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The Optimistic Curmudgeon is an interview podcast where Josh Herring interviews expert guests whose credentials and experience help listeners understand truth in a confusing world. We discuss issues under seven areas: economics, politics, education, philosophy, business, virtue, and leadership! May the best ideas win.
The Optimistic Curmudgeon is an interview podcast where Josh Herring interviews expert guests whose credentials and experience help listeners understand truth in a confusing world. We discuss issues under seven areas: economics, politics, education, philosophy, business, virtue, and leadership! May the best ideas win.
Episodes

Monday Oct 27, 2025
Read Plato's Republic: A Conversation with Dr. Thaddeus Kozinski (9x7)
Monday Oct 27, 2025
Monday Oct 27, 2025
Thaddeus Kozinski makes a compelling case for why every student should read Plato's Republic with an excellent teacher. Plato discourses on justice, reality, the human condition, and highlights the possibilities philosophy extends for comprehending our place in the cosmos. Kozinski explicates the Allegory of the Cave, and illustrates throughout the conversation the importance of classical education for recovering a healthy civilization.
Dr. Kozinski's Books
Modernity as Apocalypse: Sacred Nihilism and the Counterfeits of Logos - https://www.amazon.com/Modernity-Apocalypse-Sacred-Nihilism-Counterfeits/dp/1621384837/
Covid 19 and the War Against Reality - https://www.amazon.com/Covid-19-War-Against-Reality/dp/B0F131LDHS/
Amazon Author Page - https://www.amazon.com/stores/Thaddeus-J.-Kozinski/author/B00448NFJC?ccs_id=504bf5ee-4d59-43a5-b58d-8807a3692ed2

Wednesday Oct 15, 2025
Timothy Knotts: Reasoning Together Philosophy (9x6)
Wednesday Oct 15, 2025
Wednesday Oct 15, 2025
Timothy Knotts of @Classical_Conversations explains the latest CC textbook: Reasoning Together Philosophy. He outlines the nature, tradition, and value of philosophy, highlighting the need for homeschool families to be well versed in philosophy. Along the way, he discusses the nature of classical education, the role classical ed plays in creating culture, and the need for increasing biblical literacy. With much discussion of Plato, Aristotle, Kant, Rousseau, and a few others, this is a conversation not to miss! And be sure to check out Tim's other role as a founder of the New England Consortium of Classical Educators Conference!
Links: Classical Conversations: https://classicalconversations.com/
The New England Consortium of Classical Educators: https://www.newenglandcce.com/
Buy the book here: https://tinyurl.com/5569uhcy

Thursday Oct 02, 2025
Failures of Modern Feminism - with Larissa Phillips (9x3)
Thursday Oct 02, 2025
Thursday Oct 02, 2025
Larissa Phillips, columnist at @thefreepress , shares her journey into and out of feminism. Raised in a radical Leftist family, Larissa experienced first hand the limitations of her own physiology. Over the course of her adulthood, she found peace and joy with her husband, her children, and now her farm. This is a rambling conversation that concludes with a discussion of Larissa's work teaching adults essentials of literacy. Check out her work via links below.
"How I Became a Wife" - https://www.thefp.com/p/larissa-phillips-becoming-a-wife-marriage
Larissa's Free Press author page: https://www.thefp.com/w/larissa-phillips
"Toward Ruin or Recovery" on @Quillette (Warning: paywalled) - https://quillette.com/2024/03/20/toward-ruin-or-recovery-celeste-marcus-liberties-journal-yascha-mounk-feminist-metoo/
The Volunteer Literacy Project - https://www.volunteerliteracyproject.org/

Monday Sep 22, 2025
In the House of Tom Bombadil - with C.R. Wiley (9x2)
Monday Sep 22, 2025
Monday Sep 22, 2025
C.R. Wiley of @TheTheologyPugcast explains who Tom Bombadil is. Wiley wrote In the House of Tom Bombadil with @CanonPress , and that book opens a wide ranging conversation about masculinity, femininity, dominion, domination, dating, Adam, and the work of the logos in Tolkien's Legendarium. It's a wonderful discussion mostly grounded in The Fellowship of the Ring. Enjoy!
Links: In the House of Tom Bombadil - https://canonpress.com/products/in-the-house-of-tom-bombadil
The Theology Pugcast - https://thetheologypugcast.com/
Touchstone Magazine - https://www.touchstonemag.com/archives/author.php?id=939

Tuesday Sep 09, 2025
Greta Gerwig, Narnia, and the Culture War: Joseph Holmes (9x1)
Tuesday Sep 09, 2025
Tuesday Sep 09, 2025
Joseph Holmes advances his theory of feminism in contemporary Hollywood: only women are allowed to be positive spiritual figures. Holmes argues that Hollywood has shifted from "men bad, women good" and the "religious or atheist" dichotomy to "men are religious, women are spiritual." As such, Holmes thinks it fits Greta Gerwig's pattern to cast a female voice (rumored to be Meryl Streep) for Aslan in Netflix's forthcoming adaptation of The Magician's Nephew. If you love Narnia, enjoy thinking about Christian filmmaking, or have opinions about the Kendrick brothers' films, don't miss this one!
Topics of discussion include: Barbie, Little Women, House of David, and more.
This episode was inspired by Holmes' essay, "Greta Gerwig’s Aslan And The Coming Faith-Based ‘Gender Culture War’" on Religion Unplugged - https://religionunplugged.com/news/2025/5/9/greta-gerwigs-aslan-and-the-coming-faith-based-gender-culture-war
Also - Check out Joseph Holmes's podcast The Overthinkers here: https://podcasts.apple.com/us/podcast/the-overthinkers/id1510271421
Joseph's website: https://www.josephholmesstudios.com/
Coming Soon - Jim vs. the Future - check out the IMBD listing here: https://www.imdb.com/title/tt33087557/

Wednesday Jun 11, 2025
Wrapping the Re-Enchanting Inklings - Season 8 Finale (8x13)
Wednesday Jun 11, 2025
Wednesday Jun 11, 2025
Dr. Josh Herring reflects on Season 8: The Re-Enchanting Inklings, drawing out connections between guests and suggesting what this season of The Optimistic Curmudgeon says about modernity, the Inklings, and our need to encounter reality.
With shoutouts and callbacks to Annie Crawford, Andrew Lazo, Christiana Hale, Holly Ordway, Landon Loftin, Austin Freeman, Brent Weeks, Steve Beebe, Michael Ward, Sarah Waters, and Rhys Laverty.
Many thanks to this season's sponsors: The C.S. Lewis Institute, and America's Christian Credit Union!
https://americaschristiancu.com/personal/
https://www.cslewisinstitute.org/
We'll be back in the fall of 2025 with Season 9! Until next time, seek the good, live the true, and enjoy the beautiful.

Thursday Jun 05, 2025
C.S. Lewis' Skepticism & The Silver Chair: A Conversation with Annie Crawford (8x12)
Thursday Jun 05, 2025
Thursday Jun 05, 2025
Annie Crawford explains Dr. Michael ward's theory of "donegality," and shows how reading The Silver Chair as C.S. Lewis's lunar novel helps explain the difference between Aslan's Country and the muddled world below. This conversation is largely based on an article Annie wrote for An Unexpected Journal entitled "Finding Faith in Fairy Tales: Answers for Modern Skeptics from C.S. Lewis's The Silver Chair" and Annie explains the nature of modern skepticism and how Lewis works in philosophical responses in the Green Lady's temptation and then Puddleglum's response. Pascal's Wager, the Ontological Argument, Plato's Cave, Freud, Marx, Feurbach, and more---all nestled within The Silver Chair.
Link to Annie's article: https://anunexpectedjournal.com/finding-faith-in-fairy-tales-answers-for-modern-skeptics-from-c-s-lewiss-the-silver-chair/
Sponsor link - America's Christian Credit Union - https://americaschristiancu.com/personal/

Friday May 30, 2025
Till We Have Faces: A Conversation with Fr. Andrew Lazo (8x11)
Friday May 30, 2025
Friday May 30, 2025
Fr. Andrew Lazo offers his interpretation of C.S. Lewis's Till We Have Faces as Lewis's "best book." Lazo reads the novel through The Four Loves, and contends that Lewis's entire project, as it develops across a lifetime of spiritual writing, culminates in this final novel. This conversation also features discussion of the Mere Christians conference, differing views on definitions of love, and lots of Lewisian details. With shoutouts to Michael Ward, @PintsWithJack , @C.S.LewisUndiscovered , and many friends, this is an episode to savor.
Link to Mere Christians: Inspiring Stories of Encounters with C.S. Lewis - https://www.amazon.com/Mere-Christians-Inspiring-Stories-Encounters/dp/1946708321
Sponsor Link: America's Christian Credit Union - https://americaschristiancu.com/personal/

Wednesday May 21, 2025
Wednesday May 21, 2025
Christiana Hale, author of Deeper Heaven: A Reader's Guide to C.S. Lewis's Ransom Trilogy, discusses her essay on pleasure and contemplation in Life on the Silent Planet: Essays on Christian Living from C.S. Lewis's Ransom Trilogy. Medieval cosmology, Perelandra, closing out the teaching season, the Un-Man's temptations of the Green Lady, right and wrong femininity, and more feature in this wide-ranging conversation. With shoutouts to Canon Press, New Saint Andrews College, Thales College, and the Undiscovered Lewis Conference, this conversation ties together a variety of institutions.
Link to Deeper Heaven: https://www.amazon.com/Deeper-Heaven-Readers-Lewiss-Trilogy/dp/1944482563/
Link to Life on the Silent Planet: https://www.amazon.com/Life-Silent-Planet-Christian-Trilogy/dp/1949716252/
Sponsor Link: https://americaschristiancu.com/personal/

Monday May 12, 2025
Arthuriana in C.S. Lewis: A Conversation with Dr. Holly Ordway (8x9)
Monday May 12, 2025
Monday May 12, 2025
Dr. Holly Ordway discusses her essay "Arthur in Edgestow" in Life on the Silent Planet: Lessons in Christian Living from C.S. Lewis's Ransom Trilogy. She explain Lewis's love of Arthurian legends, the choices Lewis makes in incorporating, adapting, and tweaking elements of the Arthurian legendarium in That Hideous Strength. With discussion of Charles Williams, Roger Lancelyn Green, and Merlin, this is a delightful interview with one of the foremost Inklings scholars. Enjoy!
Dr. Ordway's website - https://hollyordway.com/
Books discussed in the interview
Link to Life on the Silent Planet: https://www.amazon.com/Life-Silent-Planet-Christian-Trilogy/dp/1949716252/
Link to The Inklings and King Arthur: https://www.amazon.com/Inklings-King-Arthur-Williams-Barfield/dp/1944769897/
Link to Taliessin through Logres: https://www.amazon.com/Taliessin-through-Logres-Region-Arthurian/dp/0802815782/
Sponsor link: America's Christian Credit Union - https://americaschristiancu.com/personal/
