Surrounded – Is Wokeness Really The Issue?

Podcast: Surrounded, Jubilee Media
Date: December 28, 2025
Host: John (Jubilee Media)
Featured Guests: Tyler, Jenny, Nick, and Piers Morgan

Episode Overview

This episode of Surrounded dives into the debate over "wokeness" in society and whether it distracts from or even threatens foundational American values such as free speech and meritocracy. With host John facilitating, the conversation spotlights direct debate moments featuring Piers Morgan and perspectives from three Surrounded participants—Tyler, Jenny, and Nick—in a post-show follow-up. The discussion ranges from high-profile political hypocrisies and the evolution of cancel culture to the intricacies of gender identity debates and the economic issues overshadowed by cultural wars.

Key Discussion Points & Insights

1. Hypocrisy in Free Speech Debates

• Tyler vs. Piers Morgan: Calling Out Contradictions
  • Tyler points out contradictions in Piers Morgan’s self-styled image as a champion of free speech, specifically referencing moments where Republican figures restricted speech (e.g., Trump's order to ban flag burning) ([02:31]-[03:14]).
  • Piers concedes, “I don't agree with him,” about Trump's actions, but maintains Republicans are “ferociously free speech” overall ([02:45]-[02:51]).
  • Tyler pushes on accountability: “Your book sets out 'ferociously free speech'. It’s a contradiction.” ([03:17]).
  • Piers and Tyler also discuss Piers' reluctance to challenge guests like Michael Knowles over explicitly anti-free-speech statements ([06:03]-[06:32]).
• Highlight:
  • "Should we just turn or tear page 81 out of your book then?" – Tyler ([03:20])

2. The Scope and Impact of Cancel Culture

• Tyler clarifies that while cancel culture exists on both left and right, recent major threats to free speech have come more from the right—specifically via legislation or executive action ([09:32]-[13:46]).
• The role of corporations and social media as quasi-governmental powers is discussed, drawing parallels between private and public censorship powers ([09:32]-[10:51]).
• Supreme Court rulings around government pressure on social media (e.g., over Covid information) are referenced as examples where the line between government overreach and private moderation blurs ([12:14]-[13:41]).
• Tyler: "The First Amendment was to protect the government from doing that to you. And essentially corporations and public opinion can have very akin powers to the government as well.” ([10:51])

3. Content Moderation & The “Town Square”

• When pressed about platforms best managing free speech, Tyler favors YouTube's current policies while criticizing Elon Musk’s inconsistent stewardship of X (formerly Twitter), and calls for future government standards on digital public squares ([17:00]-[18:56]).
• Tyler: “When you are banning people and stuff like this, I do think you’re essentially banning areas of the town square. And I do think that the government needs to do something about that.” ([18:29])

4. Debating Extremes and Platforming Responsibility

• Tyler defends the value of engaging even the far-right or conspiracy theorists, noting that not doing so is intellectual laziness. He advocates coming prepared and sees discussion as vital to democracy ([19:16]-[22:12]).
• Emphasizes that “platforming is not the problem. It’s just platforming responsibly or prepared platforming is the way to do it.” ([26:48])
• On debating the far-right:
  • “I hate when people say you can't argue against fascism. ... You need to be able to argue why a democratic system with laws that are not applied arbitrarily is superior to fascism on a moral level.” – Tyler ([19:16])

5. “Woke” Issues vs. Material Policy

• Nick argues that “woke” politics serve as a distraction from economic and material issues that most affect everyday lives—like jobs, housing, and healthcare ([42:43]-[54:09]).
• Debates about meritocracy:
  • Piers expresses concern about equity/identity politics overtaking merit: “It only matters if the black trans leader of a company has only got that job because they're black and trans and not on ability.” ([52:29])
  • Nick responds: “The people getting tens of millions of stock options are not my priority. It's the person making minimum wage, that's my priority.” ([52:51])
• Nick on wedge issues: “They find these things that can drive a—find a values gap between different groups in the population that might have 90% of their interests overlap, but there's this one issue they disagree on and it clouds out everything else.” ([53:02])

6. The Debate Over Gender, Pronouns, and Social Constructs

• Jenny’s Approach: Empathy & Clarity
  • Jenny recounts her discussion with Piers Morgan, focusing on the distinction between gender (a social construct), biological sex, and societal respect ([34:01]-[36:04]).
  • Criticizes Piers’ debate tactic of redirecting discussions away from nuanced points ([34:54]).
  • “What I intended was that ethnicity is like something that is biologically determined, right? ... But how we decide to express ourselves in society, to feel true to ourselves, that is a construct, that is a creation.” – Jenny ([35:12])
  • Argues for normalizing pronoun sharing as basic courtesy and to foster inclusion ([38:29]-[39:45])
• Jenny directly addresses Piers at the end:
  • “I hope that the spirit of discussion continues ... it’s so much more important that we are able to open our minds and learn from each other rather than try and prove each other wrong, pin each other in a corner.” ([40:10])

7. Political Consequences and the Nature of Public Attention

• Tyler predicts there will be little political cost for overt free speech violations: "I think most people don't like free speech... I do not anticipate direct consequences for that sort of behavior." ([14:57])
• Nick discusses how leaders like Obama moved past wedge issues through targeted message discipline, but worries modern politics is dominated by whatever garners the most attention, rather than the most importance ([55:26]-[56:57]).

Notable Quotes & Memorable Moments

• On Free Speech and Contradiction:
  • “Should we just turn or tear page 81 out of your book then?” – Tyler to Piers Morgan ([03:20])
• On Platforming Debate Opponents:
  • "Platforming is not the problem. It's just platforming responsibly or prepared platforming is the way to do it.” – Tyler ([26:48])
• On Social Respect and Pronouns:
  • "If it makes one less person or one person feel a little less alone in the world and it does no harm ... then why is that a problem?" – Jenny ([39:45])
• On Wedge Issues and Distraction:
  • “They find these things that can drive a values gap ... but there's this one issue they disagree on and it clouds out everything else.” – Nick ([53:02])

Timestamps for Important Segments

• [02:31]-[03:24]: Tyler calls out Piers’ “ferocious free speech” claim with examples from recent GOP policy.
• [05:41]-[06:41]: Discussion about holding Michael Knowles accountable on air.
• [09:32]-[13:46]: Cancel culture, government pressure, and the First Amendment.
• [17:00]-[18:56]: Debate on content moderation – YouTube vs. X vs. government standards.
• [19:16]-[22:12]: Tyler’s arguments for debating even extremists.
• [34:01]-[36:04]: Jenny explains distinctions between sex, gender, and respect.
• [42:43]-[54:09]: Nick and Piers’ debate on whether “woke” issues distract from real problems.
• [52:29]-[53:02]: Clash on meritocracy vs. identity politics.

Tone & Approach

The conversation is lively and direct, mixing pointed critique and structured argumentation with moments of humor and candor. Tyler adopts an assertive, fact-driven style; Jenny brings empathy and calm rationale; Nick is analytical, focused on economic outcomes and structural issues. Piers Morgan is combative, using provocative hypotheticals to challenge the panel.

Summary

Is wokeness really the issue? This Surrounded episode shows it depends on whether you see the greatest threat as ideological excess, hypocrisy, or neglect of material well-being. The guests and Piers Morgan argue fiercely over where free speech is truly threatened, whether cancel culture has gone too far—and by whom—and whether identity-based debates are overshadowing most Americans’ everyday struggles. While sharp in disagreement, nearly all participants ultimately call for more rigorous, well-prepared engagement across lines of difference, echoing the spirit of Surrounded: that meaningful debate, not echo chambers or avoidance, is what democracy needs.