Kevin O’Leary (aka “Mr. Wonderful”), Shark Tank Host
Today, my guest is Kevin O'Leary (aka "Mr. Wonderful"), the Co-Host of Shark Tank, Entrepreneur and Investor. In 1993, he launched The Learning Company, which developed software that helped kids with reading and math. Six years later, he sold it to Mattel for 3.7 billion dollars, one of the largest tech deals in Canadian history.
As an "Eco-preneur," Kevin specializes in investments that make money--and are environmentally friendly. In 2003, he co-founded Storage Now, Canada's leading developer of climate controlled storage facilities; in 2007, it was acquired by In Storage REIT, for $110 million dollars.
He is also the co-host for Discovery Channel's Project Earth, which explores ways to reverse global warming. His 2012 book The Cold Hard Truth About Men, Women and Money is a candid take on finance, and #1 Globe and Mail bestseller.
A shrewd investor, Kevin is on the investment committee of Hamilton Trust, and on the strategic advisory board of Genstar Capital, a $1.5-billion private equity firm. He is also the host of the podcast "Ask Mr. Wonderful."
In this candid conversation, Kevin shared the real stories behind his entrepreneurial journey, his "Mr. Wonderful" persona, and his philosophies on business and personal freedom.
1. The Ice Cream Epiphany. Kevin revealed that his drive to become an entrepreneur started in high school when he was fired from his first job at an ice cream parlor. After refusing his boss's demand to get on his knees and scrape gum off the floor because he didn't want to be humiliated in front of a girl he liked, he realized the world is divided into two types of people: those who own the store and those who scrape the floor. In that crystal-clear moment, he decided he would never work for anyone else again.
2. The "Mean" Shark is Actually Your Best Friend. Addressing his blunt and ruthless reputation on Shark Tank, Kevin clarified that his persona is not an act. He believes business is strictly black and white—you either make money or lose it. He argues that sugarcoating the truth to failing entrepreneurs is disingenuous, and by telling them the brutal truth when their ideas have no merit, he is actually acting as their best friend by saving them from bankrupting their families.
3. A Passion for Mentoring. Transitioning from a business operator to an investor, Kevin is now deeply committed to giving back by mentoring the next generation. Along with teaching at institutions like MIT and Harvard and hosting an annual retreat for his 29 companies in South Beach, he launched his Ask Mr. Wonderful podcast. The podcast serves as a mentoring platform where he fields calls and offers unfiltered advice to young people about the intertwined nature of life, money, and relationships.
4. The Pursuit of Personal Freedom. Kevin frequently tells his students that entrepreneurship is not about the greed for money, but rather the pursuit of personal freedom. Now at a point in his life where he values time over money, he rigorously manages his schedule in 30-minute increments. For him, the ultimate measure of success is having the freedom to look at his agenda and simply cross off any task he doesn't want to do.
