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Amy Eisenstein
Foreign.
Rhea Wong
Welcome to Nonprofit Lowdown. I'm your host, Rhea Wong. Hey, podcast listeners, Rhea Wong with you once again with Nonprofit Lowdown. Today I am so excited because my friend Amy Eisenstein is back on the pod. And today we are going to talk about all things capital campaign. Amy is the CEO, CEO and co founder of Capital Campaign Pro. She is an author, she is a podcaster. She is a YouTuber. Amy, welcome to the show.
Amy Eisenstein
Thanks so much, Rhea. That was really sweet.
Rhea Wong
Well, Amy, you have been an inspiration. I want to be like Amy when I grow up. Thank you for all that you do for all of the aspiring entrepreneurs out here.
Amy Eisenstein
Thank you. It's funny to think of myself as the older one, but so many consultants helped me along the way, and I am so, so honored to give back when I can.
Rhea Wong
Well, I also think it's kind of awesome that you are an OG YouTuber, because apparently now that is an aspiring occupation that kids want to have. I want to be a YouTuber. I guess that's the thing.
Amy Eisenstein
Now, I didn't know it was a
Rhea Wong
thing ahead of your time. You're just blazing the trail ahead.
Amy Eisenstein
Thank you.
Rhea Wong
Now, full disclosure, capital campaigns are not my area of expertise. I really focus on major gifts, but obviously these two things are very linked. I talk to a lot of nonprofits and everyone is very hip to talk about we want to do a capital campaign. And what I find very interesting is that it's not really dependent on size or sophistication of organizations. I've had very small grassroots nonprofits talk about wanting to do a capital campaign, which I thought was interesting. And then of course, we have the bigger ones that we think of as typically capital campaign ready, like universities and libraries and such. Before we get into this, can we define capital campaign? Because for a lot of us, we might think capital campaign and be thinking, okay, we need to build a building or a wing of the museum, but what do we mean when we talk about a capital campaign?
Amy Eisenstein
So to me, a capital campaign suggests a once in a while massive fundraising effort that will propel an organization to the next level of program or service. As you indicated, sometimes a building's involved, but certainly not always. Maybe they should be called capacity campaigns. Sometimes a building is involved, but sometimes not. But what makes them different from annual fund is that there is usually a big vision for the organization that gets them to really a different level of ability to serve the community that they serve based on this one big vision. It's a once in a while campaign. It's almost always a multi year endeavor, multi million dollars X times what they normally raise for the annual fund. But it's over and above the annual fund for one time needs that will propel them to the next level of service.
Rhea Wong
That's very helpful because I think level setting on what that actually means is going to be helpful for our conversation moving forward. So let's talk about what it means to be capital campaign ready and what red flags might be there for folks who are not. Because I do think that there's a little bit of a pie in the sky, magic fairy aspect to some people who think, oh, capital campaign, we just have to say the words and all of a sudden magic money will fly out of the sky.
Amy Eisenstein
Wouldn't that be great?
Rhea Wong
Listen, everyone is out here trying to get that mackenzie Scott money, which is basically the nonprofit lottery. And it's not a strategy. So what are the three to five things that you look at to assess whether an organization is capital campaign ready?
Amy Eisenstein
So the first thing I always ask about is what is the vision? What is the big project? What is the vision of the organization? And hopefully they've included the board in this process, this vision, visioning process. Right. So what is the big idea that is going to get them to where they want to go? And if they're not able to fairly clearly articulate this big vision, I know that we have more work to do that they have more work to do. So that's one thing. Another thing that is great is if they have at least a sense of who the big donors might be for this effort. So let me back up a teeny bit. So the big vision, how much is that going to cost? Right. So it's not, oh, we're having a 50th anniversary, so let's try and raise $50 million. Often an anniversary prompts a campaign, but then the question is, okay, we're turning 50, so we need to do some strategic planning to figure out where are we going in the next five to 10 to 50 years. And then what does that vision cost? Approximately our best estimates to execute. And that's your initial working goal. If it happens to be $50 million, fine. But usually it's not. It's something else. It will cost us $35 million or $20 million or whatever the number is approximately to get there. And of course, we want to include things like endowment or scholarship funds or maintenance funds, and lots of other things go into figuring out what the goal is. But okay, so big vision, approximately how much that costs to execute the vision. What will it take for us to realize the vision, then? A sense of who might or could give those big gifts. And as you said, it's not mackenzie Scott. Right. It's people that you know and trust in your community, among your donors. And simply because somebody has never given you a million dollars before doesn't mean that they won't. So don't panic if you say, oh my gosh, we don't have anybody who gives over $5,000. My response to that initially is, well, you've never had a multimillion dollar idea and you've never asked for a million dollars. So let's back up and do some research and thinking and investigating to see if we might have a sense of who those big donors could be. You need buy in from the board. We talked about that already. So let's start with those things.
Rhea Wong
Okay, so what are the things that would indicate that it's not a good time? Because to your point about the donors who have not given over $5,000, potentially, you want to ask them for a million. I'm just trying to thread the needle between aspirational and delusional.
Amy Eisenstein
Sometimes it's hard to figure out what that line is. So are there people who consistently give you gifts at whatever level, who are bigger philanthropists to other organizations in the community? So you might have somebody who gives you a thousand dollars a year, but they do you have a sense or you know that they give a million dollars to the hospital or to their university or to the library project or whatever it is. So just because they're not giving you those kind of gifts. Yeah. Doesn't mean that they can't or they won't. You may have some sense of these things and you may not. You may need a consultant or some other expert to help you do some data mining and some wealth screening and some brainstorming with your board. There's lots of ways to figure out who are those people. And the truth is, generally we help organizations identify who those big potential donors might be, and they are usually in their existing donor Base, even if they don't really know it yet.
Rhea Wong
Yeah, I say this all the time, which is major. Gifts are probably already in your donor base. You're sitting on a gold mine and you just don't know it. Now let's talk about the folks who come to you and they say, amy, we wanna do a capital campaign. And in your mind you're like, yeah, it's probably not the right time for you. What are the things that will tell you like, not yet.
Amy Eisenstein
So if they don't have a big vision. Right. They just wanna raise money for the sake of raising money or just to have a cushion or just to endowment, but they don't really have a vision. That's an issue. If they don't have buy in from the board. If the board doesn't know about this plan, if they're not excited about the plan, that's a problem. Something that tells me that they're bought in is that they're ready to do a feasibility study, they're ready to hire a consultant, shows me some buy in. So they should have done a lot of thinking about the vision. So if they come to us and say, okay, we're having a 50th anniversary, so we want to have a campaign, okay, so now it's time to do some strategic planning and figure out what do the next 10 to 50 years look like. So I guess some of those things. The other big thing is if they're operating at a deficit, we need to look at what's going on. Why are they operating at a deficit? How is the campaign going to help them and not just get them into a bigger hole? Right. So if they're operating at a deficit, we're going to ask some serious questions. Yeah.
Rhea Wong
Is there an organizational threshold at which you think a capital campaign is feasible? Would you say 5 million and up or does it just depend?
Amy Eisenstein
I think there's some idea to proportionate to the organization. So if you have a baby organization that wants to do $100,000 like mini campaign, that gives them a little boost. Great. That's a capital campaign for them. Most of the organizations we're working with are raising north of $5 million for a capital campaign for a big project and a big vision, 20 million, 50 million, 100 million. But I think there's no right or wrong scope or size. I've seen smaller organizations raise unbelievable multiples of what they do for their annual fund. And I think the bigger the vision and the more planning, the more exciting it can be. And donors want to be involved and they dig deep.
Rhea Wong
Let's talk about the multi year because I obviously have lots of Ed friends and I've seen this again and again where we have a capital campaign and everyone's excited about it and we're in the quiet phase and they're able to build a lot of momentum and then things kind of stall and they get into the multi year. Like, yeah, we're still working on this capital campaign. So can you talk us through what are some of the ways that you unstall the momentum of a capital campaign that is kind of stuck, Right?
Amy Eisenstein
So I think that most campaigns have ebbs and flows. There's periods of time where there's more momentum and then there's slower periods of time. And so I think when organizations are working with inexperienced campaign consultant, the consultant has a sense of, is this a normal ebb and flow or is this do we raise the alarms? But there's lots of strategies and tactics to regain momentum, re energize a campaign when it's in a downturn. And just remember, campaigns are long, right? They're usually three to four years, sometimes a little less, sometimes more. And so not every month or quarter is going to have the same amount of momentum and energy. And sometimes it takes a long time to cultivate some of the big gifts. And that's really the hard work of the campaign. So there may not be a lot of activity, but what is happening behind the scenes is going to make a huge difference in the result of the campaign. Let's say we're concerned about a stall or a slowdown. Some things you might do is insert a challenge opportunity, right? So if we're in the middle of a campaign and it's going to be different depending on the goal. But let's say we're working with donors at the 250 to $500,000 level, I might go to somebody and say, you know, would you commit a match of $3 million if we can find six donors to give half a million dollars each? And then say, all right, now I have a reason to go to the next six donors and say, look, we have this matching gift opportunity. Go to a donor for a million dollars and say, look, the next 10 people who give 100,000 each, we're going to match. So it's going to give us a reason to reach out to people, let them know that you've offered this match. And it just reinvigorates and reignites things and gets people back excited.
Rhea Wong
I mean, it is such a long game. And I think to your point about a lot of the work happening in the background really resonates because as we know, it can take a long time, especially for the bigger gifts. I want to transition a little bit because historically we've all been taught the fundraising pyramid. And I'm wondering in 2026, because what I've been hearing out here is donor behavior has really changed. I think it's harder to get people's attention. I think it's harder to build trust. So I'm curious, one, have you seen, seen changes in donor behaviors? And two, is the donor pyramid still relevant?
Amy Eisenstein
So we do an annual benchmark research report on capital campaigns and amazingly we find that the pyramid is still relevant. It still follows the pareto principle, the 8020 rule, or even the 9010. And so really, campaigns are highly, highly dependent on the first 20 gifts. And that's what, you know, we're really focused with our clients on, in the quiet phase of the campaign, among other things. But primarily those first 20 gifts that often come from about 50 prospective donors. So I, I don't think that's changed. That's really holding true among our client base and, and campaigns in general.
Rhea Wong
Their behavior in 2026 has that changed, Especially with all of the, the social media and the digital and just a lot of noise.
Amy Eisenstein
There is a lot of noise, right? Everybody's distracted. So I think it is important to sit down, have conversations, turn off that noise when you can. The people that really care about your cause. Remember, we're only talking about 20 gifts initially. That's gets you, it moves the needle so far in the campaign. So it's not about getting lots of people to pay attention. It's about finding the few people that really care that can move the needle in a big way. And so I think it is about developing those relationships. And you can be patient and take time to get to know people and to get their attention. And if you do, there's magic.
Rhea Wong
Yeah. Well, let's talk about the board. Cause you said obviously one of the ingredients in this magical cake is board buy in. Do you find that often the first 20 gifts are coming from the board?
Amy Eisenstein
We want the whole board giving in the quiet phase of the campaign, but probably only a small percentage of the board members are going to give the leadership level gifts. Most of the board members are going to give other size gifts, but we want them committing to the campaign early in a meaningful way. So those are two separate things. I would say we want the board stepping up and contributing and leading by example and making meaningful multi year pledges early as a sign of commitment and a show of support. But the reality is that most organizations only have a small handful of board members that could even consider some of those top 20 gifts. But you know the ones, the two or three that you have should be making those top gifts for sure.
Rhea Wong
And what do you do if you have a board who says, yes, we're behind it, yes, we can do it, and then they're not really showing up, they're not really doing what they need to do?
Amy Eisenstein
I guess I would say that it's all relative. So the question is, what do you need them to do? And not every board member needs to do the same things. We want every board member making a gift. We want every board member supporting the campaign. But what that means for each person is very different. Some board members are going to be on the leadership gifts committee and they're going to be helping solicit gifts, but most won't. We want everybody excited about the campaign. Is it appropriate for one or two or three of them to have house parties or meet and greets and invite their friends? Is it appropriate for others to bring prospective donors on tours? Is it appropriate for others to be writing thank you notes or making introductions or connections? So I think when you find that board members aren't doing what you hope or participating one is, it's time to perhaps reexamine what the expectations are. If you're expecting every board member to solicit leadership level gifts, I think you're going to be sorely disappointed. Right. But I would sit down with each board member and talk about what's going on, what do they want to do, what's most exciting to them about the campaign, how do they think they can help, what might they consider doing, but they would need training in order to do. What tools do they need to be successful, or what kind of coaching or mentoring or whatever it is. So this isn't to sit down with the whole board and ask these questions, although you can start the conversation in a board meeting and should. It's probably going to take place over multiple board meetings, but then there's going to be a lot of one on one conversations. So there are going to be lots of one on one conversations that need to happen as well. And some will rise to the challenge and some will play smaller roles. And I think that has to be okay.
Rhea Wong
So let's get to the meat of it because I think many folks listening might be thinking about the solicitation. And for the staff members who are nervous about solicitation, can you give us a step by step approach to moving someone from a prospect into a cultivation phase and then ineffective campaign ask? Especially when we're talking about the first three to five leadership gifts.
Amy Eisenstein
And yes, of course, I'm totally biased in that, but I think that the truth is that most nonprofit staff members and leaders don't have experience soliciting big gifts. And so it's not something that they should be making up or trying out or experiencing, experimenting with or hoping that they can do. It is nerve wracking.
Rhea Wong
Amy, this is why you and I have a job. It's like people need support, they don't know. And frankly, it is a very unnatural thing that we're asking people to do.
Amy Eisenstein
That's right. One of the things that we do here at Capital Campaign Pro is we have a feasibility study model where we're training and teaching and coaching nonprofit leaders to have interviews with their donors prior to asking for gifts. So we think it's really important that they have support in having strategic conversations with their donors about campaigns long before they have to ask for a gift. I never want nonprofit leader to be sitting down with the donor asking for a gift when they haven't had multiple opportunities for deep, thoughtful conversation. And so we start that process with the feasibility study. Some consultants do those interviews themselves. As consultants, we train nonprofit leaders and we coach very carefully them to have those conversations so that they do start to feel confident and comfortable meeting with their biggest potential donors, hearing their feedback and concerns and addressing them long before they ask for a gift. So that by the time they do ask for a gift, first of all, they've already been cultivating them. And honestly, they're much more comfortable already when it's time to do that.
Rhea Wong
And so what I'm finding, and I think this is so interesting, is I, in my experience with major gifts, have noticed that certain industries have certain ways that they like to interact. So I've raised money among finance people, I've raised money with tech people. And I've noticed that they tend to make decisions very quickly. They tend to want to just text me or just email me. I don't want to have a conversation about it the way I was trained, which is like, okay, then we're going to meet for coffee and then we're going gonna go on this cultivation process
Rhea Wong (Newsletter/Program Promotion)
and I'm gonna ask you deep, meaningful
Rhea Wong
questions about who you are. So I'm just curious, how do you train people for different types of interaction? Because not everyone is gonna want the coffee and the sit down and that Some of them are just like, just text me. I had one client who raised $3 million from a tech person over a text message.
Amy Eisenstein
Wow.
Rhea Wong
This is not normal. This is not the usual Casey bet.
Amy Eisenstein
Well, I think it's important to first of all not make assumptions about donors and their communication styles and what their needs are. And so part of it is about asking. Right. And so somehow your client found out that this guy really just wanted to text and that's the way he was going to interact and communicate. Certainly that I think is the exception, not the rule. Although certainly with more technology, we're seeing more communication, using technology, less and less in person. And different younger philanthropists, newer philanthropists are going to communicate and want to make decisions in different styles and different ways. And I think the savvy nonprofit fundraiser is going to be open to those methods and models and really open to listening and trying to mirror the communication of each donor if they get fast responses on text. Great, let's do that.
Rhea Wong
Let me ask you this question, because this is a question that I would certainly have if I'm listening to this. I have been thinking about a capital campaign, but honestly, I'm really scared that somehow a capital campaign is going to cannibalize my existing major donor program. So I'm curious, Amy, how do you coach people through that? Because obviously you have organizations that have successfully raised capital campaigns and also have major donors. How do you protect the ask for a capital campaign without jeopardizing the annual gift that you need to keep the lights on?
Amy Eisenstein
We really work with our clients to make sure that they are asking first and foremost, every donor they sit down with, they're talking about the difference between the capital campaign and the annual fund. So how do you articulate what the difference is and the needs are? And say, listen, the capital campaign won't help us if we can't run our regular ongoing programs and services. So we are starting there and we're asking you for a special one time gift, perhaps pledged over multiple years, over and above that, in order to protect the annual fund and make sure that it's not capitalized. Every ask includes both.
Rhea Wong
And so am I hearing that the capital campaign lives and dies by the feasibility study?
Amy Eisenstein
Well, that is our starting place, right? That is where we test the campaign plans, the case for support and assess the goal and find out what they're excited about, if what we're talking about resonates with them, if they want to get engaged, if they'll participate, if they'll support the campaign financially. And so, yes, that is a key component of good, solid campaign planning and preparation and readiness. So I encourage every organization to do a feasibility study, which I have to say is very unfortunately named because people think, you know, is our campaign feasible? It really should have been called a campaign planning or readiness study because then everybody would want to do it. But what a good feasibility study does is it engages donors early. It helps you focus on the right donors, it tests your case for support and gives you real time feedback about how you're talking about your project and your campaign. And it helps you assess your goal. Are you going out with the right amount? Can you raise more? Should you scale back before you go out and just blindly plunge ahead? You have some real data so you can make data driven decisions.
Rhea Wong
Yeah, I love that because it's very akin to what I teach in terms of developing a feedback loop. Because often when we think about major gifts, sometimes the only data point people are looking at is a name and a wealth screen. Well, just because they could give $100,000 doesn't mean that they're going to give $100,000 to you.
Amy Eisenstein
Right.
Rhea Wong
So how are we actually creating a feedback loop to see if are they even interested in us? Like, where do we sit on their priority? Philanthropically, I mean. Yes. Data, data, data. Let me ask you this last question. You can share as much as little as you want, but I'm going to ask you to get a little gossipy without obviously divulging client information. Is there a situation where something just did not work, went disastrous, disastrously awry? And then on the other hand, something that, like, hey, really worked far better than you thought it would.
Amy Eisenstein
Disaster. I'm guessing you're talking about a campaign disaster. Yes. Listen, sometimes projects fall through. So an organization might be planning for a campaign and the city doesn't issue the building permits or the owner of the property decides not to sell it. So there are things that can get in the way of a project that really puts a damper on the campaign and they need to rethink it. Also, leadership transitions can really stall or set a campaign back, but they don't have to stop a campaign. There's plenty of campaigns that we've worked on that survive and even thrive after a leadership change. So does it cause everybody to freak out for a few weeks or a few months? Yes. Do you have to reset with some donors? For sure. But are these insurmountable challenges? No. What really is upsetting to me as a campaign consultant is when people come to us with a stalled campaign, you know, they didn't work with us from the beginning, and they come to us mid campaign and say, what do we do? And they didn't do good planning. They didn't do a feasibility study, and it's much harder to get them over the finish line because the truth is, you know, maybe they can't do what they set out to do because they didn't know, and they just plunged ahead without data and without a real plan. So that's upsetting, too, to the flip side of your question, the most amazing ones are when you see the small, scrappier organizations with a small team and not sure who the donors are at the beginning, do so much planning and put all their heart and soul. And I can think of a small medical facility right now that just surpassed a $5 million goal. And it's tremendous for them. They're in the middle of the country in a small town, and it's amazing. It may not be huge in numbers, millions of dollars, but, you know, when they get to 3 million, 5 million, 7 million, and the whole team is just all heart and soul, and it makes such a huge difference in the community and the organization. Those are the ones that you're like, yes.
Rhea Wong (Newsletter/Program Promotion)
Right.
Rhea Wong
Yeah, I feel that. So working with my clients, what's interesting is inevitably, I always have clients who are like, well, there's not enough money in Philantha State. Right. There's not enough money in West Virginia. There's not enough money in whatever. And when they hit their goals and when they're landing gifts that they didn't even know are possible, it just makes me feel so good. Yes. See, it is possible. With the right strategy and courage.
Amy Eisenstein
Yes.
Rhea Wong
And the right conversations with the right people, amazing things can happen.
Amy Eisenstein
Yeah. I love that.
Rhea Wong
All right, Amy. This has been so fun. I learned so much. If folks are interested in learning more about your work and what you do, where can they go and how can they get more of that Amy Eisenstein in their life?
Amy Eisenstein
We'd love to talk to you on Capital Campaign Pro. Com. They'll find webinars and blog posts and our podcast all about capital campaigns.
Rhea Wong
Yeah, I've actually been on your website. It is chock full of resources, so we'll make sure to put that in the show notes. Amy, thank you so much for stopping.
Amy Eisenstein
Thank you for having me. All right, thanks, Rhea.
Rhea Wong
Bye bye.
Rhea Wong (Newsletter/Program Promotion)
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Date: March 9, 2026
Host: Rhea Wong
Guest: Amy Eisenstein, CEO & Co-founder, Capital Campaign Pro
In this episode, Rhea Wong welcomes back fundraising expert Amy Eisenstein for an in-depth discussion about capital campaigns—those high-impact, once-in-a-while fundraising efforts that can transform nonprofit organizations. The conversation covers everything from defining capital campaigns, assessing readiness, common pitfalls, and strategies for momentum, to practical tips for successful donor engagement and board involvement.
[02:32]
Key Points:
Quote:
“Maybe they should be called capacity campaigns... what makes [them] different from annual fund is that there is usually a big vision for the organization.”
– Amy Eisenstein [02:32]
[04:19]
Amy’s Checklist for Readiness:
Quote:
“If they’re not able to fairly clearly articulate this big vision, I know we have more work to do.”
– Amy Eisenstein [04:19]
[08:39]
Major Red Flags:
Quote:
“If they don’t have a big vision... just to have a cushion or just to endowment, but they don’t really have a vision. That’s an issue.”
– Amy Eisenstein [08:39]
[09:54]
[10:44]
Quote:
“There’s periods of time where there’s more momentum and then there’s slower periods of time... There’s lots of strategies and tactics to regain momentum, re-energize a campaign when it’s in a downturn.”
– Amy Eisenstein [11:13]
[13:54]
[15:34]
Quote:
“...not every board member needs to do the same things. We want every board member making a gift. We want every board member supporting the campaign. But what that means for each person is very different.”
– Amy Eisenstein [16:44]
[19:05]
Quote:
“We have a feasibility study model where we're training and teaching and coaching nonprofit leaders to have interviews with their donors prior to asking for gifts.”
– Amy Eisenstein [19:36]
[21:40]
[22:48]
[24:07]
[26:16]
Quote:
“What really is upsetting to me as a campaign consultant is when people come to us with a stalled campaign... they didn't do a feasibility study, and it's much harder to get them over the finish line because the truth is, you know, maybe they can't do what they set out to do because they didn't know, and they just plunged ahead without data and without a real plan.”
– Amy Eisenstein [26:16]
“You may have some sense of these things and you may not. You may need a consultant or some other expert to help you do some data mining and some wealth screening and some brainstorming with your board.”
– Amy Eisenstein [07:13]
“Major gifts are probably already in your donor base. You’re sitting on a gold mine and you just don’t know it.”
– Rhea Wong [08:17]
“With the right strategy and courage, and the right conversations with the right people, amazing things can happen.”
– Rhea Wong [28:57]
[29:13]
Timestamps of Key Segments
The episode is conversational, candid, and practical—full of real-world examples, analogies, and humor. Amy stresses the importance of planning, data, and genuine relationship-building, while Rhea’s questions surface the anxieties and realities nonprofit leaders face. The dialogue offers both inspiration and grounded advice for anyone considering (or even just curious about) a capital campaign.
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End of summary.