Years ago, I started asking questions that seemed like gambling to help understand how others viewed risk. I would ask, "If I offered you the chance to flip a fair coin, but I'd put up $2 and you'd only have to put up $1, would you play?" And then the follow on questions had to do with how much money and the nature of the bets, e.g. one taker said he'd like to bring $100, but make $10 bets, figuring that was the fastest path to wealth. As long as he won 1/3 of the flips, he'd at least break even.
I spent some more time tinkering with this idea, until I read "The Intelligent Asset Allocator" by William Bernstein who introduced the spin on this which was for me the 'missing link'. Instead of having a coin flip represent a gain of $2 or loss of $1, he suggests the gain as return of 30% and loss of 10%.
This was the difference between a purely hypothetical question, and something that more accurately reflect the stock market.
Let's look at the outcomes for one coin;