The Pirate's Dilemma, By Matt Mason

Early on in this rhapsodic account of the evolution of 21st century entrepreneurship – subtitled "How hackers, punk capitalists and graffiti millionaires are remixing our culture and changing the world" – there is an interview with the New York punk pioneer Richard Hell. Talking about how his mid-1970s innovations in ripped clothes and messy hair grew out of his suspicion of corporatised behavioural norms, Hell says, "I've always been really sceptical and suspicious and resentful of people who try to sell you stuff by intimidating you."

Readers trying to locate what it is about Mason's heartfelt advocacy of a world of unrestricted digital creativity which leaves them feeling slightly uneasy might find this quote a good place to start. The author's CV (pirate radio and club DJ; magazine journalist; winner of the Prince's Trust London business of the year award; "Selected as one of the faces of Gordon Brown's Start Talking Ideas campaign") has a definite ring of poacher-turned-gamekeeper about it. And the opening chapters of The Pirate's Dilemma feel like a product of that elite sub-stratum of the advertising industry which trades on a capacity for convincing captains of industry that only with the help of its uniquely high level of sub-cultural awareness can a coming apocalypse be averted.

"What would happen to Nike," Mason wonders, in the midst of a wildly fanciful section on the 3D printer (and of course the history of technological advancement teaches us that today's wildly fanciful is often tomorrow's taken for granted, but that does not mitigate the extent to which the author's bare motivation is hanging out for all to see), "when kids start printing out Air Jordans at the rate at which they illegally download music?" Even as the big cheeses at Nike ponder how best to utilise this book's wealth of useful advice on safeguarding their company's future, they can do so comforted by the knowledge that the issue of digital copyright is "perhaps the most important economic and cultural question of the 21st century".

Those of us old-fashioned enough to be more pressingly concerned about global warming or Aids or Islamic fundamentalism or third world poverty will just have to cling onto that "perhaps". But acclimatising to Mason's relentless boosterism is not just the key to unlocking the treasure-house of fascinating material which The Pirate's Dilemma undoubtedly contains. This book's constant incitements to scepticism actually lie at the very heart of its real public service function.

Just as Mason's own poacher-to-gamekeeper transition echoes the ones he astutely discerns in every would-be regulatory institution, from the US government (quoting Doron S Ben-Atar's observation that "lax enforcement of the intellectual property laws was the primary engine of the American economic miracle" to telling effect) to the phonographic industry, so the successes and failures of his writing reflect the limitations of the information age, as well as its abundant potential. The Pirate's Dilemma contains many fascinating comparisons – establishing vivid parallels between the informal enforcement of intellectual property rights by French chefs and graffiti artists, the seemingly very different histories of disco and home computing, and the rival struggles of advertisers and subway taggers to colonise the public realm. But this book's seductive mood of endless connectivity is also its greatest weakness.

The ability to re-contextualise quotes from persuasive-sounding authorities is, of course, a vital plank in the construction of any intellectual argument. But the complete absence of context or qualification in this book fosters an environment in which every statement appears to have equal weight. And once you have vouchsafed a democratic determination not to differentiate between such variably reliable sources as The Rough Guide to Rock, the UN, Courtney Love, Macchiavelli, Noam Chomsky and the Old Testament, it's only a matter of time before historical chronology also becomes an unnecessary encumbrance.

Thus it is that Mason – who elsewhere demonstrates an impressive grasp of the broad sweep of recent counter-cultural history – finds himself glossing over such administrative actualities as which came first, the situationists or the beat poets; and whether gangsta rap happened before or after Public Enemy's Chuck D called hip hop "black people's CNN". Once you're no longer troubled by such anxieties, it's only a matter of time before language itself starts to break down, and you've lost track of whether you're using the phrase "critical mass" in a figurative sense, or to denote a group of people who don't like something.

It would be unreasonable to expect a book of this scope not to contain any mistakes, but it's hard to shake off the sense of arguments being formulated with a propagandist's disdain for inconvenient realities. Ultimate (and heartening) confirmation that such fine distinctions do matter is supplied by what – in the spirit of The Tipping Point, The Medici Effect and the great tradition of corralling complex theories into snappy three-word formulations – might be termed The Rogue Apostrophe. For all Mason's earnest efforts to justify it via the arcane recesses of game theory, that confusing punctuation mark between the "e" and the "s" of The Pirate's Dilemma just can't stop working against him. This book's central conundrum is meant to be posed by those pesky semi-metaphorical outlaws, not owned by them.