Summary of Bert Kreischer's Reading List (From Ryan Holiday)

Overview of Daily Stoic Podcast — Bert Kreischer's Reading List

This episode features a casual conversation between Ryan Holiday (host, bookstore owner) and comedian Bert Kreischer where Ryan recommends a stack of books tailored to Bert’s tastes. The discussion mixes book recommendations, literary anecdotes (Fitzgerald/Hemingway, John Kennedy Toole), reading advice for different life stages, and practical habits (journaling). The episode also includes several sponsor spots (Tonal, Whole Foods, Helix, BetterHelp).

Key books mentioned (what they are and why they were recommended)

• The Crack-Up (F. Scott Fitzgerald) — A collection of Fitzgerald’s essays; recommended alongside context about Fitzgerald’s life and vulnerabilities.
• The Great Gatsby (new 100th‑anniversary / public domain edition) — Ryan highlights the opening lines and the annotated/illustrated edition that adds historical/contextual notes.
• A Confederacy of Dunces (John Kennedy Toole) — Called “the funniest book of all time.” Ryan tells the famous, heartbreaking publication story: initial rejections, the author’s suicide, and Walker Percy discovering and getting it published, after which it won a Pulitzer — used as a lesson about unpredictable success.
• The Fountainhead (Ayn Rand) — Discussed as a book some people understand differently at various life stages; Ryan notes that rereading later in life can shift your view of the characters and themes.
• The Fatal Shore (Robert Hughes) — A dense history of the British penal colony system and Australia; praised but noted as a slow, heavy read (preface recommended).
• Endurance (Alfred Lansing) — The Shackleton survival story; Ryan references the origin of the ship’s name motto: “By endurance we conquer.”
• Greenlights (Matthew McConaughey) — Mentioned as enjoyable; Ryan is on the back cover.
• The Moviegoer (Walker Percy) — Referenced as Walker Percy’s notable work (relevant to the Confederacy of Dunces story).
• Other titles mentioned in passing: Fear and Loathing in Las Vegas (Hunter S. Thompson), The Prophet (Kahlil Gibran), Hell’s Angels (Hunter S. Thompson), Empire of the Summer Moon (S.C. Gwynne), and a sports book by Wright Thompson (recommendation for sports writing fans).

Notable anecdotes & insights

• Fitzgerald/Hemingway friendship: Ryan recounts stories about Fitzgerald’s troubled marriage to Zelda, Hemingway’s bluntness (including the infamous exchange about Fitzgerald’s insecurity), and an episode where Hemingway’s purported comments wound Fitzgerald — used as a window into literary lives and reputations.
• A Confederacy of Dunces publishing story: The novel’s initial rejections, the author’s tragic death, a mother discovering the manuscript, and Walker Percy championing it — demonstrates how gatekeepers can be wrong and success can be unpredictable.
• Reading evolves: Several books (notably The Fountainhead) read differently at different ages. “Some books you have to read over the course of your life” — meaning insights and sympathies change as you grow.
• Titles as creative fuel: Ryan enjoys inventing titles as a creative exercise (example: his TV show Something’s Burning) and suggests titles can spark projects.
• Practical reading habit: Prefaces and introductions can be important (Ryan tells listeners to read prefaces if they want orientation on heavy books like The Fatal Shore).

Practical recommendations & action items

• Suggested reading order (Bert’s chosen path): Start with A Confederacy of Dunces, then The Crack-Up, then other heavier or longer reads (e.g., The Fatal Shore).
• Keep a one-line-a-day journal: Ryan recommends the “One Line a Day” journal (also a parenting variant) to capture daily rhythms and hold yourself accountable. He practices writing one sentence a day for years and finds it revealing when you compare the same date across years.
• Don’t be deterred by early rejections: The Confederacy of Dunces example is a reminder to trust your judgment and finish what you care about; external opinions aren’t definitive.
• Read some books more than once and at different life stages to get new perspectives.

Short list you can copy (Bert-ready stack)

• A Confederacy of Dunces — John Kennedy Toole
• The Crack-Up / Selected Fitzgerald works — F. Scott Fitzgerald
• The Great Gatsby (annotated/100th-anniversary edition)
• The Fountainhead — Ayn Rand
• The Fatal Shore — Robert Hughes
• Endurance — Alfred Lansing
• Greenlights — Matthew McConaughey
• One Line a Day journal (and parenting version)

Sponsors & offers mentioned (brief)

• Tonal — at-home strength training system (promo code TDS for $200 off).
• Whole Foods — anecdotal mention about grocery shopping and Valentine’s items.
• Helix — mattresses (helixsleep.com/stoic for 27% off).
• BetterHelp — online therapy (betterhelp.com/daily-stoic for 10% off first month).

Bottom line

This episode is a personable, serviceable reading-list conversation mixing serious literary recommendations with light-hearted comedy anecdotes. It’s as much about specific books as it is about reading as a lifelong practice: revisit books, expect tastes to change, keep small daily habits (journaling), and don’t let early rejection define a work’s value.