What Entrepreneurs And Monopoly Have In Common

I strongly believe in the idea that we can learn from even the most trivial of things and a little pondering over small matters can lead to great understandings and moments of epiphany. There is one such thing which in my opinion is great and one can infer great things from it, and that is Monopoly – The game.

Everyone has played one or several versions of monopoly at one point or another in our life. It is one of the great family games for passing time and enjoying quality time with family members. However, if viewed from a different angle, a monopoly actually has some attributes that can be applied on a successful entrepreneur. In other words, there are some things that monopoly and successful entrepreneurs have in common. I’ll discuss them briefly in the lines below.

What A Successful Entrepreneur And Monopoly Have In Common

Take Risks Early:

In a monopoly, in order to own the most property in the set before the game ends the player buys property early and takes risk earlier. This is the same thing, which successful entrepreneurs do, they realize the situation of the market, and when it comes to investing or jumping in the market, they do it when the niche is fresh and new. Thus, thus monopoly approach of successful entrepreneurs benefits them greatly in the long run.

Negotiation Skills Are Important:

The other important tactic required to play Monopoly is a negotiation. There comes a time in Monopoly where in order to move forward and lead the game, you have to negotiate a trade with the other players. There are times when the players are not willing to part from their wealth, therefore, at that point of time the player has to come with convincing arguments and maneuver the resources in such a way that an attractive deal is offered to the other players which persuade them in finalizing the trade. This is the same thing, which entrepreneurs do when it comes to either convincing the capitalists or clients regarding their business. Thus, by using their negotiating skills successful entrepreneurs persuade others into joining hands with them.


In Monopoly, the more diversified your property is the more chances and sources of revenue with little chances of failing in case some investment does not payout. Similarly, all the successful entrepreneurs diversify. They don’t stick with a single idea and give their all to it, rather they diversify and find potential in other areas as well, which helps them stay safe and avoid the sudden uncertainty that is always there when one keeps all the eggs in one basket.

Money In Backup Is Necessary:

In Monopoly, in order to survive all the penalties, the jail trips, the taxes, and other uncertain popups, the player has to have money in the backup. It is the same strategy adopted by all successful entrepreneurs. No matter how good an opportunity seems for an all-out investment, or how little revenue they are generating from the business, the entrepreneurs always keep money in the backup to deal with any uncertain or unwanted situation.

Entreprenuers and Monopoly Have In Common

Understanding ROI:

The one thing that the player of Monopoly has to be an expert in order to be successful in the game understands of ROI. The player must know the kind of investment he is making and the kind of return that is expected of the investment. Thus, it is the return on the investment that makes the whole game run. Similarly, successful entrepreneurs are also good at understanding ROI, and every investment they make shows their skillfulness pertaining to the concept of ROI.

Now it’s Your Turn!

Have you been a Monopoly player? What do you think are the strengths of the game? How does it relate to entrepreneurship? What have you learned from Monopoly or any other game? Please share your thoughts in the comments section below.

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27 responses to “What Entrepreneurs And Monopoly Have In Common”

  1. Arleen says:

    Hi Nate- I played Monopoly as a child and now with my grandson. I find that I will take the risk right off and start buying. I do the same thing in my business. I do things head on and do not wait for it to come to me. It works for me when I do not have tunnel vision. I run a very successful promotional products business, but I am very aware of my competitors. If you do not keep up with times you will be left in the dust.I have spent alot of money for my web developer to change the look and feel of my website. This is a massive undertaking as I have over 7000 products on my site. Being an internet business you are a mouse click away from the next competitor.

    It is important to get feedback from your customers about their experience. Another good place to improve.

  2. Emmanuel says:

    I have played the monopoly game before though but I think I will do better if I should try since I already possess the mind of an entrepreneur. Hahaha!

    Thanks for sharing with us this insight.

  3. Brian Meehan says:

    It’s been quite a while since I played monopoly, but I love the game. Yes there are quite a few lessons to be learned.

    Enjoyed the post. Thanks for sharing.

  4. Allyson says:

    I actually hate monopoly and will not play it. I was a terrible terrible player. Ironic that I love being an entrepreneur! You drew some great parallels.

  5. Krystle says:

    I do find myself as a monopoly player. I do take risks early, but I have to negotiate my skills. Practice makes perfect. LOL! 🙂

  6. katherine says:

    These are great tips for anyone!

  7. Matt Ritchey says:

    I haven’t played Monopoly for years, but I can see the correlation!
    I play a lot of games where self expression and creativity is involved, such as Taboo, Pictionary or Cranium.

  8. John Engle says:

    Hey Nate,

    This is a great analogy for life and finances in general.

    A few months ago I read the book by Robert Kiyosaki ~ ‘Rich Dad Poor Dad’, to where he made a comment in the book that said that schools do not prepare kids for financial wisdom.

    Donald Trump in his book ‘Think Big and Kick Ass’ said virtually the same thing… the point that I am trying to make is that maybe we need to incorporate Monopoly into schools, because you made it a great point that there is a parallel between Monopoly and financial know-how.

    Great Article…

    John Engle

  9. Nate, great post, love the comparison and very accurate. After all monopoly is an entrepreneurs thing either as the game or in life. As always you need to follow through on your beliefs and not be discouraged.

  10. Misty Spears says:

    These are all great tips Nate! I have one more for you. When I was a kid, I always went big! I would sacrifice everything I had to get to the big one faster (Park Place and Boardwalk). I think that’s a good way to run my businesses now too…go big or go home! lol

  11. Bonnie Gean says:

    Since I am not a monopoly player, I will have to take your word that it’s similar to being in business. 🙂

    However, I can attest to the “backup” money as a necessity. You need to take the earnings and reinvest them back into your business to help it grow.

  12. Shari says:

    I love this Nate – My son and I have been playing a game of monopoly for the last two days. . and it’s fun to watch him learn these lessons. I was just thinking last night what valuable lessons the game can teach so it was fun to read this! Always love your posts

  13. Lynn says:

    I have learned NOT to play Monopoly with my 11 year old granddaughter – she is ruthless!

  14. Melissa says:

    I love how you were able to correlate the two, and I can see how they apply.

  15. I don’t play games because am always occupied all the time….. Nice post..

  16. Another great post, Nate! When I was growing up in the 50’s and 60’s, Monopoly was one of the most popular games – everyone played it. When I got married, I married someone who played it all the time in his childhood and would have marathon, days long sessions with his cousins. When we had a son we played Monopoly with him (of course). We each had our style – I would ignore the lower priced properties for Park Place/Boardwalk, my husband would try to get hold of all the railroad properties and utilities and my son would start building houses the instant he could. None of us became entrepreneurs but I think the game taught us a lot of valuable lessons – patience, planning, the (sometimes) importance of luck, and being both a humble winner and a good loser.

  17. I play First To a Million (Monopoly) with my kids. It’s fun and they get to see that being an entrepreneur can be fun.

  18. elena stasik says:

    Very Interesting! Thanks Nate!

  19. Jeanne Melanson says:

    Oh wow! What an interesting concept, and one that I had never thought of before! Of course, you’re right! You are playing the part of an entrepreneur when you play the game. You buy early, plan your moves, keep enough money to keep you going, and try to stay out of Jail. 🙂 Thanks for your insight, Nate! That’s cool.

  20. YES, YES, YES…

    Back in the day – before going to University – used to play Monopoly with my parents, but mostly for the fun of holding and counting the money as a banker. Never knew there were strategies (it was before the internet and google).

    Another similar board game that I played with my son was Robert Kiyosaki’s “Cash Flow”. Have you experience with that, too?


  21. Clara says:

    In many ways risk and opportunity are the same thing. Monopoly will definitely bring out your inner entrepreneur.

  22. Ryan Biddulph says:

    Take risks – i.e. give yourself chances – early and often! Love it Nate, because Monopoly and your analogies are the perfect business lesson. I tweak my strategy each day; I just filmed 3 videos in the past 5 minutes and will upload those bad boys in a bit….tweaking, changing, publishing content at different times, listening to my intuitive nudges.Thanks again my man!

  23. Hi Nate,

    What a great analogy. I often think of Monopoly when thinking of business too. It is something we learn as kids playing this game.
    I never wanted to buy Park Place or Broadway. Instead, I diversified my properties then made them more valuable by building hotels.

    I wanted to have things spread around…not all my eggs in one basket. I also kept a money reserve because you can loose the game if you don’t have the cash!

    So, as a kid I learned how to use money effectively. I always won the game so no other kids wanted to play with me lol.

    It is the same with entrepreneurship. When I was buying real estate, it was just like Monopoly. I didn’t sink my money into a McMansion, rather purchased small bread and butter houses, rented and then flipped.

    I always thought of Monopoly in the real estate game….and still do.

    Now, as a marketer on the internet, that is one piece of the pie. Need to have a diversified income too. Ergo….I haven’t had to work a job in many many years.

    Fun post!


  24. Sonia says:

    Loved this post Nate!

    I will be more mindful of those that I play Monopoly with 🙂

    I have always been one to buy up as much ‘Real Estate’ as possible while my kids look on in horror as I get down to my last $500 before I start to make anything! But I usually end up winning!

    Thanks heap, I thoroughly enjoyed this post.

  25. Esha says:

    Omg, this is so good, Nate! The distinction between the two are so true.

  26. Christine says:

    Thanks for sharing this Nate. Monopoly is such a educational game. You really do need to make risks early if you want things to get growing quick. And you never know what will happen — but that’s the fun part!

  27. Sophie Bowns says:

    Thanks for the interesting tips Nate 🙂

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