When engaging in options trading, startup investments, penny stocks, and other Black Swan strategies, you can be in a situation where you most all your money 90% of the time, but 10% of the investments have a 100x return. If you pursue this risky strategy, you need to be able to hold on in the face of volatility and sky-high gains.

I wouldn't recommend this strategy to anyone who doesn't have Vulcan-level discipline over their emotions, but it is a valid investment strategy.