How to Never Lose Monopoly Again

monopoly and real estate investing

I once beat a friend in Monopoly in twelve minutes.

I don’t know if that’s a world record but it’s got to be close. During our summer after high school ended we played a game of Monopoly every single day. (I bet you can guess how popular I was with the ladies…) We became extremely quick at the game and memorized every card’s value and the distance between every spot on the board. My twelve minute game was a result of a nearly perfect set of rolls in succession, giving me two complete monopolies within five minutes and my friend landing on them four times in a row.

After that summer, I ended up winning every game of Monopoly I played for over six years (I’ll tell you how I finally lost at the end of this post!).

I don’t say this to brag (okay, maybe a little!) but to give a response to people who say “Monopoly is a game of pure luck.” Yes, my twelve minute game was incredibly and positively influenced by luck, but had the same set of rolls happened to someone else, the game may have turned out much differently.

While there is no doubt that luck plays a role in the way Monopoly is played, luck has actually very little to do with winning the game. Every time you roll the dice, you have no control over the position you land on. You don’t know what “Chance” or “Community Chest” is going to do to your portfolio. You don’t even have control over who starts the game or what the dice will show.

You do, however, have control over how YOU play the game that’s set before you. Just like the Casino that has a 51% edge on a game of Blackjack, the smallest edge over the long term will result in almost a guaranteed win. By utilizing small tricks and techniques in Monopoly, you can improve your odds slightly and improve your odds of winning exponentially. Below are three different strategies you can use to improve your game.

The Strategy

1.) Buy Everything.
The first step in winning Monopoly is to buy everything. It doesn’t matter what you land on – buy it (yes, even the terrible Electric Company. If you are saying right now, “I love the Electric Company! It’s not terrible!” Yes it is. In fact, I’d like to play you in Monopoly. Nevertheless, buy it anyways.)

2.) Never have more than $100 in cash
Have you ever played with someone who loves to show how much money they have in their possession? Do you gloat about that? This is hands down the number one mistake people make when playing Monopoly. Believing “cash on hand” is equal to success is not only misleading but turns that person into purely my own personal savings account for me to collect on later in the game. There is always one in every game – and I love it.  I will buy anything I can, add houses as quickly as possible, and offer to buy properties from others – anything to get my cash out of my hand and into the game.

3.) Do whatever it takes to get a monopoly – even a bad one.
The game I won in twelve minutes was won primarily because I bought the first two Monopolies on the board – the lowest priced ones. It doesn’t matter which Monopoly you get as long as you get one and get one quickly. I will even trade other players a better Monopoly for a worse one. I don’t care that much if they have one as well – I just need to make sure I have one. In fact, by making a trade which gives you and another each a Monopoly, you essentially kick all the other players out of the game immediately. This is why buying everything is so important (see #1 above). You cannot trade if you have nothing to trade with. (P.S. – Owning the four railroads is not a winning Monopoly. Only collect them to trade later).

4.) Mortgage everything I own and put all cash into that one monopoly.
Once I have that one Monopoly, I flip over ever single property I own and “mortgage” them to the bank. The bank will offer me ½ of the value of those properties. I then put every dollar (except $100, see #2 above) into building that Monopoly with houses and hotels as soon as possible.

Monopoly is NOT Only Played on the Board

While the four strategic points I discussed above are important – they are not the most important. The most important rule of Monopoly is understanding that Monopoly is not only played on the board. Monopoly is a game of people.

By watching other players on how they interact with their finances and each other, you can use those players to get further ahead. The easiest way to do this is by finding win-win situations that help you and another player get ahead. As I mentioned earlier, my helping another player gain a monopoly you can eliminate other players decisively.

Furthermore, you will begin to realize the strategies that other’s are playing with. Are they a “cash hoarder?” An “it’s only luck” player? A greedy player? A mean player? A “this is a stupid game and I don’t know why Mom is making me play” player? There are many different personalities found in the game of Monopoly. Learn what they are, what people truly want, and use that to help them get what they want and at the same time get what you want.

Monopoly Applied to Real Estate Investing

This is BiggerPockets, after all. The point of this blog was not simply to talk about how awesome I am at Monopoly (wink!). I use my Monopoly strategy as an analogy for building wealth in life through real estate investing.

1.) We all start with the same thing – nothing.
Now, obviously some people are born into families with great wealth and others with extreme poverty. However, those are simply like the luck of the roll but have very little to do with winning the game. Often times I play a game of Monopoly and someone will brag about all the cash they have or how they now own all four railroads. In the same way, people brag about the awesome new car they bought (and financed heavily), the beautiful home they just paid too much for, or the great job that Daddy got for them. These things, while potentially they could be beneficial, usually end up costing more in the long run. Life isn’t fair, and either is Monopoly. In both cases we must learn to adapt to the cards we are given and use the “luck” or lack-thereof to move forward.

2.) It’s Not A Game Of Luck
Not surprisingly, the people who believe Monopoly is purely a game of luck are also often the same people who believe building wealth is simply luck as well. They believe that some are born with that luck and are given things their entire life while others (themselves) work hard but never seem to get anywhere. Clearly, however, building wealth is not a game of luck but rather a result of positively responding to the place we are in life. We may not have control over every part of our lives, we do have control over what we do with the life we are given.

3.) You are not rich until your money is making you money
A good friend and successful real estate investor is fond of telling me the greatest lesson he ever heard which was simply “You are not rich until your money is making you money.” Having piles of cash, while nice, is often nothing more than a savings account for someone else to take later (Usually the government). By giving your money a shovel and wheelbarrow and sending it to work for you, you will begin to experience the power of exponential growth and passive income.

4.)Just Do Something
This doesn’t mean to buy a bad investment. Notice in Monopoly there are no investments that lose money, which is why I believe in buying everything in that game. In life, it’s important to do your homework and not be ignorant, buying something because it’s pretty. However, if you are not ready to buy a large investment, it doesn’t mean you can’t start small. Just do something even if it isn’t the apartment building or house flip you want to do someday. It could be as simple as maxing out the funding on your 401k, investing in a Roth-IRA, partnering with others on a flip, or simply paying off your credit card debt. The point is – you need to take action.

5.) Real Estate Investing is Game of People.
If you are an experienced real estate investor – you already know this to be true. Real estate has just as much to do with managing people, making friends, and networking as it does with drywall, paint, and rent checks. Without the interactions with others, your ability to grow as an investor will be severely impeded. By learning what other people want and creating win-win deals that give everyone what they want, you can move ahead and closer to winning the game.

How I Finally Lost…

Real Estate Investing and Monopoly. While it’s not a perfect analogy there are so many good lessons to be learned. Perhaps it was fate or just a quirk in my personality that made me so obsessed with the game of Monopoly. Interestingly enough, my friend who played Monopoly with me every day that summer is also now a real estate investor and doing very well (and also a member at BiggerPockets!)

I mentioned that I went over six years without losing a game of Monopoly. Perhaps you are wondering what finally brought me failure?

I played against my wife.

Thanks for reading! If you made it this far, please leave me a comment below! I’d love to hear about your investing strategies, Monopoly stories, or questions about anything at all relating to real estate!

Image: Askins

This Article is Copyright © 2004-2012 BiggerPockets, Inc. All Rights Reserved.

How to Never Lose Monopoly Again




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