Christian, Donald and Rudy sit down to discuss Che Guevara's program for a socialist transition using Helen Yaffe's book Che Guevara: The Economics of Revolution as a background. We visit the economic "Great Debate" of Cuba in the early 1960s, the different approaches to using the law of value for socialist transformation, Che's critique of market socialism, his model of Cuba as a single socialist factory, and how this model compares to contemporary approaches such as the People's Republic of Walmart. We emphasize how Che's humanistic outlook in molding new humans prefigured some of the problems that other socialist societies such as Yugoslavia or the Brezhnev USSR would face, and how his contributions add to the debate around cybernetical socialism today.