Master P — No Limit Records Empire

Percy Miller turned a $10,000 insurance settlement into No Limit Records, selling 100 million records and grossing $500 million by 2000 — all without a major label, making him the most successful independent music mogul on this list. He then launched P. Miller Designs, a phone sex line, and real estate, and even made the Toronto Raptors preseason roster. Forbes estimated his peak net worth at $350 million — 1.75 times Jessica Simpson's fortune. Master P's independent playbook predated the trend by 20 years, all from New Orleans.