Toby Keith | Singer-Songwriter, Record Producer, and Entrepreneur | $365 Million

Toby Keith’s path to fame and fortune wasn’t exactly laid out for him. He had always been fascinated with musicians and received his first guitar when he was 8 years old, but had to focus on other things growing up. He worked in the oil fields and balanced a music career on the side. Keith also played semi-pro football, but it would be some years before he got his shot at music. It was Harold Shedd who received his demo and decided to make investments in the artist. It might have been a risk at the time, but it certainly paid off handsomely for both.

As history has it, in 1993, Toby’s debut single, Should’ve Been a Cowboy, hit no. 1 on the country music charts. It was then followed by his streak of acclaimed singles from his various successful albums, such as Toby Keith, Boomtown, Blue Moon, and Dream Walking. In 2000, his new single, How Do You Like Me Now?, under DreamWorks, became the no. 1 country music of the centennial year.