The CN Tower turns 50 today — it opened to the public on June 26, 1976 — and Matt can’t stop thinking about what makes a tower iconic: the way one structure becomes shorthand for an entire city, from Toronto to Seattle’s Space Needle to the Eiffel Tower in Paris. It’s his new metaphor for the operator-to-icon journey. Becoming an icon means raising a tower rooted deep in your base — your brand, your story, your personality — that throws a beacon far past it. The catch is that towers take a long time to go up, and the base has to be ruthlessly focused before the signal can travel.
Which leads to a candid reflection: Matt’s own tower is still under construction. He’s wrestling with a real tension in who he serves — the established, hypergrowth founders he’s built around versus the people in transition whose stories tug at his heart — and why focus, not breadth, is what finally gets a structure off the ground. Along the way: a warm recap of his first “DiNNr” (six people, two and a half hours, the real stories behind the polished exteriors), a quick lap through this day in history, and a Substack milestone coming into view. A reflective Friday send-off to close: who will you connect with this weekend, and what will you do to take care of yourself?
