One of the most provocative ideas in my conversation with Nathan Chappell is that there may soon be no such thing as a “donor.” Nathan has spent more than two decades as a fundraiser and fundraising leader, and he’s become one of the clearest voices on AI in our field. This Keynote is also a milestone for us: it kicks off our first-ever Book Club, reading Nathan’s The Generosity Crisis, a book that has sat near my desk since I first heard him speak years ago at a Washburn McGoldrick conference.
What makes the conversation memorable is how candid Nathan is about his own past. He described an afternoon early in his career at UC San Diego, spent with a colleague talking about how to “build a better mousetrap” — and realizing only later that they had spent the whole time referring to donors as mice. That discomfort is the seed of the idea he is chasing now (and is the subject of an upcoming book), which he calls “N1 philanthropy”: a future with no donors and no prospects, just individuals, each with a unique and evolving connection to the causes they love.
Watch the full-length version (57 mins) on YouTube.
For those of us in advancement, alumni engagement, and communications, this episode raises questions worth sitting with. If precision medicine can match a treatment to a single patient’s genome, can our institutions finally stop segmenting people by averages and build a relationship with each person as an “N of one”? What happens to affinity in an attention economy where the average person brushes up against thousands of algorithms a day? And the question I keep returning to: what is AI actually for? Nathan’s answer surprised me. The point is not to do twenty percent more outreach — it is to give every fundraiser back a day a week for the human work no machine can do, keeping, as he puts it, the human at the helm. “We’re going to give them their joy back,” he says. Beneath all the technology, the reminder is a familiar one: people do not connect to efficiency or strategy. They connect to being known. That truth sits at the center of this conversation.
Big Themes This Week
The future Nathan calls “N1 philanthropy” treats every supporter as an individual an “N of one” rather than a member of a crude, averages-based segment, with predictive, generative, and agentic AI finally making that level of personalization possible at scale.
AI’s greatest value in advancement may not be efficiency or output, but the time it gives back — a “dividend of time” that frees fundraisers to do the deeply human work technology cannot.
Applying AI to a transactional or flawed fundraising practice only accelerates the problem; technology amplifies whatever culture and intent already exist.
The challenge facing institutions is fundamentally a relationship and connection problem, not a generosity problem, people remain generous when they feel genuinely known.
Keeping the “human at the helm” with people directing and accountable for how AI is used is what allows technology to deepen relationships rather than make engagement more transactional.
Team Discussion Questions
Where are we still segmenting donors and alumni by averages rather than treating them as individuals, and where could AI help us build a relationship with someone as an “N of one”?
If AI gave every member of our team a day a week back, what human work would we want them spending it on?
Which of our current tasks drain time and joy, and which are the “last mile” moments that actually build relationships?
Where is it essential that a human stays “at the helm” of any AI we adopt, and how do we keep AI-assisted outreach feeling authentic rather than automated?
Do our donors and alumni feel known by us, or processed by us and what makes our institution worth connecting with between asks?
