Thomson purchased the "Timmins Daily Press" in Timmins, Ontario, his first newspaper, with a down payment of $200 in 1934. He began an expansion of radio stations and newspapers in various Ontario locations in partnership with fellow Canadian Jack Kent Cooke. In addition to his media acquisitions, by 1949 Thomson was the owner of a diverse group of companies, including several ladies' hairstyling businesses, a fitted kitchen manufacturer, and an ice-cream cone manufacturing operation. By the early 1950s, he owned 19 newspapers and was president of the Canadian Daily Newspaper Publishers Association, and then began his first foray into the British newspaper business by starting up the "Canadian Weekly Review" to cater to expatriate Canadians living in Britain. He aspired to a peerage, similar to the press barons of the UK, and moved across the Atlantic, settling in Edinburgh.