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.