Watching a brand self-destruct is a bit like watching a wreck on the highway. There's a certain horrid fascination that compels you to look even though you know you should just keep going (unless you're a paramedic).
The dust-up over O'Reilly's claim to the term "Web 2.0" as it relates to conferences and other events may be legal but it's also dumb. Not what I've come to expect from a company that's usually pretty clued in. There has been so much analysis written, along with the inevitable measure of vituperative bile spewed, over this mess already that I'm not going to bother restating the details - if you need to do research, check techmeme.
Two observations and I plan to keep motoring along.
"Sesame Street are also suing to stop use of "the number two" and "the letter O"...
...who owns "point"?"
Sums it up pretty nicely IMO. Winge and the rest of the O'Reilly crew can try to justify this is tones of corporate governance, protection of brand and IP, and all other logical constructs until they are blue in the face. It won't matter a bit. They have displayed incredibly poor judgement in how this affair has been handled. They've picked on a little guy, with no attempt to handle the situation nicely. Coming out swinging with a cease-and-desist letter from attorneys without so much as a "can we talk about this?" is completely contrary to what O'Reilly's reputation has been culivated to represent.
I don't know if it was hubris, arrogance, and pride or a simple failure to consider the implications taking a stance like this might have. Either way, it is a catastrophic failure of leadership. Since Brady confirmed that O'Reilly was aware of how CMP, their event partner was planning to address this situation in advance, there's no shelter in ignorance to be had. Tim O'Reilly had better get back from his vacation soon or he'll be sweeping up what remains of his eponymous brand's reputation with a broom.
UPDATE: Tim O'Reilly responds to this messy situation with a reasonable and nicely-worded explanation of what he thinks could have been handled better by all parties involved and expresses his dismay at the piling on that took place in his absence.