Sustainable Giving

How could giving circles reshape the future of philanthropy — and what might they unlock for your nonprofit?

In this episode of the Sustainable Giving podcast, Dave sits down with Emily Rasmussen, Founder & CEO of Grapevine and one of the leading voices in the modern collective giving movement. From her early life as a professional ballet dancer to her work in microfinance in rural India to now building the largest platform dedicated to giving circles, Emily brings a truly unique perspective to what generosity can look like when people do it together.

This conversation moves fast (in the best way!) as Dave and Emily dive into the resurgence of community-driven philanthropy, the psychology behind recurring generosity, and why giving circles just might be one of the biggest under-the-radar bright spots in the entire fundraising landscape.

If you care about connection, recurring giving, and the future of generosity… this one’s for you.

Key Topics They Cover:

1. Emily’s Unexpected Journey to Philanthropy

• From professional ballet to global arts leadership to microfinance in rural India

• How her early work in hyper-local, community-led financing became a blueprint for her later work in philanthropy

• The common thread: using creativity and community to unlock impact

  2. The Deep Roots of Collective Giving

• Giving circles: newer term, ancient concept

• Cultural traditions like tontines, susus, and self-help groups as early models

• Why doing good together is resurging now — and how it answers today’s loneliness + disconnection crisis

  3. What Giving Circles Actually Are (and Why They Matter)

• A clear, simple definition (100 people × $100 → $10,000 grant)

• How members nominate, vote, learn, and build lasting relationships

• “The Four C’s”: Community, Collective Resources, Collaboration, and Continuation

• Why giving circles create real belonging, not transactional giving

  4. The Powerful Connection Between Giving Circles & Sustainable Recurring Giving

• Stunning data:

• Only ~2% of new nonprofit donations are set to recur (GivingTuesday Data Commons)

• 50–80%+ of new giving-circle donations on Grapevine recur

• Why recurring giving is “baked in” to the giving circle model

• How collective models build trust, accountability, and long-term donor loyalty naturally

  5. How Nonprofit Leaders Can Tap Into the Giving Circle Movement

• How to find circles already giving in your region or cause area

• Why nonprofits should ask their donors whether they’re in one

• The rise of nonprofit-created giving circles + group-based donor communities

• How giving circles can supercharge board engagement, next-gen donors, and mid-level giving

  
  

  They Also Talk About:

• The role of trust, transparency, and “the five T’s” of generosity

• How Grapevine supports giving circles with infrastructure, community tools, and the global directory

• The surprising overlap between giving circles and workplace giving

• How companies are experimenting with employee-led giving circles

• Why generosity evolves with culture — and why that’s actually encouraging

So… what might happen if your community had a giving circle of its own? Or if you joined one yourself?

Watch or Listen:

Watch this episode now by clicking the video above, or by visiting Apple Podcasts or Spotify.

Key Resources:

• ⁠GivingTuesday Data & Research

• “Growing Giving” Research

• Explore Grapevine

• Connect with Emily on LinkedIn

• Grab Dave’s book, The Rise of Sustainable Giving

• Discover more episodes of the Sustainable Giving podcast

• Register for the Sustainable Giving Workshop

• Connect with Dave on LinkedIn
  

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Victoria.

How do you turn an emergency donor into a lifelong partner in impact?

When disaster strikes, generosity surges — but what happens when the headlines fade? In this episode of the Sustainable Giving podcast, host Dave Raley sits down with Vila-Sheree Watson, Vice President for Development & Membership at Bread for the World and author of the Bag Secured newsletter, to talk about transforming urgency into lasting generosity.

With nearly three decades of experience in humanitarian fundraising and advocacy, Vila-Sheree shares practical, hard-earned wisdom for any nonprofit leader navigating the space between crisis response and sustainable impact. This one’s equal parts strategy, storytelling, and inspiration — with plenty of laughs along the way.

Topics They Cover: 

• From Emergency to Endurance: How to move beyond one-time disaster gifts and design donor journeys that last long after the crisis fades.
  

• Turning Urgency into Habit: Vila-Sheree’s framework for helping donors connect their immediate compassion to long-term impact, and why “habit” is the secret ingredient to retention.
  

• Retention by Design, Not Luck: What it takes to intentionally plan for donor retention, including the digital tactics and messaging rhythms that keep people engaged.
  

• The “Sustainer-First” Mindset: Why leading with recurring giving (even during emergencies!) can double lifetime donor value, and how to make that ask feel natural.
  

• The Evolution of One-to-One Giving: What Vila-Sheree learned from years leading child sponsorship programs, and how to carry that human connection into today’s digital, subscription-style world.

Also in this episode, they talk about: 

• What Bread for the World teaches us about sustaining engagement in advocacy work

• Why donor acquisition should never be the first budget cut

• The importance of storytelling and dignity when representing program participants

• How organizations can prepare now for the “next” crisis

• The power of bringing humanity (and humor!) back into fundraising

What could your organization do today to make generosity last tomorrow?

Key Resources:

• Retaining Emergency Donors Before They Disappear

• Discover more about the work Vila-Sheree does at https://www.bread.org and https://bagsecured.substack.com/

• Get to know Vila-Sheree

• Get to know Dave Raley

• Discover more about the Sustainable Giving podcast⁠

• The Rise of Sustainable Giving Book⁠⁠⁠⁠

• The Sustainable Giving Workshop 2026

Special thanks to our team at Sustainable Giving: Abigail, Tom, Victoria and Kirsten.

What does it take to build an organization — and a life — that can go the distance?

In this episode of The Sustainable Giving podcast, host ⁠⁠Dave Raley sits down with Chris Free, Senior Director of Communications & Advancement at The Joshua Fund, to unpack what it really looks like to build endurance — both personally and organizationally.

From his beginnings as a filmmaker and storyteller to leading one of the most remarkable transformations in recurring giving we’ve seen, Chris shares the inside story of how The Joshua Fund grew from $5.3M to $18.6M in five years, with 47% of their revenue now coming from recurring donors.

They dig into the heart behind the data, exploring how storytelling, discipline, and faith intersect to create something truly sustainable. Whether you’re a nonprofit leader, fundraiser, or simply someone who cares about long-term impact, this conversation will inspire you to think differently about what it means to build something that lasts.

Key Topics They Discuss:

• The Power of Storytelling in Generosity How Chris’s early career as a filmmaker shaped his passion for purpose-driven storytelling,  and how that foundation now fuels The Joshua Fund’s mission and donor engagement.
  

• From Campaigns to Continuity The pivotal “aha moment” when Chris realized recurring giving wasn’t just a tactic. It was a mindset shift toward long-term sustainability.
  

• Building Systems that Sustain The real-life process of implementing sustainable giving practices, from adopting Fundraise Up to reworking donor experiences and automating communication flows.
  

• Transformation & Tangible Results How The Joshua Fund nearly doubled its recurring giving program and grew overall revenue 2.5x,  and what that stability means for impact, planning, and peace of mind.
  

• Endurance for the Long Run Parallels between marathon running and leadership: the discipline of consistency, learning to pace yourself, and the courage to keep going when you “hit the wall.”

  
  

Also in this episode, they talk about:

• Lessons from The Sustainable Giving Accelerator and how it reshaped The Joshua Fund’s culture.

• The importance of data over ego — why objective insights always win.

• How crisis moments can drive innovation in fundraising.

• The role of automation in scaling meaningful donor relationships.

• Why January (or September!) doesn’t have to be scary when half your revenue is already recurring.

What if your organization could move from reaction to rhythm; from chasing donations to cultivating generosity that lasts?

Additional Resources:

• ⁠The Rise of Sustainable Giving Book⁠
• ⁠The Sustainable Giving Workshop 2026

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Victoria.

What happens when the world’s biggest day of generosity meets the rise of the subscription economy?

In this special LIVE edition of The Sustainable Giving podcast, host ⁠Dave Raley⁠ is joined by ⁠Woodrow Rosenbaum⁠, Chief Data Officer at ⁠GivingTuesday⁠, for a deep and energizing conversation on how generosity is evolving, and how nonprofit leaders can turn one powerful day into lasting, sustainable impact.

Broadcast live on LinkedIn and made possible by ⁠CharityEngine⁠ — with a special word from Vice President of Marketing, ⁠Dave Martin⁠ — this episode unpacks what’s happening at the intersection of technology, culture, and generosity — and how organizations can build year-round giving strategies rooted in belonging, not burnout.

Key Topics They Covered:

1. The Future of Generosity: Woodrow shares the scale and scope of GivingTuesday’s global impact, and how the data shows generosity is more participatory, community-driven, and sustainable than ever before.

2. The Rise of Sustainable Giving: Dave and Woodrow explore the momentum behind recurring giving — noting that 12% of GivingTuesday donors last year became monthly givers — and what that tells us about the future of donor loyalty.

3. Four Insights to Grow Sustainable Giving This GivingTuesday: Dave outlines four proven strategies from the field:

- Start early, stay late: Treat GivingTuesday as a season, not a single day.

- Lead with recurring: Make monthly giving the hero of your campaign.

- Incentivize conversion: Use simple, delightful nudges like match offers or special perks.

- Leverage multiple channels: Align your message across email, social, direct mail, and events for a unified story.

4. Leveraging Shared Moments for Lasting Impact: The conversation turns to how shared cultural moments like GivingTuesday create belonging, spark participation, and, when leveraged well, lead to higher retention and deeper connection.

5. Launch of the Sustainable Giving Certification: Dave announces the new Sustainable Giving Certification, designed to recognize technology and service providers that enable recurring giving at scale. CharityEngine was recognized as the Founding Certified Partner for its leadership in sustainable giving technology.

Also in this episode, they talked about:

- How data insights from GivingTuesday reveal shifting donor behaviors.

- The link between technology, donor experience, and long-term retention.

- Practical steps for smaller nonprofits with limited tech resources.

- The importance of aligning providers and platforms with sustainable giving principles.

- Highlights from the Sustainable Giving Workshop and upcoming opportunities to engage.

What if your next GivingTuesday campaign didn’t end after 24 hours — but built a foundation for year-round generosity?

Get to Know the Presenters:⁠

- Learn more about Woodrow Rosenbaum⁠⁠

- Learn more about Dave Martin

⁠⁠- Learn more about Dave Raley⁠

Additional Resources:

• The Rise of Sustainable Giving Book
• The Sustainable Giving Workshop 2026
• Sustainable Giving Accelerator
• Recent Wave Report: “Growing Sustainable Giving This GivingTuesday”
• GivingTuesday Resources
• Growing Giving Research⁠
• Latest Research (GivingTuesday Data)
• CharityEngine Sticky Sustainers
• CharityEngine Sustainer Calculator

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Victoria.

What if the biggest opportunity in fundraising has been quietly waiting all along — hidden in plain sight?

In this episode of the Sustainable Giving podcast, host Dave Raley chats with Erica Waasdorp, President of A Direct Solution, longtime champion of monthly giving, and self-proclaimed “Philanthropyholic.” From her early career at Reader’s Digest in Amsterdam to 30+ years helping nonprofits grow recurring giving programs around the world, Erica has seen it all, and she’s here to share the lessons that last.

Together, Dave and Erica dive into what’s changed (and what hasn’t) in the world of recurring giving, from the first direct-debit donors in Europe to the digital subscription era today. They unpack the tactics, mindset, and global insights that help organizations build sustainable, recession-resistant revenue, and what the next generation of fundraisers needs to know.

Whether you’re just getting started with recurring giving or looking to take your program to the next level, this conversation is packed with wisdom, wit, and plenty of inspiration.

Key Topics They Cover:

1. The Evolution of Recurring Giving: How monthly giving has transformed from mail and phone to digital-first—and why some organizations are still playing catch-up.
   

2. The Commitment Gap: Why many nonprofits still treat monthly giving as an afterthought—and how shifting from a “single-gift mindset” to a sustainability mindset changes everything.
   

3. Tactics That Still Work: Erica’s go-to strategies, from adding a simple “Give Monthly” button to leveraging donor testimonials, direct mail, and even the humble thank-you letter.
   

4. Lessons from Around the World: What generosity looks like in different cultures—and why human behavior (and the desire to help) is far more universal than we think.
   

5. The Next Generation of Sustainable Fundraisers: What today’s leaders can do to invest in recurring giving, mentor the next wave, and build long-term programs that inspire both donors and staff.

   
   

Also in this episode, they talk about: 

• How Dutch directness inspired A Direct Solution, and why honesty matters in fundraising

• Why smaller monthly gifts can lead to major legacy gifts later

• The underrated power of direct mail and phone calls in a digital world

• What European fundraisers got right decades ago, and what the U.S. can learn

• The simple truth behind “Just start—and keep going”

  
  

If recurring giving is the key to sustainability, what’s stopping your organization from planting that first seed today?

Additional Resources:

• Register for the 2026 Sustainable Giving Workshop.

• Pick up a copy of Dave's book, "⁠The Rise of Sustainable Giving⁠."

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Victoria.

What does it take to shift an entire organization to a “sustainer-first” mindset — and keep donors engaged for the long haul?

In this episode of the Sustainable Giving podcast, host Dave Raley sits down with Sofia Machado Lemus, Director of Multi-Channel Fundraising at Operation Smile. From her early work with underserved communities in Guatemala to leading multicultural and sustainer fundraising efforts today, Sofia brings a global perspective, practical insights, and a deep passion for helping donors make a lasting impact.

Together, Dave and Sofia explore the real-life challenges and opportunities of building a strong recurring giving program, one that not only drives long-term stability but also reflects the values of diverse donor communities.

Key Topics They Cover:

1. The power of recurring giving at Operation Smile
   How sustainers now make up nearly a third of annual revenue, and why that stability matters for global programs.

2. Shifting to a sustainer-first mindset
   The internal challenges, testing strategies, and leadership conversations that made this cultural and operational shift possible.

3. The role of Hispanic donors in sustaining growth
   Why Spanish-speaking donors are especially loyal, how cultural values shape retention, and what other nonprofits can learn.

4. Leadership buy-in through small wins
   The importance of testing, proving ROI, and showing long-term donor value to get C-suite support.

5. Innovation through SMS and mobile engagement
   How text messaging is outperforming email for sustainer acquisition, and where Sofia sees future opportunities.

   
   

   Also in this episode, they talk about:

• Lessons learned from testing sustainer-first campaigns during year-end giving.

• The balance between one-time gifts and long-term recurring support.

• How gratitude and consistent communication drive donor retention.

• Why multicultural fundraising is not optional for the future.

  
  

What role will sustainers play in the next decade of nonprofit growth, and are we doing enough today to prepare?

Key Resources:

• Discover more about the work Sofia does at Operation Smile and Sonrisas Nuevas.

• Get to know Sofia.

• Get to know Dave⁠.

• Register for the 2026 Sustainable Giving Workshop.

• Pick up a copy of Dave's book, "⁠The Rise of Sustainable Giving⁠."

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Victoria.

What if your donors felt just as essential to your mission as the people you serve?

In this episode of the Sustainable Giving podcast, host Dave Raley sits down with Tina Hudgins, a seasoned fundraiser, consultant, and educator who has spent her career helping organizations build donor-centric cultures that spark lasting generosity. From her days pioneering sustainer programs at International Justice Mission to her current work with Philanthropy and Fundraising of North America (PFNA), Tina brings a wealth of insight, energy, and heart to the conversation.

Together, Dave and Tina explore how recurring giving isn’t just a strategy. It’s a movement. They talk about the power of sustainer programs to weather economic storms, the lessons from bold experiments in event-based giving, and how nonprofits can reframe their culture to honor donors as much as beneficiaries.

Here are the top 5 takeaways from this episode:

• Sustainer Giving as “C²R²”: Tina’s mantra — cash consistent, recession resistant — and how monthly giving creates stability and freedom for planning and innovation.
  

• Event-Based Acquisition in Action: The powerful story of the IF:Gathering event, where IJM invited thousands of women to become Freedom Partners through a deeply integrated, mission-driven experience.
  

• The Freedom Partner Journey: How IJM cultivated monthly donors — from $5 givers to $5,000/month partners — through storytelling, access, and intentional community.
  

• Donor-Centric Culture: Why nonprofits must treat donors as equally important as beneficiaries, and how this shift transforms revenue, retention, and relationships.
  

• Budgets & Boldness: Tina’s framework for acquisition, retention, and innovation budgets, and why learning itself should be considered a KPI.

Plus, a few more gems you won’t want to miss:

• Why asking major donors for recurring gifts actually deepens commitment (without reducing larger gifts).
  

• How to make events more than “one-time fundraising moments” by embedding them in your mission story.
  

• What it looks like when every staff member is equipped to tell your organization’s story, even in a 14-floor elevator ride.
  

• Why cultural transformation is the secret to long-term growth (200–1000% revenue gains over time!).
  

So, how can your organization start seeing itself through the eyes of your donors?

Key Resources:

• Learn more about the work that Tina does.
• Get to know Tina.
• Get to know Dave.
• Pick up a copy of Dave's book, "The Rise of Sustainable Giving."

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Victoria.

What if the way we’ve been doing fundraising all along is actually setting nonprofits up to fail?

In this episode of the Sustainable Giving podcast, host Dave Raley sits down with Author, Keynote Speaker, and Nonprofit Advisor Lisa Greer, a major donor with a front-row seat to the best (and worst) of fundraising. Lisa brings candor, humor, and wisdom as she unpacks why so much of fundraising feels outdated and what it takes to build organizations that truly last.

From awkward million-dollar donation calls to why recurring giving is still the nonprofit world’s best-kept secret, Lisa shares real stories and practical insights that will challenge how you think about generosity, boards, and building trust with donors.

Top 5 Topics We Dive Into:

1. Why most fundraising is broken: Antiquated, inefficient, and ultimately unsustainable practices that nonprofits keep repeating.

2. The nonprofit starvation cycle: How underfunding operations creates a vicious cycle that drives talent away and keeps organizations constantly on the edge.

3. Boards as allies or obstacles: Why boards so often block progress, and how leaders can shift board culture to be a true force for good.

4. The power of recurring giving: Why donors of all levels (even major donors!) are embracing recurring gifts and how it changes the game for sustainability.

5. The donor’s perspective: What fundraisers often get wrong about donors (hint: we’re people, not revenue streams!) and how to build authentic, long-term relationships.

Plus, We Touch On:

- The story behind Lisa’s first major gifts, and the shocking responses she got.

- Why recurring donors aren’t “downgrades” (and are often your most loyal supporters).

- Creative ways to keep recurring donors engaged and connected.

- The role of transparency in building trust between donors and organizations.

- Why overhead shouldn’t be a dirty word. It’s actually the foundation for impact.

What would change if your nonprofit started treating donors like partners instead of pocketbooks?

Key Resources:

- Learn more about Lisa Greer.

- Subscribe to Lisa’s Philanthropy 541 Substack to receive free weekly tips.

- Pick up a copy of Dave’s book, "The Rise of Sustainable Giving."

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Victoria.

What if the best glimpse into the future of fundraising isn’t found in trend reports or tech forecasts, but in the story of someone who’s already lived it?

In this episode of the Sustainable Giving podcast, host Dave Raley sits down with Ken Burnett—legendary fundraiser, author of Relationship Fundraising, and one of the earliest champions of “regular giving.”

Nearly 50 years ago, Ken stood where we are now, facing questions about how to engage donors for the long haul. What followed was a movement that reshaped generosity across the UK and Europe—and offers us a powerful preview of what’s possible for the future of giving everywhere.

From ActionAid’s early embrace of monthly donations to Greenpeace’s global regular giving campaigns, Ken shares lessons from the past that point straight toward the future of sustainable generosity. It’s a fun, thought-provoking conversation filled with wisdom, wit, and practical insights for every fundraiser who wants to build something that lasts.

Key Topics They Cover:

• The origins of regular giving in the UK – How ActionAid’s embrace of monthly giving in the late ‘70s turned a small startup into one of Britain’s top charities.
  

• UK vs. North America giving culture – Why regular giving is the norm “across the pond” and what’s holding the North American sector back.
  

• The power of direct debit (EFT) – Why it beats credit cards for retention, and how inertia can actually be a fundraiser’s best friend.
  

• From retention to legacy – How loyalty leads to bequests, and why focusing on the donor experience is the fastest path to long-term impact.
  

• The leadership gap – Why short-term thinking and underinvestment in fundraisers is costing the sector dearly, and how to change it.
  

Also in This Episode, They Talk About:

• Stories of face-to-face street fundraising that had people lining up to give.
  

• How to delight donors so much they never want to leave.
  

• The surprising mental and physical health benefits of being a donor.
  

• Discover more about Ken’s work

• Register for the Sustainable Giving Workshop

• Pick up a copy of Dave’s book, “The Rise of Sustainable Giving”

  
  

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Grace.

What if the stories your donors need to hear aren’t the ones you’re telling, but the ones your community is waiting to share?

In this episode of the Sustainable Giving podcast, host Dave Raley sits down with Natalie Monroe, Manager of Community Engagement at MemoryFox. Natalie brings a unique lens to the conversation, blending a background in agriculture and wine with a deep passion for visual storytelling and nonprofit impact.

Together, they explore how ethical, community-generated storytelling can foster deeper connections with donors and build the foundation for recurring, sustainable giving.

Natalie shares her journey from working with veterans-turned-farmers to helping nonprofits collect and share powerful, authentic stories using MemoryFox. She unpacks why it’s no longer enough to tell polished marketing stories about your mission, and how nonprofits can shift toward telling stories with and by their communities.

Key Takeaways Include:

1. From Wine to Veterans to Video: Natalie’s unconventional path led her from the wine industry to writing veteran stories at Farmer Veteran Coalition, then discovering the power of letting people tell their own stories through video and visuals.

2. What Is Ethical Storytelling, and Why It Matters: Sharing someone’s story isn’t just a marketing tactic. It’s a responsibility. Natalie breaks down what it means to tell stories ethically, with dignity and authenticity.

3. User-Generated Content Builds Donor Trust: Donors don’t just want stories. They want real ones. From selfie videos to short testimonials, authentic user-generated content (UGC) builds social proof, credibility, and emotional connection.

4. Storytelling as a Bridge to Sustainable Giving: Natalie shares how organizations are using MemoryFox to deepen engagement with recurring donors, particularly by spotlighting the voices of those directly impacted.

5. The Hidden Power of Asking the Right Questions: Sometimes people don’t know they have a story until you invite them to share it. Natalie reflects on how the simple act of asking can unlock powerful moments of connection and generosity.

Also in this episode, you’ll hear:

- How visual storytelling helped a Kentucky nonprofit turn literacy stats into donor empathy

- The difference between “Star Wars stories” and “Springsteen stories”

- Why small, bite-sized gifts feel more accessible and sustainable to today’s donors

- How storytelling can educate, not just fundraise

- The surprising impact of letting donors share why they give right after making a gift- Why nonprofits should move from polished campaigns to real, community-driven narratives

- How kids can learn generosity early through videos, stories, and sustainable giving habits

- How would your donor strategy shift if your community’s stories — not your marketing team — became your most powerful fundraising asset?

Additional Links:

- Get to know Natalie: https://www.linkedin.com/in/nataliesmonroe

- Discover more about Memory Fox: www.memoryfox.io

- Get to know Dave: https://www.linkedin.com/in/draley

- Discover more: sustainablegiving.org/podcast

- Register for the Sustainable Giving Workshop: https://www.imago.consulting/workshop

- Grab Dave’s Book: The Rise of Sustainable Giving: https://sustainablegiving.org

Special thanks to our team at Sustainable Giving: Abigail, Tom, Kirsten, and Grace.