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In search of cool examples for Stanford Law School class

I'm teaching Privacy and Free Speech Online at Stanford Law School in the Spring Quarter.  The course description:

Privacy and free speech values frequently conflict. Protecting one
individual's privacy often requires preventing another's speech. The
Internet has created significant opportunity for users to express
themselves in chatrooms, on the web, and through new social network
applications. With this increased expression has come increased
disclosures of personal information that may be saved, searched, and
republished. Courts are currently grappling with the privacy- speech
tension in cases where individuals as opposed to media institutions are
the publishers of personal information about themselves and others and
where people are publishing information on public networks but intended
for limited groups of readers. This seminar will explore the tension
between protecting privacy and free speech online, with specific
emphasis on the legal rules and social norms around user initiated
communications and social networking and other web 2.0 applications.

I have a fairly hefty set of legal readings, but I'm also looking for interesting apps, websites, non- legal papers and innovative policies or business models that bring the privacy-speech conflict into focus.  Any ideas?

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