you've made in your life, to date? Investments, purchases, sales, whatever, however you wish to quantify it. No need to get into dollar specifics, nobody wants to do that, just in general.

I'll go first.

Smartest: invested in real estate land purchase, a fairly sizeable chunk, that has market value, based on actual per acreage sale of immediate parcels around it, of between 7x to 10x what paid for it over course of past 15 years or so. Could conceivably sell it right now if desired. Have had out of the blue offers by developers. If closer to retirement age, as many have been discussing today, would likely pull the trigger on it. Gonna hold a while longer.

Dumbest: stupidly got caught up in the 2000 dot com bubble irrational exuberance, investing start up venture capital (not a ton, but enough that I surely wish I had it back), in a start up, that was, in concept very very similar to Angie's List, before Angie's List existed. It ultimately went bust, and lost whole investment. Irrationally exuberant indeed.

What's your best and worst? In general.

And let's go ahead and get the mandatory hookers and blow out of the way now. Whether those two are smart, or dumb, is up to you. ;-)