 His stepfather's international assignments caused the family to move frequently, and O'Leary lived in many places while growing up, including Cambodia, Tunisia, and Cyprus.O'Leary attended Stanstead College and St. George's School, both in Quebec.O'Leary's mother was a skilled investor, investing a third of her weekly paycheque in large-cap, dividend-paying stocks and interest-bearing bonds, ultimately achieving high returns in her investment portfolio.