Social scientists have studied the transition from the post–World War II reliance on industrial and manufacturing sectors to a “postindustrial” or service-based economy. The changes that came to be called the “new economy” in the 1990s are a continuation of that transition. The economic shifts are real and provide the context for understanding the shift in the culture of corporate loyalty. This shift had a political dimension as politicians shaped new rhetoric to explain what was happening. In this chapter, I argue that the dot-com boom of the late 1990s through the year 2000 marked a political, economic, and cultural transition that had already begun by the time the commercialized Internet appeared. These political, economic, and cultural shifts emphasized individual responsibility over collective, corporate, and government security and embraced individual economic opportunity. With these changes, entrepreneurialism became celebrated as a means of fixing an economy that was creaking under the weight of aging manufacturing base, losing ground internationally, and struggling to recalibrate a delicate postwar balance of welfare state and corporate benevolence. Rather than being determined solely by the technological change of the Internet, major economic, political, and cultural changes in the United States paved the way for the dot-com era and for the prevalence of entrepreneurial attitudes necessary for it.