Whoa, Vol. 2: Conversations on AI × Creativity

About Whoa, Vol. 2: Conversations on AI × Creativity

Whoa, Vol. 2: Conversations on AI × Creativity is a limited series of ten in-depth conversations with some of our favorite thinkers and creatives. We explore how artificial intelligence is changing and challenging creative work. Brought to you by sublime.app, the knowledge tool that sparks creativity and Mercury — business banking trusted by 200,000+ entrepreneurs.

Publisher

Sublime

Category

technology

Language

en

Explicit

No

First episode

4 Sept 2025

Latest episode

12 Mar 2026

Latest episodes

11 episodes in the feed.

1. 

   12 Mar 2026

   Bonus: The Age of The Sublime with Robert Greene

   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 phones despite the sublimity around us, the mystery of consciousness, his views on AI, how to reclaim a sense of awe in modern life, and lots more.

2. 

   14 Nov 2025

   Why I Don’t Use AI to Write — Oliver Burkeman

   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 down on the purely human rather than joining the generic race First drafts are the thinking: why outsourcing early or late stages erodes voice and meaning Scarcity gives value: why using your finite time confers worth readers can actually feel Artisanal future: human-made work as microbrew, not mass commodity If you make things, Oliver’s counsel is simple: don’t outsource the part that gives the work its meaning. Keep your drafts human, use tools as tools, and build trust by letting readers feel a person on the other end. Subscribe for more candid conversations on craft, meaning, and making work that lasts. Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: ⁠⁠https://sublime.app/whoa⁠⁠ (https://sublime.app/whoa) Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app.If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit ⁠⁠https://mercury.com⁠⁠ (https://mercury.com) today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

3. 

   7 Nov 2025

   Inside the Research Mind Behind Ryan Holiday and Rick Rubin — Billy Oppenheimer

   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 use them From serendipity to synthesis: stacking 8–12 cards into a theme and letting weird specificity emerge Where AI fits: upstream tutoring for tricky references, downstream lists and sentence variants—never the spark Speed vs. substance: is AI actually good, or just fast Neck-down work: when to stop optimizing and just do the tedious thing Reading as an edge in the AI era: finding stories outside the training data If you make things, Billy’s playbook is simple: read widely, capture diligently, stack note cards until a theme clicks—then use AI as a tutor and helper, not a substitute. Subscribe for more candid conversations on craft, research, and making work that lasts. Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa (https://sublime.app/whoa) Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app.If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com (https://mercury.com) today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

4. 

   31 Oct 2025

   Every Job Will Become an Art or Die -- Anu Atluru

   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, machines, medicine: the 3 arenas she’s betting on for the next decade Writing with AI, the right way: upstream ideation, downstream critique—protect the messy middle Doom-prompting is the new doomscrolling: avoiding the dopamine trap If you’re building or creating, Anu’s prompt is simple: choose better tools—and better people. Use AI to offload the draining parts, keep your human “messy middle,” and express your taste where it counts. Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app.If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

5. 

   24 Oct 2025

   AI Critics Should Do Some Moral Soul-Searching — Venkatesh Rao

   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” and the middle-class myth that effort guarantees economic value Risk as the price of originality and why most AI slop is low-risk human behavior How Venkatesh actually writes with AI and playful “Lego” ideation Why disclosing AI-use in your writing will soon disappear Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app. If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

6. 

   17 Oct 2025

   I Don't Care if a Robot Wrote It. If It's Good, It's Good. — Joan Westenberg

   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 you love (writing, music) Editors vs. yes-bots: why Joan won’t trust AI for feedback The real fear behind AI backlash: replacement after decades of creative devaluation Choosing friction: manual workflows, single‑purpose tools, and keeping agency Comms without spam: building relationships in a world drowning in AI-generated pitches Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app. If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

7. 

   10 Oct 2025

   How David Perell Uses AI to Unlock His Playful Side

   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 end Write of Passage New York vs. LA vs. SF: the unspoken culture war over AI in publishing and entertainment Personalization vs. prose: why he’ll start with deep research before a book Why David's bullish on spirit-lifting, live performance and theater in an AI-saturated world … and more Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app. If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

8. 

   3 Oct 2025

   The AI Debate Is Not About Art, It's About Money — Jasmine Sun

   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 aesthetics) Custom instructions, long-context workflows, and how she summarizes 20,000-word reports Why she thinks AGI is less milestone, more vibe … and more Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app. If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

9. 

   25 Sept 2025

   Quit Optimizing for Algorithms. Make Something Weird — Robin Sloan

   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 better for artists How he actually uses AI for travel and editing, and where it still falls short Why discovery and criticism matter more than ever in the age of algorithms and more Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app. If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

10. 

    19 Sept 2025

    The "Talking Dog" Theory of AI — Seth Godin

    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 he believes Claude is a “close friend” What creators should really be asking: how can AI make my work harder, not easier His prediction for where humans will be in 10 years … and more Whoa Vol. 2This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work. 👉 Get your copy of the zine: https://sublime.app/whoa Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app.If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

11. 

    4 Sept 2025

    Why Substack's Head of Design Thinks LLMs are Overrated -- Mills Baker

    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 where humans will be in 10 years ...and more Whoa Vol. 2 This episode is part of a limited series of ten in-depth conversations put together by sublime.app with some of our favorite thinkers and creatives where we explore how artificial intelligence is changing and challenging creative work.👉 Get your copy of the zine: https://sublime.app/whoa (https://sublime.app/whoa) Brought to you by Mercury This interview is made possible by Mercury — business banking trusted by 200,000+ entrepreneurs and hands-down our favorite tool for running sublime.app (http://sublime.app).If you’re a founder or business builder of any type and haven’t tried Mercury yet, visit https://mercury.com (https://mercury.com) today. Disclaimer Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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