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Infinite Loops


May 16, 2023

Dylan O’Sullivan is a writer and media specialist based in Cork, Ireland.

Dylan’s work has been published in magazines such as The Spectator and Areo. He is also the creator of Essayful, a Substack dedicated to becoming “a new home for writing.”

Following his participation in David Perell’s Write of Passage course last year, Dylan joined us as an intern at O’Shaughnessy Ventures.

He joins the show to discuss the problem with traditional education, the blurry border between fiction & nonfiction, how AI is going to impact writing, why Ireland has such cultural influence, and more!

Important Links:
Show Notes:
  • Losing the O’s
  • The collapse of the old institutions
  • An introduction to Essayful
  • "There's nothing new under the sun.”
  • The blurry border between fiction & nonfiction
  • Rebuilding the Tower of Babel
  • A book as a living thing
  • How is AI going to impact writing?
  • Why Dylan took Write of Passage
  • Why are academic papers so hard to read?
  • Why does Ireland have such cultural influence?
  • What’s next?
  • More!
Books Mentioned:
  • Old God’s Time; by Sebastian Barry
  • Unflattening; by Nick Sousanis
  • The Island of Saints and Scholars; Sean McMahon
  • Ulysses; by James Joyce