7. Tout
In July of 2012, WWE announced a "strategic partnership" with Tout, a social networking service which allows users to distribute and receive 15-second videos across the Web. Immediately, WWE began promoting Tout on their broadcasts ad nauseum, airing "Touts" from wrestlers and fans and consistently soliciting for them on Raw and Smackdown. Basically, if you thought Michael Cole's incessant talk of Twitter trends was annoying, you hadn't seen anything yet now they were hyping something in which they had a direct financial stake. Unfortunately, WWE never an organization to be accused of having its finger on the pulse of popular trends had backed the wrong horse. Shortly after their buy-in to Tout, Twitter acquired Vine, a similar service that became far more popular. In June of 2013, the ultra-hot Instagram introduced their own 15-second video feature. Instagram Video was seen as a direct competitor to Vine, but one thing was clear: Tout was out in the cold. WWE eventually stopped promoting Tout and airing videos recorded with the service on their broadcasts. Today, they still record Touts which can be found at WWE's official page on Tout.com but they've basically given up the fight. It's just as well if they had to hype the WWE Network, the WWE App, Twitter trends, and Tout on Raw, they probably wouldn't be able to air any matches.
Final Tally: $5 million loss as of now, but the investment could always pay off if Instagram decides to shut down or something