Jeff Foxworthy – $100m
Jeff Foxworthy is best known as a Blue Collar Comedy Tour member. He went to Georgia Tech for some time but eventually dropped out. He worked at IBM for a while as well. His career switch happened with the encouragement of his colleagues. His sitcom, The Jeff Foxworthy Show was very successful.

Jeff Foxworthy – $100m
Caitlyn Jenner – $100m
Former Olympian Caitlyn Jenner is doing just fine, to say the least. Her athletic career likely contributed to her net worth, but we bet a bigger chunk came from the publicity she got after the gender change. The rest of the family is also doing well, but she is even richer than her ex-spouse Kris Jenner!

Caitlyn Jenner – $100m