I think it's possible for his character. He has a lot of money (can throw it around), lives in a big city (Miami and then Hollywood, so lots of [shallow] women), nice clothes/looks/fundamentals, and also has a position of authority (owns part of the company; tells coworkers and clients what to do). I think the main problem he'd run into would be girls slotting him into the provider role, so possibly lots of resistance, but he's also got a strong bad boy vibe in this video -- which lets women know that he's not in it for a LTR. Oozes bad boy and confidence, and is a an asshole and natural leader.
Definitely possible, but still a TV show.
EDIT: Just wanted to mention that the "middle-aged" part doesn't really hurt him. If anything, that helps him. Men get better with women as they age, instead of the reverse. Also, he's middle-aged and not married with all of these things going well for him? Key sign to women that he just wants something short term.
