We Are For Good Podcast - Episode 619: "Hold Fast: The Heart of Generosity: Trust, Belonging, and Community" featuring Holly Lee

Release Date: May 12, 2025

In Episode 619 of the We Are For Good Podcast, hosts Jon McCoy, CFRE, and Becky Endicott, CFRE, delve deep into the essence of generosity within the nonprofit sector. Featuring returning guest Holly Lee, a renowned philanthropy innovator and author of The Big We, the episode explores the foundational pillars of trust, belonging, and community in fostering impactful and resilient nonprofit organizations.

1. Introduction: Embracing the Theme of "Holding Fast" (00:01 - 02:34)

John and Becky set the stage by highlighting the increasing challenges nonprofits face, emphasizing the need to "hold fast" to their missions amidst rapid changes and uncertainties. They introduce Holly Lee, celebrating her contributions as a disruptor in philanthropy and a community builder.

Becky (00:34): "We're nonprofit professionals, philanthropists, world changers, and rabid fans who are striving to bring a little more goodness into the world."

2. The Essence of Generosity: Relationships and Trust (03:23 - 05:05)

Holly Lee articulates that the core of generosity lies in building and nurturing relationships. She draws an analogy between physical constipation and the stagnation in philanthropy caused by overcomplicating generosity through professionalization.

Holly Lee (04:45): "We can overcomplicate generosity, especially when we professionalize fundraising and philanthropy. It can sometimes constipate the gears. So one of the things in my book is just like, come on, let's get it flowing."

Key Points:

• Generosity is driven by trust and relationships.
• Simplifying the act of giving can foster more authentic and fluid generosity.
• Building genuine connections leads to sustained and meaningful philanthropic engagements.

3. Navigating Donor Relationships: Short-Term Needs vs. Long-Term Trust (05:58 - 09:30)

John raises a critical issue: how nonprofits can balance immediate funding needs with the cultivation of long-term trust-based relationships with donors. Holly emphasizes the pivotal role of individual donors, especially in times when large institutional philanthropies face increasing scrutiny and challenges.

Holly Lee (07:15): "Individuals give for the long haul much more than foundations can. You can put organizations into your will, support them consistently over decades."

Key Points:

• Individual donors offer agility and sustained support that large foundations may not.
• Building long-term relationships with individual donors is essential for enduring impact.
• Nonprofits should prioritize cultivating trust over mere financial transactions.

4. The Shift to Collective and Inclusive Philanthropy (09:30 - 14:02)

The conversation transitions to the future of philanthropy, which Holly perceives as increasingly collaborative, collective, and inclusive. She critiques the traditional model dominated by "Big Phil"—heroic, individualistic philanthropists—and advocates for a more democratic and community-centered approach.

Holly Lee (10:45): "Our democratic system in America works only when its citizens care enough to get educated and join forces to do good in our community."

Key Points:

• Moving away from reliance on mega-donors to collective giving models.
• Emphasizing inclusivity and diverse voices in philanthropic efforts.
• Building community-based philanthropy enhances democratic engagement and societal resilience.

5. Practical Strategies for Diversifying Fundraising (16:10 - 22:30)

Becky prompts Holly to share actionable insights on how fundraisers can begin diversifying their donor base without overwhelming their teams. Holly outlines a two-part approach:

1. Assessing the "Why" and Building a Baseline:

   • Understand why diversification is essential for your organization.
   • Conduct an audit of your current donor demographics to establish a baseline.

2. Engaging and Building Relationships:

   • Initiate genuine conversations with a diverse range of donors.
   • Focus on listening and understanding donors' values and motivations.

Holly Lee (16:36): "Ask why is it important to diversify your fundraising base... then you can start building on a real ground."

Key Points:

• Start with Self-Reflection: Clarify the motivations and goals behind diversification.
• Data-Driven Approach: Collect and analyze data on current donor demographics.
• Genuine Engagement: Prioritize building authentic relationships over transactional interactions.

6. Empowering Grassroots Organizations (22:30 - 28:14)

Holly shares anecdotes illustrating the power of grassroots movements and collective action. She emphasizes that small, community-driven efforts can lead to significant impact when individuals organize and collaborate around shared values.

Holly Lee (26:05): "Individuals organized into groups are powerful. People are looking for community right now... the cure for loneliness is belonging."

Key Points:

• Collective Action: Small groups can drive substantial change through unified efforts.
• Community Building: Addressing social issues by fostering a sense of belonging and collective purpose.
• Low-Burden Initiatives: Encourage simple, community-centric activities like movie screenings or group discussions to build connections and support.

7. Homework and Practical Exercises (29:25 - 32:13)

Holly provides listeners with practical "homework" to implement the discussed strategies:

1. Read Dr. Vivek Murthy's Letter: Understanding the impact of loneliness and the importance of community.
2. Engage with Donors: Conduct deep, meaningful conversations with at least five supporters to understand their motivations and values.
3. Build Connections: Create opportunities for community members to connect and collaborate around shared interests and causes.

Holly Lee (31:00): "What brings you joy? The first question in our interview protocol is all about family and... the people and the culture and what brings you to this work."

Key Points:

• Deep Engagement: Shift focus from immediate fundraising to building meaningful relationships.
• Storytelling: Encourage donors to share personal stories to strengthen bonds and mutual understanding.
• Community Actions: Facilitate group activities that promote collaboration and collective impact.

8. Concluding Insights and One Good Thing (32:13 - 38:45)

As the episode wraps up, Holly shares inspiring examples of collective action, such as mothers raising over a million dollars through giving circles to support political change. She underscores the transformative power of organized groups aligned around shared values.

Holly Lee (33:50): "The power of individuals who come together in groups to do amazing things... they are powerful."

Becky reinforces the importance of humanity and simple acts of kindness in fostering community and impact.

Becky (33:10): "There are lessons for this moment and what it means to be human because we have seemed to lost some of our humanity in the way we walk through this earth. Let's be that humanity."

9. Final Thoughts and Promotion (38:45 - 39:05)

The hosts encourage listeners to engage with Holly Lee’s book The Big We and to start building or joining community groups that foster trust and collective action.

Holly Lee (38:45): "Invite me to your book group. Read it in a book group and LinkedIn me, you know, chat me on LinkedIn."

Key Takeaways:

1. Relationships Are Central: Genuine, trust-based relationships form the bedrock of effective generosity and philanthropy.
2. Shift to Collective Giving: Moving away from reliance on large, individual donors to a more inclusive, community-driven approach enhances sustainability and impact.
3. Practical Diversification: Nonprofits should methodically assess and engage with diverse donor bases through intentional strategies and authentic conversations.
4. Empower Grassroots Efforts: Small, organized groups can drive significant change by leveraging collective strengths and shared values.
5. Foster Belonging: Addressing social issues requires building communities where individuals feel a sense of belonging and connection.

This episode serves as a compelling guide for nonprofit professionals seeking to navigate the complexities of modern philanthropy. By emphasizing trust, community, and collective action, Holly Lee and the We Are For Good team provide actionable insights to inspire and empower organizations to make a lasting impact.

For more resources and to join the We Are For Good community, visit www.weareforgood.com.