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Uncomfortable Conversations with Josh Szeps

Josh Szeps
Australia
Donald Trump
Artificial Intelligence
Climate Change
Israel
Free Speech
Mental Health
Social Media
Australian Politics
Social Justice
Cancel Culture
Iran
Democracy
Zionism
Immigration
Education
China
Identity Politics
Comedy
United States

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

PublishesTwice weeklyEpisodes575Founded11 years ago
Number of ListenersCategories
Society & CultureComedyComedy Interviews

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Artwork for Uncomfortable Conversations

Latest Episodes

Is the exhausted majority stuck choosing between two extremes that can’t be satisfied, and what happens when the far left and far right go head to head?

Josh chats with comedy writer and author of I Might Be Wrong, Jeff Maurer, live from a Washingto... more

Is it more ethical to prosecute your moral beliefs, or to understand people who disagree? Who, exactly, is fomenting polarisation? Who is capable, potentially, of political violence?

Is it, perhaps, all of us? Especially those of us convinced we’re ... more

This episode is part of The Best Of series and was originally posted in 2021. Tim Urban’s first appearance on this show remains one of my all-time favourites.

Why are you here? Are we alone in the universe? Will we extinguish ourselves? Why do you p... more

This episode is from the You’re A Good Kid podcast, featuring your humble host, Josh Szeps.

This is a candid look into the life and mind of a boy who grew up in Sydney's inner suburbs and how love, family, and creativity shaped his strong self-confi... more

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Recent Guests

Tim Urban
Blogger and creator of Wait But Why, known for his TED Talk on procrastination
Wait But Why
Episode: "Why are you here?" with Tim Urban
Adam Spencer
Australian mathematics communicator and broadcaster whose NerdNews Substack covers mathematics and AI
NerdNews
Episode: How A.I. is "Demolishing" Mathematics
Owen Fitzpatrick
Psychologist, author of Is Inner Propaganda?
Independent author/psychologist
Episode: Why do smart people believe stupid things?
Sami Shah
Pakistani-Australian comedian, writer, and commentator
Festival of Dangerous Ideas / Crikey / News Weekly
Episode: Free speech, hate speech, and the limits of Liberal tolerance with Sami Shah
Assadi Youssef
Ethical hacker and security advisor
Independent security consultant advising banks and critical infrastructure
Episode: Who's hacking you right now? with ethical hacker Assadi Youssef
William Shatner
Actor and public figure discussing career, aging, and creativity
Episode: William Shatner Doesn’t Want to Die, from The Moynihan Report
Jonathan Haidt
Social psychologist; author of The Righteous Mind and The Coddling of the American Mind
New York University
Episode: Social media broke our ability to agree, with Jonathan Haidt
Megan Phelps-Roper
Former member of Westboro Baptist Church; journalist and activist
Westboro Baptist Church (former); journalist/activist
Episode: “So… *Does* God Hate F*gs?” with Megan Phelps-Roper
Jeff Maurer
Comedy writer, publisher of the I Might Be Wrong substack, former writer on John Oliver
I Might Be Wrong / John Oliver team
Episode: Is there any Room left for moderates? With Jeff Maurer

Host

Josh Szeps
Host known for leading uncomfortable conversations on politics, culture, and society; frequently engages with guests to unpack controversial topics.

Reviews

4.4 out of 5 stars from 3.2k ratings
  • 9/11 episode

    Thoughtful. Thought-provoking.

    Thank you.

    Apple Podcasts
    5
    thermosprotection1
    United Statesa month ago
  • Rage bait doesn’t live up to promise of a complex discussion

    Interesting and valuable concept - the idea that we should be able to have uncomfortable conversations that challenge mainstream groupthink. But Josh is not a good interviewer - frequently interrupting guests before they can get a thought out and one-upping them to try and prove ?intellectual superiority. His style is quite hostile and pugilistic, so I don’t feel that in practice these conversations are truly thought provoking or able to get to the nuance/complexity of the topic.

    Apple Podcasts
    2
    Sarah6538375
    Australia2 months ago
  • Einstein Wilf seems like the smartest person in the room

    Excellent truth . Refreshing to hear the voice of someone who had a seat at the table.

    Josh, on the other hand seems to reflexively Westplain. It’s a pattern.

    Apple Podcasts
    5
    lindaincharlotte
    United States2 months ago
  • Ryan Martin

    This was the best interview for every person in a parenting role.

    Apple Podcasts
    5
    LaylaMG5
    Australia3 months ago
  • Hated by Both

    It’s great to read reviews that hate you from sides of the isle. Please keep contributing to conversations regardless of what your audience wants to hear. Thanks Josh!

    Apple Podcasts
    5
    Hooked On Nature
    Australia4 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Guests bring strong expertise; the debates feel nuanced rather than partisan.
The host asks tough questions but stays civil, keeping conversations constructive.
Listener sentiment varies; some episodes feel pointed or provocative, others deeply insightful.
Production quality and editing are generally tight, making complex topics accessible.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

How A.I. is "Demolishing" Mathematics
Q: Does it matter?
Spencer says understanding why a result works can enable related discoveries and applications. He gives the example of research questioning how a brain cancer drug works, noting that learning its mechanism could help develop similar drugs or use the biological process in other ways.
How A.I. is "Demolishing" Mathematics
Q: So how much is sort of horsepower, and how much is insight beyond the can of mortals?
Spencer distinguishes between AI combining existing mathematical ideas at high speed, which can make researchers more productive, and breakthroughs whose reasoning may be inaccessible to humans. A readable proof can still advance shared understanding, while an opaque proof risks leaving people unable to learn from the result.
How my upbringing shaped my world view with Josh Szeps
Q: What kind of dad do you try and be?
Szeps aims to be adventurous, playful, and present, while acknowledging that work and phone use distract him. He is trying to manage his attention and create more opportunities for family time and shared adventures.
How my upbringing shaped my world view with Josh Szeps
Q: How important was humor in your upbringing?
Szeps says humor was vital to his family, especially to his father, who used jokes and silliness to connect with people. Szeps also relied on humor alongside his verbal and intellectual abilities.
"Why are you here?" with Tim Urban
Q: How do we do it?
Urban says that recognizing social media's risks is already progress, and that open discourse is essential to collective wisdom. He argues people should push back against making it frightening to be wrong or to disagree, and later recommends beginning with honesty about one's beliefs and building courage to express them.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Uncomfortable Conversations

What is Uncomfortable Conversations about and what kind of topics does it cover?

The show centers on provocative, candid conversations that challenge conventional wisdom across politics, culture, and society. Episodes frequently feature executives, journalists, academics, and insiders who bring expert context to hot-button topics such as free speech, gender, parenting, education, and political branding. The host steers conversations toward practical implications and real-world dynamics, often highlighting how narratives shape public discourse more than facts. Listeners can expect thorough debate, diverse viewpoints, and a willingness to tackle controversial subjects with curiosity, civility, and a bias toward unpacking uncomfortable questions. A notable strength is its ability to attract high-profile guests from politic... more

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Which podcasts are similar to Uncomfortable Conversations?

These podcasts share a similar audience with Uncomfortable Conversations:

1. Conversations with Coleman
2. Quillette Podcast
3. Making Sense with Sam Harris
4. The Moynihan Report
5. Blocked and Reported

How many episodes of Uncomfortable Conversations are there?

Uncomfortable Conversations launched 11 years ago and published 575 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Uncomfortable Conversations?

Recent guests on Uncomfortable Conversations include:

1. Tim Urban
2. Adam Spencer
3. Owen Fitzpatrick
4. Sami Shah
5. Assadi Youssef
6. William Shatner
7. Jonathan Haidt
8. Megan Phelps-Roper

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