I have a whole different impression:
I don't think Jon is involved at all in what the Experience does or does not. I think it's one of those "projects" he allowed Matt to do so that his scallawag-brother has something to do and maybe earn some bucks with it. So every once in a while Matt asks Jon to get in front of a camera, read some lines or watch some old YT clips. That's why he's always that ecstatic with his "wows" and "hmms".
And right after Matt has released some of Jon's videos with new promises, Jon's legal team comes around saying "Wait Matt, you can't do it that way".

By saying that, this doesn't excuse Jon in any way. But I think he just don't cares at all about that project. It's a friendly turn to his brother, just like Backstage was more or less a friendly turn to his mother.