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Artwork for Old School

Old School with Shilo Brooks

The Free Press
Philosophy
Education
Plato's Republic
The Moviegoer
Vladimir Nabokov
Socrates
Middlemarch
Wolf
Justice
Cornel West
The Adventures Of Pinocchio
Collodi
Walker Percy
Lolita
Pedophilia
Grief
Kierkegaard
Censorship
Democracy
Fatherhood

Fewer of us than ever are reading books for pleasure. Shilo Brooks is on a mission to change that. Old School is a new podcast from The Free Press about great books and how reading them can make us stronger, better men. The show features intimate conversations with fascinating men—from fitness gurus to philosophers—about the books that shaped their lives. New episodes out every Thursday. Read with... more

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Artwork for Old School

Latest Episodes

For tickets to our live recording with Jon Meacham in Philadelphia, click here and register. Use code TFP for a 20 percent discount.

In this episode, Shilo sits down with sportswriter Wright Thompson to explore what the ESPN mainstay has learned fro... more

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.

As he built Kind Snacks into a $5 billion company, ‘Shark Tank’s Daniel Lubetzky didn’t turn to startup gurus or bus... more

Neal Stephenson, the prophetic author of cyberpunk classics like Snow Crash and The Diamond Age, has shaped how we imagine the future, from the metaverse to crypto to AI. His science fiction has a way of becoming reality.

But Stephenson’s thinking i... more

For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.

Life is short. How do we live it well?

Harvard professor Arthur Brooks has spent years studying happiness. In this ... more

Key Facts

Accepts Guests
Accepts Sponsors
Contact Information
Podcast Host
Number of Listeners
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Recent Guests

Daniel Lubetzky
Founder of Kind, Shark Tank participant
Kind
Episode: The Ancient Jewish Wisdom Behind a $5 Billion Company
Neal Stephenson
Legendary science fiction writer
Author
Episode: Neal Stephenson on AI, Rome, and How Civilizations Decline
Arthur Brooks
Professor, author, happiness expert
Harvard University
Episode: The Two Types of People Who Never Find Happiness
Jack Carr
Best-selling author, TV producer, former Navy SEAL sniper
Author of The Terminalist, Savage Son, The Most Dangerous Game discussion guest
Episode: Hunting Humans for Sport
Peter Savodnik
Editor at The Free Press, discussed the Didion classic and its cultural implications
The Free Press
Episode: Joan Didion Knew What Hollywood Would Become
Ben Schatz
Public defender; founder of Books Beyond Bars
Center for Appellate Litigation; Books Beyond Bars
Episode: The NYC Public Defender Who Sends Books to Prisoners
Alex Jones
Founder and CEO of Hallow, a prayer app
Hallow
Episode: ‘The Brothers Karamazov’ Helped Inspire the Catholic App Hallow
Joseph Luzzi
Author and professor with a deep passion for literature and Dante
Episode: Dante: The Most Famous, Least Read Poet
Elliot Ackerman
Best-selling author, Marine Corps veteran, and contributor to The Free Press
Episode: America’s Most Righteous War Produced Its Best Anti-War Novel

Host

Shilo Brooks
Host of Old School; engages in intimate conversations about books that shaped lives; often invites diverse thinkers and writers.

Reviews

4.8 out of 5 stars from 200 ratings
  • Great to see Shilo got his own podcast!

    As a former student of Shilo’s from over a decade ago, I was very excited to hear about this podcast and have been listening from near the start. I love this podcast. It’s so much fun every week. Some of the books (and guests) are truly surprising, and a lot of the interviews go in directions I never expected. Many of the themes and the books/authors are near to my heart.

    Apple Podcasts
    5
    Ben Connelly
    United States25 days ago
  • Full of Depth

    This is the kind of podcast all can get value from. Full of insight and depth on a variety of issues.

    Apple Podcasts
    5
    CMac2834
    United Statesa month ago
  • Outstanding

    My favorite podcast! Love the equanimity, the gentle pressing of guests on their more outlandish opinions, the mutual exploration of topics that matter to the guests and listeners. It continually affects my own reading list. I particularly enjoy the expression of mind relatively unadorned with political garbage from either pole.

    Apple Podcasts
    5
    Machiavelli51
    United States2 months ago
  • You hit the nail on the head

    Regarding the episode about Lolita—you are invoking the concept of Disordered Love when you refer to novel of awful human behavior.

    Apple Podcasts
    5
    Eamon Parker
    United States2 months ago
  • DNC-only Liberal Woke

    Shilo is TX outside, CA inside. Conservatives here are not wanted. Yet another podcast where Liberal politics and pro-Democrat Party worldviews are pushed—in this case through books. BIAS is awful.

    Apple Podcasts
    1
    chubby baker
    United States4 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners praise the show's depth and respectful probing of guests.
Some episodes spark debate or critique around perceived biases in topics or guests.
Audience appreciates non-polemical, thoughtful discussions that connect books to modern life.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#33
United States/Arts/Books
Apple Podcasts
#103
United States/Arts
Apple Podcasts
#249
Canada/Arts/Books
Apple Podcasts
#86
Australia/Arts/Books
Apple Podcasts
#237
Australia/Arts
Apple Podcasts
#68
Denmark/Arts/Books

Talking Points

Recent interactions between the hosts and their guests.

The Ancient Jewish Wisdom Behind a $5 Billion Company
Q: What is the core value you take from Pirkei Avot when making big decisions?
The emphasis on balance, humility, and community responsibility guides his long-term thinking, avoiding short-term greed and encouraging inclusive leadership.
The Ancient Jewish Wisdom Behind a $5 Billion Company
Q: Why do you think Pirkei Avot was transformative for you during a period of loss and transition?
He explains how the maxims grounded him, provided moral clarity, and shaped his approach to leadership, risk, and social impact during a pivotal time for both his family and his business.
The Ancient Jewish Wisdom Behind a $5 Billion Company
Q: Tell me the story of founding your company, Kind.
Lubetzky describes turning grief into purpose after his father's passing, the early failure of previous ventures, and how a culture of transparency and equality helped Kind grow into a high-performing, socially-minded company.
Neal Stephenson on AI, Rome, and How Civilizations Decline
Q: Where is AI going and what is it likely to do to us, if anything?
The guest offers a moderate view: AI will perform certain tasks well but is not an end-of-world threat; the real value lies in maintaining personal cognitive skills and virtues that are exercised when we work through problems without over-reliance on AI.
Hunting Humans for Sport
Q: Take me to the sixth grade, Jack Carr, you're reading this. What are you thinking? What are you feeling? How did it affect you then?
The story spoke to me on a primal level, showing how a simple, stripped-down narrative could reveal deep questions about courage, mortality, and the line between civilization and barbarity; it inspired me to write Savage Son and to explore how these themes echo through later works.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Old School

What is Old School about and what kind of topics does it cover?

Long-form conversations that pair classic books with modern leadership, culture, and technology. Episodes thread literature, philosophy, and history into contemporary issues—ranging from ethics in technology and governance to spirituality and personal transformation—via intimate interviews with authors, thinkers, and practitioners. The format tends to foreground how great works shape beliefs, decisions, and worldviews, with a careful, thoughtful host who invites deep reflection without partisan sensationalism. A notable strength is the seamless mix of literary analysis, personal storytelling, and real-world applications, often featuring guests with diverse intellectual pedigrees and practical expertise. This approach makes it appealing to l... more

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Which podcasts are similar to Old School?

These podcasts share a similar audience with Old School:

1. Conversations with Coleman
2. Breaking History
3. What Really Matters with Walter Russell Mead
4. Uncommon Knowledge
5. Ask Haviv Anything

How many episodes of Old School are there?

Old School launched 7 months ago and published 27 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Old School?

Recent guests on Old School include:

1. Daniel Lubetzky
2. Neal Stephenson
3. Arthur Brooks
4. Jack Carr
5. Peter Savodnik
6. Ben Schatz
7. Alex Jones
8. Joseph Luzzi

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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