A Crisis in Generosity? AI, Recurring Giving, and the Future of Fundraising

Written By Dave Raley

Welcome to Episode 1 of the ⁠Sustainable Giving⁠ podcast, where we’re shining a light on how generosity works in a world increasingly shaped by the subscription economy.

Hosted by ⁠Dave Raley⁠—speaker, consultant, and best-selling author of ⁠The Rise of Sustainable Giving⁠—this show explores the trends, tools, and tactics powering the future of nonprofit fundraising through recurring giving.

In this episode, Dave is joined by ⁠Nathan Chappell⁠—Chief AI Officer at ⁠Virtuous⁠ and co-author of ⁠The Generosity Crisis⁠—to tackle the tough questions facing generosity today.

Nerding out together over this up-and-coming trend in the nonprofit space, Dave and Nathan dive into the state of generosity in North America, explore how nonprofits can build more sustainable giving models, and discuss the massive implications of artificial intelligence for the future of philanthropy.

Key Topics They Cover:

1. Why This Podcast, Why Now

  • What led Dave to start the Sustainable Giving Podcast

  • Dave’s and Nathan’s shared vision to spread generosity through innovation

  • Candid reflections on the purpose and personal cost of writing a book

2. The Generosity Crisis

  • What the data tells us about the state of giving in the U.S.

  • The shift from broad-based giving to fewer, larger donors

  • Why generosity is declining—and what that means for the future

3. Recurring Giving & The Subscription Economy

  • How monthly giving is outperforming traditional donor retention

  • Why nonprofit leaders should double down on predictable revenue

  • What nonprofits can learn from Netflix, Spotify, and subscription culture

4. AI and the Future of Generosity

  • How artificial intelligence can personalize donor experiences at scale

  • The myth that innovation and ethics are mutually exclusive

  • Building AI tools that center the donor, not just the data

5. Inspiration for a Generous Future

  • Why Dave and Nathan are hopeful about the future

  • Stories of generosity from childhood and career

  • What it will take to inspire a new generation of givers

Also in this episode, you’ll hear: 

  • How fewer individuals are giving to charity, and why that matters

  • Why innovation is mission-critical, not optional

  • The rise of AI fluency in nonprofit leadership

  • Practical ways to start or improve a recurring giving program

  • The joy of generosity—from French macarons to freedom fighters

Watch or Listen:

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

Dave Raley
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