Here is my take on Pythagoras' Greedy Cup. If you fill it above about 60%, it will empty itself out of the hole in the bottom. I tried my best to make the shape sneaky so people might not notice the holes until they've triggered the effect.

Side Note, does anyone know how to orient thing file default views? For me it's upright in both solidworks and meshmixer, but on it's side in the thing preview window.