This chapter looks at two entrepreneurs who were particularly successful: Henry J. Kaiser in New Deal America and during World War II, and Friedrich Flick in National Socialist Germany. It reconstructs the public image constructed by the two men and their respective organizations. Although the two political systems were fundamentally different, Kaiser and Flick took both advantage of the opportunities for expansion that arose from the political struggle against the Great Depression and the preparation for war. Their “semantics of success” played down the extent of their economic power and distracted from profit opportunities offered by government politics. Instead, they highlighted anachronistic forms of a personal entrepreneurship that missed the practice in an age of bureaucratic capitalism.