Hi @abran I’m really sorry for the delay in getting back to you on this!
It’s possible to set up a Zap that would share the link to a video, so that would work if you had a private YouTube video for example - you could share the link so that people could go and view it. What you wouldn’t be able to do with that is to stop people from sharing that link with others. In other words, it wouldn’t be a link that’s specific to them only.
The only way that I can think to do this with Zapier would be if you put the video onto a learning platform like Teachable or Lessonly, and then created a new user and assigned that lesson to them. This would definitely work from a workflow point of view, but you’d likely need to create a paid account with whichever service you use to host the video.
Your first attempt sounds pretty close to this
My first attempt was to accept the payment via checkout on Squarespace and then zap customers to our private community page with videos.
Was there a reason that didn’t work? Where are your community pages held (on a website/forum software/etc) and how do you add new members?