This situation is sad if students are truly leaving his academy over what so far has been a "he said, she said" situation.
Roy is a tall, in-shape, decent-looking guy who has a cool job that he is successful at and probably has a few sheckles in the bank. He's well-spoken, interesting and passionate. Getting women should come pretty easily to a guy like that.
My impression is that Roy was probably very awkward and shy as a teenager/college student and didn't have much success with girls, that's why he threw himself into judo, aikido, JJJ and BJJ. You don't have 4 black belts by the time you're ~30 if you're drowning in pussy.
I think despite turning out to be a well-respected instructor and successful business man, his insecurities with women carried over into adulthood and perhaps that's why he resorted to this PUA stuff to boost his confidence. And maybe that's why he couldn't let go of being rejected by his secretary, if that's what actually happened.