Benjamin was born and raised in the great state of Tennessee. From an early age, he developed a deep connection with Japan through a penpal friendship that sparked a lifelong interest in the language and culture. In 1994, he traveled to Japan for the first time as an 8th grader—a trip that profoundly shaped his worldview.

He later spent his sophomore year abroad at International Christian University (国際基督教大学) in Tokyo during the 1999–2000 academic year. While attending university, Benjamin worked at the International House on the UT campus and led campus tours for incoming exchange students from 2000 to 2002, continuing his commitment to fostering cross-cultural understanding.

The Benjamin Gregory Scholarship Fund was established in 2020 in memory of Gregory, Benjamin’s father, who passed away in 2019 after a courageous battle with Alzheimer’s. This scholarship honors both Gregory’s memory and Benjamin’s enduring belief in the power of international education, inclusion, and global perspective.