Co-developer of SoftKey International, a software publisher of software intended for home audiences, OLeary built the company from a $10,000 seed investment from his mother into a successful CD-ROM distributor.
Born in Mount Royal, a suburb of Montreal, Canada, to an Irish father who was a salesman. His mother was of Lebanese descent and was a seamstress. Growing up, OLeary was fond of photography and even took it up as a career for some time during his college years. He found soon after that there was unfortunately no money to be made.
He studied for two years at the Royal Military College Saint-Jean, followed by the University of Waterloo, where he received an Honours Bachelor's degree in Environmental Studies and Anthropology. In 1980, he earned an MBA from the Richard Ivey School of Business at The University of Western Ontario.
Immediately after college, OLeary and a couple of friends launched Special Event Television (SET) and found limited success producing small television shows, in-between periods commercials, and local professional hockey games. Later he was bought out for $25,000 by one of his partners.
He then started a software company in the basement of a small Toronto home along with partners John Freeman and Gary Babcock, using his mother's seed investment of $10,000 to launch SoftKey International, a publisher and distributor of CD-ROM based personal computer software for Windows and Macintosh computers during the 1990s. Their products typically consisted of software intended for home audiences, especially compilation discs containing various freeware or shareware game software. SoftKey enjoyed great success by offering "jewel-case only" products, which they dubbed their "Platinum" line.
