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
