Whoa, Vol. 2: Conversations on AI × Creativity
Episodes
Bonus: The Age of The Sublime with Robert Greene
12 Mar 2026
Contributed by Lukas
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 aroun...
Why I Don’t Use AI to Write — Oliver Burkeman
14 Nov 2025
Contributed by Lukas
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 ...
Inside the Research Mind Behind Ryan Holiday and Rick Rubin — Billy Oppenheimer
07 Nov 2025
Contributed by Lukas
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 ab...
Every Job Will Become an Art or Die -- Anu Atluru
31 Oct 2025
Contributed by Lukas
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 in...
AI Critics Should Do Some Moral Soul-Searching — Venkatesh Rao
24 Oct 2025
Contributed by Lukas
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...
I Don't Care if a Robot Wrote It. If It's Good, It's Good. — Joan Westenberg
17 Oct 2025
Contributed by Lukas
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...
How David Perell Uses AI to Unlock His Playful Side
10 Oct 2025
Contributed by Lukas
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 timeDemocratic bea...
The AI Debate Is Not About Art, It's About Money — Jasmine Sun
03 Oct 2025
Contributed by Lukas
In this episode we sit down with writer Jasmine Sun to talk about:Why AI pushed her to leave Substack and write full-timeHow she actually uses ChatGPT...
Quit Optimizing for Algorithms. Make Something Weird — Robin Sloan
25 Sep 2025
Contributed by Lukas
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...
The "Talking Dog" Theory of AI — Seth Godin
19 Sep 2025
Contributed by Lukas
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 go...
Why Substack's Head of Design Thinks LLMs are Overrated -- Mills Baker
04 Sep 2025
Contributed by Lukas
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 w...