Fat Tail

“Bubble hunting can be overrated…I’m not sure it’s particularly helpful, in many regards…

Let’s take an equity‐market bubble, like the technology‐media‐telecom (TMT) bubble. Everyone now agrees I think, except maybe two academics, that TMT was actually a bubble. To some extent it didn’t really matter, because you had a valuation that was so extraordinarily high. You didn’t actually have to believe it was a bubble. You just knew you were going to get incredibly low returns from the fact that you were just massively overpaying for those assets.

Knowing it was a bubble as such helped reassure those of us who were arguing that it was a bubble, though we could see the more common signs of mania like massive issuance, IPOs and shifting valuation metrics that eventually were off the income statement altogether.

All of those things are good confirming evidence, but ultimately it didn’t matter because the valuation alone was enough to persuade you to think, ‘Hey, I’m just not going to get any returns in these assets even if it isn’t a bubble.’

Bubblehunting is much more useful when it is with respect to things like credit conditions and the kind of environments we saw in 2007, when it was far less obvious from valuation alone. Valuation was extended, but wasn’t anywhere near the kinds of levels that we saw in 2000. It was extended, but not cripplingly so by 2000 standards. But the ability to actually think about the credit bubble or the potential for a bubble in fundamentals or financial earnings is very useful.

The use of bubble methodology is certainly not to be underestimated, but people can get a little too hung up on it and start to see bubbles everywhere. You hear things about bond bubbles. Do I really care? All I need to know is bonds are going to give me a low return from here. Ultimately, for a buy-and-hold investor, the redemption yield minus expected inflation gives me my total return for bonds. There can’t be anything else in there.

You get the conclusion that, ‘Hey, I don’t really care if it’s a bubble or not.’ I suspect bubble hunting can be useful in some regards. But people use the term too loosely and it can lead to unhelpful assessments.

Expected Return, Capital Preservation

“You can imagine two polar extreme outcomes: Central banks could end financial repression tomorrow. You would get realrate normalization and the only asset that survives unscathed is cash. Bonds suffer, equities suffer and pretty much everything else suffers. Or, the central banks keep their rates incredibly low for a very, very long period.

The portfolios you want to hold under those two different outcomes are extremely different. I have never yet met anyone with a crystal ball who can tell me which of these two outcomes is most likely – or even which one could actually happen. You’re left trying to build a portfolio that will survive both outcomes. It won’t do best under either one of the two outcomes or the most probable outcome, but it will survive. That really is the preeminent occupation of my mind at the moment.”

When To Buy, When To Sell, Psychology

“One of curses of value managers is we’re always too early both to buy and to sell. One of the ways that were trying to deal with that is to deliberately slow our behavior down, so we try to react at least to a moving average of the forecast rather than the spot forecasts.”


Mauboussin on Position Sizing


Below are excerpts from an article written by Michael Mauboussin in 2006 on the importance of position sizing (Size Matters). For fans of the Kelly formula, this is a must-read. Mauboussin highlights a few very important flaws of the Kelly formula when applied to our imperfect, non-normally distributed world of investing. Sizing, Diversification

“To suppose that safety-first consists in having a small gamble in a large number of different [companies] where I have no information to reach a good judgment, as compared with a substantial stake in a company where one’s information is adequate, strikes me as a travesty of investment policy. -- John Maynard Keynes, Letter to F.C. Scott, February 6, 1942”

“As an investor, maximizing wealth over time requires you to do two things: find situations where you have an analytical edge; and allocate the appropriate amount of capital when you do have an edge. While Wall Street dedicates a substantial percentage of time and effort trying to gain an edge, very few portfolio managers understand how to size their positions to maximize long-term wealth.”

“Position size is extremely important in determining equity portfolio returns. Two portfolio managers with the same list and number of stocks can generate meaningfully different results based on how they allocate the capital among the stocks. Great investors don’t stop with finding attractive investment opportunities; they know how to take maximum advantage of the opportunities. As Charlie Munger says, good investing combines patience and aggressive opportunism.”

This is consistent with my belief that investors can differentiate himself/herself from the pack by going beyond security selection, and applying superior portfolio management tactics.

Sizing, Expected Return, Fat Tails, Compounding, Correlation

“We can express the Kelly formula a number of ways. We’ll follow Poundstone’s exposition: Edge / Odds = F

Here, edge is the expected value of the financial proposition, odds reflect the market’s expectation for how much you win if you win, and F represents the percentage of your bankroll you should bet. Note that in an efficient market, there is no edge because the odds accurately represent the probabilities of success. Hence, bets based on the market’s information have zero expected value (this before the costs associated with betting) and an F of zero…if there is a probability of loss, even with a positive expected value economic proposition, betting too much reduces your expected wealth.”

"Though basic, this illustration draws out two crucial points for investors of all stripes: • An intelligent investor needs an edge (a view different than that of the market); and • An investor needs to properly allocate capital to maximize value when an investment idea does appear."

“In the stock market an investor faces many more outcomes than a gambler in a casino…Know the distribution. Long-term stock market investing differs from casino games, or even trading, because outcomes vary much more than a simple model suggests. Any practical money management system faces the challenge of correcting for more complicated real-world distributions. Substantial empirical evidence shows that stock price changes do not fall along a normal distribution. Actual distributions contain many more small change observations and many more large moves than the simple distribution predicts. These tails play a meaningful role in shaping total returns for assets, and can be a cause of substantial financial pain for investors who do not anticipate them.”

“…the central message for investors is that standard mean/variance analysis does not deal with the compounding of investments. If you seek to compound your wealth, then maximizing geometric returns should be front and center in your thinking…For a geometric mean maximization system to work, an investor has to participate in the markets over the long term. In addition, the portfolio manager must be able to systematically identify investment edges—points of view different than that of the market and with higher expected returns. Finally, since by definition not all market participants can have an edge, not all investors can use a Kelly system. In fact, most financial economists believe markets to be efficient. For them, a discussion of optimal betting strategy is moot because no one can systematically gain edges.”

Notice in order for the Kelly Formula to work effectively, the devil (as usual) lies in the details. Get the odds wrong, or get the edge wrong, the sizing allocation will be wrong, which can reduce your expected wealth.

Another question that I’ve been pondered is how the Kelly formula/criterion accounts for correlation between bets. Unlike casino gambling, probability outcomes in investing are often not independent events.

Psychology, Volatility

“The higher the percentage of your bankroll you bet (f from the Kelly formula) the larger your drawdowns.

Another important lesson from prospect theory—and a departure from standard utility theory—is individuals are loss averse. Specifically, people regret losses roughly two to two and a half times more than similar-sized gains. Naturally, the longer the holding period in the stock market the higher the probability of a positive return because stocks, in aggregate, have a positive expected value. Loss aversion can lead investors to suboptimal decisions, including the well-documented disposition effect.

Investors checking their portfolios frequently, especially volatile portfolios, are likely to suffer from myopic loss aversion. The key point is that a Kelly system, which requires a long-term perspective to be effective, is inherently very difficult for investors to deal with psychologically.”

“Applying the Kelly Criterion is hard psychologically. Assuming you do have an investment edge and a long-term horizon, applying the Kelly system is still hard because of loss aversion. Most investors face institutional and psychological constraints in applying a Kelly-type system.”


Wisdom from Peter Lynch


Previously, we summarized an interview with Michael F. Price & an interview with David E. Shaw from Peter J. Tanous’ book Investment Gurus. Below are highlight from yet another fantastic interview, this time with Peter Lynch, the legendary investor who ran Fidelity's Magellan Fund from 1977-1990, compounding at ~30% annually during that period.

When To Buy, Volatility, Catalyst

On technical buy indicators, expected volatility, and catalysts:

“I have traditionally liked a certain formation. It’s what I call the electrocardiogram of a rock. The goes from, say, 50 to 8. It has an incredible crater. Then it goes sideways for a few years between 8 and 11. That’s why I call it the EKG of a rock. It’s never changing. Now you know if something goes right with this company, the stock is going north. In reality, it’s probably just going to go sideways forever. So if you’re right it goes north and if you’re wrong it goes sideways. These stocks make for a nice research list…stocks that have bottomed out...

...When it’s going from 50 to 8, it looks cheap at 15; it looks cheap at 12. So you want the knife to stick in the wood. When it stops vibrating, then you can pick it up. That’s how I see it on a purely technical basis…why the stock is on your research list, not on your buy list. You investigate and you find that of these ten stories, this one has something going on. They’re getting rid of a losing division, one of their competitors is going under, or something else.”

When To Buy

“You could have bought Wal-Mart ten years after it went public…it was a twenty-year-old company. This was not a startup…You could have bought Wal-Mart and made 30 times your money. If you bought it the day it went public you would have made 500 times your money. But you could have made 30 times your money ten years after it went public.”

Many value investors experience difficulty buying assets when prices are moving upward. At those moments, perhaps it’s important to remember to see the forest (ultimate risk-reward) through the trees (an upward moving price).

Expected Return, Fat Tail

“There may be only a few times a decade when you make a lot of money. How many times in your lifetime are you going to make five times on your money?”

I hear chatter about “lotto ticket” and “asymmetric risk-reward” ideas all the time. A friend recently joked that he would rather buy actual lotto tickets than the lotto-ticket-ideas because with the former he actually stands a chance of hitting the jackpot.

Apparently, Peter Lynch sort of agrees with my friend. Markets are generally efficient enough that asymmetric risk-reward opportunities rarely occur. The tricky part is discerning between the real deal vs. imitations conjured from misjudgment or wishful thinking analysis.

Diversification, Correlation

“If you buy ten emerging growth funds and all these companies have small sales and are very volatile companies, buying ten of those is not diversification.”

The correlation between assets, not the number of assets, ultimately determines the level of diversification within a portfolio.


“One out of every hundred Americans was in my fund…For many of these people, $5,000 is half their assets other than their house. And there are people you meet who say we sent our kids to college, or we paid off the mortgage. What I’m saying is that it’s very rewarding to have a fund where you really made a difference in a lot of people’s lives.”

How refreshing. Those who work in the investment management world sometimes forget for whom they toil (beyond numero uno). A job well done could potentially make large positive impacts on the lives of others.

Team Management

On how he’s spending his time after stepping down from managing the Magellan Fund:

“…I work with young analysts. We bring in six new ones a year and I work with them one-on-one.”

Process Over Outcome

On whether Peter Lynch would have pursued an investment career had he lost money in his first stock purchase:

“Well, I guess if I’d lost money over and over again then maybe I would have gone into another field.”

Only in the long-run is outcome indicative of skill.


“…I was always upset by the fact that they called Magellan a growth fund. I think that is a mistake. If you pigeonhole somebody and all they can buy are the best available growth companies, what happens if all the grow companies are overpriced? You end up buying the least overpriced ones.”



36South: Profiting from the Tails


Many have read about Cornwall Capital (I wrote about them awhile back), a firm that successfully profited from shorting subprime CDS. Those who enjoyed the Cornwall Capital piece are in for a treat. Below are highlights extracted from an Eurekahedge interview with Richard Hollington of 36South, a hedge fund that also specializes in profiting from volatility and tail risk. This piece is a little longer than our usual articles. There is a lot of good commentary below on how to source, execute, size, and manage portfolio hedges. However, reading this article does not a hedging expert make. In other words, I don’t recommend trying this at home.

Hedging, Derivatives, Fat Tail, Barbell, Sizing, Expected Return, Volatility

“The underlying philosophy is that markets are rational most of the time but 5% of the time rationality gets thrown out of the window, whether because people have made money too easily and become complacent or have lost money too quickly and are so distressed that they are off-loading assets below their intrinsic worth. The emphasis of this approach is market psychology. We search for fear, greed, hysteria and mania. We sell into a bubble about to burst and buy into a post-crash recovery. Bubbles as we know, can take time to play themselves out over an extended period of time and their turning points are normally associated with high volatility. This makes the method of investing in an opportunity critical. Normally it is better to wait until the bubble is bursting as the markets tend to go a lot higher or lower than one thinks. The downside to this is that the move might be over in a short period of time.”

“Our investment methodology is to BUY ONLY long dated “out-of-the-money” options. This methodology has some excellent features…these options can return multiples of the original investment. We look for options that have the potential to return between 5 and 10 times the original investment. Because of their high reward characteristics, only 10-20% of the fund need be invested in these options to achieve our target returns of 15-25%. Our worst case loss is thus known, being the amount invested in options…Our rationale here is that one can never get killed jumping out of a basement window!”

“We zero in on…situations by using our in-house developed ‘Quadrivium’ Methodology. Quadrivium literally means where four rivers meet and a strategy which conforms to criteria required in each of the four circles in our approach will be selected to form a portion of our risk portfolio. The four criteria are used in conjunction with each other in order to ‘ensure that one reality respects all other realities’ as Charlie Munger put it so well. These criteria are:

  • Volatility has already been covered. We ensure the option (using volatility as a proxy) is cheap enough to provide the leverage we require for the level of risk.
  • The next criterion is to look at the technical picture of the market to seek confirmation that there is potential for market movement to the extent and in the direction that we require to attain a multiple return on the option price.
  • The next criterion is fundamentals in that market/asset/option to corroborate our view. We have developed a framework of economic indicators that we monitor in each of the markets we have selected to trade. We are specifically looking for flaws in the structure of markets which are caused by government policy and supply demand imbalances.
  • The next step in the process is based on the sentiment prevailing in the market that we wish to trade. Sentiment often becomes deeply entrenched at market tops and bottoms to the extent that supporters of the status quo can become aggressive in defense of their beliefs. In order to gauge the prevailing sentiment in the market we use Internet searches for key words and couple this with feedback obtained from diverse media coverage. These media opinions can reflect ‘irrational exuberance’ or deep-seated pessimism on a particular stock, index, commodity or currency. These quotations from seasoned professionals in the financial markets encapsulate the essence of this driver of our trading philosophy.”

“Since we know exactly what the current option portfolio is worth we can safely say that this is the absolute worst-case meltdown in the fund based on market risk. This would be an extremely unlikely scenario because long dated options always have some time value and it would mean all positions have moved against us in all asset markets and volatilities have collapsed at the same time. We manage each option on a stop-loss methodology. The stop-loss is based on the number of times the initial option premium multiplies. The first stop is instituted when the option premium has increased three fold. At this level a 60% stop on the option price is registered. As it moves to four times, the stop is tightened to 50% and so on until a maximum of eight times when the stop will be 10%. At this point in time the option has earned the right to discretionary stop-loss status as long as it does not hit the 10% in place. A profit target is then calculated which is based on a three standard deviation move above the 200-day moving average. We will also sell options which have only a year to run if they have not achieved the minimum 3-fold increase and are still worth something.”



Howard Marks' Book: Chapter 7


Continuation of portfolio management highlights from Howard Marks’ book, The Most Important Thing: Uncommon Sense for the Thoughtful Investor, Chapter 7 “The Most Important Thing Is…Recognizing Risk” Risk, Capital Preservation, Compounding

“…Warren Buffett, Peter Lynch, Bill Miller and Julian Robertson. In general their records are remarkable because of their decades of consistency and absence of disasters, not just their high returns.”

“How do you enjoy the full gain in up markets while simultaneously being positioned to achieve superior performance in down markets? By capturing the up-market gain while bearing below-market risk…no mean feat.”

“The road to long-term investment success runs through risk control more than through aggressiveness. Over a full career, most investors’ results will be determined more by how many losers they have, and how bad they are, than by the greatness of their winners.”

The resilient yet participatory portfolio (this term was stolen from a very smart man named Ted Lucas at Lattice Strategies in San Francisco) – a rare creature not easily found. We know it exists because a legendary few, such as those listed above, have found it before. How to find it for ourselves remains the ever perplexing question.

Our regular Readers know that we’re obsessed with the complementary relationship between capital preservation and compounding. For more on this, be sure to check out commentary from Stanley Druckenmiller and Warren Buffett – yes, two very different investors.

Conservatism, Hedging

“Since usually there are more good years in the markets than bad years, and since it takes bad years for the value of risk control to become evident in reduced losses, the cost of risk control – in the form of return foregone – can seem excessive. In good years in the market, risk-conscious investors must content themselves with the knowledge that they benefited from its presence in the portfolio, even though it wasn’t needed…the fruits…come only in the form of losses that don’t happen.”

People talk a lot about mitigating risk in the form of hedging. But what about remaining conservatively positioned (such as having more cash) and incurring the cost of lower portfolio returns? Isn’t the “return foregone” in this case akin to hedging premium?

Conservatism, Fat Tail

“It’s easy to say that they should have made more conservative assumptions. But how conservative? You can’t run a business on the basis of worst-case assumptions. You won’t be able to do anything. And anyway, a ‘worst-case assumption’ is really a misnomer; there’s no such thing, short of a total loss…once you grant that such a decline can happen – for the first time – what extent should you prepare for? Two percent? Ten? Fifty?”

“Even if we realize that unusual, unlikely things can happen, in order to act we make reasoned decisions and knowingly accept that risk when well paid to do so. Once in a while, a ‘black swan’ will materialize. But if in the future we always said, ‘We can’t do such-and-such, because the outcome could be worse than we’ve ever seen before,” we’d be frozen in inaction.

So in most things, you can’t prepare for the worst case. It should suffice to be prepared for once-in-a-generation events. But a generation isn’t forever, and there will be times when that standard is exceeded. What do you do about that? I’ve mused in the past about how much one should devote to preparing for the unlikely disaster. Among other things, the events of 2007-2008 prove there’s no easy answer.”

Risk, Making Mistakes, Process Over Outcome

“High absolute return is much more recognizable and titillating than superior risk-adjusted performance. That’s why it’s high-returning investors who get their pictures in the papers. Since it’s hard to gauge risk and risk-adjusted performance (even after the fact), and since the importance of managing risk is widely underappreciated, investors rarely gain recognition for having done a great job in this regard. That’s especially true in good times.”

“Risk – the possibility of loss – is not observable. What is observable is loss, and generally happens only when risk collides with negative events…loss is what happens when risk meets adversity. Risk is the potential for loss if things go wrong. As long as things go well, loss does not arise. Risk gives rise to loss only when negative events occur in the environment.”

“…the absence of loss does not necessarily mean the portfolio was safely constructed…A good builder is able to avoid construction flaws, while a poor builder incorporates construction flaws. When there are no earthquakes, you can’t tell the difference…That’s what’s behind Warren Buffett’s observation that other than when the tide goes out, we can’t tell which swimmers are clothed and which are naked.”

Good risk management = implementing prevention measures.

Once planted, the seeds of risk can remain dormant for years. Whether or not they sprout into loss depends on the environment and its conditions.

In other words, mistakes that result in losses are often made long before losses occur. Although loss was not the ultimate outcome does not mean mistakes were not made.


Howard Marks' Book: Chapter 5 - Part 4


I'm finally back from vacation. In light of recent market volatility and "risk," let's kick off with a continuation of portfolio management highlights from Howard Marks’ book, The Most Important Thing: Uncommon Sense for the Thoughtful Investor, Chapter 5 “The Most Important Thing Is…Understanding Risk” Risk, Intrinsic Value

“…risk of loss does not necessarily stem from weak fundamentals. A fundamentally weak asset – a less-than-stellar company’s stock, a speculative-grade bond or a building in the wrong part of town – can make for a very successful investment if bought at a low-enough price.”

“Theory says high return is associated with high risk because the former exists to compensate for the latter. But pragmatic value investors feel just the opposite: they believe high return and low risk can be achieved simultaneously by buying things for less than they’re worth. In the same way, overpaying implies both low return and high risk.”

There exists an unbreakable relationship between the purchase price (relative to the intrinsic value) of an investment, and the inherent risk of that investment. In other words, a portion of the risk of any asset is price dependent.



Howard Marks highlights a few other types of risk, beyond is usual loss of capital, etc. Investment risk can take on many other forms – personal and subjective – varying from person, mandate, and circumstance.

“Falling short of one’s goal – …a retired executive may need 4 percent…But for a pension fund that has to average 8% per year, a prolonged period returning 6 percent would entail serious risk. Obviously this risk is personal and subjective, as opposed to absolute and objective…Thus this cannot be the risk for which ‘the market’ demands compensation in the form of higher prospective returns.”

“Underperformance – …since no approach will work all the time – the best investors can have some of the greatest periods of underperformance. Specifically, in crazy times, disciplined investors willingly accept the risk of not taking enough risk to keep up. (See Warren Buffett and Julian Robertson in 1999.)”

“Career Risk – …the extreme form of underperformance risk…risk that could jeopardize return to an agent’s firing point…”

“Unconventionality – …the risk of being different. Stewards of other people’s money can be more comfortable turning in average performance, regardless of where it stands in absolute terms, than with the possibility that unconventional actions will prove unsuccessful and get them fired.”

“Illiquidity – …being unable when needed to turn an investment into cash at a reasonable price.”

Theory suggests that asset returns compensate for higher “risk.” If this is true, how then do assets compensate for subjective risks that vary from person to person, such as falling short of one’s return goal, or career risk stemming from unconventionality?

This highlights the necessity for portfolio managers to identify and segment risks – objective or subjective & quantitative or qualitative – before implementing risk management or hedging strategies.


Risk, Fat Tail

“‘There’s a big difference between probability and outcome. Probable things fail to happen – and improbable things happen – all the time.’ That’s one of the most important things you can know about investment risk.”

“The fact that an investment is susceptible to a particularly serious risk that will occur infrequently if at all – what I call the improbable disaster – means it can seem safer than it really is.”

“…people often use the terms bell-shaped and normal interchangeably, and they’re not the same…the normal distribution assumes events in the distant tails will happen extremely infrequently, while the distribution of financial developments – shaped by humans, with tendency to go to emotion-driven extremes of behavior – should probably be seen as having ‘fatter’ tails…Now that investing has become so reliant on higher math, we have to be on the lookout for occasions when people wrongly apply simplifying assumptions to a complex world.” 

A Page From Cornwall Capital's Playbook


In his book The Big Short, Michael Lewis chronicles how Cornwall correctly predicted and benefited from the subprime housing crisis, via a "Fat Tail." While reading the book, I remember thinking that the approach was different from many other funds that I've encountered. Some tidbits that particularly resonated were the following:

Fat Tail ≠ Probability of Positive Outcome is High

Fat Tail actually implies:

  • Low Probability of Positive Outcome, but…
  • Positive Outcome is more probable than market expectations (therefore the ratio of expected return relative to cost is asymmetric and attractive)

Upon further reflection, I wondered if Cornwall’s approach could be beneficial to more traditional investors, such as:

  • Being creative and looking for other non-traditional securities through which to express certain views and convictions
  • Spending more time to understand how certain securities, options, hedges, or derivative structures are priced by the market and sellers – thus understanding the counterparty’s motivation and rationale (remember, it’s a zero-sum game)
  • Paying closer attention to the ratio of Expected Return vs. Cost (both actual and opportunity)
  • Effectively utilizing and sizing Fat Tails (instances where the probability of occurrence is low, but the ratio of Expected Return to Cost is asymmetrically high) in a portfolio context

Above all, investors should remember that Fat Tails are usually rare occurrences because it involves not only the formation of a view/conviction, but also the identification of an attractively priced security (with asymmetrically high reward relative to cost) to express that view/conviction. Post the subprime crisis, there have been no shortage of views and convictions (hyperinflation, European CDS, etc.), but few securities priced to offer the type of asymmetric reward required to achieve "Fat Tail" status.