Business Lessons From America's Favorite Board Game

I recently watched a documentary called “Under The Boardwalk: The Monopoly Story”. It tells the story of American’s favorite board game from its origins all the way through its annual international word championship. In learning about Monopoly strategy, I took away some great business lessons.

Boardwalk Is Not The Best Property: At first blush, Boardwalk and Park Place appear to be the most valuable properties on the board. They carry the highest price tags and require opponents to pay the most rent. However, savvy Monopoly players know that the orange properties are the most valuable. Players land on the orange spaces (St. James Place, Tennessee Avenue and New York Avenue) more often than other properties. Many Chance and Community cards (Go to Jail, Advance to St. Charles PlaceAdvance to Reading Railroad and Go Back Three Spaces) place players on (or in line to land on) the orange properties. Further, those sent to jail via the “Go To Jail” corner spot or roll doubles three times are mathematically likely to land on the orange properties once they are sprung (i.e., common rolls of 6 or 8). These properties are therefore more valuable despite their lower cost.

In business, it is tempting to buy the premium service or top-of-the-line product. Often, however, the best solution is not the most expensive. We spend a lot on monthly pay-per-click advertising but our average position is usually only between 2 and 3. We rarely bid for the top position because we actually have determined that we convert more leads from lower positions (and of course save money in the process).

Going To Jail Isn’t Always Bad: Early in the game, you need to get out of jail as soon as possible. During the early stages, it is a “land rush” where your primary objective should be to buy as many properties as possible. This means, immediately paying the $50 “get out jail” fee rather than trying to get out for free by rolling doubles in one of your next three turns (you only roll doubles 17% of the time). However, later in the game when landing on an opponent’s property becomes expensive, you’re much better off cooling your heels in jail and actually hoping you don’t roll doubles. In fact, ironically, Monopoly championships are often won by the player that is lucky enough to be incarcerated at the right times.

Likewise, in business, having good timing is everything. Savvy business leaders know when they should pull the trigger and when instead to sit on the sidelines. For some, the former is hard.  Over-analysis and fear of making a decision prevents some from taking advantage of prime opportunities. For others, patience is an issue. They find it difficult to sit on one’s hands even though it is the right thing to do.

It took months and months but I recently re-launched my website for those looking to fight a New York traffic ticket. I knew early-on what my key photo would be and haven’t wavered from it. On the other hand, I was unsure about other elements around the photo including the introductory text. It was frustrating to hold off but, in the end, I realized that it was much better than prematurely launching with poor messaging.

There is No Money For “Free Parking”: Many people believe that you get money for landing on Free Parking or an extra $200 for landing on Go.  However, neither one of these practices are authorized in the official Monopoly rules.

Following instructions, understanding your written agreements and knowing applicable laws are all real-life examples of this fundamental principle. I can’t tell you how many times I was able to win an argument simply because I read a document. I am currently in a dispute with my car rental company over a lost key. They want to charge me $871 to replace the lock-set. However, the agreement only states that I am responsible for the cost to replace a lost key. Of course, I only learned this information by reading the “fine print” thereby gaining an edge.

In sum, if you recognize value, have good timing and know the rules, you’ll be in the best position to monopolize your industry

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4 Comments. Leave new

  • riverside dui lawyer
    August 2, 2012 12:55 pm

    The funniest thing about Monopoly is the fact that very few people actually play according to the rules. Every time I read about Monopoly, I find new things that I didn’t know beforehand. You can pay $50 to get out of jail? People thought you got money for landing on free parking? There always seem to be house rules 🙂 Some of the business tips I learned from Monopoly were mostly about making sure no one stole money from the bank or me while I went to the bathroom 🙂

  • Great post Matt! Great use of analogy to make very valid points, and I of course couldn’t agree more. The right picture and the right words can in fact make a big difference in acquisition and conversion – so big kudos to you on the blog and on a terrific new website! I’m sure you will continue to realize success!


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