Legacy Builders: Strategies for Building Successful Family Enterprises

In this episode, Cory Gagnon is joined by Judi Cunningham and Tom McCullough for a conversation on how families can make better decisions together. From estate plans to ownership transitions, it’s rarely the decisions themselves that hold families back; it’s the buildup around them. Roles are unclear. Assumptions go unspoken. And sometimes, one voice dominates when collaboration is what’s really needed. Judi and Tom share what gets in the way, and more importantly, how families can start moving forward with clarity, confidence, and trust.

In this episode, we’re joined by Kirby Rosplock, PhD, Chief Executive Officer and Founder of Tamarind Learning. With more than 25 years of experience across family wealth, family business, and family office education, Kirby brings the perspective of an advisor, researcher, author, educator, and family member. Our conversation explores the often unspoken work of succession, including what happens when a founder has long been the final yes-or-no, how families prepare for decisions to be shared differently, and why the next generation needs a genuine invitation before responsibility begins to change hands.

In this episode, we’re joined by Jenna Carvalho, Founder and Principal of Guardian Estate Company, whose work sits at the intersection of estate planning, family relationships, and meaningful legacy. With more than 100 estates and dozens of trusts under her direct care, Jenna has witnessed the full spectrum of outcomes, both smooth and strained, when families face the inevitable transitions that come with wealth, loss, and leadership. We talk about what it’s really like to act as an executor for the first time, how communication (or the absence of it) can change everything, and why estate planning is less about predicting the future and more about preparing people for it. What happens when intentions go unspoken? When roles aren't clearly understood? And when decisions once thought simple suddenly carry emotional weight?

In this episode, we’re joined by Dr. Paul Edelman, a Harvard-trained psychologist and longtime advisor to leaders and families navigating complex transitions. What if uncertainty isn’t something to fix, but something to learn from? What if discomfort could actually move us forward? Together, we explore these questions and more looking at how moments of disorientation can deepen clarity, stretch capacity, and strengthen connection across generations.

In this episode, Julia Chung, Co-Founder and CEO of Spring Planning, joins us to explore the kinds of questions that can reshape a family’s future. As Board Director and FEA Community Council Chair at Family Enterprise Canada, and Chair of the Financial Planning Association of Canada’s Board, Julia brings a depth of experience that turns difficult conversations into turning points. Together, we venture into the spaces where legacy is defined, identity is examined, and agency is reclaimed.