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PODCAST

Uncomfortable Conversations with Josh Szeps

The world has never been more connected. Yet never more divided. We yell at each other from inside our echo chambers. But change doesn’t happen inside an echo chamber. It’s time to get out, to stretch our legs, to step on some land mines. It"s time to have an uncomfortable conversation with Josh Szeps. A DM Podcast

society & culture comedy interviews

All Episodes

104:24

“Conspiracies, Echo Chambers & Culture Wars” with...

Uncomfortable Conversations with Josh Szeps ·

2025/05/05

The internet is a dumpster fire. Are you a firefighter? Or an arsonist? This episode is a cracker. Sacha Judd is an expert on internet subcultures. A former lawyer, she has become something like “the Mark Cuban of New Zealand” - a smart, left-wing investor in high-growth startups; advisor to businesses; and fierce commentator on Big Tech. Sacha wants to bring back the “good internet”: a place fueled by genuine community, creativity, and connection. She and Josh wrestle with

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50:27

PREVIEW: Nobel Peace Prize Winner Dave Sweeney

Uncomfortable Conversations with Josh Szeps ·

2025/05/02

Do nuclear weapons protect Western civilisation? Or are they an insane error that humanity should undo? Is nuclear power worth the cost and risk? Dave Sweeney co-founded the International Campaign to Abolish Nuclear Weapons (ICAN), which won the Nobel Peace Prize in 2017. Dave and Josh debate the risks and rewards of nuclear weapons and nuclear power in an unstable world, and discuss whether environmentalism is antithetical to progress. To hear every bit of this fascinating, two-hour-plus

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71:54

BONUS: "Indigenous Land Acknowledgement Furore" with...

Uncomfortable Conversations with Josh Szeps ·

2025/05/01

Have indigenous Welcomes-to-Country gone too far? On Friday, far-right hecklers disrupted the Welcome to Country (i.e. the land acknowledgment, in North American parlance) of a profound Australian national event, the Anzac Day Dawn Service. The protest has sparked a national firestorm about race, racism and remembrance. Josh shares his thoughts about the coverage of the controversy, and then debates its deeper implications with the Indigenous scholar Tyson Yunkaporta. Watch this conversation on

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73:36

"Facebook Whistleblower" Frances Haugen

Uncomfortable Conversations with Josh Szeps ·

2025/04/28

What’s social media doing to us, and how would you fix it? Mark Zuckerberg has been a busy boy on the witness stand in Washington DC lately. In one of the most consequential antitrust cases in tech history, Meta is being sued by the U.S. government for allegedly maintaining a monopoly. It could reshape the future of social media, privacy regulation, and Big Tech. But in an ideal world, how would you reform social media? How might we prevent it from deranging us? Frances Haugen worked at Google

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84:55

"American Authoritarianism" with Matt Welch

Uncomfortable Conversations with Josh Szeps ·

2025/04/24

What do you make of a U.S. government that snatches people off the street and disappears them into Central American prisons, forever, with no trial, and no way to appeal? Matt Welch is a libertarian journalist. He's no wild-eyed, Trump-loathing leftie. Fresh off the back of his appearance on Bill Maher, Matt joined Josh on Josh's streaming TV show, Szeps Live, to riff about Elon, DOGE, government effectiveness, abundance liberalism, high-speed rail, Orbán, Erdoğan, el Salvador, the Supreme

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108:09

“Reimagining Schooling” with Finnish education icon...

Uncomfortable Conversations with Josh Szeps ·

2025/04/21

What's the purpose of school? Why do we run schools the way we do? How might we reinvent education in an era of artificial intelligence and ADHD? Professor Pasi Sahlberg is one of the world's leading education experts. He ran Finland’s Ministry of Education and Culture, moved to Washington DC to advise the World Bank on education, and was a visiting professor at Harvard University. His award-winning book is "Finnish Lessons: What can the world learn from educational change in Finland?" Pasi is

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20:23

PREVIEW: "What Can Democrats Do?" with David Pakman

Uncomfortable Conversations with Josh Szeps ·

2025/04/17

The Democratic Party is paralysed. It can't merely offer resistance to Trump. It also needs to offer an alternative to him. But how? Should they oppose his every move, as the likes of Representative Alexandria Ocasio-Cortez and Senator Cory Booker believe? Or should they shut up and wait for the president to doom himself, as Senate minority leader Chuck Schumer and former Clinton consultant James Carville prefer? How have Democrats fallen... and what can they do now? David Pakman is the guy Josh

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78:53

“Decoding the Gurus” with Chris Kavanagh and Matt Browne

Uncomfortable Conversations with Josh Szeps ·

2025/04/14

When are independent shows like Uncomfortable Conversations serving a useful purpose... and when are they just preaching to the choir? "Decoding the Gurus" is a podcast that dissects how new-media personalities gain guru status. Frequently, such podcasters claim to be bravely challenging the status quo... while comfortably pandering to their team. Is Josh such a hack? Josh is in Tokyo visiting one of the Decoding hosts, Chris, who lives there. The three of them caught up to record this crossover

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71:24

Anthony Bourdain’s “Lieutenant”, Laurie Woolever

Uncomfortable Conversations with Josh Szeps ·

2025/04/10

Anthony Bourdain was Josh's hero. Laurie Woolever was, as Bourdain called her, his "lieutenant". A writer and culinary graduate, Laurie had worked for another gigantic cooking celebrity, Mario Batali, before he was brought down for alleged sexual harrassment. She spent almost ten years as Bourdain's right-hand-gal. The two of them wrote two books together, one of which they were halfway through when Bourdain died by suicide in 2018. Laurie posthumously published "Bourdain: The Definitive Oral

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38:46

PREVIEW: "What Is the 'Patriarchy'?" with Prof....

Uncomfortable Conversations with Josh Szeps ·

2025/04/07

Do males and females differ in what we want out of life? In what jobs we want to do? In how much we want to look after babies, or run a tech start-up, or sweep the living room, or be a CEO? Or are biological preferences just an excuse to justify inequality? Cordelia Fine is a feminist academic who studies scientific explanations of sex differences and workplace inequality. Her books on gender have won prizes at the Royal Society, been recommended by the Sunday Times, and cited as among the Top Ten

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28:49

JUST JOSH: The Woke Catastrophe of “Snow White”

Uncomfortable Conversations with Josh Szeps ·

2025/04/03

If you want to see what's wrong with not being offensive, watch Snow White. The new Disney re-make is so committed to not offending anyone that it’s a social-justice jumble. Snow White isn’t white as snow; her love interest isn’t a prince; the dwarves aren’t “dwarves”; but there IS a dwarf in a non-dwarf role; Snow White doesn’t need a man; the man doesn’t “stalk” her; she’s a bad-ass independent gal; the word “dwarf”

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100:32

BOB CARR on Diplomacy, Statesmanship and Grief

Uncomfortable Conversations with Josh Szeps ·

2025/03/31

Even if you're not Australian, you want to listen to this conversation with one of the nation's most iconic statesmen. Bob Carr is a former foreign minister of Australia (i.e. the secretary of state) and, before that, the longest-continuously-serving Premier of NSW, Australia's most populous state. He's an intellectual powerhouse, an icolonoclast, a champion debater, a student of American history, of geopolitics and of diplomacy. For the first portion of this conversation, he and Josh discuss

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38:43

PREMIUM: “Does Ukraine Still Matter?" with...

Uncomfortable Conversations with Josh Szeps ·

2025/03/27

What are Trump and Putin cooking up for Ukraine? Can the Europeans sideline it? What options does Ukraine still have on the table? And does any of this really matter to non-Europeans any more? This week, the ceasefire talks that President Trump boasted he'd wrap up in 24 hours fell apart, again. Russia says it wants an end to the war, if Ukraine effectively surrenders. Trump now admits Putin might be "dragging his feet". Misha Zelinsky lived in Ukraine for the first year of the war, reporting from

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66:30

Australia’s Shadow Treasurer, Angus Taylor

Uncomfortable Conversations with Josh Szeps ·

2025/03/24

Angus Taylor is the Shadow Treasurer of Australia and a key figure of the Opposition, the centre-right Liberal Party. A former cabinet minister, businessman and Rhodes scholar, he's often discussed as a future prime minister. Opinion polls put his party's return to power in the May election as a 50/50 bet. Josh sat down with the Shadow Treasurer to discuss innovation, productivity, nuclear power, and how annoying it is to do your taxes. Watch this conversation on YouTube. And you’re missing

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40:50

PREMIUM: "Two Jews Debate Israel" with Antony...

Uncomfortable Conversations with Josh Szeps ·

2025/03/20

How should moderate, secular Jews feel about Israel? How brutalising must Israel’s Gaza policy be before more Jews denounce it? Is Israel a well-intentioned country hijacked by right-wing leaders from its true purpose of peace? Or is it intrinsically committed to destroying Palestinians? Was a Jewish ethno-state a mistake from the start? Or is Israel an island of democracy in a sea of Islamist dysfunction? No group debates these questions more vehemently than Jews themselves. After the

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85:46

JOHN McWHORTER: Language, Race & Trump

Uncomfortable Conversations with Josh Szeps ·

2025/03/17

John McWhorter is arguably the world’s most famous linguist. A professor at Columbia University and a columnist for the New York Times, he alternately enrages the right and the left as an anti-Trump, anti-woke, Black academic. John and Josh sat down in Sydney to discuss gay slang, the Trumpist right, Black provocateurs and “serving c***t”. Watch this conversation on YouTube. And you’re missing out on our best ad-free content if you haven’t popped over to the Uncomfy

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42:01

"Why Greenland Matters" with Sherri Goodman

Uncomfortable Conversations with Josh Szeps ·

2025/03/13

When Trump floated the idea of the U.S. acquiring Greenland, some called it a random brain fart. But there is a real conversation among security experts about control of the Arctic in the 21st century. As climate change opens up new avenues for shipping, spying, mining, submarining and warfare, the far North Atlantic matters more and more. Sherri Goodman was the Pentagon's chief environmental officer in the Clinton Administration. Her specific expertise is in the polar regions, Russian nuclear subs,

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81:10

BONUS: Josh on Israel-Palestine Coverage

Uncomfortable Conversations with Josh Szeps ·

2025/03/12

Last week,Arab leaders gathered in Egypt for a Palestine Summit. The 22-nation Arab League emerged with a re-energised Arab Peace Initiative to solve the Israel-Palestinian Conflict once and for all. Australia's largest and most trusted news organisation, the ABC, covered the event in an article entitled "This Plan Would End the Israel-Palestinian Conflict, But Israel Doesn't Like It". Josh has thoughts. This is a recording of an episode of Szeps Live, a weekly Substack Video Livestream. Most

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59:18

"Trump, Gaza & Liberalism" with Senator Dave Sharma

Uncomfortable Conversations with Josh Szeps ·

2025/03/10

Australians go to the polls in a few months. It looks surprisingly grim for the first-term, centre-left Labor government of Prime Minister Anthony Albanese. As part of Uncomfortable Conversations' election coverage, Josh invited a select handful of prominent politicians who are likely to be the most interesting figures for listeners from all over the world to enjoy. Senator Dave Sharma is one of them. He's a member of the Opposition centre-right Liberal Party. He was a member of the Australian House

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73:45

"The Next Canadian PM” with Jen Gerson

Uncomfortable Conversations with Josh Szeps ·

2025/03/06

Justin Trudeau's political career will end this weekend when his replacement is elected as the Canadian Liberal leader. This happens at a moment of extraordinary uncertainty for Canadians. As the U.S. launches a painful trade war, Canadians are being forced to rethink their economic and strategic future. What's going on up there? Who are the candidates you need to know? How do they perceive the Trump tariffs? Jen Gerson is a writer who worked for the Economist, Toronto Star and The Globe and Mail

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