Many years ago, I terribly overfit a model which caused losses of a lot of shekels (a LOT). It’s not that I wasn’t aware of the potential overfitting. I was. Among other things, I used several bootstrapping simulations. It turns out that I applied the bootstrapping in a wrong way. My particular problem was that I “forgot” about confounding parameters and that I “forgot” that peeping into the future is a bad thing.
Anyhow, Yanir Seroussi, my coworker data scientist, gave a very good talk on bootstrapping.