Hugh Hefner | Media Mogul | $50 Million

His legacy is quite the colorful one, but many of us were introduced to the media mogul through the popularity of his magazines. To establish the now-iconic brand, Hugh Hefner actually took out a mortgage loan worth $600 and raised it further to $8,000 in order to launch it. It was a risky venture, especially since he had just quit his job. With his ingenuity and undeniable charm, however, Hugh and his business venture became a success. Thanks to the massive fortune he earned along the way, Hugh also became quite a philanthropist through the years.

Among the many efforts he’s taken part in throughout his career include the restoration of the Hollywood sign and his contribution to the University of Southern California’s School of Cinematic Arts. Among his many prized possessions, Hugh’s notorious 21,000-square-foot mansion was valued at $110 million when it was eventually sold. Since then, under the hands of another prolific entrepreneur, the property is currently undergoing major renovations.