The problem is that there is simply way too many people wanting way too much money for stuff. Everybody that has a business model that includes startups is doing some kind of Chinese Math that begins with "if we can take 1 million startups and help them make 50K per year, and then we only ask for 20% of their profit in return...."
The problem is that most startups fail, even with the super-awesome help you are providing. That means there's no money for anything. There are far too many companies selling the dream of doing X instead of X itself. So yes, I can provide you with a master class on product positioning, and hell, at the end of the day you can even feel like you've learned something and took lots of action items, but did I actually help you position your product? Or just give you stuff to do in the "product position" space? Acceptance critera has to be either "this mandatory overhead" or "this directly generated X amount of sales". That's it. Leads don't count (unless you've established a pipeline and can demonstrate it works). Being pleased with content -- even having a great feeling after consuming content and picking up things you feel are really useful -- doesn't count.
Like I said, I'm not trying to knock Andrew. For the few interviews I've seen, he's doing a bang-up job, and if the issue is just what to pay for quality entertainment, I'd much rather pay 20 bucks a month for that kind of content than something silly like a cable movie channel. I'm just saying that over a period of years I have grown exceptionally careful about spending money on anything. It's way too easy to spend more for stuff than you'll ever make back.
Want to know where I feel like I've picked up the most value? Serendipity. Some guy posts a random link on HN. I'm doing a Google search on one thing and come across something else. Those kinds of things only happen once every year or two for me. If I had my way I'd make a big house and invite the top 100 scrappy entrepreneurs to live there while I just hung out. Now that would be worth making a sacrifice and taking a gamble. Once again, this has nothing to do with this particular offer. Some kinds of information transfer work best in an interview/publish-subscribe format. Some work best in a P2P, informal, indirect setting. To me at least, important startup lessons seem to fall into the second category.