This case study presents the true story of Rodolfo--a former tailor and attorney from the provinces of Cuba--who moved to Havana to start a hospitality business. In 2016, the author (referred to as Adam throughout the case study), a business law professor from the United States, visited Havana to interview Rodolfo and learn about the factors for success in starting up a business in the rapidly transforming economy of Cuba. At that time, Rodolfo presented a highly attractive investment opportunity. The investment opportunity raised several business, legal, and ethical questions with generalizable lessons, including whether and how to invest in markets restricted by rapidly evolving sanctions regimes. What originally was planned to be a teachable case study of entrepreneurship expanded to include an additional part focused on the legal and ethical aspects of investing in Cuba. Part II presents the case--ready to use in a classroom setting--for debating business, legal, and ethical aspects of the story. Part III presents a Teaching Note that includes background information useful in guiding class discussions of how Adam might proceed in responding to the opportunity presented to him in Cuba. Part IV concludes with a recapitulation of key takeaways and suggestions on contexts for using the case.