Forget About Good Deals

There a few investors who can buy stocks, or other financial assets, on sale and succeed over the long haul. The winners are household names, the value kings. Warren Buffett and Charlie Munger, Joel Greenblatt, Seth Klarman, David Tepper, and maybe a few others.

Interestingly, many of these famous value investors have actually strayed a bit from their true value roots. Buffett and Munger are now better described as "quality" investors, choosing factors like growing free cash flow, low debt, and profitability over price. This has evolved into the famous line "great companies at fair prices".

On the other hand, Klarman and Tepper run hedge funds using a lot of derivatives and leverage and are noted for being contrarians--a very different strategy from value investing as most amateur investors know it.

Value Investing

While it's certainly extremely difficult, I'm not suggesting that it is impossible to be a profitable value investor. There are clearly people out there who do well in value investing, scouring the markets for deals based on factors like Price/Book, Price/Earnings, Price/Free Cash Flow, and Enterprise Value/EBIT ratios.

The challenge is that you, the amateur investor, must be firmly rational in all your investment decisions in a systematic manner. At the same time, you must believe the entire market is irrational in its pricing of those same investment positions. That takes cojones.

Aside from the contrarian nature of value investing, there is also a massive built-in problem: the "Value Trap". A stock that is falling in price can look like a better and better buy based on value metrics right up to the point where it's essentially worthless. To protect yourself, a successful value investor needs to know exactly when to buy, how much to buy, and, maybe more importantly, when to cut your losses.

Broad-based value investing, in the form of buying the lower valued chunks of broad markets, seems to be failing in many ways. Over the past ten years, traditional, passive value funds have under-performed the whole U.S. stock market by more than 1.3% per year. Over that ten years, that translates to a cumulative investment growth of 136% versus just 106% for value. It's too soon to say if passive value is dead, or if its a temporary blip, or anything else in particular.

Every strategy has periods of out-performance and under-performance, but the widely believed value premium is certainly not a given. Even Jack Bogle, a noted proponent of passive investing, has suggested that historical analysis demonstrating a value premium is flawed. The suggestion is the value premium is actually a case of cherry-picking a good time for value investing, but over long time periods passive value will perform equal to or less than the broad market.

Trend Investing

This is why I choose trend investing instead, using leverage and a range of markets. Although buying something that appears to be on sale appeals to the frugality in me, I would rather buy something that is going up in price. I am content to following the collective rational and irrational players in the markets who slog it out every day determining the price of everything.

If the participants of a liquid market are bidding the price of a particular stock higher and higher, there's something going on under the surface. A company might be producing highly profitable products that are selling faster and faster, a company may have cut costs to increase profitability, maybe there's a takeover coming that hasn't been announced yet.

If the market is bidding down a currency, maybe the country is in economic trouble. Perhaps interest rates in the country are too high and the market is betting that rates will fall. Maybe the country is intentionally devaluing to try boost exports as part of their economic policy.

The same logic applies to interest rates. Interest rates are a great measure of risk and perceived risk. In general, the more financially responsible a borrower is, the better their rates will be. If national debt rates are going down, chances are the country is doing well, the government is going down a more fiscally responsible path, there might be a positive trade balance meaning foreign currency is pouring into the local economy.

On the other hand, if interest rates are going up, lets say on corporate debt, it might be a good signal to sell. Rates on corporate debt often begin to rise when the markets believe a company is getting into some kind of trouble. Maybe they have too much debt on their books, it could be an issue of declining market prospects in that company's sector, sometimes sales and profitability are an issue. Other times the market believes the assets held by the corporation might not be worth as much as the company has stated in the past.

It is difficult and maybe even impossible to decipher the exact reasons why price is going one way or another. However, it's easy to decipher the price itself. The price is published every day, every hour, every minute, every second and it tends to trend.

Where Valuation Comes Into Play

Just because I invest based on the market price and the trends in those prices doesn't mean I believe the price is correct relative to fundamentals. More often than not, I ignore fundamentals. To me, fundamentals and valuation come a distant second to the trend of the price alone.

No matter how cheap an asset is, I will not buy it because it is cheap. The asset only comes into consideration if the price is moving up and has entered an up-trend. I understand that means I don't buy at the cheapest price possible, but that's precisely my goal.

I would rather have the market as a whole identify a bottom and turn around a price than try finding that bottom myself only to miss over and over.

For me, cheapness, or valuation, are only important when cash is limited and I have to decide between two or more investments that are in a price up-trend. In this situation, I will go with the cheaper asset provided other factors are more or less equal.

For example, lets say I have 10% of my portfolio in cash that can be allocated to investments. There are two markets that I am following which have recently entered an uptrend. I can only buy one of those two assets, which one should I choose? Well, this is where valuation comes into play. If Market A is in the 99th percentile of its historical valuation and Market B is at the 60th percentile of its historical valuation, I will choose Market B.

Sure, Market A might go completely crazy and hit the moon. But a reasonable person making disciplined bets would have to agree that Market B has more room to run before the price gets into unprecedented territory. On a balance of probabilities, Market B is the better market to invest in.

Always buy into an up-trend and ignore value unless resources are limited while opportunities are plentiful.

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Everyone is a Speculator

Speculation: the practice of buying assets that incur risk to the speculator with the objective of selling those assets for a profit at a later date.

Arguably every investor is in some way a speculator. Every investor takes on risk to varying degrees in order to make a profit. This includes investors which purport to be buy-and-hold investors. With few exceptions I will touch on later, buy-and-hold investors are simply speculators in denial who theoretically operate on a much longer time-frame.

A buy-and-holder will slowly purchase the same, or similar assets throughout their working lives and then slowly sell those assets--hopefully for a substantial profit--when they are retired. I say theoretically because countless studies show there are few true buy-and-hold investors. When markets collapse, buy-and-hold investors sell in the panic with everyone else. However, nine years into a bull market cycle selling yourself as a buy-and-hold investor is easy and religiously gratifying.

I embrace speculation and I don't believe in buy-and-hold. Things happen in markets which should make every investor think very hard about their investment strategy. The perfect modern example is Japan where their stock market valuation is still just over 50% of the peak value in 1989--nearly three decades later. This issue isn't exclusive to Japanese stocks though; throughout the ages massive shocks have occurred in assets ranging from government debt to productive land to currency.

No asset is truly safe to hold by any individual investor.

Understanding Speculation

Broadly speaking the value of real, productive assets tends to increase over very long periods of time. This includes things like productive farmland, productive timberland, and other assets which generate some form of generated return.

Tangible, non-productive assets tend to hold their real value absent spoilage. This includes gold and silver, quality furniture, or the structure of a well-built, durable building.

However, over shorter time periods these observations do not hold true at all. Sometimes, such as today when ample credit is available, farmland values get very, very expensive relative to their historical value. Other times, as in the 1930s during the Great Depression, farmland could be bought very cheaply as farmers across North America were going broke. That said, despite the gains in crop production and general decline in food prices, the financial return a farmer could generate from their land has been very similar over the ages.

This same logic doesn't apply to other businesses. Successful businesses can earn substantial profits for their shareholders, but they all eventually fail. The ones that gain effective monopolies can last longer than businesses who do not, but competition means all businesses are eventually extinguished. While buying and holding good farmland or timberland forever could be logically plausible, if not a nerve-wracking investment, holding businesses is ridiculous.

Speculation, or at least the embrace of speculation as many perceive it today, is a great way to profit from the price movements in assets over shorter and medium time frames. It's not as much a bet on the asset itself as it is a bet on the prevailing human psychology which is attempting to price that asset at any given time. Speculation is truly a bet on the collective human emotions involved in the market for that asset.

Playing Both Sides of the Market

Since price of any asset can increase or decrease over the shorter-term, it's important to embrace being "long" or "short" the market as a speculator.

There are many ways to speculate in the market and it seems the list of instruments is growing all the time. The standard method is to simply buy an asset directly or indirectly. An example of a direct holding is buying an individual stock, treasury bond, or currency, while indirect holdings can be through ETFs or mutual funds. However, the derivatives market shouldn't be ignored by more advanced speculators. This includes everything from futures to CFDs to options.

Just like buy-and-hold, being a speculator is risky. You can lose all your money, but you can also make a lot of money. Risk control and understanding your asset is of absolute importance! Limit the size of your positions, maintain stop-loss orders on every position to a low level of loss as a percentage of equity, and spread your bets across numerous assets.

To profit from both sides of the market, you must use a system. Trading on gut feelings or fundamentals is not reliable and is likely to result in very poor returns. Betting on price changes means you should use movements in price only to trigger your bets. Moving averages and breakouts are great tools to help you identify price trends. Buy the upside when the trend is up, sell the downside when the trend is down.

Betting on the Upside

It is generally quite easy to buy, or take a "long" position on any major asset (productive or non-productive). You can buy individual stocks, index funds, call options, futures, bonds, and currencies in any brokerage account. The cost is very low, typically a small commission fee plus interest costs if you borrowed any money to execute that asset purchase. Even the interest costs are very low with the better brokerages.

As discussed before, productive assets collectively have a long-term uptrend in real valuation. This is because businesses (as a whole) generate profits, farms produce food, forests produce timber, and dwellings generate rents. As long as the assets remain productive, this won't change. This is the logic behind buy-and-hold investing.

Non-productive assets will also increase in value, but increases are generally limited to inflation and the price of alternatives. There are countless shorter-term impacts which generally revolve around supply capability and product demand.

Betting on the Downside

Taking a "short" position against a productive asset can be much more difficult and risky. It's important to understand how betting against an asset works and what instruments you should choose to bet on price declines. Price volatility tends to increase when prices fall. This means a large price decline can be followed by a sudden, aggressive price increase (called a bear rally).

To short individual stocks or standard ETFs in a traditional manner, you must borrow the security from someone who owns it and pay them an interest fee and the cost of dividends for that privilege. Someone shorting stocks can easily be forced to close their short position at a loss when bear rallies occur. Even experienced players can very easily lose money this way.

It's generally better to bet against productive assets with more advanced instruments such as put options. Longer dated put options can help a speculator with risk-control while providing the potential for outsized returns. The return profile of options are very asymmetric: you can lose 100% of your investment, but you can gain hundreds of percent on your investment.

Futures and CFDs are other great tools to use when betting on price declines. Although the leverage must be controlled (minimum leverage ratios can be astronomically high), the cost of trading on the upside or downside is equal. There is no downside penalty built in these instruments.

You can also use inverse ETFs, but I would stay away from the leveraged ones for the volatility issue. The Canadian market for inverse ETFs is very thin, but there are several good choices on the U.S. stock market.

The least risky method to benefit from a price decline in a certain asset is to sell that asset and hold cash, waiting to purchase it at some later date for a cheaper price. Systematic switching from holding productive assets to holding cash can be very profitable with minimal costs. Dual Momentum is a great example of an asset to cash system.


All investors are speculators because they take risks in anticipation of generating a positive return on their capital. If you want to avoid the large medium-term drawdowns that occur in asset prices, you should embrace the idea of being a true speculator. This means betting both on price increases and price declines.

Our modern financial markets are huge and there is no real limit to speculation choices. Nearly anyone with some extra money can buy or sell anything from stocks to treasury bills, from gold to zinc, from oats to oil, from Chinese yuan to South African rand. You can't possible have a good understanding of fundamentals in such a wide variety of assets, so you must speculate using a price-driven system.

It's easiest to speculate on the "long" side of productive assets. This means betting that assets like businesses (as a collective), farmland, or timberland will increase in value over time while providing positive income during the holding period. Buying non-productive assets can also be very profitable during rising price trends.

Betting on price declines requires special care and attention, so you should consider all your choices across various financial instruments. Depending on the underlying asset you are betting against, the best way to profit could be simply selling the asset and holding cash, buying inverse ETFs, buying long dated put options, selling futures contracts, selling CFDs, or selling currencies.

Always use careful risk control in your account to limit losses on any one asset and your account as a whole. This includes stop-losses on position entries, diversification across non-correlated assets, and careful position sizing.

Comments & Questions

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