Bay Street Bull Magazine: Luxury Business and Lifestyle


Bay St. Bull Power 50: Kevin O’Leary

The Power 50 is a collection of Canada’s top people, places and things of 2016. Our list is filled with game changers from all corners of the nation that are inspiring, innovating and influencing the way we live and work from the top. Giving you the best from every city, industry, office and home, The Bull’s Canadian Power 50 is not your typical list and instead is the definitive guide to who and what is changing the way Canada lives, works and plays. 

1. Kevin O'Leary: Co-Founder and Chairman, O’Leary Financial Group; media personality.

Photography by Janick Laurent

Creative Direction by Lance Chung

Kevin O’Leary is exactly the person you see on TV. He’s unapologetic. He’s outspoken. He’s even a little smug. His is a brand that is frank, if not a bit brash at times, simply because mediocrity deserves no time. (And you know what they say about time.) O’Leary is a guy’s guy who can pivot seamlessly from talking about his love of Prince’s guitar skills to the lack of leadership in Canada. And yet, through each topic, you can’t help but become enamoured with someone whose tune doesn’t waver. He speaks with a conviction that is, dare we say, refreshing and makes you believe in what he has to say. It’s that brutal honesty that is perhaps just what people need these days.


You had what one could call a relatively nomadic upbringing. How much did these changes in scenery play a role in defining your ambitions at the time?

I lived in multiple countries in my early years because my step dad joined the ILO [International Labour Organisation] department of the United Nations, so [I lived in] Cambodia, Tunisia, Ethiopia, Cyprus, Japan, France and Egypt. He moved every 18 months or two years, that was his mandate. The long-term effect for me is it’s made me a global investor. I’m not scared to invest in real estate in Cambodia. I understand the French infrastructure there. It’s not that wild a jump for me because I understand the history of that country. I was there in the late sixties, they are very entrepreneurial and it’s got a huge democratic tonality to it because of the French history. The point is, investing globally is the outcome of that experience. Plus, I have a lot of friends all around the world now; people I’ve stayed in touch with my whole life.

What stopped you from pursuing photography at the time, or did you also begin to fall in love with business too?

I was more in love with photography but my step-dad was teaching business at the University of Ottawa. He said to me, “Listen, what you don’t know about photography is you may not be as good as you think because there’s so much competition in the space. And to make a living with it is going to be incredibly hard. Why don’t you mitigate your risks with some optionality? Do a business degree, and then if you wish to go back, at least you’ll have the tool kit.” It made a lot of sense to me because I didn’t know with certainty. What happened was I graduated from the University of Waterloo, then went to Ivey [Business School] and did an MBA there and went right back into production. I started Special Event Television with two partners. We were lucky in successfully producing “The Original Six”, “Bobby Orr and the Hockey Legends” and all the intermissions for Hockey Night in Canada. My dad was right, it was a good combination of business and what I wanted to do in film production and television production. We sold that company and that was the beginning of The Learning Company, which changed my life dramatically. Life is serendipitous. I’m launching my third photo exhibit in New York City at the New York Art Fair. It’s kind of like going back to what I wanted to do. I’ve gone full circle.


Working at Nabisco, and even the other jobs you had when you were younger, how much did they inspire you to be an entrepreneur? What was the spark that lead you to starting SoftKey in a Toronto basement way back when?

I had an experience that has been documented before, but I worked at a place in Ottawa called Magoo’s Ice Cream Parlour. It was my first official job. I was scooping ice cream with a woman there and she said, “listen, you got to scrape the gum off the floor every night”. It had mexican tiles, people dumped their gum before they started eating their ice cream and it would always have really bad gum stains. This was my first night and the girl I was hot for in grade 11 was working at a shoe store across the hall. I didn’t want to have her see me on the ground scraping, so said, “Hey listen, I’m a scooper, not a scraper.” She fired me. It was the first time I ever got fired, it was really humiliating. That’s when I decided I would never work for anybody again. I really owe her a huge debt of gratitude. The only other job I ever had was, I worked for Nabisco brands during my summer breaks at university. I’ve never had a full-time job or had a boss. And I think it’s all because of Magoo’s Ice Cream. I went back decades later to find her, to thank her. We actually took a film crew from Dragon’s Den to that. It occurred to me, I can now afford to bulldoze the mall but without her that wouldn’t have happened. That mall should be bulldozed in my opinion — it’s called Lincoln Fields.

What kind of planning went into making that leap into entrepreneurship?

I just didn’t like the feeling of being controlled by somebody. I teach now, primarily graduate courses of engineers, and I tell the class - and I’m usually right on the statistics - one-third of them probably have what it takes to be an entrepreneur and take the risks because they are really good candidates to start businesses for a wide range of reasons. But, it’s not for everybody. I don’t think when you start the journey you understand the compromise you’re making and the sacrifice. Particularly today, where some guy in India and China is getting up and kicking your ass and they’re willing to work 25 hours a day, and you’re only willing to work 24, you’ve got to be ready to part with ten years of your life. And then the whole reward is not money, it’s the freedom that money provides down the road. So I tell people, “Look, if you want to go to the soccer games with your kids and if you want to take holidays, you don’t want to do this. You want to be a grunt working for somebody else.” A grunt’s life is not horrible, you can get a good grunt job somewhere and just go through life that way. For those of you who know that’s not your destiny, you’ve got to take the chance now. But you have to understand the 15 year sacrifice. These overnight stories are far and few between. Most entrepreneurs bust their asses for a long period of time and what that proves later is freedom to do whatever you like. I don’t do anything I don't want to do anymore. If I don’t like it, I just cancel it. There’s nothing anybody can do about it. It’s not arrogance, it’s just using your time for the things that you deserve after having worked so hard.

When the business was sold to Mattel, you stayed on as an employee to manage the business. What are some of the pitfalls of deals like this that take control away from someone running a business while keeping them in it?

It was the late nineties, the transition was moving from CD-ROM distribution of software to online so our reinvestment was going in the hundreds of millions. We were eating the market share of Mindshare for children between the ages of three and seven. They were spending more time on software than toys. So both toy companies were interested in buying what we did because we were leading in reading and math. We were the number one provider in the world for test scores and entertainment. The decision for our board — not everybody decided and agreed — was do we up the ante and reinvest basically two years’ worth of profits, and redefine the business online? Or do we partner with multiple brands like a Hasbro or Mattel, and then convert Barbie and all of the other Fisher-Price brands into consumable software? The vision was a good one, the execution was abysmal. But, that’s the nature of trying to clash cultures of entrepreneurial companies with ones that are decades old. It was a long retractive negotiation and it was the right thing for all shareholders at the end of the day. What it left me with was a three year non-compete, which was frustrating because none of us stayed with Mattel very long. I wanted to go back and start a new deal and I couldn’t. I was getting paid — it’s the best salary I made walking around in a housecoat. But, that was basically it. I used those three years to visit every beach on earth and then when it was over I realized being retired sucks and I started all over again. I remember somebody saying to me, making the first five million is impossible, making the first 20 million is more than impossible. After that it starts getting easy. And they’re right because you have enough capital to take significant risks and maintain significant ownership. And so, the first five million, it’s a bitch! It’s really hard to do. And I think the goal every entrepreneur should have is get the first five million.


When you first delved into the world of television, from BNN to Dragon’s Den, what was it that compelled you to the notion that this would be good for building your professional brand?

I would have to give most of the credit to what I call my “hobby gone insane” to a guy named Jack Fleischmann, who was starting up BNN at a time when the CRTC was issuing licences in Canada to specific verticals on the new direct cable model. I was working with Thomas H. Lee [a private equity firm]. I was a Canadian citizen even though I had my kids in Boston and we were living in Boston. The Thomas H. Lee crew said, “They are selling licenses up in Canada. You’re Canadian, it has to be 51 per cent owned. Why don’t you just go up there and buy everything. Don’t differentiate, just buy every license you can get and we’ll package and piece it up. Buy the gay channel, the dog food channel, the movie channel, the business channel, just buy everything.” I went up and I started bidding on all this stuff. The plan was I would form a company and they would have 49 and I would have 51. There was a woman there named Janice Mackey Frayer, who’s become a very famous reporter in the Middle East. She’s gone on to do great things. She was debating with me about the CRTC rule and Canadian ownership and I argued that it was a stupid rule, that it cost capital to be much higher than if we opened up and were more market-driven. We got into one hell of an argument, I’m not sure she didn’t throw a fist at me. We were on her show and the phone lines lit up, and Fleischmann said you gotta come back tomorrow and we did it again. That was the beginning. I realized the interesting thing about television is you can’t bullshit people on TV. They smell bullshit from a mile away. If you’re honest and you tell the truth, it’s a powerful medium. For me, the model now of celebrity with business is interesting. If you think about any business, the number one challenge is customer acquisition costs. I reach 10.2 million eyeballs a week now across all the different networks I work on in the United States and Canada. When I associate myself with a company, I can start to drive customers to our goods and services. In a way that makes us wicked competitive. I can take a commodity like cupcakes and make it the number one cupcake shipped in America by FedEx, which is what Wicked Good Cupcakes is. Honeyfund is the number one provider of gifting online to honeymooners. My model is to buy either a non-control or a control position in a company, form a relationship with the management and then turn on the celebrity. Go to to CNBC, FOX and talk about the company. I’m totally transparent about it. I tell these networks, look I’ve got an amazing entrepreneur. What I’ve found over the last eight years, not some of my returns, but all of my returns have come from companies owned by women. This adage that if you want something done, give it to a busy mother is very applicable to a small company with sales of five to 300 million as a range. And that story is very compelling. It’s on message because women are being empowered. But, I’m not doing it for gender warfare. I don’t give a shit, I just want a return. I’d give money to a goat if I could get a return. I’m now backing women because I’m getting more capital back faster. Arianna Huffington heard that story and said let’s do a whole thing with you on the Huffington Post, we get to 122 million. If we’re going to do that Arianna, I want to feature my companies. Our sales exploded after that. That’s my model. I don’t need to do more TV. I’d love to make my company more successful, that’s why.

Your public persona has taken on the form of the antagonist, or anti-hero even. How much of that was intentional, or was it just your personality shining through?

My thing about business is it’s binary — either you make money or you lose money. Why do you have to bullshit yourself? When you have a lousy business idea, and it’s stupid, and you’ve run it for three years and you’re still losing money, you’ve got to take it behind the barn and shoot it. It’s that simple. That’s the Darwinian nature of business. People cry and tell me, “I can’t do that”. Yes, you can! You’ve wasted all your family’s money. Thank goodness you met me. I’m telling you the truth, your idea is stupid, it has no merit, it’s bankrupt. It doesn’t matter if they cry. Imagine, if they can’t handle me, what’s the real world going to do. It’ll eat them alive! I don’t worry about any of that stuff. I’m not trying to make friends when I’m investing, I’m trying to make money. I really don’t give a shit at all.

The middle seat. How do you get it?

The nature of television is just chaos. If you think about the discipline of investing versus what happens in television, I’m so glad I have those years doing Special Event Television with Ralph Mellanby. Live hockey games is what we used to do. I was a showrunner for Harold Ballard when they used to shoot the [Maple] Leaf games at the [Maple Leaf] Gardens. I would sit beside Harold, and I was the liaison between him and the producers. He wouldn’t pick up the phone and talk to Ralph. He would make me run over and he’d say, “Kid, I don't want any Russians skating on the ice as stars of the game. You go tell Mellanby that”. So I ran and said, “Harold says no Russians touch the ice when the game is over or he’s going to turn all the electricity off in the gardens.” Ralph said,"tell him to go ‘beep’ himself", and I go back and said, “they are going to put a Russian on the ice”. All of the guys that worked at the Gardens were from the Second World War that Harold knew, they were very tight. The minute the Russian guy stepped on the ice, the entire place shut down. The CBC went off the air for five minutes with black screens and I realized, “wow, this is crazy. What happened here was crazy. That's chaos.” So when you talk about what happens on television, there is no rhyme or reason. When you're deciding who sits in what seat, that's just some random outcome. They're shooting a show, they don't know how it's going to work. People forget that nobody watched Dragon's Den or Shark Tank for three years. And then one day — I'll never forget it — I was at the airport, no had ever recognized me and this guy to my right, he says, "Are you Kevin O’Leary, that guy on Shark Tank?" And I said, "Yeah". He said, "You're an asshole." That was the first time that the whole thing started. The whole thing about the middle seat, there's no rhyme or reason to that. When it's working you don't fuck with it. The thing about TV is you don't change anything when it's working. They'll loathe to make any changes, it's the American Idol story. Simon Cowell should have never left that show. It’s basically what everybody knows about TV.

Over the years, your approach to deals on your shows seem to have evolved from investing for equity to offering more lending and licensing deals. What are some of the incentives and drawbacks offering capital to the businesses who need it?

The reason it's changed — and I'll be frank and transparent with you — is if you're lucky enough to get me as an investor, you're life's going to change because I'm going to bring so many customers. If you think you're getting that cheap, you're dreaming. I'm going to extract every single dime I can. It's going to be incredibly painful and the reason is, it's worth it. I don't actually care what you want or what valuation you like, it is completely irrelevant to me. To get me as an investor, I decide. I will make you an offer, it'll be the only offer you get. The structure will be the only one you're offered. If you don't want it, you don't have to take it, the other 90 guys are going to do it. That's how I do it. It's totally arrogant, it totally works.

Do you do use this style outside of TV?

I'm getting absolutely worse. [The non-TV deals are] brutal. I’m horrible. I'm so lucky I don't have to deal with it. That's actually how I look at it.

Who is the co-host on any show that you’ve enjoyed working with?

What I liked about Chile [David Chilton] is he had the same philosophy about return of capital [as me]. So the deals we used to compete on were very much structured the same. I don't do five per cent equity or ten per cent equity — that's a very stupid strategy. You have no chance to get your capital back. My structures put me very high on the balance sheet because I add so much value. I'm not scared to tie my exit to my ability to generate revenue, whatever it is. I liked Chile because he focused on what the competitive advantages of a company were and how he could get his capital back in total alignment with the entrepreneur. That is also my way of looking at it. I'm not asking for anything that I don’t want you to get; I don't want my money back first, I want it coming back with you. If you are taking out a dollar and I own ten per cent, I want ten cents, I don't want to be disrespected. That kind of structure is what what he did. Plus, his prowess as a publisher. That franchise that he built is the envy of so many businesses. Writers think about what he did.


You have several ventures on the go, from financial services, to producing wine, to publishing and public speaking. How do you avoid spreading yourself too thin?

I spend about 60 per cent of my day dealing with my portfolio. I have a great support team in multiple cities. Generally, each company has a CEO. The wine business last week on Wednesday, we broke records in the United States. We sold 2.97 million dollars of wine in 20 hours on QVC. That’s unprecedented, it’s unheard of. It’s my relationship with they buying constituency that knows me after eight years of Shark Tank that I am the wine guy. The other sharks just swill beer. I blend my own wines in Sonoma in the US market as I do with my Vineland Estates in Canada. You can’t bring juice over the border, so in Canada I have a relationship with the LCBO and Vineland Estates. My job is to blend the wines and put my name on it. If it has my name on it, it’s going to be good, it’s going to be great value. The same thing in the US, a whole team set that day up. We were the TSV, which is called “The Special Value” of QVC. You reached a 100 million people and you sell a lot of stuff, so I brought an additional three companies on that day: Lovepop Cards out of Boston, Wicked Good Cupcakes and Groovebook, which were all my Shark Tank deals. I said, “Guys, we’re going to be touching base with 100 million people. I’m going to endorse all these products, we’re going to sell a ton of them and you’re all going to pay me as we do everyday. And, of course, everybody agreed and that’s how we march on. The reason we were able to do that is a combination of celebrity and the brand of who I am. People trust me. You may not like me, but you trust me. Whether it’s in financial services, mutual funds, wine or any of these things, it’s not about being liked, it’s about being trusted. To garner someone’s trust is extremely hard to do. It took me a long, long time. I never want to breach that.

Speaking of your businesses, specifically in the financial sector, Fintech is buzzing of late. How much of your business activities are being influenced, either through competitive threat or a need to adjust, by changes in technology?

It’s very exciting to find someone who thinks out of the box that is looking at a very staid and established industry. I like to invest in teams like that. Generally they are teams because it’s incredibly hard to swim upstream. Fintech is fascinating because of the multi-trillion dollar financial service investment businesses in North America. Fintech and robo-investing strategies reduce their costs. I spend a lot of time on Wall Street, and Bay Street, talking with the money center banks, the wire houses, the Morgan Stanleys and the Goldman-Sachs about what their vision is. One of my big initiatives is financial literacy starting at the age of five. I’m trying to teach kids about debt. I spend a lot of time on this. All of [the banks] want the same thing: potential customers. I think what’s going to work is a combination of a robo-Fintech with an element of a human being involved.

If you actually ask any individual if they trust a robot with their own net worth, it’s hard to find anybody that will do that. They want to talk to a human being. So the models that interest me are some of the newer ones that are called Fintech 2.0 that combine platforms that give you recommendations. Schwab is doing this for example, it’s robo-investing. There are full allocation and diversification strategies and multiple assets where you can choose the style, value and growth. But before you pull the trigger, there’s a human being who you can call and say, “I set this up myself. Here’s my account number. Here’s my portfolio. What do you think?” And even though it’s only a 30 or 60 second conversation, that actually, if you look at the research, gets them over the hump. So it tells me that going into the black void in financial services isn’t going to work as well as setting up all the infrastructure because robo-investing, allocation and sectoral diversification is really smart. That’s done by algorithm, that makes sense. But to actually put that first ten thousand dollars in, you need somebody in there to say, “I looked at it, I’d trim back on energy, it’s at 21 per cent, I think it should be down to 18”. Okay. Boom. I could talk like this for hours. The real strength will still be the banks that run the platforms that keep the person there. Even though the leverage is amazing, you can just spend a minute on the phone with somebody.


How much of your current public political positioning is driven by your ambitions versus a necessity in the current political leadership context?

When I teach at Notre Dame, nobody comes down to the podium. Nobody ever says to me, “Hey Kevin can you give me access to your rolodex? I need to to talk to the guys at Google, Microsoft, Apple, Facebook.” They don’t have to do that. They are already being solicited by all these firms. Their choices, particularity at MIT, are global. That’s the biggest brand in engineering in the world. Our equivalent is probably McGill in Canada. You teach a class in Canada, a third of the class, the entrepreneurial ones, come down and say, “Listen, you gotta get me a job at Apple. I’m trying to get into Silicon Valley, I want to go down to San Francisco. Help me, you’re a fellow Canadian and you know all those guys.” And I say to them, “Why the hell do you want to leave here? Why don’t you stay here and grow a company in Canada?” The answer is always the same. Why would I want to stay and get paid a dollar less? Why do I want to get taxed at 54.2 per cent? I can’t attract anybody to bring a family up here because they don’t want to get taxed at those rates either. And it occurred to me, we’re not competitive anymore. Over the last few years we’ve gone from 46 per cent personal tax on the high end up to 54.2. What the hell is that? Everyone has got to understand that we’re in a global competition here. The politicians that do that to us don’t get it. And so, I come out and say to myself, “Wow, that’s really depressing.” There is so much mediocrity, incompetence and sheer stupidity at the political level. Provincially, I’ve been very hard on Rachel Notley and Kathleen Wynne. I think there’s a lot to criticize and I’m happy to do it. Federally, I’m wide open to giving Trudeau a chance, but what I’ve seen so far is a fail. He leaves the country for 60 days, spends four billion dollars and doesn't create one Canadian job. I’m meeting those people that want those jobs and they can’t get them. I get to ten million people a week, that’s a platform. I’m going to be an open critic where I see mediocrity, stupidity or incompetence, and I see it all the time. My letter to Kathleen Wynne, she put a four and a half per cent tax on Ontario companies to create a Slush Fund. There’s no transparency. She’s going to extract the money and claims it's going to be for GreenTech. She claims it’s going to reduce carbon emissions, no problem. Show me it. Show me what you’re investing, show me the returns, let me see the portfolio, how many people are administering the fund, where’s the money going and, above all, you promised me emission reductions. Show me. Where’s that 1.9 billion going? So far nothing, nobody knows. So far, Ontario is 308 billion in debt. Now at some point, you have to pay for that. My attitude is, if you’re going to extract 54.2 per cent of my salary (more than half), you’re my employee. The politician works for me. Every Canadian citizen who pays taxes should feel that way. I demand performance and transparency. Give me both of those. I’m not trying to be overly critical. I have no ill will towards these people. I’ve never met her. But damn, I want some transparency. I’m tired of incompetence in the state. I’m tired of 308 billion in debt. I’m a pissed off taxpayer and I’m asking any other taxpayer who’s concerned to demand the same thing. I want to stop wasting money and I want the engineers who look for opportunities in Canada to say I’m staying in this country. Right now, they’re saying I’m checking out. This is a brain drain like I haven't seen since the nineties. This reminds me of Bob Rae’s Ontario where everybody just left. That guy has practically devastated the province with his politics.

Do events like the Panama Papers suggest a need for reform? Or are we simply operating within a system and getting upset at rules we make for ourselves?

I’m not an advocate for cheating on taxes. That’s not what I suggest. I have a very simple model. When you tax people past 50 per cent, then they start looking at alternate structures. We’re way past 50 per cent now and we’re talking about charging the country, at the federal level, 113 billion further in debt. We’re a small country, we can’t afford that. We can’t even spend that much money responsibly or efficiently. That’s going to be a huge mistake. It happened when Kathleen Wynne put on the two per cent on the higher end. She super taxed them. There were 29,000 Ontarians where she claimed she’d make 400 million more in revenue, but none of that materialized. All the accounting firms, all the lawyers restricted all those people. That’s how stupid policy like that is. You actually reduce revenues when you try and supersize people. They tried it in France. They went to 78 per cent and they lost all their revenue. They immediately two years later reverted back. Kathleen Wynne hasn’t figured that out yet. I do absolutely everything I can to shine transparency on that policy, regardless of who it is. I don’t care if it’s her or anybody else. We have a deficit of 308 billion due to blown up strategies in wind, and oil, and coal plants and stupid trains to airports that nobody rides, all that stuff. This is just bad management. I think we should finally say as Canadian taxpayers, why do we have to settle for mediocrity and incompetence? Where’s it written that I have to watch this happen? That’s why I’m getting motivated and maybe really what I’m interested in doing is getting involved in influencing fiscal and economic policy. There’s a lot of other stuff a government does that doesn’t interest me. But when it comes to making decisions about where the money is spent, I’m very good at that. I think I could bring together a team that would be a better steward of our money than what we have right now.

Will you run for office or do you see yourself as being more effective in the public realm with a platform to hold current politicians accountable?

Well the great news is I don’t have to choose for a year and a half. I’ve got lots of runway. I’m taking advantage of the fact that a lot of people want to talk about it. I’ve never seen an election cycle start this early in my life. That must be partly because of the way media works nowadays but also the angst that Canadian people feel around three things they can measure. No wage inflation: nobody’s making more in the last five years than they made five years ago. That’s a problem because we have no GDP growth. I think housing is going to go flat now, I don’t think it’s going to go up any more because there’s just no more downward pressure on rates and I think that’s a big asset on Canadians, and they have a lot of debt. The one that's the killer, that I think is going to bring down Trudeau’s government, is no jobs. If you’re 25 years old, you’re screwed. You can work as an intern for eight bucks an hour, if you’re lucky, for year after year living in the basement of your family’s home. But he has not solved the problem on jobs. Every time politician’s lips move, ask yourself, “did that create one increment of jobs in Canada?” If not, ignore it because it’s not adding any value to the economy and I listen to a lot of useless rhetoric. When he left the country for two months and spent four billion dollars on everybody else and didn’t help one Canadian 25 year old, I thought, “wow, that guy doesn't get it, he really doesn’t get it.” And when he comes back here and tries to spend 100 billion dollars and everybody else in the country says, “what are you doing?” I think that’s a fair question.

What does “power” mean to you?

I think I get my power base from the entrepreneurs that I help. I look at it this way, if you can help create a job, that’s power. You’re entitling another generation to build a business. To me, that’s the whole deal. I’m not interested in a lot of things that can’t manifest themselves in job creation. If you want to talk about creating a base of people to support you, it’s those that you have business with. You talk to any of my entrepreneurs and say, “does this guy spend his day helping you create your current job?” That’s the measurement. I consider myself powerful to the extent that I create jobs. That’s it, that’s the only way I want to be measured. I’m very proud of what I’ve done with my 20-plus companies now that are on my portfolio. We’re creating jobs, we’re competing, in some cases, globally. We’re making businesses, I’m making money. I’m not embarrassed to say that. I like that a lot. I’m have no problem with earning capital. I love the philanthropic side but the only way that works is if you’re creating business. Our standard of living does not come from the government, it all came from the private sector. My definition of power is creating jobs, that’s it.


Your off-camera and out of the office life manage to stay relatively private. How have you been able to maintain that balance?

I have a deal with my family. We get together every weekend somewhere in the world. I don’t plan on leaving any money to my kids. My deal with them is from day of birth to the last day of college, I’ll pay for everything, but when you get a job you’re done because my mother did that to me. But here’s my deal, if you have children, legitimate or not, I’ll pay for them from birth to the last day of college, and their kids. So that’s a very good deal. I am a big believer in family, so if my daughter or my son were to have kids, I’ll take care of all that for them. The point is every week, you’ve got to take those two days out. I get offered a lot of stuff on weekends, wonderful opportunities. But I just say no. This weekend I’m going to join my son, and my daughter is in New York, but we’ll all try to get together in Montreal. Every weekend is that way. That’s the balance. You can’t just never see your family, that's not worth it.

With all of your professional and political commitments currently in play, where do you find time for your personal pursuits?

It’s a balancing act. I was working last night on a new project. A good friend of mine suggested I look into it and I’ve been thinking about it. A guy named Don Allan, I’ve known for 40 years, is a famous producer here in Toronto. We used to shoot on film a lot of the intermission - Gump Worsley, Jean Béliveau, Ken Dryden. I have footage in 16mm cans that I own. It’s sitting in a basement. [Allan said] “Kevin, that stuff is invaluable. Why don’t you hire an editor, set up a team and go through every frame and let’s pull the frames using digital technology today, barrel scanning them, we can do high res Warhol-like images of a Gump Worsley interview, 30 years ago.I was working on this till 2 in the morning last night thinking about cool that will be for another exhibit. I’ve got one in New York on May 3rd, then it goes to Los Angeles and then to the Hamptons. I’m thinking as you do these exhibits and sell the work, I think a hockey thing for Chicago of all these iconic guys that I shot with Don and some other guys that used to work for Special Event Television, that would be a huge show. And we would obviously work with the images off the 16mm, it’ll be beautiful. That’s going to consume some time. When am I going to do that? I don’t know when. I talked to the Apple guys, they built me a system that's 24 terabytes in size now, it’s got a giant editing bay. We digitize the content and put it into these giant server farms and it indexes it. I hope to bring that one forward in the fall. You got to get 21 images, that’s a show. But I think it will be a good one.


Favourite deal on Dragon’s Den or Shark Tank?

I would to say it would be Wicked Good Cupcakes because I took a commodity. How do you differentiate a cupcake? Water, flour, butter — anybody can make one. We’re the number one cupcake in America now. That proved to me the value of the Shark Tank platform. The ability to take that unknown cupcake and make it number one. It’s the number one cupcake on QVC, it’s the number one cupcake in FedEx. It’s in Cinnabon retail locations. That’s the model. Pour the celebrity gasoline on the fire and build a business. Highest IRR [Internal Rate of Return] in Shark Tank history. It was a royalty deal, 45 cents a unit.

Favourite guitarist or band?

On the guitar side, I would have said that Jeff Beck was my favourite guitarist because of the early work. But then, after the Prince death, I went back and listened to the early works. That guy was a hell of a guitarist. People don’t give him enough credit for his skills. That guy can really shred a guitar. Go back and listen to his lead which [Eric] Clapton played originally on “While my Guitar Gently Weeps” at the [2004] Rock and Roll Hall of Fame awards. Shit. At the end of that lead, he threw the guitar on the floor and said, “I burnt that instrument out”. I’m conflicted now. I don’t know. I would put Clapton, Beck and Prince as my top three. I think band-wise, I listen to Steely Dan more than anything. So many great guitars and they’re on tour again.

Habs or Leafs?

The Leafs are an interesting business model. The more they lose, the more money they make. My theory for them is that they should be the only team allowed in the NHL to play without a goalie. When you go to a Leaf game, the reason it’s sold out every time is you know they’re going to lose, you just don’t know how they’re going to do it. Even when they’re up five-nothing, they still lose. These guys are the envy of the league. They make the most free cash flow and they lose the most. That’s incredible. They should be proud of that.

Legalization of marijuana?

We should do that for sure. It should be a federal mandate, not a provincial one. Totally regulated, taxed, take it out of the criminal hands and remove the whole distribution. Make the quality right absolutely as fast as possible. The trouble for me as an investor is I can’t invest in this. I can’t land in Texas and get arrested. So I need this thing to be a federal mandate in Canada. And we need to do it in the United States. Then, it’s going to be like prohibition. Look at Colorado’s experience with free cash flow and taxes, three times the estimates. A third of the population uses it now. People use this for all kinds of reasons. It is a medicinal product and people use it recreationally. Why have it so that it’s so powerful you’re walking around drooling? Give it to people in doses they know they are getting, modify the quality and I’m totally for it.

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