Let's Talk Fundraising

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 a...

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 sessio...

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?

...

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...

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 ...

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 ...

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 ...

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 re...

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 wa...

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 exper...

Fundraising doesn’t belong only to the boldest voice in a crowded gala. It thrives in the quiet moments where a donor feels understood, a tense call cools with care, and a complex gift moves forward because someone listened long enough to hear what really matters. We sit down with advancement officer and CFRE Carissa Kineski to explore how introverts turn deep listening, patience, and empathy into durable donor relationships—and wh...

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 sho...

Every Valentine’s Day, nonprofit inboxes fill up with warm subject lines and messages that say, “We love our donors.” The intention is real, but the impact often falls flat.

In this episode, we unpack why broad gratitude is easy to send and easy to forget, and why donors don’t experience our effort or our process, they experience how they’re treated. The real question isn’t whether a message was handwritten or AI-assisted. It’s whet...

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...

🎁 Enter the contest to get a signed copy of Scott Vedder's book, Signs of a Great Resume.

Seven seconds. That’s often all you get before a recruiter decides “no” or “maybe.” We brought in Scott Vedder—former Fortune 100 recruiter and bestselling author of Signs of a Great Resume—to show how to turn a duty-heavy document into a sharp story of value that earns interviews, especially for fundraisers navigating fuzzy titles and co...

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.<...

Download the Big Goals Worksheet

The problem with so much “polished” AI content isn’t grammar, it’s judgment. We unpack why clean sentences can still feel hollow, and how fundraisers can use AI without outsourcing the thinking that protects the quality of your work. Instead of arguing for or against tools, we reframe the choice: Which role do you assign to AI, and which role do you keep for yourself?

We walk through four di...

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...

Year-end fundraising doesn’t have to feel like survival mode.

If you’ve ever spent December scrambling — rushing appeals, juggling Finance deadlines, and showing up exhausted for donors and family — you’re not alone. The truth is, survival mode isn’t a strategy. Steady rhythms are.

In this episode, I’ll share how to shift from frazzled to focused — and how AI can become the quiet assistant that keeps your year-end...