From a technical perspective, your anonymity service is only useful if you also have 3 million other users with whom to mix any client’s traffic. (You may choose a different number, but it’s a key issue.)

Secondly, you face some cultural biases that are largely unconscious, but severe in their impact. For example, in the U.S. it usually only takes one mention of the “four horsemen” of Internet malevolence (drug dealers, pedophiles, money launderers, and terrorists) to give prospective investors and clients pause. These same prospects will grouse privately all day and night about their perceived lack of privacy, but they haven’t thought about how to value their privacy in the context of a greater society/environment/marketplace.

I agree that pseudonymity along with strong reputation systems would be a boon to mankind and business. I fear that our failures to date have largely been driven by attempts to manage the process purely through technology. As a long-time security professional, I have come to realize that this never works. All of the Internet firewalls in the world won’t save you if you don’t train your staff properly, and have security policies with buy-in from your senior management. There’s a reason I don’t care much about credit card fraud - there’s a statutory $50 liability limit if I follow certain procedures in the event of loss.

That’s not a technical solution, but it works pretty well. Whether you’re a Liberty Alliance or Passport/Hailstorm fan, or simply like eBay’s feedback system, my contention is that you’lll never have a coherent broadly-applicable environment within which to operate anonymously/pseudonymously unless it is comprised of both well thought-out legislative/regulatory elements, serious marketing communications and technical tools for identity management and reputation tracking.

Alan Mitchell in his book The New Bottom Line also talks about a very different type of frictionless marketing.

As to defending our anonynimity well - thats up to us as individuals and as communities to defend that right.

But I believe that Big Brother will be defested by the supremacy of the community.