Background & History
How We Got Here
SWAG INC grew out of Founder and CEO Joseph Caldwell's personal journey.
Our Story
Inspired by hardship, for those currently facing it
From his family's high-profile community business on the south side of Chicago, to a Bachelor's degree in finance from Florida State University, to earning the Silver-Salesman Award for Sales Excellence as a Honda salesman, Joseph has been surrounded by, pursued, and embodied excellence his entire life.
In 2022, life dealt him his hardest hand yet — he was incarcerated and sentenced to two years in prison. Instead of being broken by this experience, Joseph emerged untouched in spirit and more purposeful than ever. He gave back: Joseph taught entrepreneurship, life skills, assessment test preparation, and banking to those alongside him.
During that time, the SWAG concept was born: a commitment to serving others, and in particular, those who have been impacted by the criminal justice system.
Today, Joseph stands at the intersection of lived experience and intentional purpose, blessed with the opportunity to share a story that is equal parts struggle and grace. He is committed to proving that redemption is real, that excellence endures, and that service is the highest form of success.

Joseph Caldwell
Founder & CEO
