INTRODUCTION

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.