Sean "Diddy" Combs — Ciroc, Sean John & DeLeón

Diddy's Ciroc deal with Diageo set a new standard: a 50/50 profit split instead of a flat fee. Ciroc skyrocketed from 40,000 cases to 2 million annually, yielding an estimated $60 million per year in personal income — outperforming #6 Jessica Simpson's fashion brand in yearly take-home. Sean John fashion generated $450 million in peak annual revenue, and with Revolt TV and his Bad Boy catalog, Forbes pegged his total empire at $1 billion in 2022. His business moves were revolutionary, though his conduct has since eclipsed them.