
Loading summary
A
In a world hungry for change, nonprofit impact matters more than ever. Yet every day, you're asked to do more with less. Less time, fewer resources, and tools that weren't even built for the way nonprofits actually work. What if you could do more with more? That's the promise of Bloomerang, the giving platform built for purpose. Bloomerang integrates fundraising, donor, and volunteer management into one intuitive platform. It connects your data to reveal real opportunity, showing you who's ready to give, when to reach out, and how to deepen every relationship. Because when your tools are built for purpose, your mission goes further. More connection, more confidence, more impact. Now that's more like it. Learn how you can do more with more@bloomerang.com that's bloomerang.com now on to the show. Hello and welcome to Nonprofit Nation. I'm your host, Julia Campbell, and I'm going to sit down with nonprofit industry experts, fundraisers, marketers, and everyone in between to get real and discuss what it takes to build that movement that you've been dreaming of. I created the Nonprofit Nation podcast to share practical wisdom and strategies to help you confidently find your voice, definitively grow your audience, and effectively build your movement. If you're a nonprofit newbie or an experienced professional who's looking to get more, visit ability, reach more people, and create even more impact, then you're in the right place. Let's get started. Hi, everyone. Welcome or welcome back to Nonprofit Nation. I'm your host, Julia Campbell. Thank you so much for being with me today. I have a pretty exciting, interesting, you know, sort of out of the box topic for you nonprofits here today, and it's how AI can support grassroots democracy and how we can support down ballot candidates, specifically progressive candidates. Sorry, you all know, you all know my political leanings, but we'll talk about the landscape of political campaigns, local political campaigns, because as we know, all politics are local and what that means for nonprofits and grassroots organizers. And my guests are Cristobal Duran and Derek Kitz, who are the founders of WinFlip, which is a specific platform working to close the gap between candidates and their districts and help them make smarter data informed decisions without the need for large consulting teams. Because we know, and I know as a locally elected official, affording a huge consulting team when you're doing a local election is often not feasible. So let's get started. Cristobal, I first approached you to be on the podcast because of what you posted on the Progressive Exchange listserv, and you wrote that you're building this AI driven campaign platform designed specifically for down ballot candidates, starting in Virginia, where I've lived. I really love Virginia with the focus on helping candidates quickly understand their districts and calculate realistic paths to victory. So maybe both of you can talk about how you founded winflip, what it is and sort of what gap it fills.
B
Well, thank you, Julia, for having us here. It's an amazing opportunity for us to share what we're doing, what we've been working on for quite a while now. As you mentioned, Derek and I met during our master's program at Virginia Tech. And Derek has a printing business and eventually he wanted me to join and we started working together ever since 2022, printing does get a little bit boring every now and then. So that's when AI kicked in and we saw an opportunity to help different candidates that we were already helping, but guide them in a better way. So that's how winflip came to life. And it's been a really, really interesting process of learning. Been a learning curve for sure. And we're just developing our new product, our mvp, which should be ready at the end of May of this year.
A
Oh, that's really pretty exciting. So how. Who first had the idea and how did you. You both came together when you were working on your Masters.
C
I already run for office because I'm a full masochist. And here you. I started a printing business that concentrated on a small. It was a small union shop that did mostly political printing. And so we started when Chris came on, he helped me run a campaign for the House of Delegates in Virginia. And we'd met and we clicked on for while we were getting our Masters. He got some interesting insight because he has a much different background than I do. We laugh and joke, we'll argue about the same things and we'll have the same point, but we're looking at it from two different angles. So we began to work together and then the way we processed information allowed us to come to a point where we realized that there's a gap here. What could we do? What can we do that doesn't repeat the same problems? Because every time we work with clients, we get a lot of first time clients, what they call the tier three races, people running for the House of Delegates that have never run or town council, they've never experienced anything and they all had the same questions and they all had the same problems. That's where we started to click. And we'd actually started it as like we wanted to help people do a campaign academy kind of thing. And Then Chris came up with the idea for winflip. It was based on, I was doing everything by hand. And Chris goes, we should do it like this.
B
The funny thing is that honestly it became an issue for us because we were getting the same questions over and over and it was kind of overwhelming because you're always going through the same pitch like, all right, you're going to do your wok card. When you do your wokcart, you gotta have your three priorities, who you are, what you're running for. And it's basically repetition over and over. And eventually that's when AI, the whole AI thing started and booming. So it was a good opportunity from, hey, let's do YouTube videos so they can watch them and we don't have to do this every single day to hey, why don't we do this with AI?
A
Exactly. So you said something, you said a what card.
C
Yeah, however you want to state it. One of the problems we had is we realized, especially a lot of Democrats, they always want to have this long winded explanation of what they're doing. And we realized a long time ago because I'm retired Army, so the army always teaches leadership in three to four points. And that's the way your mind has the ability to wrap around anything more than that. You start to either get too diversified and you can't concentrate on your main points, or you become, you start to micromanage the smaller ones. So three to four points, well, how do you teach them to do that? How do you teach people to whittle it down to what those three or four points are? That's what really, really started this. Because we spent so much time trying to get people to concentrate their message and to stay on message that it became like it was just beating us over the head. Every single candidate that came in made the exact same mistakes or had the same problems over and over and over again and you want to help people. I've got this pathological need to fix things. And Chris has a really good analytical mind as it comes to that. And this is where you get the joy of a friendship, where you see things from two different sides to be able to see the same problem and then come to something and we both go, that's awesome. So it's the same problems. It's those three to four points. It's the keeping the concentrate and keeping people on message, keeping people in the same branch so they're not using multiple things, doing multiple problems. And so nobody really knows what you stand for.
A
Right, exactly. And I non profits struggle with this as well. So how does this AI tool help them with this messaging? I know nonprofits struggle with this exact same thing. They have multiple programs, they're doing 50 different services, they want to tell everybody every little detail about everything. But how to simplify this messaging. I think that's really important for candidates, really important for anyone trying to sort of get influence people and change their behavior. So how does the platform help with that?
B
So coming from the political perspective we all know, I think in some sort of way we've all used AI. Whether you like it or not, either if you're Google searching or you are going straight to ChatGPT or whatever you using, there's always something that you are AI driven and it'll work that way. So we decided not to fight AI and actually use it in a way that it makes sense for candidates. And it's an ethical use of AI, especially because if you do like a ChatGPT search or Gemini search right now on politics, it's going to take information from everywhere. So it's going to go Reddit, Facebook page or post or groups and those can be really hardcore left, right, whatever. So you'll have some sort of problem when you don't have any guardrails to guide your AI. So to actually come up with something that it makes sense and it's true to what you're looking for. We try to stay non biased in terms of where it takes information from. One of the biggest things, and that's what actually took a longer time to develop, was coming up with the guardrails that could help the AI develop and help develop a message that could resonate with voters, but still not be super, super specific like this is your message kind of thing. And I know that Dirge had something mentioned regarding nonprofits back then back in Chile, because that's where I'm from. I started a nonprofit that worked with Chilean alumni who participated in any State Department program. So I worked really close to the US Embassy back in Chile. And that's where I'm with you on that one. It's really hard for nonprofits to work together and to get in our case with politics, it's voters. But when you got your advocates in nonprofit, how do you reach out? What's the message, what's the target and how are you prioritizing your message to people that are actually going to engage in that?
C
And then the other big hiccup in this was consistency. And that's the thing that we really wanted to nail down with the guardrails and this is how it helps a nonprofit is the consistency in voter information. And you could get a lot of things from ChatGPT, but it took about 20 minutes, and you kept getting multiple sources. And we wanted to limit it down to what type of sources we could get it from and to streamline that so you could get a breakdown of an area within two minutes. I mean, that's this. That's the key. That's the thing about how do you use AI effectively? And it's only used as consistently as you can frame your questions, because you have to give. Everything in AI requires context. And our context for this was the development of campaign resources, not voter influence, but tools for campaigns to use. That works for nonprofit, it works for individuals, it works for groups that want to concentrate on specific areas within a certain zone. So right now, it's just broken down by House districts, But the advanced product that we're working on now goes into other things like House of Delegates, goes to Senate, goes down. But everything is at state or local level right now. But consistency of message, consistency of information, those are additional guardrails beyond the other parts that we have that control the amount of information that's going on.
A
I think that's incredibly interesting. And I. I think that something you said earlier, where candidates, people are struggling with the same questions, you know, over and over and over again, and now they have sort of a place where they can go to get these questions answered in a consistent way and to sort of build their resources and build their toolkit for their campaign. So can you walk us through how AI can help a candidate better understand their district and maybe what their district is concerned about?
C
So one of the biggest things was getting your pool of information to be able to talk about it. And AI allows you to break down information and data by positions. It's not just a spreadsheet. So you're able to do targeted messaging and prioritization of all of your information. And I think that is a. I mean, taking it down to a nutshell and not getting too worried about it is a way to be able to bring all that information in.
B
That's exactly what I was going to say. AI is, is scary. But if we are able to guide it in a way where the message stays consistent, we are definitely helping out candidates or people that didn't really think they could run. That makes a difference. We're happy.
C
The thing about AI and the tool that it brings is you're able to analyze audience segments or voter segments or constituents, however you want to put it at Lightning speed.
A
And it's all based on public information, right?
C
Everything is based on public. We're not scraping anything that's not available to the average person. But ours is more about decision support instead of influence. We're not trying to step out and work in the misinformation part. We're trying to give a tool bag to individuals that normally couldn't afford to run. That's where we start talking about democratizing campaign strategy. It's 50,000 in consultants shouldn't be required for you to run for a House of Delegates. You should be able to get full tool package, as in having a full staff. That's the equity and democracy thing. The one thing you run into is people want to run. They don't even know where to start. They don't even know what questions to ask. And it's intimidating.
B
It's scary.
C
I mean, it's. Again, you joke about saying you're an elected official, I'm an elected official. But you get there. But it's hard. It's not easy. And I always joke with Chris. I said, all my lessons are painful and expensive, and that's the only way I learned. But what if you could help people that want to be the average person to run for office? Or you've got something you believe in, but you want to be able to analyze that faster, but you don't even know where to start.
A
So when we're like, for me, I know a lot of politics, especially where I live. There's a lot of candidate forums, like, in person. There's a lot of discussion on Facebook. There's a lot of actually just like knocking door to door. Can I help with. Maybe, like I'm thinking now the wheels are turning, like identifying neighborhoods maybe, that are underserved. And that could be wonderful grounds for either doing research on the ground, talking to people, where best to, like, focus your actual on the ground efforts.
B
That's actually the core element of what we're trying to develop here, being able to determine. To me as a Chilean, it's just crazy how much information there is here, public information regarding voters. And that was a little bit scary in the beginning. But once you embrace it and you want to use it for the good, I think it's a powerful tool. But once we start developing Wimbledon, one of the first things we wanted to do was say, hey, we don't want to develop a generic message where you're going to have, let's say you're running for a school board. You got someone also running for a school board. You're both using WinFlip and you're going to get the same strategy or where to go. That's something that we really didn't want to have. So that's why we developed the different archetypes. It's basically, it's a five minute form, doesn't take long, but it'll help you with develop your own tone and message. So it's going to be really true to what you stand for. It'll ask certain questions that are very straightforward, others are not as straightforward, but it'll help the AI understand the kind of person you are. Let's say if you were going to go to your first rally and you had music playing in the background, what is that song? So that will guide the AI and understand like okay, this person is more of a, like a southern vibe, like very local or let's say in our case it's more rural or maybe it's more of a we are the champions kind of queen, let's go. Kind of like that thing will guide the AI. So even though even being running for the same office, you're not going to get the same results. So once you complete your form again it doesn't take more than five minutes. It'll take that information, analyze the area you're running for and develop a complete system and strategy. It'll give you insights and determine the different areas you can target, how much budget you should allocate per precinct, what part of your message resonates better with this specific audience. So if we narrowed it down to something where it's really, really useful, especially for first time candidate and add to
C
that you're talking about, you're not going to neighborhood and you're starting to learn what the streets are. And there is a side panel that allows you to add information daily and keep a daily journal. And the AI incorporates all that and grows based on those inputs. I mean it requires user interface, you have to, you're only going to get out of it what you put into it. Because again the AI needs context, providing day to day showing how many doors you're knocking, how many things like that. And there's, there's a gamified effect to it. You get badges, you get, you know, certain levels you go to. But the AI during this whole entire time learns, I'm knocking 7th street and I've gotten a lot of good responses. I can just put that in a little chat on the side. The AI will incorporate that and go, hey, you had really good luck here. You had this many doors open. You had this much response, but the AI doesn't know unless you put it in. That was a big add on too, because the one thing we saw in the market was you've got a piece over here or a piece that does this for somebody or a piece that does that, but nothing that acts as an umbrella like a digital campaign manager, more or less. And this is not to replace anybody. This is to completely augment, to make staff, to make your opportunities better. So as you're knocking those doors on those streets, you're going to have your notes put in, and it's going to remember and it's going to remind you, hey, Julia, you on this street knocked this many doors. You might want to go back to this neighborhood again.
A
No, I love that. I think the most important piece of this is it's helping you figure out where to prioritize your very limited resources. And it's helping. It's like you said, it's this, you know, additional digital campaign organizer Internet that you can, you know, really help collate curate information that's relevant to your campaign and help make your campaign even better. So to me, I just see it as a win win for candidates. I see it as a win win for constituents. Because we all want, you know, to know more about the candidates. Well, maybe not all of us, but I know I do. I want to know more about the candidates that are representing me that I'm going to be voting for. I think. I just think this is fascinating because I've just been always such a huge proponent of more people running for office. And what I see here, I just. It's so hard to convince people to run for local office. There's myths and misconceptions and there's things that, you know, they think it's going to be so expensive and they, like you said, they think they're gonna have to hire a consultant, they're gonna have to hire a whole team. And often, you know, it's really just clarifying your message and figuring out about your district. And this tool seems to be really helpful in doing that. So you also talk about helping campaigns calculate a realistic win number. What is a win number?
C
So everybody has a tendency to think it's like 50% plus one, you know, and that, that, that comes out a lot. It comes out in a lot of literature. A lot of people talk about it. But I started running. I ran for office. I retired out of the army in 2015. I ran for Congress in 16. Then I ran for the House of Delegates in. I think it was 21. And then I began to realize that first question anybody would ask me was, what's your win number? And I was like, I don't know. And then you look at the votes and you'd be like, oh, I need to. The last person lost by 2000 votes. 2000 votes seems like a lot. If you're talking a total of 6,000, that's a lot. But then I began to look at it more and more and more, and I really nerd out and get into the weeds on this. And this is where Chris was able. It took us about eight months to get this to point where the AI could understand it because it was so nuanced in my ADHD addled brain. But you don't need 2,000 votes. You really only need two or 300. You need to turn this many. You need to flip this many. And people can wrap their head around that much smaller number because it's not. And you can also concentrate your funds a lot better. You already know what neighborhoods you need to work on, and the AI is able to do that because you're talking a much more grasp grass. Grasp is graspable.
B
The word area.
C
Remember, you can grasp.
A
So.
C
But that was the big key to it. That's where this came in. Win flip. What do you need to win to flip your district? Because I flipped a district that had been Republican, I think, for about 20 years, and I flipped it because I knew I didn't need a thousand votes. I just needed 200. I needed 200 either identifying new or to turn to flip my district. And I won. I think it was like three, five points, which is a lot in political spectrum, but it was really only like a couple hundred votes. And then we did it again to proof of concept for school board race out here. And that person won by about the exact same amount. And once Chris was able to get it all done, it took him a hot minute to get it where it was completely understandable and consistent. We were able to go back and look at races, and we were able to predict most of the races in the state of Virginia that flipped this year to a really close percentage of what it would be. And it was an explosive event to be able to realize that the numbers and the things you've worked on have come to fruition.
A
That is really. That's just so interesting. So the win number is something that is. I mean, for me, I didn't even know what that term was right. And I've actually run several campaigns, so I think these terms just helps candidates be Better informed of exactly what they need to do. But like you said, it's helping them manage their very limited time and limited resources, rather than throwing a bunch of spaghetti at the wall or buying a bunch of ads and not even knowing
B
where they go exactly, and just being able to help in democratizing running for office. That is, hey, one of the biggest barriers, the entry barriers we have, is that people are afraid because they think that they need to get 50,000, 100,000 or whatever, thousand votes. So they're going to have to be out there knocking doors, 100,000 doors, and they don't have a team. And they're like, this is impossible. I'm not going to be able to do this. But in reality, it's much closer than you think. And that's where WinFlip comes in very, very handy because just being able to help in a way where you can budget, allocate efficiently determine which precinct or area go to, almost like you can go to the level of, hey, maybe you should do this area on a Saturday, because usually that's when that population will be at home. And it'll narrow it down to a very specific guide on how to, how to move forward with your campaign.
A
So you, I'm sure both of you have seen in, I don't know, even recent years, but trust is just at an all time low in terms of trust for political institutions, trust for government, trust for even nonprofits. I think less than 50% of people, according to the Edelman Trust Barometer. Trust nonprofits to do a good job, which is just so upsetting to me. How can the use of AI maybe increase trust? And how are you reframing AI as a tool for empowerment rather than sort of manipulation?
B
So again, I go back to my times working at the nonprofit back in Chile. Being able to find those advocates you really wanted to that were part of who you were targeting was really hard because it's like sometimes a nonprofit, we always think like it should serve everyone because it's not doing any wrongdoing. It's actually a positive thing. So everyone can be a part of this. But in reality, you got to narrow it down to the people that will take action. And being able to understand who can actually do that is a big difference. And that's how AI is reshaping, how we strategize, how we move forward with what we're doing. Nonprofits are pretty much the same, and I know Derek's going to cover this, but nonprofits are not far from politics in terms of building something that sometimes it feels a little bit off from what people. They don't really understand your message, but you got to push what you're trying to do in order to link that together. You also had some.
C
So I don't have experience in nonprofits. Mine's political. So that's where we start talking back and forth. And we realized where a lot of that stuff connected. One of them you talked about, how do we build trust? Well, everything's grounded in transparency. I think that's important. And having a platform that resonates, the same transparency that your organization puts out, I think is a major, major influential. Also being able to show that the AI and your organization concentrates on decision support and not influence, I think that's another thing, because people get squirrely about misinformation and influence. But I think the decision support for what your organization stands for, I think is much more relevant to what we're doing, and it helps continue to build that trust. And on that level, you talk about, how would we look at this moving forward? Well, I see winclip as more of a playbook. A playbook and being able to standardize strategy moving forward and to remove barriers for people to be active in a nonprofit, to be able to start their own. Because a lot of people have these beliefs and they want to do good things, and they. And generally are good people, but they just get intimidated by the overall fact of what they're. What. What's in front of them, because it can be daunting to just look ahead. But if you have your transparency, you have your support for your decisions, and you have a platform in front of you that allows you to make conscious decisions and have that decision tree a little more simplified and more public for people to see. I think that's a. That's an honest way to move forward and to help build the trust gap that some people believe exists.
B
I just wouldn't say that it's really hard for nonprofits sometimes to show what they're doing because it doesn't resonate with people who are being vocal about why they don't like what you're doing and
A
they're worried about pushback.
B
Yeah, exactly. So AI is really useful and powerful. Again, as Derek mentioned earlier, it all goes back to how you prompt the AI but it will give you insights on what kind of message will resonate with certain people. So you don't guide. It's like a cheat sheet to make sure that your message serves exactly what that group of people will go like, oh, okay, it makes sense now, at
A
least I think that's so important. I also completely agree. I do see that nonprofits, they have a lot to do with politics, partisan or not, because what they're doing is filling a gap that the government doesn't fill and the private sector doesn't fill, and potentially working on a cause or an issue that not everyone agrees with that could be controversial and could be polarizing. So having the ability to stand in our truth and talk about our values and ethics and what we stand for and not be worried about the pushback or being able to address the questions that people might have around our work, it's a fraught time for everyone right now. So looking ahead three to five years, how do you see AI reshaping local campaigns and even nonprofit advocacy for the
C
campaigns I kind of hit on a little bit earlier. It's a standardization of strategy, not of the platform itself, you. But the strategy moving forward and the simplification of the process. We always said there's barriers that stand for people doing things, the intimidation portion. But if you had the tools in your hand and you had them in your phone and you could do it conversationally, that's the way forward. So you're doing it as a conversation. Chris makes fun of me because while I'm driving to work, I'll talk to my phone and I'll use an AI and discuss ideas while I'm driving. And he says I'm nuts because it's
B
the ideas I make fun of.
A
I love that. I think that's.
C
I talk and she talks back. I made her name herself, so that's
B
what I make fun of.
C
That's the way he makes fun of me. And I'm 57. I'm not supposed to embrace technology, but I am such a goober for this stuff. And it's just like, I talk and put my ideas in. And I've had to try to tell her to be much more critical and not be, oh, that's a great idea. No, it's not. It's a terrible way.
A
Yep. Because they. The AI wants to please you.
C
That's it. And I'm trying to. We want to have something that is. Will push back and accept the ideas and take your ideas and move forward with it. To be able to give you that playbook, to be able to have some standardization, to be able to have a level of comfortability that the average person can now run for office. Because you should have your best and brightest in public office. It shouldn't just be who's willing to do it. You should be you should be able to walk in and go, I want to make the world a better place, either through your nonprofit or going to politics. I mean, maybe I'm a little naive on that one because of my pathological need to fix things, but I try to look at things, and it's not an altruistic view, but I understand that everybody has an agenda. Some people's agendas are a lot better than others, and they really want to help people. And if I can help them with the nuts and bolts running around in my head, Chris can gather all that stuff and make a usable product. I think between the two of us, we come up with an idea. I think that's the playbook moving forward.
A
What do you think, Chris? How is it going to.
B
I agree, Derek. I think that being able to democratize something that should have the best people in office or in nonprofits is a must. Again, coming from Chile, I'm nonpartisan, but the whole idea of being able to help campaigns work more efficiently, my background different than Derek's, I come from a business background. So to me, it's more about efficiency and how we can help campaigns make this process easier for them, and that resonates in a better way with voters. So in reality, I see winflake, as Derek was saying, as a playbook, as the tool you want to have as your sidekick. Everyone should use it. And we've had the opportunity of pitching this idea to consultants, and you would think they would be scared because it's like, oh, you're trying to stay away from us. That's not true. What we're trying to do is we're trying to help you be more efficient. So what's going on is that when we were showing our very poor proof of concept, they saw insights and they were like, okay, so would this help me determine a budget for this X campaign? And it does. So having that ability is something that consultants appreciate. We also had the opportunity to pitch this idea with the party, and they also appreciated some other things. Being able to determine different areas and how to be more efficient because they manage, you know this. They got a lot of money, and they sometimes they don't know where to put it. But if you didn't show that you're able to flip the area you're in, if it's Republican in this case, they will do it if you got numbers. And that's why AI is very. Winflip is very helpful here because it helps. Like, hey, this is what we can do.
A
Yep, it's data driven. I love that. Well, this has been completely fascinating. So interesting. Where can people learn more about the both of you and winflip and connect with you online?
B
So right now we are at www.winflip AI and that's our current page. We've got our email address at the bottom. But you can also reach out to this, something broader which comes from our original project was called Project Icarus. We stayed away from that. It was just a code name, very, very military, I'd say. But you can go to WinFlip AI and reach out if you have any questions or ideas or insights. We're more than welcome to share those
C
or you'd love to invest because we're bootstrapping this one right now. We've come up, we're running a couple things to try to make this move forward. We think it's a great idea, a great proposition on this. We're moving on to our second phase and we've got some interest, but we need to be able to really, really push because AI is moving fast. We think we've got a very, very good product. We think we are able to be able to get this out to the masses. But to get it at the level that we need to get it, it's going to take more than just me and him.
B
And we are definitely bootstrapping, but we're also getting really good support from Amazon right now. AWS has invested in our project over 150k, which is very good for us because it helps us give the AI infrastructure that otherwise we wouldn't be able to get.
A
Well, I love supporting startups, especially startups with an incredible mission like democratizing campaign strategies. So best of luck to both of you. I'm going to put all the links in the show notes for anyone listening that is Winflip AI and I'll put your LinkedIn handles and people can connect and get more information there. So thank you so much for being on the show.
C
Thank you very much, Julie.
B
Appreciate your time.
A
Well, hey there. I wanted to say thank you for tuning into my show and for listening all the way to the end. If you really enjoyed today's conversation conversation, make sure to subscribe to the show in your favorite podcast app and you'll get new episodes downloaded as soon as they come out. I would love if you left me a rating or a review because this tells other people that my podcast is worth listening to and then me and my guests can reach even more earbuds and create even more impact. So that's pretty much it. I'll be back soon with a brand new episode. But until then you can find me on Instagram. Juliacampbell77 Keep changing the world, you non profit unicorn.
Guests: Cristobal Duran & Derek Kitts (Co-Founders, WinFlip)
Date: April 15, 2026
This episode explores the transformative potential of AI-driven tools for grassroots democracy, focusing on how AI can empower down-ballot candidates and support local, often resource-constrained, political campaigns. Host Julia Campbell sits down with Cristobal Duran and Derek Kitts, co-founders of WinFlip—an AI campaign platform—to discuss the challenges faced by local campaigns and nonprofits, the importance of data-driven strategy, and how ethical AI can democratize access to political power and community advocacy. The conversation offers candid insights into political storytelling, resource allocation, AI ethics, and strategies for building trust in today’s nonprofit and political landscape.
On the core problem:
"You get there. But it’s hard. It’s not easy. And I always joke with Chris. I said, all my lessons are painful and expensive, and that’s the only way I learned. But what if you could help people that want to be the average person to run for office?"
— Derek Kitts [15:20]
On bringing AI to the grassroots:
"We’re happy. The thing about AI… is you’re able to analyze audience segments or voter segments or constituents… at lightning speed."
— Derek Kitts [14:22]
On bridging access and equity:
"The equity and democracy thing… 50,000 in consultants shouldn’t be required for you to run for House of Delegates. You should be able to get full tool package, as in having a full staff. That’s… democratizing campaign strategy."
— Derek Kitts [14:38]
On AI ethics and community trust:
"Everything’s grounded in transparency. And having a platform that resonates the same transparency that your organization puts out… that’s a major, major influential [factor]."
— Derek Kitts [28:02]
On social impact:
"I think that being able to democratize something that should have the best people in office or in nonprofits is a must.”
— Cristobal Duran [33:43]
| Timestamp | Segment | |-----------|-----------------------------------------------------------------------------------------------------------------------| | 03:39 | Origins of WinFlip & Motivation | | 06:53 | Repetitive Campaign Issues Spark Need for Automation | | 08:31 | Message Clarity: Shared Challenge for Nonprofits & Campaigns | | 09:04 | How WinFlip’s AI Works & Ethical Guardrails | | 13:30 | Using AI to Understand Districts & Target Messaging | | 16:25 | Customizing AI Strategies Using Archetypes and Day-to-Day Learning | | 21:49 | Explaining the “Win Number” and Its Impact | | 26:09 | Rebuilding Trust and Addressing Skepticism with Transparency | | 31:33 | Future Vision: Standardization, Accessibility, and AI as Playbook for Democracy | | 35:53 | Where to Learn More about WinFlip & Call for Support |
For more on WinFlip, visit winflip.ai.
(End of summary)