Kevin O’Leary’s journey from photography dreams to business success

O’Leary says getting an MBA was eventually better than following his boyhood dream.

Early Photography Passion

Before becoming a well-known businessman and television personality, Kevin O’Leary had dreams of becoming a professional photographer. As a teenager, he built a photography lab in his basement, working hard to pursue his passion.

However, his father disapproved, telling him that he wasn’t talented enough to make a living through photography. O’Leary recalled his father’s words in a video shared on X (formerly Twitter), stating, “He said you’re not good enough and you’ll starve to death.”

This advice led O’Leary to pursue a different path. Following his father’s suggestion, he attended college and later earned an MBA—a decision that became pivotal to his future success.

The Value of an MBA

O’Leary often speaks about the importance of his MBA, which is a significant investment. Top MBA programs in the U.S. can cost upwards of $231,420. However, O’Leary believes the education was worth the cost, stating that it gave him a head start in life and taught him essential business skills.

In a 2021 Facebook post, he credited his MBA with instilling discipline and transforming him from a young man with poor study habits into someone who knew how to make money, defend ideas, and focus on his strengths.

O’Leary graduated from the University of Western Ontario in 1980, where tuition now costs $83,250 per year for domestic students.

Blending Photography and Business

Despite his shift to business, photography continued to play a role in O’Leary’s life.

After graduating, he started Special Event Television, a production company focused on sports entertainment. O’Leary described this venture as his attempt to merge his love of photography with business.

Business Success and Legacy

O’Leary sold Special Event Television and used the proceeds to launch SoftKey, a company that sold educational software. In 1999, he and his partners sold SoftKey to Mattel for $4.2 billion.

Reflecting on his journey, O’Leary expressed no regrets, saying, “All of that stuff made me what I am today, the good, the bad, and the ugly, and I wouldn’t change a thing.”