I think one of the worries I would have is - is this a cult, feel-good motivational-speaker sort of thing, a self-propagating meme predator attacking me?

Possibly an attempt to align your financial incentives with the students would help - for example, by offering some sort of money back if not satisfied after such-and-so period of time, or accepting student labor as payment (while still paying them at their current rate - that is, hiring them out at a higher, post-training rate).

I also think that because this is an information good (videos, software, text), you might not be able to charge what you initially might expect to be able to charge. Possibly generating content continuously, giving away a fraction of it (the oldest fraction) and charging for the cutting-edge updates could work.