How Hugh Hefner turned Playboy from a pipe dream at his kitchen table to an iconic brand reportedly worth $500 million

Playboy founder Hugh Hefner died Wednesday at the age of 91.

In 2016, it was estimated that the playboy and mogul's lifestyle magazine and its "bunny-branded licensing assets" could sell for up to $500 million, according to USA Today. At the time of his death, Hefner owned 100% of the magazine and 35% of the overall brand, according to Business Insider.

Wealth-X, a market research firm, estimates Hefner's net worth was at least $110 million at the time of his death, with $45 million in liquid assets.

So how did Hefner build his iconic and controversial media empire? It all started with $8,000 and some naked photos of Marilyn Monroe.

Here's a look at the Playboy mogul's career: