Legacy Builders: Strategies for Building Successful Family Enterprises

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Legacy Builders: Strategies for Building Successful Family Enterprises

Cory Gagnon

58 episodes

1 week ago

Cory Gagnon doesn’t just love supporting multi-generational families every day. He loves digging into topics and sharing information that matters to family enterprises! In Legacy Builders: Strategies for Building Successful Family Enterprises, Cory, Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd, dives deep to share ways for business owners, family stewards, and the rising generation in family enterprises to take control of their wealth and build a lasting legacy. Through interviews with industry experts, each episode provides understandable and actionable strategies and insights on complete wealth management. From navigating family dynamics to developing a successful wealth transition plan and everything in between, this is the podcast to bring your legacy into the future. Subscribe today!

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Entrepreneurship

Self-Improvement,

All content for Legacy Builders: Strategies for Building Successful Family Enterprises is the property of Cory Gagnon and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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!

Show more...

Entrepreneurship

Self-Improvement,

Episodes (20/58)

Legacy Builders: Strategies for Building Successful Family Enterprises

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

In this episode, we’re joined by Keita Demming, Partner at The Covenant Group, award-winning author of Strategy to Action, and trusted advisor in strategy, design, and innovation. We explore how strategy becomes a lived practice through intentional behavior, 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.

1 week ago

50 minutes 44 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

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

In this episode, we’re joined by Jenna Carvalho, Founder and Principal of Guardian Estate Company, whose work sits at the intersection of estate planning, family relationships, and meaningful legacy. With more than 100 estates and dozens of trusts under her direct care, Jenna has witnessed the full spectrum of outcomes, both smooth and strained, when families face the inevitable transitions that come with wealth, loss, and leadership. We talk about what it’s really like to act as an executor for the first time, how communication (or the absence of it) can change everything, and why estate planning is less about predicting the future and more about preparing people for it. What happens when intentions go unspoken? When roles aren't clearly understood? And when decisions once thought simple suddenly carry emotional weight?

3 weeks ago

44 minutes 29 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

The Stories That Hold Us: Why Capturing Memory Is a Strategic Act of Care

In this episode, we’re joined by Andrea Lekushoff, founder and CEO of CONTEXT Studios, where personal stories become powerful tools for connection, continuity, and leadership. We talk about the invisible value of lived experience, how one person’s reflections can clarify identity, honor 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?

1 month ago

46 minutes 46 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Developmental Crises: Helping Leaders and Families Grow Through Defining Moments

In this episode, we’re joined by Dr. Paul Edelman, a Harvard-trained psychologist and longtime advisor to leaders and families navigating complex transitions. What if uncertainty isn’t something to fix, but something to learn from? What if discomfort could actually move us forward? Together, we explore these questions and more looking at how moments of disorientation can deepen clarity, stretch capacity, and strengthen connection across generations.

1 month ago

44 minutes 27 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

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

In this episode, Dr. Dennis T. Jaffe, Senior Research Fellow at BanyanGlobal Family Business Advisors, joins us to explore how family enterprises can evolve with intention across generations. A globally recognised adviser, educator, and author of Wealth 3.0 and Borrowed from Your Grandchildren, Dennis brings decades of insight into how families build shared purpose, navigate complexity, and sustain legacies that matter.

2 months ago

46 minutes 59 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Past, Present, and Possibility: Reimagining Legacy Through Story

In this episode, Julia Chung, Co-Founder and CEO of Spring Planning, joins us to explore the kinds of questions that can reshape a family’s future. As Board Director and FEA Community Council Chair at Family Enterprise Canada, and Chair of the Financial Planning Association of Canada’s Board, Julia brings a depth of experience that turns difficult conversations into turning points. Together, we venture into the spaces where legacy is defined, identity is examined, and agency is reclaimed.

2 months ago

46 minutes 37 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

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

In this episode, Shauna Trainor, Principal at A&O Partners, invites us into the often overlooked spaces where clarity, courage, and connection shape the future of enterprising families. Drawing from her background in business, psychology, and systems thinking, Shauna helps us reframe how family conversations become the foundation for shared decision-making across generations.

3 months ago

45 minutes 26 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

The Fear of Ugly: Reframing Conflict in Family Enterprise Communication

In this episode, Jane Beddall, founder of Dovetail Resolutions, helps us reframe how conflict shows up in family enterprises. Drawing on her experience as a mediator, consultant, and conflict coach, Jane shares why not all conflict is the same—and how the fear of escalation often prevents families from addressing tension early. We explore the distinction between healthy disagreement and deeper dysfunction, and why timing, environment, and tone matter more than we often realize.

3 months ago

46 minutes 5 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

The Courage to Continue: Why Emotional Readiness Shapes Enterprise Legacy

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.

4 months ago

45 minutes 34 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Breaking the Log Jam: Clearing Complexity to Build Sustainable Family Wealth

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.

4 months ago

48 minutes 15 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Breaking the Pattern: How Self-Awareness and Choice Transform Family Wealth Dynamics

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, and life.

4 months ago

49 minutes 33 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Unlocking Full Potential: The Intersection of Peak Performance and Personal Harmony

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.

5 months ago

50 minutes 39 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Strategic Participation Models: Optimizing Multi-Generational Philanthropic Engagement

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, and how governance structures can enhance rather than hinder authentic engagement across generations.

5 months ago

58 minutes 13 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

The Family Mirror: Why Self-Improvement Creates Systemic Change in Business Families

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

6 months ago

47 minutes 48 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Wealth Beyond Money: Cultivating Trust, Identity, and Connection in Family Enterprises

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.

6 months ago

48 minutes 8 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Hardwired for Value: How Strategic Capital Structure Shapes the Future of Your Family Enterprise

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.

7 months ago

50 minutes 18 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

The Decision Catalyst: Examining Keep-or-Sell Frameworks in Family Enterprise

In this episode, Paul Hood, one of the most influential voices in purposeful planning and family business governance, navigates the complex terrain of family business decision-making and succession planning. With decades of experience as a tax attorney, educator, and trusted advisor featured in Forbes, USA TODAY, and The Wall Street Journal, Paul reveals what truly matters when families face their most critical crossroads: whether to keep or sell their business

7 months ago

46 minutes 9 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Rethinking Governance: Modern Strategies for Stronger Boards & Better Decisions

In this episode, Matt Fullbrook, one of North America's most recognizable voices in corporate governance, explores the nuanced world of boardrooms and what truly makes them effective. With over two decades of experience in more than 300 boardrooms, Matt challenges conventional wisdom about what it means to be "skilled" and how boards can function at their highest potential despite uncertainty.

8 months ago

50 minutes 37 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

Shaping Next-Generation Owners: Lessons in Resilience, Responsibility, and Leadership

In our latest episode, Dave Specht, Director of the Drucker School Global Family Business Institute and author of "The Family Business Whisperer," shares his insights on developing ownership mindsets across generations. With an expansive career that includes training over 2,500 advisors and bankers on family dynamics, founding Advising Generations, and establishing the Family Business Management program at the University of Nebraska, Dave brings a powerful blend of academic wisdom and practical experience to help families navigate the intricate path of generational continuity.

8 months ago

45 minutes 19 seconds

Legacy Builders: Strategies for Building Successful Family Enterprises

The HERO in Family Enterprise: The Mindset to Guide the Rising Generation

In this episode, Doug Gray, Ph.D., Founder and CEO of Action Learning Associates, LLC and co-Founder of Assess Next Gen, LLC, shares his expertise on fostering psychological capital (PsyCap) and intergenerational understanding within family enterprises. With over 25 years of experience and a deep background in leadership development, Doug explores how families can build stronger connections across generations while managing wealth and legacy dynamics.

9 months ago

42 minutes 13 seconds