About This Episode

In this episode, Caroline Whistler, CEO of Third Sector, discusses how her organization helps nonprofits and government agencies redesign contracts around outcomes instead of services alone. She traces her own path from a privileged upbringing to recognizing systemic gaps, and explains how mapping who actually controls funding decisions can help a nonprofit build lasting relationships with public sector partners over time.

Listeners will take away a strategic approach to government relationships, including why positioning as a thought partner rather than a vendor changes negotiating power. Caroline also shares candid thoughts on using AI responsibly in nonprofit operations, why active curiosity matters as the technology continues to evolve, and how she navigates uncertainty in the sector today.

More on how nonprofit teams keep supporters and staff connected

FRANSiS builds AI Powered Helper messaging for mission driven teams. If this conversation resonated, these resources go deeper:

[0:00] Introduction & Caroline's Journey from Privilege to Purpose

[6:11] Why Government Funds Services Over Outcomes

[9:08] Rewriting Contracts That Transform Lives

[11:55] Building Third Sector: 14 Years of Systems Change

[15:03] Navigating Uncertainty in the Nonprofit Sector

[18:38] Strategic Relationship Building with Government Partners

[24:10] AI and Automation in Nonprofit Operations

[28:16] Real World Example: Workforce Development in Rural Texas

[32:27] First Steps for Nonprofit Leaders in 2025

[35:04] The Advice That Changed Everything

[36:20] Blind Question: Erasing Cost Reimbursement Funding

Episode Transcript

[0:16]  Welcome back to another episode here on the Heart and Hustle Podcast. Our next guest says, "I realize the system worked for me because it was built for me." Is that correct, Caroline?

[0:26]  That is correct. So, so, so I ask you, you had a front row seat to privilege. When did the blinders come off?

[0:33]  Yeah. So, um, front row seat to privilege. For me, that looked like growing up with both parents in a, uh, in a white suburb in the Northeast, um, with everything that I needed, food, shelter, all those things. Um when I was three years old, I was fortunate to move to London with my parents where I was exposed to so many folks speaking different languages, so many folks um in different types of housing. And I think at that point it was just that's what it was. And then it was when we moved back to the United States and in Rhode Island to another kind of leafy green white suburb in a big house that I went whoa like what do you mean not everybody lives in you know small apartments like in London and what do you mean that these are the resources that that we have? Uh, and so that was I think first a change in my physical environment that I realized, oh, and we're going to the public school cuz it is a great public school in my town, but not everybody has that opportunity where they live. Um, so that was one of the things that was a real visceral eye openener for me when I changed my geographic location.

[1:47]  I wish that more people had the ability to actually travel and see the world at that scale, right? because I it takes me back to um just recently probably the last three four years I worked for the airline industry and I mean where I grew up pretty rough right they call it crime hills um not a lot of people probably make it out of that community and mostly black Hispanic neighborhood that's kind of where I grew up you know grew up in and um all we knew was our backyards so for me early on I was able to see San Francisco that was like oh my god there's something greater than that um but then what happened was recently I went to South Africa for 3 weeks. So when you talk about really living differently, right, even living in Pine Hills was better than living in South Africa where for 4 hours a day, they have no electricity. So when I'm teaching them, it's like 400 p.m. to 12:00. I have to go to the restroom with the light of my my flashlight on to go to the bathroom. But these people are still grateful. They're still telling each other to be quiet. They're just thankful that I'm there because they have an opportunity to work. That's how that's how they look at it. like you're giving us an opportunity to just get out of our zone and what we've been doing here. And um that made me realize like or even water, something as simple as water. Every day I drink a bottle of water. I mean more than one bottle, but I would bring in this big bottle of water. And then I had a gentleman says, "Ephrain, why do you always come with a brand new bottle of water?" And I'm like, "What do you mean, bro? Don't you drink water? I see you drinking water every day, too." He says, "I have to fill up my water with tap water and put into the fridge to make it feel like we're drinking cold water." And it's like when you see that, you realize like, yeah, there there is so much more to the world than what we actually have. Um, and and people don't get to see that. So, I'm happy that you got to experience that and that I got to experience that cuz we bring these memories and we bring these conversations back to humanity here in in America and hope that people can stop living so ungrateful at times. Is am I am I sitting here saying anything wrong, Caroline?

[3:42]  No, I mean, I hear it. It's that's such a beautiful example both of like the gratitude that you can have when for small things and big things but also what you shared just about the no electricity in the evenings like

[3:57]  that's a little bit of the system right like that's a systemic choice that that community that government decided to shut off the electricity and that hits you know it inconvenienced you going to the bathroom but imagine folks who like needed to cook needed to study, read, like the the kind of talk about the system not being built for you, right?

[4:20]  They couldn't charge a cell phone. Just imagine, Caroline, how would we live without a cell phone? Like,

[4:24]  no.

[4:25]  So, I could not

[4:27]  not at all. During the uh last year during the hurricane, because I'm in Florida during the hurricane, I was out with internet for four days and my life was like, "Oh my god, what do I supposed to be doing? Like, I can't watch TV streaming services." Like, so no, I love it that you you've seen that very early on, though. And I can only imagine that it was very frustrating early on as well. Is it because you seeing because you were seeing great work go unnoticed? Is that what made you um maybe frustrated early on?

[4:53]  So I would say after I moved back to that Leafy Green neighborhood um I spent a lot of time trying to find get out of that neighborhood and see what the world was really like. And I think I got really frustrated when I started working at a Boys and Girls Club in downtown Providence. And I was working with kids who had just been at the full school day and they were coming to an afterchool program and they were starving. They were really hungry. They were falling asleep. They were exhausted. And I was like, "Wait a minute. This should be fun. This should be like after school. This should be a place where you're coming. You're playing games. Like, I'm here to teach you to learn how to swim, you know, all these cool things." And these poor kids are just like so exhausted by their day, the system. they're hungry and I was like, "This isn't fair." Like, why can't kids be kids, right? Like, what is going on with the way that they're able to be supported and nourished that they can't, you know, have fun in the pool or on the basketball court. Um, and that's what made me really start to think about like, wait a minute, like what's going on in these schools anyway or like where is all of our, you know, taxpayer money going and is it really um making a difference in the lives of those who need it most?

[6:11]  And as you mentioned, there's a trillion dollars on the table and it's possibly going to the wrong folks, right? So talk about it. Why is government still funding services over outcomes?

[6:22]  Yeah. So with that frustration um I started on a journey to explore like well where where is all this money and what what's it going towards and you're right there's over a trillion dollars at the state local level and really the goal of government is to spend our taxpayer dollars delivering services that are responsive and make a difference in our lives. Too often though, what that actually looks like in terms of the incentives for governments is just you get your budget, did you spend your budget? And so there's a real pressure to kind of get the dollars out the door and to do it in a way that um is sort of legally sound. And so I realized that a lot of times when folks when they're doing contracts for nonprofits at the government level, it's all very based on services or inputs like what how many, you know, pencils are you going to spend for the tutoring program, how many books are you going to buy versus are kids going to learn math and reading. Um and so I think that's really the the difference um is kind of a mindset that okay, we've got to be compliant. the best use way to spend taxpayer dollars is to be compliant and to make sure we know exactly what we spent the money on versus a mindset that says the best way to spend taxpayer dollars is delivering responsive services that measurably measurably improve people's lives. Um, and we do a lot of the former in our state and local governments. Great intent, but when the money goes out the door, it's for inputs or activities and not about like

[7:54]  which programs are actually making a difference for folks. And so that's why I ended up starting Third Sector.

[8:01]  So you started this, you're helping uh nonprofits stop chasing crumbs and and really start shaping the system. How are you doing it?

[8:09]  So we actually partner mostly at the at the government level. So with state and local governments who are one of the biggest funders of nonprofit services and nonprofit providers and we help them understand this difference. We help them understand like what would it look like if you stopped caring so much about how many pencils and chairs and books and you started caring more about the improvements in math scores or the improvements in reading scores. Who would you need to talk to differently in order to make that a reality? Which nonprofits would you be in conversation with to set those outcome goals? And then how might you restructure your RFPs and your contracting so those nonprofits that are delivering measurable results can actually start to get a greater share of the public funding that's out there. So um so yeah so we work mostly with government folks and with the service providers that are contracting a lot with government to really shift the relationship to focus on um what again what is the northstar that you care about the improvement in people's lives that you care about and where are those nonprofits actually delivering that um so you can start to fund you know reallocate some more resources towards those. You mentioned RFP. Um do you remember one that you had to rewrite that you're probably proud of that really changed lives?

[9:29]  Yeah. So one um example that comes to mind for me is a program that we did in Oregon. Uh it was called Sponsors Inc. And this was um a contract that we helped write with the nonprofit was called Sponsors and the leading um re-entry county re-entry agency. And we helped them to rewrite a contract that was based on outcomes for um those who are returning from incarceration. And the outcome was around increasing supportive housing for those returning from incarceration. And so that was like the outcome goal in the contract. everyone was laser focused on it. Um the other goal was to reduce recidivism for this group. Um which is something the government also cares a lot about. And the result of that was um so we helped rewrite that contract. We broke down the silos between the housing authority and the criminal legal system. And the result was that this great nonprofit sponsors was finally like freed up to do what they do best, which is to house people who are returning from incarceration and to um keep them engaged and out of prison. And so the results of that project so far, um 87% of the participants have been stably housed, which is great regarding, you know, compared to the baseline, which is most folks would still be homeless or housing and stable. And then the programs reduced recidivism by over 60%. Which is just like tremendous. And again, this is a nonprofit that was basically allowed the flexibility that still accountable for that outcome goal, right? But allowed the flexibility to do what it takes for those folks um in order to make a measurable difference. So I would say that is a successful contract. Yeah, we're proud of that one.

[11:20]  Hey, real quick. Have you enjoying the podcast? We first want to say thank you and we also just want to give you a little insight of what we're up to at Francis. Some don't even realize that we're working with organizations to help them use AI to create that real human communication experiences where that's actually supporting your your families, those patients or the entire community. We're actually creating tech that connects. Check it out. Francis.ai. How long have you been doing this? I know you said you started this. How many years has it been now? Gosh, it's been about 14 years since we've started. Yeah.

[11:55]  Really? How how big have you been able to grow this from nothing to 14 years later?

[12:00]  Yeah. So, we're a nonprofit ourselves and um what started with me and my co-founder and we are now 55 folks uh across the country. So, we're fully remote uh in 20 states.

[12:12]  How cool is that? When it was just a vision, just not even just a Yeah. an experience really, right? what your mom taking you from one place or your parents taking you from one place to other that experience allows us to kind of live a life that we've never expected. That's what I love about life so much is the experiences that we have really shape us. Uh and recently I was I was having a conversation I was asking is a leader born or life does life experiences create that leader? And I really think that maybe you had life experiences that really shaped the leader you are today. Like to think where you were, an idea, a vision, and you put uh foot on the ground and and never looked back 14 years later. But I can imagine there were some challenges, right, Caroline? I don't want people to sit here and look at it like, "Oh my god, 14 years she's a success." That's not true. Challenges. You've experienced any. You remember those that you can go back to?

[13:01]  Yeah. Oh gosh. I think um one of the biggest challenges I faced was even before I started the organization again this is me being a well-intentioned privileged person trying to help um I went to college and I thought I was going to go help folks in South Africa right folks in the developing world I ended up in Brazil in northeast Brazil myself and one of the biggest challenges I have I would say like a loving challenge was I came I was all excited to apply what I had learned in the classroom And I had all these good intentions. And the wonderful folks in the community that I was in said, you know, girl, why don't you just sit down? We love your energy. You can't speak Portuguese. They speak Portuguese and like, you can't speak Portuguese very well at all. We love that you're here. How about you sit down and listen because we've got some ideas of how we think we can best improve our community. And that challenge and that lesson was just instrumental for me in terms of how I approach everything we do at third sector is that you know I um again have been like gifted power privilege because of my identity and the resources my family had but

[14:11]  for those who our government is trying to help the most who have less opportunity you know what those people have a pretty good idea of what it's going to take in order for them to improve their lives. And so one of the best things that we do at Third Sector or we encourage our governments to do at Third Sector is to listen and to really co-define and and co-develop what those outcomes, what those responsive services are going to be to actually like help people thrive and improve their lives. So that was that was one challenge for sure um along along the way. No, I I what I really appreciate is that you continue to mention I had the privileged life, but that doesn't mean you had to go do the work that you're doing. So that that's actually kudos to you, right? Because I believe we all have a path in our lives. Those that have had to overcome adversity like myself, I chose the path to not repeat cycles, but how do we continue to educate uh provide resources to others to know that if it's sexual abuse, if is adoptions, like all these nonprofits that you work with, they have a mission. And usually that's it's how do we impact youth? How do we impact our communities? How do you know? So to know that yes, you are privileged, but you're utilizing this for the better. I love this. I truly truly do. And I can imagine that in a space right now where we're seeing nonprofits um almost living in fear because they don't have the ability, the resources, the knowledge, right, the privilege of whatever that if you want to call it that. what what are some of the things that you're seeing them navigate some of these strategic ways are navigating through this climate change?

[15:44]  Yeah. Uh well, first I just want to say like it is really tough times out there. It's unprecedented times. Um

[15:54]  that world word feels overused right now um in the system. So, um, and to be in the nonprofit space and so, um, just want to acknowledge that it is really hard and for those nonprofits who are out there and kind of wondering where to turn, there's so much uncertainty. I think fear is a good word for it. Uncertainty definitely. Um, you know, one of the things we're seeing some of our strongest nonprofit leaders do is to really take a step back and try to start by understanding, you know, for whether you care about youth development, economic mobility, homelessness. Start by really doing a little bit of that landscape mapping and trying to understand for your community and for the group, the people that you care about improving their lives who sets the priorities and who manages the money in your issue area and that and truly it is not like oh it's all the federal government for everything. No, truly like depending for homelessness it could be at the city at the housing authority or at the county level. Other times it could be a state agency or a department that has a specific mandate. So doing a little bit of we've got our savviest folks are doing some mapping around like wait who who's incentivized to care about the people we care about. Where is where is the money? Follow the money a little bit.

[17:18]  And then once you identify who those leaders are and spoiler alert like it's not the mayor. It's not the mayor. Like everybody wants to go talk to the mayor but it's like it's the dip. It's the deputy. It's somebody who's running. It's somebody whose name you probably haven't heard of, that isn't on the front page of the news, who's actually controlling hundreds of millions of dollars in resources for the um for the causes that you care about. And so figure out who those leaders are, reach out with a clear message, talk about the outcomes that you're trying to achieve and how your work aligns with the problems that those individuals are trying to solve. Um and really the goal again our most savvy nonprofit partners they're trying to become a thought partner with those who control the resources in the public sector and not just a grantee. So if you come and you're like, "Hey, we get, you know, return on investment of 10 to one. You should give us all your money." Like, you know, government folks get 10 of those conversations a day. But if you come saying like, "Hey, you know, we're going to see reductions, you know, across the board in our funding. How can we think about organizing our community and our resources together to make sure we deliver responsive services for the homeless population?" That's like, you're a thought partner. You're not asking for you're not just asking to be a grantee. You're dropping gems right there, Caroline. Yeah, that's gems. You got to be a thought partner because everybody's asking for money, right? We're in the asking businesses nonprofit. So, I love that you kind of brought that. You got to be a little bit smarter than that. All right. I'm just out here be asking, building relationships. Yes.

[18:49]  Um I actually spoke to a leader that mentioned he took over organization, started they were making 70 million or $80 million a year. Now they're making $400 million a year. And he says uh and some of the gems that he dropped was as you mentioned, I was building relationships. I was I was going to chamber meetings. I was, you know, investing like, yeah, it does cost to be part of a chamber, but let's be honest, what is the ROI when you're seeing all these different leaders that you're mentioning at all these different events? Um, building your your board with other leaders as well, you know, not just people filling up a seat. Um, not just, you know, for me instance, I have a I I I'm the president of my old high school's foundation, right? And, um, I love it. there's great moms on the board and there's those, you know, excited people, but we need leaders that are truly, as you mentioned, are making differences in their specific places that also bring value. So, let's talk to the accountant. Let's talk to the marketing director knowing that that's what we need. Why are we not partnering up strategically in that space? Instead, we're just kind of getting anybody and everybody. I think that's also a strategic play is making sure your board has value because that's what's going to support you to to kind of scale up. And now I think AI is just as great. You know, I'm I'm I wish I would have started earlier to be quite frank. My friend told me about AI 3 years ago. I surpassed him when it comes to AI and he's like, I should have what what happened? But I'm a big believer that um automation doing the things more of what we love, which is showing up on the front lines and how do we automate all the things on the back back end? Do you also feel that organizations should be implementing AI? What is your thoughts on AI? Uh I AI the conversation is everywhere and I would say you know there are innovations there that are developing faster than any of us can kind of get our arms around.

[20:38]  I'll say that for third sector we're in the early stages of figuring out what AI means for our work internally. But I largely really agree with your comment that like focus on what is it that you uniquely as an organization as a nonprofit can bring to measurable improvements in people's lives and you should be trying to figure out how do you spend all of your time on that right and whether it's automation or it's in partnership with folks who do other things better than you do like whether that's AI or other enabled I think just having that clarity around like wait a minute what is it that we want to achieve What is it that we're really good at in terms of contributing to make that happen? Then think about who do we who do we hold hands with? Who what do we, you know, like automate um in order to to enable more of that great contribution work to happen. I think those are the right questions to be asking right now and honestly that we have to be asking in a world where there's going to be less resources and not more in the coming years. But do you feel that when you're having these conversations with other leaders that there is are you getting that push back as well when you say AI or you bring that up? I don't know if it's a conversation from you as a to another leader but I feel as a leader to another leader when I say AI there's still the people that it's just there's no way matter of fact I spoke to someone recently and she was like there's no way everyone tells me about chat GPT I'm not doing it and for me I'm all about education. So, I pulled up chatbt. I prompted her a couple of different things on the conversation we were having and within 2 three minutes she has chattyt on her computer. She signed in and she's sharing her screen like show me that again. And then on Sunday she says, um, "Thank you so much. I think I'm overusing chatpt, but the value you gave me is so helpful." And I just feel like you have to test it. You have to see how Yes, I get it. You're a great writer. You want to be personal, but you can still do that just faster. That's it.

[22:34]  I would say, you know, my my line for AI is active curiosity is essential because it is everywhere and it's going to be everywhere. And so what you just described was like embrace an active curiosity about it. But you should be doing that kind of across the board because we're in a time where we need, you know, a lot more radical curiosity, collaboration again to navigate the uncertainty that's out there. So I um I kind of you know to get back to your point about fear I try to take the embrace the uncertainty aspect and okay like well what do you do when things are uncertain times right you got to really think about get curious around what are the ways what are the things that are going to help you achieve stability in this moment and you've got to think about um who you're holding hands with who are you going to partner up with in order to um in order to survive and continue thriving in uncertain times who can you trust? Um, and who do you want to be in relationship with that cares about achieving the same goals that you do?

[23:36]  I love it. And actually, this last AI question before we move forward is if you could create an AI tool of your own, what does it look like? What is it solving?

[23:43]  Gosh, you know, one of the things that I think would be really helpful that I've actually seen some partners doing is um, so AI takes advantage of a lot of different data sets and there's a lot of information out there about grants, right? and what funders care about, what philanthropies care about. And gosh, I'm I mean, we're a nonprofit, too. We spend a lot of time researching, trying to figure out how do you write that best intro note or that best cover letter. And I think there's um some new advantages to to leveling the playing field really around accessing information about which foundations would be good ones to write reach out to for your nonprofit and others. And so that I think is a really valuable tool that I've actually seen wouldn't need to create that could really save folks a lot of time so you could focus on, you know, measurably improving people's lives and doing those responsive services as opposed to like which nonpr, you know, which foundation should we reach out to?

[24:41]  Yeah. And you mentioned grant writing. If people are not using AI to do grant writing, like you're you're falling behind again. Like it's it's out there. People are doing it. I'm hearing these things from other leaders. But um this is good. Can we talk about what's because you're a nonprofit and it's it's crazy to think that you're a nonprofit helping other nonprofits because you had some of these challenges yourself. It's almost like now you're kind of coaching other nonprofits like you're now the coach in the nonprofit space and you're helping others. But can we talk about more of what the third sector group is doing as well so that people that are here listening like what is she talking about? What what can she help me with so we can start to kind of drop those services?

[25:15]  Yeah. So I can give another example of the work that we do. So again, government funds a lot of different human services and we partner with state and locals to help them be in better relationship both funding and outcomes focused relationship with um other folks uh with their nonprofit providers. So, one example of where we came in and I think we we were helpful or at least the results show that we were helpful. Um, we were working with six rural counties in Texas who were struggling with how do we find how do we create good jobs at home and not require people to move to the big city in order to access opportunity? We're losing population like how do we access how do we help people access good jobs at home? So, we supported um the workforce boards in those six counties to define well, what does a good job look like? What is a good wage that provides benefits and opportunities for career advancement in your area? And then how would we think about okay, defining that and doing a map of what are there what are the actual like remote work opportunities um for folks where they wouldn't have to move and they could still achieve these good jobs. So um what the result was sort of at the systems level we were able to identify a couple of areas like IT truck driving um healthcare where there were some good job opportunities in those rural communities and then we were able to help recruit in new training providers. So that included Texas Tech University, the American Truck Driving School, other non nonprofit training providers that had not previously served this area and were now established in the region. So this is it was helpful not only to help us train and place 400 job seekers um in quality jobs with career advancement opportunities, but it also like shifted the ecosystem, the nonprofit ecosystem in that rural community and it gave those nonprofits honestly like funding. They knew that they could get paid to train people and place job seekers. um and it gave those job seekers in those rural counties more options, right, for ways that they could increase um their own wages and and thrive. So, that's that's another example of of what we do. And I think as part of that, we really ended up being kind of the nonprofit in the middle, if you will, that was um trying to help our governments actually be in better conversation with the nonprofit providers around what they needed, how much money they needed to do the work, like what the outcome goals were. Um because sometimes government says, "Oh, we can't talk to them. They're our vendors." No, they are your service delivery. they're like an extension of the service delivery um to to make sure you're delivering responsive services. And so that's a lot of times what we're doing is helping to be that bridge between nonprofits and their government partners.

[28:16]  What a good space to be in. I mean really getting the cup filled probably on both sides to be quite frank. Um, and it's nothing like doing chasing purpose and not a paycheck because let's be honest with the work that you do, uh, you could really be doing so much more, but there's a purpose there. There's a passion that you have always had. So, you'll continue to scale this at this level of helping other nonprofit uh, get to high levels as well. So, we appreciate what you do, but let's talk to those leaders. I feel like the leaders are are listening and they want to know, okay, so what's the first relationship I should be making uh, this year as a leader? Um, so if you can kind of talk to that, what what should be that first relationship every nonprofit leader should build this year?

[28:55]  Yeah, I would say again go back to that do that landscaping assessment. You know, the relationship you should invest in is with the person who is managing making funding decisions about the area um that you care about. So maybe it's the like homeless services manager, maybe it's the youth development coordinator, it's whoever is controlling the budget um from whether from the relevant government entities. So I would say again like seek to become a true partner um with folks that you know where you share the public goals of those in government because folks in government also care about positive impact as well in people's lives. Um, and

[29:40]  Caroline, real quick, I'm a I'm a big let's dumb it down because sometimes you can give them just this basics and they still don't know where to start. So, where do they start? Is it an email? Is it I'm going to an event? Is I'm knocking on some doors? Let's make it even easier for them.

[29:53]  I, you know, I'm a big fan. I say this as running a remote organization. I'm a big fan of find out who it is um that you want to be in relationship with and figure out a way to be with them in person. Yeah. And so whether that is um at an event that they're hosting or at a conference or getting an in-person meeting um that's the way to to make it happen.

[30:19]  I agree. The energy is very different in person. I'm pretty sure even this conversation like we're having a great conversation but what would it look like in person? I think it would be a vibe for sure. No. So I uh I like that. I just feel that I want to give them so much insight but also dumb it down because so many people as we mentioned you can give them the playbook but sometime it just doesn't make sense and to me it's always how do we make it make sense that's just I'm a big believer in that and it looks like you guys do that over there as well so I just wanted to make sure for the readers that are still here or the listeners that are still here that they can we made it make sense for them right like go see these people in person figure out who that is reach out via LinkedIn reach out email uh to get more information on them I mean you could probably know a lot by just stalking their LinkedIn, they're probably posting on where they going to be and maybe other events that they're going to be at and that's it. That's your end. Sometimes you got to do a little stocking.

[31:05]  And so much of it too is like if that doesn't work, think about well how how could you make them pay attention to you? And in some cases, if you can't get in touch with those that control the budget, reaching out to other nonprofits in your area that also care about the work you do and approaching as a collective versus as a single nonprofit can also be really helpful because it's like, oh wait, it's not just one constituent, it's like 10 that are coming and asking for a meeting, asking for a conversation about how we're going to support um homeless youth in our community in the face of all this uncertainty and like, okay, I'll show up to that if it's going to be 10 of those. Yeah.

[31:42]  I'll tell you what. Um it's really funny that you say what you're saying right now because as I sit here and think about we're putting together a gala. I took over this organization as I mentioned about a year ago and um they've only been doing about 10 to$15,000 over the last five years, right? Uh per year. And this is an organization that's been around for 30 years but has about half a million dollars in endowment. So obviously the potential was there. It's what happened? leadership failed somewhere like something happened there and you know they could blame it on a pandemic but pandemic was five years ago stop blaming it on a damn pandemic already what are you doing today so as I taken over this organization I said okay we celebrating 30 years this year what a perfect time to kind of relaunch rebrand let's have a gala people like to get dressed up have drinks and donate some money but I wasn't thinking about just like because it's a school I'm not just thinking about inviting those alumni but as you mentioned those community partners like figure out that there's kids graduate from Edgewater cuz some of these people have a relationship there. So now there's a relationship you can talk about. Um so I'm looking for for those. I did go to the mayor because his son is an alumni to Edgewater. So easy to get there. Um let's talk to the people at the school district, you know, because I have connection with the schools. You've been here as school secretary. I've been there 36 years. You must know everybody. So you are my go-to. Who are we going to bring? Because it's partnership. It's allowing people to see what the mission and the vision is. Once they believe it, people will jump on board. They will be more than willing to to help out. Whether that's putting you in front of other people. And I think that's important. It's it building relationship. Maybe that's not your donor. Maybe that's not the person that's going to help you, but maybe they can bring you to the table to the person that could and give you that million-doll check. I would never forget that someone told me, Ephrain, I wanted to be a realtor just because I knew they were making a lot of money when I was young. Uh but I was also already in the nonprofit space. And he says, "Ephra, do not do real estate. It's a career and there's no in and out of this.

[33:33]  Stick in the nonprofit. There's a lot of money to be made. People are writing million-dollar checks. You just have to ask and really be in the right rooms to everything that we said today. Caroline, anything else you want to add to those before we go into that blind question for people to just kind of think outside the box?

[33:49]  Ah, I love that idea of being in relationship partnership. And I, you know, someone said to me once, you know, the best way to get re to get resources is to actually to ask for advice. If you want advice, ask for resources. But if you want the resources, asking for advice can help you to get to navigate just as you described um those relationships that um end in the check. And the other thing I'd add is other advice that I got which is really helpful for me as a nonprofit is if you ultimately Yeah. You ultimately need grant money to survive, right? Like you need funding to survive, but

[34:27]  start with the relationship, then start with the project, then the check will come. If you start with the check, that's not as successful as if you start with relationship, the project, and then the actual funding.

[34:43]  I'm I'm going to look for something real quick. One moment. So, the whole time I'm talking to you, I'm getting these vibes. You're bringing back memories here. Hold on. I told you I used to It's It's stuck in wires, but I told you I used to sit here and work for the airline industry, so I've seen you the whole time and I'm like, "Hello." Like, you just bring me back memories. Okay.

[35:26]  No, I love it. Um,

[35:28]  it really bring back days. I used to work for the airline industry, customer service, and it was some good days, some bad days, but you learned just so much for being at home. So, I love this remote. I love that you've been remote. I love your vibe. I love that you authentically have been you this whole time and that you are realize it's not about you. It's not about us per se. It's about how do we help the future, you know, and and I can see that in you because from a young little girl, it was always about the future. It's about other people is how do we get people to see past their backyards um past of what they've been told or what they've been seen or you know shown in this case. So, thank you. Thank you so much Caroline for all the conversation. But are you ready for the blind question? Oh, yes. Bring it on.

[36:11]  All right, here we go. Blind question time. If you could erase, sorry, if you could erase one part of how government funds nonprofits, what would you replace it with?

[36:21]  Erase or replace. Sorry.

[36:23]  So, if you could erase one part of how government funds nonprofits, what would you replace it with? So, you're going to erase one, but you're going to replace it with something.

[36:30]  All right. I would erase cost reimbursement funding where you have to keep track of every penny and then you get paid after you do the thing because who has the money to front all of the money to like keep track of all the things. And I would replace it with outcomes focused funding. So where it's really clear what you want to achieve, what those metrics are, but that you get flexibility and dare I say at least half the money upfront in order to achieve um those goals. So that's what I would change about.

[37:01]  That was easy. That was That was too easy. All right. What is your blind question for the next leader here on the Heart and Hustle?

[37:05]  Oh, I got one. What would you do with $100 million? That's my blind question.

[37:12]  I love it. $100 million. And that's for just a nonprofit, right? From the nonprofit. Okay. Okay. Not a personal. Somebody would say house and car.

[37:19]  No, no, no. For a nonprofit. If your organization got a hund00 million, what would you do?

[37:24]  That is a hell of a question. I can't wait to see what the next people say on this one. But Caroline, you have been amazing. Where can we find you? Social media. Are you on LinkedIn? What's the website?

[37:33]  LinkedIn at Caroline Whistler. And then our website is Third Sector. www.third sector th hir dsectorcap.org. So that's us.

[37:44]  Let's go. Well, I appreciate it. You guys better follow Caroline. All right. If you guys want that nonprofit coach as well, to me, you're a nonprofit coach. I feel like I couldn't ask you anything and you probably have the answers.

[37:52]  You got a lot of good answers, too.

[37:55]  No, no, no. Well, thank you so much, Caroline, for your for your insight and your support and just for your time. Um, as well, thank you so much. If you guys I do this because we as leaders sometimes have imposter syndrome and then we we watch somebody like Caroline realize we're all in this together, right? Some days are better than others. We're in a if we can overcome the pandemic, I'm pretty sure we can overcome the next four years of what's happening here in our in our government. But, uh, you know, let's just for anyone listening, we can. We definitely can.

[38:22]  We can. And as my colleague said, like it's showtime, y'all. like we can not only overcome, but it's showtime. We got to bring it. Show the value. It was not Erica, but our colleague Kesha says it's showtime, right? It's showtime. Um, we've got to make it. We've got to show the value of the nonprofit sector and the value of our government over the next few years. We can do it.

[38:44]  Yes, we can. All right, guys. We're about to head out here. Thank you so much for watching here on another episode on the Heart and Hustle podcast. My name is Ephrain. This is Caroline. We'll catch you on the next episode. Lers.

cw
guest
Caroline Whistler — CEO, Third Sector
Nonprofit

Caroline Whistler is the CEO of Third Sector, an organization that works with nonprofits and government agencies to redesign public funding around outcomes. She has spent years helping mission driven organizations build strategic relationships with government partners rather than simply competing for grants. In this episode of Hart and Hustle, she discusses her own journey to recognizing systemic inequity, how nonprofits can identify who truly controls funding decisions, and why relationship building is central to sustainable public partnerships.

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