In 1983 a friend and research analyst convinced me to put $2,000 in a thoroughbred limited partnership in Kentucky. Never invest in anything you have to feed or paint, but I did it anyway. Kentucky's horse industry took a bit of a dive, and we lost most of it. OK, dumb, but not tragic: but I was holding it in an IRA account: no tax deduction on the loss. Now THAT's DUMB! Oh, yeah, my friend is now a professor at a prominent business school. (To be fair to him, the other securities he helped us with have done quite well. He also taught me to evaluate purchases my self, and not rely much on the advice of others.)