4. Martha Stewart
It might seem like she’s been famous forever, but Stewart was 40 before she caught her big break, which turned out to be her first book, published in the early 1980s. The former model branched off into entrepreneurship in the 1970s, when she entered the catering business. When high-net-worth clients and celebrities started rolling in, she sold her catering venture for $1 million. Years later, she’s certainly been through incredible highs and lows, from her imprisonment for insider trading to her rise as the head of Martha Stewart Living Omnimedia. This highly successful business leader is now worth more than $300 million.