Legacy Builders: Strategies for Building Successful Family Enterprises

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 foster resilience through shared learning, how emotional awareness influences decision-making, and why slowing down is often the smartest move in times of complexity. Tune in to hear how intentional structure, open dialogue, and a willingness to evolve can help families build a legacy with both strength and care.

About Krista Rabidoux

With over 24 years of experience in U.S.-Canada cross-border tax planning, Krista Rabidoux offers more than technical expertise, she brings a holistic perspective to family enterprise strategy. As both a tax professional and certified executive coach, her work focuses on the intersection of financial clarity and leadership development, helping families navigate transitions with confidence.

Her approach goes beyond compliance. Krista partners with clients to support rising generation leadership, strengthen team dynamics, and align business goals with family values. Whether guiding succession planning or evolving enterprise governance, she brings both the precision of a tax advisor and the insight of a coach.

Resources discussed in this episode:

• Buy Back Your Time: Get Unstuck, Reclaim Your Freedom, and Build Your Empire
• Rich Dad Poor Dad
• Strength Deployment Inventory
• 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 Krista Rabidoux | Andersen in Canada: 

• Website: ca.andersen.com
• LinkedIn: Krista Rabidoux 

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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 capital, aligning purpose with action, and creating legacies that last.

About Don Steele

A trusted advisor, financial executive, and investor passionate about helping entrepreneurs unlock the potential in their families and businesses. A valued partner and skilled collaborator, providing support and accountability to enterprising families and their advisors to preserve and nurture each family’s unique mix of financial and non-financial capital.

Resources discussed in this episode:

• Range: Why Generalists Triumph in a Specialized World
• Pioneering Portfolio Management
• Private Capital by Joe Reilly
• Purposeful Planning Podcast
• Built to Sell Podcast

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 Don Steele | Sterling Family Capital: 

• Website: sterlingfamilycapital.com
• LinkedIn: Don Steele
• Email: [email protected]
• Phone: (416) 302-2146

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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.

Throughout our conversation, Kristen challenges the belief that everyone must follow the same path to success within wealthy families. She shares why lasting fulfillment requires breaking free from unwritten rules and self-imposed pressures, emphasizing the courage to move beyond patterns of expectation that keep families stuck in cycles of obligation rather than authentic connection.

Tune in to discover how intentional family governance, role clarity, and balanced frameworks can unlock your family's potential to honor collective purpose while preserving personal autonomy across generations.

About Kristen Heaney 

Kristen Heaney, Founder & Coach of In Three Generations, LLC, is a Coach and Consultant to financially successful families and individuals who guides clients through the complex landscape of wealth and its associated challenges. Having lost her business-owning father to cancer at 21, she brings profound understanding to helping clients thrive amidst their success while managing the unique burdens that arise.

As both an "unprepared inheritor in recovery" and Consultant and Instructor to professional advisors serving wealthy families, Kristen specializes in authentic connection and understanding unique family needs. Her proven approach helps clients implement effective strategies for managing wealth challenges while maintaining deep relationships across generations.

Author of "In Three Generations: A Story about Family, Wealth, and Beating the Odds" and the children's book "The Super Special, Altogether Ordinary Day," Kristen creates inspirational content for those navigating unique struggles and intense celebrations. Her passion centers on helping successful individuals discover gratitude and purpose in their awesome work and relationships.

Resources discussed in this episode:

• www.in3generations.com
• The Quest for Legitimacy by Jamie Weiner

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 Kristen Heaney | In Three Generations LLC: 

• Website: in3generations.com
• LinkedIn: Kristen Heaney
• Instagram: @in3generations
• Email: [email protected]

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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 shares why lasting fulfillment requires internal alignment, emotional resilience, and the willingness to face uncomfortable truths that often limit our growth.

Tune in to discover how intentional self-work, courageous leadership, and personal alignment can unlock your full potential in business and life.

About Purdeep Sangha 

Purdeep Sangha is a North American leader in business and human performance who advises top Board Members, CEOs, and Entrepreneurs around the globe as their business strategist and personal performance advisor. He has a proven track record for helping business heavyweights master the game of business and life simultaneously. He co-hosts the newest TV series, "Mind Your Own Business," an eight-part series where each entrepreneur faces both an accessibility challenge and a business challenge, taking viewers deep into the lives of various business owners from the disability community.

Purdeep is well known for his unique expertise in scaling businesses through effective business strategy, execution, innovation, leadership, marketing, customer experience, and operations. He is also the foremost leader in ULTRA performance, helping professionals optimize their performance using neuroscience, performance psychology, and ancient teachings kept secret by the elite. His passion involves helping men discover their power in becoming The Complete Man—achieving ultimate performance, fulfillment, and victory in both business and personal life as the best possible business leader, husband, father, and man they can be.

Resources discussed in this episode:

• The Complete Man
• Substack Newsletter
• 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 Purdeep Sangha | Sangha Worldwide 

• Website: purdeep.substack.com
• LinkedIn: Purdeep Sangha
• Phone: (866) 918-4140
• Email: [email protected]

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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.

Throughout our discussion, Dr. Hale examines how intentional giving structures transform both individuals and family enterprises, challenging conventional wisdom about philanthropic engagement. She shares practical strategies for improving multi-generational participation, from creating voluntary on-ramps to developing diverse roles beyond board membership. Listen to our latest episode for valuable insights on building resilient family philanthropy systems that harmonize personal values with meaningful social impact—perspectives beneficial for family enterprise members and their advisors alike.

About Dr. Sharilyn Hale

Dr. Sharilyn Hale helps those who give, give well, engage their families, and channel their wealth and influence for good. Her highly customized engagements result in clients having greater confidence and clarity in their giving and governance. Sharilyn is an advisor with 2164 in support of multi-generational family philanthropy, a faculty member of the Ultra High Net Worth Institute, and an Instructor at Carleton University. A Chartered Director (C.Dir), Sharilyn blends the best of corporate and family governance in her work with private foundations and nonprofit boards, and her doctoral research produced a governance model that helps families give in a way that works. With more than 25 years of experience working in philanthropy and charitable communities, she was recently recognized with a 2025 Family Wealth Report Award for her work advancing philanthropy with UHNW families.

Resources discussed in this episode:

• Parker Palmer
• Let Your Life Speak
• Unknown Cosmic Time Machine
• Family Philanthropy Navigator
• Defense of Philanthropy
• Why Philanthropy Matters

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 Dr. Sharilyn Hale | Watermark Philanthropic Counsel: 

• Website: watermarkpc.com
• LinkedIn: Sharilyn Hale

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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 personal boundaries and shared vision within family businesses. Holly will introduce her philosophy of "walking beside" others with genuine curiosity rather than simply directing them, and preview how daily intentional actions can transform into powerful long-term outcomes. 

About Holly Simmons

Holly Simmons is a Family Enterprise Advisor (FEA™) who provides leadership coaching, facilitation, and training to growth-minded family businesses. She uses a strategic approach to align values and purpose, develop people and roles, and strengthen communication throughout the business and family system. 

Resources discussed in this episode:

• Conversational Intelligence
• The Knowledge Podcast by Shane Parrish

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 Holly Simmons | Golden Lasso Consulting: 

• Website: golden-lasso.com
• LinkedIn: Holly Simmons
• Email: [email protected]

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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 emphasizes the value of authentic trust, collaborative decision-making, and balancing "fair versus equal" approaches when integrating new family members. Listen to our latest episode to hear Emily's perspectives on fostering healthy family communication around wealth, establishing meaningful family traditions like regular dinners, and implementing practical solutions that honor both individual identities and shared family legacies.

About Emily Bouchard

Emily Bouchard is dedicated to unlocking the full potential of individuals and families, by guiding them through the complexities of wealth, relationships, and leadership. She is an author and speaker with over 20 years of experience coaching multigenerational families. As a fractional Chief Learning Officer, she designs personalized learning experiences that focus on lifelong growth, emotional intelligence, and financial acumen. She lives on a 10-acre ranch with 9 horses, where she facilitates transformative retreats.

Resources discussed in this episode:

• James Hughes
• Tamarind Learning
• The Thin Book of Trust
• Preparing Heirs
• Build an Enterprise Family to Last: Proven Strategies to Thrive Across Generations
• Jane Flanagan Research

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 Emily Bouchard | Bouchard Bespoke Consulting: 

• Website: EmilyBouchard.com
• Instagram: @emily4families
• X (formerly Twitter): @emily4families
• LinkedIn: Emily Bouchard

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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 emphasizes the importance of staying current with emerging technologies, building resilient management teams, and balancing risk management with growth opportunities. Listen to our latest episode to hear Gerard's insights on creating lasting business value, implementing strategic governance frameworks, and developing capital structures that help family enterprises thrive while securing their financial legacy.

About Gerard McInnis

Gerard McInnis is a Senior Partner with Kalos in the Valuation & Financial Modelling practice, contributing across the full transactions lifecycle with over 30 years of experience in business valuations, strategy, governance, and operations. As an active private company board Chair & Director, including Chair of the Board for Cashco Financial Services Inc. and a MacKay CEO Forum Chair, he remains immersed in current business challenges, risks, and opportunities while bringing valuable perspective from his previous role as a partner at a Big 4 accounting firm where he led their regional valuations practice and national power & utilities industry team.

Beyond his professional achievements, Gerard demonstrates strong commitment to community service, having recently chaired Finance & Risk committees for both the Alberta Ballet and Junior Achievement of Canada, and currently serving as a member of the Institute of Corporate Directors Calgary Chapter Executive. His comprehensive background spanning financial advisory, corporate governance, and community leadership positions him as a well-rounded business leader who effectively bridges technical expertise with strategic vision across multiple sectors.

Resources discussed in this episode:

• Kalos LLP I Transactions Diligence Advisory
• MacKay CEO Forums: CEO & Executive Peer Support
• Cashco Financial
• Institute of Corporate Directors

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 Gerard McInnis | Kalos Transactions Advisory: 

• Website: kalosllp.ca
• LinkedIn: Gerard McInnis
• Email: [email protected]
• Phone: (403) 470-9827

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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.

Throughout the conversation, Paul explores essential concepts like creating psychologically safe environments for authentic family discussions, why including all voices—even those of children as young as eight—can transform outcomes, and how "dreaming sessions" unlock possibilities rather than limitations. He emphasizes the importance of listening over talking, transparency over secrecy, and the profound difference between working "in" versus "on" your business. Listen to our latest episode to hear Paul's insights on facilitating meaningful family business meetings, balancing emotional intelligence with strategic thinking, and implementing succession approaches that honor both legacy and future potential.

About Paul Hood

A “recovering tax lawyer,” Paul Hood’s often quoted in publications that include Forbes magazine, USA TODAY, and The Wall Street Journal, and he’s been a frequent contributor to Leimberg Information Services, Inc. since its inception, Paul is a highly sought-after speaker and consultant because of his innate ability to see through the complexity and explain difficult and even boring subjects in understandable and entertaining language with his insightful and biting sense of humor, and he minces no words in doing so. Along the way, Paul’s been a father, husband, uncle, Godfather, lawyer, coach, mentor, trustee, member, director, president, partner, trust protector, director of planned giving, expert witness, agent, professor, judge, juror, respondent, and a defendant, and he uses his experience in these myriad roles to guide others. 

Resources discussed in this episode:

• The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It
• Purposeful Planning Institute
• Paul Hood Services

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 Paul Hood | Paul Hood Services & Purposeful Planning Institute: 

• Website: paulhoodservices.com
• LinkedIn: Paul Hood
• Email: [email protected]
• Phone: (504) 452-7574

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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.

Throughout the conversation, Matt delves into essential concepts like redefining success in the boardroom, the difference between technical expertise and genuine contribution, and why board composition goes far beyond professional credentials. He emphasizes the importance of treating connections as community rather than competition, creating shared understanding of decision-making processes, and balancing the complex relationship between management and governance. Listen to our latest episode to hear Matt's insights on navigating boardroom dynamics, fostering meaningful collaboration, and implementing governance approaches that help organizations thrive in times of change and complexity

About Matt Fullbrook

Matt Fullbrook, one of North America's most recognizable and respected corporate governance experts, has shared his 23 years of experience with over 300 boardrooms ranging from local nonprofits to global corporations. As the creator of the One Minute Governance podcast and Ground-Up Governance platform, he has developed an extensive library of practical insights for mastering boardroom challenges. Currently serving as an Executive in Residence at the University of Toronto's Rotman School of Management, where he has influenced governance practices for more than two decades, Matt previously directed the David & Sharon Johnston Centre for Corporate Governance Innovation and now serves as Academic Director of the Rotman/ICD program "Working Effectively With Your Board: A Program for Senior Executives.

Resources discussed in this episode:

• Ground Up Governance
• One Minute Governance
• Fullbrook Board Effectiveness

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 Matt Fullbrook | Rotman/ICD Board Dynamics Program: 

• Website: mattfullbrook.com
• LinkedIn: Matt Fullbrook
• Email: [email protected]

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