Richard Simmons | 73 Years Old

Ask those who were trying to lose weight from the previous generation, and they will probably bring up the name Richard Simmons. He was, after all, a household name when it comes to his popular weight loss program. Simmons’ marketing strategy worked well for his Sweatin’ to the Oldies line of aerobics videos. He knew that there was a huge potential for this market, so he started a gym in California.

That decision proved to be correct, and Simmons got more publicity through TV appearances. He also showed good money management skills that led him to acquire a significant net worth. After some time in the limelight, however, the fitness personality withdrew from the public eye in 2014. Some say this was so he could also focus on getting his health in shape, but there has been no official denial or confirmation.