The Intentional Fundraiser Podcast

A donor rode a city bus at 6:15 a.m. He hadn't been on one since college.

The woman next to him had lived in that neighborhood for forty years. She was about to change his $250,000 gift.

They were riding the route families take to the local food pantry.

One hour and ten minutes. One transfer. And when they arrived, the doors didn't open until ten.

He looked at his watch and said, "Nobody who works a morning shift can do this."

She smiled. "That's what we've been trying to...

A 6:45 a.m. call from London. A donor wanted to give $1.5 million to the children's hospital that saved her little brother.

Her gift officer was thrilled. Thirty seconds later, she was terrified.

Because the donor was a US citizen living in London. Her husband was British. The money was in pounds. Their business had accounts in two countries.

Who gets the tax benefit? Which account does the money come from? What if the exchange rate moves?

Here's what I love. She didn't pretend to have the answers. She said, "I want...

Her mother's name was spelled wrong.

It was on the plaque. On dedication day. In front of her grandkids.

The mistake didn't end the relationship. What came next almost did.

The clinic took six weeks to fix it. Nobody called. The apology email said, "We apologize for any inconvenience."

The family went silent for a year.

Then a new major gift officer picked up the phone. She named what happened. She said she was sorry. She asked to hear about the donor's mom.

Forty-five minutes later, the...

My worst December as a fundraiser?

I spent it chasing a stock transfer with no name on it.

My plan had been "we'll get serious after the gala."

The gala ended in mid-November. You can guess how that year went.

Here's what I learned the hard way. December isn't where year-end is won. It's where you find out how well you planned in October.

And year-end 2026 raises the stakes. New tax rules. Donors who "bunched" their giving into last year. Complex gifts that need more lead time than ever.<...

One page changed everything.

A donor said it was the first report she'd ever kept.

Two years later, she made the largest gift in the organization's history.

It wasn't a glossy annual report. No pie charts. No forty pages.

Just one number she cared about, one note from a teacher, and one honest line about what the team was learning.

The difference? Her development director asked her what success looked like before she made the gift.

That's what this week's episode of The Intentional Fundraiser is all...

One question. A lasting legacy. Andrea almost didn't ask it.

She was afraid it would muddy her donor's renewal.

Her donor, Walter, had given faithfully for eleven years.

He was about to renew his major gift. And he kept asking one thing: "Will this program still be here someday?"

Andrea realized Walter was already having the legacy conversation. She just hadn't joined it yet.

So she asked: "What would you want this program to look like twenty years from now?"

That question led to a renewed and...

He went quiet for two months.

She thought she'd blown the ask.

She hadn't.

The donor had watched his business take a hit, watched the news every night, and frozen. He wasn't saying no to her $250,000 proposal. He was saying he didn't know how to say yes to anything right now.

Here's what she finally did.

She sent a note that had nothing to do with the gift. She just asked how he was thinking about the year ahead.

He called at 8:15 the next morning and talked...

She gave me four minutes. It changed my career.

Almost thirty years ago, I had a donor meeting with a man who genuinely intimidated me. My development director stopped by my desk and asked what I planned to ask him.

I recited my agenda. She listened, then said, "That's fine. But what do you really want to know about him?"

I said I wanted to know why he kept giving to us when he clearly didn't need us.

She said, "Ask him that."

He talked for twenty minutes about...

The lobby test.

Your website is the lobby of your building.

It never closes the gift. But it absolutely sets the tone for everything that happens around it.

In this week's episode of The Intentional Fundraiser, I tell the story of a six-figure donor who tried to give on her phone in December, gave up three screens in, and mailed a check instead.

The gift still came. The dashboard still looked healthy.

And a loyal donor quietly filed away one piece of information about the organization she loves: this...

"What's our plan if we only raise nine?"

A campaign chair asked that in a planning meeting for a $14 million campaign, and the room went completely quiet.

She wasn't being negative. She'd run a manufacturing business for thirty years, and she said, "I've never run a three-year plan that came in exactly where the model said it would."

So we built an answer. Three of them, honestly. Conservative, moderate, and optimistic, all built around one internal working goal.

Eighteen months later, the $4 million lead gift came in at $1.8 million.

...

A donor wall almost cost them their best donor.

At the opening of a gorgeous new wall, one of their most generous donors leaned in and said, "I didn't give so my name could be up there. I gave for the kids. I wish the wall told me about them."

That one sentence is the whole episode.

On this week's Intentional Fundraiser Podcast, Recognition That Feels Right Today, I dig into what donors are signaling about recognition now, fresh mission-centered practices you can borrow, and how to handle sensitive naming questions without walking...

Urgency can steal our future.

I’ve watched it happen in nonprofit teams everywhere.

We race from grant deadlines to events to year-end goals, doing everything possible to meet today’s needs.

But somewhere along the way, the relationship-building work that creates tomorrow’s major gifts gets pushed aside.

In my conversation with Mark Stuart, President and CEO of San Diego Foundation, I was reminded that fundraising is not just a development department responsibility.

It is a team sport. 🤝

When we make room for curiosity, courageous conversations, and long...

What if the ask isn't for money? What if it's a question?

A donor of fifteen years told one of my clients, "Nobody ever asked me what I thought. They just told me what they'd done." He'd made peace with being a checkbook.

I keep hearing versions of that story. Loyal donors who'd give more, and stay longer, if we simply asked them what they see.

On this week's episode of The Intentional Fundraiser, I make the case that listening is a fundraising strategy, not a courtesy. We get into how to design...

If you vanished tomorrow, would anyone else in your building

know how to talk about a donor with warmth?

I've watched two organizations, same size, same budget, same tactics. One had a major gift officer carrying every donor relationship alone. The other had a program director who told donor stories unprompted, because she'd been invited to sit in on a visit once and it stuck.

Same resources. Completely different trajectory.

On this week's episode of The Intentional Fundraiser, I dig into what a real culture of philanthropy looks like, why it...

He asked to sit in on hiring. She almost said yes to that too.

Here's what changed her mind.

On this week's episode, I tell the story of a major gift officer whose biggest donor had slowly taken over her evenings, her weekends, and nearly her hiring decisions.

We walk through the power dynamics that show up in almost every major gift relationship, the red flags worth naming early, and the reset language that protected both her dignity and the gift.

What's one boundary you've had to set with a generous...

A gift once took eleven months to close. Not because the donor said no.

Because one person was carrying five jobs.

On this week's episode of The Intentional Fundraiser, I tell the story of a major gift that stalled for nearly a year, and what finally unstuck it. Spoiler: it wasn't a better pitch. It was the right people in the room.

We talk about:

Who...

Her gala cost $40K. Her dinner cost $200.

Guess which one got a bigger gift.

On this week's episode, I tell the story of two events that happened the same spring, one an eleven-month gala, one a Wednesday dinner for eight people.

Only one of them led to real major gift conversations. It wasn't the expensive one.

We walk through the 3P framework I now use with clients: purpose, people, program, plus the follow-up system that turns a good event into an actual gift instead of a nice memory.

What's...

6:30 a.m. Calendar chaos already.

By 10 a.m., she hadn't talked to a single donor yet.

Six months later, same alarm, same portfolio. Totally different morning.

On this week's episode of The Intentional Fundraiser, I walk through what changed for a major gift officer named Renee, and exactly which categories of work she handed off to AI and automation, and which she never will.

In this episode, Working Smarter: Automation for Major Gift Officers, I cover:

→ The real numbers behind a 45-hour week, and where they were really going

A gala put them on stage. Then ghosted them for good.

Three community leaders invited up front, never contacted again. Zero gifts. One hurt feeling that traveled fast.

On this week's episode of The Intentional Fundraiser, I tell that story next to a very different one. A major gift officer who spent four months building trust with a community before she ever made an ask.

No agenda. No pitch. Just curiosity, and a lot of listening.

The result? A yes within a week, and two more families who joined in the...

What if your major donors wanted to commit longer?

Most of them already do. They just haven't been asked.

In this week's episode of The Intentional Fundraiser podcast, I'm talking about one of the most underused strategies in major gifts: recurring and multi-year commitments.

Not because donors resist them.

Because most fundraisers don't have the language to invite them in.

Here's what we cover:

$5k a year. For 12 years.

Then she sold her business.

The fundraiser said, "congratulations," and changed the subject.

Sixty days later, with one different question, that same donor transferred $400,000 in appreciated stock before the sale closed.

Same donor. Same relationship. Different question.

This week on The Intentional Fundraiser, I'm pulling back the curtain on what most major gift teams are quietly missing in 2026: asset-based gifts.

Stock. DAFs. Closely held business interests. Real estate.

These are not "planned giving department" conversations anymore. They are the next...

Your CEO is not your critic.

They might be your scariest internal customer.

Once I understood that, everything changed.

For years I walked into meetings with my ED ready to defend my portfolio. Why hadn't the gift closed. Why we were behind. Why the donor needed more time.

I left those meetings smaller. He left them more anxious. And the donor at the center of it had no idea any of it was happening.

Then I learned the move that changed my career.

I stopped reporting at...

$150,000 gift. One question.

90 seconds.

"Who is this changing for?"

A development director walked into a meeting with a fund-of-funds founder and a 12-page impact report. He flipped through it in ninety seconds and asked one question:

"Who is this changing for, and how do you know?"

She closed the report. Told one story. Showed one chart. One photo. Nine minutes.

Six days later, the $150K gift came in.

When she called to thank him, he said something I think about every week: "I don't need...

"You brought me a brochure, not a conversation."

A donor said that to one of my clients.

It changed how we prep every donor visit now.

In this week's episode of The Intentional Fundraiser podcast, I share the story of a $250,000 ask that became a $400,000 partnership plus two warm introductions, all because we changed one thing.

We stopped presenting.

We started designing.

Inside the episode you'll get:

A $100,000 gift, made in a kitchen.

The major gift officer wasn't there.

Another donor was. ☕

She invited three friends over for coffee. She told them why she gave. She didn't pitch. She didn't ask. Six weeks later, one of those friends called me ready to make a major gift.

That moment changed how the major gift officer thinks about major gift strategy.

🎙️ On this week's episode of The Intentional Fundraiser podcast, I unpack peer power, ambassadors, and giving circles, and why peer voices carry more weight than staff voices in 2026...

Bad metrics ruin good fundraisers.

Slowly. Quietly. Cycle after cycle.

And almost nobody on the team is allowed to say it out loud.

In this week's episode of The Intentional Fundraiser, I'm sharing why the metrics most major gift programs lean on, raw visit counts, dollars to goal, dials made, often miss the actual work.

I'm walking through:

→ The hidden cost of using lagging indicators to coach behavior

→ Five leading indicators worth tracking instead

→ Why AI inside your CRM should help you ask better questions, not de...

Pruning isn't loss. It's care.

For years, fundraisers have been told that a bigger portfolio means a healthier pipeline. In my experience, the opposite is usually true.

A focused list closes more gifts, and a focused fundraiser feels more human at the end of the week.

In this week's episode of The Intentional Fundraiser, I walk through the four lenses I use to decide who stays on an active portfolio, who graduates to stewardship, and who pauses for now. I also share the language to use with leadership when you propose a leaner...

"Fuzzy is the enemy of yes."

That line came up this week while I was recording the podcast.

And I cannot stop thinking about it.

Most major gift offers I see in 2026 are not failing because the relationship is weak or the mission is unclear. They are failing because the offer itself is fuzzy. A program description with a price tag at the bottom is not an offer. It is a proposal. And sophisticated donors can feel the difference.

In this week's episode of The Intentional Fundraiser podcast, I walk through...

Two donors. Same problem.

Completely different outcomes.

One development officer waited too long to call. By the time she reached out about a delayed project, the donor had already pulled back. A significant gift quietly disappeared.

The other officer called early. She was honest. She said, "Here's what happened, here's what we learned, and here's what we did to fix it." The donor's response?

"I really appreciate you telling me that. Most organizations only call when they want something."

The difference between those two outcomes wasn't strategy or skill...

Too many tools? Too little clarity?

And not enough hours to manage it all?

This episode is for you.

On this week's episode of The Intentional Fundraiser, I talk about what a healthy major gifts tech stack actually looks like, and what to do about everything that's built up around it.

We cover the four core tech categories that matter for major gifts work, a five-criteria framework for evaluating any tool in your stack, where AI genuinely fits in a major gifts fundraising context, and a simple ninety-day tune-up plan that...

AI won’t replace your voice, but it can help amplify it.

I’ve been talking with so many fundraisers who want to try AI but worry their donor communication will start sounding robotic. I get it. Authenticity matters more than ever in twenty‑twenty‑six.

On this week’s Intentional Fundraiser Podcast, I’m sharing how I use AI to draft and refine messages that still sound like me, while saving precious time for deeper donor connections.

How are you feeling about using AI in your fundraising communication?

Listen to “Writing Donor...

My calendar used to tell on me.

I’d get to Friday and realize I’d spent the whole week in meetings, email, and “urgent” internal stuff… while my top donors barely heard from me. Sound familiar?

In my latest episode of The Intentional Fundraiser, I share how I started treating my calendar like a major gift strategy tool, not a suggestion box. I walk through the three time blocks that changed everything for me, how to negotiate donor-first time with your boss and peers, and where AI can act like a junior assistant so you can fo...

Your next major donor might already be giving

I’ve seen so many mid-level donors quietly reading emails, showing up at events, and faithfully giving year after year, without ever being invited into a deeper conversation.

When we finally slow down, notice their behavior, and map a simple journey from “thank you” to “tell me what matters most to you,” everything starts to change. Gifts grow, trust deepens, and fundraising feels more relational and less transactional.

What if your best future major donor is already in your mid-level file, just waiting to be seen a lit...

When one question unlocks three streams of giving

In this week’s episode of The Intentional Fundraiser, I share the story of a longtime donor whose impact multiplied once we connected his personal philanthropy with his role as a corporate leader. We walk through practical ways to spot those “blended” opportunities, bring corporate options into donor conversations without feeling salesy, and use AI to uncover hidden corporate influence in your portfolio.

Are you leaving corporate partnership potential sitting quietly inside your major gift file right now?

Listen to this episode of “Corporate Giving as a Maj...

The biggest donors aren’t “the future” anymore. They’re already here.

In my latest episode of The Intentional Fundraiser, I share what I’m seeing as younger, women, and values‑driven donors rewrite the rules of major giving. From shorter cultivation cycles to co‑designing impact and bringing families and circles into the conversation, I walk you through real stories and practical moves you can start testing right away.

If donors want speed, transparency, and a true voice at the table, what needs to change first in your approach

🎧 Listen to this episode and share...

Your case might be costing you 7‑figure gifts.

In my latest episode of The Intentional Fundraiser, I share why so many cases still sound like they were written in 2019, and how I’m helping leaders like you update them for a 2026 donor mindset. I walk through the five elements of a modern case, where AI can truly help, and how to pressure‑test your message with trusted donors so they lean in instead of glazing over.

What would change for your organization if your case finally matched the level of impact you’re truly capable of? 🎧

One donor should never control your budget.

In this week’s episode of The Intentional Fundraiser, I share a story of a strong organization that felt “safe” until one major donor hit pause and everything started to wobble. We walk through how to map your top 20 donors, spot concentration risk, and start multi‑year commitment conversations that make your portfolio far more shock‑resistant.

How exposed are you to one donor’s decision right now?

Listen to this episode and share it with your team, your executive leader, or your board so you can strength...

Your discovery calls shouldn’t feel like a test.

In my latest Intentional Fundraiser episode, I walk through how I help fundraisers turn tense, scripted discovery calls into relaxed, donor-centered conversations that still move major gifts forward.

We unpack a simple four part framework, real examples of questions that open people up, and a practical way to use AI so you can listen more and type less.

What would change in your portfolio if every discovery call felt like a conversation you were both glad you had?

Listen to this episode of...

Leaders keep derailing donor visits?

I can’t tell you how many times I’ve watched a beautifully teed‑up donor conversation go sideways the moment a well‑intentioned CEO or board member “pops in” unbriefed. You’ve done the research, built the relationship, framed the invitation…and then the message gets fuzzy, the energy shifts, and the donor walks away more confused than inspired.

In my latest episode of The Intentional Fundraiser, I share how I’ve learned to turn those moments from chaotic to coordinated over nearly 30 years in major gifts. I walk you through the ex...

“More touches” are burning teams out 😅

I talk with so many fundraisers who are trying to do heartfelt, hyper-personal stewardship for everyone… and ending up exhausted, guilty, and behind by December.

In my latest episode of The Intentional Fundraiser, I share a simple 3-tier stewardship system I have used for years to keep donor care personal, scalable, and sustainable.

We get into: