He’s a well-known Canadian businessman, famously recognized as the founder of the software company SoftKey and a prominent investor on Shark Tank, the popular ABC reality series. Before he rose to fame, he launched SoftKey not long after completing his MBA at The University of Western Ontario—a move that would eventually define his career. Over the years, he’s built a strong reputation in the business world, all while balancing family life. He shares two children, Savannah and Trevor, with his wife, Linda O’Leary. As a key figure on Shark Tank, he’s become a familiar face to audiences, often bringing his sharp insights and entrepreneurial spirit to the table. His journey from a recent graduate to a successful entrepreneur and television personality highlights his drive and vision. And throughout it all, he’s remained a central figure—not just in business, but in the lives of those closest to him.
He also made notable appearances on the Canadian series The Lang and O’Leary Exchange, where he co-starred alongside journalist Amanda Lang, bringing his insights and expertise to a wide audience. In addition, he became a familiar face on Dragons’ Den, not just in Canada but also in the United States version of the show. His role on Dragons’ Den helped solidify his reputation as a sharp investor and business mind. Over time, he built a strong presence across both iterations of the program, making a lasting impression on viewers on both sides of the border. He really made a name for himself through these platforms, especially with his consistent contributions on Dragons’ Den.