Digital Entertainment Network
Just as the search-engine category was once wide-open, so was the Internet video field. It's hard to believe, but current throne-holder YouTube didn't even exist until 2005. Before that, several companies competed for market dominance. One of the most promising contestants was the Digital Entertainment Network (DEN).
DEN targeted 18-to-24-year-olds and aimed to become the MTV of the Internet by creating original content: mostly short streaming videos and online series. Great idea, but here come the red flags — and there are a lot of them. Three founders with little management experience and extravagant spending habits? Check. No revenue stream? Check. Outrageous executive salaries? Check. Underage sex scandal? Unfortunately, that's also a check.
Many investors were understandably wary of DEN, but the company managed to gobble up $75 million in venture capital before the founders suddenly quit and fled to Europe in 1999 [source: Tynan]. DEN's upcoming IPO was canceled, and the fugitive trio was arrested in Spain two years later for child-porn possession. CEO Marc Collins-Rector was extradited to the United States in 2004 and received a slap on the wrist. He reportedly hasn't been seen in public since 2007, and lives in obscurity in Belgium.