Carolina Democracy

Keep Squeezing the Cactus!

May 06, 2024 JD Wooten Season 3 Episode 17
Keep Squeezing the Cactus!
Carolina Democracy
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Carolina Democracy
Keep Squeezing the Cactus!
May 06, 2024 Season 3 Episode 17
JD Wooten

Welcome back to Carolina Democracy! Today we're digging back into our archives to share a version of a 2022 interview with progressive fundraising guru Sarah Squire. Sarah and I discuss her experiences involved politically, how that translated into political fundraising, and the importance of a good team. It's just as timely today as it was then!


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Show Notes Transcript

Welcome back to Carolina Democracy! Today we're digging back into our archives to share a version of a 2022 interview with progressive fundraising guru Sarah Squire. Sarah and I discuss her experiences involved politically, how that translated into political fundraising, and the importance of a good team. It's just as timely today as it was then!


Contact Us:

  • Email:

Follow Us:

Support the Show.

Sarah Squire: I will often say that political fundraising, especially for a campaign, it's like squeezing water out of a cactus and you keep squeezing the cactus until you've got every last drop.

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JD Wooten: Welcome back to Carolina Democracy. I’m JD Wooten, and this week we’re taking a little break from new content, but that doesn’t mean you have to take a break too. I thought we could dig back into the archives to share part of our #1 most downloaded episode – “Squeeze the Cactus” with Sarah Squire. There was a little from the original episode that’s not quite as relevant today, but overall most of it’s just as timely today as it was then. 

Sarah, in addition to her demanding day job, moonlights as an avid volunteer fundraiser for progressive candidates and organizations. Our interview ranged from how she first got involved in political fundraising for a compelling candidate to the great work she’s doing today to support organizations like Work for Democracy. In fact, when this airs, I will have just spent an afternoon at yet another event she organized to help Work for Democracy and Carolina Forward raise money for some incredible candidates running for office this year. In the spirit of that event, and this interview, I’ll leave links to both organizations in the show notes.

For those who heard this the first time it aired two years ago, I hope you’ll take another listen today. I really enjoyed listening to it again, at least Sarah’s part. I hate listening to myself, and especially our early episodes, but such as it is. Sarah has so much wonderful insight to share in this episode on getting involved, political fundraising, and the importance of a good team. And since we’ve grown quite a bit since it originally aired, I hope everyone else enjoys hearing from her for the first time.

We plan to be back next week with a new interview and new thoughts on the happenings in Raleigh and across the country impacting democracy, and you bet we’ve got  some thoughts. But in the meantime, here’s Sarah Squire reminding you to keep squeezing the cactus! 

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JD Wooten: With me today is Sarah Squire, a progressive fundraising guru who has worked with notable candidates like Terri LeGrand and organizations like Work for Democracy and the New North Carolina Project. Welcome Sarah. 

Sarah Squire: Thank you so much. It's great to be here. 

JD Wooten: Wonderful to have you. As always, let's start at the beginning. What's your first memory of politics or getting involved in politics? 

Sarah Squire: So my first tangible memory is from fifth grade. I ran for student body president and the reason that that really has a lot of meaning to me today, having truly worked in politics is that when I ran for student body president and I gave my speech in the assembly hall to all my classmates my campaign promise was that I was going to hold a baseball game between the fifth graders and the teachers at the end of the school year. And so, people gasped when I said that in my speech and it clearly struck a chord and it was probably why I was ultimately elected and within a couple of weeks of being elected kids were giving me a hard time on the playground because the game hadn't materialized. And like they were going to hold me accountable. And people gave me a hard time. This was back in the day of George Bush, Bush, senior, when he said, read my lips, no new taxes when he was campaigning. And so they were kind of mocking me and they're like, you're just like George Bush, read my lips, no new taxes. And I would like to think that I would have followed through on my campaign promise no matter what, but really the fact that I was interacting with my constituents and they were making sure that I kept my promise. That was really powerful. And ultimately we had that game. As in politics, you often need to make some negotiations. And so the principal did not like the idea of a baseball game because he thought it was a liability and that people could get injured. And so ultimately we modified it and we used a kick ball rather than a baseball and it's a little bit safer that way. But that is my that's my first memory. 

JD Wooten: I love it. So many elements of real-world politics happening right there in fifth grade for you to the people wanting their instant gratification, getting upset when they don't have results immediately. And then having to work out through some compromise to actually see it through that's brilliant. So you first jumped into political fundraising with Terri Legrand's race in 2018 for the state house. How did that come to be? 

Sarah Squire: So my story is not that unique in the sense that during the 2016 presidential election, I got activated more than I ever had before. And then after that election was over the only way that I could really deal with my grief was to basically make a personal commitment that I was going to make political engagement just an everyday part of my life. And so initially, before any races were starting to materialize, I wrote letters to the editor and I wrote some Op-Eds to various papers across the state. And I called my legislators and that was fine, but it wasn't really rewarding. And I felt like I was always on defense and I really wanted to go on offense and just like get new people into office. 

And so one day it was the fall. Fall of 2017. I remember a friend mentioned that there was this woman named Terri Legrand that was going to run for state house. I didn't know anything about state politics. But that's the first time I'd heard of Terri. And then a few months later, the same friend said, I'm going to hold a house party. Would you like to join me? And you know, I'd never been to a political fundraiser, never been to a house party. And I just was all in and this was like the new thing that I could focus my energy on. And so I felt like if we're gonna have a house party, we're gonna make it matter. And so I learned so much in that experience and the skill set that you need to develop to translate people from their inertia to action. I learned you can't send a mass email and everybody's going to show up, you gotta like remind people and do individual outreach. But I learned through that experience and then I gave this really passionate speech at the end of that evening to really ask people to double down and dig deep. And a couple of weeks later Terri's campaign manager reached out to me and was like, would you like to be on our finance team? And so then the rest is history.

JD Wooten: So before that, had you ever done any kind of major fundraising for a nonprofit or charity drive or anything else like that? 

Sarah Squire: No, I really hadn't.

JD Wooten: Okay. So you came into the ground floor and that makes what I'm about to say, just that much more impressive. So you came in, dove in head first managed to find your way on helping out with the finance team. As I understand it, by the end of Terri's 2018 race campaign raised almost $750,000 thereabout for Terri as a first-time candidate.

Sarah Squire: That sounds about right.

JD Wooten: So what was the secret sauce?

Sarah Squire: So I first just have to say that I got lucky and I stumbled into a campaign with an amazing candidate and that was just dumb luck. I barely knew Terri before we had this house party. But for those of you who haven't met Terri Legrand or seen her speak, that was her first time running and she is just this really dynamic, like extremely hardworking candidate who is such a public servant and who is just tremendous at building a movement. And being an amazing candidate is not just about your platform and your personality, but it's about your ability to get other people to jump on board. And so I lucked out in that respect. I also lucked out in the sense that as our team formed, there were four main women that really drove the campaign. So I became the volunteer finance director, and Terri's best friend Janet Lowe is tremendous and was her treasurer and made everything I did 10 times easier. And then Bree Hendrick is this tremendous woman who now works for the New North Carolina Project and she was our volunteer coordinator. And then together, we just formed a sisterhood. And I just have to say, I think that was in many ways our secret sauce. But I also would say that we really believed we could win, even though we weren't a targeted race. The district was roughly 40% Republican, 30% unaffiliated, and 30% Democrat. And we were not really on any radar. The caucus did not have us on their radar. And yet we knew it was a blue moon election, and we knew that Terri's race was going to be close to the top of the ballot. And we also knew that the incumbent that she was running against was not really campaigning very much. So we saw this as a true opportunity and we just ran the whole race as aggressively as possible and did everything we could to raise as much money as we could, and to recruit as many volunteers as we could.

JD Wooten: Brilliant strategy brilliant campaign there, unfortunately, as with many of us 2018 came up a little short, but just fast forward, two years, 2020, you stuck with Terri. Now she was running for the State Senate and those fundraising numbers jumped to $2.7 million overall what'd y'all do differently. And what was different in terms of the campaign cycle overall? 

Sarah Squire: Well, one thing that was very different was that her 2020 Senate race was considered one of the most pivotal opportunities to flip a seat from the very beginning. So in the 2018 race for NC house we did eventually become a targeted race and get the support of the caucus because our movement had grown and Terri's candidacy became way more viable. To me, that's some ways that's like my proudest accomplishment, like the numbers aren't impressive, but we had to overcome so much to get on the map in that 2018 race. In 2020, it was so different because of what I just said. It was still a Republican leaning district, but not by nearly as much. And so we were on the radar of various organizations from the get go like Lillian's list and Emily's list. And another huge difference is that we had a grassroots following that we had built in 2018. So when we jumped into call time that first weekend we weren't making cold calls. Or we weren't only going through Terri's family and friends. We had all of like her new family, right? Like her, her political family, the people that had poured their time and their treasure into her 2018 candidacy and who had so much respect for her. And it was a lot easier to make an ask in 2020 because they knew that she had what it took to win. So I think that was another key difference. 

JD Wooten: Yeah, there was always a constant battle for me with my campaign manager as to targeting who to call on call time, because he loved to point out that the most likely person to donate is somebody that has already donated. And in my mind it was like, no, no, they've already donated. I don't want to call them again. And he said, but they're the most likely to say yes. 

Sarah Squire: Amen. Yes. Yes. And there were moments...

JD Wooten: I'm sure y'all had those conversations too. 

Sarah Squire: Oh man. Well, I will often say that political fundraising, especially for a campaign, it's like squeezing water out of a cactus and you have certain cacti that you know, those cacti love you and they will give every last drop to you. And you keep squeezing the cactus until you've got every last drop and it's painful for the candidate because they're the one making the ask. But luckily there were more cacti in 2020. So we had a lot more to squeeze from, and that materialized in a lot more funds. But it is true. I tell candidates all the time, this is not like fundraising for a nonprofit where like, for example, if you're fundraising for the food bank, like you may make your annual ask and then you cultivate that relationship with the donor throughout the year and then you make another ask the following year. With political fundraising, there's so much more pressure and you do need to make multiple asks and it's not inappropriate to try to get for donations out of somebody during the election cycle. 

JD Wooten: These days you're doing a lot of fundraising work behind the scenes for organizations fighting for democracy across North Carolina. Let's start with Work for Democracy. For our listeners who haven't heard of them, what's the background of Work for Democracy and what they're trying to do? 

Sarah Squire: Worked for Democracy was founded in 2017 by a retired lawyer in Greensboro, North Carolina. His name is Sandy Vreeland. And Sandy was just a ordinary citizen who hadn't ever particularly been that engaged in political activism. And he, like many of us, was moved by what happened in the previous election and basically said we got to do something. And so what Sandy started was a state PAC. And initially the state PAC consisted of just a handful of his friends in Guilford County. And the goal was to raise money and also to get boots on the ground to support a candidate. And in Greensboro, there was a city council race that was taking place in 2017. And so they supported Tammi Thurm who had a great episode with you JD. And they put their weight behind Tammi Thurm's campaign and it was kind of like a pilot project for them. And it was wildly successful. And Tammy won in a very competitive race. I believe they flip that seat. 

And then in 2018, the executive committee decided to expand their reach to the most competitive state legislative races. And really at that point, were focusing on races that were in the Piedmont Triad. Since then the state PAC has actually evolved into uplifting candidates in the most pivotal state races all across North Carolina. So we've got 10 candidates that have been endorsed by Work for Democracy and they're running for both State House and state Senate. And one of the things that I love about Work for Democracy is that not all state PACs are very efficient with your money. So if you give a hundred dollars to a state PAC, maybe only $70 will go to the candidate. And then there may be a lot of overhead. Work for Democracy has a very lean budget and is entirely run by volunteers. And so one thing that we pride ourselves in is the fact that the vast majority of the money at roughly $19 out of every $20 is going to go to the candidates to uplift their races and give them a real shot at winning.

JD Wooten: Well, that's wonderful. So if I recall correctly, a PAC endorsement for a state candidate is not just a check, but in some instances, at least Work for Democracy helps with other fundraising or other organizing. Is that right? 

Sarah Squire: So the main thing that we do for all the candidates is we give them a generous check. And so we had those checks go out to our candidates in the primary and now we're fundraising so that we can hopefully max out to those candidates in the general election. Now for some of the candidates, if they're in the Triad area as most of the members of Work for Democracy are in the Piedmont Triad when it gets closer to election time we also recruit our members to get on the phones and phone bank and also knock doors for the candidate. So that's another significant contribution that we're able to make to certain campaigns. 

JD Wooten: Excellent. So what's your role with Work for Democracy and how has that experience been different than working directly on a campaign? 

Sarah Squire: My main role in the organization, I volunteer as a fundraiser, so I basically constantly nudge people to give money. I think that's really how you sum it up. That's that's my role in Work for Democracy is to try to make sure that we can max out to our candidates in both election cycles. 

JD Wooten: I love it. So I think it would be helpful for listeners if we maybe explain a little bit of the nuts and bolts of campaign fundraising. And we can keep this very brief because most people listening aren't actually running campaign finance. But having a sense of what's going on at the campaign level might interest them. And at a very high level, what would a successful fundraising plan look like for a State House or State Senate race? 

Sarah Squire: So I believe that having multiple fundraising events to serve as the anchors for your fundraising for your race is really impactful. And so, for example, when Terri was running for North Carolina Senate, the first time we launched into call time, we didn't even have a date set yet for her kickoff fundraiser, but basically Terri was on the phone and she said, I'm running for NC Senate. I was recruited for these reasons. I know we can win this race. This is why it's so critical. And we are, we're getting everything in place as soon as we can. We're going to have a launch fundraiser in November. And while we haven't pinned down the date yet, I would love to put you on the host committee. And it would mean the world to me if you could dig as deep as you can and make a donation of X amount of money. And what I find is that if you have these events where people can dig deep to be a sponsor, it's very motivational and it gives people something to reach for. And so then three months later when you're calling again, like you've got another event, a reason to ask them to dig deep again. And while that's not the only thing that people can reach for, like, sometimes you're going to be anchoring your fundraising around quarterly deadlines or you're going to fundraise around high-impact emails. I think that having a lot of events is really key. 

In terms of call time, I think that obviously the more call time, the better, but a lot of people that are running for local and state office don't have the luxury of campaigning full time. Most people are also working full time or they're raising a family or they're doing both. And so with Terri, it was not just about how many hours we spent on the phone, but how smart we were with that time. And so ideally every candidate should have someone supporting them during their call time, putting call time on their calendar on a regular basis, and holding that candidate accountable so that there's no way of getting out of it and helping that candidate hit the ground running at the beginning of each session so that there really is a strategy. Have a list and know exactly who you're going to call, what the ask is going to be. And in some ways like these candidates they're just being pulled in so many directions and their brains are getting fried. And sometimes it's just really helpful to have someone supporting you and telling you this is what we're going to do and okay let's dial, let's go. 

JD Wooten: You just hit on a great point I think too is simplifying it for the candidate. For me, it was sitting my butt in a chair and handing me a three ring binder where each page was a new donor with some research background, donor history, that kind of thing. I'm curious, in terms of approaching call time, what'd, y'all find was effective for y'all. 

Sarah Squire: I would say that it is really important when you do call time to take a little extra effort as the supporter, as the campaign manager or the finance director to personalize it so that when the person hears the voicemail or when they talk to someone on the phone that they don't just feel like they're in a cast of thousands. And also, making sure that we did not just end the ask with a voicemail or a phone call, making sure that we followed through with emails until the donation was secured. And so tenacity really pays off. And I keep telling candidates that most of your call time is going to be voicemails. And if you just leave a voicemail, there's a very low chance that that's going to turn into a donation. So you've got to follow up those voicemails with personal emails. Not cookie cutter emails, but like a personal email that's going to catch the supporters attention, and don't be afraid to keep nudging until you get an answer.

JD Wooten: So you've talked about call time. We've talked about events. How about those amazing emails we all love to hate on? Where do those fit into this? 

Sarah Squire: Emails were also a significant part of our fundraising, but not as much as call time or events. Call time events and events were definitely where most of the fundraising came in. And that said, I do believe that emails can be very impactful if a) you are not sending them too often, right? Secondly, we try not to make our emails too long because people have short attention spans. I think it's good to always have a catchy title. We call that clickbait, right? And so when we send an email, I think like, well, like what kind of title would be hard to resist clicking upon? So I think that makes a difference too. And I think it's really good to tell a story. So we know what those cookie cutter emails are. We get plenty of those in our in baskets where you're like, I'm pretty darn sure the candidate's not write in that email and had nothing to do with that email. We would make a lot of the emails personal stories that Terri would type out. And then we'd make sure it was pared down a little bit so it wasn't too long, but Terri was great at writing stories from the heart. And not only did those help with fundraising, but I think they also helped supporters get to know her better and identify more with her. And I think that also like made a difference in terms of translating to more volunteers down the line. 

And then another thing that I would say, and I'll end with this, is that I think it's really important to take advantage of current events that are top of mind for people that are making them really angry or fearful or frustrated. For example, when the Kavanaugh hearings were taking place, I mean, everyone was talking about that. Everybody had strong emotions about that, and that is the time for a candidate to translate anger and frustration into action. And I always tell candidates, like you've got to seize those opportunities because I really believe that those are the times when you're going to have the best results with those emails.

JD Wooten: Absolutely. So Sarah, any closing thoughts for our listeners?

Sarah Squire: So my closing thoughts would be first of all, for candidates, if you are struggling in any way with fundraising, make sure that your mindset is a good one that sets you up for success. Remember, you're not fundraising for yourself. You're not padding your own pockets. You're putting yourself out there and you're making yourself vulnerable and doing the hardest work of any of us. And so by taking on this responsibility, in order to succeed, you've got to make those phone calls and you've got to make those asks and that's okay. You do not need to feel self-conscious about that. Just any self-consciousness I just want you to throw it out the window right now. This is just part of the game. If you're listening, you're obviously pretty engaged. And so please find candidates that you identify with and uplift them with a donation, whether it's $5 or $500 candidates need as much support as they can get. 

JD Wooten: Well, Sarah, thank you so much for joining me today. It's been a delight.

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JD Wooten: Thanks again to everyone for listening today. If you have questions, comments, or suggestions for future episodes, send me an email at And as always, please subscribe wherever you get your podcasts and share this episode with a friend. Together, we can achieve a better North Carolina for everyone!