Art with a Heart Founder Prepares to Pass the Paintbrush

Randi Pupkin leads the charge through the cold and damp garage of Mill No. 1. Upstairs, in the sun-drenched studio and offices, student interns and most of Pupkin’s 20 employees are at work.

But some projects are too big—and messy. Which brings us to this subterranean parking structure, where inside a nondescript white tent tucked in a back corner, she joins a handful of volunteers who are dutifully attaching shards of mosaic tiles to a 12-foot-long horse and jockey.

The piece, designed with sculptor Howard Connelly, will eventually reside in front of a nursing home near the Pimlico racecourse and it’s just so Art with a Heart—collaborative, bright, and creative. It’s also one of the last projects Pupkin will oversee as the executive director of her nonprofit, which helps people enhance their lives through visual arts, before she steps down next month after 25 years.

“I really feel like it’s in the best interest of this organization that it has new, younger leadership,” says Pupkin, 62, pictured right, above. “I’m a different person now, the world is different, and I joke that I don’t speak the same language anymore. As the founder of this organization, it deserves the next.”

That next is Megan Gatto, 31, who started at Art with a Heart as a college intern and, after graduating from the University of Delaware with a BFA in studio art, came on as a full-time staff member in 2016.

“And I haven’t been bored a day since,” she says, pictured left, exchanging a laugh with Pupkin. It seems to be a mutual love fest, as the two sit on a chic midcentury-modern turquoise couch in their shared office. You could say they are on their transition media tour.

“I love her sense of humor, and I think she’s effing smart, and I think being funny and smart is like the perfect combination,” says Pupkin of Gatto. Gatto, who calls herself a reformed reluctant leader, says to Pupkin, “I love that no matter what our day holds, you always live in a ridiculously hopeful ZIP code.”

That hope has propelled Art with a Heart these last two decades. When Pupkin started the organization in 2000, she was working as a construction litigator and living what she called her “beige” era. And what better way to bring color into
her life than art?

“I love the way making art makes you feel,” she says. She knew she wanted to bring that feeling to others, especially those who were underserved.

When she started Art with a Heart out of a shed in her backyard with $6,000 in seed money, the idea was not just to showcase art, but to let people experience what it feels like to make it.

“The first four [project] sites were two group homes for emotionally troubled adolescent boys, House of Ruth, and an Alzheimer’s facility,” recalls Pupkin.

Now, during just the last year alone, Art with a Heart has expanded its reach in ways that Pupkin could once only dream of: It provided nearly 16,000 art classes to children, youth, adults, and families in schools, shelters, community centers, hospitals, and senior facilities around Baltimore, serving some 270,000 people. It completed and installed 16 community art projects with the help of more than 3,900 volunteers. And it opened a satellite location on The Avenue in Hampden for its HeARTwares social enterprise store and workforce development programming.

“I’m leaving my child,” says Pupkin, wistfully. “And she’s taking it over, and we will come out on the other side of the transition strong and healthy, and that’s the goal for both of us.”

You can feel the tinge of sadness in her voice, but also relief in knowing she’s picked the right successor.

“There’s a lot to be proud of in this process, it’s a marriage and they’re work, and this is work,” she says. “And I think you just have to remember—things that are worth having require hard work.”