Bruce Reilly: What Endures – Judgment and Relationships

Nidale Chehade: Taking A Chance On Yourself

Careers rarely follow a straight path. In this episode of Outside of the Classroom, I talk with Nidale Chehade about building a career after university, finding the confidence to pursue opportunities, and embracing the uncertainty that comes with growth. From changing academic programs to transitioning into product development, we explore how curiosity, initiative, supportive leaders, and continuous learning have shaped her journey—and why some of our most valuable experiences are the ones we least expect.

Derek Bartlett and Paul May: Building More Than a Business

In this episode, I sit down with Derek Bartlett and Paul May, the founders of Legacy Basketball Academy, to discuss the journey of building an organization from the ground up. We explore the realities of entrepreneurship, earning trust, building credibility, developing culture, and making growth decisions that align with long-term goals. We also discuss leadership, community impact, and the importance of creating an environment that develops people both on and off the court. This is a conversation about what it takes to build something meaningful—and what it takes to sustain it.

James Stauch: Perspective - Thinking Deeper in a World That Moves Faster

In this episode, I speak with James Stauch about systems thinking, complexity, and why many organizations struggle to solve the problems they face. Our conversation explores the tension between urgency and understanding — from AI and entrepreneurship to education, leadership, and public systems — and why modern organizations are increasingly rewarded for reacting quickly rather than thinking deeply. This episode examines why developing a deeper understanding of the systems around us may become one of the most important capabilities for leaders, organizations, and societies moving forward.

Garie Adamson: 100 Miles and Still Going - Building a Brand That Outlasts the Moment

What does it take to build something that lasts? In this episode, I sit down with Garie Adamson, founder of a brand rooted in Toronto’s early hip-hop culture that has remained relevant for over three decades. We talk about recognizing opportunity early, navigating rapid growth, and adapting without losing identity. Garie also shares the realities behind the brand—competition, setbacks, and the discipline required to keep evolving.

Deep Dive: Understanding Scar Tissue

Scar tissue is what experience leaves behind. It manifests in how you think, decide, and respond. In this Deep Dive episode, we explore scar tissue: * what it is, * where it adds value, * where it can work against you, and * how to work with it So that it informs your judgment without narrowing it.