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Are you kidding me?

Keep writing naked puts and then compound it by assessing your risk based on historical data.

This is a surefire way of loosing your shirt when the next Lehman level event comes around.

The risk in your strategy is that the stock market has very fat tails and unlikely events happen with more regularity than they should -- and the math that you're using to assess your risk discounts all these events by terming them unlikely.

spelling watchdog says: 'lose' not 'loose'
sure. you've got to watch out for black swans..you should certainly shouldn't plan your portfolio around such a thing. You may as well put your money in CDs.
Only apply the theory to stocks you'd like to own.

I acknowledge the strategy isn't risk free (no strategy is), but if you're going to buy a stock, considering using this strategy instead.