What you’ll get from this post: a way to stop competing for the same shrinking pile of cash and start asking for the assets donors actually hold, plus the two-question test that tells you which gifts help the donor and which ones quietly cost them.
A family in Minnesota once asked a fundraiser a simple question. Would your organization ever take a home in California as a gift?
The fundraiser said yes. Of course. Then the family said something that should stop every development director cold. They had asked another charity the same question five years earlier. That charity said no. It couldn’t do it.
Think about what walked out the door. A house. Net of the legal work, the travel, the cross-state paperwork, probably a real six-figure gift. Gone, because saying yes to something unfamiliar felt harder than saying no.
That story comes from Eric Wilke, who has spent 25 years in the nonprofit sector and now leads the FM Area Foundation in Fargo. He started in the trenches, a decade of program work at a place serving at-risk kids, before he moved into fundraising. He is not a lawyer, and he’ll tell you that himself. He knows just enough to be dangerous. That turns out to be exactly the right amount.
Here is the line that reorganizes how you think about a donor.
“99% of the nonprofits are fighting over 1% of the pot because not all of them will only take cash.”
Run the numbers on your own life. Whether you are 25 or 75, most of what you own is not sitting in a checking account. It’s the house. The retirement account. The stock you bought years ago. The farmland. The second property. Cash is the sliver on top.
Now look at how your organization asks for money. A check. Always a check. You are competing with every other nonprofit in town for the smallest slice of what your donors actually have.
The bigger slice is right there. It’s just harder to ask for, so almost nobody does.
This is the part that feels like a magic trick until you see the mechanics.
Say you bought something for a dollar and it’s worth a hundred now. A house, some land, a block of stock. If you sell it, you pay tax on that 99 dollars of growth. Capital gains. Depending on the asset, you might hand 20, 30, even 40 percent of the appreciation to taxes before a single dollar reaches the cause you love.
Now give the asset directly instead. Say you have a farm the kids don’t want. You could donate 40 acres of it to your church and sell the rest. The church sells the 40 acres and keeps 100 percent of the proceeds. No capital gains eats into it, because the charity doesn’t pay that tax.
Same generosity. Very different outcome. The donor still gets to keep what they need to live on, and the cause gets the full value instead of the after-tax leftovers.
Somewhere along the way, a story took hold that charitable deductions are a loophole for the wealthy. Wilke wants that one dead.
There’s no math where giving money away leaves you richer. If you kept the money and paid the tax, you’d have more in your pocket. Full stop. What a deduction does is reduce how much of that money goes to the government. That’s the whole mechanism.
Which means the only honest debate is about who spends it better. The nonprofit the donor chose, or the government. That’s a real debate, and Wilke will happily have it. What he won’t tolerate is the idea that someone is getting rich by giving money away. They aren’t. They end up with less either way.
He takes it a step further, and it’s worth sitting with. If you want to be angry about generosity in this country, don’t aim it at the people writing checks. Aim it at the ones who have the ability to give and do nothing. Promote philanthropy as a good thing and lift up the people doing it. The instinct to judge the wealthy who give misses the target entirely.
Wilke is blunt about the frame here. This is not about saving the donor money. It’s about maximizing the charity they already love, and doing it with an asset that’s smart to give.
Early in his career, a mentor taught Wilke a distinction that every fundraiser should carry into every planned-giving conversation.
Picture a donor with two things worth 100,000 dollars each. An IRA and a life insurance policy. They have kids, and they have a charity they care about. What should go where?
The IRA is a bad asset to leave your kids. When they inherit it, they pay income tax on every dollar that comes out. The life insurance passes to them tax-free.
So the move is almost automatic once you see it. Leave the life insurance to the kids. They get the full 100,000. Leave the IRA to the charity, which pays no tax, so it also gets the full 100,000. Everybody nets more. The only thing standing between a donor and that outcome is a fundraiser who knew to bring it up.
Here’s the same idea at a smaller scale, because you don’t need a wealthy donor for this to matter. A gift of 1,000 dollars a year, forever, takes less than 25,000 dollars set aside to fund. That might be a modest condo the kids are dreading having to clean out and sell. Deed it to the charity, let them endow the proceeds, and the donor’s annual gift outlives the donor. The check keeps arriving after they’re gone.
Explain a community foundation at a dinner party and you’ll watch eyes glaze. Wilke has a better handle on it than most, because he’ll tell you plainly what it is and who it isn’t for.
Think of it as a family’s charitable checkbook. One fund, held in one place, for all your giving. You make one contribution, take one deduction, and the foundation gets the money out to the five or six causes you care about. It’s convenient if your giving is spread across many organizations, or if you want to pull your kids and grandkids into the habit, or if you’d rather handle the paperwork once a year instead of every time.
Here’s the part that builds trust. The foundation says no to people all the time. If someone gives to exactly one charity and loves it, Wilke tells them they probably don’t need him. Write the check straight to the organization. You don’t need a middleman for that.
That willingness to talk people out of a fund is exactly why the ones who do open a fund believe him. The foundation isn’t trying to be the only place you give. It just wants you to be generous, and it bets that if you work with the local foundation, more of that money stays in the community. That’s a pitch that works precisely because it isn’t always pitching.
Wilke credits this one to Scott Holman, and it’s the sentence the whole conversation turns on.
“Giving has to be about the donor’s need to give and not the charity’s need to have.”
Chasing only cash is really about what you can get from a donor right now. Listening for the right asset flips it. Now you’re helping them. You’re the one saying, you want to give this, so here’s the smartest way to do it.
That shift changes what a donor meeting is even for. You stop performing the pitch. You start asking what matters to them and then actually listening for the answer. If your organization turns out to be a fit, good. If a different asset or a different structure serves them better, you say so. The trust you build by doing that is the whole game.
Watch the difference between two ways into the same conversation.
The weak version sounds like a transaction. “We’re doing a year-end campaign and we’re short of goal. Can you help us get there?” You’re leading with your need. You’re asking them to solve your problem.
The strong version sounds like curiosity. “Tell me more about your aunt. I’m just curious.” That’s an actual line from the best story in this episode, and it led to the biggest gift the organization had ever received.
Here’s how that one went. Wilke met a generous couple who had never given to the charity he worked for. In conversation, the woman mentioned a great-aunt she’d always been curious about, someone who had worked at a school Wilke had connections to. He didn’t pitch. He called the school’s archives, found photos and stories of a remarkable woman who gave up her own paycheck during the Depression so the school could stay open, and dropped the whole pile in a milk crate outside the donor’s house. He barely even saw her that day.
Weeks later they sat in her living room for an hour and a half and never once talked about the charity. Then came a million dollar gift, the first the organization had ever received. Her husband said it happened because of the time they spent. And as she pulled Wilke in for a hug, she said, “Thank you for asking me.”
She gave a million dollars and thanked him for the chance to do it. That’s the donor’s need to give, made real.
There’s a misread that runs deep in fundraising. The belief that you need the story buttoned up before you walk in. The pitch ready, the one-pager printed, the empathy and the authority lined up in a row.
Flip it. The most important trait of a storyteller is the ability to listen to a story. Max says it often, and it lands hard in this context. The organizations that do this well are the ones asking donors why they care and then getting out of the way. The tightest script in the room rarely wins. The best honest question does. You need to get to know the person across the table, figure out what matters to them, and only then figure out whether your cause is a fit for what they already want to do.
Wilke learned this in the trenches long before he learned it in fundraising. A decade of program work with at-risk kids, coming in off the clock to take a kid to a movie because that was the only way to make the time meaningful. Nobody questioned it. Everybody did it. That’s where he learned what the hard work at the ground level is actually worth, and it’s why he values the work of funding it now. You can’t fake that respect. Donors can tell when you have it.
So here’s the pivot most organizations need. Get as good at hearing a story as you are at telling one. Get the donor talking about why they care, and the gift often tells you what it wants to be.
A lot of fundraisers hear that story and think, that’s nice, I don’t have time for that. Wilke’s response is direct. If you don’t have time for that work, you’re leaving the gift on the table too.
The fear underneath it all is the ask itself. We’re so afraid to make it. Max writes about this in Seasons of Story: we have to be brave enough to ask, because people need to know they’re wanted and needed. Waiting quietly for someone to volunteer a gift feels like humility. It’s usually ego. It protects you from a no at the cost of a yes that person actually wanted to give.
Wilke’s framing takes the pressure off both sides. You have every right to ask. They have every right to say no. Lay the mission on their heart and let them decide. High-net-worth donors especially don’t need you managing their choices. They earned that money making better calls than you’ll ever make with it. Your job is to put the opportunity in front of them, honestly, and trust them to be the smart people they are.
Pick one. Do it this week. The point is to move, not to overhaul your whole program at once.
This week, 30 minutes: Pull your top 20 donors and write one non-cash question next to each name. What might this person own that they’d give if someone asked? A business, land, appreciated stock, a second home. You’re building a listening list, not a solicitation list.
This week, one hour: Learn the IRA-versus-life-insurance distinction cold enough to explain it across a coffee table. If you can walk a donor through why the IRA should go to the charity and the life insurance to the kids, you can add real value in a single conversation.
This month, one conversation: Take one loyal donor to coffee with no agenda and no ask. Ask what they care about and why. Listen twice as much as you talk. See what surfaces when you’re not steering toward a gift.
This month, one call: Phone your local community foundation and ask how they handle complex or non-cash gifts. You don’t have to become the expert. You have to know who to call when a donor mentions the farm nobody wants.
This quarter, one policy: Write down what your organization will and won’t accept, and make “we’ll figure out how to say yes” the default for unusual gifts. The California home walked because saying no was easier than doing the work. Decide now that you’ll do the work.
You don’t need a planned-giving department to use any of this. You need one conversation where you ask a better question and then get quiet.
The next time a donor mentions the lake home, the farm, the stock they’ve held for 20 years, don’t hear a complication. Hear a bigger gift than the one you were about to ask for. Then be brave enough to ask.
The notes are great. But if you’re ready to stop reading about storytelling and start investing in yours, let’s talk.
