Gentleman Speculator
Insights on investing, legacy, and the life well-lived from Andrew Flattery and Flattery Wealth Management, LLC. www.gentlemanspeculator.com
10
Have Yourself a Home Alone Family
<p>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 b...
Johann Kurtz (Becoming Noble) - Leaving a Legacy
<p>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. </p><p>Intro/Outro: Legends of the Fall Main Theme - James Horner</p><p></p> <br/><br/>This is a public episode. If you...
Zack Grafman & Frank Theodat on The Boys Book of Adventure
<p>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). </p><p>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. </p><p>Look out for the launch of The Boys Book of Adventure Anthology, a new co...
Ryan O'Connor - Nintendo, Switch 2, Conviction from Deep Work
<p>In which I bring you one of the sharpest minds in fundamental equity analysis, my friend Ryan O'Connor of Crossroads Capital.</p><p>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. </p><p>If you enjoy this discussion, I highly recommend going back to listen to my 2020 interview with Ryan an...
Wyatt O'Rourke - Financialization of Bitcoin, Bitcoinization of Finance
<p>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...
Edward Stratemeyer & Adventures in Fiction Publishing
<p>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.</p><p>Links:</p><p>* Buy The Quest for the Lost Sword: The Adventures of Leo & Henry</p><p>* Intro: The Rocketeer (James Horner)</p><p>* Anthony Esolen - Defending Boyhood: How Building Forts, Reading Stories, Playing Ball...
I Wrote a Hardy Boys-esque Boys' Book
<p> The Adventures of Leo & Henry - The Quest for the Lost Sword</p><p>The book is now available for purchase on Amazon and Gumroad (digital version only). </p><p></p> <br/><br/>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
<p>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. </p><p>00:00 Body of an American - The Pogues</p><p>01...
Don't Retire, Pull a Mel Gibson
<p>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.</p><p>02:47 The Problem with Subsidized Retirement</p><p>08:23 Mel Gibson's Future Projects</p><p>14:13 The Passion of the Christ Sequel</p><p>23:26 Mel’s Redemption Arc</p><p>23:48 True Elites</p><p>25:41 The Landed Gentry, Country Gentlemen</p><p>34:00 Alaric the Barbarian on “Traditional” things</p><p>Links: </p><p>* James...
Leandro González-Sicilia - Multi-Generational Family Businesses, Luxury Investing, Hermès
<p>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. </p><p>Leandro's work is thoughtful. He’s a deep researcher, and a bottom-up, long-term investor who avoids the...
