Add training workflow, datasets, and runbook
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Risk and the Intelligent Option Investor • 265
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For an intelligent option investor who has a long-term worst-case
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valuation that is now 20 percent higher than the market price, there is a
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wonderful opportunity to sell a put and receive a fat premium (with the
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possibility of owning the stock at an attractive discount to the likely fair
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value), sell a put and use the proceeds to buy an OTM call LEAPS, or sim-
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ply buy the stock to open a position.
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Indeed, this strategy is perfectly in keeping with the dictum, “Be fear-
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ful when others are greedy and greedy when others are fearful. ” This strat-
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egy is also perfectly reasonable but obviously rests on the ability of the
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investor to accurately estimate the actual intrinsic value of a stock. This
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brings us to the next form of risk—valuation risk.
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Valuation Risk
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Although valuation is not a difficult process, it is one that necessarily in-
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cludes unknowable elements. In our own best- and worst-case valuation
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methodology, we have allowed for these unknowns by focusing on plausi-
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ble ranges rather than precise point estimates. Of course, our best- or worst-
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case estimates might be wrong. This could be due to our misunderstanding
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of the economic dynamics of the business in which we have invested or
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may even come about because of the way we originally framed the problem.
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Thinking back to how we defined our ranges, recall that we were focusing
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on one-standard-deviation probabilities—in other words, scenarios that
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might plausibly be expected to materialize two times out of three. Obvi-
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ously, even if we understand the dynamics of the business very well, one
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time out of three, our valuation process will generate a fair value range that
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is, in fact, materially different from the actual intrinsic value of the stock.
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In contrast to market risk, which most often is a nonmaterial and tem-
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porary issue, misestimating the fair value of a stock represents a material
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risk to capital, whether our valuation range is too low or too high. If we esti-
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mate a valuation range that is too low, we are likely to end up not allocating
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enough capital to the investment or using inappropriately light leverage.
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This means that we will have missed the opportunity to generate as much
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return on this investment as we may have. If we estimate a valuation range
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that is too high, we are likely to end up allocating too much capital to the
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