The Leadership Lessons That Last

Hey Team!

We’re officially full-force into the holiday season… and if you believe in Santa, he’s starting his rounds tomorrow. I’ve been back in Vancouver for a few days and it’s been action-packed. Most notably, I had the chance to watch the Vancouver HYROX competition on Sunday, which was incredible.

I ran into several friends, including a few loyal readers of this newsletter. Congratulations to everyone who stepped onto the start line this past weekend. Proud is an understatement. Watching you compete in that arena was something special. The energy was electric and it felt like the perfect way to enter this holiday week: grounded in camaraderie, excitement, and that unmistakable human spirit that shows up when people choose to challenge themselves together.

A Mental Edge

While watching HYROX, I ran into a long-time friend, Jay, and his wife Kim. And by “friend,” I mean someone who played a foundational role in my life. I’ve known Jay since I was 15. In my late 20s, I joined his company, and we eventually became business partners in a business I spent over a decade helping build.

When I joined, the business was hovering around $1.5–2M in annual revenue. Shortly after, things took off, with sales nearly doubling year over year for multiple years. With that growth came long days, real pressure, and more lessons than I could have imagined.

From the outside, Jay and I probably looked like Batman and Robin. We were early pioneers in a brand-new cannabis industry, established for nearly a decade before billions of dollars started flowing in. Behind the scenes, though, it wasn’t always smooth. We challenged the U.S. government and Homeland Security, lost corporate bank accounts more than once, and navigated a shotgun clause with an original co-founder… all while riding the wave of something exhilarating and incredibly demanding.

Standing beside Jay this weekend, watching his daughter race, felt like a full-circle moment. We caught up, shared what life looks like now, and went our separate ways. But what stayed with me was a deep sense of gratitude for that chapter of my life.

That era taught me what resilient leadership really looks like. What it means not to walk away from something good just because it’s hard. Sometimes the right move is to close a chapter. But sometimes, you fight for it. This was one of those times.

Jay and I were often like oil and vinegar. Different personalities. Different upbringings. Different ways of operating. Looking back, though, that tension is also what made us effective.

A couple days ago, I shared a small piece of this story on Instagram. It landed deeply, especially with Jay. I realized I hadn’t fully expressed how grateful I was for him and for the journey we shared. That chapter shaped who I am today. He felt the same.

It’s never too late to express gratitude. To tell someone the role they played in your life. Sometimes the simplest words, shared unexpectedly, land the hardest.

From The Field

Watching the athletes compete at HYROX, I’d be lying if I said I wasn’t a little envious. Getting on a start line, shoulder to shoulder with peers, still brings nerves, and a kind of excitement that training alone can’t replicate.

That said, my decision not to race HYROX was intentional. I’m laser-focused on one goal: running a sub-3 marathon in 2026. Anything that pulls me away from that doesn’t make the cut. As it turns out, that decision came at the right time. I’m currently dealing with a minor hamstring tendon strain.

This is where a quiet advantage comes into play. I book physical therapy sessions at Myo before something goes wrong. I go monthly, but even one session every six months can make a meaningful difference. Over thousands of miles and three pro-division competitions last year, this is my first real setback. When the strain started to show up, I already had a session on the books. We addressed it immediately.

Progress isn’t just about pushing harder. Sometimes it’s about protecting momentum.

Quick Reminders Before You Start:

Wishing you all a safe and happy holiday season. Whether you’re in a season of ease or navigating something challenging, there’s always something to be grateful for. I’m making a conscious effort to stay present through the moments, conversations, and connections over the next few days.

It’s never too late to express gratitude, and there may be no better time than now. The most unexpected messages often have the biggest impact.

Catch you on the Start Line,
—Matty