Although a professional diver, Webb entered coaching by a chance opportunity to judge a gymnastics competition.
Webb escaped the incident with just a bruised head and later explained that he felt he had made a poor approach and should have landed with his feet first.
Reflecting on that time, Webb recalled that he "got a kick out of being involved, and before I knew it, I was coaching Judy on the trampoline".
Webb had recently lost his third job in 10 years due to spending too much time voluntarily coaching divers.
Webb further suggested that "in most Canadian homes, the parents don't get upset if a daughter spends an extra year or so to finish her schooling".
[8] Webb coached Olympic gold-winning medalist Milena Duchková and arranged her one year visa for her to live in Canada.
Additionally, he worked as coach for the "powerful" Pointe Claire team[4] and in 1984, believed he had "the best group of divers he's ever been involved with".