

Uncomfortable Conversations with Josh Szeps
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
A DM Podcast
Episodes
Mentioned books

15 snips
Aug 14, 2025 • 39min
SZEPS WORLD TOUR – MEGHAN DAUM on What You’re Not Supposed to Say
Join humorist and cultural critic Meghan Daum as she chats about untamed conversations in today's society. From the complexities of gender identity legislation to the quirks of enjoying solo adventures in LA, Meghan shares her comedic takes. She recounts her unexpected fame on The Oprah Winfrey Show and discusses the nuances of cancel culture. With insights from her community, The Unspeakeasy, she emphasizes the value of safe spaces for open dialogues, all while adding a dash of humor about wild encounters in Australia.

26 snips
Aug 11, 2025 • 1h 21min
SZEPS WORLD TOUR - RICH ROLL on Liberty, Loneliness & Legacy
Join Rich Roll, an ultramarathoner and bestselling author who champions endurance and personal reinvention, as he dives into the implications of America's obsession with personal liberty. He argues that this fixation may actually hinder our freedoms and fuels a loneliness crisis. The conversation explores the shift in community dynamics due to modern distractions, the nuances of sobriety, and the evolving nature of relationships in an AI-driven world. Rich also reflects on legacy, meaning, and the pursuit of purpose over mere happiness.

24 snips
Aug 8, 2025 • 1h 24min
SZEPS WORLD TOUR - KMELE FOSTER on Race, Spirituality & 'Wokeness'
Kmele Foster, Editor-at-large of Tangle and co-host of The Fifth Column, dives deep with Josh into race and identity. They explore parenting in racially charged environments and the struggle for understanding amid polarizing narratives. Kmele critiques the concept of wokeness, arguing against enforced equality and emphasizing personal experiences. The conversation touches on the complexity of privilege, the power of literature in shaping identity, and the role of mindfulness in navigating life's challenges. It's a thought-provoking, engaging discussion!

71 snips
Aug 5, 2025 • 1h 8min
SZEPS WORLD TOUR - SAM HARRIS on Making Sense of Life
Sam Harris, an influential podcaster and neuroscientist known for championing mindfulness, dives into some intense topics. He tackles the responsibility of podcasters in voicing controversial ideas while questioning the ethics of AI and its impact on warfare. Harris discusses the complexities of consciousness, ethical dietary choices, and his personal stance on sensitive social issues. His fearless engagement with topics like jihad and modern ideologies reveals a captivating journey through reason and the challenges of navigating critical conversations in today's world.

9 snips
Jul 31, 2025 • 39min
On Stage in NYC: Panel Show at the Comedy Cellar
Join Matt Welch and Kmele Foster, co-hosts of The Fifth Column podcast, for a fiery live panel at the Comedy Cellar. They discuss the evolving role of satire in politics and how humor can challenge authority. The duo tackles the media's collapse and the rise of podcasting as a news source. They debate the ethical dilemmas of platforming controversial voices while sharing hilarious anecdotes, including one about Epstein's Island. It’s a night of laughter, insightful critiques, and the absurdities of today's media landscape.

64 snips
Jul 29, 2025 • 1h 23min
SZEPS LIVE TOUR - TYLER COWEN on Inequality, Abundance, & Using A.I. to Achieve 'Intellectual Immortality'
Tyler Cowen, a renowned economics professor at George Mason University and influential blogger at Marginal Revolution, dives into pressing topics like urban inequality, critiquing traditional solutions like rent control. He discusses the nuanced relationship between immigration policies and economic sustainability amid societal concerns. Cowen also explores the tensions around free speech in academia and the intersection of AI with intellectual discourse, weaving in personal insights about happiness and the future of knowledge.

14 snips
Jul 27, 2025 • 40min
SZEPS LIVE TOUR: "Atheism, Wokeness & Islam" with Sarah Haider
Sarah Haider, co-founder of Ex-Muslims of North America and outspoken advocate for those leaving Islam, opens up about her transformative journey from atheism to exploring spirituality. She addresses the unsettling religious undertones within progressive ideologies, revealing her disillusionment with the existing atheist movement. The conversation also dives into the emotional complexities of belief, the struggle for meaningful dialogue in cultural debates, and the moral imperatives that shape ethical frameworks in today's society.

Jul 26, 2025 • 1h 12min
THE SZEPS LIVE WORLD TOUR IS UNDERWAY
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 the SZEPS 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 filter. For the next two weeks, Josh will go head to head, live, with some of the world’s most fascinating minds before a global audience in back-to-back foreign locales. From London to Los Angeles, New York to Malibu, Josh and his long-suffering producer, Jono, are hopscotching the planet to visit a parade of iconoclasts and intellectual troublemakers, broadcasting raw, unfiltered conversations sometimes multiple times a day. To enjoy every morsel, subscribe for free to get notified whenever we go live. You'll be able to watch every episode as it streams in real time. To catch up afterwards, about half the shows will be exclusive for paid subscribers. For the price of a cup of coffee a month, you'll get the whole enchilada. All will be available on your podcast app too. The tour's centrepiece will be a high-voltage live event at New York’s iconic Comedy Cellar – the stomping ground of Seinfeld, Dave Chappelle and Robin Williams – on Tuesday July 29th at 6pm ET (11pm in London, 3pm in LA, 8am Wed in Sydney). Put it in your calendar. It'll be a no-holds-barred panel discussion with some of the biggest names in New York journalism. Your normal podcast release schedule may be a little wonky while we fly blind around the planet, streaming live with no safety net, chasing the most fascinating minds… while jet lag fries ours. But you're a big kid. You can handle it. Today's episode is the first cab off the rank - a livestream from a Brooklyn rooftop with panoramic views of Manhattan and the one-&-only Jesse Singal, co-host of the smash hit podcast Blocked and Reported, and one of America's most courageous reporters on youth gender medicine. Buckle up, humans, for the most audacious live-streaming event in Substack's history.

7 snips
Jul 21, 2025 • 1h 8min
"How Not to Feel Like a Failure (When Fame & Fortune Aren't Enough)" with TV Host Osher Günsberg
Osher Günsberg, a well-known Australian TV host and mental wellness advocate, engages in a candid discussion about navigating fame and personal struggles. He shares insights on managing anxiety, depression, and the misconceptions surrounding success. The conversation touches on the importance of resilience, confronting personal pain, and finding meaning in life beyond surface achievements. With humor and heartfelt anecdotes, Osher emphasizes the need for self-reflection and the pursuit of genuine fulfillment in a fast-paced world.

11 snips
Jul 17, 2025 • 57min
PREMIUM: "How to Raise an Awesome Kid (and be an Awesome Grown-Up)" with Dr Billy Garvey
Dr. Billy Garvey, a leading developmental paediatrician and founder of Guiding Growing Minds, dives into pressing issues surrounding childhood mental health. He and host Josh Szeps tackle the surge in ADHD and anxiety, questioning the impact of modern parenting and education. They explore masculinity, the challenges of diagnosing developmental disorders, and the complexities of neurodiversity in schools. The need for a balance between unconditional love and allowing freedom in parenting is also discussed, making for a thought-provoking conversation on raising resilient kids.