Legacy Builders: Strategies for Building Successful Family Enterprises

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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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. 

Contact Aileen Miziolek | The Family Business Consulting Group Inc.

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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:

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

Contact Wendy Sage-Hayward | The Family Business Consulting Group: 

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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 conversation focuses on what it means to approach wealth, legacy, and family with deeper self-awareness and on how humility, curiosity, and stewardship can shape the way families prepare for responsibility, continuity, and long-term impact.

We talk about why humility matters in the way we learn, lead, and prepare the next generation, some of the fears that can quietly shape family decisions over time, and the shift from simply owning wealth to stewarding it with greater purpose. Together, we explore what may be happening beneath the surface before families ever make the big decisions and how greater self-awareness can help families lead, relate, and navigate complexity with more intention across generations.

About David York

David R. York is an attorney, Certified Public Accountant, and Managing Partner at York Howell. He practices in the areas of estate planning, tax, business planning, and nonprofit entities and is widely recognized for his work with ultra-high-net-worth families. He is a Fellow of the American College of Trust and Estate Counsel, a Dean with the Purposeful Planning Institute, and has been recognized by Chambers and Partners in estate planning.

David is also the author of The Gift of Lift, Dudley’s Castle and the co-author of Entrusted and Riveted. In addition to his legal work, he speaks and teaches on stewardship, purpose, and legacy and co-founded Corenology™, a platform designed to help people connect their values with planning. He serves on the Board of Directors of Healing Nations and lives in the Salt Lake City area with his wife, Mindy, and their five children.

Resources discussed in this episode:

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

Contact David York | York Howell 

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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 how families can create the conditions for people to grow into responsibility with greater clarity and readiness.

We talk about the tension between being invited in and truly feeling ready, the importance of mentors and support systems during seasons of transition, and why self-awareness can be such a critical foundation for contribution and governance. Together, we explore how family enterprises can strengthen the relational fabric that helps individuals grow, lead, and navigate complexity in healthier and more sustainable ways.

About Alexander Saunders 

Alex is a generative facilitator working at the intersection of dialogue, leadership, and complex human systems. He has built and supported organizations across the entertainment, venture capital, and hospitality sectors, including his own fifth-generation family business and other family-owned enterprises ranging from single-site operations to global hospitality groups. He holds a Master's degree in Economics and Classics, bringing both practical and scholarly grounding to his work with leaders navigating complexity and transition.

Resources discussed in this episode:

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

Contact Alexander Saunders | Dialogos

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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, and relationships. Our conversation centres on how families can prepare the rising generation not just to inherit resources but to develop the resilience and judgment required to steward them well.

With a posture of curiosity, we explore how meaningful growth often comes through “earned” experiences and how families can model vulnerability, responsibility, and even mistakes in ways that strengthen confidence rather than diminish it. Together, we consider how intentional culture-building can help families move from overprotection to purposeful preparation, supporting capable next-generation leaders with both strength and humility.

About Charles Eckhart

Dr. Charles Eckhart is the founder and managing partner of Cathexis Group, a family engagement and governance consulting firm based in Santa Barbara, California. He works with families and couples of significant wealth to support family transitions and build governance practices that strengthen collaborative decision-making and long-term alignment. He also partners with financial institutions to train and support wealth advisors in family dynamics and governance.

Before founding Cathexis Group, Charles built his career as a clinical psychologist, including academic teaching and training roles in doctoral clinical training programs. He contributes publications, presentations, and thought leadership at the intersection of family wealth, legacy, governance, and relationships.

Resources discussed in this episode:

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

Contact Charles Eckhart | Cathexis Group

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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 both clinical training and real-world work with multigenerational families. We talk about intentional storytelling, optimal challenge, and early-life parenting choices, and how starting earlier can help families move from reactive regret to proactive stewardship, with more clarity and less friction.

About Jeff Savlov

Jeff Savlov is the founder of Blum & Savlov, LLP – Family Business & Wealth Consulting. He advises family businesses, high-net-worth families, and family offices on balancing family dynamics with shared ownership and management across generations. He’s especially known for helping parents raise children in a family enterprise context, so wealth supports healthy, productive outcomes. Jeff speaks in the U.S. and internationally, has been quoted in The New York Times and Family Business Magazine, and writes “The Family Business Minute.”

With 25+ years spanning business leadership and advanced training in family systems, group dynamics, and psychoanalytic work, Jeff brings a practical, common-sense approach to complex family-enterprise challenges. A Fellow of the Family Firm Institute, he has also consulted with Fortune 500 companies, including Bristol-Myers Squibb, Johnson & Johnson, and Schering-Plough. He lives in New Jersey with his wife and two children and brings creativity and a sense of humor to his work.

Resources discussed in this episode:

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

Contact Jeff Savlov | Blum & Savlov, LLP – Family Business & Wealth Consulting

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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 one of the most powerful choices they make.

Jennifer shares grounded insight shaped by lived experience across cultures and decades of work with rising generations. We talk about leadership development, intergenerational collaboration, and the quiet courage it takes to name what’s true before the next chapter can begin.

About Jennifer East

Jennifer East is the Founder of ONIDA Family Advisors, where she empowers affluent, enterprising global families to transition their wealth, businesses, and the values that drive their success. With nearly two decades of experience, Jennifer brings a strategic, people-centered approach to helping families strengthen intergenerational collaboration, improve family dynamics, and build governance practices that support long-term continuity and meaningful impact.

Having lived, worked, and raised her children across North America, Europe, and the Middle East, Jennifer offers invaluable insight into cross-cultural advising. She supports rising generations, particularly women and sibling/cousin teams, through personal and leadership development, and helps families integrate diverse perspectives into stronger governance. A Fellow of the Family Firm Institute (FFI), she holds the FFI GEN Advanced Certificate in Family Business Advising (ACFBA) and has served as faculty with FFI’s Global Education Network for the past nine years. Influenced by the Wealth 3.0 paradigm, Jennifer brings a strengths-based ethos that centers the human dynamics within families. She lives in Malta with her husband and two children.

Resources discussed in this episode:

• Us, by Terry Real
• Relational Life Institute
• Camden Education
• Camden Wealth

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

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

Contact Jennifer East | ONIDA Family Advisors: 

• Website: onida.ca
• LinkedIn: linkedin.com/in/jenniferakeast
• Email: [email protected]

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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 and thoughtful observation. We talk about resilience, voice, and the quiet work of preparing for change even when you don’t yet know what the next chapter will hold.

About Amy Stein

Amy Stein is the Chief Impact Officer at Generations Trusted Family Business Advisors, where she helps family enterprises and their family offices develop values-aligned philanthropic strategies that engage rising generations and create measurable impact. With a strategic, people-centred approach, she supports families in looking beyond financial metrics to integrate business, employees, customers, and community in meaningful ways. Her work focuses on designing initiatives that scale with intention, reflect legacy, and build lasting social capital.

For over two decades, Amy was a key leader in her family’s fourth-generation business, Henry’s, Canada’s largest independent imaging retailer. She later spearheaded the launch of the Foundation for Henry’s, a creative mental health initiative rooted in community impact. Drawing on deep experience in governance, strategy, and operations as a family member, executive, board member, and shareholder, Amy brings insight into the complex dynamics of family enterprise. She is especially skilled at bridging generational perspectives and helping families align purpose with action.

Resources discussed in this episode:

• Rotman School
• Pixel Foundation
• David Bentall
• Family Enterprise Canada

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

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

Contact Amy Stein | Generations Trusted Family Business Advisors: 

• Website: gtfba.com/ | pixelfoundation.org
• LinkedIn: Amy Stein
• Email: [email protected]

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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, reignite curiosity, and shape a next chapter filled with growth, meaning, and connection.

You’ll hear how Susan supports people in rediscovering dormant interests, building new social circles, and navigating the identity shifts that often accompany retirement. Whether you’re advising clients through a transition or preparing for one yourself, this conversation offers grounded, practical insight into making the most of what’s next.

About Susan Latremoille

Susan spent over 35 years as a wealth advisor, helping clients plan financially for retirement. Over time, she saw that financial readiness was just one part of the equation. The emotional and lifestyle aspects often had the greatest impact on whether clients thrived. This insight led her to co-found Next Chapter Lifestyle Advisors, where she now works as a certified Retirement Coach (CPRC), guiding individuals through meaningful, purpose-driven transitions.

She is a Certified Expert Level Practitioner of SuccessFinder, a CEPA, a Family Enterprise Advisor (FEA), and holds an Executive MBA. A former board member of Richardson Financial Group, she also holds the ICD.D designation from the Institute of Corporate Directors. Alongside her partner, Marianne Oehser, Susan teaches at the Exit Planning Institute. She is the author of The RichLife – Managing Wealth and Purpose, It’s Not Just About the Money, and co-author of On the Shoulders of Atlas and Thriving Throughout Your Retirement Transition. Her newest book, 9 Steps to a RichLife Retirement, offers a practical roadmap for living well, giving back, and leaving a legacy.

Resources discussed in this episode:

• Exit Planning Institute
• John Deere Dealership
• Happiness Portfolio 
• TIGER 21
• 9 Steps to a RichLife Retirement: Live Well, Give Back, Leave a Legacy

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]

Contact Susan Latremoille | Next Chapter Lifestyle Advisors: 

• Website: nextchapterlifestyleadvisors.com
• LinkedIn: Susan Latremoille
• Email: [email protected]
• Phone: 647-393-1785

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