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A
Hey, you, It's Rhea Wong. If you're listening to nonprofit Load on, I'm pretty sure that you'd love my weekly newsletter. Every Tuesday morning, you get updates on the newest podcast episodes. And then interspersed, we have fun special invitations for newsletter subscribers only and fundraising inspo because I know what it feels like to be in the trenches alone. On top of that, you get cute dog photos. Best of all, it is free. So what are you waiting for? Head over to riawong.com now to sign up. Welcome to Nonprofit Lowdown. I'm your host, Rhea Wong. Hey, podcast listeners. Rhea Wong with you once again. So this must be Nonprofit Lowdown. Today, I am excited because I've invited my friend and guest, Kyle Woody. He is the founder of Jax Caregiver Coalition. Among all of the amazing things that Kyle is doing with Jax Caregiver, one of the very interesting things is Kyle cracked the Oprah nut. So we're going to talk about that. But before we get into all of that, Kyle, welcome to the show.
B
Thank you so much, Freya. I'm delighted to be here. I cannot wait to dig in.
A
I am so excited. Okay, before we talk about all of the amazing things that have happened in the last year for you, which has been incredible, tell us a little bit about who you are and what you do. You at Jack's Caregiver Coalition.
B
Yeah. So I serve currently as the executive director. I'm one of three founders. And the origin of the organization starts in 2014 when we were founded. But then it actually, in 2013, I moved to Minnesota from Virginia. And in Virginia is where the moment happened where the coalition was born. That was 2012. My wife was diagnosed with metastatic colon cancer, and we had friends fly across the country to spend a week with us. And Sarah and I had met in California, and that's where our friends came from. And at the dinner table that first night, we were telling them about our plans for their week. And they said, well, that's nice, but we're here to serve you. And they were looking at me and I was puzzled. I don't need help. I'm not sick. Why aren't you serving Sarah? They went on to explain that before they came, they consulted a friend of theirs who had been through a similar thing. And they asked him, how can we show up for this family? And he said, serve the caregiver. They're always forgotten. His name was Jack. He is where the name of the organization comes from. And we exist to bring that message to life. Serve the caregiver. And the thing that has really become more clear to me, even within the last year, is after that happened, we moved to Minnesota because Sarah wanted to live here. We live in the Twin Cities. And five years into that journey, being her caregiver, which at that dinner table, that moment, is when I started to consider, I'm a caregiver. I had never before heard anyone say to me, you're a caregiver. And that started me on a journey of an identity change. We moved to Minnesota five years and into her diagnosis. Initially we're thinking, she'll live to max. Five years later, she asked me for a divorce. And so I had. When you asked me, who am I? I went through an identity change initially in that journey to become a caregiver. And then I fully owned it. I started a nonprofit to help men like me. Moved my wife and my family to a place where she wanted to be, where I knew no one. And then I was asked for a divorce. And that identity was taken from me in many ways. And I'm just so grateful I had the coalition where I could continue to show up as a caregiver for caregivers.
A
That's such a powerful story. I don't think I've ever fully asked you about it, so I'm so glad that you shared it. And the thing that you do, Kyle, that I find so powerful is that you're specifically focusing on men who are caregivers. And I think we're going through a lot of this sort of thing in my family right now. And I'm just really struck by the fact that there aren't a lot of resources out there for caregivers specifically, but, like, almost none for men who are caregivers. And so I'm curious about what are those particular challenges of supporting men who are caregiving.
B
You know, we say all caregivers are invisible. And when I say caregivers, I want to anchor us in non professional, unpaid caregivers. So a cardiologist, one of our clients, actually, he was saying to me, I'm a caregiver, but I give people hugs with scalpels. That's different. And when his wife got sick, he didn't know how to do that. And so I think that's an important thing to differentiate. All caregivers who are unpaid are invisible, but men, I can argue, are the most invisible. Like if. If they're all in the closet, the men are in the jewelry box in the back corner, tucked away, largely even invisible to their own selves. So, like, I was right. I had absolutely no awareness that I was doing something that had a name, that there were other people like me. And that's so much of what we do is really just show up and say, have you thought about you might be a caregiver? And oftentimes they'll say, I'm not. I don't really feel like it's that bad that they kind of minimize it and that I just made a commitment on a spousal situation. It's. It's in sickness and in health. Like, I made a promise. That's. It's not who I am. That's just a promise I made. And. But when we are successful in having them really think about that, almost always they come around to the idea that, yeah, I'm. That I'm a lot of other things too. But then they can start to advocate for themselves at work, for themselves, in their community, in their family, get support, get help. Connect with people who have been there and know and so there specifically. The thing that I think as an organization that we are trying to help men do is ask for and receive support.
A
Yeah.
B
Because as men. Or I can really only speak for myself. I was taught that's not what excellence looks like as a man in this world. It's to figure it out. The chain falls off the bike, you put it back on. You don't go asking your friend Rhea to help you with that. You just get it done. You solve the problem. And in so many of these caregiving journeys, I'm sure you can relate in your own family. There isn't. You can't put the chain back. It's so often an unsolvable problem. And I can speak for myself and so many of our clients, we don't know how to handle that oftentimes as men. I've also met plenty of women who don't either. But it's especially intense when it comes to men.
A
I want to transition over in one second. But I do have one question, because I think a lot of us who are listening can relate. So just for myself in my family, my mother has Parkinson's and my father has been caregiving over the last 13 years. And I can see the toll that it's taking on him. And as someone who cares about him, but I don't live near him, I've made offers to like, how can we help? How can we support? How quick? And it's about like, I'm fine, I'm fine. So how do you help someone who doesn't even want to admit that they need help?
B
Yeah, that is the million dollar question, Ray and I, my heart goes out to you. I'm so sorry to hear about your mother and what she's dealing with. That's. I would argue you're a caregiver as well in that situation. Are you. And this is tricky, right? Like you might not be boots on the ground caregiver, or are you the primary or not? We can get into all these kinds of discussions, but I suspect you care about her. And, and yeah. So the, the question about how to convince your father that he is worthy of his own compassion, that's kind of when I think about the work we've done over the last decade and all the groups I've been to and all of the interactions I've had with these men. They are 100% focused on their purse. They have absolutely no concern for themselves. And that is, I think, a principle most of us can get behind is the golden rule. Do unto others as you would have them do unto you, or love your neighbor as you love yourself. When I was taught that it was 100%, my takeaway from it was love others more than myself. Right. Like, I'm not. I shouldn't be selfish. I should be selfless. And I think when we really analyze that rule, it says love others as we love ourselves. So to the same extent, and that's, that's an approach I've taken that has been effective sometimes is to make the case that actually if you, if you can have more compassion for yourself, more love for yourself, that will number one. That is the golden rule. And we all agree to that, right? That's regardless of religion. I think most people can get behind that. And then I make the case that you'll actually be capable of more love through your own. There's a lot of self care is not a. A new idea, at least to the women in my life, but to a lot of guys, that is. And so it just depends who you're talking to, right? If I'm talking to someone a little more like a car guy, right? Like, what if you took as good a care of yourself as you did that car? The oil changes and the car washes and all that. You need all of that. And seeing in my own story, having years, nine years caring for Sarah, I was lucky to be able to stay on her team after our divorce. My son, after she died, looked at me and said, dad, what happens to me if something happens to you? And I still get emotional when I say that, because it had never occurred to me. Raya.
A
Yeah.
B
That I mattered. My Own health didn't just matter because I'm a person like my kids. My son was basically saying, I'll be an orphan.
A
Yeah.
B
And so, so many of these guys we've seen seven years plus, they didn't even go to the doctor. Like, not a skin check, not a colonoscopy. Their hypertension is through the roof. And we would never sit in judgment of them, especially when we know what they've been through, like, how many times they've been to the hospital. Do you think they want to go back for a treat, anything? No, absolutely not. But that is the. I wish there was a simple answer that could. Was universal and would apply to everyone, but I think so much of it is maybe who do they trust the most? Who do they. Who will they listen to? And then figure, maybe it's your dad's friend maybe getting to him and being like, hey, how could we convince him to have a little more compassion for himself?
A
These issues are so hard, right? Aging and health, and it's just. It's so fraught with so much emotion, and it's hard to. It's hard to know what to do. But speaking of emotion, I want to talk about Oprah, because Oprah is the queen of emotion. So tell me about your Oprah moment. And actually, my number one question is, what did she smell like? No, I was, what was your Oprah moment? Because I think you have lived this moment that everyone talks about, dreams about, and you lived it. So tell me more.
B
I don't remember what she smells like because I don't have a good nose. Our board chair sends me a text and he's. Gene Axius is his name. And he is just this eternal optimist. He. Nothing ever bothers him. He's just genuine, huge hearted, beautiful human being. And he. He sends me this text, like, hey, Oprah. It was a link to her Instagram or one of her Instagram accounts about her book club podcast. And it said, do you have experience caring for a loved one with a terminal illness who did surprising things? And he's like, dude, this is you. You need to email them. Like, of course, Gene. Why didn't I think about emailing Oprah? Like, duh.
A
And honestly, we'll still want you to share this story because this never happens to for anybody except for you. So if you're listening to this, take this with a grain of salt. This is not a strategy, but please continue.
B
It's not. And honestly, I've had more people reach out to me about, how did you do that? Than Anything else that has been the number one question is how did you do that? And the answer really is, don't try. Like, because I didn't. I only emailed because Gene is my boss. I gotta do what my boss says. And I banged out an email and within an hour I had a phone call from a producer. And it's because the story for the book that they picked was my story. And that story was fiction. It was a fictional story about a man. The book is called Some Bright Nowhere. It's the episode is her November of 25 episode and. And his wife asked him to move out. She wanted to be cared for by her friends instead of him. And it's not exactly the same. My wife asked me for a divorce, but close enough. And so that's why they, they chose, chose me as a guest to be a part of that discussion.
A
So you got to come on the podcast with Oprah. You got a picture with Oprah, I'll actually make sure to link it in the show notes for folks who want to see it. What was that like? Let me ask one question at a time. What was it like to meet Oprah? We're all big fans. My life ambition is to be Asian Oprah. So I just want to know, was it everything you ever thought it would be?
B
Many of my friends like nearly fainted when I just told them about the news. And I, of course I admire Oprah. And I think I had more appreciation for Maya Angelou, her, her mentor, her writing and her who she was. And that was what really struck me the most was because at the end of it, we had some one on one time she asked me, so Kyle, what did you learn from this? Can you imagine Oprah looking at you and asking you that question? And all I felt was Maya like her presence, because I knew that's who taught her to ask those kinds of questions. And I just was completely, I was just, I don't know the gravity of, of that who she is and who taught her to show up in the world that way. And, and I had used that, something that Maya taught. When you have a big moment, bring everyone with you who ever loved you. And that's what I did. And so I was terrified. It was a positive anxiety. But I was buoyed up by that message from Maya that everyone who's ever loved me is with me right now. And as far as how it was like to meet her, when she walked in, we were at a Starbucks in New York. There was about 40 people in the audience. She disarmed Everyone immediately, it was like the Beatles when she walked in hysteria. But immediately she just starts joking around with people in the crowd as if she'd known them for a hundred years and just made us all feel important. And it was, yeah, could go on and on, but highly recommend Gran that you, that you go meet her and that you become the Asian version of her. I think you're on your way.
A
I had the Honor of Meeting Dr. Maya Angelou Many, many, many years ago, obviously before she died. And it was a very brief meeting, but it was. You could feel the presence of greatness. I mean, just, it was almost like, like if you've ever seen, like a very ancient wasp elephant, it was that kind of energy. It was just like super grounded, super majestic, incredible. We could go on about these, but we have other things to talk about. So what was the Oprah impact? So obviously it's a huge name, It's a big stage. You were able to talk about this everywhere. What changed in your organization as a result of the Oprah effect?
B
Yeah. So surprisingly, in the short term, very little, as it turns out. We discovered Oprah doesn't. She has a lot of power, but she doesn't have the power to convince men to ask for help in the short term. And, and if you watch the podcast, she actually did a commercial for our organization. She did the voiceover herself because I botched the podcast so badly. And, and I told her afterwards, I was like, I know. And she. That's then. So that's another testament to who she is. But it. So that was in the short term. We were braced for. We get like four clients a month last year. We didn't know was that going to turn into 400 or four dozen or 4 million. By some estimates, there's 16 million of these men in the United States alone. It just didn't change. In November, we saw big spikes on our website and we got opportunities with the press and those types of things, but the demand didn't change. Now, since then, we are currently on track to triple that number in 2026, if that stays the same. But my suspicion is that is not going to stay steady at this pace. I think it's. It's just the credibility that she lends to anything that she advocates for. So we don't know yet what, what that is going to ultimately be. But yeah, it's. It's just. Her name is a magic word. When you use it, doors open. So that's.
A
Yeah, it's like the Good Housekeeping seal of approval. Like if you're Oprah approved like all of a sudden. And actually you and I spoke a little bit about how we can optimize the opportunity. One of the things that you talked about in terms of optimizing the opportunity is you really want to focus now on major gifts. I'm curious, how did you get to that conclusion?
B
A Facebook ad that had Raya talking about major gifts. Because honestly, I had not. I don't think I really had any awareness that that was a thing. To be real candid, I came into this work as someone like so many people do that start nonprofits. I just have so much passion for helping these types of people. And in my former career, I was always just. I was interested in making the sausage, not selling the sausage or talking about it. And. And so to hear your articulating what major gifts means and as a fundraiser focusing on a certain segment of your donors, it just, it fascinated me and I enrolled in the program and I think if anything, I'm only more convinced now after having. I don't know if graduated is the right word, but I'm an alumni. If anything, I'm only more convinced. That is a sound as an executive director, the clarity I have that I know where I need to focus my laser beam is I can't underscore enough how much of a relief that is as. Because we all know any of us who've run. Run an organization as the leader, everyone wants a piece of you and everyone needs something from you. And if you're just running around trying to be everything to everyone, it's a dead end game and sort of have that clarity that I know what emails I need to respond to, I know what events or. And maybe, maybe the. One of the most exciting outcomes for me was divesting from our big fundraising event that we put on every year that would literally. It would take me and our team months to recover from and we'd have all this new blood that came into the organization that we wouldn't ever even really welcome. And so what was the point? And so that feels wonderful too to have let go of. Were there a few people disappointed? Absolutely. Change is hard for people, but I'd do it again. And I'll continue to advocate for you and your team and what you got every night. Nonprofit executive that I know I mentioned this to because I just, I believe in it so much and, and I think so this is my suspicion. You can tell me, Raya. But I think it's just been wisdom that has been held tight to the chest because maybe fundraisers thought out of it. Out of a. Rather than thinking in terms of abundance, it was scarcity. Like if I share these lessons, that means the donors will leave my organization and go somewhere else. And. Yeah, because I'd never heard anyone talk about this before.
A
Yeah, it's so interesting. I think you're right. I think there's some scarcity mindset. But I think the other thing is that I think a lot of people don't have a strategy and so they don't know how to teach other people a strategy. Their strategy is like, make friends with rich people and ask them for money. And I'm like, that's not a strategy, that's a. That's hope. And look, I don't know why everyone is not talking about this. I'm shouting it from the rooftops. And I'm glad you drank the Kool Aid with me because I do think that it is the quickest way to unrestricted revenue. So, last question for me and Kyle, this has been so great and I really appreciate how open hearted you've been and generous you've been. What was it like to work with me and my team? Because I know that there might be some folks out here listening who've thought about working with me, have maybe clicked on the website, taken a look, but they really haven't taken the leap. So what was your experience that might be a way to encourage people to take that next step?
B
Yeah, so, so much of it was refreshing because I'm in a. I'm a community organizer for lonely people. Right. Caregivers, maybe the loneliest people on earth, but someone who's also really lonely. Our executive directors of non profits. And so to find a community of people where it wasn't just having all the wisdom and brilliance of you, Rayya, it was. It was Marvin and it was the. All the other participants and hearing their stories. Hearing what? Or really how I'm not unique at all, really when it comes to the struggles that I'm facing. These are ubiquitous. And. And so I think when I think about what it was like these weekly calls that we had that were on virtual. It just a lot of times I would prepare kind of like, okay, here's what I'm thinking. I want to talk about. I was terrible at ever telling you. You would always want to know, but almost always somebody else would have something that I would be like, no, that's actually more important that I didn't even think about that question. And so I think that gets to the power of community and to. And I think what that does for us is help us feel more confident about asking for help and whether it's from a donor or from a board member or whoever, because we have a greater appreciation for how difficult what we're doing is when we're just doing it every day. We don't kind of lose sight of that. And so we can easily fall into that trap of just going at it alone.
A
It's so interesting how I never really thought about the role of an executive director as that of a caregiver, but you're 100% right. It's a little bit like I toil away, like silently carrying all this burden, expecting that everyone else will benefit except for me. And I might be burning out, but I'm not going to say anything. It's. I'm going to think about that. That's a very interesting frame. And actually, let me ask the follow up question that I think folks are going to want to know. Okay, so we worked with you. You had this great community. We were able to work together. Did it change anything in terms of the bottom line? Did it help you raise more money?
B
Yeah, so I think definitely. It's just we've. What is causing my pause is we've experienced something in the last couple of years as a country, as a, in the, in the whole sector of philanthropy that it's, we can't compare year over year because we've, we've had a, a loss in the last two years in a row. But without a doubt, when I think about. So that's total revenue, right? When I think about cost to raise a dollar, which is what a big idea that I took away from your program, without a doubt, we are light years ahead because again, we divest from these big elaborate experiences that really major donors. I had a major donor say to me once, if you want 2,000 for a table, I'll give you four if I don't have to come. And it's like, wait a minute, you helped me see that, like that's your client and you're selling them something they don't want. And so that I can. And I'm terrible with numbers. I'm more of a feelings person, but I know beyond a shadow of a doubt that our cost to raise a dollar has significantly decreased. And for anyone that's not measuring that, like, if I took away one thing that's important to measure, it's that. And so as long as we can convince more guys to ask for our help, I know that the funding will come because that's where our Donors come.
A
Yeah. Kyle, this has been so awesome and thank you for the nice things that you said about it about me and my team. I mean, I'm very lucky. I have the best team in the world. And it is such a delight to be able to support folks like you doing such incredible and important work in the world. As we sign up. What would be your message to the world? It can be to folks that you want to serve. It could be to folks in the nonprofit sector. Also, if you're listening and you think of a male caregiver who could use the support of Kyle and his team, I'm going to make sure all of the info is in the show notes. So, Kyle, to you, what is the message that you want to put out in the world?
B
You are worthy of your own compassion and this would be a way you could realize that, right? Is giving yourself the support of a team like yours, Raya, that you guys are gonna pour into it as you do, you pour into your clients and their success is yours. And so I think that's an example of a way to be compassionate to yourself is to accept help, seek it out and accept it.
A
Beautiful. Thank you so much, Kyle. Appreciate you being here. And we'll put all of your info in the show notes, plus your picture with Oprah because thank you so much. Hey, fundraisers. Looking to nail those big fundraising asks? Check out my big ask gift program@riawong.com forward slash bag. Say goodbye to uncertainty and hello to confidence with my program. Get expert strategies and personalized support to secure those game changing donations. Don't let fear hold you back. Join me and take your fundraising to new heights. We're enrolling now@riawong.com bag that's riawong.com bag. So if you like big asks and you cannot lie, I'll see you in the program.
Host: Rhea Wong
Guest: Kyle Woody, Executive Director & Co-Founder, Jack’s Caregiver Coalition
Release Date: March 30, 2026
In this episode of Nonprofit Lowdown, host Rhea Wong welcomes Kyle Woody, executive director and co-founder of Jack’s Caregiver Coalition. The conversation dives deep into the seldom-discussed world of male caregivers, Kyle’s personal journey, and the unique hurdles men face in caregiving roles. At the heart of the episode is Kyle’s extraordinary "Oprah moment": the story of how being featured on Oprah’s Book Club podcast reshaped (and, in some surprising ways, didn’t reshape) Jack’s Caregiver Coalition’s impact and outlook. Rhea and Kyle also discuss the real meaning of “the Oprah effect,” nonprofit leadership, and why major gifts are a game-changer for small organizations.
Origin Story (01:24–04:15)
“Serve the caregiver. And the thing that has really become more clear to me, even within the last year, is...I went through an identity change initially in that journey to become a caregiver. And then I fully owned it.” — Kyle (03:12)
Unique Challenges for Male Caregivers (04:50–08:21)
“If they're all in the closet, the men are in the jewelry box in the back corner, tucked away, largely even invisible to their own selves.” — Kyle (05:14)
Barriers to Help (06:55–12:25)
“They are 100% focused on their person. They have absolutely no concern for themselves. ... I think when we really analyze that rule, it says love others as we love ourselves. ... You’ll actually be capable of more love through your own [self-care].” — Kyle (08:43, 09:15)
“My son, after she died, looked at me and said, ‘Dad, what happens to me if something happens to you?’ … It had never occurred to me … that I mattered.” — Kyle (11:22)
How Kyle Landed on Oprah’s Podcast (12:55–15:20)
“The answer really is, don't try. ... I only emailed because Gene is my boss. I gotta do what my boss says.” — Kyle (13:59)
Behind the Scenes with Oprah (14:59–17:18)
“When she walked in ... She disarmed everyone immediately ... just made us all feel important.” — Kyle (16:24)
“When you have a big moment, bring everyone with you who ever loved you. And that's what I did. ... I was buoyed up by that message from Maya [Angelou].” — Kyle (16:08)
Real Impact of the Oprah Effect (18:00–19:43)
“We discovered Oprah ... doesn't have the power to convince men to ask for help in the short term.” — Kyle (18:04)
“Her name is a magic word. When you use it, doors open.” — Kyle (19:39)
Shifting to Major Gifts (19:43–23:15)
“I was interested in making the sausage, not selling the sausage. ... The clarity I have that I know where I need to focus my laser beam ... I can't underscore enough how much of a relief that is.” — Kyle (20:57)
“We divested from our big fundraising event ... and so that feels wonderful too to have let go of.” — Kyle (22:17)
Reflections on Leadership and Community (23:15–26:42)
“I'm a community organizer for lonely people. ... Someone who's also really lonely: executive directors of nonprofits.” — Kyle (24:20)
“It's so interesting how I never really thought about the role of an executive director as that of a caregiver, but you're 100% right.” — Rhea (26:07)
Bottom Line Results from Professional Development (26:42–28:18)
“I had a major donor say to me once, if you want $2,000 for a table, I'll give you $4,000 if I don't have to come. ... You're selling them something they don't want.” — Kyle (27:29)
On Male Caregivers’ Invisibility:
“If they're all in the closet, the men are in the jewelry box in the back corner, tucked away.”
— Kyle (05:14)
On Self-Compassion:
“You are worthy of your own compassion.”
— Kyle (28:56)
On Oprah’s Real Power:
“Her name is a magic word. When you use it, doors open.”
— Kyle (19:39)
On Fundraising Strategy:
“Make friends with rich people and ask them for money. And I'm like, that's not a strategy, that’s hope.”
— Rhea (23:19)
On Community for Nonprofit Leaders:
“Caregivers, maybe the loneliest people on earth, but someone who’s also really lonely: our executive directors of nonprofits.”
— Kyle (24:20)
| Timestamp | Segment Description | |-----------|--------------------------------------------------------------------| | 01:24 | Kyle introduces his journey and founding of Jack’s Caregiver Coalition | | 04:50 | Unique challenges for male caregivers; stigma and lack of recognition| | 06:56 | How to encourage men to ask for/accept help | | 08:21 | Strategies to convince caregivers of their own worthiness | | 12:25 | The lead-in to Kyle’s Oprah experience | | 12:55 | How Kyle landed on Oprah’s Book Club podcast | | 15:20 | What it was like meeting Oprah | | 18:00 | The actual impact of the “Oprah effect” on the organization | | 19:43 | Pivoting to a major gifts fundraising strategy | | 24:19 | Value of community in nonprofit executive coaching | | 26:42 | Hard fundraising outcomes: cost to raise a dollar, donor preference| | 28:56 | Kyle’s parting message: self-compassion |
Kyle’s Message to Caregivers and Sector Leaders:
“You are worthy of your own compassion and this would be a way you could realize that ... giving yourself the support of a team ... accept help, seek it out and accept it.” (28:56)
If you know a male caregiver in need, or are interested in supporting Jack’s Caregiver Coalition, see the episode show notes for resources and contact info.
For nonprofit leaders seeking more effective fundraising and a supportive community, Rhea encourages them to check out her programs—described by Kyle as transformative for the focus, confidence, and cost-effectiveness of nonprofit development work.
Episode Language and Tone:
Supportive, candid, gently humorous, pragmatic, and emotionally intelligent—woven with stories of vulnerability and hard-won nonprofit wisdom.
For listeners new to the episode or the topic, this conversation is a thoughtful invitation to recognize invisible caregivers, rethink tired fundraising tactics, and discover community on the often-lonely path of nonprofit leadership.