Anatomy of a Leader: Arlene Dickinson

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Arlene Dickinson today is recognized as a visionary entrepreneur with an incredible track record of success – an iconic Canadian business leader with a high profile through her work and as a dragon on the popular CBC TV show Dragons’ Den.

Her journey to get to this position in life and in business has not been an easy one over the years. But a vision, dedication and perseverance have always been in the forefront of her road to success.

“For me, I think it’s been a function of always wanting to make the most of what was in front of me,” she says. “Because we grew up very poor and without very much, we were raised to be very grateful for what we had and we were raised to believe that anything is possible.

“I think immigrants just have a different view on what hard work can do. So I always knew that if I worked hard enough I could put food on the table and I could take care of myself. I have a really strong work ethic. I try to do the right thing. It doesn’t mean I’m always successful at doing everything right but I try to do the right thing.

“And I think my success has come because when I listen to people, and when people share their stories with me or share their dreams with me, or talk about what they want to do, I genuinely listen. I think I’m authentic and I think my authenticity has really been the key to my success because I care about what people think, I care about what they want, I care about what they need and I want to help them do whatever they need.”

Image: Arlene Dickinson

Dickinson was born in Germiston, South Africa, just outside of Johannesburg. Her father chose to move to Canada as an electrical engineer and Dickinson was three years old when she came to Edmonton initially. A few years later the family moved to Calgary when she was around six years old.

“I didn’t have any university. (After high school), I started to work. I worked in PR for a little bit and worked in retail for a little bit. I graduated when I was 16 and left home because my parents ended up getting divorced so I didn’t really have a home to stay at,” she said.

“So at 16 I left home, went to rent a place, got a job in retail then got a job in PR for a little bit and then got married at the age of 19. So I was like literally out of school, worked for a couple of years, fell in love and got married.

“I got a job at CFCN TV in sales when I got divorced. Got fired from that job and I had met one of the partners at Venture (Communications) at the time and they said they would make me a partner if I would come and work for free basically. Sweat equity. And I had nothing else I could do. I had no other opportunity in front of me so I took the gig and went to Venture.”

About nine or 10 years later, she bought the partners out.

“In marketing, you have to be a student of pop culture and I was fascinated by people. Always have been fascinated by people. So I’ve always been an observer of people. And I think what made me good at marketing was understanding that people have dreams and they have fears,” said Dickinson.

I think people only hire you for marketing because you can do one of two things. You can help them build their dreams or you can help them stop their pain . . . I grew up in a fairly troubled family, got divorced when I was young. So I became a really great listener and a great observer of people.

“And I think those street smart skills made me really good at marketing. I liked it because I understood it and I think I was good at it because I had come from a place of feeling unheard and unseen in my childhood. So it was this kind of ability to think about pop culture and to think about what people really wanted and not put the attention on me but really focus on making other people successful. So my whole thing with marketing is how do you make somebody else really successful and if you do that you might be lucky enough to be successful yourself but the purpose of it was always, how do I help other people build their business. That was kind of where it started and why I liked it so much because you could help other people.

“It was either going to be that or a social worker.”

Reinvention by Arlene Dickinson
Reinvention by Arlene Dickinson – Photo by Dustin Fuhs

Dickinson is Founder and General Partner of District Ventures Capital, a venture capital fund that invests in innovative companies in the food & beverage and health & wellness sectors. She is also the Co-Managing Partner of Believeco:Partners, an independent Canadian-based owner, operator, and builder of the foremost marketing, communications, and engagement agencies in North America.

Beyond her business ventures, Dickinson is a sought-after speaker, three-time best-selling author, and philanthropist. She is widely recognized for her role as a Venture Capitalist on the hit television series, Dragons’ Den, where she currently has starred for over 15 seasons.

Dickinson has been included in Canada’s Most Powerful Women Top 100 Hall of Fame, PROFIT and Chatelaine’s Top 100 Women Business Owners and the Marketing Hall of Legends. She’s a recipient of the Pinnacle Award for Excellence and the Queen Elizabeth Diamond and Platinum Jubilee Awards. She has received numerous other awards and accolades – both for her work as an entrepreneur and her many philanthropic efforts, including acting as an ambassador for Second Harvest. She has served for many years as an Honourary Captain in the Royal Canadian Navy and has received honourary degrees from Mount Saint Vincent University, Concordia University, Saint Mary’s University, Olds College, Northern Alberta Institute of Technology and University Canada West.

Before she joined Venture, she had a couple of other jobs. At one of those jobs she met a guy who was into investing in the stock market. That piqued her interest even though she had little money to invest. While learning about the stock market, she met his broker who taught her the best lesson she ever learned about investing – don’t be greedy, pigs get slaughtered which were his words. Always leave some money on the table for the next guy. And you can’t go broke taking a profit.

Arlene Dickinson at Carlton University SOAR Student Leadership Conference (Image: Chris Roussakis)

The stock market was interesting to her and because she liked people so much she started to think, as she got more successful in her business, more about it. At the time, one of her staff came to her and said they were going to Thailand to start a travel adventure company and would she lend them some money to do it.

“I had never done angel investing before. I thought it was interesting. Sure. I really liked him. I really trusted him. I knew he would pay me back. It was $30,000. I really didn’t have $30,000 but I lent it to him anyhow and he paid me back over time,” said Dickinson.

“And I just got the bug. It made such a difference to him. It was the difference between him starting his business and not starting his business. Because he paid me back on time and he always kept me informed, I thought there’s something there. I was doing little investments on the side. I was investing in things on my own with angel investing. And the market. Of course, investing in myself and in the business and growing the business and making the deals, acquiring companies. They came and asked me to be on the show and that literally was the start of my serious investing.”

Dickinson walks a lot to relax. If she is dealing with a problem or trying to sort through something, she goes for a long walk. Traveling and reading are also big interests of hers outside of work.

Image: CBC Dragons Den

In a recent post on LinkedIn, Dickinson offered her crash course on resilience:

  1. Everyone is not going to like you, and that’s ok, so get comfortable with liking yourself because yes, it will feel hard when not everyone likes you.
  2. You don’t need to seek or have other people’s validation of your accomplishments in order to be accomplished.
  3. Be like that wind up toy that when it hits the wall it reverses and goes happily in a different direction.
  4. The easy road doesn’t exist so stop searching for it and get comfortable with navigating a road full of potholes.
  5. Sometimes when you reach your goals you still won’t feel satisfied. Use that sense of needing more to help you accomplish more.
  6. Resilience and optimism are co-dependent.
  7. Know your values because people will constantly test them and you’re going to need them when they do.
  8. You can be confident and have loads of self doubt at the same time. Focus on growing even the smallest glimmers of confidence that are in you and leveraging the fear, no matter how big, to propel you forward.
  9. Find the joie de vivre because each day will always bring a challenge if you’re trying to grow.
  10. And here’s the best lesson: Challenges are opportunities.
Mario Toneguzzi
Mario Toneguzzi
Mario Toneguzzi, based in Calgary, has more than 40 years experience as a daily newspaper writer, columnist, and editor. He worked for 35 years at the Calgary Herald covering sports, crime, politics, health, faith, city and breaking news, and business. He is the Senior News Editor with Retail Insider in addition to working as a freelance writer and consultant in communications and media relations/training. Mario was named as a RETHINK Retail Top Retail Expert in 2024.

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