How to Never Lose Monopoly Again

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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.

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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

About Author

Brandon Turner

Brandon Turner is an active real estate investor, entrepreneur, writer, and co-host of the BiggerPockets Podcast. He began buying rental properties and flipping houses at age 21, discovering he didn’t need to work 40 years at a corporate job to have “the good life.” Today, with nearly 100 rental units and dozens of rehabs under his belt, he continues to invest in real estate while also showing others the power, and impact, of financial freedom. His writings have been featured on,,, Money Magazine, and numerous other publications across the web and in print media. He is the author of The Book on Investing in Real Estate with No (and Low) Money Down, The Book on Rental Property Investing, and co-author of The Book on Managing Rental Properties, which he wrote alongside his wife, Heather, and How to Invest in Real Estate, which he wrote alongside Joshua Dorkin. A life-long adventurer, Brandon (along with Heather and daughter Rosie) splits his time between his home in Washington State and various destinations around the globe.


    • Brandon Turner

      It works like a charm, Eric! The biggest part – learning to play people, not the board game! (Oh, and I see you are from Minnesota – it’s my home state! (From North Branch) How’s the market there!? My parents are looking to invest!)

  1. Great post, Brandon. I also loved Monopoly when I was growing up, although I’ve never won it as fast as you. But after I was grown, was investing in real estate, and had a kid, I used to get really ticked off when he would beat me! The little snot! But as I read your post, I realized that his strategy is exactly like yours. Guess I just learned a great lesson. Thanks!

  2. Nice post- I have played many a Monopoly game, and I have developed a strategy that uses almost every element from yours.

    I think #4 should be “Mortgage every property you own except your monopoly” because you can’t develop a monopoly that is mortgaged 🙂

    Also, on #2, I would suggest if you have a property that has ~100 mortgage value, that you spend the cash and keep that one extra property un-mortgaged- you can always mortgage it if you need the cash to pay a bill 🙂 Of course, that little bit may not be worth fussing over.

    Now, here is my dilemma- I have played many games with one of my friends, and I have beaten him so many times he has my strategy mostly figured out. Now we play very aggressively against each other. I still win most of the time:) But some times we get into a game with a few other people, and they all tend t collude against me- often, they refuse to trade with me, and some times they even give each other sweet deals just to beat me! I still win a majority of the time, but sometimes it just isn’t possible. I have toyed around with changing the strategy up a bit, just to throw them off, and it some times works. Any advice?

    Oh, ad thanks for the advice on real Real Estate investing!

    • Brandon Turner

      Agreed, James. I don’t mortgage my one good Monopoly, because then it would be useless. Everything else, then pile all the goods on that one Monopoly!

      I know what you mean about people ganging up on you. I’ve been there! It’s rough. I find the best way to overcome is to be humble when playing, emphasizing constantly what terrible luck you are having and that you’ve “already lost, I might as well just help someone else.” It puts their guard down a bit. Also, there are always other people to play with 🙂

      To draw in a “Real estate investing connection,” I suppose that sort of thing could happen in real life to. You could be blacklisted from agents or others in the business. I guess in the same way, by living your career humbly and always looking for “win-wins” you can avoid it. Again, there are always other people to play with. What do you think? Too much of a stretch comparison?

  3. Melodee Lucido on

    Very fun and smart post Brandon. Brings back the fond memories of many monopoly games (where, unlike you, I was clueless) . Thanks for telling us how to win at Monopoly and apply a winning plan to our crei game too.

    And the final thought—-your wife beat you—-I lmao. Isn’t rule number one, “Never sleep with the enemy”

    Thanks so much for the fun Brandon!

  4. What a totally cool idea for a post. Very creative and well written as always.

    The only thing Id add is that unlike Monopoly where you buy everything and mortgage everything (great tip btw so I can finally beat my 13 year old), in real estate investing house flipping in particular) its as important to avoid the bad deals and not buy everything. Get your ARV right up front, calculate your 70% Rule to know what to pay for the property and grind your contractors to keep the rehab costs in check and if all that falls short…DONT buy. If it does, then monopolize!

    • Brandon Turner

      Agreed! I meant to actually make that point, so thanks for bringing it up! I don’t follow the “Mortgage-Everything-To-The-Hilt” philosophy in life. To a degree, yes – leverage is great. However, as Dave Ramsey is fond of saying, “100% of foreclosures last year happened to people with mortgages.”

      Thanks Mike! Great blog by the way! I love your domain name!

  5. @Brandon Turner- I think your analogy is pretty good. Obviously Monopoly isn’t designed to emulate a real real-estate market, but the principles for interacting with people don’t change, no matter the setting or medium (As I am fond of telling my social media clients- it isn’t anything new- the best book on social media is “How to Win Friends and Influence People”).

  6. Melodee Lucido on

    Well Brandon,
    You have definitely hit a common tender spot in many of our lives—playing Monopoly!! Good job. It’s so fun reading everyone’s take on this post—no matter their age. We are united through time with a simple (or not) fun past time.

    Thanks for the grins and the sentimental memories of (many) decades of this fun game. I don’t normally post more than one comment but this was too irresistible. I just had to congratulate you on touching people where they live—which is what writing is all about.

  7. I have always loved analogies and this one ranks right up there with some of my favorites. It makes me want to pull out my Monopoly game and employ a couple of the pointers I wasn’t already using. So far, the only thing I have really been able to beat my husband at is bowling; so, this could make for a winning date night!

  8. Hamilton Hiatt on

    Great post Brandon! There’s a short book with a very similar message (although mostly geared towards business in general rather than specifically real estate). Beyond the parallels it draws between monopoly and business, it offers some good strategic pointers on gameplay. Worth checking out for the avid monopoly fan!

  9. I bought 4 copies of the book “Everything I know about business – I learned from playing monopoly”. and passed them out to my brothers and sisters for playing so many games when we were young. Those Sunday afternoon games give you a solid foundation to build on.

  10. Jerry Davidson on

    Great article and analogy to REI. Interestingly enough, the originally filed patent for the game of what is now known as Monopoly was known by another name…The Landlord’s Game. I have a framed copy of that original gameboard submitted to the patent office in 1903 hanging in my office as homage to my favorite childhood game.

  11. BTW, do you play with that rule most people aren’t aware of? When you land on a property and choose not to buy it, it goes up for auction to everyone immediately. Check your rules; it’s there.

    This is really a fantastic article, and illustrates good stuff. I realize my real life real estate strategy includes much of the core parts of this. While I have cash in my pocket right now, it is in the pipeline for investment, and not simply in my “Scrooge’s money bin” for swimming. 🙂

    • Greg –
      I often use that rule to pick up properties for less than the posted price — typically when everyone is short on cash. Your opponents typically catch on after you do it once or twice, but it is usually good for a foreclosure sale price!

      • Brandon Turner

        I’ve played both ways, but I do like the “Auction” style, since it is in the rules. Thanks for the comment Greg! (and too bad you don’t have Scrooge’s money pit for swimming – I’d be right over!)

        And Josh- the parallels to REI are so abundant! Thanks! 🙂

  12. I can’t believe NO ONE who commented on this mentioned the free parking money that’s not in the rules. Maybe there’s some real life parallel there too…that everyone I know and have every played with puts all the Chance, CC, Tax etc. money into a big pile in the middle of the board and whoever lands on Free Parking gets it. I’m racking my brain trying to apply this “almost everyone adds this same rule that’s not there” and continues life like it is there 🙂

    • Brain Fart…didn’t finish that thought in the form of a coherent sentence…should have read:

      I’m racking my brain trying to apply this “almost everyone adds this same rule that’s not there and continues life like it is there” idea to real life or REI. Any thoughts? Or am I stretching a bit? It’s right on the tip of my brain.

      • There are a lot of people out there that want a free ride?
        Real Estate investing isn’t a sit back and roll in the cash deal, it takes work?
        Some people want to make up rules to give themselves a big paycheck at the expense of others?

  13. I like your comparison of monopoly to real estate investing…i have noticed that there are many industries,but they all interact and deal with people..I did not know you lived in Minnesota so did I lived in the southern part..Cool!!

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