Uncomfortable Conversations with Josh Szeps

Osad

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  Who's hacking you right now? with ethical hacker Assadi Youssef 24.09.2026 1t 22min

  When you read news about a data breach which might have exposed your information, do you even care? Who’s behind all this hacking: China, Russia, or a nerd in his parents’ basement? Are our water and electrical systems at risk? And is A.I. going to make things more secure, or will it destroy privacy altogether? Assadi Youssef got into computer hacking as an eleven-year-old boy before becoming an “ethical hacker”, meaning he’d find vulnerabilities in supposedly impenetrable systems. He’s now an online security genius, advising banks and critical infrastructure companies on how to protect their systems from catastrophic attack. He joins Josh to explore who’s doing all this hacking, whether you need a universal digital I.D, how A.I is changing the game, and whether you really even need two-factor authentication, after all.
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  William Shatner Doesn’t Want to Die, from The Moynihan Report 22.09.2026 54min

  Today we’re sharing a bonus episode from The Moynihan Report. William Shatner sits down with Michael Moynihan in Los Angeles for a conversation about life, time, and knowledge. They talk about death, God, AI, Blue Origin, The Intruder, and the relentless curiosity that keeps Shatner looking for whatever comes next. Oh yeah, and at 95 years old, he’s releasing a heavy metal album.
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  Social media broke our ability to agree with Jonathan Haidt 21.09.2026 58min

  Jonathan Haidt is considered one of the world's most influential living psychologists. He joins Josh on this new instalment of Permission To Think - a collaboration with The University of Technology Sydney School of Social Sciences. This episode is part of The Best Of series and was originally posted on 20th April, 2026. At the time of recording, Jonathan penned a piece for The Atlantic titled ‘Why The Past Ten Years Of American Life Have Been Uniquely Stupid’ that looks at how social media erodes trust, shared narrative and social capital.
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  “So… *Does* God Hate F*gs?” with Megan Phelps-Roper 17.09.2026 19min

  What do our modern-day culture wars have to teach us about cult-like thinking, moral puritanism, judgment and compassion? And if you lose religious faith, how are you left thinking about agnosticism, atheism, the purpose of the cosmos, and the meaning of life? What, if anything, is worth keeping from the Bible? Megan Phelps-Roper was raised in the Westboro Baptist Church, the fundamentalist cult that picketed soldiers’ funerals with placards saying “God Hates Fags”. She appeared in Louis Theroux’s documentary about the church, as its spokesperson and the granddaughter of its founder. Megan left the church, lost her family and her faith. Her TED Talk about polarization was viewed tens of millions of times. She hosted a smash-hit audio documentary series, The Witch Trials of J.K. Rowling, about the moral righteousness on both sides of the transgender debate. Her latest production is Book Keeper, a podcast about returning to the Bible, as an atheist, to figure out what stories are worth keeping. You can listen to Megan’s first appearance on this show here (https://uncomfortableconversations.substack.com/p/the-witch-trials-of-jk-rowling-with). She returns now to discuss atheism, the internal logic of religion, tribal thinking, social media and the way out of our self-certain culture-war bubbles.
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  Is there any Room left for moderates? With Jeff Maurer 14.09.2026 1t 16min

  Is there any room left for the political centre, or has it been swallowed by two competing extremes with nothing but contempt for the middle? Josh chats with comedy writer and author of I Might Be Wrong, Jeff Maurer, for a wide-ranging conversation about the collapse of moderate politics in America. They dig into the strange case of Abdul El-Sayed campaigning with Hasan Piker in the Michigan primary and why that alliance, once worn as a badge of honour, is now something El-Sayed can't stop running from. They also cover Milo Yiannopoulos's deportation, the Democratic Socialists of America's growing foothold in progressive media.
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  JUST JOSH: The Unlearned Lesson of 9/11 10.09.2026 2t 39min

  It's a quarter-century since 9/11. What do we need to understand about its legacy, so as to handle the next quarter-century better? Josh was a college student visiting the World Trade Towers the summer before the September 11th attacks. In this marathon editorial, he reflects on the day itself, the complacency of the 1990s, the "clash of civilisations", popular misconceptions about al Qaeda's motivations, the extraordinary backstory of the Saudi royals and Osama bin Laden, and the moral conundrums of terrorism and war. Lastly, Josh offers the insight you need to take away from September 11th to avoid being blindsided by the civilisational challenges of today.
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  Jewish Comedy at the Bondi Attack 07.09.2026 1t 20min

  Has a secret in your ancestry ever changed who you are? Imagine being a non-Jewish comedian who suddenly finds out he's Jewish. What do you do? You put on a comedy show on the site of the worst antisemitic terrorist attack in the country's history. Of course. David Rose found out his great-grandfather was a famous 19th-century caricature of the stereotypical "Hebrew comic", who performed with the Marx Brothers. Suddenly, David found that audiences expected him to account for Gaza. After the Bondi Beach terrorist attack, the newly Jewish (but still uncircumcised) David Rose staged a show at the Bondi Beach Pavilion entitled "Nepo Great Grandbaby", wrestling with the Jewish sense of humour before Nazism, after Nazism, before Gaza and after Gaza. Fresh from the Edinburgh Fringe Festival, he swung by the Uncomfortable Conversations studios to discuss the craft of comedy, terrorism, trigger warnings, Vaudeville jokes and anti-Jewish sentiment. David's show returns to Sydney and Melbourne next week. Get tickets at https://www.davidrosecomedy.com/
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  Are Men Toxic? 03.09.2026 26min

  A sex scandal involving star players for the Sydney Swans has rocked Australia. Coinciding with a spate of violence against women, the country is revisiting its all-too-familiar conversation about how “Men must do better”. What does that look like, exactly? How do we explain and reduce male misbehaviour against women? Ben Vasiliou is the CEO of Australia's leading preventative mental health charity for teenage boys, The Man Cave. He joins Josh to discuss loneliness, identity, women’s rights activism, male relationships and the influence of the manosphere. Ben’s new book is “Better Man: Reclaiming masculinity for good”.
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  What is Elon Up To?: An Idiot’s Guide to Space and Why You Need to Pay Attention 31.08.2026 1t 53min

  You may not realise it, but humankind is on the cusp of an extraordinary space race. Are we about to become a multi-planetary civilisation? Do we really need a super-fuel-tanker floating in space? Just how many A.I. data centres does Elon want floating high above your head? Anthony Colangelo is a proud space nerd who knows anything and everything about the latest state of play between SpaceX, Blue Origin, NASA and the Mars mission. He hosts two podcasts, Main Engine Cut Off and Off-Nominal, and he joins Josh for brain-tickling banter about why the space shuttle sucked, why satellite communication constellations like Starlink will become indispensable, and everything you need to know about the unfolding revolution in humanity’s adventures off the face of this planet.
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  Glenn Loury: Are we censoring ourselves to death? 27.08.2026 26min

  In this recording of a live event at the Festival of Dangerous Ideas, Josh hosts a one-on-one conversation with the legendary American intellectual, Glenn Loury. Loury is one of America's most influential thinkers about self-censorship, cancel culture, race relations and polarisation. As a Reagan conservative in the 1980s, he was a controversial dissenter from mainstream Black thought... but a hero to the likes of Supreme Court Justices Antonin Scalia and Clarence Thomas. Loury argues that self-censorship isn’t just a personal failure of nerve, but a social epidemic. Every society enforces norms. But have we become so intolerant of dissent that we’ve stopped being able to think freely in public? This episode is a one-of-a-kind opportunity to listen in to a sold-out event. Our thanks to the Festival of Dangerous Ideas for bringing Glenn to Sydney for this special Uncomfortable Conversations collaboration.
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  Jason Arday, Suey Park & the Identity Hunger Games 24.08.2026 30min

  Josh has been reflecting on what the tragedy of Cambridge University's youngest-ever Black professor reveals about the high-stakes identity game we've all been enlisted into. In this solo episode, he issues a call to arms to defy the whole sanctimonious circus and assert your own glorious human messiness. Be real, humans.
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  How the Public Shaming Machine was Built with Jon Ronson 20.08.2026 22min

  What should we make of the public shaming machine we have built? Following the death of the Cambridge academic Jason Arday, Josh checks in with the godfather of public shaming, Jon Ronson. His 2015 book So You’ve Been Publicly Shamed was the first blockbuster analysis of what we now call “cancel culture”, and even inspired an episode of Black Mirror. Ronson was Louis Theroux before Louis Theroux. His BBC podcast, Things Fell Apart, is about the culture wars. He’s a contributor to This American Life, the New York Times Magazine, GQ and The Guardian UK. His TED Talk, Strange answers to the Psychopath Test, has nearly 60 million views. Jon joins Josh to to revisit his ideas about cancel culture; how the “shaming machine” has been weaponised; the new identitarian “woke right”... and to discuss the best sightseeing spots in Sydney. His new book is The Castle, and he’ll be touring the UK & Australia later this year.
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  The Case Against Israel with Peter Beinart 17.08.2026 1t 35min

  Peter Beinart is arguably the world’s most influential Jewish anti-Zionist.  He’s a journalist and a professor of journalism and political science. But in American and Jewish cultural life, he’s far more than that -- a lightning rod, a traitor, a truth-speaker, a coward, a hero. Applauded, derided, beloved, loathed.   Peter is an orthodox New York Jew who keeps kosher, attends synagogue, and sends his kids to Jewish schools. He was originally a pro-Iraq-War liberal hawk, who wrote muscular books like “The Good Fight: Why Liberals—and Only Liberals—Can Win the War on Terror”. His worldview changed, especially regarding Israel, after numerous visits to the West Bank. He no longer argues for a two-state solution but for a single state between the river and the sea in which Jews and Palestinians live as equals. Is that pie-in-the-sky, or the only way out for Jews and Palestinians alike? Peter’s latest book is “Being Jewish After the Destruction of Gaza”. Peter has written for Time, The Atlantic, The New York Review of Books and is a contributing opinion columnist at The New York Times. On the eve of his trip to Australia to appear at the Festival of Dangerous Ideas (where Josh will appear in conversation with Glenn Loury - stay tuned for that), Peter joins Josh to wrestle with Zionism, anti-Zionism, Palestinianism, Gaza, ethnic supremacy, and the future of the Jewish people.
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  How Branding Replaced Facts in Politics 13.08.2026 16min

  What unites Trump and Obama, Pepsi and Coca-Cola, the far right and the far left? They’re all brilliant at defining their brands. They have a clear narrative. They can tell a compelling story about the world and their place in it. So much of life, of business, of social media, of political parties and social movements is shaped, these days, not by facts but by “alternative facts”, by feelings, by storylines. You, yourself, may even have a personal brand: the disrupter, the carer, the loyalist, the contrarian, the lover. Matt Jones was a political strategist and speechwriter for the British Conservative party in the early 2000s. He went on to deploy his brand expertise in the private sector, where he co-created a small gin company which was sold for a fortune less than a decade later on the strength of its brand reputation. Matt joins Josh to explore how storytelling is shaping your life more than you realise, from the supermarket to the ballot box, and how we might bring sanity back to public life. Matt’s new podcast is StoryWork.
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  How to be a Dissident 10.08.2026 1t 14min

  What does it mean to be a dissident? If you join a protest march, are you dissenting… or conforming? How should you push back against leaders who wield fear and intimidation; against digital technology that dehumanises you and flattens us all? Gal Beckerman is a staff writer at The Atlantic who worked for six years at the New York Times Book Review. His first book was named a best book of the year by The New Yorker and The Washington Post, and his latest is How to Be a Dissident, a guide to living with integrity in an age of conformity and authoritarian drift. Gal joins Josh to discuss ICE agents, Jimmy Kimmel, Putin’s dissidents, Jews defending Gaza, communist Czechoslovakia, the quiet, task-by-task incursion of algorithmic media into your life… and what the most courageous dissidents reveal about how to find your moral compass in a dizzying age.
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  Are Jews Okay? (with baklava) 06.08.2026 17min

  Is Israel making Jews safer, or less safe? Does pro-Palestinian activism feed antisemitism, or is that a Zionist lie? And why are Greek men so hunky? Two of Josh’s favourite gals, ChayaLeah and Yael from the “Ask a Jew” podcast, join Josh from California and Greece for a funny but forthright catch-up about freedom, terrorism, Palestine and felafel. Enjoy.
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  Josh vs the News: Why Everyone is Wrong About A.I. 05.08.2026 48min

  Fable this. Deepseek that. As fascinating as each new A.I. model breakthrough (or breakout) is, are we missing the forest for the trees? The Reverend Josh believes so. In this scintillating Substack Livestream, he leads us to the Promised Land the way all great Messiahs do: with a four-point bureaucratic plan. Along the way, he’ll answer your questions about Israel, sun protection, and how much he can bench.
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  Why is Trump Building a Secret Ballroom Bunker? 03.08.2026 1t 32min

  Exploding pagers! Enigma codes! Sexy Israeli spies! J Edgar Hoover's boyfriend's remote-controlled window opener! And, yes, Trump's top-secret ballroom bunker. It's all told with impeccable style by Matt Bevan, the host of If You're Listening, which is one of Josh’s favourite shows about international intrigue. The show's companion book, If You're Listening: Declassified, explores how history is a patchwork of conflicting accounts, misremembered details and outright myths. Matt regales Josh with the most amazing anecdotes of espionage... and to explain what Hezbollah's exploding pagers have in common with the bunker which Dick Cheney hid in on 9/11. Help us improve the show! Share your thoughts and have your say, take the Uncomfortable Conversations Audience Survey: https://uncomfortableconversations.substack.com/p/have-your-say-to-shape-the-show
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  Buckle Up for “the Manosphere 2.0” - Helen Lewis 30.07.2026 18min

  What’s up with boys? Or, more importantly, what’s up with the men who use “what’s up with boys?” to crush women? It’s not just a rag-tag fringe of young male influencers who are reviving sexism. There’s a professional movement of influential Christian nationalists whose long-term agenda is to return women to their rightful place, as homebound subjects of their husbands. Helen Lewis’ reporting on gender, politics, and internet culture has made her one of the sharpest voices on the culture wars. She became a viral sensation when she bested Jordan Peterson in a 2018 debate about gender roles for British GQ. She’s now a staff writer at The Atlantic, where her recent cover feature was “The New Gender War”. Helen and Josh unpack the evolving backlash to feminism and liberalism, the furore around surrogacy and transgender rights, Andrew Tate… and what the World Cup had to do with all of it.
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  Josh vs the News: How The Odyssey Broke the Internet 27.07.2026 32min

  The way culture-war ideologues have hijacked The Odyssey reveals how social media ruins everything. As go the arguments about the film, so go our conversations about fairness, gender, race and immigration. And so go our elections. Josh recounts the online sh**storm, and draws a long bow from Homer to Christopher Nolan to how civilisations like ours collapse. Read Josh’s column in the Australian Financial Review here: https://www.afr.com/politics/federal/culture-war-ideologues-have-hijacked-christopher-nolan-s-odyssey-20260720-p60gpr and David French’s NYT column here: https://www.nytimes.com/2026/07/26/opinion/odyssey-christopher-nolan-greek-gods.html Oh, and go back and watch “Just Josh: The Woke Catastrophe of Snow White” here: https://uncomfortableconversations.substack.com/p/just-josh-the-woke-catastrophe-of?utm_source=publication-search