Let's Talk Fundraising

Keith just got back from AFP ICON in San Diego, and this episode is his honest debrief. From a late-night reunion dinner with his AFP Leadership Institute cohort (including a practical tip for fundraisers who travel for donor visits) to leading one of the conference's opening sessions on making conferences actually matter in your organization, Keith shares what stuck with him and why. He also shares what he saw in the AI sessions, and he's not pulling punches. A lot of what's being sold as cu...

You've had the donor meeting. It went fine. The conversation flowed, the donor was warm, you covered a lot of ground. And now you're sitting in the parking lot wondering if any of it actually moved the relationship forward. That quiet uncertainty after a visit almost always traces back to the same problem: walking in with a direction instead of a strategy. In this episode, I share the one preparation habit that changed how I lead every donor conversation, and why I wish someone had made it th...

For months, I was doing everything I thought I was supposed to do as a major gift officer. I was reaching out. I was having meetings. I was putting in the work. But nothing was closing. And the hardest part wasn’t the lack of results. It was not knowing if what I was doing was actually working. In this episode, I’m sharing the moment that changed everything, and how I went from second-guessing my work to having complete clarity and confidence in what I was doing. You’ll hear how I: Moved from...

There’s a moment most fundraisers don’t talk about. The one where you know what needs to happen next… but you’re still trying to get everything lined up before you move. More research. More preparation. More time to “get it right.” And it feels responsible. But over time, that moment starts to cost you something. In this episode, I share a real story from early in my career when I got stuck in that exact place… and what I realized just before it was too late. We’ll walk through: Where “analys...

Most of us came into this work to build relationships. But too often our days get buried under contact reports, prospect research, and messy systems that keep us tied to a desk. In this episode, we explore a simple idea: what if AI could handle some of the repetitive administrative work so fundraisers could focus more energy on donor relationships? You’ll hear the story behind a set of practical AI workflows that began as small experiments and grew into a framework that supports the entire ma...

Looking for a unicorn hire who “just gets it” on day one? We’ve all been there—and it rarely works. To celebrate fifty episodes, we pull back the curtain on what truly drives consistent donor results: intentional onboarding that blends benchmarks with belief, practice with coaching, and culture with clarity. We map four levels of onboarding—from isolation and functional quick tours to benchmarked ramp-ups and full alignment—and show how each step changes employee confidence and donor outcomes...

This Groundhog Day episode is a personal announcement and a fundraiser’s roadmap for change. After fifteen years in nonprofit leadership, I’m stepping away from a role I loved—not because something was wrong, but because something bigger was calling. What began as one reluctant conference session turned into a growing invitation to speak, teach, and help nonprofits navigate the future of fundraising, AI, and trust. In this episode, I share the full story behind my pivot, the fear and grief th...

Remember when donor newsletters read like dissertations and first-time givers needed a decoder ring? We take a clear-eyed look at how AI has quietly raised the baseline for clarity in fundraising and communications—and why that shift changes expectations, not the essence of our work. The conversation moves past hype and eye-rolls to focus on what’s actually changing: standards, roles, and the line between acceptable and excellent. We unpack the two most common reactions to AI—quiet fear abou...

Free Gift 🎁 Big Goals Worksheet If goal setting feels like a test you’re always failing, this conversation offers a calmer path. We pull apart the myths that keep fundraisers stuck—outcome-only targets, motivation as strategy, and the idea that discipline alone drives results—and replace them with a research-backed approach that actually holds the messiness of real work. You’ll hear how to separate what you want to change from what you can control, design if-then responses for predictable obs...

Every fundraiser knows the weight of unwritten thank you notes—that pile on your desk, the rushed emails sent just to clear your to-do list, the nagging guilt when your gratitude doesn't sound quite right. You're not alone in this struggle. I share a personal story about working at an organization where the CEO expected impossible levels of personalization in donor thank yous. They wanted handwritten notes with intimate details for hundreds of weekly donors—references to tennis games, grocer...

Ever wish you could clone yourself on Monday morning? In this mini-episode, I’ll show you how to turn your favorite prompts into something far more powerful: CustomGPTs—personalized AI assistants trained on your best fundraising language and strategy. You’ll learn how to build three fundraisers’ essentials: • An Email Writer that drafts thank-you notes, follow-ups, and appeals • A Board Report Builder that turns CRM data into clear, mission-driven insights • A Prospect Profile Generator that ...

Every nonprofit leader knows the struggle: that moment when your calendar reminder pops up – "Board packet due tonight." You export columns of numbers from your CRM, spend hours wrestling with spreadsheets, triple-checking figures, and aligning columns. All this effort, only to watch board members' eyes glaze over two pages into your meticulously crafted report. What if there's a better way? A method that transforms dense data into clear, compelling narratives that your board not only unders...

Every fundraiser faces the same dilemma: we need efficiency, but we can't sacrifice accuracy. When that major donor asks for one critical data point before finalizing their six-figure gift, the pressure to respond quickly meets our professional obligation to be absolutely correct. ChatGPT makes this balancing act even trickier. Its confident, polished responses can mask a dangerous problem: AI hallucinations—fabricated information delivered with complete assurance. These aren't intentional l...