12. Dan Marino
Dan Marino was a prominent quarterback who played for the Miami Dolphins. During his NFL career he broke many records, earned awards, and made a lot of dough. After his retirement he worked a few jobs as either a sportscaster and an analyst, but it was a bad business move that caused him to nearly go broke.
Back in 2012 at the Coachella concert, we saw Tupac Shakur resurrected as a hologram. Impressed by this, Marino purchased over 1.5 million shares of the company that produced the technology, Digital Domain. However that business would eventually go bankrupt, causing Marino to lose around $14 million.
