In 1985, he graduated from the University of Calgary with an MBA in entrepreneurship and began work as an investment banker with McLeod Young Weir (now Scotia Capital).

He regularly speaks to student and business audiences about the importance of marketing, entrepreneurship, and philanthropy and believes these subjects should be core curriculum.

Specific events hosted by Wilson have supported prostate cancer, David Foster Foundation[18] Right to Play, Little Warriors, Boomer's Legacy, 777 Run for Sight and Dare to Care and the Veterans' Food Bank.

[21] He travelled to Afghanistan to visit front-line Canadian troops with General Walter Natynczyk, Defence Minister Peter MacKay, hockey player Guy Lafleur and actor Paul Gross[22] and has hosted events to support military members and their families.

On June 3, 2020, Wilson made tweets accusing Calgary mayor Naheed Nenshi of "playing the race card" to win the 2017 election.

[24] In response to the tweet, actor and comic Andrew Phung made a call to Calgary non-profits to stop taking donations from Wilson.

's minority government, which resulted in a petition that he be removed from the Order of Canada advisory council "for his continued un-democratic and un-civil comments inciting violence against Canadians and undermining democratic institutions in our country.