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204 •   TheIntelligentOptionInvestor
Portfolio Management
There is certainly no way around the tradeoff between OTM and ITM
risk—the rules of leverage are immutable whether in a bullish or a bear -
ish investment—but there are some ways of framing the investment that
will allow intelligent investors to feel more comfortable with making
these types of bearish bets. First, I believe that losses associated with a
bearish position are treated differently within our own minds than those
associated with bullish positions. The reason for this might be the fact
that if you decide to proactively invest in the market, you must buy se-
curities, but you need not sell shares short. The fact that you are losing
when you are engaged in an act that you perceive as unnecessary just
adds to a sense of regret and self-doubt that is necessarily part of the
investing process.
In addition, investors seem to be able to accept underperform-
ing bullish investments in a portfolio context (e.g., “XYZ is losing, but
its only 5 percent of my holdings, and the rest of my portfolio is up, so
its okay”) but look at underperforming bearish investments as if they
were the only investments they held (e.g., “Im losing 5 percent on that
damned short. Why did I ever short that stock in the first place?”). In gen-
eral, people have a hard time looking at investments in a portfolio con-
text (I will discuss this more when I talk about hedging in Chapter 11),
but this problem seems to be orders of magnitude worse in the case of a
bearish position.
My solution to this dilemma—perhaps not the best or most rational
from a performance standpoint but most manageable to me from a psy-
chological one—is to buy OTM puts with much smaller position sizes than
I might for bullish bets with the same conviction level. This means that I
have smaller, more highly levered positions. The reason this works for me
is that once I spend the premium on the put option, I consider the money
gone—a sunk cost—and do not even bother to look at the mark-to-market
value of the option after that unless there is a large drop in the stock price.
Somehow this acknowledgment of a realized loss up front is easier to han-
dle psychologically than watching my ITM put position suffer unrealized
losses of 1.5 times the rise of the stock every day.
This strategy may well be proof that I simply am not a natural-born
short seller, and you are encouraged, now that you understand the issues