I just finished reading "Free: The Future of a Radical Price" by Chris Anderson. As it happens, Anderson isn't the "wild eyed" price anarchist that a lot of people portray him as; consider this, near the end of the book:
People will pay to save time. People will pay to lower risk. People will pay for things they love. People will pay for status. People will pay if you make them (once they're hooked). There are countless ways to make money around Free. Free opens doors, reaching new consumers. It doesn't mean that you can't charge some of them.
I think that last bit is the key to understanding his whole view on this: what Anderson is talking about with free is digital goods, and that instantaneous, perfect copying makes free the natural floor for a lot of things that weren't free before. That doesn't mean you can't charge; it simply means you have to find a way to charge that adds value. I'll be thinking about this book a lot...
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free, freemium, long tail