Simkin obtained his BFA from Temple University’s Tyler School of Art and his MFA from Cornell University. He enacted site-specific commissioned installations across the country at venues in San Francisco, Saint Louis, Albany, Philadelphia, Boston, and Maryland. He became notorious for a performance he organized at a benefit event for the Print Center in 1975. He put works of art on a conveyor belt that fed a paper shredder. If no one agreed to purchase the art before it reached the shredder, the work was destroyed.