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. Who You’re Becoming: How Strategy, Leadership, and Legacy Start Within

    3D AGO

    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 behaviour, 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. We talk about what strategy really looks like when it's practiced daily, why organizations often struggle to face hard truths, and how self-awareness, team dynamics, and sector alignment can either accelerate or stall transformation. Keita brings practical insight and honest reflection on what it takes to build something meaningful, starting with the conversations we choose to have. Whether you're growing a business, refining your leadership, or rethinking your goals, this episode offers a grounded framework for becoming the kind of leader your future needs. About Keita Demming Keita is an award-winning author, educator, and coach focused on transforming companies into idea-driven, people-centred environments. His book Strategy to Action offers a practical approach for turning bold ideas into tangible results, helping close the often-frustrating gap between strategy and execution. As a trusted advisor in design, strategy, and innovation, Keita also hosts the podcast Conversations with Keita Demming, where he explores insights from leaders across disciplines. He believes learning from others lightens our own journey. Among his proudest achievements is building the TEDxPortofSpain community, one of the most successful TEDx events globally. Resources discussed in this episode: Strategy to ActionErykah BaduThe Selfish Gene by Richard DawkinsCS LewisBrene BrownContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Keita Demming | The Covenant Group  Website: keitademming.comLinkedIn: Keita DemmingYouTube: @KeitaDemmingInstagram: kdemmingFacebook: keitademmingconversationsEmail: keita@covenantgroup.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.

    51 min
  2. Before It’s Written Down: Why Estate Planning Is About More Than the Plan

    OCT 17

    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? Jenna brings both experience and candour to a conversation that explores more than just documents and directives. She shares real stories that reveal how family dynamics, unclear expectations, and misaligned roles can create lasting consequences or be transformed through thoughtful planning and early dialogue. Whether you're choosing your executor or are the executor, this episode offers insight into what stewardship really looks like before, during, and after the will is read. About Jenna Carvalho Jenna Carvalho is the Founder and Principal of Guardian Estate Company, where she helps successful Canadian families navigate the complexity of estate planning, administration, and legacy stewardship. With over 15 years of experience, including a decade at BMO Private Wealth, Jenna has directly managed more than 100 estates and acted as trustee for dozens of trusts, foundations, and powers of attorney. She holds an MBA from Queen’s University, along with the Trust and Estate Practitioner (TEP) and Member of Trust Institute (MTI) designations, credentials that underscore both her technical expertise and commitment to excellence. Resources discussed in this episode: Estates Made SimpleContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Jenna Carvalho | Guardian Estate Company:  Website: guardianestate.caLinkedIn: Jenna CarvalhoEmail: jenna@guardianestate.caPhone: 403-990-3524 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
  3. The Stories That Hold Us: Why Capturing Memory Is a Strategic Act of Care

    OCT 3

    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, honour 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? Andrea shares how stories of struggle, resilience, and values often told too late can become guiding touchstones for successors, executive teams, and even entire organizations. Whether the audience is your grandchildren or your boardroom, this conversation invites a fresh look at legacy not just as something you leave, but something you live. About Andrea Lekushoff Andrea Lekushoff is the founder and CEO of CONTEXT Studios, the premier creator of high-end, episodic documentaries that immortalize the lives, entrepreneurial journeys, and multigenerational family legacies of distinguished individuals and families for generations to come. CONTEXT Studios is also proud to serve as an Alliance Partner of Family Enterprise Canada. With more than three decades of experience as a PR executive and founder of the award-winning agency Broad Reach, Andrea has been a trusted advisor to C-Suite leaders and global brands, designing bespoke strategies and amplifying their stories and influence on the world stage. Andrea’s credentials include an MBA from the Ivey Business School, a BA (Honours) from Western University, and two executive education programs at Harvard Business School through YPO. She is an affiliate partner of Women Get On Board Inc., where she elevates top board candidates through their ELEVATE program, and she serves on the board development committee for the Luminato Festival in Toronto. Resources discussed in this episode: Context StudiosHarvard Business School Family Enterprise CanadaContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: beaconfamilyoffice@assante.comContact Andrea Lekushoff | CONTEXT Studios:  Website: CONTEXTStudios.caLinkedIn: Andrea LekushoffEmail: alekushoff@brpr.caInstagram: Context_StudiosFacebook: CONTEXTStudiosCAPhone: 416-435-2569 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. Developmental Crises: Helping Leaders and Families Grow Through Defining Moments

    SEP 19

    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
  5. When Legacy Grows Up: Shifting from Founders to Families in Enterprising Wealth

    SEP 5

    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
  6. Past, Present, and Possibility: Reimagining Legacy Through Story

    AUG 22

    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
  7. The Quiet Fix: Why Better Family Communication Starts Before the Meeting Begins

    AUG 8

    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
  8. The Fear of Ugly: Reframing Conflict in Family Enterprise Communication

    JUL 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. 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
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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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