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1988issue C121-5

Two-sided cheap premium, volatility, and protective puts

The archive records a written philosophy that funds a small speculative sleeve, buys cheap near-the-money underpriced contracts with ample time left, and purchases both calls and puts on a monthly cadence. Editorial reading: treat that book as a market-regime sleeve, mark cheapness only after a volatility-band haircut, and keep protective-put-insurance as the stock book's explicit loss bound.

  • Mark a contract as a cheap-underpriced-option only after a volatility-band haircut, not because the listed premium looks small.
  • Two-sided-selection buys the same count of puts and calls so the monthly sleeve is not a forecast of market direction.
  • Option positions can lose as often as they win, so the written plan funds only a small crash-pool-sleeve that can be fully risked without disturbing the rest of the book.
  • Protective-put-insurance is taught as a bound on stock-book losses in a sharp drop, separate from the speculative sleeve.
Entries in this reading3 entries

A monthly sleeve, not a lottery ticket

A familiar retail path is to buy a stock or index option on a pending-event tip or a leverage-for-speed pitch, then either lose the stake or recycle a lucky payoff into a larger later loss.

Durable participation is framed as keeping a written plan through winning and losing streaks, in contrast to a one-off put bought days before a crash.

Editorial reading: treat a cheap option as a monthly market-regime sleeve rather than a hot-tip lottery ticket. The archive workflow marks cheapness only after a volatility-band haircut, keeps a matched put-and-call count, and holds a protective put as the stock book's explicit loss bound.

Mark cheapness after a volatility-band haircut

One documented selection rule bought contracts that were both low-priced and below modeled value. A cheap-underpriced-option is a contract whose market premium sits below a modeled fair value after the underlying's volatility-band is applied.

Fair-value tables assume average stock volatility of 23 to 39 percent. A volatility-band is a three-way stock-range class, low, average, or high, used to raise or lower table fair value before a premium is called cheap.

Range-ratio-volatility is a high-minus-low price range divided by the midpoint, then used to scale the table's average-volatility price. That range ratio raises table prices at 40 percent-plus volatility and lowers them at 5 to 22 percent.

A future-value-schedule, built from simulated paths over thousands of stock-years, estimates later option worth, an average high, and the chance of reaching that high before expiration.

Neutralize direction with two-sided-selection

The same documented rule kept the same number of puts and calls so the book was not a directional forecast. That two-sided-selection is the point of the monthly sleeve: it is not a call on which way the market will move.

The written philosophy funds only a small speculative sleeve, buys cheap near-the-money underpriced contracts with ample time left, purchases both calls and puts on a monthly cadence, and rehearses on paper before committing cash. That small, pre-committed allocation is the crash-pool-sleeve: it can be fully risked without disturbing the rest of the book.

A stated mechanical lesson is that option positions can lose as often as they win, so a book depends on occasional large payoffs offsetting many small losses.

A theoretical at-the-money call book held in six-month windows from 1963 through 1975 was described as about seven times more variable than a comparable stock book and, at one point, 90 percent below its starting value. Editorial reading: that variability is why the sleeve stays small and why a written plan is kept through winning and losing streaks.

Keep a protective put as the stock book's loss bound

Puts are taught as insurance on a stock portfolio, used to bound losses in sharp market drops, alongside discount buying and same-expiry vertical spreads.

Protective-put-insurance is a put held against stock exposure to bound losses during a sharp market drop. Editorial reading: keep that insurance on the stock book as an explicit loss bound, and do not confuse it with the two-sided crash-pool-sleeve.

Educational research material, not investment advice. Historical source context does not establish present-day performance.
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20001-4 pp.Next on Protective putCompare a Protective put and a Stop-loss order before entryAfter a long or short is filled, a Stop-loss order sits at a swing extreme, a recent high or low, or the lowest low or highest high of a chosen lookback so a wrong read can force an exit.
All readings on this track · 15 readings
  1. 1988Two-sided cheap premium, volatility, and protective puts
  2. 2000Compare a Protective put and a Stop-loss order before entry
  3. 2007Sizing options by assignment, spread legs, and portfolio margin
  4. 2007Fund a put-hedged long by remaining package loss
  5. 2008Protective put sizing under broker insolvency
  6. 2008Seasonal regimes, index put overlays, and call-spread mechanics
  7. 2008Stops, protective puts, and financed spread risk
  8. 2008Three loss bounds: debit spreads, stops, and protective puts
  9. 2014Seasonal put spreads for index-linked portfolios
  10. 2017Option construction after a post-listing drawdown
  11. 2017A stop-loss is an execution request, not a loss ceiling
  12. 2018Objective-first construction of hedges and income
  13. 2018A protective put as a prepaid loss budget
  14. 2020When a futures gap-open voids stop-loss protection
  15. 2020Protective put loss budget by strike and tenor
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