Gentleman Speculator

Andrew Flattery
  • 0.0 (0)
  • INVESTING
Gentleman Speculator

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

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

    2 APR

    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

    58 min

  2. 7 MAR

    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

    45 min

  3. 16/12/2024

    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

    2 min

  4. 21/11/2024

    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

    51 min
  5. Don't Retire, Pull a Mel Gibson

    23/10/2024

    Don't Retire, Pull a Mel Gibson

    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

    45 min

  6. 07/10/2024

    Leandro González-Sicilia - Multi-Generational Family Businesses, Luxury Investing, Hermès

    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

    45 min
  7. Clay Finck - 100 Baggers, Quality Investing, Bitcoin for Stock Pickers

    25/09/2024

    Clay Finck - 100 Baggers, Quality Investing, Bitcoin for Stock Pickers

    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 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

    48 min
  8. The Real Zorro, Noblesse Oblige, Gentleman Speculator

    11/09/2024

    The Real Zorro, Noblesse Oblige, Gentleman Speculator

    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

    45 min
See All (71)

About

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

Information

  • Creator
    Andrew Flattery
  • Years Active
    2020 - 2025
  • Episodes
    71
  • Rating
    Clean
  • Copyright
    © Andrew Flattery
  • Show Website
    Gentleman Speculator

You Might Also Like

To listen to explicit episodes, sign in.

Stay up to date with this show

Sign in or sign up to follow shows, save episodes and get the latest updates.
Select a country or region

Africa, Middle East, and India

Asia Pacific

Europe

Latin America and the Caribbean

The United States and Canada