His company owned 25 car dealerships as of March 2018, Peterbilt truck dealerships, Overwaitea Foods, Save-On-Foods, Quality Foods, Ripley's Believe It or Not!, Guinness World Records and radio and TV stations in British Columbia, Alberta, Saskatchewan and Manitoba. Pattison entered the media business when he bought Vancouver AM radio station CJOR with five partners. The Broadcast Group was Canada’s largest western-based radio and TV company in 2018, with 43 radio stations and three TV stations. Pattison Agriculture is the second-largest John Deere dealer in Canada, with 19 locations in Saskatchewan and Manitoba.
In late 2018, Pattison was still working full-time, making a tour of Pattison Agriculture farm equipment dealerships across the west, for example, driving a pickup truck thousands of kilometers to do so. When asked by a Bloomberg reporter whether he ever took a vacation, Pattison replied, "Well, I get 365 days. If you like your work, it’s not work".
Pattison married Mary Hudson, whom he met at the Swift Current church camp when both were 13. Hudson was from Moose Jaw. Some 66 years later in 2018, Pattison commented, "The secret [to a successful marriage] is to marry somebody from Saskatchewan. Then you won’t have a problem!" The couple has three children.