

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

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.

11 snips
Oct 12, 2025 • 1h 44min
Allie Beth Stuckey vs 25 Liberal Christians
Allie Beth Stuckey, a conservative Christian commentator and author of 'Toxic Empathy,' engages in a captivating debate with 25 liberal Christians. She defends her views on marriage, arguing it should remain a union between a man and a woman, and addresses the complexities of same-sex relationships. Stuckey also labels abortion as a grave moral evil, emphasizing biblical teachings. Additionally, she controversially claims that empathy can sometimes lead to sin when divorced from truth, and contends that progressivism clashes with core Christian beliefs.

Oct 5, 2025 • 1h 1min
Are We Really Going To End All Abortions? | Surrounded Follow-Up w/ Lila Rose
Lila Rose, a prominent pro-life activist and founder of Live Action, joins John Regalado for a thought-provoking discussion on abortion. They delve into the Catholic perspective on sex and reproduction, debating when life truly begins. Lila shares her vision of eliminating abortions through enhanced social support and cultural shifts. She also tackles controversial topics like the role of contraceptives and the implications of outlawing abortion for rape survivors, all while emphasizing respectful dialogue and the foundational right to life.


