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: beaconfamilyoffice@assante.com

Contact Dr. Sharilyn Hale | Watermark Philanthropic Counsel:

• Website: www.watermarkpc.com
• LinkedIn: https://www.linkedin.com/in/sharilynhale/

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: beaconfamilyoffice@assante.com

Contact Holly Simmons | Golden Lasso Consulting:

• Website: golden-lasso.com
• LinkedIn: Holly Simmons
• Email: holly@golden-lasso.com

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: beaconfamilyoffice@assante.com

Contact Emily Bouchard | Bouchard Bespoke Consulting:

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

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: beaconfamilyoffice@assante.com

Contact Gerard McInnis | Kalos Transactions Advisory:

• Website: kalosllp.ca
• LinkedIn: Gerard McInnis
• Email: gmcinnis@kalosllp.ca
• Phone: (403) 470-9827

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: beaconfamilyoffice@assante.com

Contact Paul Hood | Paul Hood Services & Purposeful Planning Institute:

• Website: paulhoodservices.com
• LinkedIn: Paul Hood
• Email: paul@paulhoodservics.com
• Phone: (504) 452-7574

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: beaconfamilyoffice@assante.com

Contact Matt Fullbrook | Rotman/ICD Board Dynamics Program:

• Website: mattfullbrook.com
• LinkedIn: Matt Fullbrook
• Email: matt@boardeffectiveness.ca

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.

Throughout the conversation, Dave illuminates the delicate balance between protecting and empowering rising generations in family enterprises. He explores compelling perspectives on creating environments where future owners can authentically experience both success and failure, while emphasizing how transparency and shared challenges strengthen family bonds. His framework for developing true owners, not merely inheritors, provides valuable insights for families seeking to build enduring legacies that preserve relationships while fostering business resilience across generations.

About Dave Specht

Dave Specht is the Director of the Drucker School Global Family Business Institute. His professional mission is to Preserve Families and Perpetuate Businesses. He is the author of, “The Family Business Whisperer” and thought leader on topics surrounding generational continuity of family-owned businesses and family wealth. Prior to his current role, he trained 2,500 top advisors/bankers at a Private Bank on family dynamics and generational wealth issues. Prior to his work at the bank, he founded Advising Generations, a consulting rm and established the Family Business Management program at the University of Nebraska. Dave lives in Washington state with his wife and 6 children.

Resources discussed in this episode:

• The Family Business Whisperer
• James Hughes Foundation
• Dennis T. Jaffe

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

• Website: BeaconFamilyOffice.com
• LinkedIn: Cory Gagnon
• LinkedIn: Beacon Family Office
• Email: beaconfamilyoffice@assante.com

Contact Dave Specht | The Drucker School of Management:

• LinkedIn: Dave Specht
• Email: david.specht@cgu.edu

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.

Throughout the conversation, Doug delves into essential concepts like the HERO framework (Hope, Efficacy, Resilience, and Optimism) and practical approaches to family storytelling and legacy preservation. He emphasizes the importance of creating safe spaces for authentic communication, developing leadership skills in rising generations, and balancing family privacy with meaningful connection. Listen to our latest episode to hear Doug's insights on building psychological capital, fostering intergenerational dialogue, and implementing strategies that help families flourish while preserving their legacy.

About Doug Gray

Doug Gray, Ph.D., is the Founder and CEO of Action Learning Associates, LLC and co-Founder of Assess Next Gen, LLC, bringing over 25 years of executive coaching and leadership consulting experience to family enterprises and organizations. With a doctorate in Leadership and Professional Practice from Trevecca Nazarene University, Doug has established himself as a pioneer in developing psychological capital (PsyCap) within family businesses and nurturing next-generation leadership talent. His innovative HERO framework (Hope, Efficacy, Resilience, and Optimism) has become instrumental in helping families navigate complex wealth and legacy dynamics.

As a champion for leadership excellence and intergenerational understanding, Doug's expertise spans across healthcare, finance, manufacturing, and education sectors. His approach combines rigorous academic research with practical, actionable strategies that help families create safe spaces for authentic communication and legacy preservation. Through his work at Action Learning Associates and Assess Next Gen, Doug remains dedicated to helping leaders and teams achieve measurable business outcomes while fostering the development of future organizational leaders.

Resources discussed in this episode:

• The Five Capitals: Wealth as Well-being
• The Success Playbook for Next Gen Family Business Leaders

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

• Website: BeaconFamilyOffice.com
• LinkedIn: Cory Gagnon
• LinkedIn: Beacon Family Office
• Email: beaconfamilyoffice@assante.com

Contact Doug Gray | Action Learning Associates, LLC

Websites

• NextGenPeerGroups.com
• AssessNextGen.com
• Action-Learning.com
• books2read.com/NEXTGEN
  
• LinkedIn: Doug Gray
• Substack: grayd.substack.com
• Twitter/X: @ALACoaching
• Email: doug@action-learning.com