Sinbad
It’s probably not too surprising that Sinbad went broke. I mean, he didn’t have the best taste in films. Movies like Goodburger, First Kid & Jingle All the Way weren’t examples of great movies. But that’s not why he went broke.
Sinbad ended up filing for bankruptcy twice, once in 2009 and once again in 2013, due to his messed up lending habits. He’d invest and give money to people he didn’t even recognize, then he wouldn’t pay is personal income tax. At one point, he ended up owing the IRS $2.5 Million dollars.
There’s no profit in being a nice guy.