Randi Pupkin

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Art with a Heart, Inc.

Randi Pupkin, founder of Art with a Heart, Inc., transformed her legal career into a 25-year journey of community arts leadership that has impacted thousands of Marylanders. After practicing construction litigation for 14 years, Pupkin founded Art with a Heart in March 2000 from her law office desk, growing the organization from a few classes taught from the trunk of her car to as many as 16,000 interactive visual art classes annually, serving children, youth and adults in Baltimore’s under-resourced communities.

Under Pupkin’s leadership, Art with a Heart expanded beyond core classes to include a workforce development program, teen leadership program, service initiatives, large-scale community art projects and a social enterprise retail store called HeARTwares in Baltimore. The organization has installed over 300 community art and beautification projects throughout Maryland and expanded its impact internationally.

Pupkin explained that one of the most important lessons she has learned as a leader in Maryland is the power of collaboration and community, noting that “true progress happens when diverse voices come together with a shared vision and mutual respect” and that “effective leadership requires adaptability—being open to new ideas and approaches while staying grounded in core values.”

When addressing significant challenges, Pupkin said building a community art business from the ground up in a space that often lacks the sustainable funding required, “resilience, creativity and unwavering belief in the value of art as a vital component of the human experience.” She overcame these challenges by forging strong partnerships, prioritizing community engagement and continuously adapting to changing needs.

Pupkin explained that she uses her influence to make a positive impact by advancing innovative art programming rooted in “a strategic blend of art, human services, and education” driven by a commitment to equitable access to arts education. She noted that Art with a Heart “harnesses the transformative power of visual art to fuel civic and economic progress through workforce development, community engagement, service learning and leadership initiatives.”

Honoree profiles were written using an artificial intelligence program and supported by information provided by the honorees and other resources. Each profile was reviewed, fact-checked and edited for accuracy by The Daily Record’s editorial staff.