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In this edition of Chatter That Matters, Tony chats with Arlene Dickinson — a powerful, sought-after, dynamic female entrepreneur who isn't afraid to share her mistakes, setbacks and vulnerabilities.

At 31, Arlene Dickinson found herself as a single Mom, with little education, prospects or community, and lacking in self-confidence. What she did to create a life for her family, become the matriarch of Dragons’ Den, and give back by supporting the next generation of entrepreneurs is a story worth sharing. — Tony Chapman

Arlene Dickinson’s story may surprise you: a powerhouse female entrepreneur who has been named to Canada’s Most Powerful Women Top 100 Hall of Fame as well as PROFIT, and Chatelaine’s Top 100 Women Business Owners. It’s hard to imagine her as a stranded 31-year-old with only a high school diploma and no idea how to feed her family. In this episode of Chatter That Matters, she recounts her turbulent childhood, her decision not to go to university and the years after her divorce when she brought her kids to work on weekends as she built her first business.

Dickinson talks about her first book, Persuasion, which was written as a means of reaching a wider audience of women who were struggling to find a place in the business world and her second best-seller All In, which normalizes the messy, difficult journey through entrepreneurship and offers help in navigating its unique emotional and personal demands. Upfront about her mental health struggles and a believer in sharing her vulnerabilities, Dickinson discusses how she pulled herself out of a particularly low point and turned her life around, a story told in her third book, Reinvention.

Sharing thoughts on the importance of resilience (the iron will that gets you through mistakes), what success means to her (living a life of purpose), and her drive to give back, Dickinson’s chat with Chapman confirms that success is earned through hard work and perseverance and can really only be achieved when you’re true to yourself, follow your ethics and dare to look failure in the eye.

To listen to this show, go to, download Chatter That Matters at I HEART Radio (or wherever you get your podcasts) or tune in Fridays at noon to these radio stations:

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  • Or Fridays at 8 p.m. on BNN Bloomberg, CFTE 1410 Vancouver