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Sirius XM: A Tale of Two Stocks

NEW YORK ( TheStreet) -- When I was asked to contribute a story that is fitting of Charles Dickens' masterpiece "A Tale of Two Cities," the first name that I thought of was Sirius XM (SIRI - Get Report).

After Sirius rose to prominence by signing exclusive deals with high-profile talents including Howard Stern and securing rights to the National Football League and Major League Baseball, the financial crisis brought the company to its knees. With no one buying cars -- which Sirius needed to increase its satellite radio subscriptions -- bankruptcy seemed the last resort.

Essentially, while most companies can proclaim "the best is yet to come," very few, unlike Sirius, are able to truly appreciate "the worst of times" without detailing a near-death experience.

From an investor's/trader's perspective, however, the "best and worst" have different meanings. For me, my best and worst as a trader came when mistiming the movement of Sirius' stock.

The Best of Times: 84% Gains

A company recovering from or teetering on the brink of bankruptcy means a lot of things to different people. For some, it's a sign of poor fundamentals and an absolute sign to stay away from the stock. For others who have a higher risk threshold, bankruptcy is a "haystack" and there's a needle to find in there somewhere. I was in the latter category.

I figured that with a bit of luck I'd find three needles and possibly 10,000 more. My goal was not to get rich. I never believed it was possible playing a penny stock. I wanted to beat Wall Street. But having sat at many poker tables in Las Vegas, I also understood the odds.

Many Sirius XM geniuses still proclaim they timed the bottom perfectly and bought in at 5 cents per share in February 2009. I was not that smart. In fact, I still argue today that this was a dumb move that turned out to be smart -- even if the potential loss was (relatively) minimal. What's the difference between 5 cents and 20 cents? Or even 30 cents?

Poker players know that to make money, one has to be willing to leave money on the table. This means that you can't get too greedy. It pays to be patient and watch to ensure that you have a winning hand. Accordingly, my first trade in Sirius occurred one month later -- on March 17 2009. I bought a little over 15 thousand shares at 32 cents.

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