Two older, worn human hands resting on a weathered wooden work surface, with shirt sleeves rolled up.

Our story.

OUR STORY.

StreetLight Traders didn’t just recently begin as a trading community. It began much earlier than that. While studying journalism, I learned to ask questions, look beyond the obvious and search for the story underneath.

But when it came time to build a career, technology presented an opportunity. I took it. What I thought might be a short detour became the next twenty-five years of my life.

THE CAREER I DIDN’T PLAN.

I worked my way through the technology industry, eventually moving into leadership and doing many of the things you’re supposed to do when building a career: take on more responsibility, move up the ladder, solve bigger problems and keep moving forward. Technology gave me a good career and a stable life. But like so many of you may be feeling right now, eventually I burned out. After twenty-five years, staying simply because I’d already invested twenty-five years no longer seemed like a good enough reason to spend the next twenty-five doing the same thing.

So I looked back at where I’d once wanted to go and took a chance on myself. Journalism — with a focus on photography. Walking away from a stable career to pursue the arts wasn’t necessarily the sensible choice. It was a huge risk. And I was extremely fortunate to have that risk pay off.

I met people who took an interest in what I was doing, gave me opportunities, taught me things I didn’t know and helped show me a path forward. Those relationships gave me the chance to photograph, write, travel and tell stories I never could have predicted when I decided to leave technology.

It taught me something else, too. Starting again doesn’t mean starting from zero. You bring everything you’ve learned with you. Eventually, I would start again one more time.

A working film camera, photographic contact sheets, reporter’s notes and black pen sharing a desk with a modern laptop.

ANOTHER REINVENTION.

Growing up, I was always interested in the markets. I loved news, politics and the economy. I wanted to understand how those things worked and stay connected to what was happening in the world. But trading was never part of the plan. I wasn’t the kid who grew up dreaming about working on Bay Street in Toronto. I came to trading much later in life — and quite by accident.

Like a lot of people discovering this world for the first time, I found an industry overflowing with complexity, confusion and people promising they had the answer. Trading courses. Mentorships. Trade signals. Indicators. Strategies. Platforms. Gurus. Discords. Predictions. Opinions. Everybody seemed to have an answer. And frequently, the answer was available for a price.

So I fell back on something familiar. Old-school grit. When I didn’t understand the machine, I took it apart. I learned. Experimented. Made mistakes. Overcomplicated things. Simplified them again. Tried different markets, different tools and different ways of trading.

And eventually, the question stopped being: How do other people trade? And became: What kind of trader am I actually comfortable being? Becoming honest with myself about the answer changed everything.

WHY STREETLIGHT?

I grew up in a generation where you went outside in the morning and disappeared for the day. There were no phones tracking us. No messages asking where we were. Things were simpler. There was one instruction: Be home before the streetlights came on.

Those lights meant something. They were a boundary. They told you where you were, and they told you when it was time to move.

As I’ve moved through my fifties, I’ve found myself becoming more nostalgic about those times. I find myself missing the way things used to be. Not everything was better. It wasn’t. And StreetLight isn’t an attempt to pretend otherwise.

What I miss is the familiarity. The common language. Common experiences. Common cultural references. That feeling when somebody mentions something from your childhood and you don’t have to explain it because they were there as well.

There are also things from that time that I think are worth carrying forward. Curiosity. Work. Responsibility. Learning how things worked. Making mistakes. Figuring things out. And occasionally rubbing some dirt in it and getting on with your day.

StreetLight isn’t about rejecting the present either. We use plenty of technology every day. We’ve built software. We use AI. We trade electronic markets with modern tools. That’s the combination I want StreetLight to represent: Old-school grit. Modern execution. Take what still matters from where we came from and combine it with what’s possible for our future.

Neighbourhood kids lingering beside their bicycles on a late-1970s Canadian summer evening as the amber streetlights come on.

TRADING CAN BE A LONELY BUSINESS.

That’s also another reason I’d like StreetLight to become a community: a place for accountability. I want a place where I can show up, trade in front of other people and hold myself accountable to the rules I said I was going to follow.

Because trading alone can be incredibly isolating. You sit in front of a screen making decisions with your own money and your own emotions, and there’s nobody beside you telling you to stop when you’re about to do something stupid. I know what my rules are. Knowing them and following them haven’t always been the same thing.

Making this public creates accountability for me as well. I’m not standing on the other side of the screen pretending I’ve solved trading. I’m doing the work alongside everyone else. And I started wondering how many other people were sitting alone in their own offices doing exactly the same thing. So why do it alone?

WHAT DO YOU WANT THE NEXT CHAPTER OF LIFE TO LOOK LIKE?

That question has become more important to me as I’ve gotten older. There comes a point when you realize you probably have more years behind you than you have ahead of you. I don’t find that depressing. I find it clarifying. Time matters more. What you do with it matters more.

And maybe you’re somewhere around the same point. Maybe the career that once made sense doesn’t anymore. Maybe you’re thinking about retirement. Maybe you’re trying to pay off debt, create some security or become more independent. Maybe you want to build something of your own. Maybe you want to leave something behind.

Or maybe you’re simply asking: What do I want the next twenty years of my life to look like?

StreetLight isn’t about Lamborghinis or Ferraris. That’s not what I’m chasing. I’m interested in something much less glamorous and much more valuable to me: Independence. Security. Options. Freedom.

Trading isn’t necessarily the answer to all of that. Neither is starting a business. Neither is changing careers. There probably isn’t one answer. For me, trading is part of it. Building something of my own is part of it. Continuing to learn is part of it. And doing some of that alongside a community might make the whole process a little less lonely.

A man with a chart laptop aboard a practical sailboat, moored beside two neighbouring boats in Toronto Harbour at blue hour, with the CN Tower beyond the water and a warm dock streetlight illuminated.

THIS IS STREETLIGHT TRADERS.

StreetLight is where all of those chapters finally meet. Journalism taught me to investigate and explain. Technology taught me to build and solve problems. Trading continues to teach me patience, discipline and how expensive it can be when I ignore either one.

Over time, those worlds began to overlap. I explored automation, algorithms and algorithmic trading. I built indicators and experimented with ways technology could help remove friction from execution. But the deeper I went, the more obvious something became. Technology could help me execute a decision.

It couldn’t give me patience. It couldn’t stop me from chasing a move. It couldn’t make me respect risk. It couldn’t make me wait. The machine wasn’t the thing I needed to automate. I was.

Eventually, some of those experiments became the tools we now call TapeDeck and Cassette Deck. Not because software was the destination. Because they solved problems we encountered along the way.

But StreetLight is bigger than the tools. And it’s bigger than my story. My goal is to build a serious trading community for people who want to do the work. A place where we can trade together, learn together, build things, ask questions, challenge each other and hold ourselves accountable. A place with some nostalgia and familiarity for those of us who remember when the streetlights really did tell us it was time to come home. And a place for people thinking seriously about the next chapter of their lives to meet others doing the same.

We’re going to trade here. We’re going to build things. We’re going to take things apart and occasionally put them back together with a few pieces left on the bench. We’re going to make mistakes. And hopefully we’ll get a little better along the way.

I don’t have the ending to this story. That’s kind of the point. We’re building the next chapter together.

The first streetlight is ahead. And the lights are coming on.

Roger’s handwritten signature