This chapter traces the philosophical evolution of libertarian thought from its classical roots in Socratic dissent and Roman natural law through the Enlightenment and into the twenty-first century, culminating in what is here termed Vivalibertarianism. By analyzing thinkers such as Locke, Smith, Bastiat, Mill, Hayek, Rothbard, and Friedman, the chapter explores how core principles—individual liberty, limited government, spontaneous order, and market coordination—have been adapted to successive political and economic contexts. The study then turns to the digital age, where libertarianism finds new expression through meme culture, decentralized technologies, and techno-elite narratives promoted, inter alia, by Elon Musk, Javier Milei, and Peter Thiel. Vivalibertarianism emerges as a post-institutional libertarianism shaped by online subcultures, the aesthetics of individualism, and distrust of state and collective structures. However, it also reveals key contradictions: rhetorical decentralization alongside centralized platform power and a populist posture paired with elite techno-authoritarianism. By framing Vivalibertarianism as both a continuation and a mutation of classical liberalism, the chapter provides a critical lens for understanding libertarianism’s ongoing evolution in the age of algorithmic governance and digital capital.