Free Thinking Through the Fourth Turning with Sasha Stone

Episode: “Close Encounters of the Totalitarian Kind”

Date: April 8, 2026
Host: Sasha Stone

Overview

In this introspective and sharply critical episode, Sasha Stone explores how American society, particularly on the political left, gradually embraced forms of totalitarian thinking in the digital age. Drawing extensively on Jacob Siegel’s “The Information State” and weaving in her own personal journey from progressive activism to disillusionment, Stone investigates how the utopian dreams of the online Left mutated into a restrictive and controlling social order. Key touchpoints include the evolution of the information state, the impact of social media, the 2020 election, pandemic responses, and the societal rifts that emerged in recent years.

Key Discussion Points & Insights

1. The Rise of the Information State

• Siegel’s Analysis (00:25)
  • The information state is not “about penetration to great depths, but by the digital speed that brings all things to their surface in the shadowless glare of information on a grid of auto control.”
  • The aim is not to “conquer the soul, but to render it obsolete” through algorithmic stimulus that kills personal reflection and authenticity.

2. From Utopia to Dystopia: Sasha’s Personal Narrative

• Sasha’s Beginnings Online (01:13)

  • Early enthusiasm for virtual identity and progressive activism. Stone recounts transforming personal failures and heartbreak into digital reinvention.
  • “The Internet allowed me to remake myself as someone else. I could be strong, I could be confident, I could be beautiful, because who knew what you looked like? ... I dove into a life online full of excitement and wonder, a dreamscape of endless possibilities.”

• Creation of a Progressive Online Utopia

  • Stone details her pivotal role as an “army of clicktivists” during the Obama era, reveling in the excitement and optimism of making America more inclusive online.
  • “We felt omnipotent. This was the Internet after all, and you could be anything you wanted to be… Remaking a new America, one social media post at a time.” (03:09)

• The Inherent Flaw of Utopias (04:55)

  • Quoting Milan Kundera: “Totalitarianism is not only hell, but also the dream of paradise… Once the dream of paradise starts to turn into reality… the rulers of paradise must build a little gulag on the side of Eden. And in the course of time, this gulag grows ever bigger and more perfect, while the adjoining paradise gets even smaller and poorer.”

3. The Cultural Shift: From Diversity to Sameness

• Siegel’s Critique (06:37)
  • “A deadening sameness settled over American culture like a wet wool blanket. Art retreated into a chorus of polite assent... The bedroom became a personal police state.”
  • The Internet’s promise of connectivity and diversity devolved into stifling conformity and constant outrage.

4. The Great Purge and Growing Doubt

• Stone’s Political Loyalty and Disillusionment (07:37)

  • Once a committed Democrat and “good liberal,” Stone supported Obama, Clinton, and Biden, believing in their redemptive promise for the country.
  • “I watched [Biden] speak with tears in my eyes. He will save us, I thought.” (08:26)

• The Turning Point: 2020 Pandemic and Protests

  • Covid shifted her perspective: online activism morphed into mass formation and dogmatic enforcement.
  • “By the end of May, the George Floyd video whipped around the world and before long the whole of society’s efforts had to shift to racial injustice... the lies that were told, the gaslighting, the lurching from one narrative to another, and all of the obedient robots going along with it in full mass formation. It was too much even for me.” (09:17)

• Narrative Manipulation and Election Doubts (10:55)

  • Stone describes her growing mistrust in media and official narratives regarding the 2020 election and protest coverage.
  • “[The system] believed itself to be more powerful than our democracy, more powerful than our elections. I couldn’t go along with that...” (12:50)

5. Politics and Technology: Obama, Google, and the Fact-Check State

• Tech-State Merger (14:35)
  • Siegel and constitutional scholar Adam J. White: Obama’s administration harnessed the power of Silicon Valley to control the flow of information and “nudge” the public toward approved narratives.
  • Quoting Obama from his Google HQ address: “If you give them good information, their instincts are good and they will make good decisions and the president has the bully pulpit to give them good information.”

6. Double Standards: Protest, Power, and Suppression

• Jan 6th vs. BLM (15:59–16:28)

  • Disparate reactions to BLM protests and January 6th riot reveal systemic bias and the new information regime’s power.
  • “The BLM riots attacked working class people, so they didn’t matter, but January 6th attacked the powerful, and that to them meant war.” (15:59)

• Silicon Valley's Coordinated Response (16:28–22:36)

  • Tech giants rapidly deplatform Trump and his supporters, culminating in the shutdown of Parler and broad digital censorship.
  • Siegel: “A cartel of Silicon Valley tech companies had accomplished in days what Congress had failed to do over four years. It shut Trump up… Sovereign are they who control the information.” (21:50)

7. Censorship, Dissent, and the Future

• Historical Parallels and Censorship (22:36)

  • Stone references Thomas Maule’s “Truth Held Forth and Maintained,” highlighting the importance of dissent and how modern mechanisms of social and informational control can suppress it without overt censorship.
  • “Who needs censorship when you have total societal control, at least among the university educated ruling class?” (23:51)

• Illusions of Progress and Warnings for the Present (25:14)

  • Despite the bleak outlook, Stone urges listeners to reclaim authentic and grounded lives outside the digital matrix.
  • “Log off. Migrate back to the real world… It’s probably too late for me. I’m a lifer. I know that. But I’m also a cautionary tale. This is what happens when you spend 30 years of your life in the virtual world. But if I can find my way out, then anyone can.” (26:40)

Notable Quotes & Memorable Moments

• Jacob Siegel: “The ideal in such a system is not to conquer the soul, but to render it obsolete.” (00:39)
• Sasha Stone: “Our utopia was opt in at first, and who wouldn’t want to be a part of it? For a time it felt like the best thing ever. All of our problems solved. It was everything, everywhere, all at once. A whole of society effort.” (05:48)
• Milan Kundera (quoted): “Once the dream of paradise starts to turn into reality, however, here and there people begin to crop up who stand in its way. And so the rulers of paradise must build a little gulag on the side of Eden...” (05:06)
• Siegel: “The global village was not a cross-cultural utopia illuminated by the cosmic light of science… but a claustrophobic orgy of incessant swarming communications that frequently ended in bouts of outrage and cancellation, with everyone crying and the cops getting called.” (06:53)
• Sasha Stone: “We watched them lie. The experts, the journalists, the celebrities, the Democrats.” (09:55)
• Siegel: “Sovereign are they who control the information.” (22:23)
• Sasha Stone: “Log off. Migrate back to the real world… if I can find my way out, then anyone can.” (26:40)

Timestamps of Key Segments

| Timestamp | Segment Description | |-----------|------------------------------------------------------------------------------------------------| | 00:25 | Siegel defines the Information State’s mechanism of control | | 01:13 | Sasha shares her personal motivations for escaping real life into the Internet | | 03:09 | Embracing virtual activism and online progressive utopianism | | 05:06 | Milan Kundera on utopia and the origins of totalitarianism | | 06:37 | Siegel describes the deadening sameness of American culture | | 08:26 | Sasha’s full-throated support for Biden at his 2019 fundraiser | | 09:17 | 2020: Pandemic and George Floyd protests shift societal focus | | 10:55 | Stone’s doubts about election coverage and mainstream media narratives | | 14:35 | Obama’s tech partnership for societal opinion-shaping | | 15:59 | Stone contrasts BLM riots and January 6th treatment | | 16:28 | Siegel chronicles the deplatforming of Trump, Parler’s takedown, and the rise of the info cartel | | 22:36 | Sasha’s historical parallel: free speech and banned pamphleteers in early America | | 25:14 | Stone’s advice: digital detox, reconnect with real life |

Reflections and Closing Thoughts

Sasha Stone narrates a transformation: from architect of progressive digital utopia to dissident documenting its collapse into surveillance and groupthink. By framing her personal odyssey within Siegel’s themes, she examines how idealism on the left paved the way for new forms of institutional control, powered by tech and justified by shifting moral narratives. Listeners are left with caution, nostalgia, and a call to reclaim the real—lest we be swept forever into the glare of algorithmic totality.