Episode 18.1: A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles

A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles

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 “I was the first woman in 2020, in the Kentucky House to give birth while serving, that means we have not had nearly enough women in their twenties, thirties, and forties serving.”

Josie Raymond
Episode #18.1


In this episode of What the Fundraising Podcast…

I talk to Josie Raymond, the State Representative for Kentucky’s 31st District, and the Director of Elected Leadership Fellowships at Leadership for Educational Equity. Josie tells us about her background as a journalist writing about poverty, being a teacher, a higher education coach, and finally her entry into the political world with one goal in mind: ending poverty in America.

From a nonprofit perspective, it seems that political fundraising breaks all the rules; selling email lists, and a somewhat fraudulent sense of urgency is just the beginning of it. But actually, this isn’t true for most elections, and there is another way to raise money that focuses on building community and providing a sense of belonging (just like in the nonprofit world but with some new and transferable strategies to apply today).

A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles

Join this conversation with this amazing mom of three who took matters into her own hands in her hometown of Louisville, Kentucky. Josie is an example of a brave and aligned political fundraiser, and an advocate for more women to run for office and for citizens, in general, to get involved with their community at the core level of policy-making. I promise this is a special episode, you don’t want to miss it!


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A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles
A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles
A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles

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I teach nonprofit fundraisers to bring in more gifts from the RIGHT donors… so they can stop hounding people for money. Fundraising doesn’t have to be uncomfortable.


A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles


Get to know your state representatives!

Do you know who your state representatives are? Do you know the issues they ran on? In this episode instead of highlighting a nonprofit as we usually do, Josie leaves us with an invitation to go deeper into our civic education and the awareness of what’s happening in our communities, our districts, and our states. 

Go visit the website www.runforoffice.org Whether you are thinking about running for office or not, this is a great resource to know who’s elected in your area. If you like them and would like to support them, give $5 to their campaign and get involved in elected politics in your community. And if you think you could do a better job, get in touch with Josie!

Visit www.runforoffice.org

episode transcript

Mallory: Welcome everyone. I’m so thrilled to be here today with Kentucky State Representative Josie Raymond. Josie, thank you so much for joining us today on What The Fundraising. 

Josie: Hey there, thank you.

Mallory: I want to dive into all of your history around your entry into the political world, but I’d love if you just start giving a little background on you and what brings you to this moment in time. I know even in your process of running for office, there were so many personal things going on. And so I just love for folks to get a sense for who you are.

Josie: Thanks for having me on. The fact that I was invited makes me feel validated as a fundraiser. So I hope I have something to offer the universe, but so I grew up here in Louisville, Kentucky in the neighborhood that I now represent in the legislature.

And I say, I grew up in poverty with privilege and I was a free lunch kid here and that really shaped my life and my career. I got a great education, had some great mentors, had opportunities that many of my peers didn’t. I recognize that. And so I said, “I’m going to commit my career and my life to ending poverty in America.”

That’s a big goal. But I feel very strongly about naming that and it has guided all of my career decisions and civic decisions along the way. I was not one of those people who came out of the womb and started planning my run for president. Those people exist and, good for them. I wasn’t one.

I was a journalist writing about poverty issues. Then I became a teacher through Teach for America, and then I was in College Access Nonprofits I’ve been a Student Success Coach in higher ed and in each of these steps, doing so much direct service, I thought, I can grant dignity and help individual students and families.

But there’s the same systemic barriers, creating these challenges for them. And so we’re going to really tackle these systemic challenges. And then it was like “Eureka! Elected office”. And now I’ve been there three years and I joke “Is that really the place?” But for now, that is where I’m trying to make my impact on poverty.

Mallory: Wow. Wow. I think your story is so inspiring, especially to the folks who are listening to this, because you share so many similarities with so many of our listeners in your own journey. I actually did a citizen schools teaching fellowship program. That was one of my first nonprofit roles.

And so really I am also rooted in education work. There’s a lot of overlap in our education work that you’ve done over the course of the years.

Josie: I thought, “I’m going to be a teacher forever.”  And then I taught for two years. My students who were 16 year old, eighth graders were using punctuation for the first time in their lives, which was pretty incredible, but ultimately not going to change the trajectory of their lives.

I’m a really impact hungry person. And so I thought I’m willing to step away from you all to try and find a space where I’m making a greater impact on the world that is shaping you all. 

Mallory: Okay. So let’s dive into that experience. Tell us about your experience running for office. Take us through that journey for a second.

Josie: So I got this idea in my head. I was moving home to Kentucky. I lived in New York, in Indianapolis, in Oakland… I started building my own family, moved home to Louisville, where I’m from, started working with young people here and service felt different here. The kids here felt like me growing up and I just felt more rooted.

And I got this idea that maybe I could make an impact in elected office. I thought “I’ve been a teacher, I’m comfortable enough with public speaking, and I care deeply about individuals. I think I would be good at that constituent services piece. And I’m prettyhardcore and focused and I think I could run a really good campaign”. So I felt like I checked enough boxes and I said, “Okay, I’m going to run for office!” 

So I looked around, Congress felt far off to me, I wasn’t interested in the challenges at the city council level, and I identified my state representative role in my district.

I thought it was filled by somebody who was not super connected to our community and was not doing the best that he could for our community. So I thought, “That’s my race.” And I just started learning everything I could about campaigning. 

Now I know how naive I was. I know what people were saying behind my back about how crazy I was, because it’s so rare for a concerned citizen, and a concerned mom to put their name on the ballot. And I think people don’t know that usually the people who run for office have been connected through a political party, or they’re chosen by the person who’s retiring these sorts of things. And it’s very rare for just your average person to say: “I’m gonna run”.

Mallory: That’s amazing. Had there been in your region, another person who had been tapped to take over that race and you just didn’t realize that was how things typically worked. And so you were like, “All right, I guess it will be me!” 

Josie: I started by challenging that incumbent. Itt was a democratic primary, I’m a Democrat. And I was running against the incumbent Democrat and had been there 26 years since I was a little girl in this district. And that, of course in many places is frowned upon but I’m just so hungry to make an impact on the issues that I care about. And, as I went around the city and met the influential folks and told them my plan, the whole thing, trying to build some support. I heard a lot like, “Wait your turn”, or “What if we could talk him into retiring in a couple of years?”

And I just felt like our challenges are great. Let’s not wait. We can’t wait. And I thought, I think I can learn what it takes to run a good campaign. There’s so many books and seminars and resources. I’m a member of Leadership for Educational Equity, which is an organization that develops civic leaders.

And so I got coaching there and I really was blinded by my desire to make an impact on poverty in Kentucky and that made everything else, knocking on thousands of doors, raising a whole lot of money, seem doable or not as scary as they are when you’re just looking at that obstacle. 

Mallory: Okay. So I’m super glad you brought up the fundraising because I’m curious when you were making this decision and it sounds like what’s so inspiring about your story is that it sounds like the decision was just from such a heart-centered place around “This is the impact I want to make”. And not necessarily from “Here’s my spreadsheet of all the pros and cons of running for this seat”.

Was there anything that sort of came up for you when you thought about, “Oh my gosh. Okay. I’m doing it”. Around the fundraising component, any sort of fears or discomfort or overarching sort of apprehension about that piece of it?

Josie: Yeah. Yeah. I appreciate you receiving that message that it was heart-centered. When I started running, I didn’t know what the job of state representative paid or any of the other benefits.

And it was much, much later when it looked like I would win that the veteran rep took me aside and took me through the nuts and bolts of it, which I appreciated, now I try to pay that forward. But no, I grew up and my family wasn’t very political and I didn’t know elected officials, I’d never been involved in a campaign.

And so I think I had some of that feeling that so many people have about politics of this is an icky business. I recognized that policy is made through politics. So I was willing to engage in it, to get to the policy-making space, but I thought, campaigns, there’s just so much money flying around and is it dirty money? And what’s it all for anyway? 

My biggest barrier was maybe really early on when someone said this campaign is going to cost a hundred thousand dollars and I thought: “a hundred thousand dollars, what good could we do in our community with a hundred thousand dollars?” And of course it’s not a huge pile of money that’s sitting there and you get to decide whether it’s used toward a campaign or buying a family, a home or something like that.

Of course I was much more frugal and learned to do things on my own. And so it didn’t cost a hundred thousand dollars, but I really had to learn what it was all about and get comfortable with the idea of the funds that I raised helped me spread a message of a more inclusive community, a stronger community, a healthier community, a better educated community, and invite people into the political process who haven’t traditionally been involved as donors and as voters.

So I had to do some of that work for myself really early on, and then I could get to learning how to raise money for a political campaign? Some of the best advice I got very early on from someone who was coaching me in a campaign was to make three budgets: bronze, silver and gold. 

So I did that and in the campaign that kind of looks like the bronze budget is what I need to not be embarrassed. I’m going to send three pieces of mail, call the likely voters and I’ll have little cards to hand out when I knock on doors and that’s about it. And then the silver was like  yard signs, we’re advertising on Facebook every day… And when I made those budgets and started getting quotes from printers, like really getting into the nitty gritty of it, I saw, “Oh, I think I can run a good race for $15,000”.

And then I could create the spreadsheet of how many people do I think will support me in this race. Oh my gosh. When I really get down to it, I think hundreds of people from college, from growing up together, my aunts and uncles, they will support me with donations of $25 or $50. And I started to just put those pieces together and see, this is doable. This is learnable and this is doable. 

Mallory: Wow. There’s something that you said a few minutes ago that I want to go back to because it’s something that I’ve been thinking about so much in preparation for these conversations about political fundraising, which in all transparency is new to me. I feel like I’m learning a lot through my interactions with LEE around the differences and similarities between fundraising for political campaigns and for nonprofits.

But one of the things you said is around this piece about the cost of the campaign. And I think this belief that we have, maybe outside folks like me, around that investment of money, that hundred thousand dollars or $15,000, whatever ended up being is there to either win or lose. This entire amount, because if I think about it from the nonprofits framework we invest in something, a solution and it either works or it doesn’t work.

And so when that sort of same mindset gets applied to campaign fundraising. You either win or you don’t win. And so then if I donated to your campaign and you didn’t win, was that just money wasted? But what I think you’re saying or what you were saying, and what I continue to hear from folks is about how much important value is in the campaigning itself that really, I think from an investment and a fundraising standpoint, is a really important message. What you said about how long was your campaign from beginning to end?

Josie: I ran for about 18 months. 

Mallory: So I think about 18 months of you engaging people in your local community, in what’s happening around them, educating them on the topic, understanding what’s really important to them, creating priorities based on this data you’re collecting. A hundred thousand dollars, in my opinion, is nothing for the amount of work that you did to bring your community together, right?

What do you think about that? 

Josie: Yes. Yes. Yes. Thank you for that. I felt like I had a lot of public education or civic education that I was doing through the campaign.

One initial baseline piece is your donation to my political campaign, and any political campaign, it’s not for the candidate, my bank account didn’t grow during the campaign. There’s more money in my campaign account that there is in my personal account for sure. But it’s not a favor and it’s not charity either.

It’s an investment in the movement of the campaign and the values of the campaign. And I would say, I looked at the house to my left and it’s a family of six Somali Muslim immigrants. I look to the family across my cul-de-sac and this is Louisville, Kentucky. And a lot of people don’t think of it this way. There’s four generations of Bhutanese refugees across my cul-de-sac. 

And I think “Aren’t these people worth the investment of receiving the piece of mail of being invited into the political process?” Saying, “I would be honored if you would cast your first vote as a new American citizen for me”. But if I lost, if any candidate loses the money that was invested in that campaign, I don’t consider it wasted. 

When I was knocking on doors, so many people would say “You’re the first candidate to ever knock on my door”. And I would think “You deserve that. And you’re worth that”, and that’s free of course, to go up to someone’s porch and knock on the door. And then you’re going to need about 8 cents to hand them that little card. 

I invited people in, right? We had conversations, and people felt heard for the first time. Some people wanted to yell at me. Okay, I’ll give you that experience. I was able to hold the incumbent than I was challenging accountable in a way that he hadn’t been for years and years, I was able to release issues.

My top legislative priority is early childhood education and expanding access to pre-K in Kentucky. And that was not in the conversation. And all of a sudden it’s a topic in the debate that folks are watching, even though my opponent and I were in the same political party. We were asked the top issue in our district and he said traffic, and I said hunger.

So those are two very different visions. And so I had gotten to that place that I think all candidates have to get to, which is like, why is it okay if I run and lose and what good can come out of it? And you can share that message with donors as well, that you’re investing in an experience and a movement and a community-building effort, strengthening our democracy and setting the stage for more people to engage in the process going forward as voters, donors and candidates.

Mallory: I love that, and I couldn’t agree more. And I actually think it’s a lesson for nonprofits as well around transparency when you’re trying new things or putting yourself out there to test a new solution to a problem. Just the conversation around all the value created in the in-between, how we typically define success in our culture being America as a massive umbrella statement there. But tell me about that piece of what you just said about, you can talk to your donors about this. Did you have that level of transparency with your donors at the beginning, maybe before you knew that you were going to win where you were sharing with them “Look, this isn’t about whether or not I win or lose this election. It’s about my role in having these issues heard and holding this person accountable.”

Josie: Yes. That was the pitch early on, especially when the race did not look favorable, there was a lot of transparency, like concrete and more theoretical.

I remember a fundraising email I put out that said “Yard signs cost $6 and 36 cents”. You’re so used to seeing them everywhere, and then I just want you to know this is what they cost and this is why I’m asking. The more concrete I was, the more donations that we would get digitally at least. 

But no, I would say, “I’m campaigning on early childhood education”. When’s the last time you heard about that, especially from this candidate? Never”. And so there would be people who said, “You know what? I want to hear you debating that, and so I’ll invest in that”. 

And then as we were sharing messaging or doing social media, I would take selfies with people at the door and say, “Here’s Susan, she’s on oxygen and she’s 78. And she just told me no one’s ever knocked before”. And for people who are invested in building and strengthening our democracy, I think that was valuable enough to kick in or kick in again, right to 10 or 15 or 20 bucks to keep me going. 

Mallory: And I do want to ask, you had mentioned that the money that you’re raising, wasn’t going to you personally. So how do folks who are running for office survive personally? 

Are they paid anything by their campaign? Do they need another job at the same time? How are folks making that work?

Josie: Oh, it really varies, right? There’s, I don’t know, a hundred thousand elected positions across the country. 

For the state legislature in Kentucky, we’re a part-time legislature. So I’m in our Capitol, Frankfurt, January through March, each year, and then a couple of days a month, the rest of the year. So I was working full-time at a university coaching students who had barriers to graduation. And I used up my vacation. I would take a day every month to go and knock on doors during the day to try and catch retirees who were at home, and then I would also knock on doors in the evenings a couple of days a week, but I used them on vacation days.

It was really challenging. And if a reporter would call, I wanted to call right back. Get in the newspaper. But I had a student in front of me who needed counseling on how to pay for their next semester. So it’s a hard balance. And that’s why you see in legislatures and city councils and Congress, especially very wealthy people serving for the most part, retirees lawyers in private practice, successful entrepreneurs…

There are very few elected officials who have a day job. And that’s something we need to continue to lift up and name and do whatever we can to break down barriers. It’s poisonous to propose legislation to pay yourself more. And I haven’t done it, but there are some really good conversations going on across the country about, should legislators, for example, be a full time position with a living wage that allows people to focus just on that they’ll be more effective. And it will allow single parents in, in ways that they aren’t now, it will allow young people in, it will allow people with student debt. It will allow hourly workers and low wage workers in. Those are voices that are missing from these spaces. And when their voices are missing from the policy-making space, you see them left out of meaningful policy. 

Mallory: Yeah, I think that’s so important. I’m going to ask this from a very ignorant place, but could you have paid yourself from your budget, from your campaign budget, or is that not allowed?

Josie: Not allowed unless you’re running for Congress.

When you’re running for Congress, you can do that. And there’s some rule about you’re allowed to pay yourself your previous salary or the congressional salary, whichever is lower. I think Alexandria Ocasio Cortez paid herself from her campaign fund, which was a very big fund. And she’s been very open that she was low wage when she was running.

For the most part, people who run for Congress are not taking advantage of that provision because they don’t need to, but no people who are running for local office or state office need to be working a day job or have a spouse who can support them, which is one reason why you don’t see single people doing it as often.

It’s very challenging. You need to have a lot go right in your life to be in a place where you can run for office these days. 

Mallory: Wow. Yeah, that is really sad, honestly. But when we think about how to fix some of the biggest systemic problems and think about how to have more representation in these elected offices, especially because folks are typically not going straight to congressional races, they’re starting in some of these smaller, more localized races. And so if they don’t have financial capacity or family structure to support them winning locally, then that seems like a really hard barrier to get over. 

Josie: You’ll hear personal stories, and lived experience is so important in policy making spaces. And so like in the Kentucky legislature, you’ll often hear, “I was a free lunch kid” or people who talk about how they received food stamps or other assistance, but it’s always past tense. Because we were able to get to a stable place where we could run for office. 

We have one renter in the Kentucky legislature out of 138 members. We have one renter. So that’s an outsize burden on that representative for hundreds of thousands of renters, we have in Kentucky. Because they’re not able to be there and share their experience.

I’m so passionate about women in particular, in their twenties, thirties, and forties, entering local and state elected office, because that’s where you get that bench, that pipeline, if you want to see female governors and female Congress, people of which there are too few, people need opportunities to enter at lower levels earlier.

And too many women are locked out right now. Systemically locked out. I will make one point. You can’t pay yourself if you’re running for an office below Congress, but I followed the lead of women across the country during my campaign in 2018 and asked my state election finance office for approval to use campaign funds for childcare.

This was a nationwide movement. I got approval here in Kentucky. Other women have been successful in other states. And some other women have been unsuccessful in some other states, but this is a movement now to put this into statute nationwide to say that campaign funds can be used for childcare.

And that’s one of the structural barriers that we’re trying to break down that will allow more moms of young children in particular to run and win.

Mallory: Yeah. Oh, that’s exciting to hear that’s happening. And I wanted to ask you about that. What’s it like being a mama with little ones doing this work? I think you ran your campaign when your second was really young. Right? 

Josie: When I first ran, my kids were three and one. And now my husband and I look at pictures from the campaign trail and we just thought: “What were we doing?” And the baby starts screaming in an event and then my husband would whisked him away. I was so blinded by thinking of the impact that I can make in this office than I thought we did, but not without struggles.

And now serving, I miss baseball games, bedtime and dinner time. And now my kids are seven and six and one, but to see the civic engagement that they have, their knowledge and their interests in current events and politics, and really the agency that they feel and what they see their mom doing. It means so much to me that it’s worth it.

I was the first Kentucky representative to give birth in. That happened in 2020. And I took my baby when she was just a few weeks old on the floor and I was giving a speech about women’s health care. And the feedback from that was really powerful. People weren’t used to seeing that and meant a lot to a lot of people here, and meant a lot to me.

But really if I was the first woman in 2020 in the Kentucky house to give birth while serving that means we have not had nearly enough women in their twenties, thirties, and forties serving. But when you run and you start to see when you represent something more than yourself, it’s a pretty overwhelming feeling.

When I first ran, we saw voter turnout go up, mostly women in their thirties. So that representation piece is powerful. And so that was a white mom in her thirties, but you don’t think of it as a really unique identity. But political spaces, it is. It speaks to how we need every identity out there, so people feel seen and invited into the process. 

Mallory: I love that. And my right hand woman over here in my business, Alison ran for mayor of her town, with her little one strapped to her. I don’t even know how old she was. You look at all of her campaigning pictures and there’s just baby little legs sticking out.

And just what an important message it sends to so many people like yes, both other women in their thirties. And I’m so glad to hear that about the voter turnout, but I just think in general, it’s humanizing us in all of our roles and just being able to give space for both, to be  that mama for your little one, and also out there representing women on the floor and their healthcare needs.I think that’s just so inspiring. 

So what do we do about this pay issue? It feels like a huge hurdle. What can someone who’s listening to this right now, who may be activated the way that I am around making it more financially accessible for folks to run without having the very personal network to support them. What can we, as a society do to shift this landscape?

Josie: Run for Congress! More of us have to run and go through the growling experience of being the first, or the second, or the third until we get the critical mass that we need to change the policy. We can be more public about it. Like I’ll say now as often as I can, the salary for the Kentucky state legislature is $188 and 22 cents a day. Because people have no idea. They think we make a ton of money or absolutely no money.

And so it’s just, it’s shining light on it. And of course that number is different. There’s 50 different numbers in 50 different states. So I think that the civic education piece is huge, the critical mass, I know I’m asking women to do something really challenging. But I say we didn’t make this mess, but like the moms need to clean it up, which is a very familiar feeling in America.

I think transparency is valuable. I’m thinking of, if there were a woman who launched her campaign today, I’d want her to say: “Here’s my annual salary, here’s what it costs to run this race, here’s what everything costs”. I’d like to use this provision, where I can use campaign funds for childcare and invite existing political donors and people in her circles that she’s going to activate to become political donors.

Do you want to invest in this different type of voice? I think that’s going to be exciting for people. We’ve seen record numbers of women elected in the last several years. And that’s the headline. It’s always a record number. Then you get to that we’re still at 25%, women in Congress. 

I want to mention that Congress is made up of 6% mothers of young children. There’s more Congress people who are prosecutors than mothers with young children. There were more Congress people who were born outside the United States than there are mothers of young children, so we’re vastly underrepresented, but I think it’s an opportunity to name these barriers and say, and I am one voice out of hundreds or thousands who are actively working to overcome it, but it’s going to take a critical mass.

And that’s where we are. I wish everything were easier, but it’s a tough moment. I want to reiterate though, that there are networks of support and every piece of it is teachable, trainable, learnable, doable. 

Mallory: I think the thing you’re also saying, which is really resonating with me, is just this constant need to keep the short game and the long game in mind at the same time. 

I think from an outside perspective, so much of what we see, when we see people fundraising and political spaces, at least what I feel like I see, maybe the one of 200 emails I open is there’s so much urgency, right? I don’t remember the last time I read a fundraising email that had the long game message to it. It’s like a lot of what we see as like “Your donation, we 10 X today. And if we don’t get it by midnight, then “real high urgency activation”. 

And I think what you’re saying, that’s actually super important, is if that alone is how we view decisions to run for office or to invest in these campaigns, we’re going to burn out on that message fast. And there’s a long game here around what it takes to change the status quo in these different spaces that’s actually going to allow us to shift the tides and create more space and enough momentum around these issues. Am I hearing that right? 

Josie: You put it well, that’s the message I’m sending out into the universe. This is my hypothesis. I need some people to go and do it and report back, which is what I’m doing here in Louisville, Kentucky and it’s working for me.

But no, it’s so funny. You said that about the emails. I was just writing down to ask you the question. Cause the only thing that makes me doubt is that I get the same emails, right? If we don’t raise $4,367 by midnight, the sky falls. And we know that’s fake and that doesn’t work for me, but here’s my question: Does it work? Because everyone keeps doing it. So I think gosh, it must work. 

But I say, I feel so strongly about it,  I’ll never do it because it’s fraudulent. And if that’s the end of my political career, that’s it. 

Mallory: Okay. I’m really glad you said that because first of all, I don’t have the data and I can actually look maybe after this call and interject or put it in the show notes if I can find some interesting data here around this. What’s super interesting about political fundraising to me is it actually breaks all the rules of nonprofit fundraising. 

You would never treat donors in nonprofit fundraising the way that people who give to political campaigns are treated in terms of selling lists to other people. I’m like, I don’t even know who you are. How did you get my email address? Oh, someone I gave it to sold the list. If a non-profit did that, they would get dragged so bad. That is a big no-no. 

The other thing is around how much you’re asking for money. It breaks every rule in the book, around the relationship between kind of cultivation, email. Emails that are just about having your audience become more problem aware or helping your audience feel a sense of belonging and community. And like all these things we spent all year doing this in our organizations to send out 4 to 10 asks a year, maybe. And I have nonprofit clients like: You want me to send two emails in one week? It’s wild.

Josie: On US senate campaigns, not at the local level. 

Mallory: But to me, first of all, I’m super happy to hear that isn’t your strategy and that there’s a way to win and a way to raise money, not doing it that way, because my guess is that a lot of people, especially if they come from a nonprofit fundraising background, they’re not going to want to fundraise that way. It does not feel in line with who they want to be as a fundraiser. And so my perception would be like, I wouldn’t do that either. I would never do that. And so then I think this question of is that the only way to raise money comes up.

And I just think that’s impossible. I don’t have the data to support it, but everything we know about human behavior, connection, belonging. Especially when it comes to recurring giving. I think some data that would be super interesting to look at is how that type of fundraising, how political fundraising works in year one.

And then what happens if the candidate doesn’t win in terms of the repetition of folks giving in the next campaign cycle versus someone who fundraises more like a nonprofit, more with the long game, deeper relationship building in mind. My guess would be that over the lifetime of the candidates’ races the giving would be much, much higher taking the nonprofit model, but it might not be higher in year one.

Josie: The kind of political fundraising we’re talking about, which is a national form of fundraising. If you’re like in a special election for a Georgia Senate seat, treating donors as  disposable, right? Like you’ll burn that bridge if you can get that 20 bucks and that doesn’t feel good to us. And you know what, maybe it didn’t feel good to those candidates who did it, but it felt necessary at the time.

We’re talking mostly about email, but the way most candidates at all levels, presidential down to your school board, the way that most candidates raise most of their money is call-time, or dialing for dollars. It’s not email. You’re supposed to calendar time, two hours a day, three hours a day. You sit down, you have a call list in front of you. 

You call Mallory: “How have you been? How’s the baby? I have an exciting announcement. I’m running for state representative. I know we share the same concerns, will you donate $250 to my campaign?”

And so when I talk to candidates, I want to name this and normalize it, right? Barack Obama did this. So you can do it for school board, but that’s how most of the fundraising is done. Much more effective than email, but uncomfortable for folks. I remember I broke all the rules around it because you’re supposed to have dedicated time on your calendar and sit down and have someone staff you, you have someone sit with you. As soon as you get the commitment, you hand them the phone to take the credit card number. Cause you’re dialing the next number. I had little kids, so I did my call time on the way to, and from daycare in the mornings and afternoons. And then if I had to write something down, I grabbed a diaper from the passenger seat and scribbled it down.

So that’s how I did it. I remember I called  my uncle  Lee, who I never called before, and I’ve never called since. And he thought someone had died. So that’s different from nonprofit fundraising,I imagine. 

Mallory: Yeah, we do that. There’s some of that, there’s some of the cold calling, but what’s really interesting is that I would say that those effectiveness numbers are switched from an email perspective and a call perspective. So perhaps it is this relentless emailing that is actually decreasing the effectiveness of those emails over time, right? I do a lot of work around habit building and behavior change, and we think about the moment that a person is going to take action. There has to be a certain combination of how motivated the person is to take action and how easy the action is to take, and then making sure that the prompt falls above the action line.

My guess is that when folks are emailing that frequently the prompt doesn’t work because the moment your folks stop opening your emails because they’re all the same, the prompt is wasted. 

I think what’s really interesting here is, and not to be judgmental and say, this thing is bad, but just to recognize for nonprofits, folks who are listening to this, who are like, I might be interested in running for office one day, but I don’t want to have to do it that way.

I think it’s really interesting to hear your story and that’s how you have felt too. And that there is another way to show up and to fundraise. And there are a lot of different ways to do that, depending if you have an uncle to call or not. And so I just want folks to recognize that just like with fundraising, for a nonprofit, really aligning it with who you are as a fundraiser and as a nonprofit leader, that’s critically important If you’re running for office.

Josie: Yeah, campaigns and campaign strategies are always evolving, right? There’s best practices, but maybe you remember growing up like I do, candidates used to get on nail files with their logos and stuff. Nobody does that anymore. It wasn’t really effective then would it be really effective now? Like why did that practice fall off? 

So things are always evolving and changing a couple of years ago. I remember everyone was like: “mail is dead, political mailers are dead, right?” You need to put all your money in digital. And then Facebook changed its ad mechanism, who can follow. And then everybody was in quarantine and it was like “mail is the future”.Everyone’s dying to get their mail every day. 

So everything’s always changing and it’s so right for innovation, and the most authentic connection, right? People I think are hungrier than ever front-end to connection or reconnection. The skills are so transferable. We’re talking about differences between nonprofits, fundraising, and political fundraising, but making the case and making the asking are so transferrable. And especially when you’re thinking about political spaces, making the ask is the most important skill because you start out making the ask for dollars and that enables you to get your cards printed with your picture of you and your dog. And then you’re using those to make the ask for the vote.

And then hopefully you’re elected. And then you’re asking your colleagues, you’re making the ask to your colleagues to co-sponsor your bill. And then you’re in a hearing and you’re making the ask for people to support the testimony they’re hearing about this new policy. And especially people who have been making a few more, join me in the policy making space.

Mallory: I love that because I think what you’re reminding us all of is that fundraising is just one other form of advocacy. And I think because of so many of the stigmas and taboos around money, it tends to be a form of advocacy that we get even more uncomfortable about. I’ve heard from so many fundraisers. I can go into a space and advocate for my program, my organization to partner with blank.

But like the moment I have to say that comes with a financial commitment. My whole stomach drops, right? I’m so scared. And that’s related to so many beliefs that we hold about money and value and investment and charity and all these like old school belief systems. So I think what’s so important about what you’re saying is that money is a mechanism, a tool to create change.

It’s one of the tools to create change and you advocate for it in the same way you’re advocating for these other things.

Josie: To spread your message, and to invite people into this process, to invite people, to make their voices heard, to invest in their neighbors, in their communities and the values that they believe in.

I always think about some other advice I got very early on. Someone said, “How does it feel to ask for money?” And I was like, “Ooh”. And then they said, “How does it feel to give money?” And I was like, “Amazing!” It feels so good to help someone or invest in something you believe in. And if we can just get people who are thinking about entering the public sphere to flip that switch, people are gonna feel really good to invest in you and the cause that you’re advocating for.

Mallory: I couldn’t agree more. And I’m so glad you said that because I think, for women in particular, who do want to do heart-centered work or trying to make a positive impact, we all do biologically have caretaker, harmonizer tendencies, and so we don’t want to rock boats. We don’t want to be in situations where we might do something that will make someone not like us. Like it activates all of our community building cells. I think those mindset shifts around our first sort of go-to when the fear of fundraising comes up, is “They’re going to be mad at me for asking”, or “My friends might not invite me to parties anymore because I always talk about my nonprofit”.

And then we think about what it feels like when our friends talk to us about something that’s so important to them and when we’re able to support their work and how good that feels. And so I think there’s so much here, both in terms of women getting involved in civic leadership in order to cause a big tidal wave on some of these issues. And also what happens inside us when we become embodied in our message and advocating for the things we believe in and the way we change as women in those moments. I think for me, that’s been so transformational and I think you modeled that so much.

Josie: Oh, thanks. It makes me feel alive when I see someone else feeling alive advocating for a cause. And just makes me say “Hell yeah, I’m all in. Let’s do this. What ‘s up next?” 

Mallory: Yeah. Okay. How can people find you? I usually invite folks at the end of these episodes to shout out a nonprofit that they love, if they want to highlight to people can check out and give, or if there’s another candidate you want to highlight and shout out. What’s the action? What’s the call to action right now? 

Josie: You can find me at josieraymond.com or Facebook, Instagram, Twitter @repjosieraymond. I would love for people to follow along, whether you’re in Kentucky or not, you might find it interesting politics. What I’d encourage everybody to do is go to runforoffice.org, whether you’re thinking about running or not. You type in your address, it shows you the list of positions, elected offices in your area, and this is a great place to start finding out who your state representative is, who your state Senator is, who your city councilperson is, your sheriff, your jailer… 

See who’s elected in your area, who they are. Then you can get to their website, their Facebook page, their legislative page, and learn more about who they are, what they’re bringing to the role and what they campaigned on. And if you see things that bother you. If you think you could do a better job, let me know josieraymond.com. We’ll talk about it. 

Mallory: I love it. I love it. And for everyone listening too, I really want to encourage some additional dialogue around the importance of investment in political campaigns far beyond whether or not the candidate is winning or losing. We’ll talk in some of these other episodes about how many times it typically takes before someone wins the seat and why it’s just so important for all of the things we said in terms of getting different issues to the tops of people’s conscious mind and added to holding other elected officials accountable. There’s so many important components to supporting politicians who are running on the values and action items that you believe in.

So thank you. Thank you. Thank you, Josie, for joining me today and having this conversation. 

Josie: Thanks for having me, there’s literature that says that people, women especially, have to be asked to run for office three or four or five, six times. And so if everybody out there I’m asking you. And if that’s not right for you, I’d say give $5 to a candidate in your area, see what it feels like and see what kind of response you get. It’s going to mean a whole lot to that person and it’s going to involve you in that, and I guarantee you’re going to feel more invested in elected politics in your community.

Mallory: I love that. Thank you. Thank you.

A Look Inside State Representative Josie Raymond’s Political Fundraising Journey and How to Get More Women in Leadership Roles
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