Oprah Winfrey – Weight Watchers

Oprah Winfrey is, in many ways, a relatable woman. People have reached out to her, people have felt she has understood them, and for some reason, people have felt connected to her. However, in terms of her net worth, Winfrey is a superwoman. With $3.1 billion, she’s worth more than we can comprehend! From the age of 23, she has had a tumultuous relationship with her weight—gaining it, losing it, and gaining it all back. With the help of Weight Watchers, a company she bought 10% shares of in 2015 at the cost of $43 million, she lost 42 pounds by January 2017.