Try gambling (say, poker) with the ultra rich. They don't really give a shit win or lose because they like the entertainment, but they _absolutely hate_ to lose to someone who needs the money. For one, that money is never coming back to the table for them to win back later, and two, that person was playing for completely different stakes as the rest of the table and actually "got over" on them.

If you even want to get into such games, having the money isn't enough. You need the aura that it's small stakes to you. Multiple cash game hustlers have written about this phenomenon.