Legacy Builders: Strategies for Building Successful Family Enterprises

In this episode, we’re joined by Mitchell Spearman, Director of Strategic Partnerships at Winn Family Foundation Inc. An attorney by training, Mitchell has spent over 20 years working with ultra-high-net-worth families, helping connect their philanthropic goals with opportunities in education and research. His experience includes securing over $500 million in philanthropic commitments across four continents, including a $100 million investment involving three generations of one family. Our conversation looks at how families develop shared values, prepare future leaders, and create opportunities for each generation to participate in shaping the family's future.

Mitchell also addresses the importance of understanding what th...

In this episode, we’re joined by David Lesperance, Managing Director at Lesperance & Associates. With over 30 years of experience advising high-net-worth and ultra-high-net-worth individuals and their families, David brings an international tax, residency, and citizenship planning perspective to the decisions families face across borders. Our conversation looks at how changing tax policies can prompt families to rethink where they live and hold their assets, the options available to them, and the obligations that accompany a move.

David also addresses how these choices affect everyday family life. A financially sound move needs to work for the people making it...

In this episode, we’re joined by Perry Gladstone, a confidential coach, advisor, and family enterprise transition specialist at Perry Gladstone Consulting. Drawing on his experience building and selling Limited Snowboards and reinventing himself along the way, Perry brings a personal understanding to the decisions facing founders and rising-generation leaders. Our conversation considers how unspoken expectations influence the roles family members accept, what it means to honour a legacy while retaining personal choice, and why founders need support in discovering who they want to be as their responsibilities change. We also discuss Perry’s approach to an “individual succession plan”...

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...

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 prepar...

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 fa...

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 ye...

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...

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, co...

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 ed...

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...

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 li...

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 pe...

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 sh...

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 an...

In this episode, we’re joined by David York, director at York Howell. David practices law in the areas of estate planning, tax, business planning, and non-profit entities. He is a fellow of the American College of Trust and Estate Counsel and a dean with the Purposeful Planning Institute. Chambers and Partners has recognized him in Estate Planning, a distinction awarded to approximately the top 2% of attorneys in the field. He is also the author of The Gift of Lift: Harnessing the Power of Stewardship to Elevate the World, Entrusted, and the children’s book Dudley’s Castle. Our conver...

In this episode, we’re joined by Alexander Saunders, Practice Director at Dialogos. Alex is a generative facilitator working at the intersection of dialogue, leadership, and complex human systems. Through work across the entertainment, venture capital, and hospitality sectors, as well as his own fifth-generation family business and other family-owned enterprises ranging from single-site operations to global hospitality groups, he brings both practical experience and scholarly grounding to the challenges of leadership, transition, and belonging within family enterprise. Our conversation focuses on what it means to find your place when identity, expectation, and opportunity become deeply intertwined, and on ho...

In this episode, we welcome Dr. Charles Eckhart, Founder and Managing Partner of Cathexis Group, a family engagement and governance consulting firm based in Santa Barbara, California. Charles advises enterprising families and couples of significant wealth through major transitions, helping them strengthen family governance and build collaborative decision-making practices that endure across generations. He also works closely with financial institutions to train and support advisors in navigating family dynamics with greater clarity and confidence. Drawing on his background as a clinical psychologist and academic instructor, Charles brings a thoughtful, grounded perspective to the intersection of family wealth, legacy, governance...

In this episode, we’re joined by Jeff Savlov, Founder of Blum & Savlov, LLP. For over 25 years, Jeff has helped family businesses, high-net-worth families, and their advisors balance family dynamics with the management of shared assets across generations. Drawing from his experience in his own family’s business, Jeff brings a grounded, common-sense perspective on how families can reduce conflict before it escalates and build healthier patterns that last. Our conversation focuses on what gets passed down beyond money: the spoken and unspoken family narratives that shape responsibility, resilience, identity, and ultimately, stewardship.

Jeff shares reflections shaped by b...

In this episode, we’re joined by Jennifer East, Founder of ONIDA Family Advisors. With nearly 20 years of experience guiding affluent and enterprising global families, Jennifer brings a cross-cultural lens to the inner dynamics of continuity, especially when individual identity and family legacy quietly collide. We explore why it’s so common for next-gen leaders to inherit expectations before they’ve defined their own path, and how intentional mentorship, emotionally aware leadership, and thoughtful facilitation can begin to shift that pattern. Together, we consider how families move from unspoken assumptions to shared clarity and why making space for reflection may be...

In this episode, we’re joined by Amy Stein, Chief Impact Officer at Generations Trusted Family Business Advisors. With over 20 years in her family’s fourth-generation business, Henry’s, and experience launching its mental health foundation, Amy brings a rare perspective on legacy, leadership, and impact. Our conversation focuses on what transition really feels like, how identity shifts, how clarity emerges through change, and how purpose can take on new meaning when familiar roles evolve. It’s a personal, layered look at the emotional side of stepping into what’s next.

Amy shares reflections shaped by lived experience...

In this episode, we’re joined by Susan Latremoille, Co-Founder and Partner at Next Chapter Lifestyle Advisors. With more than 35 years of experience as a wealth advisor, including leadership roles on RBC’s Chairman’s Council and the board of Richardson Wealth, Susan now helps clients and advisors plan for the human side of life transitions. As a Certified Exit Planning Advisor and Retirement Coach, she invites us to rethink what comes after the sale of a business or the end of a career, not just financially, but emotionally and personally. We discuss how to clarify purpose beyond work, reigni...

In this episode, we’re joined by Russel Baskin, a consultant and certified executive coach with Trella Advisory Group. Drawing from her background in human development and two decades of experience with business families, Russel helps name what often goes unspoken in transition, how control, identity, and legacy quietly shape relationships and decision-making. From habitual patterns to intergenerational tension, she invites us to consider how emotional insight and structural clarity work together in succession. 

Her approach emphasises empathy, shared understanding, and space for each generation to grow into their role with intention. If you're supporting a family in...

In this episode, Dr. Julia Edelman, board-certified gynecologist, author, and nationally recognized menopause expert, joins us to open a conversation we’ve never had on Legacy Builders: the impact of women’s health, specifically menopause, on family enterprise. A Yale, Columbia, and Harvard-trained physician with over four decades of experience, Dr. Edelman brings both clinical authority and compassionate insight to a topic that touches individuals and family systems alike.

Together, we examine how menopause, often unspoken and misunderstood, can shape communication, influence decision-making, and affect readiness for leadership transitions. You’ll hear how silence around these experiences can er...

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 re...

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...

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 g...

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 r...

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...

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...

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...

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...

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...

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 ca...

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...

In this episode, we welcome Purdeep Sangha—Director of Sangha Worldwide, trusted advisor to CEOs and board members, and co-host of Mind Your Own Business. Known for helping leaders operate at their highest potential, Purdeep brings a unique perspective rooted in neuroscience, performance psychology, and ancient wisdom. Together, we explore what it takes to sustain peak performance while maintaining personal harmony, touching on relationship dysfunction, energy management, courageous decision-making, and what it means to become a truly Complete Man in work, family, and life.

Throughout our conversation, Purdeep challenges the belief that professional excellence alone defines success. He...

In this episode, Dr. Sharilyn Hale, President of Watermark Philanthropic Counsel, shares her expertise from over twenty-five years in philanthropy as a trusted advisor helping clients channel wealth and influence for positive impact. As a Chartered Director, advisor with 2164, faculty member of the Ultra High Net Worth Institute, and instructor at Carleton University, Dr. Hale brings unique insights from her doctoral research that produced an innovative governance model for family giving—work recently recognized with a 2025 Family Wealth Report Award. In our conversation, we explore purpose-driven wealth stewardship, the delicate balance between individual and collective values in family philanthropy, an...

In our upcoming episode, we explore the essential strategies for aligning values and purpose across family enterprise systems with Holly Simmons, Principal Managing Partner at Golden Lasso Consulting and Family Enterprise Advisor. This conversation examines how leadership development, effective communication, and clear role definition serve as foundational elements for sustainable growth and family harmony in business settings. Listeners will gain insights into balancing individual needs with collective goals, building stronger relationships through intentional practices, and creating systems that honour both personal contributions and shared heritage

During our discussion, listeners can look forward to exploring the balance between...

In this episode, Emily Bouchard, Chief Learning Officer at 10x10 Roadmap and Founder of Bouchard Bespoke Consulting, shares her extensive expertise on helping wealthy families navigate the complexities of multigenerational wealth, relationships, and leadership. With over 20 years of experience coaching families, Emily offers valuable insights on developing healthy identities for family members regardless of their relationship to family wealth.

Throughout the conversation, Emily explores crucial concepts such as the unique challenges faced by young people in affluent families, the importance of operationalizing family values, and creating purposeful prenuptial agreements that strengthen relationships rather than undermining them. She...

In this episode, Gerard McInnis, Senior Partner at Kalos Transactions Advisory, MacKay CEO Forum Chair, and Chair of the Board at Cashco Financial Services Inc., shares his expertise on valuation principles and strategic capital structure for family enterprises. With over 30 years of experience in business valuations, strategy, governance, and operations, Gerard explores how businesses can optimize their approach to value creation while navigating succession planning and intergenerational transitions.

Throughout the conversation, Gerard delves into essential concepts like the three types of business leaders, capital structure optimization, and practical approaches to strategic planning that drive sustainable value. He...