Dragons’ Den star Wes Hall’s new memoir tells his incredible journey from crushing poverty to the very top of Bay Street power.

On Sept. 27, 1985, a 16-year-old stepped off a plane from Jamaica at Pearson Airport and into a new life. Of the thousands of people arriving at Pearson on that particular Friday, no one could have imagined the impact that young Wes Hall would have on so many in his new country — through business, philanthropy and mentorships — especially considering the turmoil he had already experienced at such a young age.

Today, some 37 years later, Hall is one of North America’s most influential financial powerbrokers, beginning his second season as an investor on CBC’s Dragons’ Den and a major philanthropic force for his work with charitable causes. His personality has the gravitational pull of the Sun. Engaging, affable, outgoing, funny and ridiculously smart, Hall is the very definition of a “self-made man,” as told in his new memoir, No Bootstraps When You’re Barefoot, being released this fall.

All of this is a far cry from his humble beginnings of being born into abject poverty in Saint Thomas, Jamaica, in a home with a verbally abusive and violent mother and kicked out of the house at age 13 with no means to support himself. And no dreams or ambitions other than basic survival.

“I was always meant to be poor,” says Hall in a recent interview with City Life. “And the reason I was always meant to be poor was when you grow up in poverty, you’re not sitting there thinking, ‘One day, I’ll be eating steak and living in this fancy house in Toronto in the financial capital of the country and have the respect of all these CEOs.’ Think about the audacity of that thinking when you’re walking barefoot with no shoes. So, I didn’t have that ambition because I had no basis for it. As a child, I just wanted to survive.”

Hall not only survived but thrived, taken in by his beloved grandmother, Julia, who quickly became his saviour, mentor and centre of his world, pointing him toward a brighter future.

“My grandmother believed I was not an average kid,” says Hall. “I don’t know why she thought that, but she did and believed in me. I knew I had abilities, but I had no idea how far they could take me. But one thing is true — poverty has nothing to do with being loved.”

When young Hall stepped off that plane in Toronto, he was reacquainted with his biological father, new stepmother and new siblings. Following high school, he took a job in the mailroom of a Bay Street law firm where, despite the ribbing of his co-workers, he wore a suit to work so he could associate with the partners. Those conversations taught him so much and led to his interest in law.

After being educated as a law clerk at George Brown College, he worked in the legal division of CanWest until founding Kingsdale Advisors in 2002, a shareholder services and business consultancy. His reputation grew in the financial services sector, and, in 2006, he became a major player when his firm managed Xstrata’s purchase and takeover of Falcon-bridge, earning Hall his nickname, “The Fixer.” He also later established QM Environmental, an environmental remediation firm.

In 2020, Hall launched the BlackNorth Initiative, a trailblazing organization to end systemic anti-black racism in business, another example of his passion for people, his caring for the community and his driving ambition to make society a better place.

Writing his new memoir was emotional therapy for Hall, as he had to relive and face once again the traumas of his youth … losing his brother to murder and his sister to cancer. However, the memoir paints an amazing journey of incredible drive and the determination to succeed.

Now, a happily married father of five children, Hall’s success has allowed him to give back to his Canadian home as well as his native Jamaica, focusing on health care and education. He donates to the University of the West Indies by holding an annual fundraiser in Toronto to create scholarships for kids across the Caribbean. He also donates to the Hospital for Sick Children to bring doctors from Jamaica to Toronto for additional training before sending them back to his native country.

“When you come from poverty, you become a first responder,” says Hall. “And your job is to go back into poverty and pull as many people out as possible.”

Thousands step off planes every day at Pearson, and Canada is so fortunate to have people who, like Wes Hall, make such a difference in their new homes.

@kingofbayst