i’ll award bounties according to whatever @gptbrooke thinks, or my
best estimates of what she’d think if the former isn’t available.
This is a game of trying to improve your margin. Ideas like, "sell more merch" are a pain and don't actually generate as much ROI as you think, but they do build a community identity. Others, like "get a cool shiny badge on our Discord (or whatever you have) for $8 a month" are much better margin and scale well.
I also think that you should consider a very few sponsors, done tastefully, and firewalled off to contexts where that makes the most sense (e.g., fireside chats).
(Just throwing out an idea — not sure if it would work or fits Brooke's vision!)
Turn it into a subscription club, e.g. $100 per month
Make membership exclusive: there's an application, and set the bar at whether that person would be interesting to talk to and not scare people etc. (You could use a prediction market on whose application will be approved, with public applications accessible via a link! That's how I would do it, at least.)
Host more regular events and meetups. Let members propose and host events for each other.
Kind of like a more online version of The Commons.