Q and A with former Dragon and Canada’s favourite billionaire entrepreneur Brett Wilson

If you keep up to date with Canada’s business landscape, a name you’ll hear often is Brett Wilson. Brett is one of Canada’s most notable entrepreneurs who is a businessman just as much as he is a philanthropist and who is best known as a three-season panelist on CBC’s Dragons’ Den. 


Wilson was the first graduate to receive an MBA in entrepreneurship from University of Calgary – a move that was an indicator of things yet to come before he knew it. After a career shift from engineering and receiving a taste of the investment banking field, Brett co-founded an investment banking advisory firm called Wilson Mackie & Co.and Canadian stock brokerage firm FirstEnergy Capital Corp that set him on the path he is today.

However, Wilson’s savvy business nature isn’t the only thing that makes him inspiring.  It’s his view on philanthropy which he views not as an obligation but an opportunity. From shaving his head for kids’ cancer to climbing Mount Kilimanjaro for Alzheimer’s research, Brett is known for his hands on approach.

Wilson wrote  “Redefining Success: Still Making Mistakes”, a book that was released in 2012 sharing his story of contagious drive, ability to spot opportunity and how he tripped over a multitude of misguided priorities along the way. As Brett explains in his book, his priorities had to be set straight. After all, what is the point of achieving monetary success when your family and health are suffering.

A Calgary native, Brett was recently in town for Toronto International Film Festival 2014 where Affluence Avenue had a chance to catch up and get some of Brett’s insights for our readers.


Affluence Avenue:      Let me start out by asking you – what did you want to be as a kid?

Brett Wilson:      
        I wanted to be bigger. I was small for my size. And my dad was 6’3’’ so I wanted to be tall. People would say “well you’ll be bigger when you are older”. I’m 57 and I’m still not big and tall like my dad so I keep wondering when is this going to happen?! So that was one. The other and maybe a little more relevant, I wanted to be a scientist. I didn’t know what an engineer was at the time and I defined myself as sort of lab coat scientist.

Affluence Avenue:     
Interesting. By the way, going back to your first point… I’m 5’11’ and reached that height before everyone else so slower growth isn’t always bad!

Brett Wilson:              (laughter) The girls don’t want to be tallest first.

Affluence Avenue:      No, we don’t.

Brett Wilson:              Everyone wants something else.

Affluence Avenue:      So, was there a defining moment when you knew you wanted to be an entrepreneur?

Brett Wilson:              When I went to university from the small town; I really had two choices: engineering and business. I was being pushed to engineering versus business. After I started the engineering program. I very quickly discovered that there was in fact a program called an MBA and that I can do an engineering program and I can do an MBA in only 2 years. Also when I was doing my engineering degree I started my MBA by studying financial news. I received Financial Post for $17 a year. It came twice a week and I can remember Tuesdays and Fridays getting back checking the mail and immediately grabbing a newspaper and sitting in my room laying down on the floor to spread out the newspaper and reading it literally cover to cover. It wasn’t until 10 years later when I finished my MBA, I was working in downtown and the knowledge I had of from reading paid off. I may not have gone to a prestigious business school but I could run circles around most because of my street knowledge. I hire based on street knowledge.

Affluence Avenue:      Did you have any business mentors along the way?

Brett Wilson:              Mentors no, role models yes. I often suggest to people to not worry too much about mentorship and more about being influenced by role models. I use the example of a local business owner in my home town – one of my mom and dad’s best friends. He was an entrepreneur, a politician, a senator, he owned farmland, he owned development properties. I loved that he was actively engaged and did so many things. I would also say that Richard Branson.

Affluence Avenue:      Oh I love him.

Brett Wilson:              You know I don’t pretend to be Richard Branson but I will tell you that I appreciate and really admire his use of extraordinary marketing and memorable marketing for his brand as a point of differentiation.

But again I mix and blend the two words mentor and role models because I think too often young people come up and want to be mentored and so I ask the question, “Have you read my book?” They say no. So I tell them, “Well, why don’t you read that first before you ever approach me. Be ready with some questions.” It suggests a complete lack of forethought and when you look at the tools that are available, there’s lots of interviews and stuff on me so until you’ve absorbed all that… I mean people want to be mentors as a shortcut. With the internet you can be a role model by almost anyone.

Affluence Avenue:      Yeah, it’s true.

Brett Wilson:              Things are out there whether it’s Richard, whether it’s Warren Buffett.

Affluence Avenue:      What I personally love about Branson is that he’s the anti-corporate entrepreneur.

Brett Wilson:              I admire a more entrepreneurial style than a more office style. I sometimes feel out of place in some board settings in terms of how I look but not in terms of intelligence or contribution. It’s pretty hard to intimidate me. This is not arrogance, its just confidence and there’s a big difference between the two.

Affluence Avenue:      How was Branson when you met him?

Brett Wilson:              It was fascinating. I was on his island talking about international terrorism. He is engaging and enjoyable as you might guess.

Affluence Avenue:      In your book you discuss how your definition of success has changed – how do you feel that it has changed from decade to decade from 10-50?

Brett Wilson:              It’s interesting you would talk about it in decades because I really do think about my life in decades. I can actually separate it. At 10 I’m this little guy, I skipped a grade, I started to see the world through big great eyes. From ages 10 to 20 I was picked on because I was smart and I was small. By the time I finished university at roughly 20 years old I came into my own and when I suddenly switched over into engineering, I had a roomful of geeks where I belonged. I was a geek, I was small and I was in a roomful of geeks who were of all sizes and shapes.


Affluence Avenue:      Very true.

Brett Wilson:              Frankly ages 20 to 30 are a little bit remorseful for me. I didn’t spend a lot of time with my family because they wouldn’t stop smoking and I wouldn’t start to tolerate it. And so it consisted of a lot of phone calls, lots of quick visits…. When I turned 30, my mom died of lung cancer like her mother – same day, same hour, same hospital. It was a lot of emotional confusion at the time.

Affluence Avenue:      Yeah.

Brett Wilson:              At the time of my mom’s funeral, the family gathered as they would and I can just remember everyone hanging around smoking and drinking. I couldn’t have felt more disconnected. So I quit drinking that day.

Affluence Avenue:      An epiphany.

Brett Wilson:              I quit by choice. So that was in my 30s, I worked through my 30s and 40s and right now my 50s has been very much a harvesting moment where as 60s would be distribution. I would be giving a lot of my wealth and my years back into the community. I don’t want to be just writing checks. I think that’s an application of opportunities to make a change.

Affluence Avenue:      Do you have any professional advice for somebody who is striving to achieve the same level of success as you?

Brett Wilson:              Let’s start with challenging level of success definition. If all you want and define the metric of success in shallow and superficial traffics of wealth – don’t worry about your health, don’t worry about your friends, don’t worry about your family, just work. There’s dripping doze of sarcasm but it’s really important in your 30s to look at where you want to be over the next decade, not five years but what do you do in your life in the next 10-20 years and set priorities

Affluence Avenue:      Yeah.

Brett Wilson:              I mean, if you want a family and not children raised by two nannies… That’s an individual choice but it’s a lost opportunity in my opinion.

Affluence Avenue:      Interesting.

Brett Wilson:              The whole messaging then is really to think a bit about where you want to be. There’s nothing wrong with wanting more. What do you want in terms of wealth, how comfortable do you want to be? There’s no judgment. If all you want to be is a billionaire, well that’s pretty superficial, but again that’s your choice. I would also argue that it’s important to want to be emotionally intellectual. I made a huge priority of that. I love travel. I have been to more than 65 countries and of those 65, 55 have been with my children.

Affluence Avenue:      Travel is the only thing that makes you richer!

Brett Wilson:              (laughs)

Affluence Avenue:      So, did you try to nurture entrepreneurial nature in your children?

Brett Wilson:              That’s going way back in time. My great grandfather was one of the original entrepreneurs in Western Canada.  He was a farmer. He was a member of the legislature. He was the man. He owned the lumbar yard. He owned the tool shop or the hardware store and he was also a senator. He was the first senator in Western Canada. I never knew him. But there was this legend of this guy in my life. And my dad when I was born was literally repossessing cars and you know he wanted to become a sales manager. My mom is a social worker. To my mind we didn’t really have an entrepreneurial mindset in our house. They were employees. When I raised my own kids I have never told anyone to go in any one direction but rather encourage them to develop passion and values. I have said to my kids if you want to do what I do you got to get two degrees and here’s the four to choose from, arts, engineering, law, commerce. So, I have a daughter who’s just finished her PhD in neuroscience in the world of psychology and in the world of eating disorders. None of those sound particularly entrepreneurial until you find out that she actually wants to do a series of courses and market them as a business. So here’s someone who’s taken a completely non-entrepreneurial path and twisted that. I have another daughter who studied engineering. She didm’t like it and she’s now studying to be a holistic nutritionist. Her job right now is she’s doing private cheffing for families in Vancouver. She’ll make their meals and bring to them. It’s awesome. It’s ordinarily entrepreneurial.

Affluence Avenue:      Interesting.

Brett Wilson:              With my son, I encouraged him to look at a couple of classes when he asked me about studying and maybe working for me someday. I said well why don’t you do a couple of these online courses on coursera.org. In fact I sent him one that I looked at and I said here’s an online course that’s 12 hours, let me know what you think. That was on a Friday. I talked to him on Monday and he said it was great. I said what are you going to do. He said “well, I’ve done it.” He looked at it all 12 hours over the weekend. He loved it.

Affluence Avenue:      What can institutions do better to encourage the same level of entrepreneurial freedom?

Brett Wilson:              I’m extraordinarily passionate about believing that universities, trade schools, the Ontario College of Art and Design – I don’t care where you are studying, what you’re studying, if you are going to be a welder or a farmer….

Number 1: You must study marketing. It’s your differentiation. If you don’t know what post purchase dissonance is you haven’t studied marketing. The value of brand. The value of goodwill. The value of making advertising memorable. It’s one thing to make it interesting and amusing. But will it be remembered.

Number 2: The study of entrepreneurship. I don’t mean to study the tools of being an entrepreneur. I need case studies. Entrepreneurial case studies where people can be inspired. I’m not saying everyone should be an entrepreneur. But Ray Kroc started McDonald’s when he was 57. Colonel Sanders was in his 60s when he got his chicken recipe all sorted out. It’s not about when but if you plant the seeds you have a high probability of creating options. This country was formed by the original entrepreneurs, the hunters, the farmers, the fur traders, the Hudson Bay Company was entrepreneurship at its finest because it was individuals making changes,.

Number 3: The last thing and in fact an entire chapter in my book is dedicated to this is philanthropy and charity. Looking at philanthropy in a strategic way and some people say no charity is just about giving, you are getting back first. What more can we do? What can you do that is strategic?

I often argue that one of the greatest wastes of life in this world so far is a kid named Justin Bieber. I would love to spank him. I would love to coach him. I would do both if he was available but I would love to sit with him for half an hour and say Justin there’s three things that you can do in the world: money, leadership and endorsement. Everyone of us is capable of giving but not all of us can do what I call “celebrity endorsement”. He had 45 or 50 million followers on Twitter and these kids adore him. If he recorded a video and sold it for 10 cents… well thats $0.10 times 5 million is $500,000. Justin you could be raising $500,000 a week, $26 million a year for spending a day in studio. I use Justin as a metaphor for a lot of wasted opportunity.


Affluence Avenue:      If you had $100 right now what would you invested it in?

Brett Wilson:              Marketing.

Affluence Avenue:      Why?

Brett Wilson:              Whether it’s a book or an online course. These kind of question come up often with people saying “I want to start a business I only have $100 or $1000”. Well study marketing and then secondly go get a job where you are paid to learn. What I mean by paid to learn is change your perspective. Any job is learning. If you haven’t worked in the industry in which you want to start your business for several years don’t ask me for backing because you are not going to get it. In fact don’t even ask me for encouragement because you are not going to get it. Quite often the business schools will have these entrepreneurship programs. Start measuring how quickly students start businesses after school. I don’t want to know the one year and the two year rate. I want to know five year and the 10 year and the 20 year numbers.

You know I worked as an investment banker. I never thought I was going to be an entrepreneur. I thought I was going to be an investment banker. But I became a very entrepreneurial investment banker by virtue of time. There’s many ways to start a business. It’s not always by having a lifelong dream to be an entrepreneur. It’s not the case at all. But somewhere in my background the seeds of entrepreneurship had been planted so that when the time was right we opened a window at home.

This is me. Again I didn’t go down the path planting and cultivating this course of action.

Affluence Avenue:      What do you think makes a successful sales person?

Brett Wilson:              Sometimes in the world of negotiation I think the most important thing you do is understand all the metrics of what creates the gaps. Often in a deal there can be 10 elements of what’s important to each side and if there’s a gap in any one of, you don’t have a deal. Bridging the value gap. I have taken a few negotiating courses.

Affluence Avenue:      Any that you recommend?

Brett Wilson:              No, there’s none that I remember.

Affluence Avenue:      What do you think makes a successful people manager and leader?

Brett Wilson:              You know there are so many definitions of what makes a leader successful. Who is successful? Is it someone who leads a successful business or is it someone who leads a happy business or is it someone who leads a happy life and business? I have a business partner who isn’t in the office more than a day a week. He has one of the most successful businesses I know. It really comes down to – how do you define success?

Lighting Round

First job:
Pumping gas and sweeping the grounds at a gas park.

One luxury item you can’t live without:
Oh I hate to think that it’s my sports car so I’m going to go to my laptop.

Favourite place to vacation:
With my family.

Favourite book:
I like Malcolm Gladwell’s work and he’s got half a dozen books you can name. He’s one of the few authors that I have taken the time to read.

Favourite hobby:
Golf. You know I golf 10 times a year but I love it.

Favourite city:
I got to say the Calgary. It’s my base camp.

Favorite Toronto restaurant:
Nota Bene.

After a long day at work you go home and?
Walk my dog.

Words to live by?
If it’s not fun, stop doing it.

If you met Justin Bieber at a party what would you do?
I would like to ask him if I could spank him…. But it really comes down to I would like to ask him if I could have an opportunity to coach him. I would love to have just one session.


Thanks Brett!


Founder of AffluenceAvenue.com - Toronto's First Luxury Lifestyle Guide focusing on travel, food & drink, arts, culture, fashion and business & career advice.

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