About Kevin

Get to know the only Leadership candidate who can defeat Justin Trudeau in 2019.

I was born in Montreal Quebec to Lebanese and Irish immigrants, Georgette Bookalam and Terry O’Leary. My father loved long names so they called me Terrance Thomas Kevin O’Leary but when they got me home everybody realized it was going to be total confusion because father and son were both Terrys, the next thing I knew I was Kevin.

Two years later my brother Shane came along and my mother went back to work with my dad at Kiddies Togs, a clothing manufacture on Jean Talon Street in Montreal, where today’s Jean-Talon Market is one of the oldest public markets in Montréal.

My Lebanese grandmother, Akaber, loved to grow apples so I spent my summers working the harvest in her Sainte-Adèle orchard. She was a tough taskmaster and a very head strong woman but loved to spend her Sundays preparing the family dinner.

My Dad was a gregarious Irishman and a great salesman at Kiddies Togs……… we were a happy, middle class family, and my parents worked hard. At the age of 37, Terry……my Dad died leaving my mother Georgette alone with two young kids and times looked tough. To make matters worse I was diagnosed with Dyslexia, the reason given for why I was failing in school.

My mother desperately tried to find a solution for my Dyslexia and luckily met two specialists at McGill University, Marjorie Golik and Sam Rabinovitch, that were treating dyslexia in a new way. I will be forever grateful to Sam and Marjorie for their efforts as they allowed me to excel again. Marjorie taught me to think of my Dyslexia as a super power, after all how many people do you know that can read a book upside down in a mirror!

And then as life would have it things changed, my mother Georgette met George, they fell in love and married, she would spend the rest of her life with this man and George became my stepfather.

He was a young man just finishing his doctorate in business at the University of Illinois at Champaign-Urbana and our whole family moved there. They were wonderful times but we didn’t know what the future would hold.

When George finally graduated he joined the International Labour Organization, part of the United Nations, and that’s when things got wild. We moved everywhere, we saw the world, every two years a brand new country! We started in Egypt, France, Japan then we lived in Tunisia, Ethiopia, Cyprus, Cambodia, Switzerland, you name it I’ve been there!

I didn’t know it at the time but living in all these places around the world and actually seeing them had a profound impact on me…

Imagine living in Addis Ababa, the capital of Ethiopia, at the time of Halie Selassie and actually seeing him long before he became deity of the Rastafarians, playing with his lion cubs. Imagine living in Phnom Penh during the time of Prince Sihanouk, and his lieutenant Pol Pot, who would eventually lead the Khmer Rouge and was responsible for a genocide of his own people during the horrific killing field campaign
in Cambodia.

These were remarkable experiences for me and gave me a unique first hand education on how the world really works.

Now you can read a travelogue on any place but actually living there is a whole different experience. It provides a perspective and appreciation about different religions and cultures that can only be taught in the classroom of real life.

I graduated from the University of Waterloo with a degree in Psychology and Environmental Studies.

At the time, Environmental Studies was a Brand-New faculty led by a distinguished professor, Sally Lerner, who is a recipient of the Distinguished Teacher Award. The discipline combined elements of Planning, Architecture and Engineering at a time when no one was thinking about climate change. But Sally was way ahead of her time and when I graduated she told me that the definition of great leadership would one day be defined by someone who could both manage a growing economy and provide stewardship for the environment in a way that would protect it for future generations. She was so right and I have never forgotten her advice.

My Step-Dad George suggest I combine my Environmental Studies degree with business skills…it was great advice. I attended the MBA program at the Richard Ivey School of Business at the University of Western Ontario.

After I graduated I started my first company Special Event Television. We made sports programming for the networks, shows like Bobby Orr and the Hockey Legions and the Original Six. It all worked out and when we sold the company I took the proceeds and started SoftKey Software Products, later after we turned it into The Learning Company. It was a huge experience for all of us that were involved and it changed the way I looked at being an entrepreneur forever.

Today, I believe if you have been successful as an entrepreneur you owe the next generation a road map not just about your successes but more importunately about your failures to help them from not making the same mistakes. We owe it to our future generations to set them up to have the same great opportunities past generations were given.

I’ve authored three books about money and business and luckily they have all been best sellers.

I got married to Linda when we both had nothing, we could not afford a wedding so we had a reception at our apartment and ordered in pizza for our guests. It was a fun wedding; we were on a journey……if you are trying to build your own business you make sacrifices. When the kids came we had to work as a team to keep it together. Today, I try and spend as much time with my family as I can to make up for the early days when I was not around.

I love to cook and I’m passionate about my O’Leary Fine wines……..I’m still taking photographs and I love to collect guitars and oh yeah I love to play them too, like everybody else I want to be a rock star when I grow up.

Today I spend a lot of time teaching. I tell students you don’t start a business out of greed, it’s not about money…..why do you want to be an entrepreneur? To set yourself free. The pursuit of entrepreneurship is about freedom and helping others achieve their goals at the same time.

Today I’m the Chairman of O’Shares Exchange Traded Funds, I travel the world for our investors looking for growth and investment opportunities, it’s a global enterprise and I love my work. I want to do that for Canada.

People always ask me, why do you keep going? And here is my answer… if you want to help someone, anyone anywhere in the world the best thing you can do is create a job for them, who does that?


I’ll spend the rest of my days encouraging people to do exactly what I have done. Become an entrepreneur, start a business and create jobs, and above all support others who want to do the same.

I believe Canada deserve a Leader with a smart plan to kick start the economy, a leader who supports small businesses, a leader who will fight for you.




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