PodcastsComedyUncomfortable Conversations with Josh Szeps

Uncomfortable Conversations with Josh Szeps

Josh Szeps
Uncomfortable Conversations with Josh Szeps
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440 episodes

  • Uncomfortable Conversations with Josh Szeps

    Nazi Jokes & Stand-Up Taboos with Tom Ballard

    2026/04/01 | 1h 19 mins.
    Think of Tom Ballard as a young John Oliver, who hosted Australia's national nightly satirical news television show ,"Tonightly with Tom Ballard".

    He returns to the show to discuss his getting cancelled for doing a Nazi salute, punching down, anti-semitism, Gaza & Zionism, cancel culture and offensive comedy.

    This episode is part of the Uncomfortable Conversations Comedy Festival extravaganza. Josh headed to Melbourne for a ten-hour Substack Live marathon with five of the greatest comedians. You'll get a new episode every 48 hours for the first two weeks of the biggest comedy festival in the world.

    Ballard's stand-up show is ‘Be Funny Challenge (Impossible)’ and his play about stand-up and cancel culture is ‘JKS: a Comedy(?)’

    Tickets at comedyfestival.com.au
  • Uncomfortable Conversations with Josh Szeps

    Manosphere, Feminazis & the "Six Tribes" of Young People

    2026/03/30 | 1h 24 mins.
    Across the West, young people are finding it harder to build their careers, afford homes, and start families. But have we assumed they’re all the same, and been so busy treating the symptoms of their unhappiness that we've accidentally made them more miserable?

    A major new study has divided young Australians into six "tribes": from far-left student activists to family-oriented nationalists, from pragmatic strivers to the affluent and already comfortable. They have almost nothing in common politically, but they all want the same things: financial security, home ownership, meaningful work, a family.

    The difference between them isn't money or politics, but whether they believe the barriers in their way are within their control.

    Parnell Palme McGuinness is a columnist at the Sydney Morning Herald and a senior fellow at the Centre for Independent Studies. She’s previously worked for the Australian Liberals, our conservative centre-right party, and the German Greens.

    She joins Josh to explain the six tribes she identifies in her report, ‘Generation Trapped: Housing, handouts, and the collapse of young Australians’ life satisfaction’, and why understanding them is key to resolving the tensions simmering across the West, from intergenerational equity and immigration to the rise of populism.
  • Uncomfortable Conversations with Josh Szeps

    Everything is Awesome! Just Ask Josh

    2026/03/26 | 32 mins.
    Everything is awesome humans. Well at least it is when Uncomfortable Conversations Community Manager (and resident Tocqueville expert) Evan Pivonka joins us.

    Josh and Evan went live to answer your questions and explore some underreported stories: Ozempic zombies, insider trading allegations, humans about to return to the moon, and the lost art of talking to strangers.
  • Uncomfortable Conversations with Josh Szeps

    Top Trump Diplomat Tells All: fmr Deputy Secretary of State Inside the Room Where it Happens

    2026/03/24 | 1h 6 mins.
    What is going on with Trump’s foreign policy? Attacking Iran, decapitating Venezuela, threatening Cuba. Is America flexing its greatness, or flailing? Is there a method to the madness? What is really going on inside the room where it happens?

    Stephen Biegun was the United States Deputy Secretary of State in the first Trump Administration. He was also the special representative for North Korea, charged with overseeing America’s North Korea policy and running the first ever in-person negotiations between the two country’s leaders. While Trump was tweeting about “Rocket Man”, Biegun was trying to make history.

    What was it like to work with Trump on complex foreign policy negotiations? What happened on last-minute sorties across the DMZ with the leader of the free world? And what has Stephen’s experience in seeing Trump’s worldview, first hand, taught him about strategy, Putin, Ukraine, and Iran?

    Biegun worked in the George W. Bush administration as a member of the National Security Council under Condoleezza Rice and was a senior executive at the Ford Motor Compnay. He joined Josh on a visit to Sydney to deliver a major lecture at the Lowy Institute, which kindly facilitated this conversation about American power, diplomacy, war, and the Trump you don’t see behind the scenes.
  • Uncomfortable Conversations with Josh Szeps

    "Mr Mamdani, THIS is What Makes a City Thrive" with Eamon Waterford

    2026/03/20 | 50 mins.
    Cities that rock and cities that suck do a few things differently. They need to hit a bullseye on high-vs-low density, walkability, law and order, red tape, congestion pricing and a host of other things. Which cities nail it? And how can yours do better?

    Eamon Waterford is a world expert on what the best cities get right. He's the chief executive of a think tank, the Committee for Sydney, that represents the interests of all the big players in Sydney’s economy: not just property developers but local councils, banks, architects, consultants, law firms, universities. He assesses how cities all over the world can evolve into the best version of themselves.

    Eamon joined Josh to riff on Mamdani, New York, Tokyo, Singapore, Paris, Los Angeles; on the tension between low-density suburbs and walkability; between infrastructure and green spaces; between untrammelled development and too much risk aversion. If you want to live in the city of your dreams, listen up.

    Go to https://surfshark.com/joshs or use code JOSHS at checkout to get 4 extra months of Surfshark VPN!

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About 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  
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