Dylan O’Sullivan is a curator, editor, and writer at O'Shaughnessy Ventures and Essayful. Dylan and I talk about writing, taste, discipline vs. inspiration, timelessness vs ephemerality, boredom and solitude vs. the internet, inciting a digital renaissance, not lying to yourself, and more.

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(00:45) Curating & editing vs. writing

(05:39) Fear of never writing quality work or living up to your idols

(08:32) Discipline vs. inspiration

(15:49) Balancing technology & ephemerality with the timeless

(17:44) Solitude, getting better at the craft, and having a "normal" life

(21:09) Boredom

(26:32) Short attention & the effect on art & mediums

(29:54) Lack of original works & risk taking

(36:43) Digital renaissance; timeless stories & works

(44:15) What is timeless & what will become timeless

(48:17) Creativity & the subconscious

(52:08) Long form writing vs memes

(55:00) Above all, don't lie to yourself

(01:00:29) Books he’d have in his bookstore window

(01:03:38) Three favorite directors & their three movies

(01:05:34) Final question for listeners

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Dylan’s Twitter: https://twitter.com/DylanoA4

Essayful: https://www.essayful.co/

O'Shaughnessy Ventures: https://www.osv.llc/

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

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