9. Vuze
The BitTorrent client formerly known as Azureus was one of the world's most popular BitTorrent programmes, but since version 3 it's been pushing legal content from partners including the BBC and Showtime. Vuze is adamant that its users shouldn't use illegal torrents.
10. Tor
Some technologies get a bad rap, and that's definitely the case with Tor. Despite coming from military-sponsored research and helping activists avoid censorship and surveillance in the world's scarier places, the privacy-protecting service is widely believed to be a tool for criminals.
According to the UK Child Exploitation and Online Protection Centre last year, as reported in the Independent, 5,000 of the estimated 15,000 Tor users in the UK were using it for criminal purposes such as buying drugs and sharing illegal images.
Privacy activists are attempting to repair Tor's reputation: the Electronic Frontier Foundation published "7 things you should know about Tor" this week and argues that everybody should be using it. You should be aware, however, that using it may put you on the NSA's watch list.
11. YouTube
In 2007, YouTube's future wasn't looking too rosy: media giant Viacom was suing its new owner, Google, for $1 billion in damages for alleged copyright infringement. Viacom had a point: as the Wall Street Journal reported back in 2006, many of the top-viewed videos on the site involved "some type of copyright infringement". These days, of course, YouTube generates huge amounts of cash for copyright owners.
12. Christopher Poole
Christopher Poole, aka moot, is best known as the creator of controversial image board 4Chan, but in 2011 he amassed a reported $625,000 in funding to create a new online service called Canvas. The site was described as a PG-rated 4Chan, a place to create and share memes using its built-in image sharing tools. Canvas spawned DrawQuest, an online illustration app, but Poole ran out of money and closed both sites earlier this year.
13. Facemash
Facemash was Hot or Not for Harvard students. "I almost want to put some of these faces next to pictures of some farm animals and have people vote on which is more attractive," wrote its creator, adding later "I'm a jerk for creating this site." The site was shut down and accused of copyright violation, breaching security and violating people's privacy, but its creator, Mark Zuckerberg, went on to invent Facebook.
