Buy, Sell, Dream and Scheme! Lessons for business by playing and winning Monopoly

Some people are good at Monopoly; the same people who don’t see it as ‘just a game of chance’. They also tend to be the only family members that enjoy it (strange that, eh?).

Ok. Sure. I admit Luck has something to do with it. But as is the case in business, luck won’t see you through everything – you must make the right moves. What are often the right moves to make in a game of Monopoly? How might these relate to your business?

  • Appropriate Levels of Debt: (Hold back others as you empire build)

    And you’re off…game started. You’re buying everything you can (the right move): speculating sets, blocking others, generally laying the foundation against the competition. Problem is – that can’t last forever – you only start the game with £1,500. You’re not going to see decent cash flow coming in until maybe your 7th or 8th time around the board. What do you need? Debt! What’s the smart play? MORTGAGE the “blockers” that you don’t need and only bought to wind up your older brother. You still own them when mortgaged, so release the cash, keep the other players stuck and focus on building your own competitive advantage by building houses and hotels where you want and need them.
  • Lesson for business: Debt is often viewed as a ‘bad thing’ to have but that’s not always the case – sometimes it’s exactly the fuel you need to bring about success. You should weigh up the costs of debt against the cost of growing slowly – debt can accelerate your growth if the proceeds are spent wisely.
  • Stations are the track to success (Death by many cuts):
    Some of the best threats to your competition are the small things – players don’t fear railways in the same way they do a massive great hotel on Mayfair. Stations are a nice cash-cow.

    1. Own all 4, and you’ll yield 25% return from a single land
    2. Your opponent is NEVER more than 1 roll of the dice away from these silent killers (10 spaces between each, nicely spaced out)
    3. You won’t bankrupt Dad on a single land, but each time he appears you’ll weaken his reserves in a way that no other property type can

Lesson for business: Steady cashflow is a great thing to have. Regular repeat business from loyal customers spending little and often, quickly adds up. Identify your cash-cow product or service, nurture it, then watch your returns.

  • Time spent in “The Big House”
    Early doors, keep out of jail. There’s a lot to play for at start of the game and negligible risk until properties get bought up and buildings start going up. Don’t waste time in jail until you’ve achieved your first colour set. Once the board’s been bought up… get yourself tucked away in Jail as much as possible. Cash still comes in, but you don’t put any out!Lesson for business: sometimes its OK to “do nothing”, but you have to plan to do it. Work the risk that’s in front of you.


  • Lucky 7’s 

Mathematicians amongst you will know that the most commonly rolled number on a set of dice is a 7 (most permutations). How does that help you? Well, the novices in the room will focus on what it means for them (e.g. “If I roll a seven I’ll land on that space I’ve wanted”). The tacticians will play the board. Your turn is 50% about rolling the dice, 50% about planning for how other’s will roll next. If your opponent is anywhere between 6 and 8 spaces from a group of your properties, there’s a 45% chance they’ll land on one of them. The smart player would build a house there and then, setting a well-placed trap.

Lesson for business: look externally, consider your own next move, but not in isolation. The relative success/failure of your strategy depends on what others are doing (or not doing!).

4 ways to defeat the family at monopoly and 4 worthwhile lessons to think about for your business.

Remember. At home, success at monopoly isn’t really winning, it’s getting through the game without making anyone cry.

Paul Bready
About the author

Paul joined Craig Corporate in 2016 and has been involved in various diligence, fund raising and financial modelling assignments. Paul qualified as a Chartered Accountant (ICAS)...
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by Paul Bready