Uncomfortable Conversations with Josh Szeps

Zainab Johnson is a black muslim female New Yorker with a half-million instagram fans and the title of Variety magazine’s Top 10 Comics to Watch.

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.

Zainab joined Josh to school him on comedy, Islam, and marsupial reproductive biology.

Her Amazon Prime special is ‘Hijabs Off’

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

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.

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.

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.

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.

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Step away from the doomscrolling. Take a breath. Let the waves crash.

In this week's edition of Josh vs the News, Josh offers something different: a tonic for tumultuous times. Instead of dissecting the latest outrage or geopolitical crisis, he invites you to zoom out and remember what actually matters.

How do you find peace when artificial intelligence threatens widespread, fast, and traumatizing change across every sector of society? When the news cycle never stops? When even our political tribes have become echo chambers of certainty?

Consider this your permission to touch grass, smell the roses, and remember that the waves of the South Pacific will keep crashing long after today's outrage has faded.

How can a bunch of equations on a piece of paper reflect the deepest facts about reality? How is it that every single object, from a skyscraper to a black hole to your liver, obeys mathematical gobbledegook? And how do physicists deduce that gobbledegook just by solving written puzzles?

Today's episode will blow your mind with curiosities about the fabric of reality, the size of the biggest numbers, and how a simple probability problem, posed by a popular television game show, the Monty Hall Show, captivated America for years.

Adam Spencer is a former radio host, keynote speaker and the University of Sydney's ambassador for mathematics and science. His TED Talk was "Why I fell in love with monster prime numbers" and he has a new Substack, NerdNews by @adambspencer.

References from Adam:

• John Searle’s article “Consciousness” (published in Annual Review of Neuroscience)
• “Biological naturalism”
• Anil K. Seth, “Conscious artificial intelligence and biological naturalism,” Behavioral and Brain Sciences (2026, Cambridge University Press).

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

Everyone’s had something to say about Iran. But they're missing the most important piece.

In this week's powerful editorial, Josh invites you to shift focus away from the tsunami of hot takes, of Trump takedowns, of condemnations and victory proclamations and self-certainty on both sides.

Take a reprieve from the chatter and consider the question most commentators have skipped.

The national director of Turning Point Australia (the Aussie chapter of Turning Point USA) isn't your typical Christian nationalist. He's a 28-year-old Lebanese-Australian influencer, educator and activist.

How should we understand the goals of the new, nationalist right? From Trump to Farage to the National Rally in France, from the Alternative für Deutschland in Germany to the meteoric rise of Pauline Hanson's One Nation party in Australia, it's time to understand who we're dealing with.

Joel Jammal gained popularity protesting Australia's Covid lockdowns. Nigel Farage convinced Charlie Kirk to hand Joel the keys to the Turning Point franchise. He now has more than 600,000 followers and a billion views, with a newspaper and a podcast serving Christian nationalism to hundreds of thousands of people disillusioned with mainstream politics.

This is not your grandpappy's conservative party. Joel joins Josh to debate immigration, Brexit, Trump and the future of democracy.