Bill Stapleton swam at the University of Texas, captaining the swim team and winning gold medals in the 200 IM and 200 fly at the 1987 Pan American Games. He was world-ranked #2 in the 200 IM going into the 1988 Olympics, but became sick on the trip to Seoul, and only made the B final, in which he finished last. Stapleton returned to the University of Texas, earning an MBA and then a law degree, and then started a law practice with Brown McCarroll & Oaks Hartline, where he established a sports management practice, with his first client fellow swimmer Tom Jager. Stapleton later left that firm to start Capital Sports Ventures (CSV), his own company, which was fueled by his representation of Lance Armstrong.
Stapleton helped make Armstrong a wealthy man, as Armstrong won multiple races, including seven consecutive Tours de France from 1999-2005. When Armstrong was dogged by persistent doping rumors, Stapleton stood by him, helping him fight the accusations, during which Armstrong lied, perjured himself during testimony, intimidated witnesses against him, sued multiple people and entities accusing him of PED use, and threatened people with the loss of income and jobs. When all the rumors proved to be true, which Armstrong admitted in early 2013, the entire house of lies collapsed and he lost multiple sources of endorsement income that Stapleton had arranged for him. During this entire sordid affair, which went on for most of decade, Stapleton never admitted any knowledge of these transgressions. After the loss of income from Armstrong's endorsements, CSV was forced to downsize.