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

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.