Madame CJ Walker! She was the first self-made woman millionaire in the United States, and made her money by selling Black hair care products. She was born in Louisiana just two years after slavery was abolished, and ended up orphaned at age 7. Her life was HARD, but what she ended up achieving, virtually on her own, is amazing. She also used her money to donate to a lot of social causes, like a scholarship fund for Tuskeegee University and war relief during WWI. Netflix made a mini-series about her called Self Made that debuted earlier this year, and I would strongly recommend it! It has some inaccuracies (they make her relationship with her biggest hair care rival seem very acrimonious, for one thing, when it probably wasn't quite so bitter and her rival probably wasn't so villainous. And for another thing, based on all available evidence her daughter wasn't really lesbian), but it's really good!
Another good underrated figure is Henry "Box" Brown. Henry was born into slavery in Virginia around 1815. He ended up marrying a woman named Nancy, and although a lot of enslaved people weren't allowed to live together at the time, Henry and Nancy actually did live together and had several children. Henry worked at a tobacco factory, and Nancy worked on a nearby plantation, where her slaveholder extorted Henry into paying him to keep him from selling Nancy and their children. Finally Henry didn't have the money, so the slaveholder sold Nancy, who was pregnant, and their three children, to a plantation in North Carolina. Henry was devastated, and decided that because he had nothing to lose now, he might as well try to escape slavery. He convinced a free Black friend named James Smith, as well as a sympathetic white man named Samuel Smith, to help him. Henry came up with the idea of mailing himself to freedom, and Samuel Smith contacted the Philadelphia Anti-Slavery Society to let them know that Henry would be arriving in the mail at their office. Henry poured sulfuric acid on his hand to get out of work, and then crammed himself into a 3'x2'x2'6" box, which Smith addressed to Philadelphia and wrote, "This Side Up" on (although apparently most workers ignored the "This Side Up" message). The box had one hole for air, and Henry brought a little bit of water, a few biscuits, and a little tool for making more air holes for what ended up being a 27 hour journey. In his own words, he described being upside down in the box thusly: "I felt my eyes swelling as though they would burst from their sockets, and the veins on my temples were dreadfully distended with pressure of blood upon my head. I felt a cold sweat coming over me that seemed to be warning that death was about to terminate my earthly miseries." Luckily eventually someone turned the box (and Henry) on its side, and he made it safely to the offices of the Anti-Slavery Society in Philadelphia on March 30, 1849. His story became very famous and widely publicized, and he made a travelling road show to tell it.?He looked for Nancy and their children after reaching freedom, but never found them, and in 1850 the Fugitive Slave Act was passed that made it legal to capture Henry and sell him back to slavery. To avoid that, Henry moved to England until 1875, where he remarried. He ended up moving back to the US, and then Canada, and died in Toronto in 1897. As an epilogue, Samuel Smith tried to mail more enslaved people to freedom a few months after Henry successfully did it, but he was discovered and sentenced to 6.5 years in jail. Henry remained free for the rest of his life.