

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.
Episodes
Mentioned books

Aug 31, 2025 • 1h 47min
Patrick Bet-David vs 20 Anti-Capitalists
Patrick Bet-David, a bold entrepreneur and founder of Valuetainment Media, engages in a spirited debate with 20 anti-capitalists. He defends capitalism's role in reducing poverty and challenges the feasibility of wealth redistribution. The conversation delves into the ethics of profit in healthcare, critiques historical economic systems, and debates personal responsibility and employment opportunities. With passionate arguments, Bet-David navigates through the ideological complexities of capitalism versus socialism, all while addressing the societal implications of economic disparities.

Aug 24, 2025 • 57min
How Radical Is Amanda Seales? | Surrounded Follow-Up
Amanda Seales, a comedian and social commentator known for her sharp insights, joins John Regalado to discuss memorable moments from her heated debate with black conservatives. She dives into the necessity of reparations and critiques policing, advocating for alternatives like socialism to uplift Black Americans. Amanda reflects on the complexities of racial dialogue and challenges surrounding systemic racism, emphasizing the importance of cultural identity and community engagement in political discussions.

Aug 17, 2025 • 1h 36min
Amanda Seales vs 25 Black Conservatives
Join Amanda Seales, a dynamic comedian and cultural critic, as she faces off against 25 Black conservatives in a thought-provoking discussion. They tackle the complexities of reparations, debating whether financial compensation is justified or if education holds more weight. The talk shifts to systemic racism, underinvestment, and the realities of Black-on-Black crime, with personal stories shedding light on community resilience. With a focus on political representation and the nuances of identity, this conversation challenges conventional views and demands deeper understanding.

Aug 10, 2025 • 1h 8min
Why Cenk Uygur Thinks It’s All One Big Scam
Cenk Uygur, co-founder of The Young Turks and a vocal progressive, joins John Regalado to dissect the political landscape. They discuss how both Republicans and Democrats cater to donors, labeling the system as a scam. Cenk critiques identity politics and the need for Democrats to adopt a genuine populist approach. He expresses frustration over unfulfilled promises by Democratic leaders and highlights the growing disconnect between political elites and everyday citizens. The conversation also addresses the challenges of diversity initiatives and the potential for a third political party.

Aug 3, 2025 • 1h 44min
Cenk Uygur vs 20 Democrats & Republicans
Cenk Uygur, a Turkish-American political commentator and co-founder of The Young Turks, passionately debates 25 Democrats and Republicans on fundamental issues. He argues that both parties often sidestep critical economic concerns through culture wars, pointing out that the Democratic agenda leans more on marketing than real change. He claims corporate money dominates political power, serving the wealthy's interests over the working class. The discussion challenges listeners to rethink activism and political engagement in a climate of misinformation.

Jul 26, 2025 • 1h 11min
Can 1 Cop Defend Himself Against 20 Criminals? | Surrounded
Kevin Donaldson, a retired New Jersey police officer, engages in a thought-provoking dialogue with 20 individuals who have criminal records. They tackle critical issues of police accountability and the use of lethal force. Donaldson defends claims of officer honor and integrity, while discussing the complexities of racial profiling and public perception. The conversation dives deep into necessary reforms in policing training and emphasizes the importance of community trust. Can understanding bridge their vastly different experiences?

21 snips
Jul 20, 2025 • 1h 42min
Mehdi Hasan vs 20 Far Right Republicans
Join Mehdi Hasan, a progressive journalist known for his sharp political insights, as he confronts 20 far-right Republicans in a heated debate. He boldly asserts that Trump is pro-crime and defies the Constitution. The discussions span immigration's pivotal role in America, the validity of presidential pardons, and the nuanced complexities of the Gaza conflict. Hasan delves deep into issues of citizenship, democracy, and accountability, challenging opposing views with fervor and well-researched arguments, all while navigating a politically charged atmosphere.

Jul 13, 2025 • 1h 35min
Charlie Kirk vs 20 Liberal College Students
In this lively discussion, Charlie Kirk, founder of Turning Point USA and known for his conservative activism, faces off against a group of 20 liberal college students. He passionately defends controversial views, claiming abortion is murder and asserting that college is a scam. The debate about gender identity heats up as Kirk challenges the notion of trans women being women. Topics also include the implications of Kamala Harris's DEI candidacy and a critical look at the value of college education in today’s economy. Expect fiery exchanges and thought-provoking arguments!

11 snips
Jul 6, 2025 • 35min
Is Candace Owens Living the Feminist Dream? | Surrounded Follow-Up
Candace Owens, a cultural and political commentator known for her conservative stance, joins John Regalado for a thought-provoking discussion. They reflect on her recent debate with feminists, diving into her perspectives on feminism, motherhood, and societal expectations. Owens challenges traditional views on women's fulfillment, arguing that authentic choices matter more than societal definitions of success. The conversation also explores shifting gender roles and the impact of modern feminism on family dynamics, all while navigating the complexities of content creation.

9 snips
Jul 3, 2025 • 2h 2min
Destiny vs 25 Donald Trump Voters
Destiny, a well-known online streamer and political commentator, engages in an intense debate with 25 Trump supporters. He presents bold claims about Trump’s fitness for presidency and contrasts his policies with Kamala Harris's immigration plan. The discussion dives into the Capitol riot's implications, the complexities of U.S. immigration laws, and the economic impacts of both administrations. Through fiery exchanges, Destiny challenges misinformation and highlights the importance of civil discourse in political debate.