Legacy Builders: Strategies for Building Successful Family Enterprises

In this episode, Cory Gagnon joins Gavin Brower and Gerry Meyer to discuss what really shapes a successful transition inside a family enterprise. Expectations around leadership, ownership, timing, and readiness can easily drift apart when they remain unspoken. One generation may be thinking about succession while another is still deciding whether they want a role at all. Gavin and Gerry explore how families can surface those differences earlier, create clearer accountability, and build enough trust to have the conversations that are often easiest to postpone.

Drawing from their experience in organizational leadership, governance, succession, and family enterprise strategy, they look at what happens when vision has to move from intention into practice. The discussion touches on preparing successors, separating ownership from employment, creating formal development paths, making space for rising-generation leaders, and helping long-standing leaders rethink what stepping back can actually look like. Along the way, they return to a common thread: transition works better when families understand where they are going, what role each person is expected to play, and how progress will be measured.

About Gavin Brauer

Gavin is a versatile entrepreneur and Professional EOS Implementer who helps organizations across various industries, including health tech, manufacturing, consumer brands, professional services, and non-profits, to dream big and execute using a proven system for running a successful business. He has owned and operated three unique ventures: KindHuman Bicycles, which crafts high-performance bikes, runs a bike shop, and distributes custom cycling apparel; Pearl Interactives, a health-tech start-up co-founded with a children's hospital to develop video games that enable kids with disabilities to access wellness through play; and a turnaround business that ultimately did not succeed. Alongside his entrepreneurial pursuits and EOS implementation, Gavin collaborates with his father in managing their family office.

Contact Gavin Brauer | EOS Worldwide: 

• Website: eosworldwide.com/gavin-brauer/
• LinkedIn: Gavin Brauer
• Instagram: @kindhuman_canuck
• Email: [email protected]

About Gerry Meyer

Gerry is the founder of Meyer Advisory Group. He is a highly experienced leader and enabler of organization effectiveness and transformation with 36+ years as an HR practitioner, consultant, and advisor. He provides trusted, authentic, and values-based leadership across a diverse range of business environments, including public and private sectors, family enterprises, non-profit, real estate, high-tech, and professional services industries. He advises on a broad range of business issues including HR and business strategic planning, executive/leadership recruitment, next-generation development and succession planning, talent acquisition and retention, employee performance development and high-potential programs, executive compensation and total rewards, and business and family governance. 

His experience encompasses multiple business cycles in different industries, including upswings and downswings – seeing both growth and recessionary markets and addressing the realities of each. Gerry holds a CPHR (“Chartered Professional in Human Resources”) and FEA (“Family Enterprise Advisor”) designation as well as a Bachelor of Economics and Labour Relations from Carleton University. 

Contact Gerry Meyer | Meyer Advisory Group 

• Website: meyeradvisorygroup.com
• LinkedIn: Gerry Meyer
• Email: [email protected]
• Phone: (778) 980-0734

Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd. 

• Website: BeaconFamilyOffice.com
• LinkedIn: Cory Gagnon
• LinkedIn: Beacon Family Office
• Email: [email protected]

Resources discussed in this episode:

• Toronto Maple Leafs
• Vision Traction Organizer
• Patrick Lencioni

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In this episode, we’re joined by Devin DeCiantis, Managing Partner at Lansberg Gersick Advisors. Devin has spent years studying how family enterprises endure across generations, focusing on governance, risk, and resilience. Our conversation explores how culture and history shape the way families respond to uncertainty, why long periods of stability can create complacency, and what it means to build resilience before a crisis arrives deliberately. We also discuss intergenerational responsibility, migration, institutional trust, and the idea of paying a “resilience tax” today to strengthen an enterprise for tomorrow.

Devin invites us to consider how families can prepare for a future that may look very different from the past, while building the capacity to adapt, endure, and continue across generations.

About Devin DeCiantis

Devin DeCiantis is a trusted advisor to the world’s leading family enterprises and the Managing Partner at Lansberg Gersick Advisors (LGA). With an MPP from the Harvard Kennedy School and years of research into organizational continuity, Devin and his team help business families design robust governance systems that bridge the gap between short-term goals and long-term stewardship. He is the co-author of "The Enduring Enterprise" and the forthcoming book, "Governing Complex Family Enterprises: The Seven Drivers of Continuity".

Resources discussed in this episode:

• The Enduring Enterprise
• Governing Complex Family Enterprises: The Seven Drivers of Continuity (Upcoming)
• Generation to Generation: Life Cycles of the Family Business
• Succeeding Generations
• Jim Grubman
• Dennis Jaffe

Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd. 

• Website: BeaconFamilyOffice.com
• LinkedIn: Cory Gagnon
• LinkedIn: Beacon Family Office
• Email: [email protected]
• Podcast: Legacy Builders Strategies for Building Successful Family Enterprise

Contact Devin DeCiantis | Lansberg Gersick Advisors (LGA)

• Website: lga.global 
• LinkedIn: Devin Deciantis 
• Newsletter: The Resilience Playbook Newsletter
• Email: [email protected]

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In this episode, Cory Gagnon is joined by Judi Cunningham and Tom McCullough for a timely conversation on how families can make better decisions together. From estate plans to ownership transitions, it’s rarely the decisions themselves that hold families back; it’s the buildup around them. Roles are unclear. Assumptions go unspoken. And sometimes, one voice dominates when collaboration is what’s really needed. Judi and Tom share what gets in the way, and more importantly, how families can start moving forward with clarity, confidence, and trust.

Pulling from years of experience in family systems, governance, and family office strategy, they offer practical tools for navigating complexity without losing momentum. Whether it’s building development plans for the next generation, turning good intentions into written agreements, or understanding who actually gets to decide what, this session is packed with insight. If your family is working through a transition or trying to avoid the next standstill, this conversation will help you create more alignment without overcomplicating the process.

About Tom McCullough 

Tom McCullough is Partner at Corient and Managing Director at The Ultra High Net-worth Institute, the leading Canadian multi-family office. He has spent over 35 years in the wealth management/family office field.

Tom is a frequent speaker on issues relevant to families of wealth and is the co-author of Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask and Family Wealth Management: 7 Imperatives for Successful Investing in the New World Order. He is an Adjunct Professor and Executive-in-Residence at the University of Toronto’s Rotman School of Management MBA program. He is an Entrepreneur-in-Residence at Western University’s Ivey School of Business and a member of the Editorial Board of the Journal of Wealth Management. He was recently awarded ‘Best Individual Contribution to Thought Leadership in the Wealth Management Industry’ by the 2020 Family Wealth Report Awards.

Contact Tom McCullough | Corient

About Judi Cunningham

Judi Cunningham is the Founder and Senior Consultant at Trella Advisory Group, a consulting firm that works with family enterprises and families of wealth. With a Master’s in Family Systems Counseling and over 25 years of experience, she excels in navigating complex family dynamics and business challenges. Judi’s strategic insight and facilitation skills help families find alignment and address tough decisions. Judi is known for her innovative educational initiatives. She pioneered the Family Enterprise Advisor Program, establishing global standards for professional advisors. In addition to her for-profit work, Judi volunteers her time to support multi-generational family success. She serves as the Chair of the Board for the Purposeful Planning Institute, which helps advisors serve families of wealth and families in business.

Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd.

Resources discussed in this episode

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In this episode, we’re joined by Katherine Bright, Family Enterprise Consultant at Trella Advisory Group. For nearly two decades, Kathy has helped family businesses navigate the decisions, relationships, and responsibilities that shape continuity across generations. Her work spans consulting, education, and board service, giving her a grounded understanding of the challenges families, boards, and advisors face when certainty gives way to change. Alongside her client work, she teaches and develops training for family enterprise professionals, focusing on leadership, succession, governance, strategy, risk, and productive family relationships. Our conversation explores the role curiosity can play when answers are not yet clear, including the fine line between anxiety and excitement, how families and boards respond to uncertainty, and what can emerge when failure is treated as part of growth.

Kathy invites us to consider what becomes possible when families loosen their grip on certainty, ask better questions, and keep choosing one another even when the path forward is still taking shape.

About Kathy Bright

Katherine Bright is a Family Enterprise Consultant at Trella Advisory Group and has worked in the family enterprise world for nearly twenty years. As a consultant, educator, and board director, she works with family businesses to help them thrive across generations. In addition to supporting family enterprise clients, Kathy also guides advisory professionals, helping them better understand the complex needs of family business clients.

From university teaching to tailored training programs for family enterprise advisors and family enterprises, Kathy’s expertise as an educator combines both technical guidance and strong interpersonal connections. She also brings extensive hands-on experience with strategy and governance through her service on multiple family business, government, and not-for-profit boards. Kathy is passionate about leadership, succession and continuity planning, strategy, risk management, governance structures, fiduciary responsibility, and helping families maintain positive and productive relationships within their enterprises.

Resources discussed in this episode:

Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd. 

Contact Kathy Bright | Trella Advisory Group

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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. 

Contact Kirby Rosplock | Tamarind Learning

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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:

Contact Cory Gagnon | Beacon Family Office at CI Assante Wealth Management Ltd. 

Contact Grant Conroy | Genus Capital Management: 

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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.: 

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: 

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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.

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.

Website: https://www.watsoninc.ca/ | westviewsearch.ca

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.

Website: catalyst-strategies.com | valuedriver.ca

Resources discussed in this episode:

Contact Cory Gagnon | Beacon Family Office at CI Assante Financial Management Ltd.: 

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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. 

Contact Sarah Walker | Nuance Interior Design: 

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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:

Contact Cory Gagnon | Beacon Family Office at CI Assante Financial Management Ltd. 

Contact Shay Harris-Pierre | Continuity Family Business Consulting: 

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