Jesse was born in the Bronx but was raised in New Rochelle, Westchester where he attended high school. After graduating in 1996, he earned a merit scholarship to Wesleyan University. He majored in American Government at Wesleyan, while his studies primarily focused on classical philosophy and political theory. He graduated in May 2000 with a 3.35 GPA. He hopes to attend Columbia Law in the fall of 2001.

His community activism includes Union Summer (97) and the East Harlem Tutorial Program (summer 98). His work experience includes summers with the Interfaither Center and Ruder Finn Public Relations. At Wesleyan, he has worked as a DJ for three years. His DJ talent has been focused on his internship for Rawkus Productions over the past year. His other interests lie in chess, baseball, and fashion. His true aspiration is to become a model, but this light is dwindling rapidly due to the decreasing unpopularity in the boy band look. Instead, he has decided to redirect his talents in environmental law.