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

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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

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 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

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

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 Retirement

08:23 Mel Gibson's Future Projects

14:13 The Passion of the Christ Sequel

23:26 Mel’s Redemption Arc

23:48 True Elites

25:41 The Landed Gentry, Country Gentlemen

34:00 Alaric the Barbarian on “Traditional” things

Links: 

* 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 Mayer

01:28 Meet Leandro

08:09 Debunking Common Investing Tropes

12:26 The Timeless Appeal of Luxury Brands

15:27 Luxury and Social Status

22:58 Hermès

31:08 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 Podcast

06:36 Avoiding Clickbait

10:07 Midwest small town values and investing

13:45 Chris Mayer’s ‘100 Baggers’

24:42 Constellation Software

32:51 Bitcoin for stock pickers

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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