I Learned to Run a Business
by Leading a Gang
Before the boardrooms and brand decks, I was leading people in the wrong direction and learning the right skills. This is the origin story I usually keep quiet.
There is a version of my origin story I could tell. The one that sounds cleaner. Starts with a camera, a passion for storytelling, a vision for what media could do for brands.
That version is true. But it is incomplete.
The fuller version starts earlier, in a chapter most people in my position keep quiet. Before Canadian Tire, before LCBO, before any of it, I was leading people in the wrong direction and learning the right skills.
What the streets actually teach you
Nobody says it this way, but leadership has nothing to do with a title. You either know how to move people or you do not. How to read a room. How to build authority without a manual. How to hold a group together when the pressure is on.
I learned all of this early. Organizing people. Reading personalities, emotions, egos, the energy underneath what someone says. Thinking two moves ahead. Getting people to believe in something and move as a unit.
The direction I was pointed in was wrong. The capability was real. And eventually, that distinction became everything.

High Class
High Class and the pivot
In 2008, I built my first real organization. Not a company yet. Not a brand. Something in between. I called it High Class.
High Class was not about clothes, status, or image. It was about mindset. We worked with young creatives, and what we taught was simple: you are worth more than where you are. Choose better. Raise your standards. Surround yourself with people who pull you forward, not back.
It gave people something to belong to. Identity. Pride. Direction. And in building it, I discovered something I had not expected: the skills I had been using in the wrong direction were exactly the skills needed to do something meaningful. I just had to choose where to point them.
That was the pivot. Not a moment of inspiration. A decision. The same energy, redirected.
The lessons leadership actually requires
What I built across both of those chapters taught me five things that no business school articulates clearly.
Clarity is leadership. If you are confused, the people around you will be too. Confusion spreads faster than vision.
Conviction is contagious. Doubt is also contagious. A leader who hedges loses the room. People follow certainty, not perfection.
Vision is the north star. Without it, you are managing. With it, you are building something people will sacrifice for.
People are not logical. You have to navigate emotions, egos, and energy. The most brilliant strategy fails if the humans inside it do not feel seen.
People need to belong. Not just to an organization, but to something that gives them meaning. If you can provide that, they will go further than you expect.
Leadership is neutral energy. It will amplify whatever direction you point it toward. The real work is not becoming a leader. It is choosing what you are willing to lead people into.
High Class was the seed. Corex Creative is the tree. The same foundation, the same principles, now powering a company working with Canadian Tire, LCBO, CSA Group, and the City of Toronto, while still doing what I started in 2008: helping young creatives find confidence, structure, and a reason to believe they belong in rooms that were not built for them.
Full circle is not a metaphor. It is a methodology.
The question is not whether you have leadership ability. Most people do. The question is what you have been pointing it at, and whether you are willing to be honest about the answer. If you recognize yourself in the early part of that story, the misdirected energy, the capability with no clean place to land yet, that recognition is not a warning. It is a resource.
The direction can change. The capability stays.
Written by
Dwayne Holness
Filmmaker, brand strategist, and creative director. Founder of Corex Creative, a Toronto-based creative media agency building cinematic brand stories for founders and thought leaders.
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