Gentleman Speculator

Latest Episodes:

The Dad Book Review Jun 25, 2026

Show notes

Brian O’Leary is back on the pod to talk about the dad book. This is the airport nonfiction, narrative history, and adventure bio, etc. The Wall Street Journal just declared this ‘category’ a dying breed. As Dads with books, Brian and I draft our favorite picks.

We talk Charles Manson and the CIA, why a German U-boat off the East Coast makes Shadow Divers impossible to put down, and the case for James Michener (bestseller nobody under fifty remembers). And a lot more.

Brian’s Substack and podcast (the O’Leary Review):

https://olearyreview.com

Gentleman Speculator is from Andrew Flattery at Flattery Wealth Management.

TIMESTAMPS

00:00:00 Nixon on his old man

00:01:00 What a dad book is, and why the Journal called it dying

00:11:00 Books you can actually find at the airport

00:12:00 Chaos, Charles Manson and the CIA

00:18:00 The book your own father gave you, Endurance

00:24:00 Sports, and The Boys in the Boat

00:27:00 The First All-Star Game and the 1932 plot on FDR

00:33:00 Biography, The Wright Brothers

00:39:00 Hidden gems, and the forgotten James Michener

00:46:00 The anti-recommendation, Bernard Cornwell

00:53:00 The GOATs, Shadow Divers and The Sportswriter

00:57:00 What Brian is working on now

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

The Book of Elon Apr 08, 2026

Show notes

Eric Jorgenson is back on the pod to talk about his new book, The Book of Elon, a five-year project distilling Elon Musk’s most useful ideas in his own words. Eric and I talk about why Musk is the greatest living entrepreneur, the recursive logic of ‘stacking S-curves,’ and the case for a generation of builders rather than financiers. Along the way: the 2008 split-the-money story, the toy casting that became the gigapress, and why deleting is harder, and more important, than automating.

Buy the book:

https://www.elonmuskbook.org/

Follow Eric: https://x.com/EricJorgenson

Eric’s Smart Friends podcast:

https://www.ejorgenson.com/

Music: “The Big Ship” by Brian Eno

All opinions expressed by Andrew Flattery and his guests are solely their own and do not reflect the opinions of Flattery Wealth Management, a registered investment advisor. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Flattery Wealth Management may maintain positions in Bitcoin and the securities discussed in this podcast.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

Have Yourself a Home Alone Family Dec 18, 2025

Show notes

I dive into what I’m calling peak America, that is the Peter McAllister (Dad) character from Home Alone. Watching this at age 41 and the movie is now a meditation on what’s worth fighting for. I get into how the McAllister house functions as a ‘castle’ for the kind of multi-generational family life that Johann Kurtz writes about in Leaving a Legacy: Inheritance, Charity, & Thousand-Year Families. I look at how Kevin’s initiation by older brother Buzz embodies what Anthony Esolen describes in No Apologies: Why Civilization Depends on the Strength of Men, a rough-and-tumble world where boys learn to build, explore, and fight. There’s even the church scene with Old Man Marley that delivers a Christmas message. I contrast all of this with the so-called ‘found family’ therapeutic culture that tells you to replace rather than reconcile.

Celebrating the chaos, the legacy, the adventure of family life, and a classic movie for Christmas 2025.

Intro: The Drifters’ “White Christmas”

Credit to the Aaron M. Renn episode Why Families Are Fleeing Cities | Bobby Fijan

Outro: Mel Torme’s “Have Yourself a Merry Little Christmas”

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

Johann Kurtz (Becoming Noble) - Leaving a Legacy Nov 25, 2025

Show notes

I speak with with the semi-pseudonymous Johann Kurtz on his terrific new book Leaving a Legacy: Inheritance, Charity, & Thousand-Year Families. Johann lays out the foundation for why it can be moral to leave an inheritance when pared with virtue. We talk how ‘Die with Zero’ misses the mark, why true charity is necessarily multi-generational, family business as a conduit for generational continuity, and what J.K. Rowling instinctively understands about the re-enchantment of the world.

Intro/Outro: Legends of the Fall Main Theme - James Horner

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

Zack Grafman & Frank Theodat on The Boys Book of Adventure Sep 17, 2025

Show notes

I chat with editors Zack Grafman and Frank Theodat about the need for aspirational books for boys. Many recommendations from the Dads here, including classics like The Hardy Boys, Treasure Island, Jules Verne but also some new stuff (Redwall, How to Train your Dragon, even some video games).

We also talk the (potential) opportunity within independent publishing to create and distribute through“underground, conspiratorial, vibes based marketing” books that counter safe, effeminate, and uninspiring mainstream offerings. ‘Based Boys Books,’ as Zack puts it.

Look out for the launch of The Boys Book of Adventure Anthology, a new collection deliberately crafted to appeal to boys, as boys. The Anthology also happens include my next ‘Leo and Henry’ Adventure.

Buy the book on Amazon - https://amzn.to/42m7C66

Intro/Outro: The Ecstasy of Gold - Ennio Morricone

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

Ryan O'Connor - Nintendo, Switch 2, Conviction from Deep Work Jun 17, 2025

Show notes

In which I bring you one of the sharpest minds in fundamental equity analysis, my friend Ryan O'Connor of Crossroads Capital.

Ryan is a multidisciplinary thinker who combines rigorous fundamental analysis with a lot of of wit and wisdom. In this conversation, we dive deep into one of his ideas, none other than Nintendo. We discuss Ryan’s original contrarian thesis, how the business transformation has played out, and what to expect with recent release of the Switch 2.

If you enjoy this discussion, I highly recommend going back to listen to my 2020 interview with Ryan and checking out the Crossroads Capital investing letters, both masterclasses in thoughtful equity analysis.

Intro: Can’t Hardly Wait - The Replacements

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

Wyatt O'Rourke - Financialization of Bitcoin, Bitcoinization of Finance Apr 02, 2025

Show notes

I start the pod with some insights from the last four-year cycle in Bitcoin investing, comparing its annualized returns and drawdowns with other market proxies like the S&P 500, NASDAQ, and gold. I then welcome Wyatt O'Rourke, founder of Basilic Financial and author of 'The Bitcoinization of Finance,' to discuss Bitcoin's integration into traditional finance. Wyatt gets into private credit funds, Bitcoin-backed mortgages, and the importance of sound custody solutions. We then digress to a conversation on 'noblesse oblige' in the context of modern elites like Elon Musk and Donald Trump and emphasize the need to uphold moral and ethical standards.

00:00 Bitcoin's Four-Year Performance Analysis

06:48 Si Bheag, Si Mhor · Planxty

10:26 Financialization of Bitcoin

13:20 Bitcoin Derivatives and Loan Market

27:11 The Space: A Bitcoin Citadel

37:00 Noblesse Oblige and Bitcoin

44:19 Elon Musk and Donald Trump

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

Edward Stratemeyer & Adventures in Fiction Publishing Mar 07, 2025

Show notes

I talk boys books passed down through generations, including classic adventure series like the Hardy Boys. I also examine the life and contributions of Edward Stratemeyer, the mastermind behind the Hardy Boys, Tom Swift, and the Bobbsey Twins. Inspired by these classics, I share my own venture in children's literature with my new book series, 'The Adventures of Leo and Henry.

Links:

* Buy The Quest for the Lost Sword: The Adventures of Leo & Henry

* Intro: The Rocketeer (James Horner)

* Anthony Esolen - Defending Boyhood: How Building Forts, Reading Stories, Playing Ball, and Praying to God Can Change the World

* Dave Greene - An Age of Illiteracy

* Cover art: Passage Press - The Hardy Boys: The House on the Cliff

* Edward Stratemeyer and the Stratemeyer syndicate - Deidre Johnson

* The Mystery of Edward Stratemeyer Documentary - Lucasfilm

* EconTalk - Amor Towles on A Gentleman in Moscow and the Writer's Craft 8-29-22

* Calmversations - Scary Ideas- & The Mainstream Legitimacy Crisis - with Jonathan Keeperman

* Outro: The Adventures of Tintin theme

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

I Wrote a Hardy Boys-esque Boys' Book Dec 16, 2024

Show notes

The Adventures of Leo & Henry - The Quest for the Lost Sword

The book is now available for purchase on Amazon and Gumroad (digital version only).

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com

Notes on Trump, Getting Unstuck, and the American Empire Nov 21, 2024

Show notes

I share some personal views on another Trump presidency and allow myself a moment to indulge in some optimism. We get into the concept of America's decline, comparing it to the fall of Rome, and explore the potential for continuation of the empire. I riff on the commentary of Peter Thiel on Bari Weiss’s show, Trump’s Rogan appearance, Michael Goldstein on the Art of Bitcoin Rhetoric, the Kurt Steiner piece on American Empire: A Morale Project, and Isaac Simpson’s piece on the El Segundo Hard Tech movement.

00:00 Body of an American - The Pogues

01:17 Thoughts on Trump

10:31 Trump's Policies

17:53 The Power of Memes and Bitcoin

20:50 Reflections on the Future of America

23:36 The Decline of Rome and America

27:14 The American Empire: Great and Good?

30:14 The Stagnation and Decadence of Modern America

34:15 El Segundo Hard Tech movement

38:46 The Stock Market and American Capitalism

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com