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broad and deep relationships for fundraising success with Janaiha Bennett

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“Sometimes you have to have the courage to say that you are walking away from a potential supporter because it's not missionly aligned.” - Janaiha Bennett

Broad and Deep Relationships for Fundraising Success with Janaiha Bennett

In today’s episode, we are joined by Janaiha Bennett from Youth Leadership Foundation to teach us how to develop relationships with our donors and how to treat them as humans first than people who would just give you money.


  • How she got into fundraising without being a fundraiser herself

  • The importance of leadership in raising funds

  • Developing a community who share the same vision

Resources Mentioned In This Episode:

Connect with Janaiha:


[00:00:00] Cindy: We all know those generic fundraising activities. The big rubber chicken dinner, or, you know, the emails or mails that we get sent. And sometimes they stack up and they all look and feel the same. There's something generic about fundraising activities that we teach, when we teach fundraising. And I think that adds to a lot of people's feelings of like ickiness around fundraising.

[00:00:29] You know, you swap out a logo and it's all the same. And so today we are going to be talking about how to take some of those, you know, basic fundraising activities or structures and making them really uniquely work for your organization so that they deepen relationships, build community and get your donors saying yes consistently and loving giving to your organization.

[00:01:03] I'm your host, Cindy Wagman. And you're listening to the Small Nonprofit Podcast where we bring you practical down to earth advice on how to get more done for your small organization, because you are going to change the world and we're here to help.

[00:01:21] So with that, my guest today is Janaiha Bennett, who is the Executive Director of Youth Leadership Foundation. Janaiha is passionate about mentorship, the mom of five and a spreadsheet nerd, but she's putting on her fundraising hat today because as an Executive Director, she wears many, many hats, and this is one that you've worked particularly well with grace. So Janaiha, welcome to the podcast.

[00:01:50] Janaiha: Cindy, thank you so much for having me. I'm so excited to have this conversation and I've been looking forward to it all week.

[00:01:56] Cindy: I, same. And like I was looking over our notes and we were talking before. I was like, we could literally have five conversations with you on the podcast, which is what I love about an Executive Director, because you do so many things, but we're gonna talk about fundraising.

[00:02:11] But before we sort of dive into that, tell me a little bit about how you got here, like your role and learning about these things.

[00:02:20] Janaiha: Absolutely. So I love why YLF so I could talk about it all day. Youth Leadership Foundation. So let's start with just my upbringing. I grew up in DC, daughter of an educator, you know, my dad, he was sort of opposed to work.

[00:02:35] In the course of my childhood, I was always exposed to teachers in the educational space and I got to hear their plight a lot. And then just going through my own journey, my middle school journey, which is always kind of fraught as middle school journeys off and on. I got very interested in psychology and so the merging of those two, you know, school spaces and psychology.

[00:02:56] So that led me to a lot of environments that centered around mentorship and individual work with individuals. So I started, working at YLF as a volunteer as a mentor in, when I was in college and I've just sort of stayed with the organization, you know in different capacities, I've seen it sort of up, down, in, out.

[00:03:15] And I've been in this Executive Director role for about four years and it's such a beautiful sort of growth trajectory for me because knowing it so well, knowing the programs from the ground up give me this sort of unique space to be able to share that story with people that wanna support.

[00:03:31] So it's been quite a journey. And I'm, you know I'm still, I'm sure there's still more for me to learn.

[00:03:37] Cindy: I mean, there's more for all of us to learn always. That's the nature of life, but I love that, and I know like, as you described your journey, I know that's gonna resonate so deeply with so many of our listeners who themselves have sort of, you know, moved into leadership roles within organizations.

[00:03:56] I'd love for you to talk a little bit about like how you developed your own skill set. So you weren't a fundraiser.

[00:04:04] Janaiha: Yeah, that's right.

[00:04:05] Cindy: And I mean, I'm sure there's lots of other things that you've had to learn beyond fundraising, but because that's our topic today, how did you sort of learn to step into that? Where did you start to build resources or build your capacity around fundraising? You're pretty successful at it now.

[00:04:25] Janaiha: That is such a great question. I mean, I think that the best tool that you can have in your toolkit is humility and openness to learn from folks. So I, this is why I love what you're doing, Cindy, because, you know, folks can kind of learn online now, you know, they can seek out resources that they need to develop the skills that they don't have. For me, that meant two main types of sort of, you know, acquisition of skills. So I went and I got a certificate in Nonprofit Executive Management at Georgetown, and it was such a great program. And then the other thing is just relying on my board, you know, so I literally, when I first started, I was in the office of our Board President every single week, you know, just talking through things and building that relationship, building that rapport.

[00:05:09] And it just was really helpful, you know? And it's interesting, but if you seek it out, folks are willing to mentor you. Folks are willing to support you. I think that's why I love the nonprofit space because. It's, you know, we are not islands at all. There are definitely some Executive Director colleagues that I can reach out to, we're on listers, we're on threads, we're sharing resources, it's a community.

[00:05:29] So I think that's what it is. It's like relying on the, on the resources that are around you and realizing that you don't have to know it all. And you can lean on people who do.

[00:05:37] Cindy: I love that. I love that. So, Paint me a picture of this fundraising event that you had as an organization that is sort of, you know, a generic fundraising event.

[00:05:52] And this was pre pandemic, right? Like things were the way they were. What was, what did you do? How did you raise money?

[00:06:00] Janaiha: Yeah, so pre pandemic, I think, you know, fair amount of our fundraising was event driven, you know, and they always sort of started small, but then, you know, over the years it sort of gets the flavor that is kind of a little static, you know, like how you, how you experience because they're just their, you know, the tried and true methods that you use.

[00:06:20] And so when the pandemic happened, all that was sort of out of the window. We didn't have the opportunity to run a number of the events that we wanted to, but we could sort of recreate some of the ones that were passion projects, way back in the day back, we had a donor who, you know, found us in a catalog and gave a gift and then started giving through their company.

[00:06:43] And so from that evolved this sort of this, at first, actually it was a softball tournament that was just, you know, within their company. And then that evolved into a race. And I think what made that event so beautiful is that it was really sort of, you know, the drive and the impetus was totally driven by that particular affinity group of DRT Strategies, they've been amazing partners and it's just only grown . So when the pandemic happened, what we found was that, whereas, you know, some of our other events, you know, by necessity, we had to cancel it. The passion behind the DRT event was no, we're gonna go forward with this.

[00:07:18] We're gonna go hybrid with it, not even hybrid. Folks ran virtually. And just the passion that they had for what they were doing and what we are doing as an organization, it gained momentum and it ended up being the most successful 5k we've ever run. Because it was, and it was mostly driven by that community that they said, you know, just kind of demanded , you know, that kinda put this event on and sort of commit to it.

[00:07:44] And so I loved that. I loved that experience. It was so vibrant.

[00:07:48] Cindy: That's fantastic. And you hit on something that I wanna deep dive into a little bit because anytime someone ever asks me about doing a fundraising event, the question is always for me. Who's running it? Because it should not be staff.

[00:08:04] Right. Where's that community of people who are so passionate and so excited to support your organization, that they're going to volunteer all those hours to do an event and that's exactly what you just described. So can you tell me a little bit about like your work in supporting that event in some ways it sounds like it's kind of a third party event, or, you know, someone else is doing all the leg work.

[00:08:28] How do you make sure that those people feel that connection, that you are cultivating the passion that you described?

[00:08:37] Janaiha: You know, in this particular case? It came from leadership. You know, we have a great partner. So the person who originally donated to the event. She's the CEO of a company and she sort of guided sort of her team to learn about it.

[00:08:52] Our job was sort of to continue to cultivate that relationship. And the main way that we did that was by giving the staff there opportunities to meet with our students. Opportunities to meet with our mentors. In particular, we run an event you know, not an event, we run a program every summer called the Virtuous Leadership Academy, essentially what our high school students do in this academy is they have a business plan competition, you know, so they, but with a mind towards service and service, he's like, okay. So if we're doing, if we're doing entrepreneurial work, there should be a social component to it that it helps the betterment of other people.

[00:09:29] DRT Strategies assisted us with that process. You know, they you know, led by the CEO at the time, Susan Kidd, the staff members were contributing. They, they gave talks to the, the students about, you know, business operations. They gave sort of financial strategy perspectives. They critique their business plans.

[00:09:47] And so there was this deep investment, you know, it, wasn't just sort of, they're doing, it wasn't just that they're doing the race or they're raising money. They had a face connection with our mission. And so that sort of drove the passion even higher.

[00:10:01] Cindy: Yeah. I mean, you just, you described basically simultaneously going broad and deep, right?

[00:10:07] So on the one hand you, whether intentional or not at the time, you took a relationship that was with one person and you were able to make it across the organization. So that, eventually, it sounds like, you know, you don't need that one person. We see this a lot with relationships with institutions like corporations or small businesses where the, your one champion leaves and everything is the money stops.

[00:10:37] But what you've done is say, okay, no, like everyone in the, in that company is going to is important. We wanna build broader relationships. And deeper ones and we wanna really help them connect with the mission, as you said, that FaceTime so that they care deeply. And that combination is bulletproof.

[00:11:00] Like they're gonna, they're gonna keep giving for a long time. So I love that.

[00:11:05] Janaiha: Exactly. No. And you said it right. You know, it's, it's both breath and depth, you know, and I think that a lot of the struggle with some folks is that they want relationships to kind of stay static. But it's just sort of allowing, you know, the relationship to evolve, you know, so it started as just sort of an individual giver.

[00:11:25] You know, our usual approach for individual givers is a little different. It's like, we're, you know, we're asking them to make bigger and bigger financial commitments, but being able to sort of like be creative in how you approach a person and let the relationship really season and marinate and become something different, you know?

[00:11:42] And that 's a feedback loop, you know, that happens cause of a conversation. You know, our event with, with DRT Strategies, wasn't always a 5k. It started off as sort of a softball tournament and that was fun, but it ran its course and we had to allow that change to happen. That can be kind of scary because you know, sometimes you feel reliant.

[00:12:01] You wanna sort of keep every gift as it was, you know, and not sort of, you know, let change happen or take the risk of doing something different. But I tell you, when you, when you lean into folks' passions, when you sort of are able to get that feedback, it happens way more naturally.

[00:12:16] Cindy: Mm. Yeah. Like you, you recognize them as a whole person, as opposed to just like they're in the individual giving bucket which is so, so fantastic. Like very often. Yeah. We think of them as like, this is the one vehicle, like you're we segment, we bucket people out and we forget that they're actually much more wholesome than that.

[00:12:39] You talk a lot about, and when we've talked previously, like going really leaning into the mission for that event or really all the work that you're doing. So like looking at individuals as whole individuals as deeply connected, and then even continuing to take that further and really making it about the mission, right? Like really the intersection between the mission and those people who are participating, how have you been able to like through the event even make it really stand out as something that feels great for people because it is about the mission. I mean, you said a 5k is a 5k, like, right. There's nothing unique or special about running a 5k. So how have you brought that mission into it so that you are deepening those connections?

[00:13:32] Janaiha: This is such a great question. And it's a question of reflection that we had just in response to, you know, we had this hybrid event.

[00:13:39] And what we found last year is that folks still wanted to run virtually. So it's like, all right, well, what do we do? Cause we ended up not even having as many folks that ran in person for our last year's event that then ran virtually. So we had to sit and do some reflection. Well, how do we make this sort of, you know, not what it was, but sort of really sort of drive that community passion?

[00:14:00] And so we, we came up with a lot of ideas. So it's always the case that some of our students run, but we, and we have sort of a little award ceremony after where we sort of honor the people who participated and just maybe have like a little meal and sharing time. What we decided to do this year was to make it a community event, in fact, you know, so we're gonna have a couple food trucks out. We're gonna have, you know, a music performers. We're gonna have backpack giveaways, you know, and, and make it really sort of a community driven event that even if you aren't racing, it's a place to gather. And with that, so if you are racing, you know, you don't, you've never been exposed to YLF before, but then you come to this community event and you get to actually see some of the families that we serve.

[00:14:46] Well, then that sort of, it deepens you, you get a real in direct sense of like who it is. You, you spent your spent your time, you know, how did you, you spent your time in your effort to come out and run this morning, but now you there's a community event and you get to see the faces that it benefits. And that, you know, it, it just a double whammy, you know? Yeah. And it means something for those families too. You know, many of our families run as well, and that's a sort of empowering experience too, where they're giving back to the program that's serving their kids all year as well, you know?

[00:15:18] Cindy: Yeah. Like literally everything you say I feel like we could have a whole conversation around. I want to talk about this idea of bringing everyone together because very often in organizations, what I've seen is either like we treat our donors are over here on one side and our, you know, organization and our communities on the other side and they don't interact.

[00:15:40] And, you know, on the extreme side of this, I just wrote an email about this, but you know, there are organizations where they might have like a facility tour or something like that, where they have to make sure I've done work with a youth shelter before where the donors will come in. They'll give a tour, they'll get a tour of the youth shelter, but they make sure all the youth are out for the day because otherwise there's a weird power dynamic.

[00:16:07] Like literally they've had to organize, they've had donors wanna give directly to specific individuals and like, that sort of reinforces that separation of, you know, the haves and the have nots. And I'm using air quotes where we think where we've set up this unhealthy dynamic. And what you're talking about is actually like we're all community, right.

[00:16:30] I can't stand when people say our community and I've just did this two seconds ago when talking about our community and our donors, like they're not the same thing. So tell me a little bit about that bringing people together and what that's been like for both groups and how, yeah, how that works because very often organizations.

[00:16:53] Janaiha: Right. And I'll have to say that, you know, there are many situations in which you do wanna sort of respect the privacy of, you know, not, not every nonprofit is the same. And so, you know, sometimes you have to be very sensitive about client populations and you wanna be very thoughtful about that.

[00:17:08] I know, you know, an Executive Director colleague that works, you know, at a sort of a center for women who who've gone through sort of domestic violence and that kind of thing. And you wanna be very sensitive to those issues. We are in a unique position at YLF that we serve youth and families. And most of those families aren't in crisis.

[00:17:25] It's sort of. We like to sort of describe some of our kids as the forgotten middle you know, that they're not they're not the kids that are getting like, you know, flying color grades, and they're not the kids that are, abjectly like struggling in school, but they're sort of the, the middle that just kind of need that push, you know?

[00:17:40] And so I think that gives us a lot of opportunities. I think the way that we cultivate it. It's by very being very centered and, and clear about what it is we're doing such that the folks that support us are support us, supporting us across the gamut, and they want to be sort of invested and involved and the same thing that, that the line sort of, they there's a lot of crossover.

[00:18:04] I'll give you sort of a few examples of what I mean, many of the folks that support financially have have children of their own, that end up sort of either coming in the program or supporting as mentors in the program, you know, oftentimes this, the, there are students that. Are connected or it is sort of almost like a, becomes a network of exchange where students that have come through our program.

[00:18:32] Well, now they have this networking community that gets them, you know, some kind of I'll give you a good example, sorry, because this is too vague. So there's a student who went all the way through the program. Third, third grade and up, we ended up being colleagues together, cuz he worked on staff as the tap director while I was the college director. All throughout his high school career, he'd gone to a private school through a scholarship that, in that the institution of that scholarship came because of a connection with a supporter. Wow, this, this, this tap director now works at a tech firm. And now he's sort of giving back in a different way. he donates to the 5k, you know, he donates to that same scholarship fund that was instituted.

[00:19:15] Based on the relationship. And so all the, all the, all these relationships are mutually reinforcing and, and they cascade, it's like a snowball effect. And I think it's very difficult to know how that comes about, but what I will say is that you can't. You can't do double speak. You can't try to speak to one audience one way and one audience, another, you have to know yourself, be true to yourself and communicate those things clearly to the people that support you and trust that the people we're gonna give are gonna give, because they believe in what you're saying.

[00:19:48] And that's difficult to do. You know? Mission creep. Donor creep is a real thing. You know, there's a pressure to get to that yes. Sometimes you have to have the courage to say that you are walking away from a potential supporter because they're it's not, missionly aligned, you know?

[00:20:03] Cindy: Yeah. Yeah. Oh, so, so important to have these conversations. But I think that, again, it it's comes back to that wholesome, like people are complex and dynamic and, you know, connect in so many different ways. And so when someone goes from, you know, maybe being in the program to then being a sponsor and, you know, all or like a donor and then their kids eventually might, might come into the programs, like understanding that those are dynamic relationships.

[00:20:37] Which leads me to sort of, we we're writing outta time, but I wanna talk about that idea of these dynamic relationships and really like getting to know people well, cuz one of the things you and I have talked about before is getting to a point with your supporters where you know them well enough that you're asking.

[00:21:01] You're getting yeses. Right? So, so often in fundraising, we hear, you know, you have to get no's to get yeses, right? You're for every yes, you get, you're gonna get this many no's like that. It's just part of fundraising, which it is. But at the same time, we can build relationships to get to a point where we can ask and ask and ask and ask and get yes.

[00:21:26] Yes, yes, yes. But it takes time. So tell me about your experience with that and really getting to know your supporters so that you can sort of continue to grow their support?

[00:21:39] Janaiha: Yeah, absolutely. This is a great question. So I think the trick that, you know, that, that I sort of employ is putting fundraising aside for a second, you know, and just sort of saying I'm why am I meeting this person?

[00:21:55] You know, this person is primarily a person . And just trying to remember that, you know, before I sort of, I'm really sort of gung-ho about whatever campaign I'm doing. I think people, since when you are just meeting with them to ask for money or just calling to ask for money and so I think, I think part of the issue is, you know, when you're calling a, a supporter or even for that matter of, you know, a parent or anyone just being open to whatever will emerge from the conversation and aim to have a good conversation first and, and the yeses come from that because sometimes the yes is, yeah, let's have lunch.

[00:22:33] You know and then the, sometimes the yes is, oh, you know, I know, I know a friend who's talking just about just what you're doing, why don't we set up a get together where, you know, you can see his, his facility, his, you know his rock climbing company or whatever it is, you know, and, and the yeses come iteratively.

[00:22:51] And then before, you know, it, they're they're more saying, how can I support and it's and you are the person who's saying, yes, there are many ways that you can support, you know, I mean, trying to flip that on its head and sort of lead with, with humanity first and then see what to see what happens. And it's a bit chaotic, you know, you can't put that on a tracker but yeah, I think you have to sort of get into a position of stability.

[00:23:16] Where you're sort of, you've, you've kind of balanced Your revenue with what your program aims are, and you're not sort of pinched so that you can kind of, you can, you can raise in a relaxed posture, you know.

[00:23:28] Cindy: Yeah. And I think, I mean, I always teach to me the number one quality of a great fundraiser is curiosity. Yes. Right. It's learning, getting to know people. And so much of what you described is not, is getting to know all people and bringing people together and building community and seeing how that deepens those relationships as well, which. I'm gonna kind of circle back to one of the early things we said, which is about flip.

[00:23:58] So we talked about with the company, having one relationship with the founder, or, you know, head of the company and broadening and deepening that across the corporation or business. Yeah. But you also on the other side of this and I think is equally important, it sounds like you've also deepened donor relationships broaden and deepen them within your organization. So we see so often, you know, the Executive Director holds all the relationships with the donors, right? They're the only person in the organization. Donors, no one interact with. And that interaction can be quite shallow. And what you've talked about is say no, like, you're gonna interact with all of us and our community and you are our community. And so you broaden and deepen that side of the relationship as well, which I think is equally important. And now you've created a web that's really hard to disentangle. Yeah. And really creates lifelong supporters. So Congratulations.