Gentleman Speculator

Hosted by Andrew Flattery

Business Entrepreneurship Careers

Website RSS feed

Episodes

Latest episode

Jun 2026

Language

About the show

Insights on investing, legacy, and the life well-lived from Andrew Flattery and Flattery Wealth Management, LLC. www.gentlemanspeculator.com

Listen to episodes

60 recent

June 25, 20261 hr 1 min

The Dad Book Review

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

April 8, 202653 min

The Book of Elon

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

December 18, 202542 min

Have Yourself a Home Alone Family

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. C elebrating 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

November 25, 202558 min

Johann Kurtz (Becoming Noble) - Leaving a Legacy

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

September 17, 20251 hr 8 min

Zack Grafman & Frank Theodat on The Boys Book of Adventure

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

June 17, 20251 hr 23 min

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

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

April 2, 202558 min

Wyatt O'Rourke - Financialization of Bitcoin, Bitcoinization of Finance

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

March 7, 202544 min

Edward Stratemeyer & Adventures in Fiction Publishing

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

December 16, 20241 min

I Wrote a Hardy Boys-esque Boys' Book

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

November 21, 202450 min

Notes on Trump, Getting Unstuck, and the American Empire

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