For much of his childhood, Wes Hall lived in a tin shack in a rural part of Jamaica where he was raised by his grandmother, Julia Vassel.

A plantation labourer, Vassel worked long hours chopping sugarcane in the searing Jamaican heat, and on her own managed to raise 10 grandchildren, including Hall, as well as an adult daughter with special needs.

So, when Hall moved to Toronto in 1985 at age 16 to live with his father, he took inspiration from his grandmother’s example of steadfast determination as he navigated his new life. “My grandmother’s strength and wisdom became my lifelong mission to emulate,” he says. “I refused to take no for an answer, and I refused to accept defeat.”

That relentlessness has served Hall well. Today, he is a prominent figure on Bay Street, an investor and television personality on CBC’s Dragons’ Den and a philanthropist dedicated to tackling systemic racism in business and society. Last year, he became the University of Toronto’s 35th chancellor.

Hall says he’s humbled by the magnitude of his new position and honoured to serve as an advocate and ambassador for an institution committed to empowering the next generation of leaders and changemakers drawn from all segments of society. “The University of Toronto, in my opinion, is the biggest source of upward mobility in Canada,” says Hall, who began his term as chancellor last July, succeeding Rose Patten.

In particular, Hall cites the diversity of U of T’s students, with representation from 178 countries and territories, and the university’s extensive student financial supports – which include a pledge that no domestic student admitted to the university should be prevented from studying because of a lack of financial means – as key elements that are setting the stage for a brighter future. “Think about the impact that will have on our society moving forward,” he says. “This is why I wanted to be a part of this university. This is where change happens.”

Early challenges

For Hall himself, change didn’t come quickly or easily. At 18, he moved out of his father’s home and worked menial jobs to get by – including as a dishwasher and a poultry company’s chicken wrangler. Those tough jobs fuelled Hall’s drive to find something more rewarding, which led him to a position as a mailroom clerk at business law firm Stikeman Elliott in Toronto. He worked toward a law clerk certificate in the evenings and then took a job aligned with his studies at media giant CanWest Global. He went on to land his first managerial role at CIBC Mellon.

As a young Black man managing 11 employees in customer service and support, many of whom were much older and white, Hall said earning the respect of his team was far from straightforward, teaching him the importance of leaving his ego at the door. “I don’t necessarily want to be the smartest person in the room. I want to be the person who figures the room out and understands how people there operate,” he says.

He describes one especially difficult employee – a man in his mid-50s who had been in the company for three decades, and didn’t take kindly to having to report to a 25-year-old.

Hall says he made a concerted effort to seek out the man’s advice, lean on his experience and make him feel important and valued – eventually earning his loyalty and respect: “I figured out what made him tick.” The man – once one of Hall’s biggest detractors – became a loyal ally.

Years later, Hall would confront doubters again when he came up with a business idea for a service to provide strategic advice to public companies on matters related to corporate governance, shareholders and transactions. He pitched it to his then-employers. “They thought it was nuts,” he says. Undeterred, he approached banks for a loan so he could build the company on his own. “And they go, ‘That’s so wacky, we’re not going to fund that.’”

Eventually, Hall persuaded his wife, Christine Hall, to agree to borrow $100,000, using their house as collateral. He used the funds to set up his firm, Kingsdale Advisors. That was in 2003. Today, Kingsdale is regarded as one of Canada’s top shareholder services and advisory firms, while Hall is one of the most respected power brokers in Canadian business.

Creating opportunities

In recent years, Hall’s reputation has expanded beyond executive boardrooms into living rooms across the country as a sought-after investor on CBC’s Dragons’ Den, where he says he’s constantly inspired by the creativity and drive of Canada’s entrepreneurs (and is known to viewers for his sharp fashion sense and flashy footwear). “Many people come up with business ideas, but entrepreneurs act on them – even far-fetched ideas – despite the naysayers telling them they can’t do it,” Hall says.

He notes that he’s passionate about using his platform to uplift people from underrepresented backgrounds.

In 2020, following the killing of George Floyd by a white police officer in Minneapolis, Hall set up the BlackNorth Initiative, a non-profit organization based in Toronto, with chapters in Alberta and Nova Scotia, that aims to help end systemic anti-Black racism in corporate Canada. It provides scholarships for students, mentorship and networking for entrepreneurs, and a home ownership bridge program to help Black families own a home.

“Home ownership allowed me to start Kingsdale and create the value that I have today,” Hall says. “I want to create that same pride and opportunity for as many underserved families as possible.”

Hall also assists entrepreneurs through WeShall Investments, a private equity firm he founded in 2023 that takes a special interest in supporting ventures led by people from racialized groups.

‘You have to be a fighter’

Hall is mindful that his own success story – and that of other immigrants, people of colour and people from underprivileged backgrounds – shouldn’t be used to downplay the scale of inequality in society. “How many others are out there who have been deprived of fulfilling their true potential?” he asks.

As the first Black chancellor in U of T’s 198-year history, he says he hopes he can serve as an inspiration to students. “I think just my presence in the role so far has had a positive impact,” he says, “because it allows young Black kids and young kids of colour to go, ‘Wait a minute, this is possible.’”

A staunch believer in U of T’s mission to empower people of all backgrounds to flourish, Hall says he urges students to adopt a positive, forward-looking attitude to overcome obstacles.

He cites as an example Shirley Cheechoo, a Cree actor, visual artist and filmmaker, who has said she prefers to be recognized as a “warrior” rather than a “survivor” of Canada’s residential school system. She made the remark during a keynote address at a U of T event to mark Orange Shirt Day and the National Day for Truth and Reconciliation, which Hall attended. “I appreciate the sentiment that ‘I was successful in fighting, and it’s now my job to show people that in order for you to go through things successfully, you have to be a fighter,’” Hall says.

I am never too busy to put my hand up and say, ‘I want to be a part of change.”

Last October, at a reception at Hart House to celebrate his installation, Hall said he had been asked by well-wishers if he was not too busy to add U of T chancellor to an already long list of responsibilities. He responded by recounting the example set by his grandmother, who raised him and nine other grandchildren on a plantation worker’s wage.

“One of those kids that she worked so hard to raise is asked in the future to be the chancellor of Canada’s top university – and one of the top in the world – and that kid says, ‘I’m too busy.’ Could you imagine?” Hall said.

“I am never too busy to put my hand up and say, ‘I want to be a part of change.’”