In this episode, we sit down with David Lee, Chief Creative Officer at Squarespace, to trace his journey from a restless teenager in suburban Montreal to leading one of the most design-forward companies in the world.

David shares how skate culture and DIY design first opened his eyes to creativity, what he learned at the Rhode Island School of Design (including the life-changing lesson of drawing with his left hand), and how he carved his path through some of the world’s top creative agencies like Sid Lee, AKQA, and Wieden+Kennedy, before making the bold leap into tech.

He also reflects on building Squarespace’s in-house creative team, embracing risk, and the role of self-awareness as the most valuable career investment. From navigating imposter syndrome to leading creative teams through technological disruption, David’s story is a masterclass in staying curious, adaptive, and human in a rapidly changing world.