Episode 18.3: Building Power, Organizing Our Communities and Moving Money with Taylor Stewart

18.3 Building Power, Organizing Our Communities and Moving Money with Taylor Stewart

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“We need that space of people really understanding their impacts, and we need that space of even more people coming from the experiences of the communities that they are actually from working in and serving in.”

Taylor Stewart

Episode #18.3


In this episode of What the Fundraising Podcast…

I talk to Taylor Stewart, Vice President of Organizing Leadership at Leadership for Educational Equity (LEE). She holds a BA in political science from the University of Missouri, a Masters of Arts in Teaching from Johns Hopkins University. 

Taylor shares her personal story working for justice in education as a high school government teacher and how her career shifted to law, fundraising, and working for educational equity in the nonprofit space. Her beliefs around empowering communities and the real deep-rooted changes that need to happen to fight bias and racism are a critical conversation for us all.

Even if our work is not the same, her mindset pretty much aligns with what I teach in my courses around saying no to martyrdom, focusing on community-centric work, and looking into our own beliefs and biases before they trickle down negatively into the programs we create. Listen to this episode and learn from this leader’s forward-thinking clarity!


Taylor Stewart


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18.3 Building Power, Organizing Our Communities and Moving Money with Taylor Stewart
18.3 Building Power, Organizing Our Communities and Moving Money with Taylor Stewart

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18.3 Building Power, Organizing Our Communities and Moving Money with Taylor Stewart


Get to know Strong Groups Maryland!

Strong Schools Maryland is leading the statewide, grassroots campaign in Maryland to create a world-class education system for every student, especially those who are disproportionately affected by policies because of race, poverty, language, and disability.

Visit strongschoolsmaryland.org

episode transcript

Mallory: Welcome everyone. I am thrilled to be here today with Taylor Stewart, the VP of Organizing Leadership at LEE. We have had so many amazing conversations about Lee and the work that you all do this week. And I’m just thrilled to be here with you today. 

Taylor: Thank you so much for having me. It’s a pleasure to be here.

Mallory: So, why don’t we just start with what brings you to your work today? I would love for you to share that with everyone.

Taylor: Absolutely. So I started my career as an educator in Baltimore City Schools. I fundamentally believe that as an educator, you also have this responsibility to your students to be an organizer in many ways, because you are building relationships with them.

I was teaching high school government and had my students asking me all the time “Well, you said that this is how it’s supposed to work, but I don’t think it works that way”, and they weren’t wrong. As a teacher, it was also my responsibility to say that there are ways that people have been able to change and fix things that are not working and living up to values.

That was the first three years of my career in professional work, being there alongside my students and getting the opportunity to organize with them and learn the city of Baltimore and the state of Maryland. So that was a transplant from the Midwest. Then it came to this point in time where I was looking at all of these systems, looking at all of the things we were working on and wanted to figure out some ways to be able to make some broader systemic change and learn some of the systems that were really frustrating my students.

I went to law school at Maryland and they extended the program and then I also took a job at Teach For America working in fundraising and working in development where I got this great opportunity to thrown in, to learn how does fundraising work, which was something that I had not done outside of being a kid in school fundraisers or helping some friends on campaigns and getting to kind of see what they did, to be able to raise money, but I was no way an expert on what development work even means

I just knew the mission of the organization and I really liked it. I was getting to tell that story. And in that work, I’ve often told people that you get to learn the landscape of power in a city incredibly well when you are fundraising in that place. Because a lot of the ways that decisions are made around money end up moving down to how decisions are made around policies, how decisions are made around who gets to make decisions. All of that flows through this network of who has money and can resource, especially a lot of the nonprofits that exist in a space. And who’s work gets valued and is able to continue and is lifted up as a model of where the city is going, and that influences a lot of policy.

I got to learn the power map of Baltimore through that space to understand how organized money worked in Baltimore. In that work I was also doing a lot of civic organizing with friends and trying to change laws and policies.

When an opportunity at leadership for educational equity came up to be able to start a region in Baltimore and actually do organizing work and actually make sure folks are going into high impact policy and advocacy roles. And that folks are getting into elected office and we can build an ecosystem, that was really exciting.

So I felt like I’ve learned a lot about how the systems were working. I thought it was working really well in the areas where I thought we needed to do better. I got to do that work and lead the region locally for about six years, until it transitioned into getting to lead a portfolio of regions and support folks across the country and figure out how to do that work in lots of different cities.

And then moved into getting to think about our organizing work and this whole sale all across the country and making sure that we have the resources and the capacity to be able to see change coming from organized people, but that change can never be possible without the ongoing thing of organized money.

One of the things that is trickiest in the organizing space and being able to sustain work, sustain campaigns and really build power is the space of where those two things fit together. I think about those topics a lot. 

Mallory:I feel like the word organizing gets thrown around a lot. Sometimes honestly, I feel like what they’re describing is slightly different. So I would love it if you define what organizing means to you and to LEE. What does that look like?

Taylor: Organizing work is the work of being able to build power and shift power in communities by bringing together people collectively over a set of shared interests, but the most important interest there is being able to have the power to say “This is how our community should function and work”. Intention with folks who were in positional power. Elected leaders, people who are appointed to positions and folks who have organized money and power. Oftentimes private businesses or foundations, all of that network of folks that we end up fundraising from.

Organizing is at its best and working when all three of those kinds of spaces have organized people, organized money and positional power. Our intention with each other is that a healthy space of all exists in a place. That power is not necessarily shared across them, but power exists in all of them. That’s going to be the healthiest space of society. For me. 

Mallory: I love the way you explained that. I feel like that’s really helpful. How much of this work? Or how transparent is the conversation around power in all of these pieces? You and I were talking a little bit, I mentioned there has been more transparent conversations in the nonprofit space recently about power and power dynamics. But talk to me a little bit about how that plays out in your work. 

Taylor: Sure. Organized money is actually a concept that people might not recognize from a language, but they know it when they see it. They can look around the place that they live and if you ask them who are some of the most powerful people, they will often mention heads of businesses or they’ll mention companies, or if you live in a city that has a lot of foundations and philanthropic spaces, people will mention those.

The way that you think about those spaces and their powers, they get to say these programs are the ones that work. These people are the ones that we want to invest in, and that keeps those programs sustained because ultimately, yes, we care and we’re mission-aligned, but people also do need to have a paycheck and you need to be able to sustain work, to keep it going.

From the organizing perspective, one of the things that can be actually really hard about the fundraising space within organizing is that while it’s true that civic organizing is really important, it also does take people who are in professional roles to be able to move on different things and sustain that work and organizing is grounded in shifting power.

You are inherently existing in and going to systems that have existed for a long time and have worked for folks, and making an argument like “Hey, these laws and policies need to change”, and you might be in agreement on that. But ultimately you’re saying we’re going to do this in a way that changes that system that works for you.

We want you to invest in that, which also happens for campaigns, for candidates who are trying to really move and change how things have operated and worked and trying to have a different look to who is in power. They have to then make a proposition of “I know that this thing has worked for you and yet it’s not working for everyone” and hope that the other person at the other side of the table is invested in that same change.

Even if it means that power is going to shift and be shared and they may have more people being able to then make decisions, being able to then act in ways that are going to change things for a greater number of people.

Mallory: Wow, I really appreciate the way you framed that out. So when you are making that case, and whether or not you’re the person that, consciously perhaps, understands what is personally at stake for them in investing in organizing work, what is the case around representative leadership to the everyday person who’s not already bought in or involved in that work and perhaps doesn’t even recognize? Maybe you even want to start with the scope of the problem and then why it’s so important that we’re changing it and how that case is made. 

Taylor: So when we start to look out at the landscape of leaders who are specially in those positions of power, we know that we do not have systems that are representative of the full diversity in the slate of our country. When we look at different percentages in particular fields that are really important to people’s lives, I like to go down to the local level and look if folks look like they are represented.

With our work at LEE, we oftentimes are supporting folks for school boards. It has only been in the last few years that we are starting to actually see more of a shift of school boards representing and looking like the student populations that are actually in their public schools. That has long been this space of really being able to hold onto power and perpetuate a lot of systems that have been harmful for students of color, as their populations continue to grow in public schools.

I also look at places like prosecutors offices and those spaces, spaces where they are elected and the most recent numbers on prosecutors in the United States, where 95% of them are white and 73% of them are white men. If we look at the criminal justice system, that is not the makeup of the folks who are coming before judges and going through those prosecutorial systems and being harmed by systems for folks who are impacted by them on a day-to-day basis, don’t come into the room necessarily with the experience of “These are folks who are in my community”.

I have a personal experience of family members of close friends having been part of this gold justice system and therefore not creating a system that is going to work for those communities. When we see that happening, we end up perpetuating a lot of the racism, a lot of the poverty that has continued to go on and systems of oppression, because the ones who were making decisions are saying “Hey, this actually works for me, this system seems to work”. It’s fair. It’s on its face because it’s fair for them. 

So going to that idea of it’s fair for them, one of the things that we talk about a lot in organizing is this idea of “You have to locate where the self-interest is for someone”. We kind of talk about the spectrum of “You don’t want people to be totally selfish and only concerned with themselves”.

You also don’t want people to be totally in this space of “Myself does not matter, I’m only self-sacrificial” because that is just a space of martyrdom. What you are trying to hit is this sweet spot of self-interest where people understand how their interests also sit in a community with other people.

When you start to talk with people and find what’s our self-interest, then you can start to figure out “Ok, so how do we invest together?” Being able to change a system that maybe, even if it’s working for you, is not working for these things or issues that we care about. A lot of that comes from being able to be in community and relationship with folks.

That’s part of why the fundraising process continues to be intensely relational and tends to still go to this space of needing to tell a story and paint a vision of what a thing is, but also asking a person questions about themselves so that you can actually tell a story and paint a vision that is within their self interest.

Ultimately for most people, even if a system kind of works for them on paper, you’re looking at them and the demographics and you’re like “Oh, there’s not going to be a space where we’re going to find any sort of common ground on this issue”. Most people have a story of “Here’s why the system exists and here’s why this thing doesn’t work for me or didn’t work for somebody who I care about”. Then it’s this space of being able to broaden that out and connect your story to their story and hopefully find some ground on “Yep, this is where we can invest together”. 

Mallory: Okay. People are going to think I had you say a bunch of that stuff because it aligns with how I teach fundraising in the nonprofit sector really around, especially what you said about the mutual benefit piece and I’m trained in something called Energy Leadership, and there are these levels of energy like catabolic energy, which is a really depleting energy. The lowest level of catabolic energy is martyrdom. The second lowest level of catabolic energy is conflict, but it’s “I win”.

You don’t want martyrdom. You don’t want “I win”. You want to get up to this place, as I talk about in these levels of leadership, where there exists this mutual benefit, sort of win-win. That comes with a belief, that I think you and I share, that the world can exist that way, that there is a world in which we can all win.

And I think sometimes that beliefs fall in conflict with many other people’s beliefs, especially in a capitalist society where people have one at the expense of others and it’s so hard for them to shift to an even belief system around a world that could exist actually, where I’m okay, and you’re okay and we can make these decisions together. What do you think about that?

Taylor: I think very, very similar spaces. I’ll lay out another thought from organizing a particularly broad-based organizing space in the industrial areas foundation, between the world is this and the world as it should be. That organizing exists in this tension of understanding the world as it is, especially in a political space that is very zero sum.

Somebody wins, somebody loses in lots of things and yet trying to shift power so that we can create this world as it should be, where winning does not have to mean somebody losing. That winning specially in a collective context where you are bringing lots of people together, having a shared interest and then moving work forward from that space can also mean “Hey, we are coming to these elected leaders and we are putting a demand and we’re putting tension on those folks”, but doing the thing that is the right policy decision also means deeper relationship with those leaders, also means a win that those leaders can celebrate right along with and in community with other folks, and it can mean their ongoing space of going to continue to lead because people are invested and they’ve built a level of trust.

There is this space where we have to hold intention. We’re recognizing the world as it is, and yes, it is possible to get to those wins on things that are in the world as it should be. But then a lot of those are going to be rooted then, in relationships, and having those hard conversations and being able to figure out what that space of mutual benefit and self-interest really is.

Mallory: You keep using the word systems. I had a conversation with someone recently around the last 18 months. I’m sure if we tracked it on Google Analytics or whatever, the term like systematic racism has been used more than we heard it before, but I don’t think that a lot of people necessarily understand what that means.

They hear this term, systematic racism being used all the time. They’re starting to hear ‘anti-racist’ word an all these other terms, but they don’t necessarily understand maybe the intersection between them or even what systems are at play. I’m curious, as you guys do the systems level work, where’s the intersection between that and like individual anti-racism work?

Taylor: It’s one of those things that some of the kinds of frameworks that we think about and are using, as we work with our members on the leadership development around helping them really understand what racism is, when we’re talking about that. What is the system structural stays as one framework is the four faces of oppression.

Helping folks understand racism from a space of Internalized experience of racism, and therefore the ways that, including people of color, will end up acting in ways that perpetuate racist systems because it is what they’ve experienced and known. The Interpersonal, which is to be really familiar for folks of this person or this group of people being acting in a racist manner toward a particular group of people, and then that space of Systemic that’s within a particular law or policy or a particular way that we operate in, do things. Are they baked in biases that are going to impact communities of color?

Then the space is Structural. How do those play off each other? And all of those systems come together to create this whole structural system around that kind of racism, that space of racism. I think one other thing that we have started to layer on and that I’ve had in conversations with members is Ibram Kendi’s work in talking about how does racism come about, and he says that lots of people think that racism exists first because of people having ignorant ideas about other folks, to then those developing into a broader scale racist idea, and then that turning out into discrimination in systems. So it starts at an individual level and then ends up at a system. 

And he says, actually, no, it goes the other way around. People with an interest to be able to do something, to discriminate in some sort of way, and it doesn’t even have to be that their interest is discrimination, but the way that they would achieve it is through needing to do that discrimination, will then justify that through a set of racist ideas. That then creates this space of people having that ignorance because that’s what the system around them is saying. So whenever we look at that from a space of schools, we have a long history of not wanting to really fund and resource schools in the ways that they need to.

We start from this space of “Well, we only want to give this much money at a budget”. It doesn’t have to be coming initially from that space of “Oh, that’s because we don’t want to invest in communities of color that have been severely disinvested in for really long periods of time”. They’re saying “No, If we’re looking across our electorate, if we’re looking across people in a community, we want to resource here and not resource here because we think that that will help our electoral gains”.

So you go there and you have that first decision about funding and we see severe funding imbalances in schools. But then we justify that by saying “Well, why would we want to focus-in on those schools in those urban or inner city communities? Because students there… it’s been a waste. We haven’t seen gains. We haven’t seen the improvements in education. We haven’t seen the real investment”, and “Hey, did you know that families in a lot of those communities don’t really care about education as much, and that they are really not as invested, so putting this money in there is going to continually be a waste”.

And then you get a whole lot of people who develop these ideas about places across the country, from where I live in Baltimore, to places like Chicago, to communities in New York, to communities throughout the south that end up giving these ideas of “Oh, well, yeah, those families in those communities don’t really care about education and therefore we don’t have to invest as much and therefore it’s fine if we invest where education is really going to be valued”. 

And that ends up perpetuating lots of laws and policies, and it becomes acceptable because it’s less tuned to what people would say “Oh, well, that’s not about racism, that’s just about the way things are”, when all of it came from this place of making a decision about the system that absolutely had true racist impacts on people. And then being able to describe that decision in ways that are going to continue to perpetuate really racist ideas. 

Mallory: You know, it’s interesting as I’m thinking about what you’re saying, and I’m curious how that kind of meets up with this trend we see in the non-profit sector all the time, where maybe it’s mixed with that martyrdom energy, but like “the white savior”, the “we know better” energy, like when you were talking before about representation on school boards and I was thinking that seems so obvious to me that a school board should look the same as the student body it represents. It just seems like a no brainer. And I was thinking “Why doesn’t that happen?”

In addition to everything you just laid out and all those different power dynamics. I wonder if another reason that it doesn’t happen that way is because people believe that they know better than the local community when it comes to solving problems. How do those things intersect? That disengagement of “We don’t want to put money there anymore because it doesn’t work”, and the “We know how to fix this problem” and removing the decision making and autonomy from the community.

Taylor: Absolutely. I think another direction that that space of the ignorant ideas that are kind of bred out of discriminatory assists ends up being that even really well-meaning people go into spaces and say “This just needs a technical solution with expertise, and folks there would absolutely do this if they just knew better, but because I’ve had the benefit of knowing all of these things, then I can come in and I can bring that expertise”.

We end up creating a whole lot of spaces that have policies that are well-meaning, but don’t actually meet the needs of the folks who are in the community, because there were a lot of solutions around things that nobody was asking for.

I think of how many times folks on Twitter post like “Who asked for this?”, and that is the experience of many folks of color and communities across the country. Where folks will come in and they’re just like “Oh, these are the projects that we are going to do and this is the way we’re going to fix it”. And nobody was doing the relational work of saying what would you actually define as the issue in your community and building on the experience of people to say “And what do you think would work here to fix it?”, before coming to some different conclusions. What ends up happening is we end up perpetuating these systems where it is this almost caretaker sort of space of “I want to care for this community. I want to serve and work for this community”, as opposed to “I want to be a part of this community and have just as much skin in the game about whether or not these solutions actually work and whether or not people are feeling invested in them”. 

The way that we get to that shift of having people who are part of a community actually having the power to make those decisions is through really thinking about this representative model within our decision-making thoughts and within our organizing and organized spaces, and they have to sit and kind of tension with each other there. 

I was really heartened earlier this summer watching Cori Bush at the Capitol in the house of representatives from St. Louis. First black woman to call that particular seat, and she is speaking of her experience being homeless and staging her sleeping on the steps of the Capitol, to get her colleagues to actually focus on issues around housing, as lots of COVID relief was going to be pulled back and there was real risk in a massive eviction crisis that we are hearing lots of news stories still on of “We need to get that eight out the door”. 

But the fact that she could tell a story of “I have been homeless, I know what this experience is, this is not a trivial thing for me”, of “I want to take care of people someday who might be homeless and do things for them. But I have been homeless and I know that the thing that is going to fix this is to make sure that people have the money to be able to stay in their house” is a different conversation than we would’ve been having if it were “I don’t know what that struggle is, but I know it must be really hard”, and “Have you read these 13 reports about homelessness” and all of these things that it might be able to fix it as opposed to “No, the need that folks have right now is to have the money to be able to stay in the home that they are in and can we just fix that and make sure it happens?”

Mallory: I think what you’re talking about is so critical and the relationship between, I don’t exactly know how to articulate this, but I’m going to try. I talk in my coaching work that a lot of times people will say “Is it bad that I did this thing?”, and I’m like “Well, we can’t really evaluate the actual loan. What drove the action? How did you feel after the action? How much consciousness was involved in the action?” Did you say “It’s going to feel really good for me to lay on this couch for three hours and watch Netflix”, and then you did, and then you were like “Yeah, I feel rejuvenated?”. Then there’s nothing problematic about that action. But if you are avoiding some feeling that you have and you’re trying to numb it down with three hours of Netflix, not consciously, you’re just sitting there and then you end those three hours and you feel stressed and anxious then maybe the action was problematic.

And I think what you’re talking about  is a level of consciousness around participation. That’s really critical because when people just act from an initial feeling standpoint, especially if they haven’t done a lot of unpacking around their unconscious biases, they’re likely to take an action that then later they’re like “Well, I was doing a good thing”, but it was coming from this place of pity and power and not partnership. And I think that is so fundamentally rooted in the problem that you’re talking about. 

Taylor: Absolutely. Within the whole conversation that has been coming up around voting rights legislation, a lot of that space has been around “Well, if the law isn’t actually specifically trying to harm this set of people then is it really a problem if we can then say on the other end, its impacts were incredibly harmful to a group of people? Now, I absolutely believe that a lot of voting legislation that’s around suppression is being passed with a discriminatory intent right now. But people are becoming far better at being able to cover that discriminatory intent.

We don’t always have the case out of North Carolina where literally legislators were in public, basically saying “This will ensure that these folks won’t be able to vote”. We don’t always have that. We still have it in levels that we shouldn’t. That is a lot of the intent, but then we’re seeing a lot of pushes within the court sites right now of “Well, do we get to look at this from an impact standard?”.

And this is across lots of legal areas of discrimination. It’s really important to be able to look at disparate impacts “Did this law, as written, even if it was written in neutral languages, hit people differently? And are those impacts actually disparate, especially across race?” So I think we have a lot of folks who are basically operating in this way of “No, I’m doing things in neutral ways, I am doing things in ways that are none of this ever be construed as being harmful or discriminatory”. 

But people don’t know what they don’t know, or they do know it and they’re ignoring the thing of “Hey, here is this community that if I don’t share backgrounds then I need to share relationships with”. If I don’t do those things and I will probably put policies into motion that I don’t even realize the ways that they could be harmful because I’m writing policies from my worldview and, as much as I studied the law, I could still only write laws that were around my own experience, around my own worldview of “Here’s how things should work”. So as much study as you have done, it can’t counteract all of the years of experience about “This is how things function and how they work and how they work for me”.

We need that space of people really understanding their impacts, and we need that space of even more people coming from the experiences of the communities that they’re actually from, working in and serving in, so that we can then see that relationship building and laws and policies that are passed, that are reflective of the experiences of the folks who most need the changes in laws and policies right now.

Mallory: We could keep talking about this for a very long time. I’m interested in your perspective on “Okay, so these problems are big and I also think just how much of this work is holding two truths at the same time and existing in a great gray space with a lot of hope and belief around what’s possible”. What are some of the biggest barriers for individuals to engage in this process? Particularly women or people of color. In order to increase representation, there’s these systemic issues that need to be addressed. And how can we support individuals to be able to participate? How does funding play into that? 

Taylor: Absolutely. So as we think about folks who are coming at, specially the space of elected leadership who are not the usual suspects of who’s going to be running for office, one of the first things that I’ve noticed from campaigns is there is this shift of the language on that “You are not doing this alone”, that we have to get really, really good at because for a lot of folks from communities of color who are running for office and for a lot of women, they do have to run this race that is about their name on a ballot and them being there.

But also the way that we know that society functions, they are representative of all of these other folks. That’s a whole additional set of pressure that comes with running for office when you are a woman and a person of color, but leaning into that and really building communities around those candidates that support them fully is super important.

One of the things I think about a lot is that in training folks to run for office and in fundraising, we use a lot of the terminology of the circles of benefit for fundraising and that’s used in non-profit work as well. You start in the center with yourself and you basically work out into these concentric relationship circles.

So you have to ask for money first from your friends and family. And that should be a big chunk of your money coming in as and then you’re going to move out to people who are acquaintances in that space. And then move out to people who you share ideology with, moving out to people who are trying to back a winner, and then getting up to people who are trying to take out your opponent and that sort of thing of raising money. Circles of benefit is incredibly smart for helping people visualize fundraising asks and it is incredibly important for everybody to ask their friends and family.

But we are perpetuating some systems when we tell people that that’s the way that we fundraise, because we are assuming a certain level of wealth within that first set of circles of your friends and family. And what if you cannot raise a high percentage of the budget that you need to be able to run for office and win from that circle because they will give you everything they can, but that number is small.

So we have to think about “Okay, so how are we then creating the communities to be a closer circle around the values of getting more women and people of color into office so that we can come in even closer to those candidates and make sure that they have the resources to be able to get their message out, to not have to struggle so much within the campaign space and do things on a shoestring budget and not be able to talk to as many voters as I can”, cause that’s what money means in the election. It means the ability to be able to talk to voters. 

We have to shift our conceptions and not build so many frameworks on the ways that elections have worked in the past. And instead, figure out how do we build better and stronger communities and put our own resources into the game on those fundraising biases.

Candidates will go through when they do their call lists. I have sat with candidates doing that work, and I have watched folks, especially women of color, call through the list. And it is painful whenever they’re asking some of their families for money because they know “Yes, this person will give it to me and they will do it with all the love in the world and I know the things that they may be sacrificing for this next week, because they are giving me this amount of money”. 

How do we make sure that we are then saying “Nope, in this new paradigm, we’re going to build systems where we’ll put in the investment because we believe in a world where more candidates of color are in elected office, where more women are in elected office, and we believe in the outcomes of that, we believe those are in our self-interest”?.

For folks who have means, they will do far more donating into those races, even if they don’t necessarily know that person, even if that gift is not going to mean that they’re going to become your best friend in your open ear. Instead that gift is going to mean that they are able to talk to more voters and ideally be able to make better decisions when they get into office because of their lived experience.

Mallory:  I could not agree with that more, it actually aligns with how I teach fundraising because there’s a similar thing that happens in nonprofit often, where everyone tells people “You’re starting your nonprofits with friends and family rounds” and it drives me bananas because that is immediately going to create sort of problems in how nonprofits are formed. But I think what you’re talking about is you start with alignment, which is what I teach: finding the people. When you were sharing these concentric circles, part of me was like “Man, start with people who are trying to unseat the other person, they’re so aligned with you!”.

Especially, think about things from that mutual benefit space. If we think about it, now I would start with the value aligned people, but I do see that as a low hanging fruit opportunity because there’s this real mutual benefit of engaging folks in that conversation.

I really like how you wound that back and said, okay, when you look at these sort of old models of doing these things. The system is in here too, you know? How do we start to think differently about how things can work so that we’re addressing these issues at the root causes? Do you see a lot of folks who are interested in being more engaged, but they’re like “I just can’t make those phone calls. I could do everything else, but can someone else make those phone calls?” Is that a thing? 

Taylor: All the time? Like “Can I make it over text or emails?” It’s an incredibly vulnerable spot to sit and make phone calls. And especially with the exception of call time where I’m going to carve out two to three hours and just going to sit, working through a list where a lot of people are going to tell me no, or they’ll tell me later, or they won’t give me the amount of money that I was hoping for. And you’re supposed to be hitting a certain amount at each of those call time windows in each hour. That is incredibly hard. 

That’s where also that community space comes in, because it is harder for some folks having somebody else there who is going to pick you up through that incredibly vulnerable time while you are doing it, especially as you’re building the habits of doing. It’s so important. Call time coaches and having a friend who will sit there next to you in call time are some of the most invaluable things in campaigns that people just don’t even think about of you need somebody to make a funny face with you when you’re sitting on the phone and getting another no, and wanting to hang it all up and just like, “Nope, this isn’t for me”.

Having people see on the front end that they can build in those supports to running for office. This is really, really important. And then making sure I’m really glad that I work at an organization where a lot of times we’ve built in a lot of those supports and we’ve got folks who coach people through call time. We’ve got people who will actually stick with them through those really hard times. 

Mallory: Oh, my gosh, the nonprofit sector needs that too. We need call time coaches. It’s so hard, you know, I think sometimes I hear fundraisers say, “I feel so overwhelmed. I’m feeling so exhausted all the time and I’ll have people come to me. They’re like “I’m not even overworking time-wise, I even reduced my hours to 32 hours a week and I’m still so exhausted all the time”. I think so much of that has to do with the fact that fundraising is a numbers game that inherently involves a lot of rejection. I think for small organizations, just like with political candidates, it feels so personal.

And that is just a really exhausting place to be in. I think, unless you’re able to really shift your mindset around the fact that this is a practice of organizing and is about bringing people in and giving people an opportunity to engage and make a difference. The thing I so appreciate about LEE is that while I know your success rate with first-time candidates is so much higher, I think your sort of framework and expectation setting around the purpose of campaigns is a big reason why I wanted to do this series. Is for folks who are not in your world to recognize that like campaigns are about so much more than the winning and losing at the end of the campaign.

From an investment standpoint, we need as the general public to think differently about giving, because I think really getting to know all of you I was like “Do I want to give? Are they going to really win?” And then it’s like, wait “Why have I been trained to think that way?”, but learning about how much happens within a campaign, the value that’s created, and the organizing that’s happening and realizing that there’s this perception that organizing bodies within a community are the only things organized. And so they feel like a-nice-to-have.

The thing that people need to recognize is actually things are already organized in this power structure and we just don’t see it happening because they are in positions of power and the web has been created. So when we’re organizing in community, it is to address something already organized that is not working for everyone, that is disenfranchising people, that is harming community. And so it’s not some extra thing. 

Taylor: Absolutely. I think we talk around it, the power mapping space. When dismantling the power map you’re going to try to shift the thing that already exists, but literally have been in front of whiteboards creating that rep with people and saying “Okay, so then who here? How was this decision made and how does that work?”. That’s this big web. And then when you start into the organizing space, you’re basically saying “Okay. So then how do we shift this? Where do we go? And first, how do we move piece by piece, being able to change this so that it operates well for more people?”. 

And that’s a lot of what campaigning is too. It’s being able to say “Okay, what are the current votes that exist out there? Who’s been voting? Is it everybody who lives here who has access to be able to do that? How do we create more access to be able to have more people having a seat at the table? How do we organize those folks to then be able to come in and really shift a nervous system of power?”.

And so, yeah, I think you’ve said it well, there’s a web, and if people want to be a part of saying “I think it should look different”, then the way to get into that is to get into community with other people to give and spaces where they are in a shared values, alignment space with candidates and it’s going to actually change what the system looks like. To be a part of that collective people power, to be able to shift that power. 

Mallory: Well, thank you. I could talk to you forever, but tell folks how they can find you, how they can connect with you. I like to invite every guest at the end to share a non-profit that’s near and dear to their heart for folks to go check out and give if they can. So I’ll make that invitation to you as well. 

Taylor: Well, you can find me on Twitter. I’m @TaylorMStewart. And so that would be the way to follow me. I’m using mostly retweets though, honestly. 

And as I think about nonprofits, I actually got the opportunity to serve on their board and their work right now is around Strong Schools Maryland, which is a group who really helped spearhead a campaign across the entire state to change the funding formula, to do some more of this equity based work.

They are now making sure that the implementation actually looks to serve the communities that it’s geared toward communities of color, english language learners, and students who are growing up in low income environments, making sure that our state’s education system that is vaunted oftentimes is being the best in the country or one of the best in the country actually, is that for all kids. Strong Schools Maryland is where I’d say support.

Mallory: Awesome. I’ll make sure all the links are below as well. Thank you so much for joining me today and having this conversation. This 

Taylor: This is great. Thank you so much.

18.3 Building Power, Organizing Our Communities and Moving Money with Taylor Stewart

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