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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

68:45

SZEPS WORLD TOUR - NICK CAVE on Faith, Melancholy, &...

Uncomfortable Conversations with Josh Szeps ·

2025/08/25

Nick Cave is one of Australia’s biggest musical exports. But after forty years as a rockstar - and the death of two sons - he's become something else: A unofficial poet laureate and philosopher king through his online letters project, The Red Hand files. Nick sat down with Josh in London on the Szeps Live World Tour to discuss songwriting, grief, faith... and, as a bonus, to critique some of Josh's recent episodes.

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39:37

SZEPS WORLD TOUR - JIMMY CARR, COMEDY LEGEND

Uncomfortable Conversations with Josh Szeps ·

2025/08/21

Jimmy Carr is one of the most successful stand-up comics on earth. His hilarious, brutal crowd work is a viral sensation. His Netflix specials are smash hits. He hosts huge UK television panel shows and is currently touring the US, UK & Europe (and Australia and New Zealand early next year) with his latest live show, JIMMY CARR: LAUGHS FUNNY. Jimmy and Josh caught up in-the-flesh in London on the Szeps Live Around-the-World Podcast Marathon to discuss crowd work, Elon Musk, immigration, COVID,

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87:28

SZEPS WORLD TOUR – COLEMAN HUGHES on Race, Trump & Power

Uncomfortable Conversations with Josh Szeps ·

2025/08/18

He’s been grilled before Congress, clashed with Bill Maher, and built a reputation as one of the most interesting young intellectuals in America. Coleman Hughes doesn’t just write and broadcast, he also plays a mean jazz trombone, bringing the same contrarian rhythm to politics as he does to music. During the Szeps Live World Tour’s jaunt through New York, Josh and Coleman sat down to dive into race, identity, Trumpism, and whether the Left can find its groove again.

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39:15

SZEPS WORLD TOUR – MEGHAN DAUM on What You’re Not...

Uncomfortable Conversations with Josh Szeps ·

2025/08/14

As the Szeps Live Around-the-World Podcast Marathon barrels along, Josh and his long-suffering producer, Jono, cruise their rented convertible into the hills of Northeast Los Angeles. There, they track down the ultimate iconoclast, Meghan Daum - former Los Angeles Times columnist, humorist, defender of sanity and all-round cultural firebrand. Meghan's independent media empire is The Unspeakeasy - a podcast, Substack publication and a community for freethinking women. Enjoy this sparkling ramble

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80:40

SZEPS WORLD TOUR - RICH ROLL on Liberty, Loneliness &...

Uncomfortable Conversations with Josh Szeps ·

2025/08/11

Rich Roll is one of the biggest podcasters in America, thanks to his irresistible blend of ultra-athleticism, Stoic philosophy, sobriety, personal improvement (don't call it "self-help"), and an infectious curiosity about what makes life worth living. In this live-streamed conversation on the Szeps Live World Tour, Rich welcomed Josh to his new digs in a glorious mountaintop lair behind Malibu - to to talk discipline, midlife pivots, the seductions of modern distraction, and whether resilience today

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84:14

SZEPS WORLD TOUR - KMELE FOSTER on Race, Spirituality...

Uncomfortable Conversations with Josh Szeps ·

2025/08/08

What is your race? What is your identity? How should your kids think about how they fit in at school, or don't, on the basis of their racial or economic group? What is it really about, this game of being human? Kmele Foster is one of the most original and humane thinkers Josh has the privilege of knowing. Funny, fearless and wise, the two young dads sat down in Brooklyn during the Szeps Live Around-the-World Podcast Marathon to wrestle with Blackness, whiteness, racism, parenting, guilt-ridden woke

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68:16

SZEPS WORLD TOUR - SAM HARRIS on Making Sense of Life

Uncomfortable Conversations with Josh Szeps ·

2025/08/05

How much responsibility do podcasters have not to "platform" crazy voices? Is there a countervailing duty to explore unusual ideas, spurned by elites? Why did Sam Harris fearlessly take on Islam, Black Lives Matter and Gaza, but not transgender ideology? Are psychedelics a portal to another realm, will A.I. become conscious, and is Sam a hypocrite for eating meat? Sam Harris is one of the world's most influential podcasters and commentators. He burst onto the scene as a prominent atheist but has

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38:32

On Stage in NYC: Panel Show at the Comedy Cellar

Uncomfortable Conversations with Josh Szeps ·

2025/07/31

It was a sweltering evening in Greenwich Village as a packed crowd showed up at the legendary Comedy Cellar - the stomping ground of Seinfeld, Chappelle, and Robin Williams - for a no-holds-barred, live-streamed panel extravaganza. Is South Park doing more to resist Trump than the press, or is it part of the circus? What happens when podcasting becomes the default news source? Is "platforming" bad ideas dangerous or essential? Are we nostalgic for a media era that never was? And how do you choose

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83:11

SZEPS LIVE TOUR: "Inequality, Abundance, & Using A.I....

Uncomfortable Conversations with Josh Szeps ·

2025/07/29

Tyler Cowen is one of the world's Top 100 Global Thinkers according to Foreign Policy magazine. The Wall Street Journal calls his blog, Marginal Revolution, the world's best economics blog. His day job is as an economics professor at George Mason University, where he also runs the classical liberal Mercatus Center. But his influence is immense... on policymakers, tech titans and thought leaders who hang on his ideas as a visionary sage. Tyler hosts what Josh regards as one of the world's best

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40:03

SZEPS LIVE TOUR: "Atheism, Wokeness & Islam" with...

Uncomfortable Conversations with Josh Szeps ·

2025/07/27

Born in Pakistan, Sarah Haider founded the Ex-Muslims of North America to help Muslims escape Islamist coercion. She was an outspoken atheist. Then... she lost her faith in atheism.First, she noticed progressive peers preaching critical race and gender ideologies, while punishing blasphemers of their social-justice dogmas in ways that felt uncomfortably... religious. Second, she tripped out on Ayahuasca. Third, she walked away from her podcast, A Special Place in Hell. What happened? Sarah sat down

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71:53

THE SZEPS LIVE WORLD TOUR IS UNDERWAY

Uncomfortable Conversations with Josh Szeps ·

2025/07/26

G'day from New York City. We've been sitting on this Easter egg for some time, warming it up under our feathery little tooshes. It's now time to let the warm yolk of intellectual invigoration ooze over your grateful noggins. It's time for theSZEPS LIVE WORLD TOUR. Yes, global mega-giant publishing behemoth Substack has tapped this li'l ole show for Substack's first-ever Live-Streamed Around-the-World Podcast Marathon. That's a LOT of hyphens. Six cities. Twelve days. Twenty-four time zones. No

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67:57

"How Not to Feel Like a Failure (When Fame & Fortune...

Uncomfortable Conversations with Josh Szeps ·

2025/07/21

How do you avoid the hamster wheel of hoping that your next success will deliver happiness? How do you escape mental ruts, anxious spirals and critical self-talk? Osher is a superstar in Australia. He was the face of Australian Idol, The Masked Singer, The Bachelor and The Bachelorette. He also happens to have, as he politely calls it, "a different brain" -- a brain prone to depression, social anxiety, obsessive compulsion, psychosis and addiction. His podcast, Better Than Yesterday, discusses

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57:16

PREMIUM: "How to Raise an Awesome Kid (and be an...

Uncomfortable Conversations with Josh Szeps ·

2025/07/17

It's one of the most persistent, perplexing and provocative questions to plague our culture: What explains the explosion in ADHD, anxiety and autism in kids? Is it too much Instagram? Not enough Ritalin? Or are one-of-a-kind kids being failed by a one-size-fits-all model of schooling and parenting? Dr Billy Garvey is one of Australia's leading developmental paediatricians. He's a senior specialist at one of Australia's largest university paediatric hospitals, where he works with kids struggling with

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97:43

"The Case for Nuclear Power" with Aidan Morrison

Uncomfortable Conversations with Josh Szeps ·

2025/07/14

Have rich democracies been hoodwinked into chasing a mirage of green energy? Are renewables leading us into a dead-end of brown-outs, white-elephant wind farms, and costly, dodgy electricity? Are the "smart homes" and "smart grids" actually overly-complicated patchwork solutions to a problem that has a safe, affordable, reliable, carbon-free solution - nuclear? And what the hell is "baseload" power, anyway? Aidan Morrison is the Director of Energy Research at the classical-liberal Centre for

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32:50

PREMIUM: "In-Groups & Out-Groups" with social...

Uncomfortable Conversations with Josh Szeps ·

2025/07/10

Are you defined by your identities? Where do you rank in the hierarchy of your social group, either online or in real life? How are the boundaries of your communities policed? By whom? In an era of social-media mobs, splintering communities and anti-immigrant ideas, the way we sort ourselves into in-groups and out-groups is a fascinating field of social psycology. Professor Jetten is an expert in the psychology of inclusion and exclusion, radicalisation, social dynamics, and the ways in which

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123:35

“Josh vs the Anti-Gay-Parenting Activist” Katy Faust

Uncomfortable Conversations with Josh Szeps ·

2025/07/07

Katy Faust is a family-values activist who campaigns against all families that don't contain a biological mother and father. A rockstar among American conservatives, she's the founder of the children's rights organization, Them Before Us. On shows like Jordan Peterson's - and in her lobbying of lawmakers - she argues for prioritising every baby's right to its biological parents over the right of adults to start a family. At a time when Republican support for same-sex marriage is dropping fast thanks

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50:39

"Artificial Intelligence in a Human World" with Prof....

Uncomfortable Conversations with Josh Szeps ·

2025/07/03

Is it legit for tech companies to vacuum up everything humans create, to spin off A.I. content, and not to compensate humans? Will this world of creative artificial creatures promote or corrode human creativity? In America, two tech giants just won landmark court cases over their use of copyrighted works to train A.I. models. The court found that Meta and Anthropic didn't violate copyright when they trained their large language models on books without the authors' permission. This raises big

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65:56

"Should We Ban Extreme Wealth?” with Prof. Carl Rhodes

Uncomfortable Conversations with Josh Szeps ·

2025/06/30

Is there something broken about a world where some people are absurdly, insanely rich? Or is inequality the price we pay for innovation? What do Bezos, Gates, Musk & Zuck tell us about what's malfunctioning in our societies? Would be better with no billionaires, or is the anti-rich movement an impoverished politics of envy? Professor Carl Rhodes was the dean of the business school at the University of Technology, Sydney. His new book is "Stinking Rich: The Four Myths of the Good Billionaire"

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50:43

PREMIUM: “The Palestinian Delusion: the 'Right of...

Uncomfortable Conversations with Josh Szeps ·

2025/06/26

What if the problem for the Palestinian people was not Israel, but the encouragement by the international community of a fantasy that, one day, Palestinians will return to Israel proper? That’s the thesis of 'The War of Return’ by former Labor parliamentarian and foreign policy advisor to Prime Minister Shimon Peres, Einat Wilf. She opposes settlement-building but is otherwise a left-wing hawk. Wilf argues that the main reason why the conflict endures - and why Palestinians remain

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64:16

"A.I., Artificial Souls, and the Crazy Conundrum of...

Uncomfortable Conversations with Josh Szeps ·

2025/06/23

Let's take a break from the news cycle for a moment, shall we? There's a lot of cool shit to ponder that's more important and more fascinating. Like, how does the gooey blob of atoms between your ears generate all of your experiences? And are we on track to producing machines that feel as alive as you? Eric Schwitzgebel is a legendary professor of philosophy at UC Berkeley and an important voice in Silicon Valley's conversations about ethical artificial sentience. He and Josh muse on the various

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