Hi there – it sounds like you’ve got a great community going and your generosity has brought a lot of mana and new customers your way. Awesome! I agree with comments above about having an ask – openly, transparently and with some storytelling aspect. I would err away from being repetitive with the comms that can run the risk of being annoying and switching people off. Do it once, do it well, with grace. I also agree with John’s comments on creating a tiered value offering. This is really smart – it not only gives you ways to upsell people to a paid offering, but it provides choice and encourages a deeper connection. They key for me is to gather insight to inform what you offer and how you charge. Find out who’s doing what, how long they’re connected in (are they staying for the duration of classes, or signing off half way through?), and most importantly are they an existing or new member. Map out each type of person as a customer segment and work out what UX (offering, pricing) that’s right for each. Test => learn => refine. Rinse and repeat.
Go well