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Surrounded

Jubilee Media

Welcome to Surrounded, where one brave person faces twenty five. Every Sunday, dive into bold debates as a single guest takes on twenty five people with opposing views. No echo chambers, just raw, unfiltered conversations that challenge assumptions and spark connection.If you’re hungry for perspective, ready to wrestle with complexity, and believe in the power of debate, you’re in the right place. Subscribe now and join a community built on curiosity, empathy, and conversation that matters.

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  • 34 episodes
  • weekly
  • Avg 1 hr 19 min
  • English
Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.
  • Wednesday · 40 min

    Harry Sisson Reacts to His Viral Debates | Surrounded Follow-Up

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@nectarcrush Instagram: https://www.instagram.com/nectarcrush Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com TIMECODES 00:00 Intro 2:41 Clip 1 8:23 Clip 2 13:58 Clip 3 22:32 Clip 4 29:32 Clip 5

    • Transcript
  • November 1 · 1 hr 45 min

    1 Liberal Man vs 20 MAGA Conservatives (ft. Harry Sisson) | Surrounded

    One liberal voice stands in the center of twenty staunch conservatives in this high-intensity episode of Jubilee’s Surrounded. Political commentator and creator Harry Sisson steps into the ring to take on 20 MAGA supporters head-to-head on the most divisive issues facing modern America. From immigration policy and political violence to healthcare outcomes and federal corruption, Harry defends four contentious claims against fierce opposition. Can common ground emerge when ideological opposites collide, or does the debate only deepen the divide?

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  • October 28 · 1 hr

    Farha Khalidi Reacts To Her Viral Debates | Surrounded Follow-Up

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@lovecommanectar Instagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com

    • Transcript
  • October 25 · 1 hr 54 min

    1 OF Model vs 20 Anti-S*x Work Advocates (ft Farha Khalidi) | Surrounded

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: / jubileemedia TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com FEATURING Farha: / farhakhalidi / farhakhalidi

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  • October 18 · 1 hr 6 min

    David Breaks Down His Debates with Conservatives | Surrounded Follow-Up

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@lovecommanectar Instagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com FEATURING David Mauricio: https://www.instagram.com/david.mauriciooo?mdxt=eXJ2Nmd3aHcwOTFx https://www.tiktok.com/@david_mauricioo?_r=1&_t=ZP-9AUv5GiuWOE https://youtube.com/@david_mauricioo?si=dcAq3F_PHUoFYU5a TIMECODES 00:00 Intro 02:40 Clip 1 23:40 Clip 2 29:21 Clip 3 38:55 Clip 4 46:10 Clip 5 57:44 Clip 6

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  • October 4 · 50 min

    Evan Revisits His Most Viral Debates | Surrounded Follow-Up

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@lovecommanectar Instagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com TIMECODES 00:00 Intro 03:07 Clip 1 09:22 Clip 2 27:19 Clip 3 41:04 Clip 4

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  • September 27 · 1 hr 45 min

    Andrew Yang vs 20 AI Optimists | Surrounded

    Andrew Yang faces 20 AI optimists in Jubilee’s Surrounded, defending four provocative claims: AI will accelerate inequality, eliminate jobs faster than new ones can emerge, make Universal Basic Income necessary, and push markets to prioritize profit over human dignity. Will Yang’s warnings withstand the optimism—or will the AI believers dismantle his case?

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  • September 20 · 51 min

    Is This Conservative Actually Pro-Reparations? | Surrounded Follow Up

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@lovecommanectar Instagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com TIMECODES 00:00 Intro 03:23 Clip 1 14:43 Clip 2 26:28 Clip 3 38:40 Clip 4

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  • September 13 · 1 hr 54 min

    1 Conservative vs 20 Liberals (ft. The Split’s Austin Julio Broughton) | Surrounded

    Austin Julio Broughton steps into the hot seat on Jubilee’s Surrounded to defend four incendiary claims against 20 Liberals: The Left cares more about LGBTQ+ issues than Black Americans. Elective abortion is modern America’s greatest moral failure. Civil rights were won with Bibles and churches, not pronouns and DEI. Republicans care more about free speech than Democrats. Will Austin hold the line against overwhelming odds, or will the room shut him down?

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  • September 6 · 30 min

    Gen Z and The American Dream | Surrounded Follow Up w/Maxwell Frost

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@lovecommanectar Instagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com TIMECODES 00:00 Intro 2:27 Clip 1 11:10 Clip 2 19:08 Clip 3

    • Transcript
  • August 30 · 1 hr 54 min

    1 Young Politician vs 20 Boomers (ft. Maxwell Frost) | Surrounded

    Maxwell Frost takes center stage in Jubilee’s Surrounded, facing off against 20 Boomers to defend four hard-hitting claims: Gen Z is the most politically active generation in American history, they aren't too spoiled or lazy, all student debt should be canceled, and while Boomers lived the American Dream, Gen Z can only read about it. Can the youngest member of Congress hold his own against a room full of seasoned skeptics, or will the generational divide prove too wide to cross?

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  • August 19 · 56 min

    Tim Pool vs Progressives | Surrounded Follow-Up

    Hey you 👈 Wanna be in a Jubilee video? https://bit.ly/be-in-a-video LET’S BE FRIENDS Instagram: https://www.instagram.com/jubileemedia/ TikTok: https://www.tiktok.com/@jubilee?lang=en Website: https://www.jubileemedia.com OUR LOVE + DATING CHANNEL 🍑 YouTube: https://www.youtube.com/@lovecommanectar Instagram: https://www.instagram.com/lovecommanectar Nectar app: https://lovecommanectar.co/m/download-nectar ARE YOU A BRAND? WANNA WORK WITH US? Email partnerships@jubileemedia.com TIMECODES 00:00 Intro 02:47 Clip 1 18:38 Clip 2 33:28 Clip 3 44:03 Clip 4

    • Transcript
  • August 16 · 1 hr 40 min

    1 Moderate vs 20 Progressives (ft. Tim Pool)

    Tim Pool steps into the ring with 20 progressives in this explosive episode of Jubilee’s Surrounded. Standing alone as the sole moderate voice, Pool defends four radical premises: the mainstream left commits more violence than the mainstream right, the Democratic Party has fully embraced authoritarianism, America is actively heading toward a civil war, and the U.S. Constitution effectively no longer exists. Will Tim withstand the crossfire, or will the consensus collapse his defense?

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  • August 2 · 1 hr 59 min

    1 Black Conservative vs 20 Black Liberals (ft. Officer Tatum)

    Officer Tatum steps into the center of Jubilee’s Surrounded to take on 20 Black Liberals in a high-stakes debate over race, politics, and responsibility. He stands alone to defend four explosive claims: Trump and the GOP are better for the Black community than Democrats, police do more good than harm, Black-on-Black crime is the most critical threat, and systemic racism is used as an excuse to avoid personal accountability. Will Tatum hold his ground under heavy fire, or will the panel dismantle his conservative playbook?

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  • July 27 · 50 min

    What Has The Manosphere Taught Us? | Surrounded Follow-Up

    Mark Manson steps outside the circle to unpack his debate with 20 manosphere creators. Is the manosphere helping men—or trapping them in an echo chamber of insecurity? What We Unpack in This Episode The Looksmaxxing Trap: Why hyper-focusing on superficial traits turns dating into a transaction—and leaves men feeling more isolated than ever. Echo Chambers vs. Reality: How the manosphere monetizes male insecurity and converts genuine loneliness into online hostility. The Middle School Mindset: Uncovering why so many digital "alphas" struggle to build lasting, adult relationships. Redefining Modern Masculinity: What self-improvement actually looks like when you strip away the posture, the performance, and the podcasts.

  • July 27 · 1 hr 24 min

    1 Anti-Manosphere vs 20 Manosphere (ft. Mark Manson) | Surrounded

    Mark Manson steps into the circle against 20 manosphere creators in Jubilee’s Surrounded, defending four hard-hitting claims: the manosphere is a predatory business profiting off male anger, a woman's body count is irrelevant, porn has ruined men far more than feminism, and true attractiveness stems from respecting women. Will Manson dismantle the echo chamber with reason, or will the pack overrun him? They debate the 4 following claims that Mark Manson, has: 1. The manosphere is a business that profits off keeping men angry, 2. A woman's body count doesn't matter, 3. Porn has done more damage to men than feminism has, 4. The most attractive men are those who respect women

  • July 12 · 1 hr 3 min

    How Can You Care But Not Vote? | Surrounded Follow-Up

    John Regalado sits down with non-voter Carlheb to unpack their recent Surrounded debate with Wes Moore. In this follow-up, they discuss the moral tension that comes with participating in an imperfect and often corrupt system, the legacy of slavery in the current political consciousness, the influence of black revolutionaries like Fred Hampton, and whether or not Wes Moore convince Carlheb to cast his vote in future elections.

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  • July 5 · 1 hr 21 min

    Governor Wes Moore vs 20 Non-Voters | Surrounded

    Democratic leader Wes Moore faces 20 non-voters in a compelling episode of Surrounded, tackling political disillusionment head-on. He challenges the room with three urgent claims: 1) nothing shapes policy more effectively than your vote, 2) bad politics thrive when citizens don’t participate, and 3) abstaining from the ballot protects corruption rather than protesting it. Can Moore convince a skeptical crowd to reclaim their civic power, or will their disillusionment prove too deep to overcome?

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Showing 1–20 of 34 episodes