Sounds like a touch of narcissism. Of course, armchair diagnoses over the internet should always be taken with a planet-sized grain of salt. It's very difficult to determine when I can't observe his behavior in person. But I'd put money on narcissism, at least subclinical levels.

Have him do the Dark Triad test with you for fun. Tell him it's related to success in business (which it is).


Yeah, that's probably a good idea. If you have to interact with him, know where your boundaries are and enforce them calmly and firmly.