How to Cover Your Assets in a Speculative Stock Position

NEW YORK (TheStreet) -- Speculative investing gets a bad name.

That's because too many investors treat it like they do phone calls, text messages, Facebook posts and Tweets after having too much to drink. Drunk dialing, texting, Facebooking and Tweeting are all sloppy, not very well-thought out endeavors that tend not to end well.

When you speculate, you should do it not only in moderation, but with companies you know well.

All too often, investors associate low-priced stocks or once-healthy, now-depressed companies with speculation. While these and similar factors might ultimately be ingredients of a speculative play, you absolutely cannot use them -- in and of themselves -- to identify specs.

I like to take spaces I know well and search for speculative opportunities within them.

For example, I break media and telecommunications stocks down into large companies with their hands in a bit of both (e.g., VZ, T, RCI, BCE), pure-play old guard media (e.g., TWX, DIS, NWSAB) and new/social media tech types such as Yahoo! (YHOO) and Pandora (P).

Because I know the space well and have had success with several of its not-so-speculative plays, it makes sense to up the risk here and there.

As a general rule, I do not go long a speculative stock if it's not optionable. It must not only have options available to trade, but there needs to be liquidity and a healthy selection of strikes and expirations. Sufficient volume to keep me away from crazy bid/ask spreads helps as well.

Consider Yahoo!

In Marissa Mayer is a Woman, Hear Her Roar and Buy Yahoo!, I suggested that, with the stock trading around $15.80, it might be time to buy.

I did just that, accumulating a small position at a cost basis of $15.89. The stock promptly ran past $16.00, pulled back and then, after closing Monday's session at $15.77, bolted to around the $16.50 level in earnings-induced after-hours trading. In case you missed it, Yahoo! turned in a solid report Monday afternoon.

On Friday, I wrote weekly YHOO $16.50 calls (expiring Oct. 26) against part of my position.

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