The Current

Wes Hall faced racism as he climbed corporate ladder. He wants to make sure others don't have to

Wes Hall was raised by his grandmother in a tin-roof shack in Saint Thomas, Jamaica, before moving to Canada as a teenager and working to become one of the country’s most successful corporate leaders.

Hall remembers colleague saying 'In spite of the fact that Wes is Black, he's doing well'

Wes Hall is a Canadian businessman and the newest member of CBC's Dragon's Den. (CBC )

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When he was 12 years old and still living in Jamaica, Wes Hall remembers his mother beating him so badly in public that a passing one-legged man tried to intervene.

"He said to my mom, 'You should stop beating that boy. One day that boy could be the one that you rely on to look after you,'" Hall, now a leading Canadian businessman, told The Current's Matt Galloway.

"I remember saying, 'Is he right? Am I going to be somebody? Am I going to be special in the future?'"

A black boy in a blue collared-shirt, a black belt with a big circular buckle and blue and white plaid, flared pants looks down, eyes averted from the camera. On top of the photo, the text reads "Wes Hall, No Bootstraps When You're Barefoot, My rise from a Jamaican plantation shack to the boardrooms of Bay Street."
Hall's memoir charts the sacrifices that it took to achieve success. (Random House Canada)

Hall went on to become a leader in Canada's corporate landscape, as founder and executive chairman of Kingsdale Advisors and one of the stars of Dragon's Den on CBC. In recent years he has also become a prominent anti-racism advocate. 

His mother did stop beating him that day, he said, if only to give "a verbal lashing to that man."

But he wants kids today to know that they too can overcome the hardships they might be facing.

"There are kids and young people going through exactly that right now.… I want to tell them that, 'Hang in there. It's going to get better,'" he said.

Hall tells the story of the sacrifices that made him a success in his new memoir, released earlier this month, called No Bootstraps When You're Barefoot: My Rise from a Jamaican Plantation Shack to the Boardrooms of Bay Street.

He and his two siblings were abandoned by their mother as very young children. Along with some of their cousins, they were raised by his grandmother, Julia Vassel, in a tin-roof shack without electricity or running water in St. Thomas, Jamaica.

Vassel would rise at 4 a.m. daily to prepare food for Hall, his siblings and their cousins, before heading to work on nearby plantations at 6:30 a.m. At one point she was supporting 10 children on her plantation worker's salary. 

"I can't talk about my story now without talking about the sacrifices my grandmother made to get me here," Hall said.

A man and older woman stand outside, in front of a tin-clad shack.
Hall with his grandmother, Julia Vassel, in Jamaica in February 1999. (Random House Canada)

When he was 11, Hall's mother returned and took him away to live with her. Though he initially felt like he "won the lottery," his mother quickly became physically abusive. 

"It's not just the physical beatings, it's actually the mental beatings that she gave me … how she referred to me and, you know, the names she called me," he said. 

"I felt absolutely useless. I just felt like, she tells me, I'm a nobody."

His mother threw him out at 13, and he lived on his own for the next three years. 

In 1985, a 16-year-old Hall moved to Canada to join his father in Toronto. He got his high school education, and then found a mailroom job at a law firm downtown on Bay St.

Entering the heart of the city's financial district showed Hall the kind of life that he wanted to lead, but he didn't realize at the time that "there were no Black people in those corner offices, or in any of the offices for that matter."

A father and three children pose for a picture outside. One of the children is dressed for  his first day of school, with a backpack.
Hall taking his son Darian, right, to his first day of school, Sept. 2000. His other children Keana and Brentyn are pictured left. (Random House Canada)

Having grown up in Jamaica, Hall was used to Black people being in positions of power in all walks of life, from school principals to local business leaders to police officers and judges.

"To me, being Black was never an obstacle to being successful. Being poor was an obstacle, but being Black wasn't," he said. 

It was only years later — as he was already enjoying success in a vice president role on Bay St. — that he overheard a conversation between the two most senior people in the company's Toronto and New York finance departments.

"The guy in the U.S. said, you know, to the Canadian guy, 'In spite of the fact that Wes is Black, he's doing well,'" Hall remembers.

Change takes time, commitment 

Looking back, Hall began to realize racism had played a role in earlier parts of his career. But he now says that while these realizations were difficult, they didn't have a lasting impact on his psyche. 

"It certainly didn't hurt as much as when I was hearing it from my mother. So she's certainly hardened me for the life that I would live here in Canada," he said.

LISTEN | Wes Hall's message to young people graduating in the pandemic

As his success grew over the years, he's worked to try to make sure other Black, Indigenous, and people of colour don't have to face the same challenges he did.

In 2020 Hall founded the BlackNorth Initiative, asking Canadian business to tackle systemic racism in their organizations. The move followed global protests over the murder of George Floyd by Minneapolis police officer Derek Chauvin.

More than 200 Canadian organizations signed on, but a recent investigation by the Globe and Mail found that only a minority had made significant strides in hiring more Black employees, or elevating them to executive levels. 

Hall said about 40 per cent of signatories to the initiative are committed to its ideals, and have plans in place to achieve them.

A further 30 per cent want to do something, but don't know where to start, which is why his organization has created a "playbook" to give them direction.

WATCH | Why Wes Hall felt compelled to speak about systemic racism

Wes Hall compelled to speak about systematic racism after George Floyd’s death

2 years ago
Duration 2:32
Canadian businessman Wes Hall had never spoken up about the systemic racism he’d experienced until the death of George Floyd. Hall says he felt a duty to speak out and make things better for the next generation.

The remaining 30 per cent might have signed on performatively, to allay public scrutiny, he said.

"I'm not going to focus on those 30. I'm going to focus on the 70 per cent that can make meaningful changes within their organization to affect me as a Black Canadian," he said.

The work of BlackNorth is helping those companies to make the cultural changes needed for BIPOC employees to thrive, which will take time "to filter into the culture of the business because it didn't exist before," he said.

"What we're building here at BlackNorth is not really to change my life right now —  I'm too old for that," he said.

"It's to change my kids' lives, so that when they graduate from university and they get into the workforce, they don't have the struggles that I had."


Audio produced by Julie Crysler and Joana Draghici.


For more stories about the experiences of Black Canadians — from anti-Black racism to success stories within the Black community — check out Being Black in Canada, a CBC project Black Canadians can be proud of. You can read more stories here.

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