He helped find a key ancestor of one famous Black celebrity (I don't recall exactly who) who was emancipated by his Virginia owner in the 1820s in return for a small share in a blacksmith business whom he helped set up beside the National Road (roughly present day US 40).
The investment paid off handsomely for both former slave and owner. The one blacksmith shop grew into a chain of at least nine known shops and was highly profitable as traffic grew.
Instead of being proud of being a descendant of such a go-getter, the celeb was livid with anger, choosing to believe all of his ancestors were oppressed field hands rather than mainly descendants of a highly successful blacksmith who provided employment for scores of newly freed slaves over his lifetime.
I think he has at least one black person on each episode so that they can lament together about the horrors of American slavery, but he sometimes has white or Asian people. Most of them are celebrities that I had never heard of before.