Having blown through his ample fortune, Hammer filed for bankruptcy in 1996 with a staggering debt of over $13 million and was forced to sell off his house for a fraction of what he spent to build it. Eventually, he rebranded himself as a minister — a gig that helped pay the bills for a while — and has more recently dipped his toe into the startup waters as a consultant for eight different tech companies. Protip: hire someone you trust to manage your money the moment you come into it. Also, maybe skip the gold-plated gates.
Joe McGauley is a senior editor for Supercompressor and wouldn't dare steal a thing from Rick James (RIP).