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How to Never Lose Monopoly Again

by Brandon Turner on August 12, 2012 · 60 comments


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

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{ 60 comments… read them below or add one }

Eric Hempler August 12, 2012 at 8:58 am

I’ll have to try this when I play Monopoly :) Probably my favorite game.


Brandon Turner August 13, 2012 at 9:23 am

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!)


John L August 12, 2012 at 1:42 pm

Great blog with real life lessons that work. Thanks.


Brandon Turner August 13, 2012 at 9:23 am

Thanks John!


Jeff Brown August 12, 2012 at 2:44 pm

Without a doubt, your best post, Brandon.


Brandon Turner August 13, 2012 at 9:26 am

Nice to hear Jeff! Ironically, the quickest post I’d ever written, despite being almost 1500 words. Sometimes, I guess, you just get in the zone. I appreciate the encouragement! Thanks!


Joshua Dorkin August 12, 2012 at 2:50 pm

Great strategy, Brandon. I’ve had quite a few epic Monopoly matches in my day. That said, thanks for pulling in the application to real life!


Brandon Turner August 13, 2012 at 9:26 am

Someday we’ll need to play… :)


Joshua Dorkin August 13, 2012 at 9:57 am

Is there an online version or iPhone app somewhere?


Brandon Turner August 13, 2012 at 10:15 am

There is, but you lose the whole “people aspect” of the game that way :) Is there going to be another BP Summit next year? I’m foreseeing an epic late night game…

April Adams August 12, 2012 at 3:11 pm

Great analogy. I am using the Monopoly board to teach my daughter about real estate investing.


Brandon Turner August 13, 2012 at 9:27 am

That’s awesome, April! I’m sure I’ll do the same someday. Have you played the “Cashflow” game from Rich Dad Poor Dad? Also a good learning game.


Nancy P-Y August 12, 2012 at 3:33 pm

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!


Brandon Turner August 13, 2012 at 9:29 am

Ha Nancy! That’s great! ;) Your son sounds like a young real estate investor in training!


James August 12, 2012 at 4:14 pm

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 August 13, 2012 at 9:34 am

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?


Lee August 12, 2012 at 4:56 pm

There’s also that “location, location, location” thing as well. Buying all the red and orange properties gives you a statistically higher chance at winning. :-)


Brandon Turner August 13, 2012 at 9:36 am

Aha! Nice comparison to real life!

The Orange properties always hold a very special place in my heart. :)

Thanks Lee!


James August 13, 2012 at 10:26 am

Somewhere, I read that the orange properties are the most often landed on. I have always preferred the Orange properties, giving much more expensive properties up in preference for them.

Just found a link to some probabilities-

As a group, the Orange do really well- and as a plus, houses cost $50 less each than the red properties :)


Brandon Turner August 13, 2012 at 10:34 am

Wow! Someone had a lot of time on their hands! I’m gonna go take some time to digest that stuff. Thanks for the link James!

James August 13, 2012 at 10:58 am

I f you like those stats, here is one where they calculated pay-back time for the different property groups-

Yan Peters August 12, 2012 at 6:54 pm

Brandon, good post. I think I can beat you in monopoly, best of five games.


Brandon Turner August 13, 2012 at 9:37 am

You’re on! ;)

And wow, that could be a long day (unless I get multiple repeats of my 12 minute victory!)


Keith August 12, 2012 at 8:00 pm

We used to (and still do) keep a tally of what the winner and loser(s) had on the inside cover of the game, it is fun to look back!


Brandon Turner August 13, 2012 at 9:38 am

That’s a great idea! Thanks Keith!


Melodee Lucido August 13, 2012 at 2:48 am

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!


Brandon Turner August 13, 2012 at 9:40 am

Haha it’s true! She learned my secrets and used them against me! Thanks Melodee!


Mike August 13, 2012 at 7:10 am

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 August 13, 2012 at 9:42 am

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!


Mike August 13, 2012 at 10:19 am

Thanks Brandon – I gotta take a page form your post here and start blogging with cool catchy titles. Great quote by Dave Ramsey btw…so true!


Brandon Turner August 13, 2012 at 10:28 am

The catchy titles do seem to spark some interest, eh?! Keep up the good work!

David Coe August 13, 2012 at 9:08 am

Brandon, great post. I have 2 pre-teen boys that love Monopoly. I’m printing this out and adding it to the “rules”!


Brandon Turner August 13, 2012 at 10:27 am

Thanks David! It would be an interesting game if everyone followed this same strategy at the same time! I see a good financial future for your boys if they love Monopoly at a young age!


Sophia August 13, 2012 at 9:25 am

Great article!


Brandon Turner August 13, 2012 at 9:42 am

Thanks Sophia!


James August 13, 2012 at 10:12 am

@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”).


Brandon Turner August 13, 2012 at 10:17 am

That is an excellent book! A friend of mine is fond of saying “if it’s true, its not new and if it’s new, it’s not true.”


Melodee Lucido August 13, 2012 at 11:50 am

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.


Brandon Turner August 13, 2012 at 3:33 pm

No problem Melodee! Thanks for the nice comments!


Karen Rittenhouse August 13, 2012 at 12:30 pm

What a fun post.

I’ve done very well with real estate investing, but I haven’t played Monopoly. Now I’m totally intrigued about playing the game!

Thanks for the post.


Brandon Turner August 13, 2012 at 3:35 pm

Thanks Karen! And you definitely need to play! It’s a super fun game! And not just for kids either!


Kristie August 13, 2012 at 12:45 pm

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!


Brandon Turner August 13, 2012 at 4:06 pm

I love analogies too Kristie! They make life so much easier to understand for simply folk like me! Thanks for the comment and good luck beating your husband! At least you can win in bowling – my average score never tops 50!


Hamilton Hiatt August 13, 2012 at 2:16 pm

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!


Brandon Turner August 13, 2012 at 4:07 pm

I’ll check that out Hamilton! Thanks for the link!


Realtyman August 13, 2012 at 7:09 pm

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.


Brandon Turner August 13, 2012 at 7:12 pm

Definitely a great foundation! And great gift idea – I think I may do the same!


Jerry Davidson August 13, 2012 at 10:43 pm

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.


Brandon Turner August 14, 2012 at 9:54 am

I never knew that Jerry! I didn’t think the game could get any cooler in my mind – but it just did! Thanks for the info!


Greg August 14, 2012 at 11:35 am

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. :)


Joshua Dorkin August 14, 2012 at 12:28 pm

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 August 14, 2012 at 12:43 pm

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! :)


Shane August 14, 2012 at 1:42 pm

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 :)


Shane August 14, 2012 at 1:45 pm

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.


James August 14, 2012 at 2:00 pm

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?


McKellar Newsom August 21, 2012 at 8:21 pm

Hi Brandon,

I enjoyed your post! I’ll have to try a few techniques the next time my daughter wants to play. mck


Brandon Turner August 21, 2012 at 10:42 pm

Thank you McKellar! Good luck!


Andre Green September 4, 2012 at 1:55 pm

This post was great!!!! Entertaining and informative! Brandon I think your lost was well worth it. I once heard “A happy Wife equals a happy Life!”.


Jon E May 19, 2013 at 1:51 pm

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!!


Brandon Turner May 19, 2013 at 2:16 pm

Thanks Jon! Yeah, I grew up there until I was 18. Too cold for my liking!


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