Matt Mason's The Pirate's Dilemma: How Youth Culture is Changing Capitalism is itself a bit of a dilemma. It's about a couple of important issues: the challenges of piracy, the evolution of intellectual property, the impact of open source models on traditional product development strategies, and the changing nature of consumerism. It has a good common-sense message: pirates exist because they fill needs that the market isn't meeting, so instead of trying to legislate them out of existence, maybe try competeing with them to expand the market. Especially at the end, Mason really has some interesting insights on the cultural role of hip-hop and why it has endured when other countercultures have failed.
At the same time, as I was reading some of the chapters, I could almost hear Johnny Rotten muttering his famous question, "ever get the feeling you've been swindled?" It might be overstating things to say that Mason has an agenda in the book, but he definitely has a strong perspective, which is vindicating the subcultures that he likes and finds cool (hip-hop, punk, disco) in the eyes of mainstream capitalism. I'm a fan of subcultures as well, and I recognize the interesting ways they interact with the mainstream. But in focusing so much on the internal dynamics of the subcultures themselves, Mason seems to ignore the reasons they are (or were) "sub" in the first place - which is really a question about the mass culture.
Mainstream companies and institutions have a hard time incorporating the contributions of pirates and outsiders because mass culture is fundamentally imitative and conformist. The whole reason that pirates and punks are on the outside looking in is because there are never enough of them in any given society to define the values and set the agenda. It's one thing to make the (admitedly provocative) point that graphiti and outdoor advertising are two sides of the same coin; it's folly to suggest that mass culture will ever acknolwedge them as equally (il)legitimate.
The other problem is more fundamental. Even within subcultures, there is an elite level that is doing interesting and socially-valuable work, and a wide base that is going along for the ride. A few graphitists are genuine artists; most are mindless vandals. A few pirates are appropriating intellectual property for the purpose of finding new ideas in the process of remixing sampels; millions more are just getting content for free instead of paying for it. You can't really define the Pirate's Dilemma merely by focusing on benefits produced by the pirate elite, without more than a glancing acknolwedgement of the social costs of piracy in its wider dimensions.
Mason is a self-identified member of at least a few subcultures. He probably knows as well as anyone about the divide that exists in any population between the creative leaders and the mass of me-toos. Because he is so interested in selling the benefits of disparaged subcultures in a context that is intelligible to capitalism and a business audience, he can't really get into that. He doesn't want to air dirty laundry in front of the invited guests. Consequently, his analysis sometimes raises more questions that it answers and dodges troublesome issues by moving on to the next topic.
In balance, I enjoyed Pirate's Dilemma, particularly because of its strong conclusion. Nevertheless, I am left with the sneaking suspicion that Mason himself is more interesting than his book.