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 demands a new kind of grit.

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 white leftists in San Francisco (where Kmele lives) and the meaning of the cosmos.

After having a falling-out with Silicon Valley, Kmele was recently appointed the editor-at-large of Tangle, an independent news website that summarises arguments from the right, left, and center. Kmele's first column was this absolute barnstormer. He also serves on the board of directors of the Foundation for Individual Rights and Expression and co-hosts the smash hit podcast The Fifth Column.

Don't miss this uplifting, provocative, moving, mind-expanding chat.

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 since become an elder statesman of reason and logic, advocating mindfulness and rationality through his meditation app, Waking Up, and his podcast, Making Sense. 

Sam has always been a generous supporter of Josh's work and was kind enough to invite us to his private studio during the Szeps Live Around-the-World Podcast Marathon for a two-and-a-half-hour livestream. Enjoy this sparkling meeting of minds.

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 between marrying Donald Trump or f**king Tucker Carlson?

Josh welcomed Matt Welch and Kmele Foster, co-hosts of The Fifth Column, along with the owner of the Cellar, Noam Dworman, who has his own fiery podcast, Live From the Table. Blocked and Reported's Jesse Singal even swung by for a round of "Jew In The Hot Seat".

The room was packed. The drinks were flowing. Enjoy the fun.

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 intellectual interview podcasts, Conversations with Tyler.

He's written for the New York Times, the Wall Street Journal and the Washington Post, but he's now a contributor at

The Free Press. We're grateful to the FP for helping us to boost this mind-expanding conversation, which streamed live from Tyler's bucolic porch in northern Virginia.

Watch this conversation on YouTube. And you’re missing out on our best ad-free content if you haven’t popped over to the Uncomfy Convos Substack page.

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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 with Josh in her home in the suburbs outside Washington, D.C. for a livestream about belief, justice, gender, and tolerance, on the Szeps Live Round-the-World Podcast Marathon.

Watch this conversation on YouTube. And you’re missing out on our best ad-free content if you haven’t popped over to the Uncomfy Convos Substack page.

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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.

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 sanity, recovery, parenting, and what it means to grow older without growing rigid.

This episode is a recording of a Szeps Live stream which you can watch on YouTube or Substack if you wanna see Osh 'n' Josh's purdy faces.

And just a heads-up to stay across Uncomfortable Conversations in the next few months because, as we discuss in this episode, Josh is about to deliver some killer livestreamed celebrity content during an imminent Szeps Live around-the-world tour. If you've been putting off figuring out how to download the Substack app, do it now in one click and follow this show to keep abreast of what'll be a delightful tsunami of mind-expanding chats.

Osher’s new illustrated book about mental wellness is called "So What, Now What?”

Watch this conversation on YouTube. And you’re missing out on our best ad-free content if you haven’t popped over to the Uncomfy Convos Substack page.

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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 behavioural issues just like he did. His clinic has a waiting list that's years-long.

Billy and Josh debate masculinity, permissive parenting, rigid schools, the over-diagnosis of mental "diseases" in kids, and whether kids are coddled these days. Josh wants to understand why the Greatest Generation was able to win WWII without the high rates of clinical anxiety and depression that supposedly afflict today's snowflakes. Billy says that's exactly the wrong way to look at it.

Billy also hosts the #1 parenting podcast in Australia, Pop Culture Parenting, and is the founder of Guiding Growing Minds, a social enterprise that helps children to live meaningful lives. His book is Ten Things I Wish You Knew About Your Child’s Mental Health.

Josh walked out of this conversation feeling like he'd received a bracing, mind-expanding free therapy session. Unleash your inner twelve-year-old and take a seat.

Watch this conversation on YouTube. And you’re missing out on our best ad-free content if you haven’t popped over to the Uncomfy Convos Substack page.

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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 Independent Studies. He's a data scientist with postgrad qualifications in physics who leads the centre's energy systems research. He argues that most assessments of renewable energy are incomplete or misleading.

If you missed Josh's chat with the renewable-energy engineer and entrepreneur Saul Griffith on June 10th, you might want to give it a listen first here. Here, Aidan and Josh debate how to think about generating and supplying cheap power to a high-tech society... and whether the answer to our growing energy needs is staring us right in the face.

Watch this conversation on YouTube. And you’re missing out on our best ad-free content if you haven’t popped over to the Uncomfy Convos Substack page.

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