“We read so as not to feel alone.” — C.S. Lewis (possibly)

Dan Turello is a cultural historian of medieval Italy, a much published photographer, and the author of the new Connection: How Technology Can Make Us Better Humans. I’m sceptical. Especially the promise (or illusion) of better humans. But Turello’s definition of technology goes back further than most — all the way to the original fig leaf. When Adam and Eve were expelled from the Garden, the first thing they did, he reminds us, was cover their bodies. Technology, then, in Turello’s framing, is everything that extends beyond the human body. Clothing is technology. Double-entry bookkeeping is technology. The iPhone is just the latest chapter of our technology story that began at the beginning.

His most surprising argument is that our current tech anxiety has medieval roots. St. Francis of Assisi was what he calls a trust-fund kid “avant la lettre” — his father being a wealthy 13th century silk merchant at a time when northern Italy was Silicon Valley. Francis sold some of his dad’s silk, gave the money away, stripped naked before a bishop, and founded a counterculture movement. The first tech backlash, Turello suggests, wasn’t against AI. It was against double-entry bookkeeping. Dante, writing a generation later, idealised an earlier, simpler Florence — what scholars call “paleolithic chic.” No makeup, no ornate clothing, no fleeing to immoral cities. Sound familiar?

On AI, Turello goes a bit Saint Francis on us. Large language models, he fears, generate material without lineage — you can’t trace where the ideas came from, can’t triangulate the sources, can’t validate against reality. Technology is about power, Turello argues — about who controls the storyline. Making us better humans, then, requires recovering a sense of agency. Thus he argues that we should stop outsourcing our thinking, our writing, our photography to machines. Dante wrote the entire Divine Comedy without Claude. These days, we can barely write an email without a little help from our friends at ChatGPT. Machiavelli donned the robes of the past to think and write. We might try putting ours on too. But then isn’t that a tech solution too?

Five Takeaways

• St. Francis Was a Trust-Fund Kid Who Invented Counterculture: His father was a wealthy silk merchant in 13th-century Italy, at the dawn of Europe’s commercial revolution. Francis sold his father’s silk, gave the money away, stripped naked before a bishop, and founded an order that rejected the mechanisms of early capitalism. The first tech backlash wasn’t against AI. It was against double-entry bookkeeping.

• Technology Is Everything Beyond the Naked Human Body: Turello’s definition goes back to Genesis. When Adam and Eve were expelled from the Garden, the first thing they did was cover their bodies. Fig leaves are technology. Clothing is technology. The iPhone is just the latest iteration of a metaphysical problem that’s been destabilising us since the Fall.

• Dante Wrote the Divine Comedy Without Being Able to Edit: He penned an entire macrocosm of the medieval world from memory, without the ability to rewrite in any meaningful way. Turello thinks Dante would be concerned that we’re losing our memories, our ability to tell a coherent narrative for our lives, and that our existence has become too fragmented. We can barely write an email without ChatGPT.

• LLMs Generate Material Without Lineage: Technology is about power — about who controls the storyline. Large language models produce text without traceable sources, without verifiable origins, without lineage. You can’t triangulate where the ideas came from. That’s not intelligence. That’s a crisis of provenance.

• Agency Still Matters: Turello’s hope for humanity is that we recover a sense of agency — the belief that our choices, friendships, relationships, and communities are ours to shape. The alternative is technological determinism: the machine decides. Machiavelli donned the robes of the past to think and write. We might try putting ours on too.

About the Guest

Dan Turello is a writer, cultural historian, and photographer. A Technology and Humanity Fellow at Florida Atlantic University’s Center for Future of Mind, AI & Society, his work has appeared in the New Yorker, the Washington Post, and the Los Angeles Review of Books. Connection: How Technology Can Make Us Better Humans is published by Columbia University Press.

References:

• Connection: How Technology Can Make Us Better Humans by Dan Turello (Columbia University Press, 2026) — the book under discussion.

• Episode 2840: What Came First: Stories or Language? — Kevin Ashton on storytelling preceding language, a natural companion.

• Episode 2839: Have Our iPhones Eaten Our Brains? — Nelson Dellis on memory, cognitive atrophy, and outsourcing our minds.

• Walter Benjamin, The Work of Art in the Age of Mechanical Reproduction — referenced in the conversation on technology and power.

About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,800 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.

Chapters:

(00:00) - Introduction: has technology made you a better human?
(03:22) - The iPhone vs. the decisive moment: Bresson and photography
(05:39) - The orange cushion: an ode to imperfection
(06:27) - St. Francis of Assisi: the first tech critic
(07:22) - 800 years of tech anxiety: from double-entry bookkeeping to AI
(11:27) - Žižek, capitalism, and the love-hate relationship with technology
(13:50) - Fig leaves to iPhones: technology as everything beyond the naked body
(15:00) - Marinetti, Svevo, and the mammoth: technology as relationship
(17:54) - Walter Benjamin, The Matrix, and who controls the storyline
(20:51) - Bresson’s decisive moment vs. Nietzsche’s blow it up
(22:25) - Agency under attack: reclaiming embodied experience
(25:47) - Machiavelli donning the robes of the past
(28:44) - Nost...