Shirtsleeves to Shirtsleeves is an educational boardgame developed by GenSpring Family Offices, a wealth management firm. Its purpose is to encourage intergenerational discussions of wealth management within families. The game name comes from the saying, "From shirtsleeves to shirtsleeves in three generations," meaning that a family fortune earned in one generation can easily be lost by another.
This game was featured on the news radio program "Marketplace" and a version of the story can be found online here: http://marketplace.publicradio.org/display/web/2008/06/25/sh...
A summary of gameplay, excerpted from the "Marketplace" report:
"Every player starts with $25 million in play money and from there the game is kind of a cross between Monopoly and the game Life. You roll the die and move your piece along a snaky row of squares in the shape of a dollar sign...every turn, you have to draw a card...Everyone starts in generation one and after a few turns...You enter generation two and then three and there's a separate deck of cards for each."
According to the report, GenSpring is coming out with an advanced version of Shirtsleeves to Shirtsleeves that will let players control the outcome of the game.