One interesting thing I've noticed that the people behind the best filesharing networks tend to have tremendous success with their later projects.
Napster is the obvious one. After Napster went down, Shawn Fanning co-founded Rupture and Path, and Sean Parker went on to become the first president of Facebook, key investor in Spotify, and managing partner at the Founders Fund.
Kazaa is another great example. After their legal walloping, the founders and development team behind Kazaa regrouped to form Skype.
And then there's The Pirate Bay, which is still rolling merrily along, court rulings notwithstanding. Its team hasn't created any billion-dollar companies yet (we'll see what happens with Flattr), but they created a political party that's won elections in multiple countries, as well as the webhosting company PRQ, which was Wikileaks' home in its early days.
I don't think all of these later successes are a coincidence. Filesharing involves hard technical problems, hard logistical problems, and intense competition. If you were an investor, a blind strategy of giving money to the best pirates you can find seems like it might be surprisingly sound.