The Fundraising Coach

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Board Retreat Blunders and Mistakes that Sabotage Retreats Jun 05, 2026

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Board Retreat Blunders and Mistakes that Sabotage Retreats

Board retreats are supposed to be powerful. They're supposed to create clarity, alignment, momentum, unity, and ownership. They're meant to be the moment when a board steps out of the day-to-day grind and finally gets honest about where the board is—and where it's going.

Instead? Too many retreats feel like a long, expensive meeting with better snacks. People show up with good intentions. They sit through presentations. They nod politely. They eat. They participate just enough to feel engaged. And then they leave.

And nothing really changes. No meaningful decisions. No real alignment. No unity. No ownership. No movement. Just a lingering sense that "we talked about some good stuff."

That's not a retreat. That's a missed opportunity. And after facilitating hundreds of board retreats across the country, I can tell you this with complete confidence: Most board retreats fail for predictable, avoidable reasons. Here are some classic board retreat blunders and mistakes you want to avoid. Listen in!

Part 3 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies Jun 05, 2026

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Part 3 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies

Most fundraisers spend far too much time worrying about the "perfect ask," as if somewhere out there is one magical sentence that makes every donor instantly reach for a checkbook. There isn't. Fundraising is not a Jedi mind trick, and donors are not slot machines you jiggle until money falls out.

The truth is much more practical: different donors respond to different types of asks, and the best fundraisers know how to choose the right one for the right person at the right moment.

That's why experienced fundraisers don't fall in love with just one asking style. They build a toolkit. They know when to keep it simple, when to make it visual, when to create momentum, when to lean into competition, and when to invite support without asking for money at all.

In other words, they don't walk into every donor meeting swinging the same hammer and hoping everything turns into a nail. They use judgment, timing, and a little creativity—which, frankly, beats awkward begging every time.

In Part 1 and Part 2, we covered the foundational and scalable ask strategies that drive day-to-day fundraising success.

In this final part of the series, we turn to long-term strategy—exploring the ask types that create stability, permanence, and legacy-level impact.

Part 2 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies Jun 05, 2026

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Part 2 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies

The truth is much more practical: different donors respond to different types of asks, and the best fundraisers know how to choose the right one for the right person at the right moment.

In Part 1, we covered five foundational ask tactics that help you start conversations and create momentum.

In this part of the series, we shift from momentum to structure—focusing on the ask tactics that build consistency, loyalty, and scalable revenue across your donor base.

Part 1 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies Jun 05, 2026

Show notes

Part 1 of 3: Ask Better, Raise More Money -- Fundraising Ask Tactics and Strategies

The truth is much more practical: different donors respond to different types of asks, and the best fundraisers know how to choose the right one for the right person at the right moment.

This three-part series breaks down 14 proven types of fundraising asks you can use to raise more money more effectively. In this first installment, we'll cover five foundational ask types that every fundraiser should have ready at all times.

Unresponsive Donors: A Smarter Way to Respond Apr 06, 2026

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If you've spent any time in fundraising, you know this moment well.

You send the email, make the call and follow up—politely, professionally, thoughtfully.

And then… nothing. No reply. No acknowledgment. No signal of interest or disinterest. Just silence.

For many fundraisers, donor silence feels personal. It triggers doubt. Did I say the wrong thing? Did I wait too long? Did they lose confidence in us? Should I push harder—or back off completely?

Here's the truth most fundraisers need to hear—and hear often:

Donor silence usually has very little to do with you.

But what you do after that silence? That part matters a lot.

This podcast will help you separate what's outside your control from what absolutely isn't—and show you how to respond in ways that build trust, loyalty, and long-term generosity.

Listen and learn!

The Year-End (Holiday) Fundraising Secrets Nobody Uses Apr 06, 2026

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The "Notify First" Trick There's one move that can turn your ho-hum year-end appeal into a home run: notify first!

Before you send a single email or stuff a single envelope, reach out to donors—by phone or email—and announce your campaign is coming.

This one act can boost your response rate up to five times higher. If you actually reach a donor and they feel connected to your cause, half of them will give. Do it well, and that number can soar 70%. Incredible.

But skip the notification and rely only on a generic appeal letter or email? Expect a limp response rate of just 1–3%. Maybe 5% if you're lucky. (It's like brewing coffee without heating the water—you'll still get something brown, but nobody's drinking it.)

Listen in and Learn!

Specialty Events: How To Turn Small Gatherings into Big Gifts Apr 06, 2026

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Let's be honest: most nonprofits don't need another event. They need better ones. The kind that doesn't drain staff, exhaust volunteers, or leave donors wondering why they just spent two hours listening to speeches when they could have been home in slippers. That's where specialty events come in.

Savvy fundraisers love specialty events—typically gatherings of 10 to 75 people—because they create something you simply can't replicate at a big gala. Donors see friends they respect, meet peers they admire, and experience your mission together. There's energy in the room. Momentum. A subtle but unmistakable sense that this is something worth being part of.

Listen in and Learn!

How to Fund Your Next Board Retreat or Strategic Planning Session Apr 06, 2026

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Every nonprofit eventually hits a moment of polite stagnation. Board meetings are full, calendars are packed, and everyone is working hard—but progress feels heavier than it should. Conversations repeat themselves. Decisions take longer. Direction becomes unclear. Passion wilts. The organization isn't broken, but it isn't quite clicking either.

That's usually when someone finally says what everyone else is thinking: "We should probably do a board retreat." Or, "Maybe it's time for a planning session." The idea hangs in the air for a moment, feels responsible and hopeful, and then gets quietly shut down with a familiar phrase: "We just don't have the budget for that right now."

That sentence sounds practical. It feels disciplined. And most of the time, it's the wrong conclusion.

Listen and Learn!

Board Members: Help Raise Money (Without Asking For It!) Apr 06, 2026

Show notes

Fear not! To raise money, you and your fellow board members don't have to cold call strangers (or worse, friends), or suffer through awkward donor coffees where you feel like the people at the table next to you are eavesdropping on your shaky pitch.

Nope. There's an alternative. It's a heck of a lot easier for board members to do things that support the fundraising efforts of the organization, rather than do something terrifying they loathe. Below is a list of 21 things board members with no fundraising experience can do to support the fundraising efforts of the organizations they care so much about.

And for those board members who love to ask for money, give them a list of people to call and meet, and let them work their magic. For everyone else, have them choose a few things from the list below. Their contributions will lower the work burden of the fundraising staff and provide valuable resources and impact that will ultimately help raise more money.

Listen in and learn!

10 Strategic Fundraising Principles - Every Fundraiser Should Know Nov 07, 2025

Show notes

Fundraising—it's part charm offensive, part emotional trapeze act, part caffeine-fueled chaos. Some days you feel like a philanthropic superhero, and other days you're crying into your donor database while searching for the 'undo' button. But you don't have to go it alone. Enter the Rainmakers: the mythical, magical, magnificently strategic fundraisers who know how to play the long game—with flair. What's their secret? These 10 fundraising principles. We're talking about donor stickiness, connection asks, custom everything, and enough 'You' language to make even Shakespeare blush. Strap in, folks. You're about to take a rollercoaster ride through fundraising best practices—Robin Williams style.

Listen and learn . . .

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