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Strategy in Monopoly, and in business

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A lot of people don't know this about me, but I am CRAZY about Monopoly. I absolutely love the game. In fact, I actually collect Monopoly boards.

My favorites include a Londonopoly board, a Dr. Who board, the Millennium edition with plastic money, and my brand new Firefly edition.

As you might imagine, I am also a very good Monopoly player. I can't say I'm undefeated - luck does play a part where dice are involved - but I win far more often than not. And, as a result, my friends and family generally consider me a ruthless cutthroat fill in your favorite four-letter insult here when I'm sitting across from them.

But here’s the thing. The secret to winning Monopoly is NOT by being a cutthroat competitor. No, the secret is in identifying property trades that are actually win-win (positive sum, if you will) solutions.

I almost NEVER accept a trade offer. Why? Because the person offering a trade will, without a doubt, have an agenda that is either patently obvious or nefariously hidden. And the trade offered is rarely - make that never - in my best interest. That said, once the board cycles over to my turn, I almost always counter (if I can) with an end-game that appears both obvious and clearly in the equal interests of my potential trade partner and me.

This counter offer is almost always accepted.

I'm sure there's a game theory that explains the math. But anecdotally speaking, there is a remarkable correlation between the losing players and the players who argue and cajole and attempt to force bad deals. These folks generally create distrust and build resentments that keep stronger positions from ever developing. Meanwhile, my sneaky gameplay that involves being nice consistently grows my position through mutually beneficial - dare I say trustworthy - dealmaking.

Sure, there's still a strategy to it.

The guy who sacrifices everything for Boardwalk and Park Place is usually the first guy out. The gal who secures the orange properties near Free Parking usually ends up winning. (I know folks with very effective strategies involving heavy investment in the cheaper first-row properties, or with a concentration on railroads and utilities, etc. Whatever works, right?)

But those strategies matter not when a few unfortunate dice rolls (not to mention Chance and Community Chest!) teach you valuable lessons about the Universe’s refusal to play along.

Life happens, even on a Monopoly board. Circumstances beyond your control will almost always force you to work WITH your opponent if you hope to secure a monopoly. I say, if you HAVE to work together, then work TOGETHER. You may not win every game, but you'll finish second far more often than fifth.


Don't let Jeffrey M. Peyton's accolades, business accomplishments or cool demeanor fool you. The Sun's regional director of marketing has wing-walked on an airplane at 700 feet, co-piloted the Goodyear Blimp, swam with sharks, and managed to obtain paperwork officially declaring him “legally sane.”

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