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How I beat career entrepreneurs and real estate investors in Monopoly at age 12

Updated: Jun 30, 2020

I hope all of you are enjoying high-quality (and not just high-quantity) time with your families. The sales and presumably play-time of board games like Monopoly have sky-rocketed recently for obvious reasons. This makes me smile because my mind conjures the enchanting image of families not only having fun together, but also learning how to be greedy capitalists together. The latter was my experience as much as the former, which means that my main take away from the game was developing a robust strategy for demolishing the competition, more than it was memories of engaging in light-hearted connection with loved ones. Don't worry, I DO love my family, and wouldn't trade them for any amount of money (no good offers yet at least).

Before I get to a critical component of the objectively best strategy to win Monopoly, I'll first describe the circumstances around how I discovered it. In a world of constant variability, I've found that the process alone used to determine effective strategy is often more important than the final strategy itself.

Unfortunately for most lovers of the game (including myself from age 10 and up), the barrier to entry is high in terms of actually organizing a game with 3 or more participants (victims) together who can all commit to multiple hours sitting around a board game. 'Spoons' was always a much easier sell growing up... This makes it difficult to play often, and consequently, learn about the game and how to win every time. Thankfully for me, during Christmas and Thanksgiving gatherings, there was always enough extended family around to organize a real, six-person game of Monopoly.

Keep in mind, every one of my mother's siblings is in the real estate industry, and all of them own small business, as do both of my parents... you could say they brought some experience to the table.


One Christmas when I was around 12 years old, my extended family and I were playing a game of Monopoly, when I began to notice a serious issue with the way we were bending the rules without even realizing it. Even if you are familiar with the game, please read on, as breaking down the rules step-by-step is crucial in developing proper strategy.

Per my usual strategy at the time, I had already acquired two or three full "Monopolies". Owning a Monopoly means you own the properties that all share the same color group, and are eligible to begin "building" (placing a plastic green house or red hotel) on these properties, which earns higher rent payments from players who land on your particular owned board space/property.

The more houses you build, the more rent you get, until you get to build a hotel, which earns you the maximum rent possible for that given space. In order to get a hotel on a property, you have to have 4 houses on all three properties in your color group monopoly. In other words, you cannot build any one property higher than the other properties by more than one house at a time. For example, three houses on each property in a color monopoly are allowed, so are two houses on two properties with three on the third property, but four houses on one property and only one house on the other properties in your monopoly is not. The game comes with a limited amount of little plastic houses and hotels (32 houses and 12 hotels, and yes I still have those quantities in my immediately-available memory). Once you've upgraded from four houses to one hotel, your old four plastic houses go back into the box until another player is ready to use them to build.

The way we had always (incorrectly) played was by adding fake "houses" to the game when the physical supply of the plastic house pieces was depleted. We just figured the maker of the board game was simply too stingy or obtuse to include more than 32 houses with the game.

At this point in our holiday game, I owned 4 or 5 hotels, and another handful of houses on my properties. This is when my 12-year-old self identified a highly valuable strategy that I simply could not play on without employing, and was forced to confront my family (the entrepreneurs and real estate professionals, and pushy ones at that) to insist that we play the game exactly according the rules explicitly stated in the manual:

BUILDING SHORTAGES… When the Bank has no houses to sell, players wishing to build must wait for some player to return or sell his/her houses to the Bank before building.

- Monopoly Rule Book


None of us had ever read this rule, nor had I recognized it's clever significance until it really mattered, and had I not seen an opportunity to use a game-winning strategy, we would have continued to "play the way we always had" and never bothered to find the rule in the manual.

Why did this rule matter so much now? Between my eight monopolized properties, I could theoretically use all 32 houses. 8 properties * 4 houses/property = 32 houses—every single one of which could be in my name.

Until this day, I had always sought to acquire as many color monopolies and as early in the game as I could. This is a good strategy, since you can build and really wipe out the competition with house or hotel caliber rent, again, which I already had at this point in the game. The problem with this strategy is that it's only halfway effective. If you play with other somewhat sharp players, everyone catches on to the color monopoly idea quickly, and while you end up making a lot of money on your hotels, you also lose just as much or more from hotels owned by other players. A common, separate strategy is to block other players from acquiring monopolies themselves, since it puts you at risk of such a hotel battle.

Herein lies the less common, game-winning strategy: to leverage your coveted, un-monopolized (single) properties for cash not only to acquire your own monopolies quickly, but also to acquire as many houses as you can quickly. This is the secret sauce that no one in my family had noticed.

Intuitively, you want to build and keep as many hotels as you can, since they earn higher rent. I realized this. My next move, however, was to sell all five of my hotels, downgrading just one step to four houses per property. This instigated some suspicion from my family members, but didn't elicit any push-back until they realized exactly how this move hurt their chances of winning. It was my older brother's turn next. He decided to he wanted to build houses on one of his monopolies. He had enough money to buy something like seven houses, which would up the rent on his unbuilt properties from around $40 to over $500 for each space. That doesn't just help him make more money, it puts me at risk of owing such a bill each time I circle the board, and makes my position owning hotels less powerful. Some quick mental math made it clear that losing even a couple of hundred dollars in rent per payment on my properties by downgrading my hotels to houses is worth it if it means I can physically prevent others from ever being able to charge more than base rent on their properties (which doesn't exceed $100, even on the most valuable properties).

The arguing and deliberating over rules began when I told my brother he can't just "substitute" a coin or an almond for a little green plastic house... he has to wait until I sell some of mine.

His, and subsequently my uncle's response was, "Well, sell a house and upgrade to a hotel so I can get a house!"

We're Lebanese, and to say we had a tendency to bicker a lot as a family is an understatement. We aren't just comfortable with confrontation... we downright enjoy it. Chaos ensued.

I won the battle by referring to the rule quoted above, and we continued the game. After saving up some more cash, my brother wanted to go straight to hotels during his next turn. He assumed he could skip buying houses, and go straight for the hotel as long as he paid the equivalent amount of cash to get there. The rest of the table obliged. They were wrong again, and I turned to the manual and argued a very subtle wording found in the letter of the law:

HOTELS… When a player has four houses on each property of a complete color-group, he/she may buy a hotel from the Bank and erect it on any property of the color-group.

- Monopoly Rule Book

As you might guess, I emphasized the bold text above in my appeal. My brother didn't have four houses on his properties, so he couldn't buy a hotel. And now there were no more houses to buy, since I owned them all.

There were of course plenty of hotels available to purchase... just no one qualified to purchase them except myself, but of course I had no use for them at this point. I was renting my properties at ~70% max hotel rates (see picture, hotel rent on Oriental Avenue is $550, but four houses still gets you $400, and 400 ÷ 550 = 72%), and was never paying more than base rates when I landed on unbuilt properties. Victory was imminent, we all stayed family, (but I think it was because you only get to choose your friends) and I became the undisputed Monopoly champion for years to come.


The rules I quoted were not accidental oversights of the game. The creators of Monopoly (I assume) intentionally restricted supply of buildings in order to allow players to capitalize on the shortages, and monopolize houses. Not so obvious, yet what won me this game against my family, was the fact that even monopolizing hotels is not as useful as monopolizing houses, since it leaves other players the ability to still capture near-hotel rates, whereas monopolizing houses leaves them only skimpy double-digit rates.

The title "Monopoly" is fitting when you understand that one of the objectives of the game is to acquire a color monopoly on similarly colored properties on the board, but there is another angle of the word that causes winning to be nearly fool-proof. To win, you want a monopoly on the physical buildings included in the game as much as you do the properties themselves.


In short, my strategy recommendation is as follows:

1. Get color monopolies (specifically on the cheap part of the board) fast.

Even if you pay a premium for them or give others difficult-to-build monopolies such as Park Place and Boardwalk...

The reward will greatly outweigh the upfront initial investment and most likely the risk of actually landing on high-dollar spaces like Boardwalk or Park Place.

2. Focus on building up lower-dollar real estate, and build early.

The goal here is to get quick income and start taking control of the housing supply.

Why lower-dollar properties?

Spaces on the board go from "low potential" real estate that is cheap to buy and build, (with lower rent competing players pay you) on the first side of the board after "GO", to real estate that is expensive to buy and build toward the end, (with higher rent per payment).

For example, building houses on Oriental Avenue (early, light blue space) only costs $50/house. Each house on the expensive side (i.e. the side with Park Place) costs $200/house. This means the upside of owning spaces like Park Place, though great in magnitude, takes much longer and is, therefore, less likely to be built. This means owners will spend most of the game taking many small hits, and never having enough cash to get their property to produce large returns.

3. Ruthlessly hoard houses, don't bother buying hotels.

Buying hotels is greedy and short-sighted, and only enables others to build on their property and charge you big bucks. Better to block anyone from building at all.

In other words, don't feel bad when the other players are peasants and you're the king. In real life, we celebrate others doing well. This isn't real life, so don't just succeed, make sure others are never more than mediocre or broke.

... don't think that way in real life. It doesn't work that way. Everyone can win in real-life when they simply do what winners do.

Keep reading my posts to find out how to win by design and minimize downside while maximizing upside.


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