Helping a Chess Grandmaster Build Recurring Income (Need Guidance)

I came upon opportunity to implement something a'la Sunday Recurring Income Play

https://www.skool.com/ronin/sunday-recurring-income-play

My friend's brother is a Chess Grand Master (he's doing it full time) and my friend connected us, because heard that his brother wants to start his paid Skool Community to have steady income stream and I told my friend some ideas that I learned here inside Royalty Ronin, so he connected the two dots.

What I'm looking for is a little bit of guidence/clarity on how to tackle it.

Situation right now:

-he has published books, online courses, did 1:1 chess coaching/tutoring

-tired of having irregular income (thats why he wants to start paid community)

-doesn't have any SM following

-doesn't have email list/fb group/email addresses of buyers of his stuff (published through 3rd party and they have this data)

-great reviews from buyers/customers (he know what he's doing - one of the best player in our country and he coached/helped people become champions in their cities/countries)

My questions:

1)How to seed group in this case? I thought that to seed the community we could give a free trial to his current and previous coaching students/buyers. I even thought of using this as an Unannounced Bonus, something like "I'm thinking about creating a chess community. Bought any of my books/courses/1:1 coaching? You're entitled to the free 30days trial, just send me an email with title "community" and a receipt and my team will get back to you with details"

2)Go with free + paid community or focus only on paid one?

3)Which materials from this group could be helpful in this case? I got Hopper Millions, STM, BAD, Audience Multiplier on my radar but it's a little overwhelming in Travis World with all the tools that are available so I'm stressed that I can miss the right one for this job :D

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