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