

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

Dec 14, 2025 • 1h 40min
James Talarico vs 20 Undecided Voters
Texas State Representative James Talarico, a former middle school teacher and Presbyterian seminarian, takes on 20 undecided Texas voters about critical issues. He argues that cuts to healthcare and food assistance harm all communities and emphasizes that immigrants strengthen the nation’s economy. Talarico advocates for a public option in healthcare and stresses the importance of grassroots organizing to tackle big money in politics. He also insists that the real divide isn't left vs. right, but the interests of working people against the wealthy elite.

Dec 7, 2025 • 1h 49min
Doctor Mike vs 20 RFK Jr. Supporters
Dr. Mike, a board-certified family medicine physician and popular health educator, engages with 20 RFK Jr. supporters in a spirited debate on public health issues. He argues that RFK Jr. is damaging the well-being of the nation and needs to resign as HHS Secretary. Discussion centers around the impact of the MAHA movement on the doctor-patient relationship, trust in science versus skepticism, and the risks associated with unregulated supplements. Medical expertise is tested against a backdrop of contrasting beliefs about health, government actions, and the future of healthcare.

Nov 30, 2025 • 1h 55min
Piers Morgan vs 20 Woke Liberals
In a heated discussion, Piers Morgan, an English journalist and broadcaster known for his outspoken views, confronts 20 woke liberals on various cultural issues. He argues that masculinity isn't toxic and critiques woke ideology as undermining liberal values. Piers challenges the purpose of gender-neutral pronouns and the implications of cancel culture on free speech. The debate dives into the impact of modern masculinity, the role of figures like Andrew Tate, and the intersection of cultural and economic issues, leaving listeners to ponder the complexities of today's social landscape.

Nov 26, 2025 • 1h 44min
Tim Miller vs 20 Gen Z Conservatives
Tim Miller, a former Republican strategist turned Democratic commentator, engages in a lively debate against 20 Gen Z conservatives. He labels ICE as a fascist entity, arguing against its practices and advocating for humane immigration solutions. Tim critiques the Trump administration for undermining American values and highlights the toll of gun rights, suggesting that safety measures similar to car regulations could reduce gun fatalities. The conversation also touches on the comparative governance of red and blue states, urging a more humanized approach to political discourse.

Nov 23, 2025 • 1h 10min
Is Bryan Johnson's Immortality a Hoax? | Surrounded Follow-Up w/ Chelsea Gods & Bryton Snyder
Chelsea Gods, a social activist known for her class-focused commentary, and Bryton Snyder, a student and fitness enthusiast, take a deep dive into Bryan Johnson's 'Don't Die' philosophy. Chelsea questions the privilege behind longevity pursuits, advocating for systemic change over personal vanity projects. Bryton adds a philosophical layer, discussing how life's finitude drives meaning and warning of the inequality risks posed by life-extension technologies. Together, they challenge the implications of chasing immortality while emphasizing the value of the human experience.

6 snips
Nov 16, 2025 • 1h 38min
Bryan Johnson vs 20 Skeptics
Bryan Johnson, a tech entrepreneur and founder of the 'Don't Die' movement, argues passionately for prioritizing anti-aging interventions. He believes that defeating death should be humanity's top goal, even as Chelsea Godz challenges him on the socioeconomic implications and ethical concerns surrounding access to longevity treatments. The conversation dives into whether AI can realistically conquer mortality, the meaning of life without a deadline, and the societal risks of universal longevity. Johnson emphasizes the need for cultural and systemic changes in food and health, while Godz advocates for addressing real-world constraints.

Nov 9, 2025 • 1h
1 Politician vs 25 Undecided Voters (Feat. Pete Buttigieg) | Surrounded Rewind
Pete Buttigieg, former mayor and Afghanistan war veteran, engages with 25 undecided voters leading up to the 2024 election. He makes a compelling case for Kamala Harris, arguing her motivations are centered on public service while contrasting them with Donald Trump’s self-interest. Buttigieg discusses Harris’s economic vision for the Midwest and her plans to sustain job growth. He tackles issues like rights, crime reduction, and diversity, defending Harris's record and approach. Voters reflect on how his insights influenced their decisions.

Nov 2, 2025 • 49min
What's the Future of The Democrats' Platform? | Surrounded Follow-Up w/ Luke Beasley
Luke Beasley, a political commentator known for engaging conservative audiences, joins John Regalado to dive deep into his recent debate with MAGA Boomers. They explore whether political extremism is more prevalent on the left or right, and discuss economic competence among parties. Beasley argues that Democrats should reclaim their narrative on economic issues and critiques their messaging. He also shares insights on generational differences in political debates and reflects on the role of social media in polarization.

Oct 26, 2025 • 1h 43min
20 Boomer Trump Supporters vs 1 GenZ Liberal (ft. Luke Beasley) | Surrounded
Luke Beasley, a Gen Z liberal political commentator, takes on 20 boomer Trump supporters in a lively debate. He argues that MAGAnomics negatively impacts the economy and claims Trump poses an authoritarian threat to democracy. The discussion ranges from whether Trump supporters truly embody patriotism to the effects of political violence. Luke also proposes that Kamala Harris would have made a better president, sparking hot exchanges over qualifications and policies. Throughout, he emphasizes the importance of civil discourse amid deep divides.

Oct 19, 2025 • 58min
Is There Only One Way to Read the Bible? | Surrounded Follow-Up w/ Allie Beth Stuckey
Allie Beth Stuckey, a Conservative Christian commentator and author of 'Toxic Empathy,' engages with John Regalado on faith and societal issues. They dive into the complexities of homosexuality in the Bible and the moral implications of abortion. Allie argues that laws reflect moral beliefs and discusses the importance of distinguishing faith from political ideologies. She challenges the notion of toxic empathy and addresses the church's stance on same-sex marriage, advocating for loving dialogue while maintaining doctrinal integrity.


