- Hold both Irish and Canadian citizenship.
- Suffered from dyslexia as a child and has given talks on his struggle and how sufferers can treat it as a strength.
- Stepfather worked for an international aid organization and the family spent several years abroad, in Cambodia and Cyprus.
- Has been an avid photographer since high school.
- Attended Royal Military College Saint-Jean for two years after high school.
- Co-founded SoftKey Software Products in 1983 and was President until The Mattel Toy Company purchased it in 1999.
- Author of several books, beginning with Cold Hard Truth: On Business, Money & Life in 2011.
- Created the Future Dragons Fund to assist and encourage teen entrepreneurs.
- Shane O'Leary — Brother
- Linda O'Leary — Wife
- Trevor O'Leary — Son
- Georgette — Mother
- George Kanawaty — Stepfather
- Terry O'Leary — Father
- Savannah O'Leary — Daughter
- University of Waterloo, Waterloo, Ontario, Canada (BSE in Environmental Studies and Psychology, 1977); University of Western Ontario, Ivey Business School, London, Ontario, Canada (MBA, 1980)