The critical thing to understand is that just like with foundations, building professional relationships is key to your success.

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Relationships, Not Transactions

There’s a version of major gift fundraising that is essentially transactional: prospect identified, cultivation scheduled, ask made, gift received, stewardship letter sent, cycle repeated. It can work, to a certain extent. But that’s an older and less effective model.

There’s another version. The one where a donor calls your executive director on a Saturday because they read something that connects to your work. Where they bring a friend to a site visit who becomes your next major donor. Where their estate plan includes a bequest that funds your organization for years.

That version is built on a genuine relationship. And a genuine relationship with high-net-worth donors requires understanding what these individuals and families want from a philanthropic partnership. This advice is meant to be tailored: always work with your organization’s definition of what a major gift is and its level of readiness.

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What High Net Worth Donors Want

According to Altrata’s 2025 Ultra High Net Worth Philanthropy Report, the top motivations for significant philanthropic giving are not tax efficiency or social obligation. They are personal connection to cause, a desire for tangible impact, and a sense of partnership in the work they fund. These donors want to matter to your organization, not just to your budget.

In practice, that means access. Access to program staff, to the communities you serve, to the thinking behind your strategy. They want to understand your organization’s work at a depth that goes beyond your annual report. And they want their perspective—their questions, their network, their ideas—to be genuinely welcomed.

These deeper donor relationships take organizational preparation and readiness. Don’t rush things if you haven’t built a level of trust with your donor, even when you urgently need the funds. Don’t offend a great donor and throw the relationship off track.

The Donor Cultivation Moves That Work

Major donors value site visits and firsthand program immersion. Nothing builds a strong connection with high-net-worth donors like direct experience of your program. Not just a tour—an immersive experience—let them sit with participants, speak with staff, and observe the work’s complexity firsthand.

These kinds of engagements consistently lead to significant and sometimes transformational donations. This has been proven time and again over my 25 years in the field.

Facilitate access to your organizational leadership and thinking. Share a research finding before it goes public. These gestures communicate that this person is a partner in your mission, not just a name in a database.

Think about partnership opportunities appropriate for your particular organization and its style. Take it step by step, considering your organization’s size, staffing, and readiness. What is the right balance between partnerships and independence? What are your organization’s boundaries?

Some high-net-worth donors—particularly those with entrepreneurial backgrounds—want to do more than write a check. A named endowment, a challenge grant they design, a pilot program they help conceive. When a donor is genuinely invested, channeling that energy into something specific deepens the relationship and often increases the gift.

But don’t let donors direct your organization’s programs or strategy. Desires to do so should raise red flags. In the worst-case scenarios, these situations pull organizations into work that falls entirely outside their mission.

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A Word on Patience

Genuine relationships with high-net-worth donors are a long arc. It takes two or three years of consistent, thoughtful engagement before a truly significant gift materializes. Plan for this.

The fundraisers who build extraordinary major gift programs are genuinely curious about the people in their portfolios. They remember details from conversations months ago. They send a note when they read something that reminds them of what a donor cares about. That’s both a technique and an art.

What’s been your most effective major donor cultivation move? Let us know in the comments—we read every one.

Here’s the truth: the follow-up is part of the ask. Done well, it signals professionalism, genuine interest, and organizational competence.

Done badly, it signals desperation and makes program officers hide behind their out-of-office messages.

Let’s talk about how to do it right.

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First, Read the Room (and the Guidelines)

Before you do anything, go back to the funder’s website. Many private foundations spell out their LOI review timeline and whether they accept follow-up inquiries.

If the guidelines say “we will contact you,” that means you wait. Ignoring this instruction is the grant equivalent of texting someone back before they’ve had a chance to reply. Don’t be that person.

If the guidelines are silent on follow-up? You have a green light, with some ground rules.

The Two-Week Rule

Wait at least two weeks after submitting before reaching out. Foundations receive hundreds of LOIs during open cycles, and program officers are doing real work under real deadlines.

A follow-up sent two days after submission doesn’t show enthusiasm; it shows impatience.

After two weeks, a brief, professional email is entirely appropriate.

According to Candid’s LOI best practices, the goal of any follow-up should be to confirm receipt and offer to provide additional information, not to lobby for your proposal.

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What to Say (and What Not to Say)

Your follow-up email should be three paragraphs, max. Open by referencing your LOI, the date you submitted, and the organization and project name. Keep it specific so the reader doesn’t have to search their inbox.

Second paragraph: briefly restate why this project aligns with the foundation’s priorities. Not a full pitch, just a thread back to what matters to them.

Third paragraph: offer to answer any questions or provide supplementary materials, and thank them for their time.

Please don’t say: “Just circling back.” “I wanted to touch base.” “Following up on my follow-up.” These phrases have become so overused that they’re practically white noise.

As Vu Le of Nonprofit AF once quipped, “the nonprofit sector runs on a special dialect of buzzword soup that exhausts everyone, including the people writing it.” Be direct. Be human. Be specific.

One Follow-Up Call, Not Many

A short phone call is also appropriate, generally once. Leave a voicemail if they don’t answer, and be sure to pace your follow-up so you’re not overwhelming.

This is not a multi-channel marketing campaign. You are not trying to convert a lead. You are building a relationship, and relationships are built on respect for boundaries.

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Use the Waiting Period Productively

The weeks between your LOI and a funding decision are not dead time. This is your chance to follow the funder on social media, attend any public events they host, and track their recent grants to refine your understanding of their priorities.

By the time they reach back to you, you should know their grantmaking landscape better than you did the day you submitted your LOI.

Think of it like studying before a callback audition. You already impressed them enough to get a second look. Now show up prepared.

The Long Game

You need to understand that most LOIs don’t become full proposals on the first submission. Seasoned fundraisers know that a “not this cycle” response is often an invitation to try again.

A gracious, curious reply to a decline, asking what might make a stronger fit in the future, is one of the most underused tools in the field.

Seriously, showing that you’re not offended by being declined and following up for feedback is a great way to keep the conversation going.

The goal isn’t just one grant. It’s a funder relationship that funds your mission for years.

That’s the groove. Now go out and get it.

The free issue this week established the foundation: program officers want to trust you, they read faster than you think, and they genuinely want to say yes.

Today, we get into the mechanics of the conversations themselves—what to do before you pick up the phone or log in to Zoom, how to conduct a pre-submission call with confidence, how to navigate a site visit, how to follow up without being annoying, and what the red flags look like on both sides of the relationship.

I’m going to give you sample language to use in your communications. Scripts aren’t words you read verbatim—they’re scaffolds you internalize, so that when you’re in the moment, the right words come more naturally.

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I poured enormous energy into anticipating exactly what language would make a funder open their checkbook. But after some time in the trenches, and honestly, a few invaluable training courses, I learned the reality is simpler, yet far more demanding: they just want to trust you.

Program officers want the quiet confidence of knowing your organization will execute its plan. They want the assurance that if things go wrong mid-grant, you’ll pick up the phone instead of hiding behind a slick final report. Your budget, your narrative, your meticulously mapped logic model? They all exist for one singular purpose: to lay out your case and prove you can be trusted.

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They Read Faster Than You Think

Most program officers manage between 50 and 200 applications per grant cycle, or docket. According to Candid’s research on funder practices, the average first read of a full proposal takes less than 15 minutes.

Your executive summary and needs statement get the most attention; middle sections are often skimmed unless the opening earns deeper engagement.

This isn’t a reason to cut corners on methods or evaluation—it’s a reason to make absolutely certain your first two pages are doing their full job.

They Want to Say Yes

Program officers aren’t adversaries looking for reasons to decline your proposal. They chose this work because they believe philanthropy creates change.

When they pick up your application, they are hoping—genuinely—that it’s the one that makes their decision easy.

Your job is to make it easy: clear problem, credible solution, realistic budget, honest account of your track record.

Don’t make them hunt for basic information or bury your ask in hedged language.

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The Pre-Application Conversation

When a foundation makes pre-submission conversations available, take them. A brief, focused call before an LOI serves multiple purposes: it signals you’ve done your homework, gives you intelligence about current priorities, and begins a relationship.

A program officer who remembers a good conversation often brings more generosity to their reading of your proposal.

What do you ask? Ask something specific about the foundation’s current strategic priorities, whether your project type is a fit for this cycle, and whether there’s anything in the guidelines that needs particular attention.

What not to ask: anything that’s already answered on the foundation’s website, or anything that puts your program officer in an awkward position. These relationships can last decades, so value them.

They Notice When You Know Their Work

Program officers read enough proposals to develop a sharp radar for organizations that have genuinely engaged with a foundation’s priorities versus those recycling a proposal written for someone else.

The difference is usually visible in the first paragraph.

Before you write a word, read the foundation’s website, their most recent annual report, their strategic plan if public, and recent grant announcements in your issue area.

Then, personalize and write to that funder specifically—don’t address your email or LOI to a generic foundation.

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Honesty Is a Competitive Advantage

This fact surprises many people: program officers respond better to honest acknowledgment of limitations than to polished overconfidence.

An organization that says “this is a pilot; we expect to learn and adjust” reads as more credible than one promising guaranteed outcomes on new campaigns.

Your relationship with a program officer is the longest game in fundraising. Proposals come and go. Relationships built honestly over years are what produce the sustained funding that makes transformational work possible.

Coming this Thursday in Premium: the program officer conversation itself—scripts, etiquette, what to ask, what to avoid, and how to read the room when a meeting isn’t going the way you hoped.

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Picture this: you open a generous grant check from Fidelity Charitable or a local community foundation, but you are left scratching your head about who really made the gift.

If you’ve been in fundraising for more than a few years, this scenario is probably all too familiar: a mystery person made a significant gift through a donor-advised fund (DAF). How do you thank them, and how do you build a relationship with them?

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Why DAFs are a Priority

If you don’t yet have a clear picture of exactly how DAFs work and what they mean for your donor relationships, it’s time to develop one.

The numbers make this an urgent priority for any nonprofit professional. According to the National Philanthropic Trust’s 2024 DAF Report, there are now over $326 billion in assets held in donor-advised funds, which is up 30% from the prior year.

Furthermore, DAF giftmaking to nonprofits reached a staggering $54 billion in 2024. This represents one of the primary channels through which significant philanthropic capital now flows, and you want to ensure your organization is ready to receive these gifts.

What a DAF Fundamentally Is

A donor-advised fund is a personal charitable giving account held at a sponsoring organization. This sponsor is typically a community foundation or the charitable arm of a financial institution, such as Schwab Charitable, Fidelity Charitable, or Vanguard Charitable.

The donor contributes assets, takes an immediate charitable tax deduction, and then recommends grants to specific nonprofits over time at their own pace.

As Candid Learning notes, this differs from private foundations, which must make qualifying charitable distributions each year equal to roughly 5% of the average value of their non‑charitable‑use (investment) assets.

Donors love these funds because the tax deduction is immediate and applies to the full fair market value of the contribution, even if the resulting grants are distributed over several years.

For instance, a donor who sells a business or receives a large bonus can contribute to their DAF in a high-income year, take the full deduction, and then thoughtfully give to their favorite nonprofits over the next decade. It is a strategic planning tool for donors just as much as a convenient giving vehicle.

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What This Means for Your Organization

DAF gifts typically arrive with the sponsoring organization’s name on the check rather than the donor’s name. This creates a specific cultivation challenge since you might not initially know who provided the funds.

When a DAF gift arrives, always check first whether any identifying information is included, as many platforms now allow donors to attach their name to the grant recommendation.

If their information is there, reach out personally to begin or deepen the relationship. If it’s not included, then promptly acknowledge the gift to the sponsoring organization and flag the transaction in your CRM for potential future identification.

How to Signal That You Are DAF-Ready

Many nonprofits are perfectly equipped to receive DAF grants but simply have not told their donors. This is a massive missed opportunity.

Research shows that DAF donors give an average of 4.2 times per year compared to 2.8 times for traditional donors, often at higher amounts and with much greater consistency.

If a donor who already loves your organization does not know you accept DAF grants seamlessly, they might not think to use that vehicle to support your mission.

Here are a few simple, highly effective ways to signal your DAF readiness to your community:

· Update your donate page: Add a clear line stating, “We gladly accept gifts from donor-advised funds. To give through your DAF, please use our legal name and EIN: [Organization Name], EIN [XX-XXXXXXX].”

· Include it in your outreach: Mention it in your year-end appeals and major gift conversations by asking, “Do you give through a donor-advised fund? We would be honored to be included in your annual distributions.”

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The Relationship Is With the Donor, Not the Sponsor

Keep in mind that the sponsoring organization is merely a financial vehicle. The true relationship is with the person who opened the DAF.

This is the connection that determines whether your organization continues to receive grants year after year, whether those gifts grow, and whether a donor eventually includes you in their estate plan.

Be sure to steward DAF donors exactly as you would any major donor by providing personal thank-yous, detailed impact updates, and exciting invitations to deepen engagement.

The fact that their gift came through a major financial institution does not change the core nature of the personal relationship you are building.

These are the basics. We’ll be covering DAFs in more detail in upcoming Premium issues, so keep an eye out for them.

We’re going to walk through each phase of the major gift cycle in depth: what you’re doing, what you’re listening for, how you know when to move forward, and what common mistakes to look for at each stage.

I’ll also share a framework for a moves-management tracker you can adapt for your own portfolio.

Fair warning: this is a long one. Pour something, settle in, and treat this as the working document it’s meant to be.

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What Is a Stablecoin, Exactly?

A stablecoin is a cryptocurrency designed to maintain a consistent value, typically by being pegged to a fiat currency like the US dollar. USDC (USD Coin), USDT (Tether), and RLUSD (Ripple USD) are among the most widely used. When a donor sends you $10,000 in USDC, it is worth $10,000 upon arrival. Not $7,200 because Bitcoin had a rough Tuesday.

This is the fundamental problem stablecoins solve for nonprofit finance departments. The volatility of Bitcoin and Ethereum is real and it’s significant. A gift worth $25,000 at the moment of donation might be worth $18,000 by the time your organization receives and liquidates it. For organizations operating on tight budgets and trying to meet grant reporting requirements, that unpredictability is not a minor inconvenience. It’s a genuine barrier to adoption.

Stablecoins remove that barrier almost entirely.

The Numbers Behind the Surge

In 2025, donors gave over $32 million in stablecoins to nonprofits processed through The Giving Block, making stablecoins one of the fastest-growing segments of crypto philanthropy. That figure represents a dramatic increase from just two years prior, driven by a combination of growing stablecoin adoption among crypto holders and increasing nonprofit readiness to receive them.

USDC in particular has emerged as the preferred stablecoin for philanthropic giving — it’s issued by Circle, is audited monthly, and is widely regarded as one of the most transparent and reliable stablecoins in the market. According to Givepact, a crypto donation platform that works with more than 500,000 nonprofits, stablecoins have become the top donated asset class in crypto philanthropy.

USDC’s “dollar-denominated” design “supports more predictable donation values, giving nonprofits greater confidence when planning mission-critical budgets and programs.” USDT (Tether) has larger overall market share but has faced more scrutiny around its reserves.

For organizations building a gift acceptance policy, it’s worth specifying which stablecoins you’ll accept rather than leaving it open-ended.

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Who Gives in Stablecoins—and Why

Stablecoin donors tend to be sophisticated crypto users who have accumulated holdings across multiple digital assets. They may hold stablecoins specifically as a low-risk store of value within a crypto portfolio, or they may have converted volatile assets to stablecoins and are looking to deploy those funds charitably.

The tax treatment parallels what we covered with Bitcoin and Ethereum: cryptocurrency is property under IRS rules, so donors who give appreciated stablecoins—though stablecoins are designed not to appreciate significantly—can deduct the fair market value while avoiding capital gains. In practice, because stablecoins are pegged to the dollar, the tax advantage is smaller than with volatile crypto. But the transaction is still treated as a non-cash property gift, which means the same IRS documentation requirements apply.

What You Need to Accept Stablecoin Donations

The infrastructure for accepting stablecoins is essentially the same as for any cryptocurrency gift. You need:

A gift acceptance policy that explicitly names stablecoins. List the specific coins you’ll accept (USDC is a safe starting point). Your board needs to approve this, and it should address how quickly you’ll liquidate to USD.

A platform that handles the conversion. The Giving Block and Donorbox both support stablecoin donations and convert to USD for deposit. The mechanics of holding a crypto wallet, managing private keys, and navigating blockchain transactions are handled by the platform — not by you.

A donor-facing landing page that explains you accept crypto, including stablecoins. Many stablecoin donors don’t know their favorite nonprofits can receive these gifts because organizations haven’t told them.

The Budget Conversation With Your Finance Team

Here’s the pitch for your CFO or finance committee: stablecoin donations arrive as USD-equivalent within one to two business days after the donor gives, with no exposure to crypto price volatility. The transaction is documented, the donor receives the required IRS acknowledgment, and the dollars land in your bank account like any other gift.

For finance departments that have resisted crypto donations because of volatility risk and accounting complexity, stablecoins address those objections directly. The conversation is different when you can say: this is effectively the same as an ACH transfer from a donor’s bank account, routed through a different technological rail.

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A Note on What’s Coming

The stablecoin landscape is still evolving, but regulatory clarity in the US has taken a significant leap forward. In 2025, Congress passed the GENIUS Act (Guiding and Establishing National Innovation for U.S. Stablecoins), the first federal framework regulating stablecoin issuers and establishing payment stablecoins as cash-equivalent assets. For nonprofits, this is a meaningful shift: it eliminates board-level concerns about issuer solvency and legitimizes stablecoin gifts, making finance committee conversations considerably easier. RLUSD, Ripple’s entry into the dollar-pegged stablecoin market, launched in late 2024 and is growing quickly in the philanthropic space. Keep an eye on it.

For nonprofits just beginning to engage with crypto philanthropy, stablecoins are a genuinely accessible entry point. The volatility concern (often the first and loudest objection) simply doesn’t apply here. The donor pool is real, growing, and philanthropically motivated. And the infrastructure to receive these gifts is more and more nonprofit-friendly.

New to the crypto conversation entirely? Go back and read the April 28 issue first—it’s the foundation. Then come back here.

Let’s build a needs statement from the ground up—sourcing real data, structuring the argument, weaving in community voice, and avoiding the mistakes that cause otherwise strong proposals to lose. This is the guide I wish I’d had when I was starting out.

Set aside an hour, open a draft document alongside this, and work through it as you read. By the end, you should have the bones of a needs statement that can anchor a competitive proposal.

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Your first draft of a proposal is often decent. The problem is the second draft that looks too much like the first.

It’s easy to write a competent first draft and then make small edits around the edges. We tighten a sentence here, swap a word there, and fix a few transitions. What we end up with is a tidier version of the original.

But adequate doesn’t win grants. Compelling does. Let’s walk through the essentials of making strong revisions.

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One of the Most Common Problems: Abstraction

Here’s a sentence pulled from a real grant proposal (with details changed): “Our program serves vulnerable youth in under-resourced communities by providing wraparound support services that address the root causes of educational inequity.”

Read that again. What do you actually know after reading it? Not much. Who is being served, and how many of them? Where? What does “wraparound support” mean in practice? What root causes? That sentence could describe thousands of programs, and it makes none of them feel real.

Now consider this revision: “Each year, our program provides 60 high school students from New York’s Iron Triangle neighborhood with paid conservation internships, weekly mentorship, and college application coaching, all while they earn an industry certification in environmental science.”

That sentence tells a story. It has numbers, geography, and activities you can picture. It makes the program tangible. Specificity is the single highest-leverage move you can make in a grant revision, and the good news is that it’s available in every draft you write.

Bring in the Voice of the People You Serve

Program officers are human beings, and human beings respond to human stories. An institutional narrative, with all statistics and outcomes but no people, reads like a report rather than a proposal. It informs, but it doesn’t move.

The fix isn’t to manufacture sentiment. It’s to use the real voices you already have access to. A direct quote from a program participant, gathered with consent, can do more work in two sentences than two paragraphs of organizational description.

Before: “Program participants report increased confidence and improved academic performance.”

After: “‘I didn’t think college was for me until this program,’ says Marcus, who completed the internship last summer and is now enrolled in community college. ‘For the first time, I felt like I was good at something that mattered.’”

That revision costs you nothing except the time it takes to collect the quote, and it changes everything about how the narrative lands.

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Cut the Jargon (All of It)

Every sector has its jargon, and the nonprofit sector has more than most. Wraparound services. Capacity-building. Systems change. Holistic approach. Two-generation model. Equity-centered framework.

These terms aren’t inherently wrong, but they’ve been so overused that they’ve lost most of their meaning. When program officers see them, their eyes glide over the words rather than stopping to engage with what’s underneath. Jargon is the enemy of specificity, and specificity helps win grants.

The revision move is simple: replace every piece of jargon with a concrete description of what you actually do. Don’t say “capacity-building.” Say “we train program staff in trauma-informed facilitation and provide monthly coaching from a licensed social worker.”

Describe what capacity-building means in your context. Say it plainly, painting a picture so the reviewer can visualize your program.

The Opening and Closing: Where You Win or Lose the Room

Program officers are busy and are reading through 10s or even 100s of proposals, depending on the foundation’s size. That means your opening and closing paragraphs get more attention than anything in the middle. Your opening sets the tone and signals to the program officer whether this proposal will be worth their time. Your closing is the last thing they carry with them when they put the application down.

Openings that work tend to share a few features. They might offer a specific, vivid scene, or a striking statistic followed immediately by its human implication. Sometimes they pose a question that the proposal then answers, or open with a brief story that encapsulates the problem you’re trying to solve.

Openings that don’t work sometimes sound like this: “Our organization was founded in 1998 with a mission to…” Nobody opens a great novel with a legal definition. Don’t open a proposal that way either.

Closings that work return to the human story you opened with, this time showing what change looks like. They might end on a forward-looking statement that connects the grant to something larger, or a clear, confident articulation of what success means and what it will make possible.

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The Final Step: Review and Revise Your Draft

Good proposal writing entails rewriting and revising, ensuring you answer all parts of each multi-part question in the narrative format you’ve been provided. (Each funder has its own format, so read it thoroughly.) Leaving enough time before the deadline to re-read your draft against the funder’s guidelines and scoring criteria.

Make sure your grammar, punctuation, and spelling are accurate. You’ll be dinged if they’re not.

These last steps are among the most important you can take to ensure your proposal is as competitive as possible. Give yourself that time. Your mission is worth it.

Over-reliance looks like this: a fundraiser gets a prospect report back from DonorSearch showing a $2 million capacity rating on a longtime annual fund donor and immediately starts treating them as a major gift prospect, without a single qualifying conversation.

They rush cultivation, the donor feels pressured, and the relationship suffers.

Ignoring it looks like this: a development director maintains a 300-person prospect list entirely from memory and board relationships, never uses any wealth screening tool, and misses a cluster of highly capable donors who’ve been quietly writing five-figure checks to peer organizations for years.

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The right relationship with wealth screening is somewhere in the middle: it’s a powerful prioritization tool that tells you where to focus your limited cultivation time—not a replacement for human judgment, relationship, and the qualification conversation.

Here’s how to use it well.

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This is called prospect qualification. It’s the phase of the major gift cycle that many organizations either skip or collapse into the cultivation phase, spending months building a relationship with someone who was never a realistic major gift prospect.

Your fundraising time is finite. Prospect qualification is one way you protect it.

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What Wealth Screening Can and Can’t Tell You

Wealth screening is a starting point, not a conclusion. Platforms like DonorSearch and iWave aggregate public data to produce prospect wealth-capacity estimates, which are genuinely useful for prioritizing a large prospect list.

According to DonorSearch’s research, donors with a history of charitable giving to other like-minded organizations, particularly at the major gift level, are the strongest indicator of likely major gift behavior. This history is more predictive even than raw wealth.

Here are some of the key variables wealth screening can’t tell you: whether this person has any connection to your mission, whether they’re already fully committed elsewhere philanthropically, whether a life event (a business sale, an inheritance, a divorce) has changed their financial picture recently, or whether they’re simply not interested in the kind of relationship that major gift fundraising requires.

That’s why the qualification, or discovery, conversation matters so much.

The Discovery Conversation: What It Is and Isn’t

A discovery conversation is not a pitch. I want to be clear about that, because the instinct to present and persuade runs deep in fundraisers. A discovery conversation is a genuinely curious conversation designed to learn a prospect. To learn about this person’s philanthropic interests, their relationship to your cause, and whether there’s a real fit between what they care about and what you do.

You’re listening for three things: enthusiasm (do they light up when they talk about your issue area?), specificity (can they articulate what kind of impact they want to make?), and ownership (do they talk about your organization’s work as something they feel part of, or as something happening at a distance?).

A couple of questions that open qualification conversations well:

“What first drew you to [your cause area]?” — This surfaces the origin story of their affinity and often reveals a personal connection that will shape everything about how you cultivate this prospect.

“What would meaningful impact look like to you in this space?” — This question surfaces whether their vision of impact aligns with what you actually do.

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The Signals That Say ‘Yes, Keep Going’

A prospect who asks detailed questions about your programs, who references specific things they’ve read or heard about your work, who talks about the issue area with evident passion and knowledge—these are green lights.

They’re telling you they’re engaged and interested. Keep going.

A prospect who speaks in generalities, who seems unfamiliar with your work despite having been on your list for years, who is clearly in the early stages of philanthropic exploration without a strong commitment to your area—these are red lights. Make notes about your conversation and move on to the next name on your list.

When to Disqualify a Prospect — and How

Disqualification is a portfolio management decision. If after one or two discovery conversations it’s clear that a prospect has limited affinity for your specific work, or is fully committed elsewhere, or doesn’t have the capacity your program requires, move them off your major gifts prospect list.

Move them to your mid-level program. Keep them on your event invitation list. Stay in

light touch. But don’t invest major gift cultivation resources in a relationship that doesn’t have the right signals. The relationship may still be worth maintaining, just not at the intensity of a major gift portfolio.

Sometimes a prospect you’ve moved to a lighter track comes back years later with a changed life situation and a deepened connection to your work. Qualification is not a permanent verdict. It’s a read of the current moment.

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Listen to Your Intuition

After enough discovery conversations, you develop a sense that signals whether something real is present. It will be a particular quality of attention in a prospect, a warmth in how they talk about your programs, an energy in the conversation. Don’t dismiss that intuition. It’s made of pattern recognition built over hundreds of human interactions, and it’s often right.

Write it down and record it in your database notes. “This person lights up when we talk about the wetlands work. Something personal there — ask next time.” That note in your CRM is the bridge between the intuition of this conversation and the cultivation move that follows.

Coming up this Thursday in Premium: Wealth Screening Demystified—how to effectively use tools like DonorSearch and iWave, what the data does and doesn’t tell you, and how to interpret a prospect report without over- or under-reading it.

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And then I got acquainted with the space, met people in the crypto-digital art sector, and started learning from good actors (I also got burned once or twice along the way). There are great people in crypto if you take the time to learn and be discerning. The underlying blockchain technology is fascinating. There’s a lot of generosity. Now, I’m paying attention to the giving numbers.

In 2025, The Giving Block—one of the leading crypto donation platforms for nonprofits—processed over $100 million in cryptocurrency donations on behalf of its nonprofit clients. The average crypto gift last year? $11,019. Compare that to the average online gift of around $128, and you start to see why this is an interesting conversation.

Crypto isn’t fringe anymore, that’s the reality. This is where a significant and growing pool of philanthropic capital lives. And if your organization isn’t set up to receive it, you’re leaving real money on the table.

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So What Exactly Is a Crypto Donation?

When a donor gives cryptocurrency to your nonprofit, they’re transferring digital assets—most commonly Bitcoin (BTC) or Ethereum (ETH), though dozens of others are accepted—directly to your organization’s digital wallet or through a platform that handles the conversion. The IRS treats crypto as property, not currency, which has important implications for both the donor and the organization.

Here’s the part donors love: if someone bought Bitcoin years ago at a low price and it’s now worth significantly more, they can donate that appreciated crypto and avoid paying capital gains tax on the appreciation—while still claiming the full fair market value as a charitable deduction. It’s the same principle as donating appreciated stock, which many of us are already well versed in. Crypto just brings a newer, often younger donor pool into that conversation.

Who Is Giving Crypto—and Why Should You Care?

Crypto donors skew younger (but, don’t overlook the boomers and GenXers), more tech-savvy, and often hold significant assets in digital form. They may not show up in traditional wealth-screening data. They may never write a check. But they’re philanthropically motivated and looking for organizations that speak their language.

As Inside Philanthropy put it, “Crypto is often discussed as speculation or ideology. In the nonprofit world, it should be discussed as something simpler: An asset class a lot of younger people already own, and one they can donate with less friction than using a credit card.”

In 2025, stablecoin donations (cryptocurrencies pegged to the US dollar, like USDC and USDT) also surged, with donors giving over $32 million in stablecoins alone. This matters because stablecoins don’t carry the volatility risk of Bitcoin—meaning that the value doesn’t swing wildly between when a gift is made and when it’s received.

For nonprofits worried about receiving a $10,000 gift that’s worth $6,000 on a bad Friday, stablecoins offer a more predictable option.

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What Do You Need to Get Started?

You don’t need to become a crypto expert. You need a few things:

• A gift acceptance policy that includes cryptocurrency. This is your first stop. Your board needs to approve a policy that addresses how crypto gifts will be received, valued, and liquidated—or held. Most organizations liquidate immediately to avoid volatility risk.

• A platform to receive and process donations. The Giving Block, Fundraise Up, and every.org all offer nonprofit-friendly crypto donation tools. They handle the technical heavy lifting, convert to cash, and provide the documentation your organization needs for IRS compliance.

• Basic donor communication. Create a landing page or FAQ on your website explaining that you accept crypto, how the process works, and the tax benefits. Many donors who hold crypto simply don’t know their favorite nonprofits can receive it.

These are the basics to get started. Your organization doesn’t need to hold crypto on your balance sheet. You don’t need a fully-dedicated staff person. You need a policy, a platform, and a landing page on your website.

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A Note on IRS Rules: For gifts of cryptocurrency valued at more than $250, your organization must provide a contemporaneous written acknowledgment, the same as with any other gift. For gifts of $500 or more, the donor needs to file IRS Form 8283 for non-cash charitable contributions. For gifts over $5,000, a qualified appraisal is required. A valuation simply reported by a cryptocurrency exchange does not satisfy this requirement.

We’ll spend more time on crypto philanthropy over the coming months—including this Thursday’s Premium deep dive on setting up your program step by step. But this is your starting line. The donors are already there. The question is whether your organization is ready to meet them.

The proposal is well-crafted, the project is genuinely good, the organization is credible. But somewhere between the cover page and the budget justification, the writer stopped thinking about the funder and went back to thinking about themselves. The narrative slides from “here is how we will advance your mission” to “here is why our mission deserves your money.” That’s a subtle but devastating shift.

Foundation funders are not writing checks out of charity alone. They’re making strategic investments in projects they believe will deliver on their own goals. The most successful nonprofit grant writers fully internalize this: they approach each funder not as a source of revenue, but as a partner with a distinct agenda—and they map their project to that agenda with precision.

This grant proposal alignment guide gives you the framework and tools to do exactly that, from your first foundation research session through to your final narrative pass. At its center is the Funder-Project Alignment Matrix—a fillable template you can use for every serious grant prospect. I’ve included the download links for your matrix and bonus material later in this Premium piece.

“The Tweed Run” Bicycle Race, London, England © Tonya Hennessey

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That difference matters. The skills that make someone strong at written fundraising do not always translate automatically to sitting down with a donor and making a personal ask for $10,000, $25,000, or $50,000. The encouraging news is that major gift fundraising is learnable. It is not reserved for a particular personality type; it is a discipline built on process, preparation, and consistency.

This guide from The Giving Groove offers a practical introduction to major gifts fundraising, including what qualifies as a major gift, what the major gift cycle looks like, how prospect research supports success, and why fundraisers often struggle when they move too quickly to the ask.

The Cotswolds UK © Tony…

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This paid version of The Giving Groove is for readers who want to think harder and go deeper on foundation and individual fundraising. It’s shaped by more than 25 years of work in the field, and by a lot of time spent paying close attention to what actually moves donors, money, and institutions.

I work my ass off for the organizations and causes I believe in. I love the craft of fundraising: the strategy, the psychology, the language, the judgment. And I care just as much about the kind of culture it can help create—a culture of contribution, responsibility, and shared belief in something beyond ourselves.

I hope these writings offer insight, practical shortcuts, and a few genuine aha moments. And that they’re smart, lively, and worth reading even when you don’t strictly “need” the advice.

The Beautiful Pacific Coastline, Jenner, California © Tonya Hennessey

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Today, let’s slow down and take a hard look at what separates the proposals that win from the ones that don’t.

I’ve written thousands of grant applications over the years as staff in organizations large and small that work on environmental, human rights, human welfare, and corporate accountability work. I’ve also worked as a consultant helping clients submit their own proposals.

The difference between a strong proposal and a losing one isn’t always the quality of the program. It’s often the architecture: how the proposal is built, what it says and when it says it, and whether the whole thing holds together as a coherent argument.

This masterclass piece is a deep dive. We’re going to do a proposal teardown, looking at what each section must accomplish, what the most common flaws are at each stage, and which language patterns work best. I’ll share real annotated examples where I can. Pour yourself something tasty and settle in.

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Telephones Over Time Exhibit, San Francisco International Airport © Tonya Hennessey

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Start With Local Data—Not Just National Statistics

National statistics are table stakes. Every proposal on food insecurity cites USDA hunger data. Every environmental justice proposal cites EPA pollution figures. That’s not wrong—context matters—but local data is where you can differentiate yourself.

Dig into your county health department’s data. Check your city’s planning documents. Look at school district reports, local housing authority data, and census tract-level information from the American Community Survey. If you serve a specific geographic area, make the funder see that area. Numbers that are specific to your community signal that you know your community.

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If yours makes them work to find what they need, they’ll move on. If your application package guides them clearly, you’ve already earned goodwill before they finish reading.

After more than 25 years in this work, I think of a well-structured grant proposal the way a good author thinks about a book: every section has a job to do, and when each one does its job well, the whole thing holds.

Here’s how to build it.

Me in Beijing, early 2012

The Cover Page: Your First Impression

Don’t overthink this, but don’t skip it either. Your cover page should clearly state your organization’s name, the project title, the funding amount you’re requesting, the project period, your primary contact information, and the date of submission. Some funders provide a requ…

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The Giving Groove is now hosted at groove.tonyahennessey.com. We are still fully integrated with Substack, but moving to a subdomain of my main fundraising and travel writing website allows me to maintain control of my intellectual property. (A huge thank you to Substack for generously allowing creatives to do this!)

Nosara, Costa Rica, 2010 © Tonya Hennessey

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I am thrilled to announce that Premium is officially launching in mid-April!

After 30 years in the trade I love, it’s time to share the deep-dive strategies that actually move the needle. Subscriptions will start at just $8/month or $80/year (pricing will increase over time, so lock in this early rate).

H…

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No. Absolutely not. Hard stop.

Here’s the counterintuitive truth: economic uncertainty is actually your moment. It’s when donors need to hear from you most — and when the strongest relationships get forged. Think of it like the gym in January. Everyone shows up when it’s easy. The people who show up in the cold, dark middle of February? Those are the ones who actually get results.

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Lake Geneva, Montreux, Switzerland © Tonya Hennessey

Relationship First. Ask Second. Always.

Major donor cultivation has never been about transactions — it’s about trust. And trust doesn’t pause for economic cycles.

According to the Association of Fundraising Professionals, “It is …

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