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The game of wealth management

Like Monopoly, Shirtsleeves to Shirtsleeves aims to make finance fun to learn.

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Bob Moon: Maybe you're familiar with the old saying "shirtsleeves to shirtsleeves in three generations." It basically means somebody a few generations back got rich, but the successors in the family had no success in managing that wealth and they ended up back to square one.

Knowing how to talk to the kids about money is a problem even wealthy families face, so the wealth management firm GenSpring has come up with a conversation starter of sorts: A board game that's called "Shirtsleeves to Shirtsleeves."

As Marketplace's Sean Cole reports, it's sort of a Monopoly game for rich people.


Sean Cole: The game isn't commercially available. It's just something that GenSpring developed for its client families, who are all worth $25 million or more.

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.

Karen Bongard: 1, 2, 3, 4, 5, 6...

Some of the squares have instructions on them…

Bongard: Pay taxes. Roll and pay 1 million times the number.

And every turn, you have to draw a card.

Bongard: Cash Cow. Your son plowed your Ferrari through a field before flipping the car. He's OK but the car's ruined and the prized Holstein the car landed on can't be replaced. You are being sued by Farmer Betty for damages and mental distress. Holy Cow! Lose $3 million.

Everyone starts in generation one and after a few turns...

Bongard: 1, 2, 3, Stop. Wealth transition. Roll again.

You enter generation two and then three and there's a separate deck of cards for each.

Steve Barimo: The goal of the game is to get through the third generation and still have money left. The winner is the person with either the most money or the least losses.

Steve Barimo is chief innovation officer for GenSpring. He had a big hand in creating Shirtsleeves to Shirtsleeves. He says the company just wanted its clients to understand how rich families lose everything without actually having to lose everything.

The key to staying rich, he says, is good family communication and the game is supposed to be a sort of conversation lubrication.

Barimo: So people can get very comfortable, not only aware but very comfortable with some of the issues that can present themselves and then actually as a family talk about whether that can happen to them and so just the sheer communication that can go on within the family is an incredible benefit from families having played this.

But the family who played the game for me did more exasperating than communicating.

Jaymie Bongard: Lose $16 million?!

Madison Bongard: Aw.

Jaymie: That is sick. I don't even have that much money.

Jaymie Bongard lives in a fancy house in Toronto with his wife Karen and their kids Haley, 18, and Madison, who's 15. They're not GenSpring-wealthy.

Actually, Jaymie wouldn't tell me how much the family is worth, which isn't a shock as he doesn't tend to share that kind of information with his daughters either. He owns an insurance company and Karen sells insurance, too.

Karen: So sometimes they ask, "Well, what happens when you die? Do I have to work?" Well, yeah, you have to work, but they also want to know how much they would get if we die.

Cole: Is that true?

Madison: Yeah.

Anyway, Jaymie doesn't think it's time for those conversations yet.

Karen: I think my kids are too young still. I think this would be more apropos to somebody whose kids are just getting married or in the family business or stuff like that. I think my kids are still a bit young. I'm not sure that it's something they would appreciate talking about anyway.

He's right. Haley, the 18 year old, actually said she didn't like talking about this stuff. Moreover, she didn't think the game was very useful.

Haley Bongard: 'Cause it's really like you can't help it. It's mostly luck. You roll it and you can't be like "Well, nah, I'd rather do this." You don't really have choice.

Great point, says Steve Barimo. And next year GenSpring is coming out with an advanced version of Shirtsleeves to Shirtsleeves that will let players control the outcome of the game. But I have an even better idea:

Barimo: Shoot.

Cole: Shirtsleeves to Shirtsleeves Twister. Huh? Huh?

Barimo: I like it. Well, would you be willing to play?

Cole: I'll be there with bells on. I'm gonna make a hundred dollars with this idea.

Barimo: Well, maybe we'll collaborate on that.

Contemplating a major career change, I'm Sean Cole for Marketplace.

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