Benjamin graduated from Allegany Limestone Central School in 2000. He then went on to double major in Biochemistry and Religion and Philosophy from Roberts Wesleyan College in Rochester, NY. He eventually returned to Roberts where he received his Masters of Science in Strategic Leadership. Shortly after he began his career in insurance as a career agent at New York Life in Rochester. In 2014 Ben moved back to his hometown and took over the Nationwide Agency in Portville, NY. He has since expanded that agency to span across New York State, and even into Florida, and runs all of them with the help of his wife, Christa.