Mention the name “Kevin O’Leary” and responses usually involve raised eyebrows and some guarded allusion to “sharks” or “mean dragons.”
These reference two reality TV shows where he’s featured – CBC’s long-running hit Dragons’ Den (entering its eighth season) and ABC’s Shark Tank (going into season five.)
Others know him as “the guy from Lang and O’Leary,” the CBC-TV news program, The Lang and O’Leary Exchange, where he pits his conservative principles against Amanda Lang’s liberal leanings as they discuss economic issues at home and abroad.
Sure enough, in an interview, O’Leary lives up to his reputation as a capitalist shark, willingly addressing macro- and microeconomic issues with a flourish for which he has become famous. Take the size of government, for example:
“I’d like to shrink government by about a third. I think what’s happened – and there’s lots of evidence of it – is the government has grown too big. The way I look at it, for every dollar the government spends 33-1/3 cents is wasted, one third, because much of what they do is not market tested.
“The best way to solve our economic problems would be put less money through the government grinder, which is extremely inefficient. They’re constantly building bridges to nowhere – power plants to get disassembled – wasting billions of dollars per year on really stupid things.
“All of the great successes in Canada are not attributed to government initiatives, they’re attributed to entrepreneurs who’ve created great companies over the years. And we need to actually stimulate more of that by lowering taxes and getting government out of it.”
And when it comes to his money, he stresses it’s serious business all the way.
“I don’t do investments to make friends. I do investments to make money. If you want to make friends, buy a dog. If you prefer the kumbaya let’s-hold-hands-and-sing-songs, that’s somebody else. That’s not me.”
That’s the Kevin O’Leary we all think we know. But converse for a while longer and it emerges that he is equally enthusiastic about his other passions, including music, wine and photography.
In fact, photography was an early career choice for a teenage O’Leary. But his step-dad talked him out of pursuing it, telling him it “wouldn’t make money.”
Nevertheless, the camera has been ever-present in his life and he’s about to turn that hobby into a money-maker, not for himself but for budding young entrepreneurs.
“Over the years I’ve amassed a massive portfolio of images that I’ve taken all around the world. So I’m going to curate a showing of my photography and sell the work for charity, to support teenage entrepreneurs. This fall I’m going to show my first 25 curated images and I’m excited about it.”
He’s setting up a foundation to run the project, targeting entrepreneurial students from underprivileged families for assistance. Candidates will be chosen by teachers and finalists will be celebrated on Dragons’ Den and Shark Tank.
If the project is successful, O’Leary says it will accomplish two goals. “Finally I’ll achieve the goal I’ve always wanted – to be a photographer and make money doing it. And, secondly, to support entrepreneurs as a charity. To me, that’s a great cause.”
Another lifelong passion is also turning a profit for O’Leary these days – his burgeoning line of fine wines.
O’Leary’s step-father introduced him to fine wines, from a young age, taking him on tours of Europe’s wine regions and introducing him to some of the world’s finest varieties.
“In our family it’s just part of our lives,” he says. “I’ve got five wine cellars. I buy wine futures and I trade them. So, it’s beyond a hobby; it’s just part of who I am I guess. And, I always wanted to bring out an O’Leary wine.”
Working with Vineland Estates owner Jim DeGasperis and vintners Allan and Brian Schmidt, O’Leary launched his brand with a 2010 Cabernet Merlot that won six awards, including Best Value at the 2012 InterVin International Wine Awards, one of only 10 red wines, from more than 1,000 tasted, to receive that distinction. It became the number-one-selling VQA red in Ontario.
“It’s the beginning of what I think is going to be a big business for me. I’m going to pursue it aggressively. I’m very excited about it. I didn’t think my name would carry a wine brand. But I’m happily wrong.”
Realizing his wine dream is just one of the benefits that have risen from his television exposure.
It wasn’t something he ever expected, as he built his enterprises from the first SoftKey educational-software company, launched from the basement of his Toronto home, to the massively successful The Learning Company, focusing on software to enhance youngsters’ reading and math skills.
His early experience with film was behind the camera. Both his undergraduate and MBA theses were produced on film. And his first professional enterprise, Special Event Television, produced sports-related shorts and documentaries and is noted for launching Don Cherry’s Grapevine.
But his career as a television personality, particularly on Dragons’ Den and Shark Tank, is something he describes “the most incredible journey I’ve ever had as an entrepreneur” and “a dream come true.”
“I have this massive platform and now my job is to find occasions to apply it and build businesses.”
He cites the example of a Boston cupcake company he invested in through Shark Tank. It was doing a respectable $16,000 a week but, following the airing of the Shark Tank episode, shot up to $280,000 in sales and now surpasses $700,000.
Says O’Leary: “They’re becoming one of the top shippers of cupcakes in America. So imagine, I’m looking at it now as an investor entrepreneur saying to myself, ‘what an incredible platform. What else can I do with this?'”
There have been many such highs in his broadcast career, which took off with the Lang-O’Leary show. That grew out of a Business News Network panel show called Squeeze Play, featuring Liberal politician Brian Tobin and a young business journalist, Amanda Lang, daughter of Otto Lang, long-serving Liberal MP and cabinet minister in the Pierre Trudeau government.
Today, O’Leary describes the collaboration as “a television marriage that’s outlasted pretty well any other,” and calls it “unprecedented in Canada. I don’t believe there’s a television partnership that’s lasted as long as ours.”
The reason for its success: “Amanda Lang is the most attractive communist on television. There’s no doubt about that. I really believe that I’m put there to protect Canadian viewers from the direction she wants to take that show. The way I look at it is that I’m defending the rights of capitalists in Canada and I think that’s why the show works.”
Never-leery O’Leary weighs in:
On his fellow Dragons
I’ve gone through many new dragons, or dragonettes, and each person, each entrepreneur, brings a different perspective. And they bring a different sector.
For example, we never used to do a lot of food deals on Dragon’s Den until (David) Chilton (the newest dragon and publisher of the “Looneyspoons” cookbooks) arrived. Chilton really understands the retailing of food products. From him we’ve started to understand the opportunities in that space. I’ve started investing in those deals because I’ve learned from Chilton.
And Arlene (Dickinson, owner of Venture Communications) brought all the information about advertising.
When Brett Wilson (Saskatchewan native and investor in energy and agriculture sectors among others) was doing the show, we were doing a tremendous amount of energy deals, as he came from the oil patch.
Each one of these people has tremendous experience in something. So as they come and go they bring their own stamp and they leave their legacy.
On achieving life balance
The challenge with being an entrepreneur is trying to balance time. You need time to yourself, you need time for your family. And that has always been a challenge. I have to admit I could have been a better father particularly in the years when my kids were young.
(In) that kind of life, there is no balance. It’s not possible in today’s world to have balance if you’re trying to be an entrepreneur because it’s a globally competitive environment that you have to work incredibly hard and you have to sacrifice some period of your life to achieve success later. If the goal is to achieve freedom – that’s what wealth provides – then I’ve achieved that goal but I’m not going to say it wasn’t without sacrifice.
I don’t know what retirement really means. I guess what it means for me is, the activities change. I’ll be doing something but maybe it’ll be something different.
I publish books, I do the wine business, the mortgage business, the mutual-fund business and TV. And really the challenge is balancing all those. Maybe one of those falls off, maybe television goes away or radio goes away.
But I just get up in the morning and do what’s on the schedule and things just appear. I try and enjoy the ride. I know it’ll end one day. It is what it is.