PODCAST · society
Surrounded
by 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.
Episodes
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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:...
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1 Liberal vs 20 MAGA (ft. The Split’s David Mauricio) | Surrounded
In this episode of Surrounded, commentator David Mauricio from The Split steps into the hot seat as one liberal voice facing off against 20 MAGA debaters.
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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:...
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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...
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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:...
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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,...
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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:...
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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…
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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:...
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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...
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Is Trump Better for Black Americans Than Democrats? | Surrounded Follow-Up w/ Officer Tatum
On this week's episode, Officer Brandon Tatum joins host Parris Rose to recap Tatum's time in the Surrounded Circle. They discuss several clips with the guest debators, and break down some of the most heated moments of the discussion.
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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...
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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…
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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...
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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...
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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...
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Is Dean Alpha or Beta? | Surrounded Follow-Up
John Regalado sits down with Lori and Julia Kate to unpack their viral Surrounded debate with Dean Withers. In this follow-up, they dive deeper into their personal backgrounds and values, their perspectives on Donald Trump, and discuss the discourse of modern political commentary.
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Dean Withers vs 20 MAGA Women | Surrounded
APPLY TO BE ON SURROUNDED: https://bit.ly/43MF3yZ Open General Casting Application: https://bit.ly/4xCliYn 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:...
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Is Dave Rubin Living in Reality? Surrounded Follow-Up
Kyla Turner steps outside the circle to join John Regalado in this follow-up to the viral Dave Rubin Surrounded debate. In this discussion, Kyla shares her perspective on the debate – covering the perceived contradictions of Rubin's political alignment and identity, political extremism in…
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Is Trump Losing Support For The War? | Surrounded Follow-Up
Kikoff: Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!John Regalado sits down with Mat Nuclear to unpack his recent Surrounded debate with Glenn Greenwald. In this follow-up interview, John and Mat…
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1 MAGA Republican vs 20 Far-Left Democrats (ft Dave Rubin) | Surrounded
Conservative commentator Dave Rubin enters the Surrounded circle to confront 20 far-left Democrats in an intense political showdown. In this episode, Rubin navigates a deeply hostile environment, defending four divisive claims: that "wokeism" has caused more damage to America than Donald Trump,...
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1 Journalist vs 20 Trump Supporters (ft Glenn Greenwald) | Surrounded
Independent journalist Glenn Greenwald steps into the circle to confront 20 MAGA supporters in a fiery political showdown. In this episode, Greenwald takes direct aim at the movement's core beliefs with four explosive claims: Trump’s legacy is defined by war rather than peace, his administration...
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Naima vs Charlie Kirk, 1 Year Later | Surrounded Follow-Up
John Regalado sits down with recurring Surrounded guest, Naima, to look back at some of her most memorable moments from the Surrounded circle. In this special episode, Naima and John discuss whether Charlie Kirk's assassination changed how she views debate, what it was like to become a political...
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1 Psychiatrist & 20 Depressed People (ft. Dr. K) | Surrounded
Kikoff: Build credit fast and get your first month for just a dollar at getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!Psychiatrist Dr. K sits down with 20 individuals battling depression in a raw and deeply personal conversation about the realities of mental health. In this...
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Israeli vs Palestinian: Can They Agree? | Surrounded Follow-up (ft. Rudy Rochman and Dr. Ahmed Soboh)
John Regalado is joined by Rudy Rochman and Dr. Ahmed Soboh to revisit their recent Surrounded debate about the Israeli-Palestinian conflict. In this follow-up, they discuss religious extremism on both sides of the conflict, what major compromises both Rudy and Ahmed would consider acceptable in...
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1 Israeli vs 20 Pro-Palestine (ft. Rudy Rochman) | Surrounded
Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us! Jewish and Israel rights activist Rudy Rochman rights activist Rudy Rochman faces 20 pro-Palestinian advocates in a deeply emotional and urgent debate over…
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Why a Conservative and Liberal Agree on the Epstein Files | Surrounded Follow-Up
John Regalado sits down with Andrew (Liberal) and Marien (Conservative) from Ro Khanna’s Epstein Files Surrounded debate to unpack the fallout. They revisit why the Epstein Transparency Act fell short, whether holding the “Epstein class” accountable has become empty political rhetoric, and if...
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1 Congressman vs 20 Epstein File Critics (ft. Ro Khanna) | Surrounded
Representative Ro Khanna enters the circle to face 20 Americans in a high-stakes debate about power, privilege, and the Epstein files. In this episode of Surrounded, Khanna navigates a deeply polarizing political landscape, defending four uncompromising claims: that America's justice system is...
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Why Are Vegans So Annoying? | Jack Symes Surrounded Follow-up
Philosopher and author Dr. Jack Symes and John Regalado meet again to dissect Jack's Surrounded debate with 20 meat eaters. In this follow-up, they examine the moral weight of animal suffering, the scientific data behind plant-based longevity, and the controversial argument that modern food…
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1 Vegan vs 20 Meat Eaters (ft. Jack Symes)
Build credit fast and get your first month for just a dollar at https://getkikoff.com/SURROUNDED today. Thanks to Kikoff for sponsoring us!Vegan advocate Jack Symes enters the circle to face 20 meat-eaters in an intense debate about the ethics of our diets. In this episode of Surrounded, Symes...
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Top 5 Most Heated Debates | Surrounded
In this compilation episode of Surrounded, we revisit the most explosive and polarizing debates of the past year. One by one, these guests stepped into the circle to face 20 opposing voices in high-stakes clashes. Watch as Sam Seder takes on conservatives over DEI, Candace Owens defends…
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Is Body Positivity Disempowering? Follow-up (ft. Jillian Michaels) | Surrounded
Fitness icon Jillian Michaels sits down with John Regalado and body positivity advocate Marcy Guevara to unpack the emotional fallout from her Surrounded debate. In this follow-up, they dive into the "primary wound" of childhood trauma, the conflict between movement loyalty and personal health…
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Jillian Michaels vs 20 Body Positivity Activists
Fitness trainer Jillian Michaels enters the circle to face 20 body-positivity advocates in a high-stakes debate about the future of wellness. In this episode of Surrounded, Michaels navigates a deeply personal and polarizing landscape, defending four core claims: the body-positivity movement is...
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Why It Always Comes Back to Butt Stuff | We Followed Up With Zander Moricz
John Regalado sits down with Zander Moricz, to revisit the most heated moments of his surrounded debate. They discuss Trans Youth, misinformation, and the future of LGBTQ+ politics. Follow our YouTube channel: https://www.youtube.com/@jubilee Follow Zander Moricz & SEE Alliance:...
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1 LGBTQ+ Activist vs 25 Conservatives (ft. Zander Moricz)
One LGBTQ+ activist is surrounded by twenty-five conservatives in a raw conversation about identity, power, and the future of America’s youth. Zander Moricz steps into the circle to challenge assumptions and open a dialogue. From banned books to drag queens, healthcare to political power, this...
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Can Talarico Turn Texas Blue? | James Talarico vs 20 Undecided Voters Surrounded Follow-Up
John Regalado sits down with Texans Krista and Daniel, to revisit their Surrounded debate with James Talarico. In this follow up interview they discuss whether or not Talarico can truly deliver on the change he's promising, whether billionaires or ideology are dividing us, and what the point of...
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Has the FBI Always Been Corrupt? | 1 Ex-Mafia Boss vs 20 Cops Surrounded Follow-Up
John Regalado is joined by retired FBI agent Tom and veteran police officer Heather to unpack the most revealing moments from their Surrounded debate with ex-Mafia Boss, Michael Franzese. In this follow-up interview, they dig into the deep mistrust between the American public and the FBI, why...
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Are Conservatives the Snowflakes Now? | Isaiah Martin Surrounded Follow-Up
Isaiah Martin sits down with John Regalado to unpack the most heated moments from his Surrounded debate with 20 MAGA Republicans. In this follow-up, they dive into immigration myths, Trump’s economic record, why Isaiah calls DOGE a failure, and how misinformation spreads in real time. Isaiah also...
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Isaiah Martin vs 20 MAGA Republicans
Isaiah Martin steps into Surrounded as the lone Democrat facing 20 MAGA Republicans. He challenges four core pillars of Trump’s agenda: that mass deportations make communities less safe, Trump serves the wealthy while leaving everyday Americans behind, DOGE was a complete failure, and Trump’s...
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Has the Healthcare Industry Betrayed Us? | Doctor Mike Surrounded Follow-Up
John Regalado sits down with Bryan, Anastasia, and Jack to unpack the most revealing moments from their Surrounded debate with Doctor Mike. In this follow-up interview, they dig into the deep mistrust between everyday people and the medical establishment, why skepticism around Big Pharma keeps...
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Ex-Mafia Boss vs 20 Cops
Ex–mafia boss Michael Franzese steps into the Surrounded circle to face 20 cops in a rare role reversal. He challenges four core assumptions about modern policing: that undercover stings often manufacture crime, that law enforcement justifies breaking the law to catch criminals, that success is...
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Gen Z’s Being Fed Fascism
Adam Mockler joins John Regalado to revisit the most charged moments from his Surrounded debate with 20 conservative college students. In this follow-up, Adam unpacks the rise of political extremism among young voters, how inflammatory rhetoric becomes normalized from the top down, why Trump’s...
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Adam Mockler vs 20 Gen Z Conservatives
It’s one liberal college dropout against 20 conservative college students. Adam Mockler steps into the Surrounded circle to defend four provocative claims: Trump is fueling a rise in fascism among young people, the economy is not in a so-called “golden age,” children are safer with the average...
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Is Wokeness Really The Issue?
John Regalado sits down with Tyler, Jenny and Nick – participants from the Surrounded episode featuring Piers Morgan – to unpack the moments that sparked the most friction in their debate. In this follow-up, they dig deeper into their conversations around free speech absolutism, whether…
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Why Gen Z Politics Have Become So Extreme
Tim Miller joins John Regalado to revisit some of the most thought-provoking moments from his Surrounded debate with 20 Gen Z conservatives. In this follow-up interview, Tim and John explore generational shifts on the right, how extreme immigration tactics and ICE enforcement become normalized…
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James Talarico vs 20 Undecided Voters
Texas State Rep. James Talarico joins Surrounded to face 20 undecided Texas voters in a conversation about policy, power, and what’s at stake in 2026. He argues that cuts to healthcare and food assistance hurt everyone, that immigrants make America stronger and more prosperous, that every vote…
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Doctor Mike vs 20 RFK Jr. Supporters
Doctor Mike sits down with 20 RFK Jr. supporters in a heated debate over trust, science, and the future of public health. He argues that RFK Jr. is harming the nation’s wellbeing and should step down as HHS Secretary, that the MAHA movement is undermining the doctor–patient relationship, that Big...
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Piers Morgan vs 20 Woke Liberals
Piers Morgan steps into Surrounded to face 20 “woke liberals” in a charged cultural showdown. He defends four blunt claims: masculinity has never been toxic, woke ideology is anti-liberal and veers toward the fascistic, gender-neutral pronouns serve no purpose, and cancel culture poses a real...
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Tim Miller vs 20 Gen Z Conservatives
Tim Miller, a former Republican strategist turned Democrat, faces 20 Gen Z conservatives in a tense generational face-off. He argues that ICE has become a fascist institution, that gun rights aren’t worth the lives lost, that the Trump administration undermines American values, and that red…
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Is Bryan Johnson's Immortality a Hoax? | Surrounded Follow-Up w/ Chelsea Gods & Bryton Snyder
John Regalado sits down with Chelsea Gods and Bryton Snyder to dive deeper into some of the most thought-provoking moments from their Surrounded debate with Bryan Johnson. In this follow up interview, Chelsea and Bryton discuss their criticisms of Bryan's "Don't Die" philosophy, the value of a...
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ABOUT THIS SHOW
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.
HOSTED BY
Jubilee Media
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Frequently Asked Questions
How many episodes does Surrounded have?
Surrounded currently has 64 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Surrounded about?
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...
How often does Surrounded release new episodes?
Surrounded has 64 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Surrounded?
You can listen to Surrounded on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Surrounded?
Surrounded is created and hosted by Jubilee Media.
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