Whoa, Vol. 2: Conversations on AI × Creativity

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

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Nov 7, 2025

Guest

Billy Oppenheimer

Billy Oppenheimer, a researcher and writer for Ryan Holiday and Rick Rubin, dives into the intersection of creativity and AI. He shares his unique note-card research system, emphasizing how to capture ideas for future clarity. Oppenheimer discusses the unpredictable nature of taste and why AI should serve as a tutor rather than a crutch. With insights on cultivating deep knowledge and finding inspiration outside AI’s reach, he argues that the joy of creative synthesis comes from personal engagement and diligent reading.

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Transcript

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Episode notes

insights

INSIGHT

Taste Remains The Creative North Star

Taste remains the fundamental and unautomatable anchor of creative work despite better AI tools.
Resonance with an audience is still a gamble no model can predict with certainty.

question_answer

ANECDOTE

Adapted Note-Card System For Serendipity

Billy learned Ryan Holiday's note-card system and adapted it to include context for future readers.
He transfers only the strongest highlights after a cooling period, then stacks 8–12 cards to surface themes.

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ADVICE

Write Notes For An Ignorant Stranger

When making notes, write them so a stranger understands them later.
Add a sentence of context around quotes or anecdotes so future-you can use them immediately.

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AI as a Tool; Taste Still Matters

00:48 • 3min

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Has AI Improved at 'Taste'?

03:46 • 4min

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Billy's Note-Card Research System

08:05 • 5min

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Stacking Cards Until a Theme Emerges

12:48 • 27sec

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Where AI Fits in Reading and Research

13:15 • 2min

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Joy of Making Connections Yourself

15:09 • 1min

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Finding Sources Outside AI's Training Data

16:16 • 34sec

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Turning Note-Cards into a Newsletter

16:50 • 3min

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Using Personal Stories and Notes to Write

19:32 • 1min

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Creative Fears: Will AI Replace Research?

20:39 • 3min

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Prompt Skill Reflects Deep Knowledge

23:26 • 59sec

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Cultivating Yourself to Use AI Well

24:25 • 4min

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AI Collapses Time — But Slow Work Builds Taste

28:05 • 8min

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Neck-Down Work: Do the Tedium

36:20 • 7min

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Using AI to Explain Obscure References

43:15 • 3min

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Translating a Theme Into a Newsletter

45:53 • 4min

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AI for Generating Relatable Examples

50:12 • 2min

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AI as Tutor: Explaining Foundational Concepts

52:10 • 5min

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AI for Transcription and Editing Variants

57:21 • 5min

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Is Using AI 'Cheating'?

01:02:42 • 4min

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How Billy Relates to AI: Thought Partner

01:06:59 • 2min

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What AI Might Never Fully Replace

01:08:33 • 1min

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Prediction: People Will Build Deep Knowledge

01:09:50 • 1min

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Key Question: Is AI Actually Good or Just Fast?

01:11:01 • 13sec

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Books Over AI: Billy's Reading Recommendations

• Mentioned in 16 episodes

Make Something Wonderful

Steve Jobs in his own words

Leslie Berlin

Steve Jobs

This book is a chronological compilation of Steve Jobs' words from the beginning of his career to the end of his life. It includes his perspectives on his childhood, his time at Apple, Pixar, and NeXT, and his return to Apple. Edited by Leslie Berlin and featuring an introduction by Laurene Powell Jobs, the book is designed to inspire readers to create their own 'wonderful somethings' that move the world forward. It highlights Jobs' inner thoughts, philosophies, and mantras, showcasing his desire to give back his knowledge and nurture younger people.

#673

• Mentioned in 38 episodes

Little Women

Louisa May Alcott

Written by Louisa May Alcott, 'Little Women' is a semi-autobiographical novel that details the lives of the March sisters in 1860s Massachusetts. The story is loosely based on Alcott's own childhood and that of her three sisters. It explores themes of domesticity, work, and true love, and is known for its portrayal of the sisters' distinct personalities and their struggles with societal expectations. The novel follows their experiences with poverty, illness, and personal growth, and it has been praised for its realistic and empathetic depiction of family life and the challenges faced by women during that era.

• Mentioned in 900 episodes

Meditations

Marcus Aurelius

Meditations is a series of private writings composed by Marcus Aurelius, one of Rome's greatest emperors, as he struggled to understand himself and make sense of the universe. Written between 170 and 180 CE while on military campaigns, this work combines Stoic philosophy with personal observations on leadership, duty, mortality, and human nature. Through twelve books of intimate thoughts never intended for publication, Marcus Aurelius explores themes of self-improvement, resilience in the face of adversity, and living virtuously while accepting what cannot be changed.

#708

• Mentioned in 36 episodes

Critique of pure reason

Immanuel Kant

Immanuel Kant's "Critique of Pure Reason" is a monumental work in philosophy that revolutionized epistemology and metaphysics. It explores the limits of human reason and the conditions under which knowledge is possible. Kant argues that our experience is shaped by inherent structures of the mind, known as categories of understanding. The book delves into the nature of space, time, and causality, and how these concepts structure our perception of the world. Its influence on subsequent philosophical thought is immeasurable, shaping debates on knowledge, morality, and the nature of reality.

#24387

• Mentioned in 2 episodes

Constellations

Sinéad Gleeson

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

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

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