Naive or unaware Pokémon don't usually catch on to what seemingly-friendly Royce is doing when he talks to you. The truth is, he's always evaluating whether or not you still intend to spend, trying to figure out whether it's time to call in special aid or not (and what this means is not quite clear). He has many friends that help... relieve those who've gone bankrupt of their money. If you've gone on a big enough win streak, you'll definitely call his attention one way or another.