I've just finished reading Empire of Blue Water by Stephan Talty, which is a book about 17th-century pirates in the Caribbean and their impact on the history of the New World and Europe. Central to this story was Henry Morgan, a pirate in the service of the English crown, who with his volunteer army was able to consistently out manoeuvre the Spanish who were constrained by their rigid centralised culture and government.
I've also just been reading an article from the May edition of Harvard Business Review about leadership in massively multiplayer online role-playing games (MMORPGs), titled Leadership's Online Labs. There are some interesting parallels between the two, particularly the descriptions of the democratic and transitory leaderships styles and structures within both the games and pirate culture that provide mechanisms for motivating people.
At a stretch we might even compare these parallels with the bigger story of Enterprise 2.0. However, we might not want to take this story too far - in the end, Morgan was a loyalist and eventually became part of the establishment and hunted later hunted down his peers who wouldn't renounce their pirate ways.
His lifestyle of hard drinking also contributed to his early death - perhaps too much social media will be bad for us too?
(Thinking about Enterprise 2.0 and pirates I'm also reminded of Monty Python's short film The Crimson Permanent Assurance, but I digress...)