Wes Hall and New Book, No Bootstraps When You're Barefoot

Before Wes Hall became the king of Bay Street — and the newest and first Black dragon on Dragons’ Den — he was one of 13 siblings living in a tin shack in Jamaica with his grandmother. Wes shares his incredible rags-to-riches story, as well as a profound message of hope and change, in his new memoir, No Bootstraps When You’re Barefoot — available in stores today.

After moving to Canada when he was 16, Wes worked his way up from a humble position in a law-firm mailroom to the boardrooms of Bay Street through his intelligence, curiosity, and his unique ability to see opportunities that others often miss.

Well aware of the many roadblocks in his path — including racism, injustice, and a lack of privilege — Wes always believed he could walk along any cliff edge without falling. In his new book, he shows how he fostered this resolve while exploring his childhood| and recounting the milestone successes and failures of his career. He also reveals not only how he stopped himself from falling but learned to thrive in a system set against him, and how he has dedicated himself to bringing his family and his community along with him.

In June 2020, Wes launched BlackNorth Initiative (BNI) to challenge Canadian businesses to end systemic racism, something that plagued his career early on. He and his highly esteemed team of experts are collaboratively improving the lives of millions of Black Canadians by opening doors that were previously shut.

CBC Dragons Michele Romanow, Wes Hall, and Arlene Dickinson

Wes joined Dragons’ Den in 2021 with the goal of creating more opportunities for BIPOC entrepreneurs. Season 17, which premiered in September, marks his second season in the Den, where he’s joined by seasoned Dragons Michele Romanow and Arlene Dickinson.

Equally known for their business expertise and celebrity status, Wes, Michele, and Arlene are available for brand partnerships including spokesperson roles, media appearances, digital content, and more. Contact us for more information.

Wes recently spoke with Maclean’s magazine to discuss his upcoming season as well as his new memoir.

Maclean’s: You’ve said that No Bootstraps When Your Barefoot isn’t supposed to be like other typical how-I-made-it, instruction-manual memoirs. How so?

Wes Hall: When you read those kinds of books, it’s like, “Okay, here’s the step-by-step.” There’s nothing in my book that specifically shows readers how I became successful; it’s about the struggles I went through. The things I experienced as a child defined the person that I became: the father, the husband, the philanthropist and the businessperson. Without those experiences, would I have started BlackNorth, an organization that helps other underserved people? Would I have been a good dad? Even though those times were painful, I learned some important lessons from them. The book is about taking chances and never feeling sorry for yourself.

Maclean’s: How have your life experiences shaped the way you approach contestants on Dragon’s Den — particularly Black contestants?

WH: If all the Dragons look the same, they’re not worrying about diversity. But once the Dragons look different from each other, people start to think that maybe the people in front of the panel should be just as diverse. I’ve supported a number of BIPOC entrepreneurs, even outside of the show. One is a company called BIPOC Executive Search, which develops leadership in communities of colour.

Maclean’s: Kevin O’Leary was the adversarial pot-stirrer on the show. What’s your Dragon schtick?

WH: My thing is to support the underserved—entrepreneurs who go to the traditional funding avenues to get capital and are essentially laughed out of the joint. A lot of the Dragons say to the contestants, “You’re not an entrepreneur.” If you have the guts to start a business, you may not be as successful as someone else, but you are an entrepreneur. I’m not a mean Dragon.

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