Gentleman Speculator

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 FijanOutro: 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

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

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/42m7C66Intro/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

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

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 Analysis06:48 Si Bheag, Si Mhor · Planxty10:26 Financialization of Bitcoin13:20 Bitcoin Derivatives and Loan Market27:11 The Space: A Bitcoin Citadel37:00 Noblesse Oblige and Bitcoin44:19 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

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

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

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 Pogues01:17 Thoughts on Trump 10:31 Trump's Policies 17:53 The Power of Memes and Bitcoin20:50 Reflections on the Future of America23:36 The Decline of Rome and America27:14 The American Empire: Great and Good?30:14 The Stagnation and Decadence of Modern America34:15 El Segundo Hard Tech movement38:46 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

I delve into Mel Gibson's spot-on perspective on retirement, which I contend is unnatural in the modern hedonistic context. I explore Gibson’s commitment to staying creative and active into his later years, doing work that matters, and contrast this with our societal norm of subsidized and unexamined retirement.02:47 The Problem with Subsidized Retirement08:23 Mel Gibson's Future Projects14:13 The Passion of the Christ Sequel23:26 Mel’s Redemption Arc23:48 True Elites25:41 The Landed Gentry, Country Gentlemen34:00 Alaric the Barbarian on “Traditional” thingsLinks: * James Horner - The Legend * This is Why You Should Never Retire* Mel Gibson reveals more amazing stories live on stage in London! (IMP EPISODE 12)* Jim Caviezel Reveals What's Happening With 'Resurrection' Film* Randall Wallace Details 'Passion of the Christ' Sequel* The Patriot* The American Tribune - The Death of the Gentleman and the Birth of Bureaucratic Tyranny* Oliveira - Nobility and Analogous Traditional Elites: A Theme Illuminating American Social History* Alaric The Barbarian - Things that are more “traditional” than a 32 year old SWE and a 28 year old PM buying a farm with NVIDIA gains to larp as pioneers* Titus Techera - The Third Wave of Journalism* James Horner - A Gift of a Thistle 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 welcome Leandro of Best Anchor Stocks to Gentleman Speculator. Leandro is the co-founder of an investment research service and an equity analyst I deem worthy of paying attention to. We discuss the value of multi-generational family businesses, focusing especially on Hermès. Despite challenges, there is a small subset of public companies where being family controlled is a benefit. We talk luxury investing, how luxury brands are a reflection of human nature, and a contrast between European and American markets. Leandro's work is thoughtful. He’s a deep researcher, and a bottom-up, long-term investor who avoids the noise. Great Indoors - John Mayer01:28 Meet Leandro08:09 Debunking Common Investing Tropes 12:26 The Timeless Appeal of Luxury Brands15:27 Luxury and Social Status22:58 Hermès31:08 On Family-Owned, Publicly Traded Businesses 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

In this episode of GENTLEMAN SPECULATOR, I sit down with Clay Finck from 'We Study Billionaires' to discuss Chris Mayer's book '100 Baggers,' the quality investing ethos, and the friction stock analyst have with bitcoin. Clay shares his journey from being an actuary in Nebraska to going full time with The Investors Podcast Network. Highlights include specific companies like Copart and Constellation Software. Clay is one of the few guys I can have a conversation with about long-term investing, the value of high-quality businesses, and how Bitcoin breaks the mold.03:15 Clay's Journey to the Investors Podcast06:36 Avoiding Clickbait10:07 Midwest small town values and investing13:45 Chris Mayer’s ‘100 Baggers’24:42 Constellation Software32:51 Bitcoin for stock pickersSubscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

https://www.gentlemanspeculator.com/You heard right. The Reformed Financial Advisor Podcast? It's gone. Dead and buried. From now on, it's Gentleman Speculator. Cleaner. Sharp as a stiletto heel. Like Alain Delon's tailored slacks. Money is a tool. But this isn’t about counting beans anymore. We’re talking shadows, where the real power reveals itself. The true Zorro? It's William Lamport. And he doesn’t just fight with a sword; he fights with secrets. Bruce Wayne’s noblesse oblige? That’s not rotten lefty philanthropy—it’s blood, sweat, and munificence bestowed on a world that can't get clean.In this cesspool we call progress, a few old stories still have teeth - The Dark Knight, Finkle-McGraw, Holmes, and, Marlowe. Sharp enough to bite, vicious enough to remind us of the American myths we once knew.The truth? The answers are out there, somewhere between the rain-soaked streets of high finance and the dusted corridors of the liberal arts. It’s all connected—sleuthing, speculating, playing the long game. And if you're not seeing the big picture, you're already yesterday's news.But don’t expect an easy listen. The rabbit hole’s deep, one misstep and you're in free fall. Welcome to Gentleman Speculator.Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

In conversation again with Tim Wuebker. We discussed inflation, deflation, hard money, and the moral case for Bitcoin. I recall how the 2008 financial crisis led me to question the stability of traditional financial systems and eventually turned me towards Bitcoin, especially during the money-printing spree of 2020. We delved into the advantages of Bitcoin, such as its deflationary nature, portability, and cryptographic security, while also addressing the challenges, including its public ledger and the need for tech-savviness to manage private keys. It's always a good time to do a go-anywhere chat with Tim. Check out Tim Wuebker's podcast, Seemingly Ordinary: https://timwuebker.com/Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

While bitcoin is in common parlance now in market commentary, politics, and internet culture, few understand what could be an idea hiding in plain sight. This is good news for us, as herein lies the opportunity.July 2024 Special Report - Andrew FlatterySubscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

I have a deep and varied conversation with Devin Rose, a Catholic author, blogger, and software engineer. We dive into topics like writing books, moral guidance for Catholic investors, and the debate between Bitcoin and Ethereum. Devin shares his personal journey from militant atheism to Catholicism, his experiences with homesteading, and his insights on investing in a way that aligns with Catholic values. Devin also talks about his various book projects, including his effort in fiction writing, and his "there and back again" story with Bitcoin. Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

In this Reformed Financial Advisor pod I talk with my friend Bryant Suellentrop, who shares his journey from from scratch to success in various businesses. Bryant reveals how he transitioned from a web design business to a profitable cleaning company and ultimately founded a recruiting agency, Elevate and Delegate. He discusses the advantages of virtual work, using twitter for business growth, and the importance of ownership in the HARRISON BUTKER story. Bryant is a good dude, I like his entrepreneurial spirit and example of taking calculated baby steps in business.www.simplewealthkc.com/post/lean-entrepreneurship-twitter-harrison-butker-bryant-suellentropSubscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

I dive into evolution of Michael Saylor alongside his company, MicroStrategy, illustrating Saylor's rise from humble beginnings, the establishment of MicroStrategy driven by his tech foresight, and the challenges he faced post an accounting scandal in 2000. I consider Saylor as a visionary who deftly navigates through adversities, embraces innovations like Bitcoin, displays skin in the game, and always a willingness to risk it all. Episode page: www.simplewealthkc.com/post/notes-on-young-michael-saylorSubscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

In this episode, I delve into optimizing life while leaving a meaningful legacy. I critique the "Die With Zero" concept, popularized by Bill Perkins and others. Perkins stresses intentional living by managing time, wealth, and health effectively, but at the expense of family wealth and legacy.I also explore the societal shift towards individualism and instant gratification and contrast it with the traditional values of family and legacy. The role of the family can be in providing support, guidance, and purpose. Building family wealth and nurturing intergenerational connections are ways to leave a lasting impact that extends beyond one's lifetime.Episode page: www.simplewealthkc.com/post/against-die-with-zeroSubscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

In this episode of The Reformed Financial Advisor podcast,  I explore the topic of family wealth from a Catholic perspective. My guest is Dorian Antešić, a finance professional and Croatia's Catholic bitcoiner. We discuss his graduate school thesis on family wealth, Bitcoin, how Tucker Carlson said inheritance is a huge problem, a Benedictine monastery in Croatia, family dynasties, and the noblesse oblige.  All in all an interesting conversation that combines legacy, finance, and the pursuit of generational prosperity.Episode Links:The Noblesse Oblige - Andy Flattery on Catholic Money MastermindDorian on LinkedInhttps://www.antesic.com/Good King Wenceslaus - The Irish RoversTucker Carlson - All-In PodcastSubscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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

I have a wonderful conversation with fellow Financial Advisor, Isaiah Douglass. We discuss:Building onlineJoining Swan Private ClientAndy hates soccer/Isaiah likes soccerCOVID breaking our brainsHow FAs simp for inflationBitcoin and the american dreamEpisode page: www.simplewealthkc.com/post/the-freedom-to-have-an-opinion-isaiah-douglassSubscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning 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