Paul W. Ruppert

Founder, STKHLDR Consulting

Small Business Advocate | Main Street Strategist

Paul W. Ruppert is a seasoned entrepreneur and community economic development leader with over 30 years of experience launching and operating small businesses across food, retail, and real estate. As founder of STKHLDR Consulting, he provides technical assistance, coaching, and strategic support to help small businesses grow and thrive - particularly in Main Street and neighborhood commercial corridors.

Paul recently served as Executive Director of the Upper Georgia Avenue Main Street in Washington, DC, where he led small business engagement, implemented façade improvement grants, and coordinated district-wide promotions to strengthen local commerce. He brings deep experience from both the public and private sectors, including revitalizing public markets in Baltimore and launching beloved D.C. businesses like Room 11, The Passenger, and Upshur Street Books.

Paul’s work centers on empowering entrepreneurs, building local ecosystems, and turning neighborhood assets into engines of inclusive growth.