James Simon grew up in the Stanton Heights neighborhood of Pittsburgh, Pennsylvania. He won several national awards for his ceramic talents while attending Peabody High School, where he graduated from in 1972. He felt pulled to see the world and immediately hit the road -mostly hitchhiking and freight train jumping around the US and Canada. He learned carpentry and stained glass skills along the way. James hitchhiked east to west many times particularly exploring California, Oregon and the islands off the coast of British Columbia. He then went to Europe and the Middle East visiting Italy, Greece, Turkey, Iran, Pakistan, Afghanistan, and India. He lived in Australia and met the aborigines in Darwin.[ The aborigine’s ways and art had a profound influence on his life and work.

In the 1980s, while traveling in England he met acclaimed Hungarian child prodigy violinist and teacher Kató Havas- and followed her to Oxford to study violin. Kato introduced him to Master Luthier Andrew Dipper.[ James learned how to make violins and varnishes from Dipper and finesse his skills in sculpture and carving. James met Alvaro Escalante through Dipper and he was invited to move to Tepostlan, Mexico. James was influenced by the Mexican muralists such as Diego Rivera and artist Francisco Toledo and was inspired by Aztec, Mayan, and pre-Columbian sculpture.

In the 1990s, James Simon moved to São Paulo, Brazil where he opened a sculpture studio in Villa Madalena, a cultural district of São Paulo. James friended and collaborated with some of São Paulo and Brazils most distinguished artists including mixed media artist Jose Roberto Aguilar and composer and writer Jorge Mautner.

James moved back to Pittsburgh, PA in 2000 where he converted an old warehouse into his studio and living space. He hosted the nationally acclaimed Gist Street Reading series for 10 years starting in 2001. The readings were held monthly and featured local and national poets and writers. The series was directed by Sherrie Flick along with Nancy Krygowski and Rick Schweikert. The series focused on emerging writers publishing their first or second books. He continues to make sculpture and mosaics.