Whoa, Vol. 2: Conversations on AI × Creativity

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 MacTrust, but humans: why provenance matters even if you “can’t tell” who wrote itThe creator’s edge: double down on the purely human rather than joining the generic raceFirst drafts are the thinking: why outsourcing early or late stages erodes voice and meaningScarcity gives value: why using your finite time confers worth readers can actually feelArtisanal future: human-made work as microbrew, not mass commodityIf 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. 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/whoa⁠⁠Brought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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 betRyan’s note card system: “make notes for an ignorant stranger” so future-you can use themFrom serendipity to synthesis: stacking 8–12 cards into a theme and letting weird specificity emergeWhere AI fits: upstream tutoring for tricky references, downstream lists and sentence variants—never the sparkSpeed vs. substance: is AI actually good, or just fastNeck-down work: when to stop optimizing and just do the tedious thingReading as an edge in the AI era: finding stories outside the training dataIf 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. 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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 edgeThe skills triage: in an AI world, human skills become extinct, art, or sportVenture as the last job: allocation, bets, and why taste still mattersMedia, machines, medicine: the 3 arenas she’s betting on for the next decadeWriting with AI, the right way: upstream ideation, downstream critique—protect the messy middleDoom-prompting is the new doomscrolling: avoiding the dopamine trapIf 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. 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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-speakThe concept of individual authorship as a very recent invention Treating LLMs as channels for our shared cultural inheritance, not plagiarism machinesWhy creative work isn’t “labor” and the middle-class myth that effort guarantees economic valueRisk as the price of originality and why most AI slop is low-risk human behavior How Venkatesh actually writes with AI and playful “Lego” ideationWhy disclosing AI-use in your writing will soon disappear 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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. 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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 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 worseHow David actually writes with AI (hint: it involves Theo Von)Why David decided to end Write of PassageNew York vs. LA vs. SF: the unspoken culture war over AI in publishing and entertainmentPersonalization vs. prose: why he’ll start with deep research before a bookWhy David's bullish on spirit-lifting, live performance and theater in an AI-saturated world… and moreWhoa 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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, Claude, and Gemini (and what each is best at)Why she’s pro-transparency about using AI—even when it upsets peopleThe AlphaGo lesson: letting AI make you more creative, not lessThe real anxiety underneath “AI ruins art” (it’s economics, not aesthetics)Custom instructions, long-context workflows, and how she summarizes 20,000-word reportsWhy she thinks AGI is less milestone, more vibe … and moreWhoa 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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 hypeWhy AI writing lacks the density of choices that makes human work feel aliveThe paradox of AI humor and why real art depends on things being a little weirdHis shift from online publishing to hand-printed zines—and why “offline math” works better for artistsHow he actually uses AI for travel and editing, and where it still falls shortWhy discovery and criticism matter more than ever in the age of algorithmsand moreWhoa 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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 AIHis “talking dog” theory and why most AI output is still just mayonnaiseWhy he thinks community will be the scarce thing people actually pay forHow 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 easierHis prediction for where humans will be in 10 years… and moreWhoa 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

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 creatorsHow he uses (and doesn't use) AIWhy he's bearish on LLMsHow Mills sees Substack changing in the coming yearsSubstack’s lead engineer's hot take on how AI impacts timelines of coding projectsHis prediction for where humans will be in 10 years...and moreWhoa 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/whoaBrought to you by MercuryThis 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.DisclaimerMercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.