A naked put selling focused options trading strategy explained

Selling puts naked is a money making machine. You make money on most trades due to the positive theta and life is good. However, sometimes you bet wrong and you lose big. Winning in this game means we have to avoid the big losses while preserving the opportunity to profit. That requires risk management.

First, I want to say that I have no official system for this. No quantitative models, no portfolio insurances, nada. Just some gut feel. This is just my system. You could have a completely different system, and that would be fine. However, let me point out a couple pros and cons about this system.

Pro: Quantitative models and portfolio insurance give you a false sense of security. Equity issues are more correlated than ever and hedging correctly (without paying too much) is very difficult. Think LTCM.

Con: Basing large $$ decisions on gut feel makes it prone to emotions and mood swings.

Pro: This is how many traders operate. They make lots of money so they must be right, right?

Con: This is how many traders operate. They play with other people's money so it is easier to isolate emotions. Even then, we get an Amaranth Advisors once in a while.

My put selling focused options trading strategy is as follows:
1. Identify a good quality stock that I would want to own forever (or at least 5 years).
2. Identify a price at which I would buy right now. I usually do this by looking at fundamentals. I assume future earnings are either at or below the trailing twelve month (TTM) earnings. Given that, I low ball a P/E ratio based on historical lows of the stock or industry.
3. Take a quick look at technical support levels.
4. Try to pick a stock that satisfies the above and has high implied volatility relative to historical volatility (IV/HV).
5. Check that there is no news shocks coming up. This may include earnings reports, acquisitions, law suits, economic indicators, etc. Obviously you can't avoid all such outside factors but avoid the big ones. For example, do not trade RIMM on the day of earnings (at least in this strategy).

Take either track a or track b depending on how badly you want to own the stock now. Track a is good for a stock that I really want to own now since it maximizes theta. Track b is good for a stock that I want for the long term but not necessarily right now. I generally use track a for bottom fishing / knife catching and track b for long term Buffett style portfolio building.


6a. Write a near term at the money (usually front month ATM) put above a technical support but higher than my would buy right now price. The idea is to make money either from time decay or a drop in volatility. The front month ATM has the most theta and thus the most time decay. Since we picked something that had high IV, we benefit from a drop in IV.
7a. If I get assigned, I tried to sell a covered call on it such that the if the covered call is assigned, I would at least break even.

6b. Write a long term out of the money put such that if assigned, the cost basis is at or below than my would buy right now price.
7b. Sell a covered call if the stock becomes overvalued or is nearing near term resistance.

8. Repeat step 7 until stock is gone or if fundamentals shift greatly. Nothing says I can't change my mind and dump the stock. The above is the options trading strategy given that I like the stock.

Risk Management:

• Only sell options with enough time premium such that if I buy it back at 0.05, I can make a good return. Failing that, it must be close enough to expiration (I usually only do close to a week).


• Since I would not sell options for small time premiums unless they are close to expiration, I buy back options with small time premiums unless they are close to expiration. This is not a hard rule. Some times it does not make sense to only buy back an option that has huge unrealized losses. In that case, I usually either: give up and buy back the option (reduce my delta), roll the options down and/or out (maintain delta), write additional options (increase delta). That really depends on my outlook for the underlying.


• This requires a large amount of capital and is very high risk. The drawdowns will kill you. A more sane person would probably utilize stops. One of the obvious risks is that during a market downturn, you take assignment on a lot of stock and need to be able to carry that stock (either with cash or margin). To make things worse, when you are carrying stock during a down turn, you cannot make money by selling more options since you run out of buying power.


• This is just a strategy that I sometimes may follow. This is not a recommendation for you to use this strategy. In fact, it is a warning to those who choose similar strategies. It's feast and famine. When volatility is high and markets are range bound, it is all profit. In most other cases, it's not so happy.

This is the recipe for making my secret sauce. In theory, theory and practice are the same; in practice, they are not. Making money requires stock picking skill and trading ability. The key to this whole house of cards is step 1 which I gloss over.