This paper draws on my recently published book, One Day I’ll Work for Myself: The Dream and Delusion that Conquered America, to explore the growing prominence of entrepreneurial ideology in American public life during the 1980s. In a decade defined by a roller coaster macro-economy—from the stagflationary crisis that began it to the long, volatile, and unequal bull market that followed—entrepreneurship and its attendant ideology took center stage. The national political conversation increasingly focused on young, dynamic, fast-growing firms that could supplant the “sclerotic” corporate dinosaurs of the post-war. “Bureaucratic” became a biting epithet, not only in corporate circles and in business school seminars, but also among the political activists at the helm of the so-called Reagan Revolution. This paper explores the intellectual and cultural appeal of this new fixation on entrepreneurship in a time of economic funk, from academia to policy circles. In particular, I trace the origins of a new business organization—the American Business Conference—which emerged as a self-styled political champion of high-growth, high-tech “entrepreneurial” companies, for whom it lobbied for lax regulations and lower taxes. It also shows that, despite the inherent appeal of that vision among Reagan conservatives, actually pursuing an “entrepreneurial agenda” proved more vexing than its boosters anticipated.