Last week, we hosted our first-ever CTO School of Fish Dinner, bringing together some of the brightest tech minds from across the GTA, Waterloo, and Montreal. The goal? To create a space where tech leaders—whether from early-stage startups, late-stage scale-ups, or those who’ve exited and moved on—could come together for candid, insightful, and sometimes counterintuitive discussions.

Being a CTO today isn’t just about writing code or scaling infrastructure—it’s about making game-changing decisions in a world where technology is evolving faster than ever. It’s about navigating the paradox of innovation vs. execution, managing technical debt without killing momentum, and defining strategies that don’t just follow industry trends but shape them. These are the conversations that rarely happen in public. But at this dinner, they did.

Throughout the night, we discussed the tough questions that tech leaders are constantly grappling with. There were no simple solutions—just diverse perspectives, practical insights, and honest reflections from those who have navigated these challenges firsthand. The discussions were engaging, and the key takeaways were highly valuable.

As a former CTO myself, I know how rare it is to have a space like this—where you can drop the guard, talk openly about the real challenges, and gain perspectives that can actually shift the way you think. Multiple attendees said they wished a group like this existed earlier in their careers. We couldn’t agree more. 

By the end of our dinner, attendees had formulated several thought-provoking questions for the next dinner, and I can’t wait to hear what they have to say. 

We believe in the power of bringing builders together. Last week proved that when the right minds are in the same room, ideas spark, lessons are shared, and meaningful connections are formed.

If you weren’t at the table this time, make sure you’re on the radar next time.

Until then, the conversations continue!