I've been a member of a small investors club for a few years now, and to say the last 12 months have been rough is a huge understatement. We've lost significantly in the market, although some of our private investments have done okay (as well as some investment in gold). Occasionally we make limited, non-controlling buy-ins for various private businesses, either as direct investments or structured loans. Yesterday we agreed to buy a restaurant in Seattle that I have been going to for a few years now. Despite the climate, it looks like a pretty good buy given food, the neighborhood and the management. While not, by any means, a controlling interest, it's enough that we should do pretty well in a market where 2% bonds look like genius. If we have this right, we should be getting around 9% if you don't count the fringe benefits (i.e. I eat there a few times a month or free, they are now stocking my favorite drink etc.).
If you have a chance and are in Seattle, check out Amore on the corner of 5th and Bell.