14. Vanilla Ice
Vanilla Ice first rose to prominence as a rapper and television personality in 1985. Since then, he has continued to make notable marks on pop culture. But lesser known is the influence he has achieved in the real estate industry over the years.
His aim is simple: he buys homes that show promise, renovates them, and then sells them for a higher amount. He has been doing this for several years and has made quite a decent stash of cash in the process. He still continues to succeed in this arena, which led him to step back into the spotlight with his own reality tv show on HGTV called The Vanilla Ice Project.