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(Editor’s Note: This article is based on Season 1, Episode 3 of Diverse Dividends, CFA Society Toronto’s video podcast series featuring Wes Hall.)
When Wes Hall immigrated to Canada from rural Jamaica in 1985, he could not have imagined how far he’d travel: Chancellor at the University of Toronto, founder and CEO of Kingsdale Advisors, Dragon on CBC’s Dragon’s Den, and passionate activist through the BlackNorth Initiative. Along the way, however, a humble mantra has guided him: Take one “baby step” after another, embrace each failure, and never rest on your laurels.
The power of baby steps
Solution-oriented leadership
For Hall, genuine leadership is assuming responsibility for each outcome. “When things go wrong, point no fingers. Instead ask, ‘What decision led us there, and how do we fix it?’” That problem-solving attitude has been rewarded whether he’s leading clients through proxy battles or advising prime ministers on trade wars. When you are a leader and something goes wrong, take the time to reflect on why a decision was made and to create a plan to make a better decision next time without pointing fingers. It’s important to fix what went wrong or pivot. “Blame kills momentum. Accountability fuels progress.”
“Blame kills momentum. Accountability fuels progress.”
If you can land an elephant, it will be so much easier to catch a gazelle Twenty-two years ago, Hall created something that he didn’t see in the Canadian landscape: a space for activist investors. After having his vision turned down by investors, he placed a mortgage on his house and Kingsdale Advisors was born. Vision and ambition have been cornerstones of Hall’s career, and his first “elephant” client was Sun Life Financial, which had the largest retail shareholder base in the day. Since then, his successes with Sun Life drew other clients in.
That win became our CV,” he says, proving that sometimes you need to go big or go home. “Once we’d won Sun Life’s trust, every other door opened.”
Own your seat at the table
When you’re the only person in the room who looks like you, “It’s a message to say, ‘well, you don’t belong here,’” says Hall, acknowledging the societal influence of imposter system. “Use the spotlight,” he advises, “and remind people precisely why you belong.” If he had let seeing people who didn’t look like him in positions of power affect him, he never would have seen the success he enjoys today. “I always say that my Blackness is my superpower,” Hall laughs. “People automatically underestimate your abilities until you start to show what you’re capable of doing. By the time they figure it out, you have the upper hand.” Explaining how to reframe mindset around imposter syndrome, Hall explains, “When we want to get to the next level, we automatically assume that everyone there is better than us… until we get there and realize it’s just like society: some people are smarter, and others are not.”
Understand the value of unconventional champions
Hall recalls that one of the best jobs he ever had was when he was 25 years old and working at Canwest Global. The General Counsel was a 35-year-old white man who was incredibly hard on him, and he didn’t understand why. “I couldn’t understand why he was so tough on me. And he explained it to me later on: ‘I saw your talent, and when I didn’t see you living up to it, it was disappointing to me because I know life is going to be hard for you, so I’m making it tough for you… When you leave this place, and you will because you’re ambitious, you’re going to be okay and withstand all the storms coming your way in the future.” Many such mentors have been allies to Hall over his career, despite looking nothing like him, focusing their efforts on him realizing his potential and inspiring him to do the same.
Legacy: The power of generational thinking
Nowadays, victory is not quantified by Hall in terms of accolades but in the world he leaves behind for future generations. “I’m no longer just thinking about my children, but about their children,” he asserts. “How can I do better to bring life improvement for those who are coming?” He describes the difference between the Canada he came to in 1985 at just 16 years old, with his father, who worked in a factory and fought to bring him opportunities. He asserts that
every generation should think one to two generations ahead and consider how they can make it better as their own personal legacy. It’s a call to construct much beyond individual ambition. Whatever you have can be gone in minutes, or even seconds, so focus on what’s important Hall emphasizes the value of your principles, family, and close relationships.
“I kind of live my life on the basis that, whatever I have, it can be gone within minutes or seconds. But there are certain
things in your life… your principles, your family, and really close relationships. It doesn’t really matter if you’ve lost your
wealth. It doesn’t matter if you lost your influence. Those people will always be there to support you. And those are the people that I focus my life on.” If you have these things, it doesn’t matter if you’ve lost a prestigious position, wealth, or influence.
their own personal legacy.
Wes Hall’s journey from the mailroom to the pinnacle of Canadian finance is a testament that greatness is rarely bestowed: it’s earned one step at a time. From rising analyst to seasoned partner, his insights to finance and investment professionals seeking to advance their careers is:
➥ Think generationally. Build for those who come next. Use your difference. Your uniqueness is your advantage.
In every challenge and triumph, Wes Hall’s story exemplifies how perseverance, vision, and community can transform both personal journeys and the broader industry.
Diverse Dividends is CFA Society Toronto’s new video podcast series from The Analyst, which aims to explore the rich mosaic of the finance and investment industry. Each month, Diverse Dividends features candid, in-depth interviews with industry leaders across the finance and investment world as they share their insights on mindsets, strategies, and lessons that drive their success.
Why listen?
Where to find us
- Podcast apps: Subscribe on Apple Podcasts, Spotify, SoundCloud, or YouTube
- Online: Stream full episodes at cfatoronto.ca
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