
Legacy Builders: Strategies for Building Successful Family Enterprises
by Cory Gagnon
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From 13 epsHost
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Recent episodes
The Next Chair: Governing Tomorrow, Next Generation Leadership in Family Enterprises
Jun 19, 2026
Unknown duration
Designing for the Life Ahead: How Homes Can Support Every Stage of Family Life
Jun 5, 2026
48m 05s
Where Wealth Meets Identity: Finding Voice Inside the Family Legacy
May 22, 2026
52m 45s
Reflection Over Reaction: How Families Improve Decision-Making in Family Enterprises
May 8, 2026
48m 09s
Leading Before the Role: How Family Enterprises Shape Future Leaders
Apr 24, 2026
53m 19s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/19/26 | ![]() The Next Chair: Governing Tomorrow, Next Generation Leadership in Family Enterprises | 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, title, or family position. They discuss how governance can clarify roles and decision-making, why succession conversations are often delayed, and what families can do before the transition becomes urgent. | — | ||||||
| 6/5/26 | Designing for the Life Ahead: How Homes Can Support Every Stage of Family Life✨ | home designfamily life+3 | Sarah Walker | Nuance Interior Design | — | home designwellness-centered estates+3 | — | 48m 05s | |
| 5/22/26 | Where Wealth Meets Identity: Finding Voice Inside the Family Legacy✨ | family relationshipswealth+4 | Dr. Shay Harris-Pierre | Continuity Family Business Consulting | — | family legacyfinancial therapy+4 | — | 52m 45s | |
| 5/8/26 | ![]() Reflection Over Reaction: How Families Improve Decision-Making in Family Enterprises✨ | family enterprisesleadership+3 | Aileen Miziolek | The Family Business Consulting GroupInspired Wealth: Financial Leadership for the 21st Century | — | family businessleadership development+3 | — | 48m 09s | |
| 4/24/26 | Leading Before the Role: How Family Enterprises Shape Future Leaders✨ | family enterprisesleadership+3 | Wendy Sage-Hayward | The Family Business Consulting GroupFamily Enterprise Canada+1 | — | family businessleadership development+3 | — | 53m 19s | |
| 4/10/26 | Rethinking Ownership: The Hidden Forces Shaping Family Wealth✨ | family wealthlegacy planning+4 | David York | York HowellAmerican College of Trust and Estate Counsel+4 | — | family wealthlegacy+4 | — | 46m 49s | |
| 3/20/26 | When the Role Finds You: The Tension Between Belonging and Becoming✨ | leadershipfamily enterprise+4 | Alexander Saunders | Dialogosfifth-generation family business+1 | — | leadershipfamily business+5 | — | 47m 31s | |
| 3/6/26 | Steady Through Uncertainty: Mentors, Mistakes, and Next-Gen Growth✨ | family governancewealth management+4 | Dr. Charles Eckhart | Cathexis Group | Santa Barbara, California | family engagementgovernance+5 | — | 58m 27s | |
| 2/20/26 | Roots of Resilience: Raising Grounded Children in Families of Wealth✨ | family dynamicswealth management+3 | Jeff Savlov | Blum & Savlov, LLP | — | family businesseshigh-net-worth families+3 | — | 44m 40s | |
| 2/6/26 | Becoming Who You Are: Reclaiming Choice in Enterprising Families✨ | family legacynext-gen leaders+4 | Jennifer East | ONIDA Family Advisors | — | family enterprisesleadership+5 | — | 45m 44s | |
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| 1/23/26 | Still Yours to Shape: Reclaiming Identity in Times of Transition✨ | identitytransition+4 | Amy Stein | Generations Trusted Family Business AdvisorsHenry’s | — | identitytransition+5 | — | 42m 55s | |
| 1/9/26 | Designing the Next Chapter: Retirement Planning for Purpose, Identity, and What Comes Next✨ | retirement planninglife transitions+4 | Susan Latremoille | Next Chapter Lifestyle AdvisorsRBC+1 | — | retirementwealth advisor+5 | — | 52m 55s | |
| 11/28/25 | Finding Yourself After Leadership: The Missing Chapter in Succession✨ | leadership transitionsuccession planning+4 | Russel Baskin | Trella Advisory Group | — | leadershipsuccession+5 | — | 47m 00s | |
| 11/14/25 | Silence Is Not Succession: Why Women’s Health Belongs in Family Conversations✨ | women's healthmenopause+3 | Dr. Julia Edelman | YaleColumbia+1 | — | women's healthmenopause+3 | — | 50m 53s | |
| 10/31/25 | Who You’re Becoming: How Strategy, Leadership, and Legacy Start Within | 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 behavior, personal development, and the quality of our conversations. Keita shares his approach to coaching leaders through conflict avoidance, curating effective inner circles, and aligning day-to-day actions with long-term vision. He introduces a powerful shift in thinking from chasing outcomes to asking better questions and what it means to lead with clarity and courage. | — | ||||||
| 10/17/25 | Before It’s Written Down: Why Estate Planning Is About More Than the Plan | 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? | — | ||||||
| 10/3/25 | The Stories That Hold Us: Why Capturing Memory Is a Strategic Act of Care | 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, honor legacy, and even shape culture across generations. What does it mean to “be seen” by the people who come after you? How do stories become more than memories, and why is capturing them now, not later, a strategic decision? | — | ||||||
| 9/19/25 | Developmental Crises: Helping Leaders and Families Grow Through Defining Moments | 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. | — | ||||||
| 9/5/25 | When Legacy Grows Up: Shifting from Founders to Families in Enterprising Wealth | In this episode, Dr. Dennis T. Jaffe, Senior Research Fellow at BanyanGlobal Family Business Advisors, joins us to explore how family enterprises can evolve with intention across generations. A globally recognised adviser, educator, and author of Wealth 3.0 and Borrowed from Your Grandchildren, Dennis brings decades of insight into how families build shared purpose, navigate complexity, and sustain legacies that matter. | — | ||||||
| 8/22/25 | Past, Present, and Possibility: Reimagining Legacy Through Story | 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. | — | ||||||
| 8/8/25 | The Quiet Fix: Why Better Family Communication Starts Before the Meeting Begins | In this episode, Shauna Trainor, Principal at A&O Partners, invites us into the often overlooked spaces where clarity, courage, and connection shape the future of enterprising families. Drawing from her background in business, psychology, and systems thinking, Shauna helps us reframe how family conversations become the foundation for shared decision-making across generations. | — | ||||||
| 7/25/25 | The Fear of Ugly: Reframing Conflict in Family Enterprise Communication | In this episode, Jane Beddall, founder of Dovetail Resolutions, helps us reframe how conflict shows up in family enterprises. Drawing on her experience as a mediator, consultant, and conflict coach, Jane shares why not all conflict is the same—and how the fear of escalation often prevents families from addressing tension early. We explore the distinction between healthy disagreement and deeper dysfunction, and why timing, environment, and tone matter more than we often realize. | — | ||||||
| 7/11/25 | ![]() The Courage to Continue: Why Emotional Readiness Shapes Enterprise Legacy | In this episode of Legacy Builders, we welcome Krista Rabidoux, Partner at Andersen in Canada, for a thoughtful conversation on leadership transition, generational readiness, and the emotional complexity of family enterprise. With over two decades of experience in U.S.-Canada cross-border tax planning and deep involvement in the family enterprise space, Krista shares how clarity, adaptability, and inclusive governance can help families move forward, especially when navigating uncertainty or change. | — | ||||||
| 6/27/25 | Breaking the Log Jam: Clearing Complexity to Build Sustainable Family Wealth | In this episode, Don Steele, CEO and Founder of Sterling Family Capital, shares his perspective on guiding family enterprises through complex transitions with clarity and collaboration. With deep roots in finance and advisory, Don helps families navigate the emotional and strategic layers of ownership, succession, and legacy-building across generations. | — | ||||||
| 6/13/25 | ![]() Breaking the Pattern: How Self-Awareness and Choice Transform Family Wealth Dynamics | In this episode, we welcome Kristen Heaney, Founder & Coach of In Three Generations, LLC, a trusted coach to financially successful families, and an authentic voice in the wealth management space. Known for her unique perspective as an "unprepared inheritor in recovery," Kristen brings a deep understanding of family wealth challenges, bridging the gap between gratitude and burden while helping families navigate the complexities of wealth preservation and transition. Together, we explore what it takes to honour legacy while fostering individual expression, touching on unconscious behaviors, stewardship responsibilities, and what it means to redefine success across generations in wealth, family, and life. | — | ||||||
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