Legacy Builders: Strategies for Building Successful Family Enterprises

Cory Gagnon
  • 0.0 (0)
  • Entrepreneurship
  • Updated Biweekly

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. Jul 31

    Inherited Vision, Unwritten Future: How the Next Generation Shapes What Comes Next

    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. Kirby brings forward the human side of succession, reminding us that readiness is shaped not only by experience, but by trust, opportunity, and the space to grow beyond a founder’s shadow. Her perspective leaves us with a deeper understanding of why future leaders need more than a title before they are ready to carry responsibility. About Kirby Rosplock Kirby Rosplock, PhD, is the founder of Tamarind Partners, Inc. and Chief Executive Officer and co-founder of Tamarind Learning, an online education platform for families, beneficiaries, and their advisors. With more than 25 years of experience across finance, family wealth, family business, and family offices, Kirby is recognized as an advisor, educator, researcher, author, and speaker. Her perspective is also personal: born into a complex enterprising family, she understands firsthand the responsibilities of being a beneficial owner, inheritor, fiduciary, board member, and operator. Kirby is the author of *The Complete Family Office Handbook* and *The Complete Direct Investing Handbook*, as well as numerous articles and research studies. Her work has received recognition from Family Wealth Report, the Family Wealth Alliance, and the Family Firm Institute. She holds degrees from Middlebury College, Marquette University, and Saybrook University, and continues to contribute to family office and family enterprise education through several faculty, board, and advisory roles. Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd.  Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn: Beacon Family Office Email: beaconfamilyoffice@assante.com Contact Kirby Rosplock | Tamarind Learning Website: TamarindLearning.com | TamarindPartners.com LinkedIn: Kirby Rosplock Email: Kirby@TamarindPartners.com Phone: 561-427-1330 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.

    Inherited Vision, Unwritten Future: How the Next Generation Shapes What Comes Next

  2. Jul 17

    Return on Meaning: Rethinking Wealth Beyond Financial Capital

    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 purpose, their relationships, and the legacy they hope to build. Our conversation explores what it means to think about wealth not only as capital to manage, but as a resource that can shape how families live, connect, and make decisions over time. We talk about work ethic, motivation, and the moments that cause people to pause and reconsider what money is really meant to do. Along the way, Grant helps us consider family, lived experience, intuition, and the different forms of capital that shape how people define a meaningful legacy. About Grant Conroy Grant Conroy is a husband and father of three young children, and a Portfolio Manager with Genus Capital Management, serving families and clients across multiple generations. His belief that wealth is more than just a number on a statement shapes both his approach to wealth management and the way he works with clients.  With nearly three decades of experience in global financial markets, Grant has dedicated his career to helping families navigate the complexities of wealth with clarity, purpose, and perspective. His experience spans from working in Global Equity Markets at Goldman Sachs in London to advising clients across Canada. He is based in Vancouver, British Columbia, the city he proudly calls home. Resources discussed in this episode: The Cycle of the Gift - Jay Hughes Family Enterprise Canada Symposium Family Enterprise Canada Purposeful Planning Institute Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd.  Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn: Beacon Family Office Email: beaconfamilyoffice@assante.com Contact Grant Conroy | Genus Capital Management:  LinkedIn: Grant Conroy Email: gconroy@genuscap.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.

    Return on Meaning: Rethinking Wealth Beyond Financial Capital

  3. Jul 3

    The Architecture of Ownership: How Families Build Structures That Last

    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, why clarity around what’s owned (and how) matters, and how evolving governance builds resilience across generations. Throughout the conversation, a common thread emerges: enduring ownership isn't achieved through checklists or one-time planning. It's cultivated through intentional education, open dialogue, and collaborative advisor support. Whether you're navigating a leadership transition, aligning multigenerational interests, or rethinking how your family makes decisions, this episode offers timely insight into how families can move forward together, and on purpose. About Cindy Radu Cindy Radu is a family wealth transition advisor with over 30 years of global experience guiding families through complex succession, governance, and education strategies. Her multidisciplinary expertise in law, accounting, trusts, and governance allows her to support families in building effective ownership frameworks, strengthening intergenerational communication, and preparing rising generations for confident stewardship. Cindy works collaboratively with advisors to translate complex structures into clear, actionable steps tailored to each family’s unique needs. A champion of financial literacy and cross-generational education, Cindy serves as Chief Learning Officer (Canada) for Tamarind Learning and is actively involved in the global STEP community. Her work is grounded in clarity, empathy, and trust, shaped by her passion for mental health advocacy and her lived experience navigating the challenges of the Sandwich Generation. With every engagement, she helps families align values and vision, turning transition into opportunity. Contact Cindy Radu | Cindy Radu Advisory Ltd.:  Website: cindyradu.com LinkedIn: Cindy Radu Twitter: @radu_cindy Email: connect@cindyradu.com Phone: (403) 465-1926 About Leah Tolton Leah has practiced corporate law for 30 years, with extensive experience advising family-owned businesses, lending clients, and real estate clients on a broad range of matters including business agreements, tax planning, equipment leasing, mergers and acquisitions, real estate joint ventures, business structuring, and reorganizations. Her practice emphasizes serving ultra-high-net-worth families and their companies across critical areas such as corporate governance, succession planning, reorganizations, strategic planning, risk management, and navigating mergers, acquisitions, and sales transactions. Additionally, Leah negotiates and drafts commercial contracts, advises on private financing and syndicated lending arrangements, earned the Family Enterprise Advisor designation in 2023, and sits on the Board of Advisors of the Alberta Business Family Institute. This wide-ranging expertise and dedication to serving family enterprises equips Leah to provide tailored legal advice and counsel to family businesses seeking to establish continuity across generations. Contact Leah Tolton | Bennett Jones:  Website: bennettjones.com/ToltonLeah LinkedIn: Leah Tolton Email: toltonl@bennettjones.com Phone: (780) 917-4272  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.

    The Architecture of Ownership: How Families Build Structures That Last

  4. Jun 19

    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. The conversation also looks at the balance between promoting from within and bringing in external leadership, the value of objective assessments, and the role mentorship, advisory boards, and structured development can play in preparing future leaders. Cory, Barb, and James also consider the importance of supporting founders as they step into new roles and adapt to a changing place within the enterprise. About Barb Schimnowsky Barb Schimnowsky is a partner at Watson and the leader of the firm’s board director and executive search practice. With more than 25 years of experience in executive search and human resources, she brings deep expertise in leadership selection, governance, and succession planning. Barb holds both the Certified Management Consultant and Family Enterprise Advisor designations, and is known for her ability to understand client needs and align them with exceptional leadership talent. She has led hundreds of successful placements across sectors and has twice been recognized as one of the Top 100 Most Influential People in Abbotsford. Contact Barb Schimnowsky | Watson Board Advisors Website: https://www.watsoninc.ca/ | westviewsearch.ca LinkedIn: linkedin.com/in/barbschimnowsky Email: barb@watsoninc.ca Phone: 604 859 8002 About James Grieve James Grieve is founder and principal at Catalyst Strategies Consulting and co-creator of Succession Ready, a practical approach to succession planning for founder-led businesses. He holds the Certified Management Consultant, Family Enterprise Advisor, and Certified Exit Planning Advisor designations. James works with organizations to uncover blind spots, reduce risk, and build long-term value, with a particular focus on family enterprises and Indigenous-owned businesses. His approach blends strategy, systems thinking, and customer service to help families and businesses navigate transition with greater clarity and purpose. Contact James Grieve | Catalyst Strategies Consulting Website: catalyst-strategies.com | valuedriver.ca LinkedIn: linkedin.com/in/jamesnsgrieve Email: james@catalyst-strategies.com Phone: 17782146010 Resources discussed in this episode: Succession Ready 360-degree feedback Contact Cory Gagnon | Beacon Family Office at CI Assante Financial Management Ltd.:  Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn Page: Beacon Family Office Email: beaconfamilyoffice@assante.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.

    The Next Chair: Governing Tomorrow, Next Generation Leadership in Family Enterprises

  5. Jun 5

    Designing for the Life Ahead: How Homes Can Support Every Stage of Family Life

    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 thinking to her work. Her approach treats the home as a long-term operating system for health, relationships, recovery, focus, and multigenerational well-being. Our conversation explores what it means for a home to feel like a sanctuary while still supporting the full rhythm of everyday life.  We talk about how the spaces families live in can influence connection, rest, privacy, hosting, movement, and the way people feel when they walk through the door. Sarah reminds us that when a home is designed with care, it becomes a place that helps a family exhale, feel supported, and return to what matters most. About Sarah Walker Today, we’re joined by Sarah Walker, Founder and Principal Designer of Nuance Interior Design. Sarah creates deeply personalized, wellness-centred estates for families and family offices, homes designed not just to impress, but to restore, connect, and support real life. With more than 20 years of experience and over 50 multimillion-dollar estates and compounds completed, Sarah brings a rare blend of global design, sophisticated taste, technical fluency, and systems thinking. Her work treats the home as a long-term operating system for health, relationships, and multigenerational well-being. Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd.  Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn: Beacon Family Office Email: beaconfamilyoffice@assante.com Contact Sarah Walker | Nuance Interior Design:  Website: nuanceinteriors.com Instagram: @nuanceinteriors YouTube: @nuanceinteriors LinkedIn: Sarah Walker Email: sarah@nuanceinteriors.com Phone: (425) 459-4029 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.

    Designing for the Life Ahead: How Homes Can Support Every Stage of Family Life

  6. May 22

    Where Wealth Meets Identity: Finding Voice Inside the Family Legacy

    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 families navigate the emotional dimensions of money. Through her work in family enterprise consulting, she supports multigenerational families as they move through questions of succession, governance, identity, and the relational complexities that wealth can create across generations. Our conversation explores how families can better understand the personal stories and inherited expectations shaping the way wealth is experienced, discussed, and shared. We talk about the space between belonging to a family system and becoming more fully oneself, especially when identity, autonomy, culture, and legacy are all in motion. We also look at what can happen when inherited expectations meet individual growth, and how curiosity, honest reflection, and openness across generations can help families find shared direction while making room for each person to understand who they are, where they belong, and how they contribute. About Dr. Shay Harris-Pierre Dr. Shay Harris-Pierre is a clinically trained consultant and therapist working at the intersection of family relationships, wealth, and identity. She is a Licensed Professional Counselor and Certified Financial Therapist with nearly fifteen years of clinical experience helping individuals, couples, and families navigate the emotional and relational dimensions of their financial identities. She also holds a certificate in Family Business Leadership and training in Her work is grounded in a single observation: what looks like a financial problem is almost always also a relational and identity problem. She brings that lens into family enterprise consulting, financial planning partnerships, and wealth advisory spaces, helping multigenerational families navigate succession, governance, and the relational complexity that wealth creates across generations. Resources discussed in this episode: Irving Allam - The Gift of Therapy Bowenian Concept Murray Bowen Strangers in Paradise Blair Tripp - Progenitor's Dilemma Contact Cory Gagnon | Beacon Family Office at CI Assante Financial Management Ltd.  Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn: Beacon Family Office Email: beaconfamilyoffice@assante.com Contact Shay Harris-Pierre | Continuity Family Business Consulting:  Website: harrispierreconsulting.com LinkedIn: Dr. Shay Harris-Pierre Email: shaywanna.harris@yahoo.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.

    Where Wealth Meets Identity: Finding Voice Inside the Family Legacy

  7. May 8

    Reflection Over Reaction: How Families Improve Decision-Making in Family Enterprises

    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, family enterprise advising, and systems coaching, Aileen brings both professional depth and lived understanding to her work. Her roots in a farming family, experience as an entrepreneur, and work as co-author of Inspired Wealth: Financial Leadership for the 21st Century all shape the way she supports families through questions of wealth, ownership, legacy, and change. Our conversation explores what can happen when families slow down long enough to notice the patterns shaping their decisions. We talk about the space between what has been inherited and what can still be chosen, especially when legacy, ownership, and relationships are all in motion. We also look at why families sometimes need to pause before they can move forward and how honest reflection, careful listening, and openness to new ways of thinking can create more room for trust, learning, and better decisions across generations.About Aileen Miziolek  Aileen is a consultant with The Family Business Consulting Group, where she helps business-owning families navigate the complexities of continuity, succession, estate planning, and intergenerational wealth transfer. With more than 20 years of experience in complex financial and estate planning, she brings a multidisciplinary perspective to her work as a Certified Financial Planner, Family Enterprise Advisor, Certified Coach, and Organization and Relationship Systems Coach. What makes Aileen’s perspective unique is that she understands family enterprise from both a professional and personal lens. Her family business roots began in farming, and as a young entrepreneur, she launched her first start-up at age 25 before selling her first business a few years later. Contact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd.  Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn: Beacon Family Office Email: beaconfamilyoffice@assante.com Contact Aileen Miziolek | The Family Business Consulting Group Inc. Website: aileenmiziolek.com Instagram: @aileenmiziolek LinkedIn: Aileen Miziolek Email: miziolek@thefbcg.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.

    Reflection Over Reaction: How Families Improve Decision-Making in Family Enterprises

  8. Apr 24

    Leading Before the Role: How Family Enterprises Shape Future Leaders

    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 research-based insight to how families prepare the next generation and work through the questions that continuity raises across generations. Our conversation explores how families navigate expectations that are often left unspoken, why learning together matters, and what helps create more honest and mature conversations across generations. We also look at where tension can quietly build over time and how greater trust and clarity can help families move forward well.About Wendy Sage-Hayward Wendy is a senior consultant with The Family Business Consulting Group, where she advises business leaders, family enterprises, and boards around the world on how to navigate the complexities of continuity, governance, and generational transition. What makes Wendy’s perspective unique is that she doesn’t just advise family businesses. She lives it. She’s an owner of Sage Hayward Vineyards, her family’s winery on British Columbia’s Southern Gulf Islands, and previously served as a partner and director in her family’s five-generation U.S. business. Wendy is also the Academic Director at Family Enterprise Canada, where she leads the Family Enterprise Advisor program, and she teaches in the Family Shift program at Ivey Business School. She’s the co-founder of mGen Education and co-author of 'Human Resources in Family Business' and 'Own It!', bringing both practical and research-based insights to her work. She’s based in Vancouver and is passionate about helping families build strong businesses and even stronger relationships across generations. Resources discussed in this episode: Jay Hughes David York University of Alberta Alexander Saunders John Ward - Unconventional Wisdom Own It! How to Develop Family Enterprise Ownership Skills At Every Age Contact Cory Gagnon | Beacon Family Office at CI Assante Financial Management Ltd.  Website: BeaconFamilyOffice.com LinkedIn: Cory Gagnon LinkedIn: Beacon Family Office Email: beaconfamilyoffice@assante.com Contact Wendy Sage-Hayward | The Family Business Consulting Group:  Website: mgeneducation.com | thefbcg.com | familyenterprise.ca | sagehaywardvineyards.com LinkedIn: Wendy Sage Hayward Email: wsagehayward@gmail.com Phone: (604) 803 7420 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.

    Leading Before the Role: How Family Enterprises Shape Future Leaders
See All (75)

Trailer

About

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!

Information