Billy Oppenheimer writes the Six at 6 newsletter, and has been a writing and research assistant for Ryan Holiday, Robert Greene, and Rick Rubin. We talk about research, naive optimism, working for legendary writers and creatives, boredom, his newsletter, curation and creation, how “the work is the win”, and his first book.

— (00:52) Naive optimism & turning what you're already doing into a job (03:31) Researching is where he gets his dopamine (05:30) Combine timeless works with popular ones; triangulate stories (10:48) His note taking system (adapted from Ryan Holiday & Robert Greene) (15:19) The evolution of Six at 6; finding your niche & learning the wrong lessons from role models (23:10) Reading to find excerpts (26:01) Curation & creation (31:03) Seeing a mirror in others’ ideas (34:10) Living in the present (37:26) Combining a known and unknown (39:34) Six at 6 themes: deconstructing creativity & putting in the work (43:06) Balancing the art & audience feedback (45:15) Don't “step into the character” (50:02) Taking the next step & writing his first book (55:45) The work is the win (58:13) Fear of not finding the right stories & concepts (01:00:02) Working with Rick Rubin (01:07:34) Orson Welles & ignorance; Paul Graham & not putting up with BS; authenticity (01:13:24) Qualities of a good research & writing assistant; get excited by what others find boring (01:20:50) Doing it because it’s a compulsion (01:24:10) Find your boredom dopamine

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Billy’s Twitter: https://twitter.com/bpoppenheimer

Six at 6: https://billyoppenheimer.com/newsletter/

Spencer’s Twitter: https://twitter.com/SP1NS1R

Spencer’s Blog: https://spencerkier.substack.com