The Woodstock Festivals of both 1969 and 1999 have formed a distinct phenomenon in the popular imagination, but rarely are these two events examined through the lens of their civilizational implications. What happens when lots of people gather in a totally ungoverned, lawless shared space? How do they organize, interact, survive? And most importantly, what explains the difference between the original Woodstock, almost synonymous with peace and love, and Woodstock '99, in so many ways the apparent opposite? In the first episode of the series, Jake explores the fascinating story of the original Woodstock, from the eyes of those who experienced it firsthand, with the aim of understanding what made it such an important moment in history, how it even happened to begin with, and what it might mean for broader questions about human solidarity and the future of the world.

In the final episode of the series, Jake (with the help of historian Stephen B Oates' definitive biography To Purge This Land With Blood) details the dramatic conclusion of John Brown's extraordinary quest to destroy slavery and the profound impact it had, both immediately and on the course of history.

In part three of the series, John Brown and his renegade army move to implement his ultimate vision of igniting a widespread slave uprising.

In part two of the series, Jake discusses the crucial middle phase of John Brown's life, which sees him transition from a radical preacher to a violent, infamous revolutionary on the front lines of the growing battle over slavery in the United States. Brown also begins finalizing and acting on his plans for the grand finale, which, when detonated, will change the course of world history.

In part one of the series, Jake divulges the unusual upbringing and surprising early life trajectory that gave rise to John Brown, arguably one of the most underrated and important figures in US history. Understanding who Brown was involves understanding the complexity of questions such as when violence is or is not morally justifiable, if all forms of religious extremism are truly equal to each other, and what separates someone who tries to work within the system from someone who tries to overthrow it from the outside.

Jake discusses the foundations of what makes for a coherent anarchist perspective in the 21st century. He touches on real-world examples of anarchism in practice, ways of separating anarchism from the common ways it is misdefined, the moral untenability of hierarchical governments, social contract theory, speed limits, and what it means to call oneself an "anarchist" in 2025.