Podcast Summary: The Daily Stoic

Episode: Bert Kreischer's Reading List (From Ryan Holiday)

Date: February 8, 2026
Host: Ryan Holiday (with guest Bert Kreischer)

Overview

This episode centers on a lively, insightful conversation between Ryan Holiday and comedian Bert Kreischer as they explore Bert’s reading habits, trade memorable book recommendations, and discuss the intersection of literature and life wisdom. The exchange unfolds in the cozy setting of Ryan’s bookstore in Bastrop, Texas, with the pair sharing stories, opinions, and anecdotes about favorite (and misunderstood) works, the power of journaling, and the quirks of reading as adults.

Key Discussion Points & Insights

1. Picking a Reading List for Bert Kreischer

• Ryan reflects on the challenge of curating book recommendations for Bert:

  “When Bert Kreischer asks you for some book recommendations, you really got to think about what he's gonna like.” (02:33, Ryan Holiday)

• A playful banter ensues over notable classics, especially F. Scott Fitzgerald and Hemingway, with references to both the content and backstories behind these figures and their works.

2. Literary Anecdotes & Memorable Lines

• The conversation begins with Bert recalling his favorite line from The Great Gatsby:

  “Nick Carraway says, at the age of 30, I realized I had to stop lying to myself. It's my favorite line.” (03:01, Bert Kreischer)

• Ryan, in turn, highlights the book’s opening wisdom:

  “My favorite line from the Gatsby is actually the first line ... ‘Whenever you feel like criticizing anyone, just remember that all the people in the world haven't had the advantages you’ve had.’” (03:27, Ryan Holiday)

• Bert wittily reacts to Fitzgerald’s early examination of privilege:

  “He's written about white privilege in 1929.” (03:56, Bert Kreischer)

3. Hemingway, Fitzgerald, and Famous Feuds

• The duo delves into the Hemingway/Fitzgerald relationship, told with comedic flair:

  “Zelda ... tells Fitzgerald that his dick is small. And he’s really broken up ... goes to Hemingway and tells him ... Hemingway's like, let me see it ... He shows him, he's like, dude, what are you talking about?” (04:13-04:41, Ryan Holiday)

• Bert on titles:

  “I always say the best titles for any book are Hemingway, and the best titles for any movies are the Grateful Dead.” (04:48, Bert Kreischer)

• They mention the odd history of titles, even noting every phrase of the Gettysburg Address has become a book title (05:05, Ryan Holiday).

4. Misunderstood Classics & Reinterpretation

• Bert admits The Fountainhead baffled him in college, but its hero has grown on him with age:

  “I didn't understand in college, now I'm starting to ... The hero's Keating. He's doing the job ... and then I start going, a roar is the ... oh, shit.” (06:07-06:23, Bert Kreischer)

• Ryan stresses the importance of revisiting books at different life stages:

  “Some of these books, you have to read over the course of your life.” (06:36, Ryan Holiday)

5. New Recommendations and Stories Behind Them

• Ryan proposes A Confederacy of Dunces, lauding it as “the funniest book of all time.” (06:49, Ryan Holiday)

• He recounts the tragic backstory of its author, John Kennedy Toole, and the novel’s posthumous Pulitzer:

  “The one that his editor said wasn’t a good book, the one that his agent said wasn’t a good book wins the Pulitzer Prize.” (08:42-08:53, Ryan Holiday)

• Philosophical takeaway:

  “Do you think it’s good? Do what you want to do ... Does that mean it's going to be a success? You don't know.” (08:58, Ryan Holiday)

• Bert’s response:

  “I can’t wait. I absolutely can’t wait.” (09:05, Bert Kreischer)

6. Heavy Tomes & Making Reading Accessible

• Bert mentions historical epics he’s attempting, e.g., The Fatal Shore:

  “It’s so hard to get into ... do we have to read the preface if you want to understand what's happening?” (09:32-09:37, Bert Kreischer)

• Ryan offers realistic advice and lighter alternatives, and recommends patience with dense books.

7. Reflections on Formative Reads

• Bert reflects on Fear and Loathing in Las Vegas and his journey into reading for pleasure:

  “He was my first book I ever sat and read. For real. Like, not like I had to read in class, but I sat and read a book, was The Firm. And then the next one was Fear and Loathing.” (13:21-13:27, Bert Kreischer)

• The conversation branches into James Michener, Empire of the Summer Moon, and even McConaughey’s Greenlights.

8. The Power & Practice of Journaling

• Ryan introduces a “one line a day” journal, explaining its accountability and reflective power:

  “Every day for 10 years, I write one thing. So it's really, really cool because I can go through it ... you can kind of see the rhythms of your life.” (16:49-17:16, Ryan Holiday)

• Bert lights up at the idea and plans to give it to his daughter:

  “This is perfect ... I'm going to be a better parent this year considering my daughters watch my TV show about them come out.” (17:51-17:59, Bert Kreischer)

• The discussion ends with honest reflections on parenting, public life, and holding onto personal traditions.

Notable Quotes & Memorable Moments

On Friendship and Honesty:

“So he goes to Hemingway and he tells [him] that she said this and ... then Hemingway's like, let me see it. He shows him. He's like, dude, what are you talking about?”
— Ryan Holiday (04:27)

On Failing, Perseverance, and Art:

“The one that his editor said wasn’t a good book, the one that his agent said wasn’t a good book wins the Pulitzer Prize.”
— Ryan Holiday (08:53)

On Self-Reflection:

“At the age of 30, I realized I had to stop lying to myself.”
— Bert Kreischer quoting The Great Gatsby (03:01)

On Re-reading and Understanding:

“Some of these books you have to read over the course of your life.”
— Ryan Holiday (06:36)

On Parenting and Legacy:

“Every day for 10 years, I write one thing ... you can kind of see the rhythms of your life ... Oh, that was exactly a year ago.”
— Ryan Holiday (16:55-17:16)

Book Recommendations Shared

1. The Great Gatsby – F. Scott Fitzgerald
2. The Crack-Up – F. Scott Fitzgerald
3. The Fountainhead – Ayn Rand
4. A Confederacy of Dunces – John Kennedy Toole
5. The Fatal Shore – Robert Hughes
6. The Moviegoer – Walker Percy
7. Endurance – Alfred Lansing
8. Greenlights – Matthew McConaughey
9. Sports books by Wright Thompson
10. Empire of the Summer Moon – S.C. Gwynne
11. One Line a Day journal

Important Timestamps

• 02:33 – Beginning of book recommendation talk; banter about Fitzgerald, Gatsby’s best line
• 04:13 – Hemingway/Fitzgerald humorous anecdote about their friendship
• 06:07 – Bert on not "getting" The Fountainhead in college
• 06:49–09:05 – Story behind A Confederacy of Dunces
• 09:32 – Bert struggles with The Fatal Shore
• 13:21–13:40 – Bert on his formative reading experiences
• 15:39 – Bookstore and community discussion
• 16:28 – Journaling practice and its impact
• 17:51 – Passing journaling tradition to his daughter

Tone & Style

The episode is casual, witty, deeply personal, and often irreverent—true to both Kreischer’s comedic voice and Holiday’s earnest, reflective style. The banter mixes literary history, bookish advice, and real-life vulnerability, making the conversation both amusing and meaningful.

For anyone looking for reading inspiration, encouragement to revisit old books with new eyes, or motivation to start a reflective habit like journaling, this is a rich, entertaining listen.