Skip to main content Skip to search Skip to search

Biography & Autobiography Business

No Bootstraps When You're Barefoot

My rise from a Jamaican plantation shack to the boardrooms of Bay Street

by (author) Wes Hall

Random House of Canada
Initial publish date
Oct 2022
Business, Entrepreneurship, Discrimination & Race Relations
  • Hardback

    Publish Date
    Oct 2022
    List Price

Classroom Resources

Where to buy it


From one of Canada's most successful business leaders, the founder of the BlackNorth Initiative and the newest and first Black Dragon in the Dragon's Den comes a rags-to-riches story that also carries a profound message of hope and change.

Wes Hall spent his early childhood in a zinc-roofed shack, one of several children supported by his grandmother. That was paradise compared to the two years he lived with his verbally abusive and violent mother; at thirteen, his mother threw him out, and he had to live by his wits for the next three years. At sixteen, Wes came to Canada, sponsored by a father he'd only seen a few times as a child, and by the time he was eighteen, he was out of his father's house, once more on his own. Yet Wes Hall went on to become a major entrepreneur, business leader, philanthropist, and change-maker, working his way up from a humble position in a law firm mailroom by way of his intelligence, his curiosity, and his ability to see opportunities that other people don't.

When people expected his thick Jamaican accent, lack of money and education, not to mention the colour of his skin, to shut down his future, Wes was not to be stopped. He is still overturning expectations to this day. Well aware of racism and injustice, his lack of privilege and the other roadblocks to his success, Wes has always believed that he can walk along any cliff edge without falling. His book teases out and shows how he fostered that resolve in himself, exploring his childhood and the milestone successes and failures of his career in order to share not only how he stopped himself from falling, but survived and thrived, and then dedicated himself to bringing his family and his community along with him.

Now, with the founding of the BlackNorth Initiative, Wes takes aim at ending systemic anti-Black racism. It's a huge goal, but one he's tackling with heart, soul, smarts, and every connection he's made in an extraordinary career that's taken him to the centre of the Canadian establishment. Throughout his life he's resisted sinking into despair or getting lost in anger; now he wants to tell truth to power and pave a path forward.

About the author

Contributor Notes

WES HALL, the executive chairman and founder of Kingsdale Advisors, is one of North America’s most influential powerbrokers and Canada’s preeminent leader in shareholder advisory services. Hall also founded KSS HoldCo, a private equity company mostly supporting entrepreneurs who are Black, Indigenous, or people of colour. He has many other business interests, including hospitality, real estate, financial services, construction, advisory services, and consumer products. An instructor at the Rotman School of Management at the University of Toronto, he teaches Black Entrepreneurship & Leadership, a first-of-its-kind course in North America. The founder of the anti-Black racism initiative, BlackNorth, he is also one of the investors on the hit TV series Dragon’s Den. His podcast, Between Us with Wes Hall, features conversations on systemic racism with leaders of colour.

Excerpt: No Bootstraps When You're Barefoot: My rise from a Jamaican plantation shack to the boardrooms of Bay Street (by (author) Wes Hall)


I started with nothing. And it wasn’t even the “dollar and a dream” kind of nothing, because, early on, I didn’t have either of those. I was born in rural Jamaica—St. Thomas, the poorest parish on the island. I grew up in a plantation worker’s shack with no elec­tricity. Our only running water was the nearby river. I went to school barefoot because the only shoes I had were saved for church and special occasions, and I got made fun of for that, because I was the poor kid even in a place where everyone was poor. I didn’t dream of the life I have today because I couldn’t even imagine it. I expected to work long hours at a tough job for very little pay, like my grandmother did, and to never leave my hometown.
By most measures, today I am a successful man. After founding my first company, Kingsdale Advisors, in 2003, I professionalized the shareholder services industry in Canada, and I have since worked on many of the biggest deals in this country’s history. I employ hundreds of people, live in a big house, drive a nice car and come home to a beautiful family—my wife, Christine, and our five children. In 2021, I joined the cast of Dragons’ Den, a CBC reality show built on entrepreneurs’ dreams of financial success. I am the first Black Dragon in the program’s sixteen-year run.
This book is largely about how I got from my beginnings to where I am now. How I survived the disadvantages that came with being born into poverty in the “wrong” part of the world. How I escaped abuse and abandonment as a child. How I over­came all the obstacles faced by a newcomer to Canada. How I climbed to the top of the corporate ladder as a Black man, with missing rungs and everyone else taking the elevator. I hope anyone dealing with the same kinds of challenges and systemic barriers will read this and be inspired. I want to show you that just because the system is designed to hold you down, that doesn’t mean it will succeed. And I want you to know that you are strong enough to drop your shoulder and run through the walls they put between you and your goals—for now, that may be the only way to reach them.
But I also want to make one thing clear: this is not an instruction manual. What I’ve accomplished should not have been possible. My aim in describing how I navigated a system created to limit Black achievement isn’t to draw a map for those coming up after me; it’s to prove that no one should ever have to make the same journey. In recent years, I have dedicated myself to that cause, going public with my own experiences and founding the BlackNorth Initiative, a project aimed at ending systemic anti-Black racism. BlackNorth’s CEO Pledge, a detailed and benchmarked commitment to combat unconscious bias and racial discrimination, has been signed by the leaders of more than five hundred of Canada’s biggest companies, but in the course of securing those commitments and others, I’ve heard the same thing again and again from some of the most power­ful people in the country: “I just didn’t know.”
As a Black person, it can be hard not to roll your eyes at that excuse. Systemic racism is not exactly new. I’ve spent my entire career walking into boardrooms to find I am the only Black person there, and it’s frustrating to think of top-level executives looking out over their organizations, seeing no Black faces and never wondering why that might be.
But it’s hard to wrap your head around something you’ve never experienced, and white supremacy is both foundational in our institutions and sneaky. That’s how it protects itself—it hides in processes and attitudes that can seem innocuous until you look at their results. And much of its impact is invisible unless you’re the one taking the hit.
Our culture celebrates people who seem to have pulled them­selves up by their bootstraps. But that phrase was originally meant to describe an impossible task. When I look back at my life so far, I am immensely proud of what I’ve accomplished. I was lucky, yes, but I also worked my butt off and found ways forward when it felt like the whole world was trying to beat me back. I think the story of how I did that is a good one, if you’ll forgive the immodesty, but I’m not writing it here so it will be celebrated. Holding a story like mine up as proof that the obsta­cles society stacks against Black and Indigenous folks and people of colour are surmountable further entrenches those obstacles. It asks those impacted by racism to find ways to just deal with it, to succeed despite it. That is ridiculous. It’s unfair. It’s asking people to do something as impossible as pull yourself up by your bootstraps, and some of us don’t even have boots—we start out barefoot.
I hope that my story makes all that clear. And I hope it inspires change.

Editorial Reviews

Advance Praise for No Bootstraps When You're Barefoot
“Mr. Hall’s book, as honest and raw a tale as you’ll encounter, is a story of triumph in the face of incredible adversity.” —The Globe and Mail

“Wes Hall’s memoir is extraordinary: a rags-to-riches story that is also a powerful testament to the spirit that helped him overcome poverty, abuse and racism. He has bared not just his feet, but his fears, his aspirations and struggles, showing us that to come from ‘nothing’ shouldn’t be a barrier, but to do ‘nothing’ to break down those walls is never okay.” —Arlene Dickinson

“I was gobsmacked by the pure, undistilled truth of Wes Hall’s No Bootstraps When You’re Barefoot. One of my favourite expressions is “a rising tide lifts all boats.” Wes Hall is not a boat at all. He is the rising tide.” —Ben Mulroney

“Wes Hall gives form and insight to an otherwise invisible man’s legacy. Invisible to those partially responsible for rendering him unworthy, undeserved and unseen, Wes emerges as a cultural beacon. The story of Jamaican success in the diaspora is familiar, but here we see it through a unique lens: the lens of someone who defied all odds to become wildly successful in a foreign country, in a way that nobody has before him. His book is another of Wes’s achievements that should be celebrated and shared across the globe.” —Kardinal Offishall

“It’s said that many successful people get a head start by being born on third base. As a child, Wes Hall didn’t even have a ticket to the stands, yet he’s achieved beyond his wildest dreams. His life story is an inspiration for us all, and especially for anyone faced with adversity, poverty and racism.” —Kirstine Stewart

Related lists