Is there any Room left for moderates? With Jeff Maurer

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.

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.

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.

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.

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.

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.

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/

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”.

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.

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.