Digital Pirates: What would the world look like if a person saw everything, truly everything, as an opportunity? Consider the case of Ross Ulbricht, otherwise known as Dread Pirate Roberts. After earning the rank of Eagle Scout, a bachelor’s degree in physics, and a master’s degree in materials science and engineering, Mr. Ulbricht founded the darknet market, Silk Road, in 2011. By 2015, at the age of 31, Mr. Ulbricht was sentenced to life in prison without parole and fined 183 million U.S. dollars. In this course, we will explore the complex lives of modern-day pirates like Mr. Ulbricht who push hustle and innovation to unsustainable and unethical extremes. The class will outline the technologies and business processes underpinning digital piracy including cryptocurrencies, the dark web, encryption, artificial intelligence, and e-commerce. In the process, we will analyze digital pirates’ approaches to innovation and technology to explore and understand the entrepreneurial spirit.