Kevin O'Leary's Once Got A Reality Check From His Stepdad: Here's What The 'Shark Tank' Star Did To Get Back At Him

Long before he became "Mr. Wonderful" on "Shark Tank," Kevin O'Leary says he got a blunt reality check from his stepfather.

A Harsh Reality Check After High School

In a 2019 appearance on CNBC Make It, O'Leary recalled wanting to pursue creative careers such as music, photography and art after finishing high school.

His stepfather shut that idea down with brutal honesty.

According to O'Leary, his stepfather told him he simply wasn't good enough to compete at the top level. 

"He looked me in the eye after I finished high school and said you’re not good enough at any of those. And you might as well face the reality now … you’re gonna starve to death if you pursue them," O'Leary recalled him saying.

The message wasn't meant to discourage ambition, but to force clarity. "Face reality," O'Leary said, noting that self-deception is often more damaging than criticism.

Separating Passion From Paychecks

Instead of pushing him toward his dreams, O'Leary's stepfather urged him to focus on what he could do well. He identified business and marketing as O'Leary's strengths, advice O'Leary later called "100% right."

The popular investor returned to college to study business and launched his first company immediately after graduating.

Getting ‘Back At Him'—Strategically

O'Leary didn't abandon creativity altogether. In what he described as a quiet act of rebellion, he launched a film production company—allowing him to work with cameras and storytelling, but within a profitable business model.

"I wanted to get back at him a little bit … so what did I start I started a film production company where I could take pictures all day long and it worked," O'Leary stated.

The venture succeeded, leading to a second company in software and eventually paving the way for his rise as an entrepreneur and investor.

O'Leary says the experience shaped his core philosophy: success comes from aligning enjoyment with ability. "The worst thing you can do to yourself is to fool your own self about your potential in your future," he said.

Kevin O'Leary's Path To A $400 Million Net Worth

O'Leary was born July 9, 1954, in Montreal. His mother is of Lebanese descent and his father was of Irish heritage.

After his parents divorced, O'Leary's mother married economist George Kanawaty.

Because of Kanawaty's work with the UN' International Labour Organization, O'Leary spent much of his childhood living abroad.

At his stepfather's encouragement, O'Leary attended university rather than pursuing his early goal of becoming a photographer, developing a growing interest in business and investing during his studies.

While earning his MBA, O'Leary interned at Nabisco and worked as an assistant brand manager on the company's cat food business, an experience he later credited with shaping his career.

After leaving Nabisco, he co-founded television production company Special Event Television with two classmates, selling his stake for $25,000.

In 1986, O'Leary launched software company SoftKey from a Toronto basement with partners John Freeman and Gary Babcock.

According to Celebrity Net Worth, O'Leary currently has a net worth of $400 million.

Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.

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