12. Lou Pearlman - $400 million
Lou wasn’t always a malicious conman. At first, he wanted to be a music mogul. His big break came when ‘NSYNC became famous, which earned Perlman quite a lot of money. Apparently, this isn’t enough. He loved the power too much and went on to swindle people for more than $400 million.
Image source: wikipedia
Time and time again, people invested in his “fictional” Trans Continental Airlines, thinking they would get their money back. That never happened and Lou got a 25-year sentence for his crimes.