Whoa, Vol. 2: Conversations on AI × Creativity

Robert Greene is the bestselling author of The 48 Laws of Power, The Laws of Human Nature, and several other classics read by millions of people around the world. He’s spent the last seven years writing a book about the sublime. After suffering a stroke that made typing difficult, he’s had to write this book by hand. In this conversation we talk about why our minds are shrinking to the size of pho...

In this episode we sit down with Oliver Burkeman (author of Four Thousand Weeks) to talk about AI, meaning, and why the value of creative work hinges on a human consciousness behind it. We get into: Tools, not companions: why he avoids “relationships” with AI and treats it like a pen or a Mac Trust, but humans: why provenance matters even if you “can’t tell” who wrote it The creator’s edge: double...

In this episode we sit down with Billy Oppenheimer (researcher/writer for Ryan Holiday and Rick Rubin; author of the Six at Six newsletter) to talk about taste, note cards, and using AI without losing the human filter.  We get into: AI as tool, taste as foundation: why resonance with readers remains an impossible bet Ryan’s note card system: “make notes for an ignorant stranger” so future-you can...

In this episode we sit down with writer and investor Anu Atluru  to talk about teams, taste, and why AI shifts work from labor to leverage. We get into: “I don’t want an AI, I want a teammate”: how to pick the 5–10 people who amplify your edge The skills triage: in an AI world, human skills become extinct, art, or sport Venture as the last job: allocation, bets, and why taste still matters Media,...

In this episode we sit down with writer, theorist, and consultant Venkatesh Rao to talk about authorship, risk, and why AI is pushing us back to a pre-Gutenberg culture. We get into: How “AI alignment” became PR-speak The concept of individual authorship as a very recent invention Treating LLMs as channels for our shared cultural inheritance, not plagiarism machines Why creative work isn’t “labor”...

In this episode we sit down with writer and strategist Joan Westenberg to talk about creativity and using AI without losing your humanity. We get into: The essay that blew up: deleting her “second brain” and ditching productivity guilt Human in the loop: why tools are neutral—and responsibility isn’t Joan's AI rule: use it for the stuff you hate (titles, charts, video edits), never for the stuff y...

In this episode we sit down with writer Jasmine Sun to talk about: Why beauty and craftsmanship—not AI—are the real story of our time Democratic beauty: why everyday public spaces used to lift the human spirit (and why they don’t now) The “paradox of abundance”: why AI makes the best better and the average worse How David actually writes with AI (hint: it involves Theo Von) Why David decided to en...

In this episode we sit down with writer Jasmine Sun to talk about: Why AI pushed her to leave Substack and write full-time How she actually uses ChatGPT, Claude, and Gemini (and what each is best at) Why she’s pro-transparency about using AI—even when it upsets people The AlphaGo lesson: letting AI make you more creative, not less The real anxiety underneath “AI ruins art” (it’s economics, not aes...

In this episode we sit down with Robin Sloan to talk about: What it was like experimenting with GPT back in 2017—and whether he burned out before the hype Why AI writing lacks the density of choices that makes human work feel alive The paradox of AI humor and why real art depends on things being a little weird His shift from online publishing to hand-printed zines—and why “offline math” works bett...

In this episode we sit down with Seth Godin to talk about: Why AI is like the weather (and why arguing for or against it misses the point) How he’s gone from 1 hour to 7 hours of daily creativity with AI His “talking dog” theory and why most AI output is still just mayonnaise Why he thinks community will be the scarce thing people actually pay for How he uses Claude and ChatGPT differently—and why...

In this episode we sit down with Mills Baker, Head of Design at Substack to talk about: What he's witnessing AI do to Substack's ecosystem of writers and creators How he uses (and doesn't use) AI Why he's bearish on LLMs How Mills sees Substack changing in the coming years Substack’s lead engineer's hot take on how AI impacts timelines of coding projects His prediction for wher...