Legacy Builders: Strategies for Building Successful Family Enterprises

In this episode, Cory Gagnon joins Gavin Brower and Gerry Meyer to discuss what really shapes a successful transition inside a family enterprise. Expectations around leadership, ownership, timing, and readiness can easily drift apart when they remain unspoken. One generation may be thinking about succession while another is still deciding whether they want a role at all. Gavin and Gerry explore ho...

In this episode, we’re joined by Devin DeCiantis, Managing Partner at Lansberg Gersick Advisors. Devin has spent years studying how family enterprises endure across generations, focusing on governance, risk, and resilience. Our conversation explores how culture and history shape the way families respond to uncertainty, why long periods of stability can create complacency, and what it means to buil...

In this episode, Cory Gagnon is joined by Judi Cunningham and Tom McCullough for a timely 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 r...

In this episode, we’re joined by Katherine Bright, Family Enterprise Consultant at Trella Advisory Group. For nearly two decades, Kathy has helped family businesses navigate the decisions, relationships, and responsibilities that shape continuity across generations. Her work spans consulting, education, and board service, giving her a grounded understanding of the challenges families, boards, and...

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 w...

In this episode, we’re joined by Grant Conroy, Portfolio Manager with Genus Capital Management, where he works with families as they think through wealth, purpose, and legacy. With nearly three decades in global financial markets, Grant brings both technical experience and a human perspective to his work. He helps families look beyond the numbers and consider how their wealth can support their pur...

In this episode of Legacy Builders Live, Cory Gagnon is joined by Cindy Radu and Leah Tolton to explore what it truly takes to build ownership structures that last. Together, they move beyond the technical aspects of trusts and shareholder agreements, highlighting how structure without shared understanding often falls short. They dive into the difference between preparing owners versus managers, w...

In this special panel episode of Legacy Builders, Cory Gagnon is joined by Barb Schimnowsky and James Grieve for a focused conversation on how family enterprises can prepare for next-generation leadership. Drawing from their work in executive search, governance, succession planning, strategy, and family enterprise advising, Barb and James examine what leadership readiness looks like beyond age, ti...

In this episode, we’re joined by Sarah Walker, founder and principal designer of Nuance Interior Design, where she creates deeply personalized, wellness-centred estates for families and family offices. With more than 20 years of experience and over 50 multimillion-dollar estates and compounds completed, Sarah brings a rare blend of sophisticated global taste, technical fluency, and systems thinkin...

In this episode, we’re joined by Dr. Shay Harris-Pierre, Senior Consultant with Continuity Family Business Consulting, where she works at the intersection of family relationships, wealth, and identity. A clinically trained consultant and therapist, Licensed Professional Counselor, and Certified Financial Therapist, Shay brings nearly fifteen years of experience helping individuals, couples, and fa...

In this episode, we’re joined by Aileen Miziolek, consultant with The Family Business Consulting Group, where she works with business-owning families to design strategies and processes that support both enterprise success and healthy relationships across generations. With more than 20 years of experience in complex financial and estate planning, along with designations in financial planning, famil...

In this episode, we’re joined by Wendy Sage-Hayward, Senior Consultant with The Family Business Consulting Group, where she advises family enterprises, business leaders, and boards on continuity, governance, and generational transition. She is also Academic Director at Family Enterprise Canada, leading the Family Enterprise Advisor program, and co-author of Own It!, bringing both practical and res...

In this episode, we’re joined by David York, director at York Howell. David practices law in the areas of estate planning, tax, business planning, and non-profit entities. He is a fellow of the American College of Trust and Estate Counsel and a dean with the Purposeful Planning Institute. Chambers and Partners has recognized him in Estate Planning, a distinction awarded to approximately the top 2%...

In this episode, we’re joined by Alexander Saunders, Practice Director at Dialogos. Alex is a generative facilitator working at the intersection of dialogue, leadership, and complex human systems. Through work across the entertainment, venture capital, and hospitality sectors, as well as his own fifth-generation family business and other family-owned enterprises ranging from single-site operations...

In this episode, we welcome Dr. Charles Eckhart, Founder and Managing Partner of Cathexis Group, a family engagement and governance consulting firm based in Santa Barbara, California. Charles advises enterprising families and couples of significant wealth through major transitions, helping them strengthen family governance and build collaborative decision-making practices that endure across genera...

In this episode, we’re joined by Jeff Savlov, Founder of Blum & Savlov, LLP. For over 25 years, Jeff has helped family businesses, high-net-worth families, and their advisors balance family dynamics with the management of shared assets across generations. Drawing from his experience in his own family’s business, Jeff brings a grounded, common-sense perspective on how families can reduce conflict b...

In this episode, we’re joined by Jennifer East, Founder of ONIDA Family Advisors. With nearly 20 years of experience guiding affluent and enterprising global families, Jennifer brings a cross-cultural lens to the inner dynamics of continuity, especially when individual identity and family legacy quietly collide. We explore why it’s so common for next-gen leaders to inherit expectations before they...

In this episode, we’re joined by Amy Stein, Chief Impact Officer at Generations Trusted Family Business Advisors. With over 20 years in her family’s fourth-generation business, Henry’s, and experience launching its mental health foundation, Amy brings a rare perspective on legacy, leadership, and impact. Our conversation focuses on what transition really feels like, how identity shifts, how clarit...

In this episode, we’re joined by Susan Latremoille, Co-Founder and Partner at Next Chapter Lifestyle Advisors. With more than 35 years of experience as a wealth advisor, including leadership roles on RBC’s Chairman’s Council and the board of Richardson Wealth, Susan now helps clients and advisors plan for the human side of life transitions. As a Certified Exit Planning Advisor and Retirement Coach...

In this episode, we’re joined by Russel Baskin, a consultant and certified executive coach with Trella Advisory Group. Drawing from her background in human development and two decades of experience with business families, Russel helps name what often goes unspoken in transition, how control, identity, and legacy quietly shape relationships and decision-making. From habitual patterns to intergenera...

In this episode, Dr. Julia Edelman, board-certified gynecologist, author, and nationally recognized menopause expert, joins us to open a conversation we’ve never had on Legacy Builders: the impact of women’s health, specifically menopause, on family enterprise. A Yale, Columbia, and Harvard-trained physician with over four decades of experience, Dr. Edelman brings both clinical authority and compa...

In this episode, we’re joined by Keita Demming, Partner at The Covenant Group, award-winning author of Strategy to Action, and trusted advisor in strategy, design, and innovation. We explore how strategy becomes a lived practice through intentional behaviour, personal development, and the quality of our conversations. Keita shares his approach to coaching leaders through conflict avoidance, curati...

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 c...

In this episode, we’re joined by Andrea Lekushoff, founder and CEO of CONTEXT Studios, where personal stories become powerful tools for connection, continuity, and leadership. We talk about the invisible value of lived experience, how one person’s reflections can clarify identity, honour legacy, and even shape culture across generations. What does it mean to “be seen” by the people who come after...

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 ca...