50 Cent is often considered to be one of hip-hop’s most well-off. He’s made millions outside of music—from signing a five-year endorsement deal with Reebok in 2003, to launching his own film and book companies throughout the 2000s, to partnering with Glaceau and making an estimated $100 million when Vitamin Water sold to Coke in 2007. He’s managed to continue to generate the kind of financial footprint that comes from having a solid foundation of knowledge that dictates each of his business decisions.