Entrepreneurship, Innovation, and Montreal Vibes with Shopify’s Harley Finkelstein

This week on If You Know, You Know, I’m joined by someone who needs no introduction, Harley Finkelstein, President of Shopify, longtime entrepreneur, and genuinely one of the most generous mentors in the business world.

Harley doesn’t just talk about success he teaches it. In this episode, we dive into what it really takes to build and scale an iconic global brand, how to stay creative in a fast-changing world, and why mentorship, community, and taking smart risks matter more than ever.

From early career lessons to leadership insights, Montreal influence to real talk about entrepreneurship, this conversation is packed with takeaways for founders, creatives, and anyone chasing something bigger.

Whether you’re building a company, a personal brand, or just looking for perspective from someone who’s been there and actively lifts others up. This episode is one you’ll want to save, share, and revisit.

Big ideas, honest advice, and a little Montreal flavour. Let's freaking gooooo