1) What charging model drives the most quality and response from readers? (This seems to be the crux of the argument from your blog)
2) How do I, as a startup founder, get the most from the internet and how do you fit into the picture? If I have to pay for material, why would your material be any better than, say, a few books, free videos, or making friends with other cofounders on a place like HN?
It very well may be that you had 6,900 viewers of the PG interview, but here's the dirty little secret nobody talks about enough over here: there's about 500 tire-kicker, wannabe entrepreneurs for every real one. Probably a lot more. So your "audience" is probably largely consisting of people who like learning as much as they can without actually doing very much. The get a certain cachet out of participating in your interviews.
If that's the case, then I say target those people: work towards more and more famous people and more and more quasi-in-depth interviews. Charge for older material. Set up a "Gold Ring" Entrepreneurs Circle or some other premium brand. This puts you in the startup media business, just like book sellers or the pay-for-feedback guys.
However from my end I think we'll part ways here, at least as far as your paid service goes. Startups have about a thousand different facets and I need to know just enough about each of them but not too much. That means I need instantaneous feedback and a conversation, not an hour-long video from famous person X on how tough it was ten years ago to make their first million. That works great for mass media, but I need to know how to roll out a beta of a social networking site on a limited budget. I need to be able to ask questions about specifics around this topic and I need to know it within the next couple of hours. HN gives me that immediate feedback, and as the amount of material on HN grows, I get all sorts of historical information in easily-searched text format without having to pay anything at all.
Hope that makes some sense to you.