Legacy Builders: Strategies for Building Successful Family Enterprises

Cory Gagnon
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Cory Gagnon doesn’t just love supporting multi-generational families every day. He loves digging into topics and sharing information that matters to family enterprises! In Legacy Builders: Strategies for Building Successful Family Enterprises, Cory, Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd, dives deep to share ways for business owners, family stewards, and the rising generation in family enterprises to take control of their wealth and build a lasting legacy. Through interviews with industry experts, each episode provides understandable and actionable strategies and insights on complete wealth management. From navigating family dynamics to developing a successful wealth transition plan and everything in between, this is the podcast to bring your legacy into the future. Subscribe today!

  1. Developmental Crises: Helping Leaders and Families Grow Through Defining Moments

    3 DAYS AGO

    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. Paul brings a grounded perspective to the kinds of moments many of us try to avoid when roles are shifting, plans feel uncertain, or emotions run high. Instead of rushing to resolution, he invites us to stay curious and present. If you’re wondering how to lead or support others through change without losing yourself along the way, this conversation offers a thoughtful place to begin. Resources discussed in this episode: Dabrowski’s Theory of Positive Disintegration in PsychologySteve jobsPurposeful Planning InstituteContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Paul Edelman | Edelman & Associates:  Website: edelmancoaching.comLinkedIn: Paul EdelmanEmail: paul@edelmancoaching.com We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    44 min
  2. When Legacy Grows Up: Shifting from Founders to Families in Enterprising Wealth

    5 SEPT

    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. Together, we look at the role of values in decision-making, the shift from inheritance to stewardship, and the everyday work of preparing the next generation. With a calm and grounded perspective, Dennis invites us to rethink not just how families lead, but how they learn, change, and grow together. If you’re asking what helps families stay connected while moving forward, this conversation offers a thoughtful place to begin. About Dennis T. Jaffe Dennis T. Jaffe, Ph.D., is Senior Research Fellow at BanyanGlobal Family Business Advisors and a San Francisco-based adviser to multigenerational families navigating the complexities of business, governance, wealth, and philanthropy. With a background in sociology and organisational systems, he helps families align values with long-term decision-making and supports the evolution of family enterprises across generations and geographies. His advisory and teaching work has taken him to Asia, Europe, the Middle East, and Latin America, reflecting a lifelong commitment to practical insight and cultural fluency. A leading voice in the field, Dennis is the author of several influential books, including Wealth 3.0: The Future of Family Wealth Advising, Borrowed from Your Grandchildren, and Cross Cultures. He has received multiple honours from the Family Firm Institute and Family Wealth Report for his contributions to family enterprise advising. A Yale-trained sociologist and professor emeritus at Saybrook University, Dennis blends academic depth with practical experience to guide families in building legacies rooted in purpose, resilience, and shared understanding. Resources discussed in this episode: Wealth 3.0: The Future of Family Wealth AdvisingBorrowed from Your Grandchildren: The Evolution of 100-Year Family EnterprisesFinding Her Voice and Leaving a LegacyCross Cultures: How Global Families Negotiate Change Across GenerationsStewardship in your Family EnterpriseWorking with the Ones You LoveContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Dennis T. Jaffe | BanyanGlobal Family Business Advisors:  Website: dennisjaffe.com | banyan.globalLinkedIn: Dennis JaffeEmail: djaffe@dennisjaffe.comPhone:  415 665 8699 We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations.

    47 min
  3. Past, Present, and Possibility: Reimagining Legacy Through Story

    22 AUG

    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. You’ll hear how imagining the future from the very end can shift today’s choices, why the stories we tell become the roots of legacy, and how families can make room for both individual expression and shared responsibility. Along the way, Julia challenges us to rethink status, belonging, and what it means to contribute something uniquely our own. If you’ve ever wondered how to align your next decision with values that will stand the test of time, this conversation is one you won’t want to miss. About Julia Chung Julia is CEO of Spring Planning, Board Director at Family Enterprise Canada, and Board Chair of the Financial Planning Association of Canada. With expertise in personal, business, and cross-border finance, governance, family enterprise, and conflict resolution, she empowers clients through values-based decision-making frameworks. A prolific author, she has co-authored Women & Money, The Art of Delegation, and The Entrepreneur’s Survival Guide, served as Business Editor for Gazette and PowHerHouse magazines, and was Technical Editor for the 2024 release of Funding a New Business for Dummies. Julia has helped shape the future of financial advice in Canada, founding and leading multiple organizations. Known for her entrepreneurial spirit and her ability to “Manifest the Improbable,” she draws from a lifetime in a family that is both entrepreneurial and academic, and thrives on challenges—especially those beginning with, “You can’t do that.” Resources discussed in this episode: Family Enterprise CanadaDaniel KahnemanContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Julia Chung | Spring Planning:  Website: springplans.caInstagram: @springplansTwitter: @springplansFacebook: Spring PlansLinkedIn: Julia chungEmail: info@springplans.ca We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    47 min
  4. The Quiet Fix: Why Better Family Communication Starts Before the Meeting Begins

    8 AUG

    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. Shauna shares why many answers already exist within families if we're willing to slow down, ask the right questions, and listen beyond the surface. We explore how unspoken complaints often sound like blame or shame, and how reframing them into requests opens doors to empathy, understanding, and real change. Whether you’re wrestling with readiness, managing expectations, or inviting the next generation to the table, this episode offers grounding questions and practical ways to begin at your own pace, and with your values leading the way. About Shauna Trainor Shauna Trainor works with enterprising families across North America to navigate the complexities of ownership, wealth, and family dynamics. Through a collaborative planning process, she helps families identify, clarify, and articulate their multigenerational vision and strategy. Her work supports the development of effective governance structures, strengthens communication, and fosters shared decision-making. Drawing on her background in business and psychology as well as her broad educational and travel experiences Shauna brings a well-rounded perspective that helps families and individual members move toward their desired outcomes with clarity and confidence. Resources discussed in this episode: Life Is in the Transitions: Mastering Change at Any AgeBrené BrownThe Wealth Money Can't BuyAll in All: Mulliez Family TriumphsContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Shauna Trainor | A&O Partners LLP:  Website: ao.partnersLinkedIn: Shauna TrainorEmail: shaunajtrainor@gmail.com We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    45 min
  5. The Fear of Ugly: Reframing Conflict in Family Enterprise Communication

    25 JUL

    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. Jane offers a fresh lens on how families can turn conflict into connection. From the “ugly kind” of conflict to the kind that builds trust, she shares insights that might shift how you approach tough conversations. Whether you're navigating legacy, leadership, or long-held patterns, this conversation opens up practical, surprising ways to move forward—without losing what matters most. About Jane Beddall Jane Beddall, M.A., J.D., is the founder and principal of Dovetail Resolutions, LLC. She is a seasoned mediator, consultant, and certified CINERGY® Conflict Management Coach. Jane works with legacy families, family enterprises, and family offices to help individuals and families handle communication and conflict better. Her expertise in using conflict coaching with transformative mediation is especially effective in these circumstances. In January 2019, Jane launched the weekly podcast Crafting Solutions to Conflict, providing a practical and positive perspective on conflict. She graduated from Trinity College (Hartford, CT) with a B.A. in Economics. She earned her law degree, cum laude, and her M.A. in Public Policy Analysis, with a concentration in Conflict Resolution, from the University of Pennsylvania. Jane is a Conflict Dynamics Profile® Certified Practitioner and holds Family Firm Institute Certificates in Family Business Advising and Family Wealth Advising. She lives in Naples, Florida. Resources discussed in this episode: Crafting Solutions to ConflictDovetail ResolutionsCinnie NobleContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Jane Beddall | Dovetail Resolutions, LLC Website: dovetailresolutions.comPodcast: Crafting Solutions to ConflictLinkedIn: Jane BeddallEmail: jb@dovetailresolutions.comPhone: (203) 887-1160 We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

    46 min
  6. The Courage to Continue: Why Emotional Readiness Shapes Enterprise Legacy

    11 JUL

    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. Together, Cory and Krista explore what it takes to prepare rising generation leaders not just in theory, but in real-world ownership. They discuss how families can foster resilience through shared learning, how emotional awareness influences decision-making, and why slowing down is often the smartest move in times of complexity. Tune in to hear how intentional structure, open dialogue, and a willingness to evolve can help families build a legacy with both strength and care. About Krista Rabidoux With over 24 years of experience in U.S.-Canada cross-border tax planning, Krista Rabidoux offers more than technical expertise, she brings a holistic perspective to family enterprise strategy. As both a tax professional and certified executive coach, her work focuses on the intersection of financial clarity and leadership development, helping families navigate transitions with confidence. Her approach goes beyond compliance. Krista partners with clients to support rising generation leadership, strengthen team dynamics, and align business goals with family values. Whether guiding succession planning or evolving enterprise governance, she brings both the precision of a tax advisor and the insight of a coach. Resources discussed in this episode: Buy Back Your Time: Get Unstuck, Reclaim Your Freedom, and Build Your EmpireRich Dad Poor DadStrength Deployment InventoryFamily Enterprise CanadaContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Krista Rabidoux | Andersen in Canada:  Website: ca.andersen.comLinkedIn: Krista Rabidoux  We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations.

    46 min
  7. Breaking the Log Jam: Clearing Complexity to Build Sustainable Family Wealth

    27 JUN

    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. Throughout the conversation, Don discusses how to recognize intuitive signals, untangle personal and business challenges, and build capacity in the rising generation. He highlights the importance of collaborative advisory teams, intentional mentorship, and developing an ownership mindset. Tune in to hear Don’s practical insights on strengthening family capital, aligning purpose with action, and creating legacies that last. About Don Steele A trusted advisor, financial executive, and investor passionate about helping entrepreneurs unlock the potential in their families and businesses. A valued partner and skilled collaborator, providing support and accountability to enterprising families and their advisors to preserve and nurture each family’s unique mix of financial and non-financial capital. Resources discussed in this episode: Range: Why Generalists Triumph in a Specialized WorldPioneering Portfolio ManagementPrivate Capital by Joe ReillyPurposeful Planning PodcastBuilt to Sell PodcastContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Don Steele | Sterling Family Capital:  Website: sterlingfamilycapital.comLinkedIn: Don SteeleEmail: don@sterlingfamilycapital.comPhone: (416) 302-2146 We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations.

    48 min
  8. Breaking the Pattern: How Self-Awareness and Choice Transform Family Wealth Dynamics

    13 JUN

    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. Throughout our conversation, Kristen challenges the belief that everyone must follow the same path to success within wealthy families. She shares why lasting fulfillment requires breaking free from unwritten rules and self-imposed pressures, emphasizing the courage to move beyond patterns of expectation that keep families stuck in cycles of obligation rather than authentic connection. Tune in to discover how intentional family governance, role clarity, and balanced frameworks can unlock your family's potential to honor collective purpose while preserving personal autonomy across generations. About Kristen Heaney  Kristen Heaney, Founder & Coach of In Three Generations, LLC, is a Coach and Consultant to financially successful families and individuals who guides clients through the complex landscape of wealth and its associated challenges. Having lost her business-owning father to cancer at 21, she brings profound understanding to helping clients thrive amidst their success while managing the unique burdens that arise. As both an "unprepared inheritor in recovery" and Consultant and Instructor to professional advisors serving wealthy families, Kristen specializes in authentic connection and understanding unique family needs. Her proven approach helps clients implement effective strategies for managing wealth challenges while maintaining deep relationships across generations. Author of "In Three Generations: A Story about Family, Wealth, and Beating the Odds" and the children's book "The Super Special, Altogether Ordinary Day," Kristen creates inspirational content for those navigating unique struggles and intense celebrations. Her passion centers on helping successful individuals discover gratitude and purpose in their awesome work and relationships. Resources discussed in this episode: www.in3generations.comThe Quest for Legitimacy by Jamie WeinerContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Kristen Heaney | In Three Generations LLC:  Website: in3generations.comLinkedIn: Kristen HeaneyInstagram: @in3generationsEmail: coach@in3generations.com We're bringing together leading experts to tackle some of the most pressing challenges facing family businesses today—from succession planning and governance structures to preparing the next generation for leadership roles. You'll walk away with actionable strategies and fresh perspectives on building resilient family enterprises. Haven't caught one of our webcasts yet? No problem. All previous sessions are archived and ready to stream whenever you're ready to dive in. Simply head over to legacybuilderswebcast.com to register for our upcoming session or explore our growing library of past conversations.

    50 min
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Cory Gagnon doesn’t just love supporting multi-generational families every day. He loves digging into topics and sharing information that matters to family enterprises! In Legacy Builders: Strategies for Building Successful Family Enterprises, Cory, Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd, dives deep to share ways for business owners, family stewards, and the rising generation in family enterprises to take control of their wealth and build a lasting legacy. Through interviews with industry experts, each episode provides understandable and actionable strategies and insights on complete wealth management. From navigating family dynamics to developing a successful wealth transition plan and everything in between, this is the podcast to bring your legacy into the future. Subscribe today!

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