Why 80% of Donors Under 40 Never Give Twice — And How AI Can Help Fix It | DX Sessions Seattle

Four out of five donors under 40 never give to the same nonprofit twice — compared to roughly half of donors over 65. In this DX Sessions Seattle keynote, Anton Lipkanou, President and COO of Delve Deeper, breaks down why that gap exists and how AI can close it without producing generic "AI slop." Anton opens with the personal story that shaped his career — growing up in Belarus, discovering his father had been living a double life, and how that experience pushed him toward building authentic, data-driven work in marketing. From there, he lays out a practical framework nonprofits can use today to grow sustainer revenue with AI as the tool, not the strategy. Key takeaways from this session: The nonprofit "giving pyramid" is becoming unstable: fewer donors are giving more, concentrating risk in a shrinking base of major donors 4 out of 5 donors under 40 don't donate to the same organization twice, per the USA Giving report, versus about half of donors over 65 Delve Deeper's "three-and-a-half-legged stool" framework identifies misaligned media, lack of personalization, poor segmentation, and siloed data as the real blockers to sustainer growth — not AI itself AI's real strength for donor data is twofold: extrapolating small data samples across an entire donor file, and analyzing unstructured data like call recordings, interviews, and social posts DonorGPT: a concept for an AI chatbot that interviews donors to build motivation-based personas, tested with real donors from Habitat for Humanity A Google Ads case study with World Food Programme shows how AI caught a major gap between stated sustainer goals and actual ad messaging Why automated bidding tools like Performance Max and Advantage+ can push above-average marketers toward average returns, and what to do instead A real case study on how travel brand Omni Hotels solved cross-property attribution for two competing properties less than a mile apart An explanation of MCP (Model Context Protocol) and how it lets tools like Claude connect directly to ad platforms and CRMs This session is part of DX Sessions Seattle, a Fundraise Up event bringing together nonprofit fundraising and development leaders to share what's actually working in donor acquisition, retention, and personalization at scale. 00:00 A Personal Story: My Father's Secret Double Life 04:19 How That Loss Led Anton to Marketing and Founding Delve Deeper 05:24 The Broken Giving Pyramid Nonprofits Face in 2025 06:57 Three Dirty Secrets About AI in Fundraising 08:50 The Three-and-a-Half-Legged Stool Behind Sustainer Growth 10:09 Why 80% of Donors Under 40 Never Give Again 12:13 Meet Margaret: A Real Donor Persona Exercise 14:51 Beyond RFV Data: What We Actually Need to Know About Donors 17:36 Habitat for Humanity and the Political Affiliation Myth 17:58 Introducing DonorGPT: Interviewing Donors and Uncovering Personas With AI 24:06 Turning Years of Email and Mail Data Into AI-Powered Segmentation 28:59 Fixing Misaligned Media Spend and Finding Your Next Sustainer's True Cost 32:44 Why Automated Ad Tools Like PMax and Advantage+ Backfired 36:12 Case Study: How Omni Hotels Solved Cross-Property Attribution 38:00 AI as an Army of Interns That Still Needs Direction 40:47 What Is MCP? Connecting Claude to Your CRM and Ad Accounts 44:28 Closing: Using AI to Make Every Donor Feel Seen Learn more about Fundraise Up: https://fundraiseup.com