Hamish is one of the co-founders of Substack and its chief writing officer. He’s a former reporter for the tech blog PandoDaily and a former lead writer for Tesla. He’s the author of Insane Mode: How Elon Musk’s Tesla Sparked an Electric Revolution to End the Age of Oil, and his new book is called How to Save the Media. A native New Zealander, and former journalist himself, Hamish has kept writers at the heart of the Substack model, first pioneered by the Dish.

The episode was recorded on November 10, 2026, and aired on November 13. Timestamps for the main sections:

* 06:18: Hamish’s upbringing in New Zealand and his journalism

* 28:00: The early internet and the advent of blogs and the Dish

* 50:00: The rise of social media and Substack’s challenge to it

* 133:27: Substack standing strong against censorship

For two audio clips — when the enshittification of social media began, and the challenges of affordability on Substack — go here and here on YouTube.

More topics covered: Hamish’s mom a teacher of Maori culture; his dad a physicist on the ozone layer; nightlife journalism in Hong Kong; clashing with Elon and his lawyers; meeting his Substack co-founders working at Kik; the pamphleteering era ended by newspapers; the pioneering of Matt Drudge; Kinsley and Slate; Evan Williams and Blogger; the origins of the Daily Dish; mass intimacy; war bloggers after 9/11; the Dish getting donations in 2002; blogging at Time, The Atlantic, and The Daily Beast; the ad model failing; the unraveling of mags; the Dish going independent in 2013; TinyPass; Patreon; the Daily Dish retiring; NY Mag firing me and jumping to Substack; Yglesias leaving Vox; Bari selling The Free Press to David Ellison; Tina Brown reborn as a writer; media bias on Israel; cancel-culture threats to Substack; Twitter and enshittification; the internet becoming TV; Grindr and Sniffies; and the challenges of a scaled-up Substack.

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Michael is a journalist and historian. He’s currently the senior political analyst for the Washington Examiner, a resident fellow emeritus at the American Enterprise Institute, and the longtime co-author of The Almanac of American Politics.

The episode was recorded on November 4, 2026, and aired on November 6. Timestamps for the main sections:

* 04:29: Michael’s upbringing and his early career

* 24:46: The tsunami that swept away Republicans this week

* 43:23: The electoral impact of the Iran War

* 51:21: The Dem victories in Texas and the immigration issue

* 102:56: El-Sayed and shifting attitudes toward Israel

* 115:11: The future of the GOP with Trump as a lame duck

For two audio clips — on how the GOP dummymandered itself, and if Texas is really turning blue — go here and here on YouTube.

More topics covered: Michael raised in the Detroit area; the Great Migration; his Dem youth turning conservative; the Dem coalition of blacks and college whites that started in the ‘60s; the decades of Dem dominance in the House until ‘94; Clinton and Carville; the narrowing of POTUS victories since the ‘90s; gerrymandering; the GOP’s “thumping” in the 2006 midterms; Trump’s “they/them” ad and McDonald’s stunt; his gilded obsessions; his family cashing in; his lonely support of tariffs; the trade war with Canada; the ICE and DHS debacles; Mamdani and the rise of DSA; the Iran War and Graham’s death; his sister’s loss; AIPAC spending big against El-Sayed; the chilling anti-Israel ad in Michigan; the shocking defeat of Abbott; Talarico’s triumph; Hispanics turning on Trump; the border; the youth vote and men swinging against Trump; Narcissus at the Reflecting Pool; DeSantis speaking out; and Vance’s tweet dissenting over Trump’s war.

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Catherine is a philologist with a particular focus on Augustine of Hippo. She’s both the Leslie Clark Professor in the Humanities and a Professor of Greek, Latin, and Classical Studies at Bryn Mawr College. The author of many books, her most recent is Augustine the African. We had an exhilarating afternoon talking about this African who helped frame the West.

The episode was recorded on October 27, 2026, and aired on October 30. Timestamps for the main sections:

* 07:43: How Catherine came to specialize in Augustine

* 24:19: The profound influence of his mother

* 42:56: His conversion to Christianity

* 52:42: The deaths of his mom, son, and best friend in quick succession

* 101:23: His decades preaching and writing in Hippo

For two audio clips — on Augustine’s struggles with sex, and the moment he converted to Christianity — head to our YouTube page.

More topics covered: Catherine growing up mostly in Oxford; her family’s dedication to the classics; the Romans’ Gaza-like destruction of Carthage; the ferocious debating style of Augustine; his struggle to be humble; his emotional openness; his disgust over Roman games and executions; his early interest in Manichaeism; the problem of evil; sex in the Garden of Eden; Augustine’s persistent horniness; his 14-year relationship with a woman he ditched for an arranged marriage; his close bond with his Christian mother who long tried to convert him; the unprecedented nature of his Confessions; Oakeshott’s awe; Augustine on friendship; memory and time; The City of God filled with relentless counter arguments; Wittgenstein and the limits of language; the miracles of everyday life; the homelessness of Jesus and St Francis; and how Rome was falling at the end of Augustine’s life.

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