Parents often encourage their children's dreams, and boost their confidence in moments of doubts. That wasn't the case for Kevin O'Leary, whose father told him his hopes of being a photographer were folly because he wasn't good enough.
While the advice may be harsh, the brutal honesty set the Shark Tank star on a path to becoming a centi-millionaire when he sold one of his companies for more than $4 billion.
In a video posted on X last week, O'Leary explained: "When I graduated from high school, I wanted to be a photographer. I had my own lab downstairs and I was doing all the things I loved to do.
"And he [O'Leary's father] said: 'You're not good enough and you'll starve to death. You should go to college and get a degree.'
"I went on to do an MBA, which ended up being a very important tool for me later."
O'Leary graduated from Western University in 1980 and founded Special Event Television which produced sports programs.
The company harked back to his days behind a camera, O'Leary added: "I was trying to get back to the thing I loved which was photography and production, and make money doing it.
"There was that science and that art coming together in my life."
This company was sold, and O'Leary invested the proceeds into his next start-up, a software company named SoftKey.
SoftKey was the venture O'Leary sold to Mattel for $4.2 billion—giving him a fortune worth $400 million and opening up opportunities such as a spot on the Shark Tank panel.
"Things happen in life, you don't know why, and you only get to look at them in retrospect a long time later," O'Leary added. "But all of that stuff made me what I am today—the good, the bad and the ugly.
"I wouldn't change a thing."
Tough love and luck
O'Leary has become known for his brutal financial advice, both to his friends and family and members of the public.
Members of his family, for example, are forced to sign prenuptial agreements if they want to get married.
Likewise, the man reportedly worth $400 million is vehemently against couples merging their finances—no matter how in love they are.
O'Leary—now chairman of generalist VC fund O'Leary Ventures—was also tough on failing regional banks and advocated letting them collapse.
O'Leary's approach has meant he's had to be upfront about his own investments' successes and failures.
In a video posted to X—the social media site formerly known as Twitter—on Monday, O'Leary said the sale of SoftKey set him up for "a lot of different things."
This compromised of both "great success and crazy failures, losing millions of dollars on some, making millions of dollars on others," he added.
"What I've learned is ... you need a little luck," he continued. "If you're going to be an investor like I am, you need a lot of companies because the ones you think are going to be your best winners never are.
"The ones you think are going to be dogs are, that maybe you're taking a huge risk in, end up being fantastic successes."
He added: "The path that this occurs on is very serendipitous. Markets change, economics change, products change. The outcome of that is never known until you get to the end of the road."
