Published by Tom Iselin
Learn tactics and strategies you need to become an expert at raising money and building a high-performance fundraising program. There are Interviews with industry experts, as well as dozens of practical tactics you can apply immediately to raise more money, improve your program's effectiveness, and inspire you about the art of fundraising.
Listen on Apple PodcastsYour Board Isn't Working: Why a Board Retreat Might Be the Best Investment Your Nonprofit Makes This Year Most nonprofit leaders know the scene. You're sitting in a board meeting watching the same three people carry the conversation while two members scroll their phones, one asks a question already answered in the pre-read materials, and another slips out early because "something came up." The meeting ends politely. No one throws a chair. But nothing really moves forward. This is how board dysfunction often shows up—not through dramatic conflict, but through something quieter and more damaging: under-engagement. Board members attend meetings but contribute little. They skim materials, avoid difficult conversations, they fail to respond to staff emails, and they remain observers rather than active leaders. At first glance it seems harmless. Meetings are calm. Disagreements are rare. But the cost is real. A few members end up carrying the entire board. Strategic discussions become shallow. Staff grow frustrated presenting ideas that receive little response. And gradually, expectations decline. Leadership turns into attendance. At that point the board meeting starts to resemble a pleasant dinner party—friendly conversation, plenty of nodding, and very few decisions. And when that happens, the organization begins to drift. When this type of drift happens, one of the smartest investments a nonprofit can make is a well-designed board retreat—an opportunity to step back, address culture, under-engagement, and reset expectations before the board stops leading and starts simply showing up. Listen in!
14 min
The Importance of Building a Donor Pipeline BEFORE You need It! Here's a truth most development directors don't want to admit out loud: Your donor base is quietly shrinking. Not because you're doing bad work. Not because your mission isn't compelling. Not because your fundraising team isn't trying. But because donors are human. They retire. They relocate. They redirect their giving. They get distracted by grandkids. They fall in love with a new cause. And sometimes, without warning, they just have a change of heart before writing that six-figure check you were sure was coming. If you are not consistently identifying and cultivating new donors, you are not building stability, you're borrowing time. Savvy fundraisers understand this. They are not paranoid. They are practical. They know fundraising is part math, part psychology, and part ongoing treasure hunt. And they know something else: The organizations that prospect consistently don't panic. The ones that don't . . . eventually do. Let's talk about how to build a donor pipeline that is deep, resilient, and slightly unstoppable.
14 min
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!
15 min
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.
16 min
Part 2 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, 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.
15 min
Part 1 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. 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.
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!
9 min
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!
17 min
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!
9 min
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!
6 min
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!
8 min
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 . . .
7 min
Your first face-to-face meeting with a donor isn't a sales pitch or interview. And it's definitely not the time to comb through the details for your 30-page strategic plan. It's a discovery conversation—a delightful dance where you listen, learn, and laugh. Apply the following 10 tactics to get your first meeting right and the odds of landing a second meeting (and ultimately a donation) jump to more than 70%. Not bad for the cost of a latte and scone. Listen in and learn . . .
6 min
Here's a crash course in what "not" to do when fundraising, what donors secretly loathe, and a short list of how to ask for money without breaking into hives. Listen in and learn . . .
10 min
Ah, the board retreat. A magical time when board members gather to dive into strategic discussions, unleash big ideas, and nod sagely at visionary plans. You laugh, you brainstorm, you may even awkwardly roleplay. By the end, you've covered walls with stickies and flipchart paper, deepened your culture, and high-fived over fresh possibilities. And then… nothing . Everyone returns home. Retreat outcomes are emailed but never opened. The notes from the flipcharts are filed away and the long list of follow-up ToDos sits unopened in Dropbox. Another week passes and the staff still waits for next steps. The energy? Gone. The ideas? Ghosted. And that beautiful vision for the future has faded into the background noise of daily operations. Welcome to the infamous retreat afterglow hangover —where inspiration without implementation goes to die. This podcast is your resuscitation manual for retreat outcomes. Because unless you want all that time, energy, and trust to evaporate like a dry erase marker, you need more than good intentions. You need action planning. You need structure. And most of all, you need ownership. Listen in and learn . . .
30 min
Fundraisers know that most donor objections boil down to just two things: the amount you're asking for and the timing of the ask. But here's the good news—both are manageable. In this article, you'll discover practical tactics to navigate these common roadblocks, plus smart ways to handle the trickier, less common objections that inevitably pop up. By the end, you'll not only be ready to face objections with confidence—you'll actually welcome them as opportunities to move the conversation forward and close more gifts. Listen in to learn A LOT more and there are scripts . . .
9 min
Encountering objections when asking donors for money is a given. One tactic for handling objections would be to develop and memorize canned responses to every possible type of objection. Experienced fundraisers know this tactic is futile, because a simple "ask" often triggers an avalanche of donor replies, ranging from polite deflections to excuses worthy of an improv show. A more effective approach is to master a simple process for handling objections that can be applied to any objection. Below is a simple, three-step process for handling objections. Just repeat it until you land a "yes," a "no," or an agreement on next steps—whether that means another meeting, sending a proposal, giving a tour, or showing off the blueprints for that shiny new facility. Tune in and learn . . .
17 min
Experienced fundraisers know objections are part of the ask process, which is why they embrace them. There are dozens of reasons why donors throw caution signs that feel like red lights. What follows is a high-level primer that unpacks why donors hesitate, paired with clear principles for handling those objections with confidence—so you can turn tough questions into lasting commitments. Listen in and learn!
10 min
Cultivation is the golden hour before the ask. It's when you introduce someone to your nonprofit, show them the heart behind the stats, the faces behind the facts, and the mission behind the jargon. And it isn't just about raising money—it's about raising friends, champions, connectors, and believers. Done well, cultivation deepens emotional connection, builds trust, and turns a casual observer into a loyal supporter. Done poorly, it feels like a used car sales pitch on a rainy afternoon. Listen in and learn!
16 min
As fundraisers, we know that while individual giving dominates, finding the right foundation, corporate, or government grant can give your budget a real boost. Many of these funding sources make large, multiyear commitments, and for some nonprofits, these sources of funding are their only sources of funding. And while unlocking these sources of funding can rain down large sums of money, they can also create a lot of wasted time and rejection letters. What follows is a set of tactics you can use to increase the probability of securing funds from these sources and to do it in a manner that is worth your time and effort. Listen in and learn . . .
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