Uncomfortable Conversations with Josh Szeps (private feed for ccravensands@gmail.com)

Uncomfortable Conversations with Josh Szeps (private feed for ccravensands@gmail.com)

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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. uncomfortableconversations.substack.com

Episode List

SZEPS WORLD TOUR - RICH ROLL on Liberty, Loneliness & Legacy

Aug 11th, 2025 7:00 PM

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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit uncomfortableconversations.substack.com/subscribe

SZEPS WORLD TOUR - KMELE FOSTER on Race, Spirituality & 'Wokeness'

Aug 6th, 2025 8:58 AM

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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit uncomfortableconversations.substack.com/subscribe

SZEPS WORLD TOUR - SAM HARRIS on Making Sense of Life

Aug 2nd, 2025 1:46 AM

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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit uncomfortableconversations.substack.com/subscribe

On Stage in NYC: Panel Show at the Comedy Cellar

Jul 31st, 2025 6:13 PM

This is a free preview of a paid episode. To hear more, visit uncomfortableconversations.substack.comIt 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 t…

SZEPS WORLD TOUR - TYLER COWEN on Inequality, Abundance, & Using A.I. to Achieve 'Intellectual Immortality'

Jul 29th, 2025 1:33 PM

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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit uncomfortableconversations.substack.com/subscribe

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