76: Surprising Leadership Lessons from Big Bet Philanthropy with Natalie Rekstad

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“Over the arc of my life, as I came into greater and greater financial resources, it grew to look more like the traditional check-cutting variety. And so as a philanthropist, I was a very frustrated philanthropist … I knew I wanted the next chapter be spiritually informed.”

– Natalie Rekstad
Episode #76


In this episode of What the Fundraising Podcast…

We are looking at leadership strengths through a feminine lens on this episode of What the Fundraising with my guest, Natalie Rekstad. As Founder and CEO at Black Fox Philanthropy, Natalie is mobilizing resources in all kinds of innovative ways and – as importantly – makes them open source and welcoming to even the smallest organizations to tap a wealth of wisdom. 

In the process of helping domestic nonprofits and international NGOs build capacities and strengthen their leadership frameworks, Natalie has also gathered tremendous data points on what kinds of qualities define the most highly functional organizations. One of the consistent throughlines, says Natalie, is leaders with a passionate commitment that is not all about themselves. While in the past there has been a lot of deference to charismatic, overtly strong male energy in leadership, we are seeing today a shift in appreciation towards the power of other, more nuanced qualities. Natalie shares a long list of the questions she asks when assessing who is at the helm of an organization and how their most pronounced qualities impact the culture. We also take a deep dive into the power dynamics that can trip up fundraisers, including feeling beholden or disempowered when presenting to funders. It’s about an equal exchange, says Natalie, and understanding that nonprofit teams have something as important as financial resources to bring to the equation. 

If you’d like to learn more about how Black Fox’s trusted advisors deliver fundraising expertise to organizations of all sizes and budgets, you can read their blog, with fascinating articles like this one, “Choreography that Translates into Deeper Relationships and Increased Funding.”


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Natalie and Black Fox


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Get to know Natalie:

Natalie leads a purpose-driven life as the Founder and CEO of Black Fox Philanthropy, a leading fundraising firm serving international NGOs and domestic nonprofits. As a B Corp social enterprise, Black Fox Philanthropy’s mission is to help worthy organizations attract significant and sustainable funding so they can drive deep and lasting social change.


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episode transcript

Mallory Erickson  02:49

Welcome, everyone, I am so excited to be here today with Natalie Rekstad. Natalie, welcome to What The Fundraising.

Natalie Rekstad  02:56

Thank you, Mallory. I’m thrilled to be here. You’re one of my like most beloved friends in the sector. 

Mallory Erickson  03:03

Oh, likewise, I’m really excited for our conversation today. And I know that so many people who are listening to this are familiar with your work and Black Fox Philanthropy, but why don’t you tell everyone a little bit about your journey in the sector? And what brings you to our conversation today?

Natalie Rekstad  03:18

Yeah, sure. So journey to the sector. I actually came at it sideways later in life. It’s a third career. I started out in corporate America 17 years and left in my mid 30s as a VP of Sales and Marketing of the largest woman owned company in Colorado. But I had a strong calling for the impact sector. I founded and ran a nonprofit for 10 years. I bequeath to the Denver Art Museum, and also had my own journey as a philanthropist in the true sense of the word, love of humankind. As an eight year old I started doing fundraising backyard fairs for starving children in Africa after watching a film strip for those of you who are my age, and it was the first time in my life that I realized I didn’t have to sit with heartbreak, the lights go up. And there was this, like, well, now what do we do? We don’t just go to math now. Now what do we do? And I started producing backyard fairs to raise money for NGOs. I didn’t know what they were called at the time. So the philanthropic wiring was already in there. So over the arc of my life as I came into greater and greater financial resources, it grew to look more like the traditional cheque cutting variety. And so as a philanthropist, I was a very frustrated philanthropist. So when I bequeath a nonprofit to the museum, I knew I wanted the next chapter to be spiritually informed, really centered on impact and my strategic brand outperforms my wallet and I knew I could have outsized impact with starting a firm like Black Fox Philanthropy resourcing organizations with the money they need to do their work in the world because fundraising happened to be my zone of genius. 

And so I thought, ah, if I could actually resource them and be capacity building and more, my impact is exponential. So I still have the check writing variety but the theory of impact through Black Fox Philanthropy has definitely proven itself a thousandfold.

Mallory Erickson  05:09

Yeah, it has been really such an honor to get to watch Black Fox explode over the last few years and see the number of organizations that you all get to touch and work with and really just change in so many ways through the funds that you have secured. It’s amazing. 

Natalie Rekstad  05:26

One of the questions is what brought you to this conversation? Two of the clients that we’ve gotten to serve, one the Audacious Prize this year in April. So the conversation being around leadership qualities of becoming big bettable is really timely, because I got to be in Vancouver, I was bursting with so much joy for them as they took the stage and certainly not taking credit. They’re such extraordinary leaders in so many ways. So I’m excited to talk about some of those qualities today. But what an honor to be on the journey alongside so many leaders like this, as well as the early stage folks who are in deep struggle, they didn’t get into these missions, because they’d like to fundraise in fact, many are deer in headlights as you well know. And yet it’s 50% or more of their role in making their organization viable not only in the early stages, but even as they grow to 10 million, 20 million, 40 million, it becomes so central to who they are as leaders in their organization. So we are in a sacred space, I call us the helpers to the real helpers, the behind the scenes resource so that they can do what’s uniquely theirs to do, their zone of genius, which is getting these missions over the finish line. 

Mallory Erickson  06:36

I love that. And I’m curious, why don’t we start with what big bet philanthropy really represents and how you think about it, and how the sector talks about it more broadly.

Natalie Rekstad  06:48

Sure, big bet philanthropy is really centered around $10 million or more investments in an organization that is transformational. I like to talk about bold giving as well, which can be anywhere from $100,000 to a million dollars, whatever is transformational for an organization and the funder themselves to be making such a significant investment. But for the purpose of the call, we can talk about big bet, but I will say the leadership qualities that applies to funders who are thinking about big bet philanthropy and making those incredible investments applies to funders, who are just looking at the exact same leadership qualities, but maybe their stretch gift is 50,000 or 100,000. So I don’t know if the numbers are as material as what are the leadership qualities that sophisticated funders look to, and really seek in terms of making significant funding investments, which can mean different numbers for different funders. But the research that I’ve done over the arc of the last few years was really centered on those big bet funders like MasterCard Foundation, Audacious Prize Co-Impacts, and much more. But again, sophisticated funders are sophisticated and they’re looking at some of those same qualities. So even if you’re a grassroots organization, you’re just starting out, the conversation applies to you as well. What are funders looking for regardless of the dollar amount?

Mallory Erickson  08:17

Yeah, I love that. And I think the reason why thinking about it for me through the lens of big bet is what inspires the funder to stretch? Like what inspires the funder to really double down on an organization and thinking about the leadership qualities that that organization leader inspires is sort of above and beyond investment.

Natalie Rekstad  08:39

100%. And a key ingredient of when they’re making those decisions, is very much to do with what are the leadership qualities of the founder or the co-founder or the leader, the CEO, whomever that may be. And as well, what is the leadership that they’ve surrounded themselves with, in terms of inclusivity, inclusive strength, the strength of the board and the strength of the leadership team as well. So it’s not just looking at the leader themselves, but how are they surrounding themselves with other leaders, they resourced? And it’s funny, because I think a few years ago, we saw a lot of really the charismatic male leaders getting these mega investments. And you see them at the conferences and they know everyone and there’s something so compelling and what the conversations that I began having three or four years ago was a real intentionality around other leadership qualities that were maybe more feminine, maybe more subtle, but just as effective. And so with everything that’s happened over the arc of the last two, three years, it’s been gorgeous, gorgeous to see that actually come to life in terms of real dollars, real investments, in more inclusive looking leaders like women, race and more.

Mallory Erickson  09:59

I’ve loved to hear that, so why don’t we start with what are some of the fundamental, most important leadership qualities of a founder or an organizational leader?

Natalie Rekstad  10:11

Yeah, good question. So it’s interesting because so much of the rubric that big bet funders use is really public facing. When I started doing interviews a few years ago, one set of interviews was commissioned others were more, I want to deepen this among other funders as well, is there’s so many intangibles and that’s where the leadership comes in. That’s not again, not on that public facing rubric. So that was where I was, what’s in between the lines? What are the nuances? What are the subtleties? What’s the intuition? How much does that play a role? And so number of things really rose to the fore commitment, question, humility, questions funders would ask themselves, are they compelling? Do they have the character of a leader? Is there kindness? Do they lead with generosity? Do they come across as ready to make it happen, and have a humility around that, not an arrogance around it, but really that servant leadership quality? One of the things too, I think that really came forward is What’s the origin story? Why is this founder doing this work? I’ve been so fortunate to get to be a judge for fellowships, and more, and the conversations after the interviews are fascinating. Around Ooh, this is really about them building their platform for their ambition, not so much about the mission, caring so deeply. And I think, well, certainly in my case, around my funding women and girls and SDG-5, our deepest passions often spring from our deepest wounds. 

I will stay the course on that mission, hell or high water because it is uniquely mine to do because of my lived experience. And especially as funders are looking at proximate leaders, and these leaders who are serving their own, I just got goosebumps, because I love this topic so much in these extraordinary leaders. So much of what they’re really looking for is that level of ferocity, and conviction, and also character because you can easily get seduced in the space. Shouldn’t say easily, some do get seduced in the space, have they stayed true to the essence of the organization, the mission? And how are they showing up in that with their staff? How is the staff showing up for them? So things along those lines, and obviously expertise, not just expertise in their own mission and their own organization but are they thought leaders in the sector? Are they looking to contribute to the sector, to systems level thinking, to lifting up other organizations while also working in this way? Are they open source? How are they showing up as leaders, as thought partners, to move the entire issue area forward, versus this is mine, behind the podium.

Actually going back to founding Black Fox Philanthropy, I originally thought that I was going to fund leadership for young women, young adults, leaders who are already showing up in their communities really in a strong way but under resourced did more. You can imagine the profile and what I found in all of my due diligence was locally in Colorado, also nationally was, there are so many extraordinary organizations doing this work already with infrastructure, incredible programs, the most inefficient thing I can possibly do is start another one. But what they all had in common was they were in pain around fundraising. And again, that goes back to ah, that happens to be my zone of genius. I need to not be the one behind the podium, not leading the thing but get out of the way so they can do this. I feel a little sheepish because I just shined a light upon the kind of leadership that I would want is are you in this for all the right reasons? Is this basically yours to do in a servant leadership way? Are you leading with generosity. Now you have my attention. Now I want to deepen this, I guess I’m putting my funder head on now, I do want to deepen this conversation and that journey around getting to know them in a very intentional way, and how they surround themselves and how they serve. Again, serving the larger issue area in general. And so many extraordinary leaders I get to work with Sasha Chanoff from Refuge Point, keeps popping to mind. So he would be a great embodiment of someone who is extraordinary expertise, in it for all the right reasons, and is deeply caring about how do we lift all boats and extraordinarily generous in his leadership in that way in the sector, as well as bringing Refuge Point forward in such a powerful way.

Mallory Erickson  14:46

Wow, I really want to just sort of double click on that last part because I have been wondering a lot lately about the expectation or the role of individual Non-Profits with the sector wide responsibility of individual nonprofits. And I said recently, in a speaking event, not planned, it just came off my tongue. I was like we are all stewarding each other’s donors. And so the way we show up whether it’s making connections or without sort of generous spirit or thinking about the problem in the bigger way, I feel like in nonprofit, we can get in that scarcity mindset, this intense tunnel vision, where we actually lose sight of all the things you just said. And so I think hearing that this is what really matters for a foundation to really go above and beyond and see you and want to be a part of something with you. It actually takes you zooming out of that tunnel vision, maybe some precise fierceness around your mission included, of course, but with awareness around the bigger picture, I just think that’s so nice to hear. 

Natalie Rekstad  15:59

Absolutely. And unintentionally, there’s a halo effect to it. Or maybe it is intentional, but really, there’s this, I care so deeply about it. So eventually, and again, when it’s proximate leadership, they feel the pain so deeply. It’s so personal, it’s their own community. They don’t want to keep cards close to the chest, they don’t want to keep solutions tucked away so that they care more about the prize than saving lives or issues we work on are staggering. Our clients work on literally every single one of the 17 SDGs. And yes, they care so deeply about the mission, because it’s part of their DNA to solve this, it’s their sole assignment. If you are clear, this is one of your soul assignments, you are not going to be cards close to the chest, more contracted and controlling, you’re going to lead with generosity, you’re going to lead with how do we make this whole incredible organism healthy, the funders and more as part of that ecosystem and the helpers to the helpers, people like me, people like you who are the connective tissue so that they can do their best work, they can show up with excellence, and get it over the finish line, they need to be resourced. They’re able to do that resource with funding, resource with folks like us capacity building, and more. So it’s all connected. The other thing I will say is, actually, I didn’t even think about this, but it’s popping to mind now. So I’m going to trust it is that these leaders are taking their full space in the room in the meeting in the world, as equals to the funders are coming at it from different angles, clearly. But the value I bring as a leader in solving this, we need each other. And it’s symbiotic and it’s healthy. And to go in as equals really sets the tone. I was at a conference, this was a number of years ago, I spoke in the morning it was a fundraising training. And in the afternoon, there was another fundraising training and I went to participate and cheer on. And the session they had roleplaying where there was nonprofit, people were playing the funder. And they were coached to be arms across their chest, and brick walls and hard. And then the other nonprofit who was trying to get funding as part of the training was trying to get in sideways, and then talking faster and tap dancing faster. And now they’re tap dancing on eggshells, and the funder was just so cold, and I was like, I need to leave, I need to breathe. I was like, in my world, in my network of funders, in my community, there is no one funder who would want to participate at all, in a dynamic like that. And so when nonprofit leaders are going in thinking you’re a funder, you’re up here, I’m down here. So now I have to beg you for money because to your point about scarcity mindset, I don’t want to be in that conversation. But if you come here, I don’t know if this is ours to do together. Let’s find out. But we’re coming in with equal footing, and we’re both taking up our full space in the room exploring is this ours to do together? I don’t know. But if we care so deeply about the same issue, we share the same Northstar. There’s some high alchemy that’s going to take place even if it isn’t the funding. 

So for whatever reason, I felt called to shine the light upon that. I don’t know why maybe because you mentioned scarcity mindset brought me back to a few years ago to that training. So these leaders are also owning their worth in the world in the room. Not in a here I come to save the day but in this, this is me serving, this is me being a servant leader. This is me contributing in deep ways and you have your way of contributing. And let’s see if this is ours to do together. So I wanted to add that in even though it wasn’t something that I had explicitly thought about before, it’s so I don’t think about a lot of things like I don’t think about my hair being fake blonde. It just is and then I have to remember Oh, no, many, many, many fundraisers don’t realise and don’t take their full space in the room and they create dynamics that aren’t leadership. They’re actually the opposite. They’re not taking their full space in the room as the equals that they actually are.

Mallory Erickson  20:01

Okay. I think what you just said, this is why I think you and I have always been kindred spirits and why I love Black Fox so much, because I think that is at the core of so many things, power dynamic that we blame funders for perpetuating. And I think there’s a responsibility for philanthropy to own the history of philanthropy, which often perpetuated that power dynamic. And I think today, as nonprofits, we also need to own the way that we perpetuate that power dynamic. And I don’t think that has happened in the way that it needs to. And I think nonprofits have so much more agency than they realise in renegotiating their relationships with funders and everything you said, I just could not agree with more. And I think that point that you said at the end about like in that moment, where you show up with that scarcity mindset, where you’re begging the funder, where you’ve created this uncomfortable power dynamic that they don’t want to be a part of either what you have actually demonstrated in that is that you are not the leader they want to invest in, I think that is a big lightbulb moment for me in what you said, which is Wow, when we shape shift that way, when we lose our center and our sense of alignment, and we don’t come in with everything we know we offer, we’re sending the opposite message of what we’re trying to do.

Natalie Rekstad  21:26

100 percent. And I’m not going to say that there are gatekeepers on power trips, that unfortunate things happen in the sector, and there are maybe some funders who maybe do approach things in a power dynamic way. And that says so much more about them than it does about you. And are you the one who wants to participate in that or not, like you get to choose to. 

So there are true lived stories of many fundraisers out there who’ve experienced unfortunate things in the past. But again, also going in how much are you taking your space in that meeting, as an equal. Very often I’ll be in a call and I’ll say we have this much time carved out, these are the things I know that I’m bringing to the table to address, what would make this a good use of our time, I don’t say good use of your time. But even the language we choose, we have 45 minutes carved out by the end, what we hope to see happen is x, y and z, what would you need to see happen for this to be a good use of our time. And there’s so many more things. So BlackFox Philanthropy is open source, there’s so much on our website, it’s not sort of here’s a webinar, half marketing, has content, now you have to work with us, we know you can’t afford us, here’s everything we think about and do and pulling back the veil 100%. So there’s a lot of that language in there, leading the donor dance in particular, is setting the stage that sort of upfront contract of we’re equals and you don’t say explicitly, we are equals we’re, but in how you show up in the meeting. And the language that you use, and your presence and more does set the tone. And the funder is going to respond to that with respect, unless they’re not clean in why they’re in there. The original money behind the mission, in many cases is clean. Again, I’ll go back to gatekeepers power trips, I’m not saying these things don’t exist. But even you have influence over what that looks like, based on how you’re showing up.

Mallory Erickson  23:16

I love that. I was thinking recently about when preparing for a donor meeting, for example, how much time we spend on what’s going to be said, all the different people in the meeting are scripting out certain things that different people want to say or and not that I don’t think briefing sheets before meetings with donors and agendas are important, I definitely do. But when we think about the science behind how much of somebody’s experience is based on the words that are said, versus all these other sort of nonverbal cues that I attribute all to the energy that we show up with, which is even if you say the word, our goals, but you are still sitting there feeling that power dynamic exists, that you aren’t sitting there with an offering, they’re going to be able to feel that. And so really just to encourage folks to that this is more than just like hearing that you can switch a word and all of a sudden you’re going to be showing up with all your leadership and all your power. It’s really a set of beliefs and leadership development skills and all of those things. 

Natalie Rekstad  24:17

Yes, 100%. And everything’s energy. And we are so intuitive. And those of us who are in the impact sector, I find really large majority who are highly sensitive to begin with and cannot bear suffering, in large part because we’ve maybe endured a lot of suffering ourselves, we become healers as a result. In our case, we’re looking more on a global scale, but that high sensitivity means that we can read energy really pretty well. So you’re absolutely right. I think it’s only 30% verbal, 70% is nonverbal, like just naming the percentages. That’s my old corporate number many years ago, but I don’t know if that number still stands as being accurate but 30-70 so yeah, how you’re showing up energetically. 100%. You’re absolutely right. The words help.

Mallory Erickson  25:04

Yes. And maybe for people to hear that word and think about that shift ahead of time will help also shift their energy. If you’re showing up with our language instead of your, how does that shift the way that you feel. And I love what you said about sensitivity. And I’m curious actually, maybe to explore that from a leadership perspective, or even how you think about it, and I need to fact check this myself. But someone recently told me that in animal populations, 10% or so of the animal population has a high sensitivity. And the purpose of that in animal populations, especially with herds or groups, when they need to notice a predator is that there will be a whole group of animals grazing or something. But the highly sensitive animals hear the predator way farther away than everybody else in the group. And they alert the herd and they get everybody moved out of the way. And I have been thinking about that so much in terms of nonprofit professionals, too, and sensitivity and intuition and those pieces of what I see in some of the strongest leaders that I’ve witnessed. And so I’m curious about how you think about that, in terms of that more nuanced and visible leadership quality?

Natalie Rekstad  26:19

Oh, I love that question. And I’ve never really thought about it in those terms, it makes first of all that analogy to do with animals make sense. So fact check, let me know because I think it’s true. People who self select into the impact sector, are a unique breed to begin with. What I’ve noticed from the early years, a number of years ago, was in the global space, in particular, it’s really, really hard work. If you’re in there for ego or glory, you get spit out pretty quickly, there’s easier ways to make money, and a lot more money than being in this sector. 

And so I think those of us who really stay in are staying in because it is ours to do. Why is it ours to do, how do we know that? How do we know it’s a soul assignment, to the extent that the level of sacrifice and hard work, and just dark nights of the soul of being in these communities that are in so much suffering and pain and being able to hold that, although we could also talk about the tide of burnout as well. It’s a whole other topic I’m sure you’ve tackled before, Holy smokes. So I do think that high sensitivity, it’s almost a choiceless choice to do what we’re doing. So even though that we’re highly sensitive, and we do burn hot, and therefore burn out, because the stakes are so high, we have no choice but to stay in and see it through. And we have the persistence, the tenacity, the vision, when you’re in the dirt, and you’re marred, what is it? In the arena and you’re just like spitting out your own teeth, and your nose is bloody, you still have your eye on the prize, you do not give up, it would never occurred to you to give up, therefore, you can be highly sensitive, and still see the work through. I was saying this to our team recently, I was like I was not made for these times, I’m too sensitive. And yet, I was made for these times because I’m so sensitive, and I’m strong underneath the sensitivity is a staggering strength and not to shine light upon how I show up in the company. But more, I wonder intuitively, if the funders who are also leaders and have their own hero’s journey, each and every one of them, why they’re in this work, how they’re in this work, make no mistake, they may not be able to be on the front lines, like I’m not able to be on the front lines, but they have their way of showing up. I wonder to what extent there’s a resonance, right, going back to your conversation about energy. It’s like I’m feeling resonant with you, we could just sit in the same room looking at each other and not say a word and I’m feeling that resonance. And relationships are built at the Speed of Trust. And you don’t even necessarily have to say all the right things but there’s a resonance, there’s a trust, there’s a depth of connection. And when there’s that depth of connection, because you’re so in it for all the right reasons. And the other person is in it for all the right reasons. You know, it is yours to do together or you will figure out again, high alchemy, maybe it’s not funding, maybe it’s something else. And in my research with Big Bet Funders, a big conversation was so many of the leaders they ended up funding came to them through their networks because someone will say hey, this person just left my office you absolutely need to talk with her or him. And then the person does and then they make five phone calls. So much of the Big Bet Funding really comes through networks, relationships, trust, depth of connection, so much that goes back to those intangibles that you talked, that you named and kind of I named in the beginning, this isn’t public facing in some rubric. These are the things that are in between spaces where funders are feeling into the relationship and trust. And yes, it’s the expertise of, you know, depth of understanding the subject matter and context and context in the entire sector in the globe, more conviction character, and all of those things matter but I know at the end of the day, if I don’t feel the relationship, feel the trust and Big Bet you’re on a long journey. Do I want to be in relationship over the long haul with this human, with this leadership team? So all of those things that we’re feeling into it without even naming that we’re feeling into it because we do it so naturally, being highly sensitive people. And again, tying back to I think many of us who choose to be in the impact sector are highly sensitive. So maybe it’s not 10% maybe it’s 30, or 40, or maybe even 60%.

Mallory Erickson  30:59

Yeah, wow, I think what you’re speaking to, and really what you said around that trust piece is so huge, and the way that trust is built through many invisible ways that we show up and ultimately connect with each other. And I’ve been thinking a lot about how, when I started fundraising, I was taught that it takes 12 to 18 months to build a major donor relationship, because it takes a long time to build trust. And not that what you said with big bet philanthropy, not that you’re not going to be on a long journey with the funder, but what I was taught was don’t talk about money for that long, just build a friendship for 12 to 18 months, and then you can talk about money. And what it ultimately led to for me was this feeling of inauthenticity in my relationships, because I had this underlying goal that I felt like I wasn’t able to talk about, but I was always kind of thinking about. And so I wasn’t able to just like be seen by the funder and fully see them. And I think once I finally realized that, I could actually start a relationship saying, Hey, I know it’s gonna take us a while to build a relationship and see ultimately, if there is some alchemy here or something for us to do together. But I want to start and try and see and open up those channels and just naming it. And it allowed me to then build trust so much faster, because people knew number one, I was interested like what you were saying in the true, do we want to work together? Is there an our here? And I was really interested in that and interested in knowing if there was and if there wasn’t, and so people could actually feel that which I think just changes the whole conversation. And once I learned that, I remember the day I recieved a $50,000 gift after 30 minutes of a first conversation with a funder and I was like, Whoa, what happened there? And I built trust and rapport. And yes, I had a history of demonstrating impact and expertise, it wasn’t like they had never heard my or my organization’s name. But with those things being there, and then just being really honest and transparent, and focusing on alignment. It just like changed the whole thing.

Natalie Rekstad  33:16

What a beautiful story to illustrate the power of this. And you’re setting the funder free also, they know why they’re in the conversation. Let’s face it, a lot of fundraisers, when they’re starting out early stage career, it’s terrifying to make the ask. Even naming there’s so much and I’m referencing Leading The Donor Dance because we actually give you the tools and the language, including if you are terrified of asking for money, there comes a time you can say this is the part that makes me so uncomfortable, but it’s the most sacred part of my job. So I’m going to take a deep breath and do it anyway. And it’s so interesting how the funder wants to lean in and rescue you like, please don’t be uncomfortable, even just naming the discomfort and asking for money. First of all, the 12 to 18 months, the turnover of fundraising professionals. I heard recently, it’s been accepted as every 18 months, right? They’re getting significant traction, they’re poached, or maybe they haven’t been performing and they need to healthy turnover. So that whole 12 to 18 months is a very dangerous timeline. And we can discern if this is ours to do together in probably two or three conversations, or two or three conversations will discern do we go to that next level of conversation? What does that look like, whatever the next logical outcome is. If it’s 10 million, it’s not going to be over the arc of three meetings in three months, but you can have those conversations of what would it need to look like for you to invest? And typically when you make decisions like this, what timeline and what needs to happen? So basically, they’re going to inform you on what they need to make the decision and the timeline they feel comfortable with. And you can even ask, under what circumstances do you make a stretch gift? It could be 100,000? It would need to look like this, this and this, great I’m doing is and I’m leading with curiosity. What is it in your journey that would make you care so deeply about this mission as deeply as we do about x? Again, with women and girls, when I was on the board of Women’s Foundation of Colorado, I would often say, Look, our deepest passions often spring from our deepest wounds. This is why I care so deeply. And I will share the story of why this is mine to do, which immediately builds trust, I’m not going anywhere, I have not strayed from SDG-5 long before it was even called SDG-5, women and girls. And so that trust can be built so much more quickly, by allowing yourself to be seen and authentic in a responsible, safe way, but holding space for them to tell their story and their journey about why they care so deeply. And again, these all inform the timeline and more, but you’re having a very real, authentic conversation. And that’s more rewarding for everyone, including the funder.

Mallory Erickson  35:58

I love that. Okay, and one more question I want to ask you. So earlier in the conversation, you mentioned what calls us to this work and this choiceless choice we make to stick with it and never give up and really have that tenacity to achieve our mission. And I’ve been thinking about that in terms of the overarching goals for that issue area, we talked a little bit about having your eye on what’s happening in the sector in your issue area versus your specific organization. Because I’ve been thinking about for, I had an organization that I helped build up for five years as the Managing Director, then I became the interim ED. Once I saw what the organization was built on, I really didn’t believe it could be scaled up. And so I thought the best thing to do here is to get it acquired by an organization that had more capacity, it ultimately wasn’t the decision of the board would go with and I left the organization, the organization ended up going bankrupt 18 months later. And then I’ve been thinking a lot about how nonprofits sometimes we stay so overly attached to the failure or success of our particular model or organization versus moving the needle on an issue area. And what it says about our leadership to actually let an organization close or say this isn’t the model or see if your funders are open to a shift. In the startup world, we see it all the time. Startups launch and fail and launch and fail and the founders go on and on. And many of them are committed to solving the overarching problem, but they’re doing it in different models in different ways. And we just don’t see that level of flexibility I don’t think in the nonprofit sector. And I’m curious, when you think about that piece around context and expertise and depth, does that stay true even if it’s been a founder who, for example, has tried something and that wasn’t the thing, tried something else and that wasn’t the thing. Can you just speak to that a little bit?

Natalie Rekstad  37:54

Sure. First, there’s a such thing as founder syndrome. So in your case, the model wasn’t set up to scale. But let’s say it was or we can use another organization as an example. And founders are very often entrepreneurial by nature. They’re not wired to run an organization and yet they’re so attached to maybe the goodies or the ego and it exists and the strokes and the rewards and the magazine articles and all the things that can teach why you got into it in the first place. Or maybe you got into the first place because you wanted those things. And so where do you go from there, as the founder oh, dear. Anyway, I will say with founder syndrome, I think it’s important for a founder to recognize, I have taken it as far as I can go, I am not wired for this. This isn’t my zone of genius. It’s barely my zone of competence. And it also becomes really hard to show up in the work and in a live way. And in a way that’s going to serve the organization’s mission and serve solving the problem. So there comes a point where if the founder is attached to the organization and the structure in unhealthy ways, then if it’s a nonprofit, and there’s a board, there needs to be bravery and making some really thoughtful strategic, intentional and kind, kind to the sector. Right, the northstar question for Black Fox Philanthropy is not what does Natalie need, not what does this team member need? What does the client need? The northstar question is What does Black Fox need? And Mallory candidly, Black Fox does not need to be running Black Fox Philanthropy, I’m wired as an entrepreneur. And so fortunately, just make really smart hires around people who live for operations. But to do with maybe the model isn’t working, hold on tightly let go lightly. It’s not working. And we see better models out there. We see better ways of thinking about it and doing it and my first inclination would be, hey, other founder how did you arrive at that? Can we have a conversation because here I am over here and we’re in struggle. Can we have a really open conversation? And I’m wondering, would we be stronger together or talk to funders. I would see it as an incredible opportunity. This is our edges. These are the edges we’re experiencing. Everyone else is experiencing these edges so I have no one else to look to. But you as a funder, have this pen baglio and work with so many guarantees, when other partners of yours hit this inflection point, what have you seen work? How do you feel about merging with other nonprofit? What have you seen work well, what have you seen not work? Lead with curiosity. Like, I wonder if there’s a better way. You my take all the data, all the information and go, Nope, we’re gonna stay the course. Because whatever your reasons might be, could be clean reasons, because you really have a conviction that it is the best model despite all the evidence, it’s still the best that’s available at the time. But leading with curiosity and humility, and being willing to bring your organization and your leadership into that next level of impact. So it may not look like your brand, and your own me behind the podium. It’s how do we do this in a way that’s actually the Northstar question. How do we solve X? Because if you have that northstar question, what does X need? What does this mission need? What does this country need? It takes you completely out of the conversation, and you can have a real conversation about what is actually needed. And I think it’s hard for us to take ourselves out of the conversation, because we’re the star of our own dramas. So that question pops you out of it. What does this country need right now, and be with other really smart leaders and funders who are leaders and have that conversation, and then take that back to the organization and recalibrate, adapt, including adapting could look like merging or acquiring, or whatever the case may be, I can’t name all the things other than if you lead with curiosity and humility, you’re going to get answers that are far more powerful than what does my organization need? What do I need? If you’re looking at that North Star, what does the country need? What does the mission need? And the mission might need me to get the hell out of the way because I’m an entrepreneur and I’m a disaster at running an organization.

Mallory Erickson  42:15

That is such good advice. Thank you so much. for spending this time today. Tell folks where they can find you and Black Fox.

Natalie Rekstad  42:24

So www.blackfoxphilanthropy.com . And I particularly invite folks to go over to the blog. Again, we’re open source there is so much there, including, oh, maybe link the fundraising handbook, which has so much in there over the arc of the many years that we’ve been open source. And yeah, so BlackFox Philanthropy, we effectively serve as an outsourced development department for many, many organizations, as well as bespoke engagements, funder candidate research, and more. The sector’s most asking of us is to really be sort of that outsourced development model while organizations are in transition or building capacity snf pain around fundraising or ready to go to the next level of impact and need the money to get there. Or maybe somewhere in the middle. And then of course, they have to sign up for everything you do Mallory, because you’re amazing. And I’ve been following you for so many years. And you’re such a great resource for me early on, as well. So much love and respect for you, what you’re doing for the sector and for humanity, and I just love you.

Mallory Erickson  43:26

Oh, thank you, likewise, and everyone should sign up for the Black Fox Newsletter, because it is the best information. That is my go to, so everyone should go there. Thank you so much for this conversation and for your time and just for who you are and how you show up in this sector. I’m so grateful for you. 

Natalie Rekstad  41:02

Thank you. Me too.

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