Let's Talk Fundraising

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...

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 i...

The Fundraiser's AI Starter Suite

If Sunday nights feel like the slow countdown to another heavy Monday, you’re not alone. I know that tightening in your chest — the mental list of donor follow-ups, board reports, events that need funding, and the quiet weight of a mission too big for one person to carry.

For years, I fought through it with a brave face and a tired heart. I thought if I just worked harder, smiled brighter, or sl...

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...

Your browser groans under the weight of countless tabs while your prospect's name stares at you from the CRM dashboard. The research rabbit hole keeps getting deeper, consuming hours of your day with diminishing returns. Sound familiar?

Prospect research doesn't have to be this way. The real power in donor profiles isn't found in data volume but in actionable insights that spark meaningful conversations. Yet...

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 th...

Drowning in donor emails while struggling to craft thoughtful, personalized responses? You're not alone. Fundraisers everywhere face this daily challenge—balancing the need for authentic communication with the reality of limited time and mounting inbox pressure.

The secret most successful fundraisers discover is that timely responsiveness isn't just an administrative task—it's a relationship-building superpo...

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—fabricate...

Ever found yourself paralyzed by a blinking cursor, struggling to craft the perfect donor message? You're not alone. Fundraising writing can be deeply intimidating—it needs to reflect understanding, empathy, clarity, and warmth all at once while connecting emotionally with donors.

The secret to breaking through this paralysis lies in a simple mindset shift: momentum beats perfection. Every time. Rather than agonizing ...

Every fundraiser knows that donor trust is the foundation of successful philanthropic relationships. But in our rush to embrace powerful AI tools like ChatGPT, we risk compromising that trust through accidental exposure of sensitive information. What begins as an innocent copy-paste into an AI prompt can instantly transform into a serious data breach that damages hard-earned relationships.

This episode tackles the critical...

Trapped in an endless cycle of drafting donor emails while meaningful connections take a backseat? The silent crisis of administrative drag is depleting fundraisers' energy and passion nationwide. What if reclaiming hours every week could be as simple as embracing the right technological tools?

This transformative exploration reveals how AI tools like ChatGPT can revolutionize your fundraising practice—not by replacin...

Have you ever left a donor meeting wondering, “Why did I say it like that?”
Or felt that quiet pressure to be more agreeable, more polished, more… perfect?

In this episode, Keith shares a story fresh from the road—an alumni reception that turned into a powerful reminder: you don’t have to be everyone’s favorite to be an exceptional fundraiser.

If you’ve ever struggled with people-pleasing, felt the weight of performance, or quest...

Ever poured hours into a project only to watch it get worse, not better? That frustrating cycle of diminishing returns might be fueled by a deeply-held belief that's actually holding you back.

Growing up, I absorbed my father's working-class ethos that hard work—defined by time spent, effort exerted, and suffering endured—was the only path to success. This belief followed me through school and into my career, whe...

Have you ever left a donor meeting, recorded quick thoughts on your phone, then spent hours translating those scattered notes into a proper contact report? There's a better way.

At AFP Icon in Seattle last month, I watched a room full of fundraisers experience a collective "aha" moment. It wasn't sparked by fancy tech demos or pie-in-the-sky AI promises. It happened when they realized that tools like Ch...

The journey from behind-the-scenes prospect researcher to frontline major gift officer can feel like jumping into the deep end without a life vest. In this illuminating conversation, Matt Stokes, Leadership Giving Officer at Yale University, shares his experience making this challenging career transition and the lessons he's learned along the way.

Matt brings a unique perspective, having spent years analyzing data and...

When you picture a successful fundraiser, do you imagine someone who commands the room, speaks eloquently without hesitation, and thrives in crowds of donors? That stereotype has dominated our field for decades—but what if the most powerful fundraising superpower isn't being heard, but truly hearing others?

Carissa Konesky, CFRE and advancement officer at Simon Fraser University, challenges this outdated notion throug...

Fundraising shouldn’t feel like manipulation. It shouldn’t leave donors feeling drained, guilty, or pressured into giving. Yet, so much of our industry—especially certain political campaigns—leans into fear as a motivator. And while fear might work once, it doesn’t build relationships. It doesn’t make donors want to come back.

You know what does? Joy.

In this episode, I’m sharing two unforgettable stories from my time in hospice fund...