Dreama Caldwell grew up in rural Alamance County, North Carolina. After graduating from Alamance Community College with a degree in Early Childhood Education and Teaching, she spent two decades working in childcare. Following a bitter encounter with the criminal justice system, Caldwell joined Down Home North Carolina as a volunteer member. At Down Home she initially worked with their Stop Criminalizing the Poor working group, which sought to educate the community about the injustices of cash bail. After running for Alamance County Commissioner in 2020, she was hired as a community organizer.  She became Co-director of Down Home a year later. After hearing of her story, singer-songwriter Joe Troop penned a song about her, which was made into a music video in 2021.