The Standard Model (SM) of particle physics is a spectacularly successful theory that is known to be fundamentally incomplete. The discovery of the Higgs boson at the Large Hadron Collider is, on one hand, the final missing piece of the SM and, on the other, a window into what lies beyond. Processes involving pairs of Higgs bosons are a sensitive probe of new physics and will ultimately allow the shape of the (in)famous Higgs potential to be directly explored experimentally. I will discuss the motivations and experimental challenges of searching for Di-Higgs production at the LHC. Emphasis will be placed on a new method -- using synthetic data samples -- to overcome one of the most important experimental limitations: systematic uncertainties in data-driven background predictions.