HUGH HEFNER

Longtime businessman and founder of the Playboy empire Hugh Hefner was a purely self-made man. After working as a copywriter for Esquire, he launched Playboy magazine in 1953, with iconic actress Marilyn Monroe as the cover model for the very first issue, which sold 50,000 copies. He successfully grew the brand, which spawned clubs and TV shows.

Hefner was notorious for his high-profile relationships with models, whom he invited to live with him at the Playboy Mansion. He was also a political activist who supported progressive causes such as the First Amendment rights and gay marriage. In 2017, Hefner passed away at the age of 91. He is survived by his wife Crystal Harris and his four children. With an abundance of wealth left behind, it’s safe to say the Hefner’s family will be safe from any personal loans in the future.