Mom and son duo Sharee and Davone travel to Nashville, Tennessee, where they learn that their fourth great-grandfather Larkin Ford was a part of an 1840s landmark Tennessee case in which he was awarded the farm that he worked on as a slave.

Host Faruq Tauheed takes uncle and nephew Al and Jr. on an ancestral trip to Havana, Cuba, where Al learns that his grandfather Joseph Barlow owned and developed 34 blocks of downtown Havana, including the now-famous suburban neighborhood Buena Vista. But due to an unfortunate turn of fate, Joseph Barlow lost his riches in a political coup. As the two men connect over their own entrepreneurship, they learn where their family's resilience came from.