How to Win at Monopoly Every Time
I may not have the best business acumen, but I am pretty darn good at Monopoly. How many games I've actually won, so to speak, I can't tell you. Then again, nobody really wins at Monopoly, right? It's one of those games that's starts fast and furious, when you're gathering property and getting your cash all lined up, and then a few people drop out and the next thing you know everyone's disappeared.
So, if winning Monopoly is important to you (or, if you see it as some kind of reflection of your potential as an entrepreneur) you might want to follow Truman Collins' Probabilities in the Game of Monopoly, which has crafted a mind-boggling science out of this classic game. Here are some tidbits courtesy of Tim Darling:
- Always buy Railroads; never buy Utilities
- At the beginning of the game, largely ignore Sides 3+4 of the board and focus on acquiring a complete C-G (Color Group) in Sides 1+2. After acquiring one of these C-Gs, build 3 houses as quickly as possible: no more houses, no less!
- Once your first C-G starts to generate some cash, focus on completing a C-G and building 3 houses in Sides 3+4.
- Single properties are the least good investment if you don't build on them.
- The only exception to the above rules are when you need to acquire stray properties to prevent your opponents from completing their C-Gs to accomplish the above strategy.
Will this surefire Monopoly strategy make you a successful businessperson in real life? If you have the ability to buy multiple railroads and an electric company on any given day, I would say... yeah. Definitely.









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