The Brian D. O'Leary Show

THE FIRST ALL-STAR GAME with author Randall Sullivan

What happens when a botched assassination attempt on a president, the “Outfit,” the Great Depression, and the Legend of Babe Ruth collide in Chicago?

Author Randall Sullivan reveals how the first so-called “Game of the Century” helped pull America out of its darkest era. Discover the untold history of baseball’s first All-Star Game and the legends that shaped the sport.

In 1933, an assassin fired six bullets at President-elect Franklin D. Roosevelt in Miami. Every single bullet missed FDR, but they fatally struck Chicago Mayor Anton Cerm...

Episode Summary

On this episode of The Brian D. O’Leary Show, Brian sits down with David Nugent, co-founder and CEO of Next League, a technology advisory and solutions provider exclusively servicing the sports industry.

Dave's latest book is THE BUSINESS OF SPORTS TECHNOLOGY: How to Make Smart Decisions That Drive Your Organization Forward (Sports Business Journal Publishing, April 14, 2026)

They discuss the philosophical shifts behind tech deployment, how artificial intelligence is streamlining sports operations, and the cultural decisions that drive how leagues interact with their fans.

From the evolving landscape of re...

Soccer is the world’s most popular sport, yet its origins are shrouded in chaos, and its modern “analytics” are often flawed.

⚽ HOW TO WATCH SOCCER LIKE A GENIUS (Abrams Press, May 12, 2026) by Nick Greene https://amzn.to/4eVb8ve ⚽

Author Nick Greene joins The Brian D. O’Leary Show to dismantle everything you thought you knew about “the beautiful game”. Using insights from architects, stuntwomen, paleoanthropologists, and computer scientists, we tear into the history of soccer’s bizarre early rules and expose why American youth player development is fundamentally broken.

Timed with the World Cup comi...

Mark Kurlansky on The Dying Art of Catching Real Fish

Guest: Mark Kurlansky

We had the great fortune to sit down with Mark Kurlansky, the man who wrote the definitive book on Cod, to discuss his latest release: TO CATCH A FISH (Storey Publishing, March 31, 2026).

The Hollywood elite want you to believe fly fishing is a ballet of endless shadow casting. We tear that myth apart. We discuss the reality behind the movie A River Runs Through It. The beautiful, looping casts you see on screen will leave you tangled in a mess...

Guest: Keith O'Brien, author of HEARTLAND: A Forgotten Place, an Impossible Dream, and The Miracle of Larry Bird by Keith O'Brien (Atria Books, March 3, 2026) https://amzn.to/47ghvEE

Podcast Release Date: March 7, 2026

Episode Length: 42 minutes

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EPISODE DESCRIPTION:

Larry Bird is one of basketball's all-time greats, but there's a chapter of his story that's rarely told. Between 1974 and 1979, from his brief time at Indiana University through his magical season at Indiana State, Bird nearly walked away from basketball entirely.

In this episode, Brian O'Leary sits down with journalist...

Guest: Keith O'Brien, author of HEARTLAND: A Forgotten Place, an Impossible Dream, and The Miracle of Larry Bird by Keith O'Brien (Atria Books, March 3, 2026) https://amzn.to/47ghvEE

Podcast Release Date: March 7, 2026

Episode Length: 42 minutes

EPISODE DESCRIPTION:

Larry Bird is one of basketball's all-time greats, but there's a chapter of his story that's rarely told. Between 1974 and 1979, from his brief time at Indiana University through his magical season at Indiana State, Bird nearly walked away from basketball entirely.

In this episode, Brian O'Leary sits down with journalist and New...

Brian O’Leary interviews author Monte Burke about his book MEN OF TROY: The Epic Afternoons, Wild Nights, and Enduring Legacy of Pete Carroll’s USC Trojans (Grand Central Publishing, published January 13, 2026).

Burke traces his own path into college football and writing, contrasts the atmosphere of college football with the NFL, and explains why coaches like Carroll and Nick Saban make compelling subjects.

We discuss USC’s unique Los Angeles moment with celebrity-laced practices, the program’s rise under Carroll, and how the Reggie Bush scandal exposed flaws in college football’s amateurism model and helped for...

In the latest episode of The Brian D. O’Leary show, we sat down with Yaron Weitzman in a wide-ranging interview that dove into the modern Lakers dynasty, the lasting imprint of the Buss family, and the evolving career of LeBron James.

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Featured Guest

Yaron Weitzman: Author, NBA journalist, and insider on all things basketball, discussing his new Lakers book and the deeper drama surrounding LeBron, the Buss family, and team culture.

Find Yaron on social media:

· X/Twitter (@YaronWeitzman)

· Instagram (@yaronweitzman)

· TikTok (@yaron...

Ken Belson on How Jerry Jones, Robert Kraft, and Roger Goodell Built the NFL's $10 Billion Empire

EPISODE OVERVIEW

In this compelling deep-dive conversation, Brian D. O'Leary sits down with Ken Belson, New York Times sportswriter and author of the Amazon #1 Bestseller Every Day Is Sunday: How Jerry Jones, Robert Kraft, and Roger Goodell Turned the NFL into a Cultural and Economic Juggernaut (Grand Central Publishing, October 14, 2025).

This wide-ranging interview explores the transformation of the NFL from a beloved sporting league into a ten-billion-dollar cultural phenomenon. Belson reveals the untold stories behind the three...

BASEBALL IN THE ROARING TWENTIES: The Yankees, the Cardinals, and the Captivating 1926 Season by Thomas Wolf (University of Nebraska Press, September 1, 2025)

Quick recap

The discussion between Brian and Tom Wolf centered on Wolf's new book about the 1926 baseball season, which explored notable players like Babe Ruth and the competitive dynamics between teams that year. The conversation delved into the broader sports landscape of the 1920s, including the rise of different sports and the challenges faced by black baseball players during this era. The discussion concluded with an examination of key figures in baseball history, including...

In the latest episode of the Brian D. O'Leary Show, Jim Murphy, the author of the bestselling book INNER EXCELLENCE: Train Your Mind for Extraordinary Performance in the Best Possible Life, discusses the widespread impact and philosophy behind his work. Highlighting how NFL star AJ Brown benefited from Inner Excellence's teachings during critical games, Murphy elaborates on the book's core system that promotes being fully present and mastering self for extraordinary performance. He compares his concepts to those popularized by James Clear in Atomic Habits, emphasizing the importance of redefining success and learning from perceived failures. Murphy draws from...

After a long delay in production … Brian hosts Scott Fischbuch, a Jungian Typology expert, for an in-depth conversation on personality types and his methods. Scott explains his approach to personality typing, which involves analyzing preferences in conversation, turns of phrase, and behavioral mannerisms.

Brian shares his journey into podcasting and reflects on how his personality type has evolved. Scott identifies Brian's personality type as ISTJ and explains the significance of introverted sensing and extraverted intuition.

They discuss the impact of cultural influences on personality and the importance of effort and team dynamics in professional and pe...

Website re-launch: https://briandoleary.com

Los Gatos Review (quarterly magazine): https://losgatosreview.com

The O'Leary Letter: http://OLearyLetter.com

O'Leary's Laws

O'Leary's First Law: Nice is not a virtue.

O'Leary's Second Law: You can't cast yourself out of a tangle.

O'Leary's Third Law: While apologies are often necessary or appropriate, never should you have to explain yourself, particularly for something you believe and are not sorry for.

Column at Substack: https://briandoleary.substack.com/p/theyre-now-calling-it-discourse

For our regular emails: https://briandoleary.com/letter

Find us on 𝕏-Twitter : https://x.com/BrianDOLeary

This column on 𝕏-Twitter : https://x.com/BrianDOLeary/status/1814045579301019731

Text of article follows:

They're now calling it 'discourse' What happened to disinformation?

By now, you've probably seen a host of graphics in the swampwaters of social media, hastily cobbled together by run-of-the-mill milquetoast leftists. Virtue-signalers, viz.

A meme gone viral over the last few days is a checklist that attempts to pac...

BrianDOLeary.com

Straight to the email list + our FREE Time Management checklist : BrianDOLeary.com/letter

O'Leary's First Law: Nice is not a virtue.

O'Leary's Inner Sphere : http://OLearyInnerSphere.com

The Vintage Mencken (gathered by Alistair Cooke)

“As an Amazon Associate, I earn from qualifying purchases.”

Since we tend to “Serious Content Amidst an Unserious Culture,” we don’t believe in linking to anything that isn’t worthwhile. We believe in our mission here and we’re in the business of keeping our website, emails, and podcasts going. Affiliate comm...

The first and perhaps only presidential debate happened on June 27. Adam Haman and Brian O'Leary have the definitive smackdown of the whole thing.

The fellows awarded a winner and offered some commentary. Hilarity ensues (though not necessarily intentional - it's a factor of who was "debating.")

Adam Haman - https://hamannature.substack.com/

Brian O'Leary - https://briandoleary.com/

O'Leary's FREE e-book Run at Thunder, Vol. 1 - https://runatthunder.com/

Natural Order - https://naturalorderpodcast.com/

Links:

https://briandoleary.com/ep98

https://briandoleary.com/ep97

Links:

Links:

https://briandoleary.com/ep95

Links:

The Brian D. O’Leary Show

January 27, 2024

Wesley Schlemmer – Bitcoin Bay Ep. 94

Wesley Schlemmer is a leading bitcoin (₿) evangelist and educator in the Tampa Bay region. One of the goals of his 501c3 organization — Bitcoin Bay — is to create a circular economy with bitcoin at the center of it all. We had Wesley on the show a few months back to talk about “taking the orange pill.”

Wesley is a born-and-raised “Florida Man” who is working to Make America Florida.

Links and topics mentioned: Bitcoin Bay

· https://www.bitcoinbay.live...

The Brian D. O’Leary Show

December 5, 2023

Jason Purcell – The petrodollar system (Part 2) Ep. 93

Check us out on Substack: https://open.substack.com/pub/briandoleary/p/jason-purcell-the-petrodollar-system?r=3c44f&utm_campaign=post&utm_medium=web

We welcome financial analyst Jason Purcell on the program for the second part in a series on the history of money and banking. We’re talking about the “petrodollar” once again.

Jason is working on a book on the topic which includes a chapter about his theory of the “Petrodollar System.” You can find the first...

The Brian D. O’Leary Show

December 4, 2023

Matthew Sercely – Agorist Tax Advisor Ep. 92

Matthew Sercely has been a licensed attorney since 2009, and in 2020 he founded his own company to provide tax advice and planning for small businesses.

He is dedicated to helping entrepreneurs, solopreneurs, and side-hustlers by setting up their businesses to legally avoid as much tax as possible.

While he exclusively works with those who have or are starting businesses, Matthew’s weekly newsletter offers general advice that anyone can use.

When he's not screwing with the go...

The Brian D. O’Leary Show

November 29, 2023

We welcome financial analyst Jason Purcell on the program for the first part of what we hope to be a series on the history of money and banking.

Jason is working on a book on the topic which includes a chapter about his theory of the “Petrodollar System.” In this first part of our series, Jason gives us a background on the history leading up to the idea of the “petrodollar” phenomenon.

Jason will be on the show again soon to complete his analysis of the pet...

The Brian D. O’Leary Show

October 12, 2023

Try as I may, I still can’t shake not being a sports narrowcaster. The topic still comes up.

At some point, I have to accept that it is part of who I am.

An interesting thing came up today when I was listening to a podcast that my friend and Natural Order Podcast co-host Adam Haman was on. They mentioned a “Deep Thought” from Jack Handey.

That got my wheels spinning, and thus this podcast.

Links on topics mentioned are belo...

The Brian D. O’Leary Show

September 15, 2023

Show notes available: https://open.substack.com/pub/briandoleary/p/on-culture-through-the-lens-of-boston?r=3c44f&utm_campaign=post&utm_medium=web

The O’Leary Letter

https://briandoleary.com/letter/

Brian O’Leary on Twitter/𝕏

https://twitter.com/BrianDOLeary

Baseball

Boston Red Sox

Roger Clemens

Dan Duquette … blech!

Red Sox announce Bloom’s exit: ‘We’re here to win’

College Football

Boston College Football

The Red Bandana Game

The Brian D. O’Leary Show

September 12, 2023

Show notes available: https://open.substack.com/pub/briandoleary/p/on-coach-prime-the-nfl-mlb-and-college?r=3c44f&utm_campaign=post&utm_medium=web

The O’Leary Letter

https://briandoleary.com/letter/

Brian O’Leary on Twitter/𝕏

https://twitter.com/BrianDOLeary

New York Jets

NewYorkJets.com

Hard Knocks (TV Show)

Wisconsin bar runs promo: customers drink free if Jets lose. Hilarity ensues.

Baseball

Fantastic new rules from Major League Baseball turning game into a tr...

The Brian D. O’Leary Show

August 17, 2023

Show notes available: https://open.substack.com/pub/briandoleary/p/things-ive-been-marinating-on-for?utm_campaign=post&utm_medium=web

The O’Leary Letter

https://briandoleary.com/letter/

The Brion McClanahan Show

https://www.brionmcclanahan.com/

A must listen-to podcast.

Rich Men North of Richmond – Oliver Anthony Twitter (X?) account

https://twitter.com/AintGottaDollar

Viral song with soul.

The Arena Football League

https://www.afl2024.com/

I’m thinking of how t...

The Brian D. O’Leary Show

June 30, 2023

Show notes available: https://briandoleary.substack.com/p/once-more-with-feeling-on-the-great?sd=pf

In yesterday's email, we wrote about the great Kris Kristofferson. If you didn’t get the email and want to read it, reply to this email and we will send it to you.

Kristofferson

Kris Kristofferson: An outlaw at 80

Kristoffer Kristofferson, Sports Illustrated, March 31, 1958

Moonlight Graham Show

https://www.moonlightgrahamshow.com/

Host is Tim Flattery & I was a recently a guest on his brot...

The Brian D. O’Leary Show

June 23, 2023

Show notes available: https://briandoleary.substack.com/p/control-the-controllables?sd=pf

Daily 3

1. Don’t take criticism from someone you wouldn’t take advice from.

2. The hardest battle you will fight is living in a world where—every single day—someone is trying to make you be someone you don’t want to be.

3. Control the Controllables. It’s not “don’t worry about things outside our control…” Take initiative.

o What can you control?

§ Our words

§ Our routine

The Brian D. O’Leary Show

June 21, 2023

Show notes available: https://briandoleary.substack.com/p/some-philosophy-a-little-windbaggery?sd=pf

Daily 3

1. Discipline: If you’re offering excuses for your behavior, don’t accept the offer.

2. Boundaries: Define your own. Don’t let others define your own boundaries.

3. “I make myself rich by making my wants few.” ~Thoreau. Just marinate on this thought and see if it makes sense or if it is mere blowhardiness. I find it a mixture.

The Reformed Financial Advisor Podcast

I was a guest...

The Brian D. O’Leary Show

June 15, 2023

Show notes available: https://open.substack.com/pub/briandoleary/p/a-fresh-take-on-american-politics?r=3c44f&utm_campaign=post&utm_medium=web

Best-selling author, podcaster, and YouTuber Taylor Marshall was on the Crisis Point podcast with host Eric Sammons a few weeks ago. Marshall announced his intent to run for President of the United States.

While I don’t endorse anyone, I support the candidacy of Dr. Marshall. He’s a “dad with a webcam,” but more importantly has a vision for America that no political figure has...

The Brian D. O’Leary Show

June 14, 2023

Show notes available: https://briandoleary.substack.com/p/eliminate-the-drama-daily-action?sd=pf

The Daily 3 – 6/14/2023

1. How you see your life is more important than how it looks to outsiders

2. “Culture” is happening regardless. Eliminate the drama. Focus on The Process

3. DAILY ACTION. Consistency over proficiency. Ruthless organization. Every day…whatever it takes.

Fountain.FM

Listen and support us at the same time over at Fountain.FM

Natural Order Podcast

https://naturalorderpodcast.com/ep9/

Liquid I...

The Brian D. O’Leary Show

June 9, 2023

Show notes available: https://briandoleary.substack.com/p/dont-do-what-everybody-else-does?sd=pf

The Daily 3 – 6/9/2023

1. You don’t have to follow trends. In other words, “don’t do what everybody else is doing.”

2. Stop rushing the process.

3. You’ve got this!

Fountain.FM

Listen and support us at the same time over at Fountain.FM

Natural Order Podcast

https://naturalorderpodcast.com/ep9/

O’Leary & Company

O’Leary says, “I’ve never really failed, b...

The Brian D. O’Leary Show

June 1, 2023

Show notes available: https://briandoleary.substack.com/p/giving-away-value-versus-being-valuable?sd=pf

Brian D. O’Leary dot com

Have a plan. Be Aggressive. Exhibit Character.

Natural Order Podcast

We are past our initial launch sequence. Please head over to our website to get on our email list and be alerted when we drop new episodes.

Latest episode: https://naturalorderpodcast.com/ep9/

OLearyMaverick.com

Get the best pricing on the all-new Marketing Maverick program which will revo...

The Brian D. O’Leary Show

May 31, 2023

Show notes available: https://briandoleary.substack.com/p/on-virtue-the-role-player-and-internet?sd=pf

The only true source of politeness is consideration—that vigilant moral sense which never loses sight of the rights, the claims, and the sensibilities of others. This is the one quality, over all others, necessary to make a gentleman.

William Gilmore Simms (1806-1870)

"The pessimist complains about the wind. The optimist expects it to change. The realist trims his sails.”

Author unknown

Brian D. O’Leary dot com

The Brian D. O’Leary Show

May 26, 2023

Show Notes available: https://briandoleary.substack.com/p/in-the-game-of-life-i-want-you-on?sd=pf

The Daily 3 (5/26/23)

· Service to others should be a personal calling.

· Self-Discipline: living in harmony with your goals and values.

· Consider strategy in every step you take in life.

Bill Walsh – Football Coach

https://briandoleary.com/walsh/

His coaching philosophy focused on developing a strong system and culture rather than relying solely on individual talent. Walsh believed in empowering players and coaches to work togethe...

The Brian D. O’Leary Show

May 24, 2023

Show Notes available: https://briandoleary.substack.com/p/we-deserve-apologies-were-never-going?sd=pf

Freedom?

Today we talked about some bigger concepts. What rights do we have …. Really?

What is freedom? Do people “deserve” it?

Does freedom come at a cost? Indeed, it does. Most of us, likely myself included, aren’t paying for it.

Libertinism

A libertine is a person devoid of most moral principles, a sense of responsibility, which they see as unnecessary or undesirable, and is especially...

The Brian D. O’Leary Show

May 19, 2023

Show notes available: https://briandoleary.substack.com/p/bitcoin-maximalists-preparation-meets?sd=pf

Fountain.FM

Listen and support us at the same time over at Fountain.FM

O’Leary’s Bitcoin Page

https://briandoleary.com/bitcoin/

“Taking the Orange Pill”

The O’Leary Review Podcast w/ Wesley Schlemmer – Ep 18

Natural Order Podcast

https://naturalorderpodcast.com/ep7/

National Divorce?

Today, we address the growing conversation regarding “National Divorce” in America.

What holds the U...

The Brian D. O’Leary Show

May 17, 2023

Show notes available: https://briandoleary.substack.com/p/open-mind-no-way-shut-it-on-something?sd=pf

Brian D. O’Leary dot com

Have a plan. Be Aggressive. Exhibit Character.

Natural Order Podcast

We are excited about the launch of our new show. The support has been amazing so far. Please head over to our website there to get on our email list and be alerted when we drop new episodes.

Three main points from yesterday’s show