58 business lessons from a crappy online Monopoly game

Several years ago, before I met my wife, I played a cheesy online monopoly game from time to time. It always got me thinking about all of the business skills that can be learned from playing the game.

They are as follows…

1. You have to roll the dice to play.

2. If you don’t act quickly you’ll get kicked out of the game, you have to pay attention to whose turn it is.

3. Luck is a big part of the game and fortunes change quick.

4. The first person to get a monopoly can dictate the game.

5. Being nice to competitors is the best strategy to ensure quality negotiations, pissing off the competitors is not helpful.

6. Friends can team up. Alliances are powerful.

7. You have to know the rules to know what’s going on.

8. Experience playing the game teaches you subtle tricks that come in handy throughout the game and later games.

9. An overly ambitious, offensive offer can ruin later negotiations.

10. Nickel and dimes aren’t nearly as important as the big deals. A little money here and there rarely breaks the bank. It’s the big deals and the big decisions that make or break you.

11. On the other hand, tons of small payments add up.

12. You have to think up a trade that will mutually benefit the both of you. Worrying only about how you’ll benefit from a deal isn’t a good strategy. Think of the opposite side of the deal, what do they want? How can you fulfill their desire and yours creatively?

13. To make a successful deal with someone, sometimes it’s advantageous to work side deals to set up the proper chess pieces to complete the main deal.

14. Forced interruptions, in the game’s case, video advertisements, in real life’s case anything, will occur, you will get sidetracked and there’s nothing you can do about it. Patiently wait for the game to continue. Sometimes competiors will lose patience and leave out of frustration or bordem.

15. Sometimes you’ll get sidetracked with email, or life, or other games and lose focus or get kicked out of the game completely.

16. A trade that leaves the other person with a monopoly and you with a lot of cash without a solid plan to get a monopoly is a bad deal, regardless of the purchase price. You will end up giving the cash back later and be left with nothing.

17. All cash and no assets and you’re fucked. All assets and no cash and your fucked too. You gotta work out a deal that maintains both. A lot of both and you’ll win the game.

18. Sometimes you’ve gotta sell superflous assets to raise money to finance the good ones.

19. Players respect a property more than cold hard cash, with a property you can spin off cash, cash just sits there. A player with all cash will slowly lose everything. If you have a lot of profit centers you’ll eventually earn money and buy up other properties.

20. When players are desperate to stay in the game they’ll make desperate decisions.

21. When players are down and out they’ll sell for nothing.

22. Players with tons of excess cash can make deals much easier than someone with a comparable net worth all invested in properties/assets.

23. Hanging around pays off, sometimes players have a slow connection or get sidetracked and leave the game. They’ll never win. Sometimes simply sticking around ends up winning the game by default.

24. The most expensive properties are overrated. Boardwalk is expensive, and expensive to get earning money. It’s buying the cheap properties that usually wins the game. The cheap properties are often cheap to build into something quickly profitable. Allowing you to quickly grow/invest in other deals.

25. Sometimes an expensive property’s greatest strength is its overrated value, the perceived value of an asset can be as useful as its actual value when horse trading.

26. A popular property that several players want, leads to ludicrous, irrational deals.

27. Every once in a while (passing Go) you’ll get a chunk of cash for no reason. Use it to buy up assets that can earn money later, or pay off debts.

28. Buy up properties you know your competitors want, then sell it to them at a profit, negotiate for something you desire, or hang onto it to keep it out of their hands.

29. Playing against computers (or people) who use rigid algorithms leave them susceptible to strange biases which are easy to exploit. A human vs 3 computers will win almost every time.

30. Once you have some good properties, cash starts to grow exponentially.

31. You’ll get out of a pickle (jail) quicker by paying your way out rather than relying on luck (rolling doubles) to fix it.

32. A dominating player, in a dominating position, gets the other players to give up.

33. Sometimes you’ll just buy up assets to keep them from your competitors. This technique can sometimes force them out of the game allowing you to buy up all of their assets on the cheap.

34. Sometimes luck will completely ruin you.

35. Sometimes luck will hand you the victory.

36. Praying and wishing for the right dice won’t help.

37. Taxes are a part of the game, and everyone pays ‘em.

38. New players can show up to the game unexpectedly, in online monopoly’s case, new players can randomly replace old players.

39. It’s more costly to sell assets to a bank and buy them back than raise capital, or use free cash flow.

40 Debt/leverage magnifies the situation both good and bad. You can mortgage all your properties and put all the money into hotels but if no one lands on the hotels and you land on someone else’s in the mean time, you’re in trouble.

41. When dealing with the possibility of needing a lot of cash i.e rolling close to someones numerous houses or hotels, role first, see how the cards fall and then make your deal. Often times a player will buy up tons of assets, chase a strategy, overpay and spend all their money and then roll and end up on a competiors property owing him/her tons of money, which moments before they just had, but spent. Plan accordingly. Don’t make a deal with cash you might quickly need.

42. Some properties have more spaces than others. There’s a statistical advantage to assets which enable you to collect money from greater amounts of people, a lower rent/charge is acceptable. Few spaces should have higher margins. Of course the assets with few spaces that reach less people have an advantage in that they’re often easier to start/acquire.

43. Sometimes the players with a weak start, negotiate and deal their way to the top.

44. Sometimes the players with the best assets at the start lose everything through poor deal making and bad decisions.

45. Selling your assets early in the game rarely works. It’s best to see the game take shape and trade with purpose and strategy.

46. Acquiring assets early in the game before their value is apparent is smart to do if you’re able.

47. Your best asset can end up falling into your competitors hands and vice-a-versa.

48. A focused plan of attack is superior to a general one. Roam around the board on auto pilot and you’ll lose the game.

49. If you play the game too much you’ll have no social life.

50. Reality rarely goes according to plan, often it’s necessary to change tactics, mid play, based on new developments. Pivot if the situation calls for it.

51. Getting emotional about a particular property and trying to win with that asset can be detrimental. You should flow with the game and react according to the situation you’re dealt.

52. Each new game has it’s own chess pieces and alliances.

53. The game’s been played longer than you’ve been alive.

54. Sometimes you’ll win with a completely different asset than you thought you would.

55. The earlier you get into a hot property the cheaper.

56. Starting first is overrated.

57. The points (or other superfluous metrics) don’t matter except to your ego.

58. It’s a game and it’s supposed to be fun.