Kevin O'Leary on Canada's Future Outlook, Personal Branding |

Exclusive: “Mr. Wonderful” on Canada’s Future, Careers and Business: An Interview with Kevin O’Leary

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We recently had a chance to speak with Kevin O’Leary of Dragon’s Den fame and get his insights on the future of Canada’s economy, building a personal brand, careers and more.

A big thanks to Massive Media and MNP for putting on the event with Kevin on November 8th, and helping to make this happen.

Enjoy the interview:

Interview Transcript (in progress draft)

Welcome everyone this is Michael Zipursky of and today we have someone special on the line. I have with us none other than Kevin O’Leary. Kevin is well known as a Star on the T.V shows Dragons Den in Canada and Shark Tank in the U.S. He’s launched his own line of wine called “O’Leary Fine Wines” and is a founder at O’Leary Funds, an investment fund. Kevin, welcome.

Kevin O’ Leary: Thank you very much.

Michael Zipursky: I want to start by asking you about branding. You’re a master of personal branding which is evident from your success on T.V and your other ventures. What would you suggest to someone that wants to build their own personal brand, what attributes are important, what actions would you say are necessary and can you share with us some specific steps that you took?

If you’re always worried what other people think of you, you won’t establish your brand and you won’t break through.

Kevin O’ Leary: I think the key to brand building for an individual is honesty. [Each person can connect that to either print, radio, television, internet whatever vehicle they are using. Their communication has to be based on honesty and a two-way dialogue.] And sometimes that’s difficult because sometimes particularly in my case the truth is sometimes quiet brutal because we are dealing with money which is very black and white. So, sometimes it’s very harsh to say to somebody, this is a bad idea you’re losing your money I wouldn’t invest in you. But that’s the truth and I think all the time at least in my case being honest has benefited me…and has enabled me to build a brand around financial services and goods… I mean that’s what I do. Wine is a hobby of mine obviously but may main businesses are O’Leary Funds we have [over a billion dollars] under management, O’Leary mortgages which I am launching very soon and I am very proud of that. But it is based on the appeal that you can trust me even though my message maybe harsh. And you know that is the truth as far as I’m concerned and I think it’s important.

Michael Zipursky: There may be people listening to this that want to be able to express their opinion so clearly but find it a real challenge because they don’t want to hurt people’s feelings or go up against the status quo. What would you say to those people?

Kevin O’ Leary: Well, that’s a mistake. If you’re always worried what other people think of you, you won’t establish your brand and you won’t break through. You can’t do that. You have to be honest to yourself above all. Speak your message the way you feel that make sense to you. It maybe not connect with everybody. [You can’t try to please everybody.] And the key to telling the truth is you always speak the truth and you never have to remember what you said. It will always be the truth today, tomorrow or a hundred years from now. So, at the end of the day that’s what I have found has been the constant. The other challenge of brand building that people want to communicate is finding the platform that fits them.  I’ve seen tremendous successes on the internet, great successes on the radio, in print, in television it’s difficult to be good at all things so you’ve got to find out the one that fits your personality and work with that. And I think that there’s a lot of trial and error too. I’ve been doing this now for 11 years and I found that it works for me or it doesn’t.

Micheal Zipursky: Kevin, you are on both Dragon’s Den in Canada and Shark Tank in the U.S. You’ve done business in both countries. What are the real differences between working and doing business in Canada versus the U.S?

Kevin O’ Leary: We have three major sectors in Canada. We have materials, we have financial services and we have energy. So when you look at goods and services in the Canadian market, you tend to be focused around supporting those three sectors. There are 10 sectors in the U.S. So you’ve got seven more areas, medical supplies, pharmaceuticals for example, and a much broader technology market so the deals tend to reflect more sector exposure which makes them in some ways more interesting. Now, on the other hand it’s far more competitive in the U.S so just because you have a product and service there doesn’t mean 50 other competitors so getting something forward is much harder. But you know it’s a market, 10 times in size of Canada and if offers some opportunity that come with that. I think both are fantastic. They support entrepreneurs. They celebrate entrepreneurialism. They are focused on the individual ability to create wealth. These all are good things as far as I am concerned. Recently, a girl came up to me and she said I wanted to be an entrepreneur and I said, “Why?” She said “I wanna be FREE”.

Fear of bankruptcy, fear of failure, those things are extremely motivating and they certainly worked for me.

Michael Zipursky: Kevin, what about the differences in marketing and personalities between the two countries. Isn’t marketing and the approach in business more aggressive in the US?

Kevin O’ Leary: It’s true. Just cutting through the noise is becoming harder and harder. I mean you think about all of the information that bombards people every day. Through every kind of vehicle possible social media, wireless, television, print all the ways there connected to the world. It’s very hard to get the message through and I think having a brand changes all that. I make the assumption and so far we’ve been right, it’s not just Kevin O’Leary it’s the team of people behind me. We make the assumption we get 1 to 3 percent of the market when we show up because of our brand. And then go beyond that we have to execute very, very well. So, when we looked at entering something like the mortgage market we [think about] what are we going to have to invest to get our message through, what advantages do we have because we have a brand, what disadvantages are there? But, generally speaking the brand helps you get some share initial foot hold that you can build a business of. It’s worked in our mutual fund business, it’s worked in the wine business, and [we think it will be] very successful in the mortgage business. So the key for me is to make sure that I keep my message consistent, I remain honest which I find my basic personality anyways. It’s a fair amount of work but what I enjoy doing is creating businesses, hiring people and [growing businesses]. This is my reason to be here is and that’s why I do it.

Michael Zipursky: You just mentioned hiring so let’s switch it up here for a minute. I want to ask you about hiring and talent. When you’re looking to hire someone, what are the top characteristics that you are looking for?

Kevin O’ Leary: Well, I have a guy name Alex Kenji from O’Leary Funds. He is the President of the firm. He and I have very simple philosophy. We start by hiring interns. We want smart, aggressive people that can self contain, in other words they don’t need a tremendous amount of tutorial work with us. They don’t need a lot of supervision. They know what they have to get done. They’ve given a task they go do it. Because you know when you’re doing start ups like this, and even in an established business, [O’Leary Funds now has 50 people in it…you want very aggressive individuals. I want these people to get rich. I want to give them equity. I want them to work like I did when I was 23 years old. Which is 25 hours a day and if you don’t show up on Saturday don’t even bother coming in. So, my attitude is if you’re not that kind of person you’re not working with Kevin O’Leary and so that’s why our businesses are successful. We have a lot of aggressive, smart, young people that have equal upside and they want to work hard. And if you’re into that mode you know, when you’re young you could take risk in terms of what you’re doing. And I think that’s the kind of person were attracting. So far it’s worked. You know hard work here is not for everybody, trust me.

Michael Zipursky: Let me ask you about the Canadian economy right now. You follow the economy and the market very closely. What do you see are the biggest areas for employment for Canada in the future and what skills do you see will be highest in demand?

Kevin O’ Leary: Well, I think what’s going to happen is we are going to be challenged in North America. Our largest trading partner is the US and they are going through a pretty serious deleveraging process and a slowing. And I think that will be systemic for a long, long time. Because capital is moving away from slow growth GDP environments, like the US, to high growth environments like Brazil and China. Luckily in Canada we have a different set of problems, we have resources, and in many cases the technology that these emerging and emerged economies want. I’ll give you an example, the Prime Minister is in India right now. That is a fantastic place to go do business because they got 5-6% GDP growth going forward and they needs lots and lots of raw materials and technology to develop those raw materials. For example, gas fracking technology, this is a great area for us to do business with us, both with China and India. And I think getting these trade agreements in place will make it much easier for us in the next decade, and will reduce our dependence on the slow growth American market, and move forward with a global perspective in how we trade. So for any Canadian that is coming out of school or wants to be an entrepreneur, looking for goods and services, they should look to service markets outside of the US is a great idea. At the end of the day, if you want to stay in Canada, you’ll be doing it with a business that will be servicing other countries with higher GDP growth.

Michael Zipursky: Kevin, you seem to have an amazing drive and motivation to get a lot done (from writing a book and investments…to wine, T.V. and so on). What kept you motivated when you were just getting started in your career, and what motivates you today I mean to get out to get out of bed and to perform a world-class these days?

Kevin O’ Leary: When I was starting yet what motivated me more than anything else is FEAR OF FAILURE. I didn’t want to fail. And I was also broke. So, fear of bankruptcy, fear of failure, those things are extremely motivating and they certainly worked for me. I tried retirement many years ago. I was retired for 3 years and it’s very boring. And so what I’m trying to do is say, I look at my day everyday and I say, “if today is my last day on earth”, and I knew that tomorrow at 6 o’clock I’ll be gone… Is there anything in tomorrow’s schedule that I don’t want to do? And then I’ll just cancel it. I try to live my life to the fullest. I want to do things I enjoy. I enjoy business. I enjoy certain hobbies like guitar playing, photography, wine drinking, wine collecting…I do all of those things. The reason you want to pursue wealth is not for having a whole bunch of money in the bank. That’s irrelevant. You want it for freedom to do whatever you like. I enjoy my wealth because I can do whatever I like any time I want to. If I don’t want to do something I don’t do it. And this is a very good motivational force for anybody who wants to pursue freedom. It’ not wealth, that doesn’t mean anything. Freedom means a lot. [When you age and get close to 50 years old, you really realize that the most valuable thing you have is your TIME.] And certainly you don’t want to spend it doing something you don’t want to do.

Michael Zipursky: Kevin, great points and advice. Thank you so much for sharing with all our readers and with the community. It was a pleasure speaking with you.

Kevin O’ Leary: Thank you very much. I appreciate it.