A data-driven approach to beating SAA out-of-sample

While solutions of Distributionally Robust Optimization (DRO) problems can sometimes have a higher out-of-sample expected reward than the Sample Average Approximation (SAA), there is no guarantee. In this paper, we introduce the class of Distributionally Optimistic Optimization (DOO) models, and show that it is always possible to "beat" SAA out-of-sample if we consider not just worst-case (DRO) models but also best-case (DOO) ones. We also show, however, that this comes at a cost: Optimistic solutions are more sensitive to model error than either worst-case or SAA optimizers, and hence are less robust.