Kevin O’Leary, the well-known investor and “Shark Tank” star, recently shared how harsh advice from his father led him down a path to becoming a centi-millionaire, Fortune reports.
Unlike many parents who encourage their children’s passions, O’Leary’s father bluntly told him that his dream of becoming a photographer wasn’t feasible.
In a video posted on X (formerly Twitter), O’Leary recalled how his father’s tough love changed his career trajectory. After high school, O’Leary was passionate about photography, even running his own lab. However, his father believed he didn’t have the talent to succeed in the field, warning him that he would “starve to death” and advising him to pursue a more practical career.
While difficult to hear, this advice set O’Leary on a new course. He went on to earn an MBA from Western University, which he credits as a crucial tool in his later success. He founded Special Event Television, a company that produced sports programs, combining his interest in photography with production work.
The turning point came when O’Leary sold that company and reinvested the proceeds into a new venture, SoftKey, a software business. In 1999, he sold SoftKey to Mattel for $4.2 billion, propelling him into financial success with a fortune estimated at $400 million. This sale not only secured his wealth but also opened the door to new opportunities, such as his role on the “Shark Tank” panel.
Reflecting on his career path, O’Leary noted that life’s twists and turns are often only understood in hindsight.
“Things happen in life, you don’t know why… But all of that stuff made me what I am today—the good, the bad, and the ugly,” he said.
O’Leary has become known for his blunt approach to business and finance, a style that mirrors the tough love he received from his father. In his personal life, he requires family members to sign prenuptial agreements before marriage and strongly advises couples against merging their finances, no matter how in love they are.
In another video posted on X, O’Leary spoke about the unpredictable nature of business and investing. After selling SoftKey, he experienced both major wins and significant losses.
“You need a little luck,” he said.
O’Leary acknowledged that sometimes the investments you think will succeed don’t, while those that seem risky end up thriving.
O’Leary, now the chairman of O’Leary Ventures, reflected that markets, products, and economic conditions are constantly changing, making it impossible to predict outcomes.
“The path that this occurs on is very serendipitous,” he added.
Despite the ups and downs, O’Leary maintains that his father’s tough advice and the lessons he learned from both successes and failures have been critical to shaping his career.
“I wouldn’t change a thing,” he said.
