Fundraising as Organizing: EQME's Chris O'Connor on Building Community

Chris O'Connor fell into fundraising almost by accident—laid off from his job in 2014, he took a chance on an open Development Director role at Equality Maine despite having no professional fundraising background. Five years later, he joins the podcast to unpack what development work really looks like day to day, and why he sees it as an extension of organizing rather than a separate discipline.

Chris walks through how he leaned on existing community relationships and trusted volunteers (many former students he'd trained) to rebuild EQME's signature events, including transforming the organization's annual dinner into a now-720-person gala and standing up a brand-new golf tournament after one Facebook post drew eight volunteers. He talks candidly about the anxiety of "making the ask," including a bombed first fundraising pitch and a save-the-moment story from a fundraising cruise, and how staying anchored to the organization's mission and community made asking for support feel more natural over time.

The conversation also covers how he structures volunteer planning teams so people can plug in based on skill and capacity, why he intentionally builds teams that reflect the community they serve, and his advice for anyone just getting started: get clear on your "why," identify your first believers, and don't be afraid to try something new and let go of what isn't working. He closes with a reminder about avoiding burnout in this work, since sustaining the organization means also sustaining yourself.

SHOW NOTES

Chris O’Connor shares with us his 5 years of experience as a development director at Equality Maine, one of the largest LGBTQ advocacy organizations in the state. Chris came to Equality Maine with a boat load of experience organizing and working with teams, but had little to no fundraising experience. He shares with us how he learned the ropes, the highs and lows and how he has centered his development work around the community and values that his organization serves. 

Equality Maine – To learn more about Equality Maine, the work they do, and their upcoming events, visit them at equalitymaine.org .

Maine Association of Non Profits (MANP) – Is an excellent resource, they also have a very robust jobs board if you’re in Maine and looking for work in the non-profit sector.

Association of Fundraising Professionals (AFP) – A great resource with lots of tools and learning opportunities, they even have a fundraising dictionary!

• Transcript

  Benn Marine 0:09

  Welcome to the Ocean of Organizing podcast, where every Thursday we explore what it means to build community and create change. Today on the show, I have My name is Chris O'Connor.

  Chris O'Connor 0:20

  Uh I'm the development, I use he, him, and his as my pronouns, and uh I'm the development director for Quality Maine.

  Benn Marine 0:25

  Chris shares with us some insight on how to fundraise and do development work through the lens of organizing, through building community and working to create change and always keeping the values of your organization at the forefront to not just motivate yourself but also your volunteers and to drive those development dollars. So without much further ado, let's dive on in.

  Chris O'Connor 1:14

  Back in 2014, I was laid off from that job. And uh at the time I was one of the, we were in the midst of co-founding um Pride Portland um and working with a bunch of folks in the community around organizing to keep Pride alive back in 2014. Uh at the time, Equality Maine was our fiscal sponsor. Uh, and so I had a really good working relationship. I had been involved with Equality Maine for a long time as a volunteer uh with the marriage equality campaigns, both in uh 2008, 9, and then 2012. Um, but had kind of taken a little bit of a hiatus uh and then got involved with Pride. And so when I got laid off um in this weird kind of uh kismet kind of a way, I a quality main was looking for a new development director. And um I was close with the with the with the executive director at the time, Elise. And she called me and said, Hey, I think you'd be really good at this. And I was like, I don't know a thing about fundraising. What the heck are you? And she's like, No, you do. And I was like, but uh development, like no, I always laugh about this. Like nobody ever oh, I shouldn't say nobody, but I haven't met the person yet that went through high school and college and says, I want to do fundraising. Um, you know, I always I we just did a training with our new leaders uh on action planning and and and kind of they did a session on activism work and then I led them through kind of how do you actually take an idea and lead it to to fruition. And I introduced myself as a development director, and I was like, who knows what I do? I asked them, and nobody knows what the heck a development director is. You know, I direct development. What does that even mean? Um, and so I was honestly at that point, I was like, what does a development director do? I knew fundraising and you know, but not really much else. And so I took a look at the job description and I was like, well, I I've always been the kind of person that can kind of figure it out. Um never planned a pride parade or a festival before, but we figured it out, you know. Um, so I uh I threw my hat in the ring and said I filled out a um I updated my resume. I was on this little bit of a hiatus because I was laid off. I didn't have anything to do. I'm like, well, couldn't hurt. Um, and went through the interview process, and before I knew it, I was a quality man's new development director. Um, so it's a very interesting story. I think most people um fall into development work that way. It's you know someone. Um what I've found is at the core of development work is relationships. And so for me, I've been a part of the Portland and Maine community for 21 years now. And if the relationships are there, if you have the ability to connect with folks in authentic ways that you know, that attach to things that you believe in. Um, anyone can do development work. Um, I'm now, I wouldn't have said that five years ago, uh, but now I I I say it over and over again when I talk to people about this work. When I just trained, you know, 55 12 to 17-year-olds on on how fundraising is an important part of activism work and how that development work and and development, we can talk more about this too, but development is so much more than just fundraising.

  Benn Marine 4:57

  Tell us a little bit more about development in all that it encompasses. Because I think some people think, like you said, like fundraising, like, okay, actually somebody who is probably maybe picking up the phone and asking for money all day long, what does it actually look like? Like, what does a typical day look like for you?

  Chris O'Connor 5:11

  Um, I I was actually laughing yesterday. Uh I needed like seven different identities because um I started off my morning um working on a new script for our um our street canvas team. We have a a a team of young people um who do fundraising work for us, um, who you're pretty familiar with. And so we were we're in the midst of training them on talking with folks about supporting our um our safer schools initiatives, our work to create safer and more inclusive schools for LGBT youth across the state. So I started off my day um working on and and finishing that script. Um and so uh then I had a meeting with folks from Sugarloaf Mountain, and we're had an initial planning meeting for our LGBT ski weekend that's coming up in January. And then I had a meeting with some uh community volunteers who are working with us to launch our first ever uh out on the green um golf tournament. That is our first year. We're launching that in October. So I had to shift focus to that. Then I had a meeting with a bunch of drag performers to get ready for or start the conversations around our great pumpkin ball and what that's gonna look like. Um and then I go back to my desk and start getting back to emails because I was in meetings all day long. Um, today I had a meeting with folks from Portland Innovations to talk about a partnership between us and them, our kind of ongoing partnership with them to support an event they have coming up September with a queer performer who's coming to the state theater and talking about how we can elevate that event with our members. Um, you know, we're fielding um it's really kind of all over the place. Some of it is focused on raising dollars to support the work that we're doing. Some of it is about relationships and partnerships and in supporting and building our community and keeping our community strong. Um, and so it's really, I talk about it, it's developing the the roots of our organization and making sure one, that we're strong, but two, that we're doing our part to help keep the organizations and people in our community and leaders in our community also strong. We have that obligation as well. And so from a development, when I look at developing or or directing development, that's really um it's from volunteer uh engagement in the organization in our work and making sure that you know I can sit in my office and plan away all day long and pick up the phone call. When we're engaging people in our community that believe in our work and our organization and doing that work, we're so much more effective. We're able to do so much more.

  Benn Marine 8:04

  And I'm curious, I kind of want to back up a little bit. You mentioning how you had never done this before, and now, you know, just describing the last couple of days, you know, in meetings, talking about different events and uh you know other opportunities to cultivating community with folks. How did you learn, how did you learn the way?

  Chris O'Connor 8:20

  Like what resources did you go to, or if you know if you had advice to give to maybe somebody else who's starting out as a development director or um you gotta dive in head first, um head first, feet first, like it you just jump right in. Um and depending on the size of the organization, um I I have a lot of now friends um who are in the field and in in doing development work, and they're friends from um organizations across the country, but they're also friends from organizations here in Portland and across the state. And so I've just kind of one established first like who are some go-to people that I know they're doing the work and talk with them first. Um, the other piece that was really important for me was spending time um with our board members right off the bat to find out what their investment in the organization is. Um, because as a staff member of an organization, it's it's critical to know what the people that are most connected to the work. And so it's your board members, it's your key donors, it's your lead volunteers who are engaged in everything. So I literally just sat down and listened to folks. I asked a billion questions, probably to the point where it was annoying, where like, Chris, like, stop already. Um, but I've also part of it was just jumping in and trying things. Um, we were at a point as an organization where we really needed to try some new things to re-engage folks in our work. The the reality, and you know this because you were part of the work, but when we were um when we were post-marriage, there were a lot of people in the community and and supporters of ours that were like, yay, we're done. Like, what woo-hoo. And like, yes, there was this component of celebration, and we had conquered something that we'd been working on as an organization for about 10 years. Um, but it was so short-sighted to ever think that the work was going to be done. And so a lot of it was figuring out what where those people were at too, and figuring out like, how do we how do we re-engage those folks? And so the only way to do that, again, is from relationship building. And so I knew a lot of people, so it was turning to people in the community that I knew best um first um and pulling those people in. So, like the event planning thing, I had spent 16 years working at USM training student leaders across campus for all of those years on how to run organizations and how to plan events and festivals and protests and rallies and all this other stuff. So, what I did, and you're gonna laugh at this, like my first uh the first year that we when I started, we turned our annual dinner into the into what we now call the gala. Um, I literally that whole committee was all former students at USM because I knew those were people I trained that I trusted, and so was Ashley McCurry um and uh Marphine uh Chan and Um Emily Fitch and folks who are now going and doing crazy, crazy things in our community. But those were students of mine that uh Andrew Cantillo, who now just moved to California to work for a new company there, like like but I brought them all in because I trusted them and I and I knew them and they knew how to work with me, and so it was surrounding myself with people that I knew had my back. Um, and so we were able to to start doing some pretty new things for the organization. The board, um the board knew I I'll uh going back, I knew that um it came down the final interview process was between me, someone who had no fundraising, professional fundraising experience, um, but had the connections to the community, um, and someone who was had a lifelong resume of organizational work and fundraising experience, nonprofit work and and the board put their faith in me. And I knew that that they they put themselves on a limb. Um and I really to this day am so grateful for that opportunity because I knew I knew they were putting themselves out on I was really upfront about it. It was not I I wanted to paint a really realistic picture of what I thought I could bring in in a new a new frame of frame of reference into this work. Um but that first year, like every time I was like, we're gonna do this, the board was like, What? I remember um the first gala, I was like, we're not doing name tags. And they were like, What do you mean we're not doing name tags? And I was like, I don't want an event where everyone walks around and stares at each other's chests, and you know, and and that's the only way that they're gonna interact is by, well, I don't know you, so I'm not gonna say hello to you. I said I I wanted to change the way people interact at our events to make it more authentic. And if I don't remember your name, I'm still gonna introduce myself. I'm gonna say, I forget your name, and I'm gonna look you in the eyes and still say hello and and acknowledge that we're both in that place. It was just this little like kind of psychological shift. Um, and so now we never do name tags anymore. And and I think people are okay with it. It's a little just kind of little tiny example of I didn't know what the heck. I mean, I I I knew I knew what I was doing, but it was just about taking risks um and trying new stuff.

  Benn Marine 13:57

  Well, I'm curious, what were some things that you're like, oh my gosh, yes, this was awesome, this worked really well, we're gonna keep doing this. And then what were some things that were like, oh gosh, we are never doing that again?

  Chris O'Connor 14:08

  Oh, I need a second to think about that. I mean, the the concrete, like, we're not doing this the same way was the dinner. Um, I knew that um for me, and and again, the dinner was this, it's happened every year. The organization has been here. We're now in our just in the midst of celebrating our 35th anniversary. The dinner has happened every every year that the organization's been around. It started with I think 10 people at a restaurant, and then it moved to the civic center in Augusta, and and now it's at the Holiday Inn. Um, but when I inherited the event, it was uh it was a lot of talk. I had heard it's a lot of talking. It was a black curtain with the podium at the Holiday Inn, and and uh and I just knew that our community wanted more, and in my eyes, as the statewide LGBT equality organization, that our community deserved more, and that we were asking a lot of people to come to something um and support our work over and over and over again, and that we had an obligation to deliver a high quality event um that people feel good about, that gave people gave people the opportunity to interact with each other. And while the dinner did absolutely do that and it's celebrated, I don't at all want to imply that anyone before me that was doing the work, you know, was not, I mean, it was again what was needed at that time. I just knew that we could breathe some new life into that. And so as a result, we've grown the event. My first year, the year before I started, the event was at 380 people. Um this past year for our 35th anniversary, we had 720 people, and so it's really we've engaged um um community.

  Benn Marine 15:58

  And and you guys sold out like two weeks early for that event, too, I think, if I remember right.

  Chris O'Connor 16:02

  Every the past three years we've sold out um because the Holiday Inn always tells us, nope, this is how many seats you have. And and so yeah, we've we've sold out the past three years. This year we sold out about two weeks in advance. Um I always every year I'm like, can I fit more tables in here? Because I I I don't want to turn anyone away. And so um we've this year our committee members and and and again the other piece of that is we've got a team of about 20, 25 people that work from November through the event in April to make that happen that are all volunteers, and so yes, I do the big picture coordination move making sure all the pieces fit together, but it's really driven by our community. We've had 276 um items in the in the silent and live auction this year. Those two pieces together this year raise an additional sixty thousand dollars at the event. Um and because we made fun raising fun, you know, that's so cliche. Um, but it's what you need to do. I mean, we it's people want to be there, they're there because they support the event, and we're just providing them a vehicle to do that in a fun, creative way, and they get something fun, and so it's it's really kind of cool. But so it's you know, we couldn't do that without the the amount of people that are involved. And so that's been one of the things that we've really how we've been able to grow that event, and and now like I've already had people contacting me about reserving tables for next year's event. Like, it's pretty amazing, like it's it's become the the event to be at in the spring. So um, so it's good, but it it was a good example too of you know, how do you tweak something? We I've had many people tell me we need to move it, and I'm like, no, I don't want to move it. Like it's there's an intimacy of having whether it's 500 people or 720 people, and then hopefully next year 750 people in that ballroom space. I mean, and so I don't want to mess with that. And there's there's a lesson to be learned, and if it's not broken, don't fix it. Um, and so I don't want to move the event. Someone's like, well, get rid of dinner. I'm like, but people like the opportunity to sit together and and to if you take out tables and chairs to fit more people, it's just a bunch of just mingling, and it gets to me that gets monotonous. So I don't wanna I don't want to change the event for the sake of just changing stuff. I want to always be intentional about it. And so from our standpoint, that's really important. And and again, you know, how do you build upon something as opposed to scrapping something and just going a completely different way? Um there was a couple things like there was a there was a pride event that just wasn't doing well. We had a Bangor event that went a couple years that without an office in Bangor was really, really hard to sustain. So we you know, we took a look at at where there's holes in the community, where there's needs, and and and tried our best to assess, you know, kind of how do we how do we how do we fill those those needs for the community? And I think organizations have to constantly do that is not just be like, I have a great idea, you know, I'm just gonna do it. Like, no, you you know, or scrap an idea. So we didn't really scrap things, but we morphed things. And so what was an annual banquet, sit-down dinner in Bangor has now morphed to a holiday celebration. And we still do awards, and we still it's still important for us to be there and be present in Bangor and lift up people and organizations who are doing really powerful work. We just do it in a different way, and by doing it around the holidays, it becomes this fun evening. It's more of a cocktail party. People get to mingle. We still do the awards, so it's it's it's really, really worked well. Um, also in Bangor, um, there was nothing. We do a lot of our events in Portland because that's where the most people are, that's where our offices are. So it's easier to do events in Portland. Um, it's where we have relationships with sponsors and company, you know, businesses. Um and so for in the Bangor community, it's a little bit tougher to where we're we're we're there and we're doing events probably six, five or six times a year, but we just don't have that regular, you know, presence with folks. Um but there was a need for uh we do a a big um after party for Pride Portland. Um we throw a big dance party and um just 800 people like it's just it's amazing. Like it just is it's again, there's needs in our community that can be met, and that's one of them. And so it's it was been we were we were really excited to take that on. Um in Bangor, there was no evening party. There was a there was a chem free party for young people. And some of our our adult members came to us and said, Hey, you're doing this party in Portland. What about us? And so for us, it's also really important when people express a need that I'm always the kind of person like I wanna so we worked with folks in the community and said, all right, let's do this. So now we have a Bangor party um that we do as you know, the Pride After Party for Bangor. And we get a hundred this past year, we had 175 people. And again, it's not we're not ever gonna have 800 people, you know, it's different communities, different worlds. Um, but it's a pack space and people had a blast, and we had drag performances and DJs and just a really good time. And so um, and those are you know it's another example of two of development work, not necessarily just being about raising dollars. Um it's uh again, it's a little cliche, but there's there's so much value in what's called friend raising and that connecting people with your organization using social community building time. to reinforce the work that you're doing. And then it's not always an ask. It's not always a we need you. Yes, there are definitely those times and and that we have a captive room and and people engage in our work and we have to ask. It's just part of how we have to exist because as I always talk about there's no magical money tree somewhere that's just producing. You know, the reality for nonprofit organizations is that you go through your year and then you start again. And you don't have this big cash surplus. And you know some organizations, yes, have um have endowments that and and we're just not one of those organizations. So for us it's a constant process of of engaging people in the work um but in an and then moving them and moving them into becoming volunteers and moving them into becoming donors and moving them into into becoming event attendees and and and and repeat sustaining donors. You know it's that whole process of of how you build a sustainable organization.

  Benn Marine 23:03

  Yeah so I'm curious for folks that maybe are maybe doing their first event or maybe they're just starting an organization and they're not quite sure where to start do you have like a do A B C like just to get started or any tips for folks just getting off the ground?

  Chris O'Connor 23:20

  The biggest thing is know who your audience is. Like really really think about and and even more so than your audience that sounds so so um almost technical or removed from but know who your community is. So again it's that you know talk to your board you know find out the things that are it and if it's you know and be really clear about what is it that you're trying to do because when you're clear what you're trying to do you can then create a plan. This is the training I just did with with our our new our young leaders and it applies across everything is we lead to create change for the benefit of the common good. And so nonprofit organizations all of our work none of us sit in our offices all day and all night and on weekends because we want to maintain the status quo. We're all working towards what our mission is for our organization. We're all working to to move from point A and move and make progress towards point B, whatever that is. And so whether it's an event whether it's a a meeting whether it's a a fundraiser whether it's a call night whether it's a volunteer action all of those things have to fit into what that that plan is what what and so you have to figure out what am I trying to do with this event? Am I trying to raise money to support a specific program a specific initiative? Am I trying am I building community? Am I is it just uh I want to introduce people to a new project we're doing is it I want to whatever it is that you you've got to establish why am I doing this first and be really clear about that. And then the next step is is to establish who your initial investors are and in investors are not always just people with dollars. And so it's not always just sponsors it's not always just a host committee it's not always your investors are the people who who you can bring in establish some level of common purpose with that they believe in what you're doing. And when you can do that you then increase your impact tenfold and it's this idea of it's you know the idea of pay it forward where if I do something good for one person and then they go do something good for three other people and then those three people do something and it it just expands. It's the same idea again I said earlier if I sit in my office could I plan a golf tournament probably I've never planned a golf tournament I don't know the thing about playing golf but I can Google it and I could you know I could figure it out because I have that that it's something just that for me I could figure it out. I didn't want to do that. There was a call for in our community there was a bunch of people saying enough about these bar events enough about the you know food and getting dressed up like we really like to play golf and there's a lot of people in our community like to play golf and it's a great way to raise money and I was like hmm okay so instead of me sitting in my office and Googling how to plan a golf tournament I turned to people actually I just posted on Facebook. It was like hey who knows how to play golf who plays golf and might have an interest in um helping us um or even exploring the idea of of launching a golf tournament and literally within a day I had eight people say I'm in I'd love to help some people I didn't know um but oh I knew they were on Facebook but I didn't really I didn't I didn't know them. I didn't know they played golf I didn't know anything but so I we just extended the invitation and all of a sudden I now have a committee of people that are out working on planning a golf tournament. And so it's that you know and yeah that's some of it can be tough sometimes because you're managing you know you're managing volunteers out doing stuff on behalf of the organization but I would rather spend my time doing that than sitting at my desk by myself because the impact of that so they're now out spreading promoting it they're all they because they play golf they're promoting it to other people who play golf and it's it's pretty it's a really cool example of how you take a little seed and and the seed came from just me being at a friend's birthday party and a group of women saying like what about a golf tournament like and so and then and I held on to that and I waited until the time that I knew I had some time to kind of um plant a seed and then pour some water on it and kind of you know get it going in the right direction. And I need to stay hands on because I've got to make sure that you know they're feeling supported but we're moving and it's happening October 3rd we have got our first ever golf tournament coming. So it's pretty exciting. So anyway um again a long-winded answer to your I just think there's some opportunity for folks to to start to address where there's need and then to just really make sure that you're being really intentional about meeting that need and then the other stuff starts to fall in place and you will find that other people start to you know get excited about it share in your excitement own it that's when the volunteer you know the volunteers start to come in and you really just start to build something that um that people believe in. And then the other thing is if it doesn't work you can try it and then move on there's no you know it the big from a fundraising development standpoint my thing is is that and the expectation is that I can't lose money you know and so that's the that's the only I think the the detriment not the detriment but the some of the additional stress about trying something new is you're gonna put yourself out there and then you got to work your butt off to make sure that you at least break even because I never want to lose lose money for the organization.

  Benn Marine 29:44

  So so far in five years we've been good. I'm curious what is that uh where where it sounds like there's so much community engagement, what does the support look like? Like how do you balance letting folks lead and drive but also making sure that they feel support and have what they need? Like is it like weekly check-ins or or what how does that manifest?

  Chris O'Connor 30:05

  Aaron Powell I am a big fan of the planning team um I I hate calling things committees no one wants to be on a committee. And so for me it's about engaging people in a collective planning process um that starts big and so or or bigger um depending on the scope of what you're doing. I mentioned that gala we've got about 25 people there's two different teams that work on that plan there's an auction team and then there's a gala team so we start big to make sure that one everyone's on the same page you know it's really important to make sure that everyone has the same vision um of where we're going where what's what's what's the goal what's the and then even more important is that everyone shares the same value uh and kind of value set of what of what that whatever you're working on is so for example um you know whenever we start the well I'll use the great pumpkin ball as as an example where we've got our planning team that we had our first meeting a couple weeks ago and that first meeting is the initial investment in buying I did a bunch of hey I think you'd be great at this you know would you like to join our team you've been a part of this you know you helped plan the gala I'd really love your help on the on the pumpkin ball yeah great some people are like what the heck's a pumpkin ball um so we talk about that it's our annual Halloween party um which is our big fall fundraiser um but I want people to know what's going on for the organization so we always start off with um you know the most recent updates what are the successes what are the challenges we're facing I also want people to know about why what's the history of the pumpkin ball and why what they're about to commit spending their time on working on is critical to the success of the organization moving forward how has the history of the event impacted the organization how have the volunteer hours that people have put in for years past um benefited the organization how what why are we still doing the pumpkin ball? What's its impact on our community? What's its impact on the organization? So for example with the pumpkin ball um we're specifically raising funds to help us expand our work to create safer and more inclusive schools for LGBT youth into more rural parts of the state this year we're working really to reach into um new places where we haven't been places where schools have limited accesses to access to resources and so we want to be able to raise the funds that help normally a lot of times schools will contract with us to come and do whether it's a policy consultation or a uh or a training with teachers and administrators so we're working to to be able to have a a a pool of funds that allow us to go into schools and provide those trainings at no cost to those schools. So the pumpkin ball is specifically raising funds to help us do that. So people feel an investment about there's a reason yes I I like planning events I like I love Halloween I'm really good at decorating um I I love a good costume contest I um I love um I love drag performers and burlesque performers I want to be a part of that I'm a good stage manager but I want people to know the core of it always stay connected to the mission of the organization and to me when you lift that up people feel and and you constantly lift that up and remind people and keep people updated they're engaged in the organization and again it's more than just planning a Halloween party you're engaging people in the work of the organization and the sustain the long-term sustainability of the organization. So the everyone starts off on the same we all have the same information we all have the same vision and then it's about engaging people in the in the big picture planning making decisions it's the what's our theme going to be um you know what in some stuff you know it's important that the organization doesn't let go of because it's critical to the to the mission or value or or of the organization. So there's some things that I can't let go of sometimes I'm also really transparent about those things. But when we're talking about performers when we're talking about ideas for like I said themes or music or you know it's a it's about pulling people in and giving them empowering them to have a voice in the planning process. It's also really important to make sure that your planning team is reflective of the community that you want to participate in and benefit from whatever you're putting out there. So for us it's about making sure that it's that you know if you just have a planning team that all looks like each other and all share the same gender identity or same the same sexual orientation like it's just you're gonna end up with an event that reflects the those people. And so for us to put forward an event that is truly reflective of the organization and of our community we want to make sure that the planning team reflects our community too. So um so that's important and then it's really about asking people what they want to what one their skill set is two what their time commitment and capacity is um and and and then three is really what's their personal investment. Like what are they willing to do? And then it's matching them with with the right opportunity. So I'll give one example we went through and we typically have you know several sub subteams within the planning team. So there's a an atmosphere team and there's a costume contest team and there's a marketing team and there's blah blah you know on and on in terms of the organizational structure. I had a young per a younger person who had been involved with the gala they're kind of shy in meetings they don't they don't talk up a lot in meetings but they're always there and she came to me and said hey I have a lot of experience with stage managing and I would love to be a part of that if there's a an opportunity for me. And I like lit up I was like I would have never known that um and I was like absolutely of course and so it was again having that creating an atmosphere where people feel like they can one have a voice to with their voice you know committees are and work teams and and and group meetings are always tough because sometimes there's a more dominant voice in the group and so not everyone feels comfortable saying I don't feel comfortable with that. And sometimes there are people who are fine but it's again making sure your process is open and realizing you represent the organization and that none of this is about just me. None of it is about any volunteer it's about the organization. So so your initial question was kind of how do you balance the the volunteer engagement and so for me it's being really clear about what expectations are making sure that everyone has as much information as I have at any given point that I'm really transparent sharing that and that they also have access to me as much as they need me. So typically what ends up happening is we'll have a first initial meeting we'll decide who wants to work on what and then our second meeting which is coming up this next week we actually will break into those teams um and then I will make sure that each of those teams I'm gonna ask them to create what they think their work plans need to be and then what I'll do is I'll check in with each of those teams and the next week I'll schedule a meeting with each of them. And so it's it's time it's time consuming because there's sometimes like I could probably plan this by myself easier but it's just not how I want to do it. And so luckily I have personal capacity and ability to kind of manage those different pieces and knock on wood um you know we we've had really really good luck with people doing what they said they were going to do you know and again I I really really think that's why I spent some time talking about that that beginning part of the process is so important. Because when people understand like if I don't do this there's real impact for me not doing that. Um and then it's also you always have to plan for for someone not doing what they said they were going to do and you always have to allow for the emergency plan and um but we we typically do pretty well it's good.

  Benn Marine 39:42

  What what what has been the most challenging whether it's part of your role or just part of working at a nonprofit like what is the most challenging and how do you how how have you overcome that?

  Chris O'Connor 39:52

  You know I think the when I first started the reality I I mean the reality for development folks is that literally everything you do is an ask. Literally everything you do is an ask. And whether it's an ask of someone's time whether it's an ask of an in-kind donation for a service um uh a talent uh whether it's photographers ASL interpreters um a piece of scenery a lighting rig what you know it I mean the things that go into the event pieces definitely everything's an ask um and then on the fundraising side of things it's it's all it's it's every almost every conversation is some form of an ask and it's interesting I remember going to a workshop when I first started I went to a bunch of workshops too that was one of the the things that was really helpful the main association of nonprofits um there's also the association for professional fundraisers or for fundraising professional things called AFP um I went to a bunch of they have regional conferences and day long trainings so I just kind of engulfed myself in that stuff too um but I remember one of the workshops was we have why is it that we have no problem asking people to donate their time but we freeze when we have to ask them for money and I remember it was um I used to have a lot of anxiety around asking for money um and it wasn't I you actually do trainings on this because I've been a part of them where we talk about and you talk about um you know kind of deconstructing our own issues with money and and and how we understand how that impacts you know our ability to ask others for money. I'll never forget my first um first event I had started in the end of August and we had house party at the first week of October that I was responsible for and I had to make the ask um and it was after four people talked before me that all like spoke like for three or four times the length that they were supposed to they covered all of the talking points that I was going to use in my and so I was like shit what the heck do I do now? And I froze and I completely bombed um and I had like former students and board members and all looking at me and I remember just being like they're looking at me saying what the heck did we do how did we hire this guy he can't raise a dollar um I raised more than a dollar but it was not it wasn't good and I remember literally like running out of the room and just being like I can't do this. And I also remember waking up the next day saying you got to snap out of it. You got to figure out how to do it and and I did and I and and every time every ask I still had the anxiety I still had the but every ask got easier and and when I think the changing point for me you know I've talked about like I don't know that I could do this work for I I know some people who could do fundraising for any any issue any organization I for me it's the it's the passion for two things. It's the passion well a few things it's the passion for the organization that I I I truly wholeheartedly believe in. I I feel so honored every day that I get to do this work in in in the the long history of 35 years of people who've been doing it before before me and us. But I also the passion for our community The passion for the fact that there are people that I I live a life of considerable privilege because of the people who've done the work before me, that I now feel that I have capacity to do the work that I do on behalf of others in our community who are still still fighting to live their true authentic lives. Um and so for me, like that that's all real and that plays into every single ask that I make. Like I ch I and and when I first started, the anxiety over asking for money overrode those core values in why I do this work. Now those core values are so much stronger, and and I don't have the inhibitions that I did before. And so now I literally can ask for anything and everything and and just laugh it off when I don't. And and and people know, you know, one of the one of the downfalls about development work is especially when it's within your community, like I'll be out and I literally will watch someone like make eye contact with me and change direction because like he's gonna ask us for money, he's gonna ask me to come to some event or something. So I have to, you know, one uh another challenge of the work is that the boundaries between um professional and personal life, especially when you're doing work that is so core to your identity and your in your like literal everyday existence. And so like I'm gonna be at Blackstones, and there's times when I'm like, I don't want to talk about conversion therapy right now. Like I'm just having a drink and I just want to watch people play pool. Like, stop. So and that's hard sometimes, but you know, it's part of the part of the territory. It's like I chose to do this and I could choose not do it, and that's fine. It's what being a leader in the community is, but it also doesn't mean you have to sacrifice your your your your livelihood for the sake of of your professional work too.

  Benn Marine 46:09

  So boundaries are tough. Well, and so you started in 2014, which m puts us in your fifth year, yes.

  Chris O'Connor 46:16

  This is um, yeah, I'm just finishing. So I started in August. So I think next week is my fifth anniversary. So yeah.

  Benn Marine 46:26

  Still going strong. Well, congrats and happy fifth. I'm curious what maybe your favorite memory is or or kind of uh some of your favorite moments.

  Chris O'Connor 46:38

  Um I'll share this. Talk about the anxiety of the ask. I will never forget it was our first Spirit of Pride cruise. And we had a boat full of people on a boat with bars on a three-hour, you're out in the middle of Casco Bay. And we the plan all along was about halfway through. And as I said a little bit earlier, you know, when you have a captive audience, part of our responsibility is to make sure that you present them with the opportunity to support the organization. And that's the the professional way of saying ask them for money. And so we had the the the boat. I asked the captain, I'm like, all right, let's park her parker here, we'll kill the engine. I'm on the microphone. I think Gia talked about, you know, an update about our work, and then it was my job to make the ask. And I'm like, all right, we've got this, like everyone, this is a great group of people. I did my homework of looking at kind of what people's um levels of giving were in the past, and I was I was sure as anything that I could start with a thousand dollar ask. And so I have 150 people all like right there, ready to go, and I make the $1,000 ask. And in my mind, it's compelling, it's passionate, it's authentic, it's it's connected to our work. All of the and and again, like this is within my first probably nine months. So um I'm I'm like trying to do it textbook, like this is what they say I was supposed to do, and I did it. And there was an audible gasp from the entire boat. There was just the like, like, did he really did this did this guy really just ask for a thousand dollars right now? And I was just like, oh shit. What do I do now? And so on my feet, I just because I had a little bit of of of of traction under me, I had done a and and I was just like, and I don't I don't drink during events because I for me it's important to to always be like on my game. Up you know, maybe a drink or two would have helped me relax, but I was just like, no, and I I literally just I'm like, all right, I clearly I made fun of myself. I'm like, I clearly missed the mark on that. Um bear with me. And I was like, let's try this a different way. A thousand was, you know, are there two people who can make a $500 gift? And one, two, all like automatically, two people. And so we met that $1,000, you know, I salvaged that, and we went through the rest of the levels as we do. Um, and it was great. There was good energy. And just as I was about to finish, I had one person raise their hand and say, I'll do a thousand dollars. And so we raised an amazing amount of money that, you know, and every year the cruise has been a wonderful, wonderful success. But it was a little bit of a lesson of, you know what, it's you don't have to take this so seriously, and that these are people that again, you know, they're your members, they're you, you know, and it's and it's our responsibility to know them and to let them know you. And so it wasn't this. If you look back to the first, my first ask where I literally flipped out and was like, I can't do this, and and ran away and in on the verge of tears. Like, to that point, even like, and and again, that's not a a huge period of time, but it was that lesson of we're all human in this, like, it's not no one expects me to be this robotic. You will raise money, blah blah blah. I think our board expect me sometimes, maybe, but um I don't think I don't know if they're gonna listen to this. But I mean, there it's um yeah, you have to give yourself a little bit of that, you know. So that was kind of one of the funny ones. Um, I remember it was my first gala. I mean, that's probably my like my most overwhelming memory was our our first gala um from a fundraising development standpoint. Like we had uh we had an event planned. I thought what you know what a gala would entail. Um, and then I had gone to creating change um for the first time ever. This was back in 2015, and it was a month and a half before the gala was supposed to happen. And I went to this one session on event fundraising, and I literally came back and I was like, scrap the gala. Everything we had, we had to change the whole plan. We had to um, and because I just I took the time to listen to someone else that that had more expertise. I had the expertise in event planning, I didn't have the expertise in event fundraising. And so I I took notes and we did a consultation with the person from this organization, um, and we crushed that gila. Like it was, and I remember, and it was so funny. One of the things, another funny story. Um, one of the things let tools that they gave you was to, you know, could you we always had a VIP reception, so could you use your VIP donors to set up a match to go into your into your big room and use that during the fundraising portion of the night. And so we did that. And I had a $2,500 match. Um, and so we made the mistake of putting the match at the wrong level. And so what we did is we said we needed a hundred twenty-five dollar donations. And I was like, we could do that. And our fundraiser at the time, the person who was doing the fundraising asked, did that, had it all went, and then it stalled at like 57. And I was like, what the heck? And again, everything you're taught and learn is you can't you can't have a match and not and not have it matched. Like you've gotta it for the success and the energy and the feel-good of the room, you've gotta. So I was like, give me that microphone. I jumped on stage and I start running around the room. I'm like, come on, we gotta do this. And which you know me, like I you I think you were actually probably there. Um, but like that's really authentic for me. Like, I'm that kind of person. Like, I'm not, I I'm I'm jump in, I'm hands-on, uh, you know, people, I'm I can be loud and I can be funny and I can be obnoxious. And so I literally was like, we gotta get to 100. And and it was tough. And at one point, I I remember I said that a $25 gift was the equivalent. You know, sometimes we do like a $5 gift as a cup of coffee at Starbucks. Like, couldn't you give a cup of coffee a month? Blah, blah, blah. I said that a $25 gift was an aggressive order at the McDonald's drive-thru. And I remember in the moment, like, now you're standing on stage, you're running around a room, you really have no concept of what, like, it's it's you're in a different place. Spotlights are on you. There, you know, it's you you really lose like what's going on. So, long story short, you know, there was some laughter, and I'm like, and we had one person that was like, quick, somebody do math. Like, can I get one donor? Like, what's we were 13 short? What's 13 times 25? And so we met the 2500, and there was like big applause, and we all laughed. And um the next morning I woke up and I was in a daze. Like, I was like, what the hell happened last night? Like, it's just that's that post-event. Like, and uh I called my boss and I was like, Did I really say I had this memory of I was like, Did I really say that a $25 gift was an aggressive order of the McDonald's drive-thru? She's like, Yep, you totally did. And uh, we just laughed, and to this day, it's still this funny thing. We've now had four galas since, and every year it comes up and like we joke about we're gonna put that in. And so it's just I guess too, it's a lesson in like sometimes you gotta do what you gotta do. Um, but again, there's just no, you know, there's n I could have beat myself up about it. I could have, you know, it's um you you gotta allow yourself a little bit of room to to breathe and to enjoy the work and to not go get so stressed about it. Um and and that's I I can get stressed about things. And you gotta remember why we're doing this work. And it's, you know, when I spend a an afternoon with the 55 kids that I've spent all year fundraising to be able to pay for camp for them to be able to go to and writing grants and and training our our summer canvas young people to go out door to door to do fundraising to support this camp. It's like when you actually take a step back and and it's very easy to get caught up in the day-to-day and the meetings and the this and the that. But when it's I guess that's another strategy I would share with folks is like don't get so caught up in the in the logistics of the work that you miss the reality of the work. You know, and so whether it's spending a day and and I've always gone to all of our hearings like on conversion therapy, like I'm in the room because I wanna I want to experience that. I wanna he I want to see legislators, I want to see our young people testifying. I want to see, you know, the impact of this on our community. I want to see our community members testifying. I wanna because otherwise who the hell gives a crap about the gala or the pumpkin ball? Like it's not that's uh our work is about these young people, it's about the members of our community that are struggling day to day. And so for me, it's I've got to do that too. So that's and I guess that's how I stay stay connected to it all.

  Benn Marine 57:21

  That's awesome. Any other final last thoughts or things you want to leave folks with?

  Chris O'Connor 57:24

  Oh, I don't know. This has been really interesting to talk. I've never it's kind of really um interesting to do this at that five-year point. Um, you know, one of the things you don't a lot of development folks don't do this work for long, because it can, there's, you know, it's there's a a a real I think organizing work in general, there's there's burnout is real. Um, and so, you know, I guess that's the thing is to encourage people to make sure you're taking care of yourselves um too in this work. Because when you're a small organization and you're taking on the world, um, you know, and we're everywhere we're all taking on the world, and and especially in these most most trying times that that many of us have faced um in a long time, it's um it's really easy to to get lost in social media, to get lost in email, to get lost in the the my boss wants me to do this and my board wants me to do this, and you know, so people people have gotta take care of themselves and and take care of each other. Um, because we've, you know, I talk about it all the time as, you know, I I'm not doing this work as hard as I am right now for it to wrap up, you know, when I'm done. You know, I it's I I'm doing this work for the sustainability of I want this to, you know, it's gotta continue beyond, well beyond any of us that are living today. Like it's we need these organizations to be around. And so to do that, like we've got to also take care of ourselves too, because otherwise, you know, it's um I don't know. We don't we don't we don't get it done.

  Benn Marine 59:11

  So yeah, I guess that's it. Cool. Well, thank you so much, Chris. I I appreciate your time.

  Chris O'Connor 59:17

  Absolutely.

  Benn Marine 59:24

  All right, team, thank you so much for tuning in to this week's episode. As always, I will have all the resources that Chris mentioned in this episode in the show notes, which you can find at oceanoorganizing.com. Thank you all so much. Keep up the good work. I appreciate you. Be well.