The iPhone/iPod Touch is a fascinating device for kids. It is so intuitive that it is a bit addictive. While I would never suggest that Sammy should replace reading, studying, sports, play, family or music time with iPhone time, I have watched Sammy become a good Scrabble player, better at speed math (through the “PopMath” app) and now learn a bit about risk taking and portfolio benefits through his playing Monopoly (mostly when stuck on a subway, waiting in a line or waiting for a movie etc.).
We started playing the “pass & play” version about a month ago. Sammy quickly developed strategies that were consistent with a basic understanding of ROI. In our first game he recognized that the last property (clockwise) in a Monopoly had the best ROI on a house or hotel. Those properties get higher rent for the same price of the house.
In later games he had started to understand the risk/reward benefits of leverage – he began actively mortgaging some properties in order to be able to opportunistically acquire the positions on the board that he wanted. Sometimes this worked out for him, sometimes he stretched too thin and a modest setback (landing on Income Tax) could lead to selling of houses or other bad outcomes. At least in the game of Monopoly, he seems to have become comfortable with taking some risk without being reckless (mortgage everything to acquire anything).
What was truly fascinating to watch was how he learned about diversification over the course of a bunch of games played. In one of our first games, he fought hard and “overpaid” in trades to acquire Boardwalk and Park Place – giving up several other properties that gave me monopolies elsewhere. He took all of his cash, some of it “borrowed” and built until he had a hotel on each property. I had the very unlikely luck to land on Boardwalk on 2 consecutive orbits of the board and lost (Monopoly Probabilities). Based on how he played games after that point it seems he thought he had found a dominant strategy for the game.
Since that game, he has not been so lucky (or I have been luckier?). He tried the same thing, overpaying for the Boardwalk monopoly but he consistently would run out of money before I would land on that super expensive property. I have watched him grow wiser with play. He is still a big fan of the Boardwalk monopoly and the green monopoly and will bet on the low probability, high reward outcome – but he definitely gets that spreading himself out, not giving up monopolies and placing more bets wins more games.
I think this is a great example of how technology can drive learning. Anyone who played monopoly could have internalized these learnings pretty quickly, but when you actually need to sit down at a board and play an uninterrupted game, you just don’t play that many games. It has been the ease of play and frequency of games that has taught Sammy these concepts.

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Great observation! I, too, let my daughter, who is 6 and in the first grade, play on my iPhone when we’re waiting at a restaurant, at the grocery store, etc. She mostly plays math games, hangman, and scramble.
In her school they have weekly timed math tests of 100 problems, addition and subtraction. In 6 weeks of playing on the iphone app she has gone from taking 15 minutes to complete 100 problems with 5+ errors (and being near last in the class) to finishing in 5 mins or less with no errors — almost always the best in class. And she loves it!
We play Monopoly sometimes. She’s a little young for some of the complex understandings that Sammy has exhibited, but she has displayed a preference for obtaining all the railroads early using that to keep other players from having the cash to erect houses and hotels. I’m surprised at how well that strategy has worked for her.
The handheld technology market is full of mindless time fillers for kids. But sneaking in a little parental interaction and education seems a better way to go.