The Daily Stoic

Bert Kreischer's Reading List (From Ryan Holiday)

24 snips
Feb 8, 2026
Bert Kreischer, comedian and podcaster known for loud storytelling and comedy specials, explores a stack of books and his changing takes on classics. Short conversations jump from Fitzgerald and Hemingway to Confederacy of Dunces and The Fountainhead. They discuss what sparked his reading habit and practical rituals like journaling and strength training.
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ADVICE

Curate Books For The Person

  • When recommending books, tailor choices to the person's tastes and life stage.
  • Ryan curated a short stack for Bert to read across his life rather than a generic list.
ANECDOTE

Fitzgerald Conversation And The Crack-Up

  • Ryan gave Bert The Crack-Up and discussed Fitzgerald's life and themes.
  • Bert connected to Fitzgerald through favorite lines and memories of reading Gatsby.
INSIGHT

Annotated Editions Change Understanding

  • The new annotated 100th anniversary edition of The Great Gatsby reveals historical context and facts.
  • Such editions can change how readers understand and appreciate a century-old classic.
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