In March 2020, James launched “Java With Jimmy,” an internet-based talk show created in response to his anticipated disproportionate impact of COVID-19 on Black and Brown communities. The four-day-a-week vlog cast has since evolved into one of Boston’s most recognized, community-focused, informative, resourceful, and politically engaging platforms, boasting over 20,000 followers across social media. Java With Jimmy covers the importance of health equity, medical information, mental health awareness, community struggles and achievements, political news, and expressions of gratitude. It regularly features prominent political leaders, including Boston Mayor Michelle Wu, Congresswoman Ayanna Pressley, and Governor Maura Healey. Java With Jimmy celebrated five years of impact in the spring of 2025.