Art with a Heart has come a long way since founder and executive director Randi Pupkin launched the nonprofit from her law office desk in 2000.Pupkin had been working in construction litigation for 14 years when she decided she needed a change — a new way of helping people. So, she left her legal practice and founded Art with a Heart in order to provide art classes to communities around Baltimore.What started as a small but passionate project out of the trunk of Pupkin’s car grew into a citywide operation. Art with a Heart hosts thousands of art classes per year, has installed about 300 public art pieces, and is a regular fixture in Baltimore City Public Schools and other community sites.Last month, Art with a Heart announced it will be expanding with a satellite location on The Avenue in Hampden, which will house HeARTwares, the nonprofit’s social enterprise store, as well as HeARTworks, their workforce development program.Next year, Pupkin will retire from the nonprofit she founded and will officially pass the reigns to her current deputy director, Megan Gatto, in June 2025.Pupkin spoke with Baltimore Fishbowl about Art with a Heart nearing its 25th anniversary, preparing a new generation to take over the nonprofit, and the difference art can make (and has made) in the lives of Baltimore residents.Baltimore Fishbowl: What was your inspiration for starting Art with a Heart nearly 25 years ago?Randi Pupkin: My inspiration was my love of art and my love of people. I took art classes as a young child in Baltimore. I’m born and raised in Baltimore, and art was always like my recess or my sport. I never was an athlete, so going to art class was where I could be anywhere in my head – the beach, some foreign country – and kind of escape from life and I valued that. I became a lawyer because I love the idea of helping people and elevating humanity, and I thought I would be able to do that as a lawyer. I found that I was really fighting with other lawyers more than I was elevating humanity, so I decided to combine my love of art and my desire to help people and I founded Art with a Heart from the desk in my law office.BFB: How did Art with a Heart’s work specifically with Baltimore City schools come about? Tell me how that works.RP: We just got a request from a principal years ago because there was a void in his school for art programming and he asked if we could fill that void with our programming, which we were already doing in the community. We were already taking art classes to communities that did not have equitable access to art, whether that was in rec centers or PAL programs or shelters, group homes. Children, youth, seniors, anyone who didn’t have access. We were already providing that enrichment, and this principal heard about us and asked if we could fill the void in his school. That’s what we did and that grew from one school to eight schools to 15 schools, and now we’re in 17 schools with the desire that we would not have to be in any schools, but we’ll be in the schools until we don’t have to be in the schools.BFB: You’re kind of hoping to work yourself out of a job with those schools, right? That one day your partnership will no longer be needed because they’ll have their own robust art programs.RP: Yes. I mean, the idea is that there’s not a teacher shortage, but I think I read the other day that there’s 171 vacancies in Baltimore City. I don’t know how many of them are arts teachers, but for sure we work here if we’re needed.BFB: How have you seen youth grow through Art with a Heart’s workforce development (HeARTworks) and leadership (Art of Leadership) programs?RP: So the workforce development program started 20 years ago. It’s wonderful to see a young person walk into the program skeptical and then kind of figure out that we’re trustworthy and consistent, and that they’re here and they’re in this program and it’s almost like they resign themselves to showing up. Then you watch their minds open and they find joy in the process. Many have gone on to better themselves in school and in jobs. We have two employees right now that were in the program that work in Art with the Heart. And many other young people – well, they’re probably not so young anymore. It depends on how you consider ‘young.’ It’s relative – but many other that I’m still connected to through social media, they’re living their lives, they’re working, they’re married, they have kids. Some aren’t married, but most are working, and many would credit the path that they decided upon starting here at Art with a Heart.The Art of Leadership is in its 10th year. We’re in our 10th cohort. That has been extraordinary in that the community that is created in that program — it’s a small cohort. It’s between like 18 and 25 students. — they stay connected. For 10 years, the first cohort has been connected. Two of the students in that cohort are now on our advisory board. One is a teacher, and one works for Governor Moore. And Moore [before becoming governor] was the speaker for our first cohort. He came and spoke to them, and all the students got his book, “The Other Wes Moore.” That was the only book he had written at the time. And so one works for him now. I just think that that program provides those students with the opportunity to stretch their boundaries, to meet community that they otherwise would not even know about, to talk about issues that they don’t usually have the opportunity to engage in conversation that they have here. It’s a really special program, and I’m very proud of the students that have allowed themselves to open up and be vulnerable with people they wouldn’t know but for that program.BFB: Your work with the community is very hands-on. How did you manage to continue that work during COVID?RP: That’s a great question. Everyone that works here has a lot of grit, and it was a really scary time. I think we all felt like we got punched in the stomach a little bit, like now what? But it really didn’t take us long. It took us a lot of Zoom calls, and as a team gathering on Zoom, and figuring out what’s next, how do we keep our students engaged in the creative, tactile art-making, not just talking on Zoom. I think we were all out in March [2020]. Probably by the end of April [2020], we were packing art kits and delivering them to schools, and the schools were handing them out when they were handing out laptops for students to be able to engage in school virtually. So we packed 12,000 art kits and delivered them to all of the schools that we programmed with. As an aside, we also have a large community art effort, and we engage thousands of volunteers every year, but we have a core group of volunteers that are between the ages of probably 60 and 90, and they come every week. It’s about 50 of them, and they have shifts, and they bring their lunch and it’s like a job to these 50 people. Prior to the pandemic, I used to think ‘Wow, they just do so much for us. They help us prepare for classes, they help with community art projects, and they just keep us rolling.’ And during the pandemic I realized – as they were the first people knocking on our door to get back in and they were the highest risk group – how much we also do for them, not just how much they do for us. And so we built a sculpture, a community art sculpture that’s now at the University of Maryland hospital, entirely during the pandemic. Coming in masked, working six feet apart, whatever we had to do, we created that big eight-foot sculpture during that time.BFB: Tell me how Art with a Heart has been so successful and stuck around for so long. I know many nonprofits aren’t around after even five or 10 years. So 25 years is a lot!RP: Well, thank you. I think it’s extraordinary. I think the first thing is that somebody told me right after I incorporated Art with a Heart and really went full throttle – because it was just me – somebody in the funding world said most nonprofits last five years. It was kind of like that’s all I needed to hear to make sure that we lasted more than five years. I was like, ‘Okay, here we go.’ I think the organization has lasted because of the commitment of the people who have worked here, who currently work here, who care deeply about the mission. Both our employees, our teachers and assistants in the community, they’re foot soldiers. They do hard work every day. Nothing happens in a silo here. The recognition is really about the community of people that commit to making it work every day. It’s a machine and we all help the machine run. It’s extraordinary. It really is. And I’m so grateful for the staff and the teachers and assistants and the team and the volunteers; it’s a full community effort. I know that it’s cliche to say it takes a village, but this organization, the village, is what makes it happen. I couldn’t do it on my own, that’s for sure. And nobody here could. But I think we dig in deep when we have to, and we know how to be nimble and we work hard.BFB: Are there a couple Art with a Heart community art projects that you’re particularly proud of over the years?RP: Of course. There’s the first large-scale mosaic that we ever did. Debbie Phelps [mother of Olympic swimming champion Michael Phelps] was the principal at Windsor Mill Middle School, and a student had been hit by a car while riding his bicycle and he passed away. They were planting a memorial garden for him and she contacted us to do this large mosaic on the wall of the garden. When I said we dig in, we dug in. We were like ‘Let’s do this.’ And it just started a snowball effect of large-scale projects. It was probably 2009 or 2010. And that just started this snowball of other murals, other mosaics, and it’s just continued. We have close to 300 community art pieces of various sizes all throughout the Baltimore community. And that thought brings me incredible joy just to be able to beautify the community. It’s like we’re part of the fabric of Baltimore with paint and tile. So that one project really is special. We had an artist working with us named Jane Rubini who designed it, and then we took the panels to the school. The students that knew the deceased young man worked on it. His family worked on it. Everybody in the school worked on it. Then we installed it. It was a really special project. That led to another project that was like 18 feet by 10 feet. Huge. So that one was really special. And of course, the heart that was created during the pandemic. It’s hard to find a favorite.BFB: Is the heart that sculpture at the University of Maryland hospital you were speaking about?RP: Yes.BFB: Has your leadership style changed over the years?RP: For sure. I mean, I’ve been marinating for 62 years. I think as a leader and as just a person, you grow and change. I try to keep learning and listening. When I was in law school, I used to take walks with this woman who was 88 years old, and she used to talk to me about listening and how it kept her young, and I’ll never forget that. And so I really try and listen, and I know what I don’t know, and I know that there are people who know what I don’t know, so I really try and grow and learn from that. I think as you get older too, this is going to sound cliche, but you learn to – you don’t sweat the small stuff, but you learn to prioritize things. I also think there’s a divide between what it was like when I was growing up and how we worked, and younger people today and their expectation of a work environment. I try and pass that on to the younger leaders in the organization who kind of speak the same language, because I’m always full throttle. I’m always just charging and working and I love what I do, so it doesn’t feel bad to be doing it.BFB: I understand that you are set to take a step back from your executive director position soon. What will that look like? I know it’s hard to completely walk away from an organization that you’ve been running for 25 years. Will you still be involved?Megan Gatto, deputy director of Art with a Heart. Gatto will take over as executive director when the nonprofit’s current executive director, Randi Pupkin, retires in June 2025. (Courtesy photo)RP: So this is interesting. I am the founder, so everyone asks that question and I think it’s a great one. I think it would be daunting if I didn’t feel like the succession plan was good, and the person who was succeeding me, if I was worried about that person not being able to succeed. But I am really excited and really confident in handing this child over to the next person. I think she’s going to do a fantastic job. And I will be behind the scenes coaching her a little bit. Not formally as a coach, but consulting with her and helping her. I will not be sitting on the board. I am not going to have an office. But I look forward to helping her in any way I can and advising her. There’ll be lots of questions, I’m sure. I mean, there’s a lot to think about when you’re running a multi-million dollar nonprofit. There’s insurance and phone systems and HR matters, and she’s learning. It’s a co-leadership model right now. We share an office, so she’s basically shadowing everything. And although she’s not here today for the interview, she’s heard all this before. It’s actually really exciting. I know it’s time to go. The organization deserves a younger leader now.BFB: Who will be taking over?RP: Our deputy director, Megan Gatto.BFB: So after that ‘coaching process,’ when she’s more used to being in the executive director role and you can take even more of a step back, what’s next for you?RP: I’m going to take a little time to read a book, and then I want to get a job. I want to work somewhere else. I’m not tired. I mean, I’m a little tired, but I see that I have energy to do something else. I just don’t know what that is yet. I’m excited about what’s next. What it is, I’m not sure.BFB: You mentioned you want to read a book. Do you have any particular books you’re looking forward to?RP: My advisor from college worked for the State Department, and his wife worked for the State Department, and he published a book of her diary. It’s like 900 pages. They were like surrogate parents to me, so I want to read that book. It’s going to take a while.BFB: Yeah, 900 pages! Wow!RP: I know. Maybe I should start with Dr. Seuss to work my way up.BFB: Art with a Heart will have its 25th anniversary next year. How will you and your team celebrate the occasion?RP: We are having an event on March 29, 2025 at the M&T Bank Exchange. It’s in the evening. And so we’re going to have a party. I mean, we’ve got to have a party. We haven’t really had a party since 2015, any kind of fundraiser event. I’m calling it a party because really this is a celebration. It’s a celebration of the extraordinary work that the organization has done for 25 years. But also, passing the paintbrush, so to speak. We’re really looking forward to just bringing together, the Baltimore community in one space, to celebrate the organization and the people who have made it happen. We signed a lease to take a satellite location for the organization at where the Hampden Family Center UCLA Avenue is. We have a social enterprise retail store called HeARTwares, and we’ll be moving the store onto the Avenue, which is very exciting because it’s never really been in a location that allowed it to have foot traffic. We’re in Mill One and people do come here, but it will be very nice for just passersby to see the work that’s created by our students in our workforce program. We’re also going to move the workforce program to the Avenue, to that location. It has two classrooms. For students, transportation’s never been a barrier to them getting here; they just have to walk from the stop on the Avenue. So now it’ll just be less of a walk for them. And we’re excited about that too. That’s an exciting thing that’s happening, kind of to celebrate and honor and feel our growth in 2025.We want to be really clear, because the whole universe is going to think we’re moving, but we’re not moving. When we moved into our space in Mill One, we had eight employees. Now we have 17. So it’s just a lot and that’s why we need supplement. We really ran out of space, which is unbelievable.BFB: It’s a good problem to have!RP: I know! I always tell my team that being busy is a great problem to have, because we could be laying people off. I hope that never happens.BFB: What would you like to see for Art with a Heart in the next 25 years?RP: Well, I feel like that’s not for me to answer because there’ll be a new leader who will have a vision of her own. I would just like to see it thrive. We have like five branches to the organization, and I would like to see them all continue to grow and, like I said, thrive and be part and parcel to our community.