For him, the pursuit of artistic passions has made him better at his day job.
"In business, you need the yin and the yang," he explains. "You want to be a little artistic sometimes — that's the chaos of art — and then the discipline of business. If you're too much of any one of those you're not creative and very often not successful."
Photography specifically has been a passion of O'Leary's since he was a young man. He was in the photo club while going to school at Nepean High School in Ottawa when he began developing his own photos. At one point, he even considered it as a full time career.
"I wanted to become a photographer when I was young," he says. But, his father had different ideas. "My dad told me, 'it's a very competitive space' and that 'maybe you should go learn how to run a business first.'"
After earning an MBA from the Ivey Business School at Western University and building his career as an entrepreneur, O'Leary says it "was good advice."
"Now, because of personal freedom I have a massive collection of cameras from Leicas to Nikons and Canons and every lens they make," he says. "In a way, it's a full circle. I've gotten to do what I wanted to because I was successful in something else, and that's the great thing about entrepreneurship — you can pursue your dreams."