I got an email from Fred von Lohmann of the Electronic Frontier Foundation yesterday. It began, "Half the companies you blog about have copyright or privacy legal issues simmering just under the surface. Since most of them are thinly capitalized, when they get into trouble, they're likely to call EFF for legal advice. Several already have."
I called von Lohmann right away, since I've had a nagging feeling for months that too many of the interesting products I've been seeing were legally shaky. So I talked with him to come up with this list: 9 Fun Ways Web 2.0 Startups Can Commit Legal Suicide.