50 Cent is pretty adventurous when it comes to business, it seems he's always investing or promoting some new item every other week. He's done it all, from energy drinks to water to headphones and most recently, underwear and vodka. 

However one of his business ventures appears to have fallen flat. SMS Promotions, the company 50 formed as a boxing company, has filed for bankruptcy according to TMZ. The company has only been around for three years, forming in 2012. Although the company signed a few big names, including, Yuriorkis Gamboa, James Kirkland and Olympic medalist Andre Dirrel, it wasn't enough to keep it afloat. The company filed for Chapter 11 on May 25th. Court documents show that SMS Promotions has racked up between $100k and $500k in debt.

An attorney for SMS Promotions reportedly said, "Under the direction of Mr. Jackson, SMS Promotions looks forward to reorganizing as a new corporate entity and becoming one of the leading promotion companies in the world of professional boxing."