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It seems like your stuck between a rock and a hard place Howard. If you encourage him that he will do ok and make his money back soon, you might be lending him money pretty soon. On the other hand, if you try to bring it to his attention that his portfolio is overvalued and speculative, i doubt he would graciously thank you:) Lets admit it, your "superiors"(who seldomly turn out to be actually "superior") generally dont like being corrected or instructed by their "inferiors"
I would think you should just stay away from the subject of investing with him. If theres one thing that your sergant will like less then being wrong is being PROVEN wrong. I think that some people are too hard headed to be told therye wrong no matter what the case is. I know many people like that. Meanwhile I would just let your record speak for itself, it will over time. And by the way, damn good return for last year. Beating the S&P would make even Buffett a happy man. Keep it up, and good luck!!!
eric
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