There must be money to be made from rich guys who lack game.
Forget teaching them game. Just set up the situations that will get them laid with pretty non pro women.
Hire professional male flirts to screen for girls on dating sites. Fly them out to parties that the rich man hosts in his well appointed digs, with private bands or a hidden DJ, and a little burlesque stage entertainment. Perhaps a social co-ordinator would facilitate party games. Have a few obsequious burly men in suits and ear pieces standing around as his personal security. Prepare him for the event with fashion consultants, make up artists and hair dressers. Hire hot actresses to play being sexually interested in him, and talk him up to the prospects. Have a professional wing man talk him up and keep him in the loop of the conversation. Have drugs and booze on hand. Have him take the girl away from his party to try out his private gun range, where they are briefly interrupted by the hottest actress at the party putting the moves on him.
It isn’t that money can’t by itself get you laid with hot women who are romantically interested in you. It’s that you can’t just spend it on a house and car upgrade. You have to put it to work to get you social access and status and social proof.
I’m sure there are rich guys willing to spend 10 grand a pop per night for such services. They spend it now on escorts. An entrepreneur would only need to set-up connections in the catering, acting, and modelling industries, and hire a few skilled online dating word smiths and event promoters to screen and bring in the prospects. How to market to the right clientelle would be the challenge, but once word of mouth spread in the right social circles, you’d be set. Great little business for the active player – working with all that hot talent.