In 1991, he founded an investment banking advisory firm called Wilson Mackie & Co. and in 1993 co-founded FirstEnergy Capital Corp. with Rick Grafton, Jim Davidson and N. Murray Edwards. He became a regular columnist for the National Post and went on to own sports teams Derby County FC (an English football club) and the Nashville Predators of NHL (an American hockey team based in Nashville, Tennessee). Wilson is an advocate of strategic philanthropy and often takes a hands-on approach to his support tactics, including shaving his head to support Kids’ Cancer Cure and climbing Mount Kilimanjaro to support Alzheimer’s philanthropy.