This guy's actually just a jerk. Youngish, 4 kids, well off. Works in commercial real estate in the city for Cushman Wakefield where negotiating commercial tenant leases is the high art of screwing your customer and leaving them with a smile on their faces! (I know as I worked for a large NYC real estate developer for 5 years out of college and spent one year working as an assistant to his lease negotiator.)
I'm not sure he's unsophisticated but certainly not ready to have a solid, healthy relationship with his crew/captain. His last full time captain is an acquaintance of mine and their relationship ended badly.
My first interaction with this owner was a blind phone call I received in the Caribbean a few winters ago when he was just about to take delivery of his boat. He wanted to hire me sight unseen from a recommendation of a friend of his who had a 90' boat I'd been helping deliver north/south for years.
I told him then that the relationship b/t owner and captain was a pretty intimate one, based on more than just being qualified to run the boat. He didn't want to hear any of it then and now finds himself with a revolving door of boat cleaners and day captains. And though he can manage docking/undocking with no problem, not having a regular, qualified, dependable captain is going to leave him at the mercy of not having anyone at all just when he'd like to take a trip...