I personally would pay for it but I think it's a great idea for your friend. Human contact is important for good health and long life even if it's just someone willing to listen. If there is no one to have that sort of contact with, and your friend enjoys Jeff's conversation then there's certainly no harm to it.
It seems no different than the contact we have here online but online is free and participants are here because we want to be and not for the money. But either way, it keeps our mind sharper, makes us laugh, we learn something, we care and are cared about, and we're good listeners for the most part. Sometimes we just need someone to listen.