Growing up in British Columbia in the 1950s and 60s, Henry Fiorillo never thought he would visit Toronto a little then moved there.
His parents were born to immigrants who arrived in Vancouver in 1908. His father’s early years were spent in Fernie, BC, prior to attending UBC in the late 30s and then enlisted in the Canadian Air Force as a flight navigation instructor. His mother was born in Vancouver. Both parents met after an introduction from my mother’s brother, who also attended university, something rare for the sons of Canadian immigrants in the 1930s in British Columbia.
Henry was the second of six children who were introduced to work at a very early age, progressively moving from work in the family’s machine shop, boat building yard and then onto working as a deckhand, mate, and occasionally Captain of the company’s tugboats operating all over the BC Coast.
On some very good fatherly advice, Henry attended the University of British Columbia and then obtained an MBA degree from the University of California, Berkeley. With an MBA under his belt, Henry arrived in Toronto on August 14, 1969, for his first job in the corporate world and where he met his wife Christine, the mother of his four children. Three of Henry’s kids live in Toronto, and his eldest daughter Jessica, lives in New York with her three children.
Henry’s career is a very long way from the tug boats of his youth and has encompassed corporate jobs of increasing responsibility, building and operating a leading strategic market research company, cofounding a successful ad agency, investing, diverse range of businesses in Canada and the US, spending time as a director in the 1990s for two years on the Board of Kids Help Phone and donating to various charities.
Currently dividing this time between a home he and his partner Louise built on the West Coast of Vancouver Island, and at their farm in Caledon.








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Which ’hood are you in?
Since arriving in Toronto, I have lived mostly life in the Annex, Yonge and St. Clair and Forest Hill. Our last home in the city was in a beautiful condo in the DuPont Avenue Road area before Covid persuaded us to live at the Caledon farm, where we live with our two Vizslas and now three cats, part of the year, then drive everyone out West for the winter months.
What do you do?
I enjoy time in nature, both of our farm and our property in British Columbia, while remaining active in several of the businesses that I’ve invested in, providing strategic guidance, mentoring, and helping younger entrepreneurs develop their business ideas.
What are you currently working on?
Currently working on perfecting my Salmon and Halibut Fishing skills and enjoying my Boat Rosie on Vancouver Island, travelling with my partner and my children and grandchildren. I just published my new book, “Fool’s Gold: Angel investing and the Fine Art of Losing Money.”
Where can we find your work?
Anyone with an interest in Angel investing, or sometimes it’s called start-up early-stage investing, will find my book available on Amazon, Indigo, and at select bookstores. “Fool’s Gold: Angel investing and the Fine Art of Losing Money” contains lessons learned over 60 years and how to avoid the potholes in land mines that wait both the novice and even seasoned investors in this high-risk area.
