Gerald Jackson Jr., a South Side Chicago native, attended Bennett Elementary School, De La Salle Institute, and graduated from Urban Prep Charter Academy before earning a degree in Information Systems from Howard University’s School of Business.

With over a decade of experience in corporate and startup IT, Gerald has built a strong foundation in mobile app and website development, specializing in UX design and research. His career has been a testament to his philosophy of being “more than an athlete.” Balancing his STEM pursuits with a passion for basketball, Gerald has transitioned seamlessly between tech roles and professional sports. Most recently, he served as a UX researcher at Wells Fargo while playing for the Virginia Vipers in the TBL Pro League in 2023. His basketball journey has taken him to international courts in Spain, Germany, Lebanon, and Mexico, and he has participated in three NBA G League private workouts.

This dedication to athletics has led Gerald toward a new mission in health and wellness. Through his 501(c)(3) nonprofit, Defeat the Day Health & Wellness Inc., he combines his expertise in technology and sports to develop wellness programs that address the needs of the Chicago community. In partnership with Casual Elegance B2B and its Executive Leader, Yolanda Brown—Gerald’s mother and guiding inspiration—he is committed to uplifting the South Side of Chicago. Together, they strive to create lasting, positive change through accessible programming and dedicated community support.