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In relation to the content of the original post, I don't consider the flaws of value for value fatal. Value for value, a media content business model he developed on his No Agenda podcast, requires not just refusal of advertiser money, and asking the audience for money, but also dedicating a portion of the show to thanking the "producers" for their contribution.
I don't have much to say regarding the tech behind all this. I understand why Adam would want paid messages to stay private, and to differentiate paid messages from cross platform commenting.
On another hand, I recognize the difficulty of relying on the audience for income, but many people have done so for a while now quite successfully and can serve as potential archetypes of how to do it. The patreon model approximates value for value, but in setting a price for the audience the content creator may potentially artifically limit their income.
Full disclosure, I listen to various Adam Curry podcasts, including Podcasting 2.0.