Janice Dickinson, Model, $500 million 

Janice Dickinson earned her place as the first supermodel, but some even though it was a self-acclaimed title. It was still a well-deserved one for her, though, after enduring several rejections from modeling agents in addition to childhood paternal abuse. Her success came in the ‘80s, and daily gigs for her were raking in about $2k.

For someone who was originally rejected, Dickinson was in demand quite a lot. She went on to feature on the cover of Elle magazine and international Vogue editions. Aging is not so great for models, but Dickinson wisely ventured into photography and opened her jewelry line, contributing to her huge net worth.