Register for the AI Policy Development webinar. AI is already inside your fundraising work, whether your organization has admitted it or not. You can see it in the draft that comes back a little too fast, a little too polished, and somehow less specific to the moment. And when donor communications start to feel like “everyone and no one,” the problem isn’t style. It’s trust. We start with a scene from the HBO show Hacks where a tech investor tries to sell a comedian on using AI to gene...
Jun 1
25 min
I recorded this episode on the Sunday before Memorial Day, thinking about an event called Celebration of Life that I helped build on the Big Island of Hawai'i. Lanterns on Reed's Bay. The Hawaiian nose flute. More than three thousand people on the shore singing Hawai'i Aloha at dusk. And what it taught me about what people are really doing when they make a gift in memory of someone they've lost. This episode is about memorial giving, and specifically about what most fundraisers miss when a me...
May 25
23 min
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...
May 4
24 min
This is the episode where we stop painting the picture and start talking about what happens next. If you've been listening to this series for a few weeks and something has started to click, this one is for you. You've recognized the moments. You've said "yeah, that's me" more than once. And now there's a quieter question underneath it all: are you going to do something about this, or keep circling? Keith opens with a story from earlier in his career, sitting in his supervisor's office, holdin...
Apr 27
29 min
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...
Apr 20
32 min
If you’ve been listening to this series and thinking… “This sounds interesting… but I’m not sure it would actually work for me…” This episode is for you. Because that hesitation you’re feeling? It’s not random. And it’s not a sign that you’re behind. It’s actually pointing to the exact places where your work matters most, your time, your donors, your relationships, your results. In this episode, I’m walking through what I’ve been hearing from fundraisers over the last few weeks, the quiet “ye...
Apr 13
22 min
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...
Apr 6
35 min
There’s a moment in fundraising where you start to feel it. You’re doing the work. You’re following up. You’re being thoughtful in your outreach. And still… things just aren’t moving the way they used to. Response rates are slower. Conversations take longer to start. What used to feel straightforward now feels heavier. It’s easy to assume the problem is in the execution. Maybe the message needs to be stronger. Maybe the research needs to go deeper. Maybe you just need to try harder. But what ...
Mar 30
33 min
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...
Mar 23
32 min
Fundraising moves when relationships move. And relationships move when the friction falls away. In this episode, we explore how AI can quietly support every stage of the major gift cycle without replacing the human heart of the work. From prospect identification to stewardship, you’ll hear how practical AI workflows can reduce administrative drag so you can show up with donors more present, more prepared, and more confident. We walk through the major gift cycle step by step and explore how AI...
Mar 16
31 min
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