I have been asked several times in the last six to nine months about investing in some down and out company (Citigroup, GM, Nortel) on the thinking of “what’s the worst thing that happens? I lose a few pennies/dollars a share. If the company turns around, I can double or triple my investment!” What scares me is that half the people who ask me this question are deadly serious. I tend to think of this type of stock investing as being in the hail mary school of thinking- named after the hail mary pass in football where you heave the football into the end-zone in some low percentage, high reward play made in desperation. It is, in many respect, the flip side of penny stock investing. Put your money in a business who’s salad days are in the rear view mirror in the hopes that there is still enough goodwill in the market to effect a turnaround with smart management. Think of Apple. Nissan. Puma. But is this an effective
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