[3][4] He planned to go to law school but instead accepted an offer to work at the National Cheerleaders Association (NCA), which launched his business career.

He went on to found the Universal Cheerleading Association (UCA) and Varsity Spirit in 1974 and would later purchase the NCA after Herkimer retired.

[6] In 2012, Varsity merged with Herff Jones, an Indianapolis company that produces items like graduation apparel and class rings.

[9] Webb is often credited with modernizing cheerleading by making it more competitive, bringing it to the mainstream audience with partnerships with ESPN, favoring more acrobatics and athleticism, and creating new outfit designs (among other things).

[10][3] He is the founder and current president of the International Cheer Union, the world governing body of the sport of cheerleading.