<?xml version="1.0" encoding="UTF-8"?><rss xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:content="http://purl.org/rss/1.0/modules/content/" xmlns:atom="http://www.w3.org/2005/Atom" version="2.0" xmlns:itunes="http://www.itunes.com/dtds/podcast-1.0.dtd" xmlns:googleplay="http://www.google.com/schemas/play-podcasts/1.0"><channel><title><![CDATA[Gentleman Speculator]]></title><description><![CDATA[Insights on investing, legacy, and the life well-lived from Andrew Flattery and Flattery Wealth Management, LLC.]]></description><link>https://www.gentlemanspeculator.com</link><image><url>https://substackcdn.com/image/fetch/$s_!5jZZ!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd7d33196-9cba-4c7c-a158-70570c2f49cc_1280x1280.png</url><title>Gentleman Speculator</title><link>https://www.gentlemanspeculator.com</link></image><generator>Substack</generator><lastBuildDate>Tue, 28 Apr 2026 21:32:14 GMT</lastBuildDate><atom:link href="https://www.gentlemanspeculator.com/feed" rel="self" type="application/rss+xml"/><copyright><![CDATA[Andrew Flattery]]></copyright><language><![CDATA[en]]></language><webMaster><![CDATA[gentlemanspeculator@substack.com]]></webMaster><itunes:owner><itunes:email><![CDATA[gentlemanspeculator@substack.com]]></itunes:email><itunes:name><![CDATA[Andrew Flattery]]></itunes:name></itunes:owner><itunes:author><![CDATA[Andrew Flattery]]></itunes:author><googleplay:owner><![CDATA[gentlemanspeculator@substack.com]]></googleplay:owner><googleplay:email><![CDATA[gentlemanspeculator@substack.com]]></googleplay:email><googleplay:author><![CDATA[Andrew Flattery]]></googleplay:author><itunes:block><![CDATA[Yes]]></itunes:block><item><title><![CDATA[The Book of Elon]]></title><description><![CDATA[A Conversation with Eric Jorgenson]]></description><link>https://www.gentlemanspeculator.com/p/the-book-of-elon</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/the-book-of-elon</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Wed, 08 Apr 2026 10:59:39 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/193534354/848745be46524c719a8867d52a3108c7.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p>Eric Jorgenson is back on the pod to talk about his new book, The Book of Elon, a five-year project distilling Elon Musk&#8217;s most useful ideas in his own words. Eric and I talk about why Musk is the greatest living entrepreneur, the recursive logic of &#8216;stacking S-curves,&#8217; 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.</p><p><strong>Buy the book: </strong></p><p>https://www.elonmuskbook.org/</p><p><strong>Follow Eric: </strong><a href="https://x.com/EricJorgenson">https://x.com/EricJorgenson</a></p><p><strong>Eric&#8217;s Smart Friends podcast: </strong></p><p>https://www.ejorgenson.com/</p><p><strong>Music: </strong><em>&#8220;The Big Ship&#8221; by Brian Eno</em></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!L0qj!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4dc498b1-ef8e-4e32-b5b1-03afb8d9660a_3024x4032.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" 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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.</em></p></blockquote>]]></content:encoded></item><item><title><![CDATA[Flattery Wealth 2025 Annual Letter]]></title><description><![CDATA[Friends,]]></description><link>https://www.gentlemanspeculator.com/p/flattery-wealth-2025-annual-letter</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/flattery-wealth-2025-annual-letter</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Tue, 20 Jan 2026 19:31:14 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!BJM_!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4e6486da-ab1b-4d30-a767-da179bb80d44_3300x2550.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Friends, </p><p>My <a href="https://www.flatterywealth.com/">Flattery Wealth Management </a>Annual Letter is available to download in PDF form here:</p><p><a href="https://cdn.prod.website-files.com/641943f24cf884769a1713d1/696a833b2be8274aed040de8_2025%20Flattery%20Wealth%20Annual%20Letter.pdf">2025 Annual Letter</a></p><p>This year&#8217;s letter explores the balance between staying true to the investment philosophy and adapting to changing markets. Humor me as I use John Mayer&#8217;s career arc as the analogy. I address the disappointing investment results in 2025, review our multi-bagger investments, share thoughts on AI, and where we go from here.</p><p>Thanks,</p><p>Andy Flattery</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!BJM_!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4e6486da-ab1b-4d30-a767-da179bb80d44_3300x2550.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!BJM_!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4e6486da-ab1b-4d30-a767-da179bb80d44_3300x2550.jpeg 424w, 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stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p>]]></content:encoded></item><item><title><![CDATA[Have Yourself a Home Alone Family]]></title><description><![CDATA[Peter McCallister is Peak America]]></description><link>https://www.gentlemanspeculator.com/p/have-yourself-a-home-alone-family</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/have-yourself-a-home-alone-family</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Thu, 18 Dec 2025 10:35:30 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/181905508/ad6aeab0f7b084a84290a6eb0ca015bf.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<div class="comment" data-attrs="{&quot;url&quot;:&quot;https://open.substack.com/home&quot;,&quot;commentId&quot;:185939430,&quot;comment&quot;:{&quot;id&quot;:185939430,&quot;date&quot;:&quot;2025-12-09T16:49:00.439Z&quot;,&quot;edited_at&quot;:null,&quot;body&quot;:&quot;Peter McCallister is peak America  \n\n- Patriarch of a big family \n\n- Sponsors extended family trip to France \n\n- Late for a flight doesn't phase him \n\n- Early '90s yuppy aesthetic \n\n- Sort of okay with letting his 8-year old son have a few days on his own \n\n- Owns a nice house&quot;,&quot;body_json&quot;:{&quot;type&quot;:&quot;doc&quot;,&quot;attrs&quot;:{&quot;schemaVersion&quot;:&quot;v1&quot;},&quot;content&quot;:[{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;Peter McCallister is peak America  &quot;}]},{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;- Patriarch of a big family &quot;}]},{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;- Sponsors extended family trip to France &quot;}]},{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;- Late for a flight doesn't phase him &quot;}]},{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;- Early '90s yuppy aesthetic &quot;}]},{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;- Sort of okay with letting his 8-year old son have a few days on his own &quot;}]},{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;- Owns a nice house&quot;}]}]},&quot;restacks&quot;:15,&quot;reaction_count&quot;:172,&quot;attachments&quot;:[{&quot;id&quot;:&quot;65347d13-a888-4e1d-bfac-7df2666b1115&quot;,&quot;type&quot;:&quot;image&quot;,&quot;imageUrl&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/cd6ad899-8b1a-4289-ad0d-2c493360d41e_1063x1500.jpeg&quot;,&quot;imageWidth&quot;:1063,&quot;imageHeight&quot;:1500,&quot;explicit&quot;:false}],&quot;name&quot;:&quot;Andrew Flattery&quot;,&quot;user_id&quot;:17251510,&quot;photo_url&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/30ae465e-50a1-4ae7-beec-efb721b01a58_1200x1200.png&quot;,&quot;user_bestseller_tier&quot;:null,&quot;userStatus&quot;:{&quot;bestsellerTier&quot;:null,&quot;subscriberTier&quot;:1,&quot;leaderboard&quot;:null,&quot;vip&quot;:false,&quot;badge&quot;:{&quot;type&quot;:&quot;subscriber&quot;,&quot;tier&quot;:1,&quot;accent_colors&quot;:null},&quot;paidPublicationIds&quot;:[1743362,1215941,1887871],&quot;subscriber&quot;:null}}}" data-component-name="CommentPlaceholder"></div><p>I dive into what I&#8217;m calling peak America, that is the Peter McAllister (Dad) character from <em>Home Alone</em>. Watching this at age 41 and the movie is now a meditation on what&#8217;s worth fighting for. I get into how the McAllister house functions as a &#8216;castle&#8217; for the kind of multi-generational family life that <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Johann Kurtz&quot;,&quot;id&quot;:113000652,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substackcdn.com/image/fetch/$s_!CVje!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8adf93ac-933c-4ae9-b184-1635903a61b3_1990x1990.png&quot;,&quot;uuid&quot;:&quot;d069c836-2633-4514-8b38-a86585ee97f2&quot;}" data-component-name="MentionToDOM"></span> writes about in <em>Leaving a Legacy: Inheritance, Charity, &amp; Thousand-Year Families</em>. I look at how Kevin&#8217;s initiation by older brother Buzz embodies what <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Anthony Esolen&quot;,&quot;id&quot;:40681817,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com/public/images/21680783-95c3-4d6a-9f62-9efe87775dd5_230x324.jpeg&quot;,&quot;uuid&quot;:&quot;f966ae69-251e-4e30-9439-92e72596de6b&quot;}" data-component-name="MentionToDOM"></span> describes in <em>No Apologies: Why Civilization Depends on the Strength of Men</em>, a rough-and-tumble world where boys learn to build, explore, and fight. There&#8217;s even the church scene with Old Man Marley that delivers a Christmas message. I contrast all of this with the so-called &#8216;found family&#8217; therapeutic culture that tells you to replace rather than reconcile. </p><p><em>C</em>elebrating the chaos, the legacy, the adventure of family life, and a classic movie for Christmas 2025. </p><p>Intro: The Drifters&#8217; &#8220;White Christmas&#8221;</p><p>Credit to the <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Aaron M. Renn&quot;,&quot;id&quot;:4168013,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substackcdn.com/image/fetch/$s_!dSRu!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fbucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com%2Fpublic%2Fimages%2F498f34a3-8be4-40d1-aabe-aeda99473f4b_1000x742.png&quot;,&quot;uuid&quot;:&quot;7d575bba-b7c4-4126-98e5-5e06d91f3a2f&quot;}" data-component-name="MentionToDOM"></span> episode <strong><a href="https://www.aaronrenn.com/p/why-families-are-fleeing-cities-bobby-fijan">Why Families Are Fleeing Cities | Bobby Fijan</a></strong></p><p>Outro: Mel Torme&#8217;s &#8220;Have Yourself a Merry Little Christmas&#8221;</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!Upr4!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1f4a34e9-bb14-4aea-b915-27995f352d50_1000x563.webp" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!Upr4!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1f4a34e9-bb14-4aea-b915-27995f352d50_1000x563.webp 424w, https://substackcdn.com/image/fetch/$s_!Upr4!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1f4a34e9-bb14-4aea-b915-27995f352d50_1000x563.webp 848w, https://substackcdn.com/image/fetch/$s_!Upr4!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1f4a34e9-bb14-4aea-b915-27995f352d50_1000x563.webp 1272w, https://substackcdn.com/image/fetch/$s_!Upr4!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1f4a34e9-bb14-4aea-b915-27995f352d50_1000x563.webp 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!Upr4!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1f4a34e9-bb14-4aea-b915-27995f352d50_1000x563.webp" width="1000" height="563" 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class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div>]]></content:encoded></item><item><title><![CDATA[Johann Kurtz (Becoming Noble) - Leaving a Legacy]]></title><description><![CDATA[My Conversation With the Author of an Important New Book on Building 1,000 Year Families]]></description><link>https://www.gentlemanspeculator.com/p/johann-kurtz-becoming-noble-leaving</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/johann-kurtz-becoming-noble-leaving</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Tue, 25 Nov 2025 10:47:46 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/179847217/3f68fcf3b8652819f930e0f852ce96e0.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p>I speak with with the semi-pseudonymous <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Johann Kurtz&quot;,&quot;id&quot;:113000652,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substackcdn.com/image/fetch/$s_!CVje!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8adf93ac-933c-4ae9-b184-1635903a61b3_1990x1990.png&quot;,&quot;uuid&quot;:&quot;14fb6c71-8c69-4bf9-919d-7e79e8f399c8&quot;}" data-component-name="MentionToDOM"></span> on his terrific new book <em><a href="https://amzn.to/48xNfpR">Leaving a Legacy: Inheritance, Charity, &amp; Thousand-Year Families.</a> </em> Johann lays out the foundation for why it can be moral to leave an inheritance when pared with virtue. We talk how <em>&#8216;Die with Zero&#8217;</em> 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><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!Q-du!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd262a45d-17af-4308-9b62-ddca5a6fd961_2760x3664.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!Q-du!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fd262a45d-17af-4308-9b62-ddca5a6fd961_2760x3664.jpeg 424w, 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class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p>]]></content:encoded></item><item><title><![CDATA[The Casey's Pizza Inflation Index (CPI)]]></title><description><![CDATA[The price of gas station food matters to Iowans]]></description><link>https://www.gentlemanspeculator.com/p/the-caseys-pizza-inflation-index</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/the-caseys-pizza-inflation-index</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Thu, 13 Nov 2025 15:42:24 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!hwdR!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Around four years ago, I posted a joke on Twitter about Casey&#8217;s gas station pizza getting more expensive. I called it the &#8220;Casey&#8217;s Pizza Inflation Index (CPI)&#8221; and framed it as a quasi-earnest effort to track inflation, with a subtle jab at the money printers and self-serious economic bean counters. This post checked a few boxes for me as I&#8217;m a financial advisor, a bit of an <em>inflation truther, </em>and native Iowan<em>. A</em>nd honestly, I like the pizza. I&#8217;m also part of the bitcoin community that has inherited the sound money critique from gold bugs and made it relevant in 2025. </p><p>So a combination of good humor, a meaningful midwest brand, inflation angst, and love for gas station pizza have now turned this into an annual thing.  </p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.gentlemanspeculator.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Gentleman Speculator! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>Here is the 2025 post:</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://x.com/andyflattery/status/1988666778017210750?s=20" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!hwdR!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 424w, https://substackcdn.com/image/fetch/$s_!hwdR!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 848w, https://substackcdn.com/image/fetch/$s_!hwdR!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 1272w, https://substackcdn.com/image/fetch/$s_!hwdR!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!hwdR!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png" width="392" height="938" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:938,&quot;width&quot;:392,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:468359,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:&quot;https://x.com/andyflattery/status/1988666778017210750?s=20&quot;,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:&quot;https://www.gentlemanspeculator.com/i/178798172?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!hwdR!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 424w, https://substackcdn.com/image/fetch/$s_!hwdR!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 848w, https://substackcdn.com/image/fetch/$s_!hwdR!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 1272w, https://substackcdn.com/image/fetch/$s_!hwdR!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F8962204d-76dc-403d-9c06-c86e4ca8d4da_392x938.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Followed by a new FAQ this year:</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://x.com/andyflattery/status/1988689960011026823?s=20" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!kzZ_!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 424w, https://substackcdn.com/image/fetch/$s_!kzZ_!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 848w, https://substackcdn.com/image/fetch/$s_!kzZ_!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 1272w, https://substackcdn.com/image/fetch/$s_!kzZ_!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!kzZ_!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png" width="388" height="488" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/f63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:488,&quot;width&quot;:388,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:54525,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/png&quot;,&quot;href&quot;:&quot;https://x.com/andyflattery/status/1988689960011026823?s=20&quot;,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://www.gentlemanspeculator.com/i/178798172?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!kzZ_!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 424w, https://substackcdn.com/image/fetch/$s_!kzZ_!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 848w, https://substackcdn.com/image/fetch/$s_!kzZ_!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 1272w, https://substackcdn.com/image/fetch/$s_!kzZ_!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ff63813ec-fd01-4e6e-bbc6-75911641b5ea_388x488.png 1456w" sizes="100vw"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Is this pure slop? Tapping into midwest zeitgeist? The true measure of inflation? Just a reason for this analyst to eat gas station pizza? I&#8217;ll let the reader decide. </p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.gentlemanspeculator.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Gentleman Speculator! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[Zack Grafman & Frank Theodat on The Boys Book of Adventure]]></title><description><![CDATA[How to FiIl the Void (in Books Boys Actually Want to Read)]]></description><link>https://www.gentlemanspeculator.com/p/zack-grafman-and-frank-theodat-on</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/zack-grafman-and-frank-theodat-on</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Wed, 17 Sep 2025 10:46:21 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/173791590/93f804e08f0ed6958cdfb892a37c6c05.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p>I chat with editors <a href="https://substack.com/@zackgrafman">Zack Grafman</a> and <a href="https://substack.com/@franktheodat">Frank Theodat</a> 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<em> </em>&#8220;underground, conspiratorial, vibes based marketing&#8221; books that counter safe, effeminate, and uninspiring mainstream offerings. &#8216;Based Boys Books,&#8217; as Zack puts it. </p><p>Look out for the launch of <a href="https://amzn.to/42m7C66">The Boys Book of Adventure</a> Anthology, a new collection deliberately crafted to appeal to boys, as boys. The Anthology also happens include my next <a href="https://www.amazon.com/Quest-Lost-Sword-Adventures-Henry/dp/B0DQGRY8FV">&#8216;Leo and Henry&#8217; Adventure.</a></p><p>Buy the book on Amazon -<a href="https://amzn.to/42m7C66"> https://amzn.to/42m7C66</a></p><p>Intro/Outro: The Ecstasy of Gold - Ennio Morricone</p><div class="comment" data-attrs="{&quot;url&quot;:&quot;https://open.substack.com/home&quot;,&quot;commentId&quot;:139842493,&quot;comment&quot;:{&quot;id&quot;:139842493,&quot;date&quot;:&quot;2025-07-28T18:56:38.397Z&quot;,&quot;edited_at&quot;:null,&quot;body&quot;:&quot;I feel this&quot;,&quot;body_json&quot;:{&quot;type&quot;:&quot;doc&quot;,&quot;attrs&quot;:{&quot;schemaVersion&quot;:&quot;v1&quot;},&quot;content&quot;:[{&quot;type&quot;:&quot;paragraph&quot;,&quot;content&quot;:[{&quot;type&quot;:&quot;text&quot;,&quot;text&quot;:&quot;I feel this&quot;}]}]},&quot;restacks&quot;:1,&quot;reaction_count&quot;:11,&quot;attachments&quot;:[{&quot;id&quot;:&quot;66c8993d-60d0-45bb-bb95-c6c3174d7b46&quot;,&quot;type&quot;:&quot;image&quot;,&quot;imageUrl&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/645e9cd2-92eb-4da3-a1e5-c39695b6c6dd_4032x3024.jpeg&quot;,&quot;imageWidth&quot;:3024,&quot;imageHeight&quot;:4032,&quot;explicit&quot;:false}],&quot;name&quot;:&quot;Andrew Flattery&quot;,&quot;user_id&quot;:17251510,&quot;photo_url&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/30ae465e-50a1-4ae7-beec-efb721b01a58_1200x1200.png&quot;,&quot;user_bestseller_tier&quot;:null}}" data-component-name="CommentPlaceholder"></div><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" 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srcset="https://substackcdn.com/image/fetch/$s_!9c77!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F71adc76d-0b08-4354-bdeb-441e2d906af9_1800x2700.jpeg 424w, https://substackcdn.com/image/fetch/$s_!9c77!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F71adc76d-0b08-4354-bdeb-441e2d906af9_1800x2700.jpeg 848w, https://substackcdn.com/image/fetch/$s_!9c77!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F71adc76d-0b08-4354-bdeb-441e2d906af9_1800x2700.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!9c77!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F71adc76d-0b08-4354-bdeb-441e2d906af9_1800x2700.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p>]]></content:encoded></item><item><title><![CDATA[Moral Money: The Case for Bitcoin (Eric Sammons)]]></title><description><![CDATA[Thoughts on the first 'Catholic' Bitcoin Book]]></description><link>https://www.gentlemanspeculator.com/p/moral-money-the-case-for-bitcoin</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/moral-money-the-case-for-bitcoin</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Tue, 24 Jun 2025 22:01:55 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/54f396f6-274a-45d0-9e85-3f853ce953ba_4032x3024.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>A confession: I occasionally get asked to speak to Catholic Church leaders about bitcoin. The idea sounds straightforward enough: it's moral money, potentially lucrative, so what could go wrong?</p><p>As it turns out, quite a lot.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.gentlemanspeculator.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Gentleman Speculator! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>While I&#8217;ve observed plenty of <em>individual</em> Catholics using bitcoin in various ways, my interactions with the broader institutional Church often run up against a sort of &#8216;decision by committee&#8217; bureaucracy. Exceptions exist on the fringes, the great Benedictines of Mary Queen of the Apostles <a href="https://bitcoinmagazine.com/culture/catholic-nuns-building-church-with-bitcoin">being one</a>. But generally speaking, Church pension funds, endowments, and collection baskets have not yet adopted this 16-year-old technology, let alone the best performing asset of the last decade (save Fr. Blaha&#8217;s <a href="https://www.blessedsacramentkck.org/">parish lightning node</a>).</p><p>This is why it is a big deal that <a href="https://amzn.to/4h6tqc9">Eric Sammons' new book</a> was released with a Catholic publisher; the erudite Sophia Institute Press, at that. While it was probably time for a book like this to be published for Catholics, Sammons is one of the few prominent authors who could have actually gotten it done. I've followed Eric's work since 2016-2017, when he was among the few (if any) Catholic thinkers taking bitcoin seriously. He was onto then what many missed (and still do): it&#8217;s not about &#8216;the blockchain&#8217;, tokenizing everything, name-your-niche-crypto narrative, etc. It&#8217;s about the money.</p><p>So I was glad to offer my endorsement for the book:</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!zfVm!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!zfVm!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 424w, https://substackcdn.com/image/fetch/$s_!zfVm!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 848w, https://substackcdn.com/image/fetch/$s_!zfVm!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!zfVm!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!zfVm!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg" width="1456" height="485" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/dfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:485,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!zfVm!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 424w, https://substackcdn.com/image/fetch/$s_!zfVm!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 848w, https://substackcdn.com/image/fetch/$s_!zfVm!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!zfVm!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fdfeb24aa-50e6-40aa-a705-eb6766ee486e_1600x533.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h2><strong>A Structure of Sin</strong></h2><p>Sammons opens boldly: our current financial system constitutes what he calls a "structure of sin." He writes "this hamster-wheel of excessive spending, risky investments, and debt slavery is engendering financial nihilism among the young." Remember those quaint times when "just save your money" was legitimate financial advice? Now we have to give warnings about inflation, market volatility, and the imperative to "put your money to work." This shift tells us everything. I think this is the Catholic case for bitcoin in a nutshell: savings are a fundamental good, families need savings to grow and prosper, but fiat currency (i.e. money by decree) has undermined our basic ability to save. </p><p>Bitcoin is a sound money alternative that restores and improves upon savings technology.</p><p>And why not? Christ talked about money more than any other topic. Nearly 15% of his recorded teachings address financial matters. Yet somehow, we've managed to treat our monetary system as <em>morally neutral</em> background noise. Like the weather or gravity. We've become so accustomed to inflation, debt cycles, and financial fragility that we think these conditions are normal.</p><h2><strong>Bitcoin as Moral Framework</strong></h2><p>Here enters bitcoin. Sammons engages with bitcoin's technical attributes as a moral framework. Design features like the 21 million fixed supply, proof-of-work consensus, and cryptographic verification could embody ethical principles in ways our institutions have struggled. The properties of the system create incentive structures that either support or undermine human flourishing.</p><p>A good example fleshed out here is the Cantillon Effect. This is the idea that those closest to <em>money</em> <em>creation</em> benefit disproportionately from new money entering the system. Under fiat currency, this creates systematic advantages for the well-connected, while gradually eroding the purchasing power of ordinary people's savings. If it bothers you when mega corporations receive <a href="https://econedlink.org/wp-content/uploads/2021/01/Brief-History-of-US-Bailoutsdocx.pdf">billion dollar bailouts</a> at the downstream expense of a families&#8217; basic food budget, you naturally intuit this. Bitcoin's predetermined inflation schedule eliminates this inequality, which the book argues reflects the Church's preferential option for the poor.</p><p>All of this line of reasoning makes me wonder, why shouldn't there be a Catholic <a href="https://cdn.nakamotoinstitute.org/docs/the-ethics-of-money-production.pdf">ethics of money production</a>? The Church already has teachings on inflation, usury, and currency debasement, but these seem to have been relegated to the obscure and arcane. </p><p>Bitcoin, by contrast, has its ethical framework built directly into its code.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!2KMv!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!2KMv!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png 424w, https://substackcdn.com/image/fetch/$s_!2KMv!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png 848w, https://substackcdn.com/image/fetch/$s_!2KMv!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png 1272w, https://substackcdn.com/image/fetch/$s_!2KMv!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!2KMv!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png" width="902" height="746" 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https://substackcdn.com/image/fetch/$s_!2KMv!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png 848w, https://substackcdn.com/image/fetch/$s_!2KMv!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png 1272w, https://substackcdn.com/image/fetch/$s_!2KMv!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe3fc76d7-3425-40b2-bba3-f19482a6babb_902x746.png 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a><figcaption class="image-caption">Nicolas Oresme pictured on the cover of Guido Hulsmann&#8217;s '&#8220;The Ethics of Money Production&#8221;</figcaption></figure></div><h2><strong>Getting to Honest Money</strong></h2><p>There are questions raised here that I still wrestle with. If the end game of bitcoin adoption is a sound money standard, what will it take to get there? Does this monetary upgrade also create new contexts for vice (i.e. the overnight millionaire problem, shirtsleeves to shirtsleeves in 3 generations, wealth for its own sake, etc.)? We have seen how the <em>speculation</em> phase of bitcoin adoption has come with its own share of insanity at times.</p><p>There is also the question of transition. The path from here to sound money involves disruption to the status quo. Let&#8217;s be honest, some of our institutions are flawed, but for better or worse provide essential services. A monetary upgrade, however justified theoretically, will likely impose real costs on real people. Priests and Bishops will naturally worry about their parishioners bearing the costs, even when the long-term benefits seem clear.</p><p>Sammons acknowledges these tensions but keeps it simple, the book after all intended to be a primer.</p><h2>Bitcoin as a Force for Good</h2><p>"Moral Money" is not superficial <em>crypto</em> advocacy but a serious look at the morality of our financial system. Whether bitcoin fulfills its promise as "the most moral money in human history" remains an open question. But the deeper point stands: monetary systems help shape behavior, distribute power, and support or undermine human dignity.</p><p>Years ago, these sorts of critiques of financialization and fiat currency would have been viewed as crank opinions. But I sense the culture has shifted. Bitcoin, and the conversation surrounding it, is in part to thank for this. In this sense, it has already succeeded.</p><p>Despite my small frustrations with institutional decision-making, it&#8217;s also true that ideas spread rapidly today. So I plan to hand this book to priests, bishops, and Catholic laymen I come in contact with to give a base level understanding of bitcoin as moral money. It's not totally unbelievable to think that our new American Pope Leo XIV could be given a copy of <a href="https://amzn.to/4h6tqc9">"Moral Money," </a>that he could read it, and that we could legitimately see an encyclical that addresses these issues. </p><p>When the Church again sees money as a moral question - not just how we use it, but how it's created and distributed - bitcoin becomes a force for good in the world and the Church.</p><p></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.gentlemanspeculator.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Gentleman Speculator! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[Ryan O'Connor - Nintendo, Switch 2, Conviction from Deep Work]]></title><description><![CDATA[In which I bring you one of the sharpest minds in fundamental equity analysis, my friend Ryan O'Connor of Crossroads Capital.]]></description><link>https://www.gentlemanspeculator.com/p/ryan-oconnor-nintendo-switch-2-conviction</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/ryan-oconnor-nintendo-switch-2-conviction</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Tue, 17 Jun 2025 20:58:10 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/165205328/2f0428d8da50886e762f08061f0ad626.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p>In which I bring you one of the sharpest minds in fundamental equity analysis, my friend <a href="https://x.com/AboveAvgOdds">Ryan O'Connor</a> 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&#8217;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 <a href="https://www.gentlemanspeculator.com/p/how-would-warren-buffett-invest-if-3eb?utm_source=publication-search">2020 interview with Ryan</a> and checking out the <a href="https://www.crossroadscap.io/ourteam">Crossroads Capital</a> investing letters, both masterclasses in thoughtful equity analysis.</p><p>Intro: Can&#8217;t Hardly Wait - The Replacements</p>]]></content:encoded></item><item><title><![CDATA[Why I Put My Name on the Door]]></title><description><![CDATA[The Best Name for your Business is your Own]]></description><link>https://www.gentlemanspeculator.com/p/why-i-put-my-name-on-the-door</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/why-i-put-my-name-on-the-door</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Mon, 28 Apr 2025 14:01:51 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Recently I made an overdue change for my investment firm. After years operating as &#8216;Simple Wealth Planning,&#8217; I renamed (yes, <em>rebranded</em>) to <a href="https://www.flatterywealth.com/">Flattery Wealth Management.</a> This change reflects a many years-long shift in how I view my business and its purpose.</p><h2><strong>Introduction</strong></h2><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!6lRP!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!6lRP!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 424w, https://substackcdn.com/image/fetch/$s_!6lRP!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 848w, https://substackcdn.com/image/fetch/$s_!6lRP!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 1272w, https://substackcdn.com/image/fetch/$s_!6lRP!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!6lRP!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png" width="460" height="413" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:413,&quot;width&quot;:460,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!6lRP!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 424w, https://substackcdn.com/image/fetch/$s_!6lRP!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 848w, https://substackcdn.com/image/fetch/$s_!6lRP!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 1272w, https://substackcdn.com/image/fetch/$s_!6lRP!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9eaa848a-579a-45c6-8e37-afecad5a0fdc_460x413.png 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a><figcaption class="image-caption">Credit to Dorian Ante&#353;i&#263; for providing me with this meme</figcaption></figure></div><blockquote><p>A slight aesthetic thing I believe in very strongly is the names of companies are often very predictive of future failure or success. </p><p>- Peter Thiel</p></blockquote><p>During a <a href="https://conversationswithtyler.com/episodes/peter-thiel/">conversation</a> with Tyler Cowen, Peter Thiel once talked about his obsession with company naming. Thiel, who named his data analytics company &#8216;Palantir&#8217; after the all-seeing stones from Tolkien's Lord of the Rings, believes that names aren't merely labels; they're declarations of intent and vision.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.gentlemanspeculator.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Gentleman Speculator! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div><p>The Romans understood had a saying for this, <em>"nomen est omen"</em>&#8212;the name is a sign. Names carry meaning and responsibility.</p><p>My original name for the firm in 2018, (&#8216;Simple Wealth Planning&#8217;), now strikes me as what I might describe as normie; generic, sort of forgettable, a bit disposable. It projected the image of a fleeting organization built not for longevity, but for acquisition. It hinted at: <em>this is temporary.</em></p><p>I was intentionally trying <em>not</em> to sound stodgy or self-aggrandizing. Now, I've come to realize this name telegraphed precisely the wrong message about my intentions in business. Today, I'd like to share why I've rebranded and why I believe putting your name on the door is a good idea.</p><h2><strong>The Acquisition Epidemic</strong></h2><p>Let&#8217;s begin by taking a look at the current landscape of Wealth Management, the industry I&#8217;ve worked in since 2010. I think it&#8217;s instructive in understanding a lot of what&#8217;s happening in the marketplace in 2025. Today's dominant model is aggregation; giant advisory businesses functioning primarily as acquisition platforms. This structure allows founders to operate independently and to exit more easily, while paying a percentage upward to the parent organization. The result? Firms claiming billions &#8216;under management&#8217; that more or less administer a software stack and a back office on behalf of those who sell.</p><p>This ecosystem has created a burgeoning culture of seller-founders influenced by payouts. Without getting too hyperbolic, the endgame doesn&#8217;t seem to be service excellence or multi-generational impact, it's maximizing the sale price. I don&#8217;t think it&#8217;s a controversial statement to say that advisors, or any entrepreneurs, designing businesses specifically <em>for acquisition</em> will build differently than those building for permanence. In other words, the point of starting the business is to sell it. I'm slightly exaggerating for brevity's sake, but not much.</p><p>Contrast this with this ideal of stewardship that you might expect from a wealth manager holding itself out as world-class.</p><p>Here is <a href="https://www.downtownjoshbrown.com/p/new-post-adc6">Josh Brown</a>: </p><blockquote><p>..why would anyone set out to build an aggregator in the first place? I guess, cynically, because you can sell PE on the idea of compounding capital by rolling up the industry, which is a model they&#8217;re very comfortable with from their experience with dentists and bowling alleys. Okay, but other than that - if you weren&#8217;t in it just for the money - why would you pursue this strategy? The answer is that you wouldn&#8217;t.</p><p>I&#8217;ve been offered money to go out and buy a bunch of firms several times in recent years. My response is always the same - why would I buy someone who isn&#8217;t as good as we are and then let them DBA using my firm as a resource? That&#8217;s backwards. If I&#8217;m going to buy someone (and I&#8217;m probably not), they&#8217;re either better than us already (LOL) or they want to become part of what we&#8217;re doing because they love it. I&#8217;m not giving someone capital to carry on as they were.</p></blockquote><h2><strong>The Conventional Wisdom</strong></h2><p>It is some combination of easy money, overfinancialization, and perhaps some existential crisis of meaning that have made selling out not just possible, but expected. The presiding narrative across industries has become predictable: build, scale, sell. Entrepreneurs are celebrated for exits rather than endurance. Your local roofing company bearing &#8216;Family-Owned Since 1978&#8217; on the sign is now viewed as quaint.</p><p>And the rollup model has seeped into nearly every corner of the economy: urgent care clinics, plumbers, hair stylists, gym chains, fast casual restaurants, and self-storage facilities. I imagine there are daycare centers being swallowed up by holding companies developing sophisticated financial models on the ROI of MAGNA-TILES in the play area (<em>From a capital allocation perspective, Picasso Tiles offer superior return, deliver near-identical utility per play hour at a significantly lower cost&#8212;an arbitrage made possible by the fact that the end-user lacks brand discernment</em>). The playbook is always the same, fragmented industries are targeted by aggregators who promise operational efficiency and scale.</p><p>What they often leave behind is homogenization.</p><p>What was once a local craft, trade, or vocation tied to a specific place and person is now optimized for EBITDA and eventual sale. A sale of these firms is often viewed as a success for the owners. In the case of family-owned enterprises, I think it's a tragedy.</p><p>This perspective might seem radical, but consider this: you might <em>not</em> want to just leave <em>liquid</em> assets (e.g. money) to children without due care. On the other hand, leaving <em>illiquid</em> assets (business, farm, real estate, etc) has the effect of keeping families together through shared purpose and enterprise. </p><p>Money divides, meaningful work unites.</p><h2><strong>The Multi-Generational Alternative</strong></h2><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!kpeV!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!kpeV!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 424w, https://substackcdn.com/image/fetch/$s_!kpeV!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 848w, https://substackcdn.com/image/fetch/$s_!kpeV!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!kpeV!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!kpeV!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg" width="978" height="736" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:736,&quot;width&quot;:978,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:null,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:null,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!kpeV!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 424w, https://substackcdn.com/image/fetch/$s_!kpeV!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 848w, https://substackcdn.com/image/fetch/$s_!kpeV!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!kpeV!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0191a7d6-f68c-4a1b-8f18-797bbfd56932_978x736.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><blockquote><p>What is the point in starting a business if not to pass on to your children? </p><p>&#8211; <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Evan Amato&quot;,&quot;id&quot;:39690514,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substackcdn.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F5e5f1110-c4f8-4945-be60-3c6f73c38a4d_1774x1774.jpeg&quot;,&quot;uuid&quot;:&quot;c42a0762-917d-463e-bf53-58180a9a8b2b&quot;}" data-component-name="MentionToDOM"></span>, <em><a href="https://becomingnoble.substack.com/p/inheritance-power-culture-w-evan">Becoming Noble</a></em> podcast</p></blockquote><p>Nassim Nicholas Taleb's &#8216;Skin in the Game&#8217; principle explains why family businesses often exceed their more corporate counterparts in long-term thinking. When your family name serves as collateral, when your kids&#8217; futures are intertwined with business outcomes, the risks and rewards remain contained within the household. This creates alignment that can&#8217;t be replicated in faceless corporate structures.</p><p>Take a look at the Dumas family, stewards of their luxury house&#8211;Herm&#232;s&#8211;since 1837 (and profiled in <a href="https://www.gentlemanspeculator.com/p/leandro-gonzalez-sicilia-multi-generational?utm_source=publication-search">my conversation</a> with Leandro Gonz&#225;lez-Sicilia). When sixth-generation family member Axel Dumas speaks of the business, he doesn't frame decisions in quarterly terms. He frames them in generational ones. The Herm&#232;s brand, painstakingly built over almost two centuries, is inextricably linked to the family identity. It started with the name of the founder and patriarch, Thierry Herm&#232;s, whose legacy has been carried forward by descendants, (even though it was the Dumas name that gained prominence through marriage). He created a culture where family members understand they are temporary custodians of a permanent legacy.</p><p>What does the name of the business have to do with this? For one thing, it signals accountability. While managerialism separates people from the consequences of their actions (Taleb writes about "the Bob Rubin Trade"&#8212;collecting bonuses for risks that others ultimately bear), family accountability creates radically different decision-making. Generic, made-up, marketing-speak-names make for a psychological distance between owners and business decisions. They offer a veneer of corporate anonymity that makes it easier to optimize for short-term gains.</p><p>Putting your name on the door eliminates this conflict and increases the skin in the game.</p><p>But what about the world's most successful companies bearing<em> non-family </em>names like Apple, Amazon, and Google? I suspect the rub emerges during founder transitions; through succession, sale, or death. Would Bill Gates' children still be involved with Microsoft (and <a href="https://fortune.com/2025/03/31/bill-gates-children-inheritence-microsoft-fortune-philanthropy/">due their inheritance</a>) had it been named &#8216;Gates Inc.&#8217; instead? Maybe.</p><p>Elon could still rebrand his ventures under &#8216;Musk Industries,&#8217; creating a natural path for <a href="https://www.youtube.com/shorts/ptpqezXemVc">Little X </a>to inherit not just wealth but purpose.</p><p>This isn&#8217;t a silver bullet. Even when properly named, family enterprises can become hollow shells if successors lose the original vision, commitment, and correct ownership structure. The gradual hollowing out of Disney is a cautionary tale. But I suspect most readers here aren't aiming to build global megacorps at all, but rather sustainable, profitable, and personal enterprises.</p><p>Pop culture sometimes reflects these truths intuitively. I have done a few movie commentary podcasts (<a href="https://www.gentlemanspeculator.com/p/the-real-zorro-noblesse-oblige-gentleman-86b">here</a> and <a href="https://www.gentlemanspeculator.com/p/hail-caesar-tally-ho-yacht-guy-and-dfb">here</a>) and the &#8216;90s classic&#8212;criminally-<a href="https://www.rottentomatoes.com/m/tommy_boy">underrated-on-Rotten-Tomatoes</a>&#8212;Tommy Boy is one I need to get around to. Whether the creators intended it or not, the movie can be viewed as an epic Shakespearean tale. Tommy Callahan III, a benevolent and hilarious Chris Farley/Henry V character, returns to his kingdom of Sandusky, Ohio to reclaim the throne and save his community. Fittingly, the company that Tommy saves bears his family name, setting up the key conflict in the story. Callahan Auto Parts is in danger of getting acquired. This is viewed as a tragic predicament, one that our hero Tommy must overcome. My guess is the creators didn't intend a deep reading of this trope, they were following a form that simply works in a great story.</p><p>But take another look, today the Tommy Boy narrative resonates.</p><blockquote><p>But as you realize 'Callahan' has been family owned since Tommy's great grandfather laid the first brick. And I'll be damned if that's gonna change on my watch.</p><p> - Thomas R. "Big Tom" Callahan Jr.</p></blockquote><p>It should go without saying that naming the company is just the beginning. The real work lies in embedding values and purpose deeply into the family culture so that they transcend any single individual's leadership.</p><h3><strong>My Personal Journey</strong></h3><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!3MPk!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!3MPk!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 424w, https://substackcdn.com/image/fetch/$s_!3MPk!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 848w, https://substackcdn.com/image/fetch/$s_!3MPk!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!3MPk!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!3MPk!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg" width="1456" height="816" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:816,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:517517,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://www.gentlemanspeculator.com/i/162142319?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!3MPk!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 424w, https://substackcdn.com/image/fetch/$s_!3MPk!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 848w, https://substackcdn.com/image/fetch/$s_!3MPk!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!3MPk!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F757ea7a8-85ef-4dff-8a08-d55ff7169564_1957x1097.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p>Throughout my career, I've watched as industry best practices push to commoditize wealth management services, to implement cookie-cutter portfolios with investing nihilism ("<em>nothing matters, just buy!</em>"), and avoid unconventional ideas regardless of their merit (<a href="https://www.gentlemanspeculator.com/p/the-pros-not-understanding-bitcoin">Bitcoin</a> being the obvious example). My inbox fills with promises from business coaches offering the proven formula for maximizing my exit multiple, as if selling were the inevitable outcome of building.</p><p>What these acquirers want are businesses that can be easily absorbed, rebranded, and homogenized. Assets&#8211;representing people, families, relationships&#8211;that transfer cleanly from one balance sheet to another. By putting my name on the door, I'm making a deliberate choice to resist this path.</p><p>I hope the message to customers is that I stand behind my work. Most importantly, I am telling my kids that they should be proud of their name and from whom they come from. Their Dad is at least <em>attempting</em> to create something of lasting value. Something they might one day help steward.</p><h3><strong>Conclusion</strong></h3><p>I would challenge men who are early in the entrepreneurial journey to look beyond conventional wisdom and ask: <em>What am I building that will endure? </em>The answer may begin, quite literally, with your name on the door.</p><p>A regret I have is not understanding this principle from the beginning. Your name isn't just a label or marketing gimmick. It's a promise to customers, a signal to the market, and a gift to your descendants.</p><p>In a world obsessed with exits and liquidity events, choosing permanence is radical. Your name isn't just your most valuable asset, it's the foundation upon which multi-generational enterprises are built. Use it with intention.</p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.gentlemanspeculator.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Gentleman Speculator! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[The Stock Market Crashed]]></title><description><![CDATA[And why did you forget about Perry Como and Joe Mauer?]]></description><link>https://www.gentlemanspeculator.com/p/the-stock-market-crashed</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/the-stock-market-crashed</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Fri, 04 Apr 2025 16:06:30 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/b7169fe5-c9c5-44a1-8d3c-3d5c65cc4932_640x480.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>Thursday was one of the biggest one day blowups in the stock market that I can remember during my entire career.</p><p>Here is <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Eddy Elfenbein&quot;,&quot;id&quot;:541718,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com/public/images/93ec5df4-f788-4cab-8a47-354f118c0bbc_1688x1940.jpeg&quot;,&quot;uuid&quot;:&quot;89dcb437-57e2-4532-8bd9-ee3a1f34f337&quot;}" data-component-name="MentionToDOM"></span>:</p><blockquote><p>&#8220;President Trump declared Wednesday to be &#8220;Liberation Day.&#8221; This is when Americans would finally be released from the bootheel of unfair trade policies. Unfortunately for many investors, all they were liberated from was their money.</p><p>Thursday was the worst day for the S&amp;P 500 in nearly five years. For the day, the index lost 4.8%, and that was one of the better indexes. The Nasdaq was off by 6%, and the Russell 2000 fell 6.6%. In fact, the Russell is now in a bear market. The S&amp;P 500 High Beta Index was down more than 9%. All told, the S&amp;P 500 lost $2.4 trillion yesterday.&#8221;</p></blockquote><p>While I haven&#8217;t actually heard anyone in the real world *freaking out* yet about this decline (seriously), the internet does indeed inform me that people are *freaking out.* Considering the Trump angle, I don&#8217;t doubt this is the case. And at least in the near term, Mr. Market is telling us this is pretty bad. At around a 15% decline from the all-time highs as of this writing, it looks very possible that we go into bear territory (e.g. 20%+ decline).</p><p>I guess I like to try and strike a balance between myopic market cheerleading (&#8216;<em>Please overlords, make my portfolio go up</em>&#8217;) and black-pilled doomerism (&#8216;<em>when it all hits the fan, plastic water bottles are the common currency&#8217;</em>). History tells us there is some merit to this sort of disposition.</p><p>So with this in mind, let&#8217;s go through the venerable Investment Advisor custom of revisiting past market declines and see if we can glean any wisdom.</p><h3><strong>1929&#8211;1932: Great Depression Crash</strong></h3><p><strong>Peak:</strong> Sep 7, 1929 &#8211; S&amp;P 500 at 31.92<br> <strong>Trough:</strong> June 1, 1932 &#8211; S&amp;P falls to 4.40 (&#8722;86% total)<br> <strong>Duration:</strong> ~33 months.<a href="https://yardeni.com/wp-content/uploads/BullBearTables.pdf#:~:text=9%2F7%2F1929%2011%2F13%2F1929%2031.92%2017.66%20,34.5%20535"> Full recovery took until 1954 (25 years)</a>.</p><p><strong>What Happened:</strong> The Roaring '20s credit boom ended with the 1929 crash, triggering widespread bank failures and the Great Depression.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!SRNe!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!SRNe!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 424w, https://substackcdn.com/image/fetch/$s_!SRNe!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 848w, https://substackcdn.com/image/fetch/$s_!SRNe!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!SRNe!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!SRNe!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg" width="400" height="313" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:313,&quot;width&quot;:400,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:35873,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://www.gentlemanspeculator.com/i/160587287?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!SRNe!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 424w, https://substackcdn.com/image/fetch/$s_!SRNe!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 848w, https://substackcdn.com/image/fetch/$s_!SRNe!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!SRNe!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F9632f2db-e9f2-443d-893b-eae692d2d5df_400x313.jpeg 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><strong>Cultural Context:</strong> The #1 song was "Tiptoe Through the Tulips" by Nick Lucas; the best-selling book was All Quiet on the Western Front by Erich M. Remarque. By 1932, "Brother, Can You Spare a Dime?" captured the Depression zeitgeist.</p><h3><strong>1937&#8211;1938: Recession of 1937</strong></h3><p><strong>Peak:</strong> Mar 6, 1937 &#8211; S&amp;P at 18.68<br> <strong>Trough:</strong> Mar 31, 1938 &#8211; S&amp;P falls to 8.50 (&#8722;54% decline)<br> <strong>Duration:</strong> ~13 months.</p><p><strong>What Happened:</strong> A sharp economic relapse during Depression recovery, attributed (at the time) to Fed tightening and New Deal fiscal cuts.</p><p><strong>Cultural Context:</strong> #1 song was "Sweet Leilani" by Bing Crosby; best-selling novel was Gone with the Wind by Margaret Mitchell; MLB's top hitter was Joe Medwick (.374).</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!tTtn!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!tTtn!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 424w, https://substackcdn.com/image/fetch/$s_!tTtn!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 848w, https://substackcdn.com/image/fetch/$s_!tTtn!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 1272w, https://substackcdn.com/image/fetch/$s_!tTtn!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!tTtn!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp" width="349" height="600" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/c62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:600,&quot;width&quot;:349,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:84452,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/webp&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://www.gentlemanspeculator.com/i/160587287?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!tTtn!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 424w, https://substackcdn.com/image/fetch/$s_!tTtn!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 848w, https://substackcdn.com/image/fetch/$s_!tTtn!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 1272w, https://substackcdn.com/image/fetch/$s_!tTtn!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fc62f206e-2e76-4e3f-a291-a59e7b453bf1_349x600.webp 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><h3><strong>1940&#8211;1942: World War II Bear</strong></h3><p><strong>Peak:</strong> Oct 25, 1939 &#8211; S&amp;P around 13.2<br> <strong>Trough:</strong> Apr 28, 1942 &#8211; S&amp;P hits 7.47 (&#8722;32% from 1939 peak)<br> <strong>Duration:</strong> ~30 months.</p><p><strong>What Happened:</strong> World War II: Nazi Germany's invasions and Pearl Harbor created global crisis. The U.S. entered WWII.</p><p><strong>Cultural Context:</strong> #1 song was "Only Forever" by Bing Crosby; best-selling book was How Green Was My Valley by Richard Llewellyn. Ted Williams hit .406 in 1941 (the last .400+ season).</p><h3><strong>1946: Post-War Crash</strong></h3><p><strong>Peak:</strong> May 29, 1946 &#8211; S&amp;P 19.25<br> <strong>Trough:</strong> Oct 9, 1946 &#8211; S&amp;P 14.12 (&#8722;26.6%)<br> <strong>Duration:</strong> ~5 months. Recovery was relatively quick.</p><p><strong>What Happened:</strong> Post-war challenges included the end of wartime price controls (sparking inflation), credit tightening, and labor strikes. This "buyers' strike" punctured post-WWII exuberance.</p><p><strong>Cultural Context:</strong> #1 song was "Prisoner of Love" by Perry Como; top novel was The King's General by Daphne du Maurier; Ted Williams won the batting crown (.342) after returning from military service.</p><div id="youtube2-lbNPg_Rp0ws" class="youtube-wrap" data-attrs="{&quot;videoId&quot;:&quot;lbNPg_Rp0ws&quot;,&quot;startTime&quot;:null,&quot;endTime&quot;:null}" data-component-name="Youtube2ToDOM"><div class="youtube-inner"><iframe src="https://www.youtube-nocookie.com/embed/lbNPg_Rp0ws?rel=0&amp;autoplay=0&amp;showinfo=0&amp;enablejsapi=0" frameborder="0" loading="lazy" gesture="media" allow="autoplay; fullscreen" allowautoplay="true" allowfullscreen="true" width="728" height="409"></iframe></div></div><h3><strong>1968&#8211;1970: Vietnam/Wilderness Bear</strong></h3><p><strong>Peak:</strong> Nov 29, 1968 &#8211; S&amp;P 108.37<br> <strong>Trough:</strong> May 26, 1970 &#8211; S&amp;P 69.29 (&#8722;36% decline)<br> <strong>Duration:</strong> ~18 months.</p><p><strong>What Happened:</strong> Stagflation began. Vietnam War costs mounted, domestic unrest intensified, and inflation reached ~6% by 1969.</p><p><strong>Cultural Context:</strong> #1 song was "Hey Jude" by The Beatles; best-selling novel was Airport by Arthur Hailey; Hall of Famer Rod Carew won the AL batting title (.332) in 1969.</p><h3><strong>1973&#8211;1974: OPEC Oil Crash</strong></h3><p><strong>Peak:</strong> Jan 11, 1973 &#8211; S&amp;P 120.24<br> <strong>Trough:</strong> Oct 3, 1974 &#8211; S&amp;P 62.28 (&#8722;48.2%)<br> <strong>Duration:</strong> ~21 months. Recovery was slow, peak not regained until 1980.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!Rj4f!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!Rj4f!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 424w, https://substackcdn.com/image/fetch/$s_!Rj4f!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 848w, https://substackcdn.com/image/fetch/$s_!Rj4f!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 1272w, https://substackcdn.com/image/fetch/$s_!Rj4f!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!Rj4f!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp" width="640" height="480" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:480,&quot;width&quot;:640,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:43934,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/webp&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://www.gentlemanspeculator.com/i/160587287?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!Rj4f!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 424w, https://substackcdn.com/image/fetch/$s_!Rj4f!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 848w, https://substackcdn.com/image/fetch/$s_!Rj4f!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 1272w, https://substackcdn.com/image/fetch/$s_!Rj4f!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F765ac64b-2c2a-4b7f-9236-8cb3f27819ab_640x480.webp 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><strong>What Happened:</strong> A perfect storm: collapse of the Bretton Woods system, double-digit inflation, and the 1973 Arab Oil Embargo led to skyrocketing oil prices and deep recession. The Watergate scandal eroded. </p><p><strong>Cultural Context:</strong> #1 song was "Tie a Yellow Ribbon Round the Ole Oak Tree" by Tony Orlando &amp; Dawn (I totally forgot about this song); best-selling fiction was Jonathan Livingston Seagull by Richard Bach; MLB batting champ was Hall of Famer Rod Carew (.350 in 1974).</p><h3><strong>1987: "Black Monday" Crash</strong></h3><p><strong>Peak:</strong> Aug 25, 1987 &#8211; S&amp;P 336.77<br> <strong>Trough:</strong> Dec 4, 1987 &#8211; S&amp;P 223.92 (&#8722;33.5%)<br> <strong>Duration:</strong> ~3 months. Most damage occurred on Oct 19, 1987 &#8211; "Black Monday" &#8211; when the Dow fell 22.6% in one day.</p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!K60l!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!K60l!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 424w, https://substackcdn.com/image/fetch/$s_!K60l!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 848w, https://substackcdn.com/image/fetch/$s_!K60l!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 1272w, https://substackcdn.com/image/fetch/$s_!K60l!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!K60l!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp" width="620" height="889" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:889,&quot;width&quot;:620,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:52178,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/webp&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:&quot;https://www.gentlemanspeculator.com/i/160587287?img=https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp&quot;,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!K60l!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 424w, https://substackcdn.com/image/fetch/$s_!K60l!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 848w, https://substackcdn.com/image/fetch/$s_!K60l!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 1272w, https://substackcdn.com/image/fetch/$s_!K60l!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F64d70657-130b-4df4-9a16-3a171bf26e57_620x889.webp 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><strong>What Happened:</strong> Computerized trading &amp; market panic: After a long rally, new portfolio-insurance trading strategies led to cascade selling when concerns about rising interest rates and deficits emerged. Automated sell orders overwhelmed the system, causing the fastest crash in history.</p><p><strong>Cultural Context:</strong> #1 song in October was "Bad" by Michael Jackson; best-selling book was The Tommyknockers by Stephen King; Tony Gwynn won the batting title (.370).</p><h3><strong>2000&#8211;2002: Dot-Com Bust</strong></h3><p><strong>Peak:</strong> Mar 24, 2000 &#8211; S&amp;P 1527.46<br> <strong>Trough:</strong> Oct 9, 2002 &#8211; S&amp;P 776.76 (&#8722;49.1%). Nasdaq fell ~78%.<br> <strong>Duration:</strong> ~2&#189; years. Recovery took 7 years.</p><p><strong>What Happened:</strong> The late '90s tech mania collapsed as many unprofitable dot-com companies with sky-high valuations faltered. A mild recession in 2001 and the 9/11 terrorist attacks worsened conditions. Corporate scandals (Enron, WorldCom) further eroded trust.</p><p><strong>Cultural Context:</strong> #1 song was "Breathe" by Faith Hill; best-selling book was The Brethren by John Grisham; Nomar Garciaparra and Todd Helton tied for batting title (.372).</p><h3><strong>2007&#8211;2009: Global Financial Crisis</strong></h3><p><strong>Peak:</strong> Oct 9, 2007 &#8211; S&amp;P 1565.15<br> <strong>Trough:</strong> Mar 9, 2009 &#8211; S&amp;P 676.53 (&#8722;56.8%) &#8211; deepest drop since the Depression<br> <strong>Duration:</strong> ~17 months. Recovery to 2007 peak took 5&#189; years.</p><p><strong>What Happened:</strong> The housing bubble collapsed, triggering subprime mortgage defaults. Complex financial derivatives imploded, leading to the collapse of major firms like Bear Stearns and Lehman Brothers. The global banking crisis and Great Recession followed.</p><p><strong>Cultural Context:</strong> #1 song was "Irreplaceable" by Beyonc&#233;; best-selling book was A Thousand Splendid Suns by Khaled Hosseini; While Chipper Jones hit .364 in 2008, the great Joe Mauer would hit .365 in 2009, becoming the only catcher to secure 3 titles.</p><div id="youtube2-gLd0JqXgAGs" class="youtube-wrap" data-attrs="{&quot;videoId&quot;:&quot;gLd0JqXgAGs&quot;,&quot;startTime&quot;:null,&quot;endTime&quot;:null}" data-component-name="Youtube2ToDOM"><div class="youtube-inner"><iframe src="https://www.youtube-nocookie.com/embed/gLd0JqXgAGs?rel=0&amp;autoplay=0&amp;showinfo=0&amp;enablejsapi=0" frameborder="0" loading="lazy" gesture="media" allow="autoplay; fullscreen" allowautoplay="true" allowfullscreen="true" width="728" height="409"></iframe></div></div><h3><strong>2020: COVID-19 Crash</strong></h3><p><strong>Peak:</strong> Feb 19, 2020 &#8211; S&amp;P 3386<br> <strong>Trough:</strong> Mar 23, 2020 &#8211; S&amp;P 2237 (&#8722;33.9%)<br> <strong>Duration:</strong> Just 33 days &#8211; the fastest bear market decline ever. Full recovery by August 2020.</p><p><strong>What Happened:</strong> The COVID-19 pandemic led to worldwide lockdowns. Economic activity halted, with GDP for Q2 2020 contracting ~32% (annualized). Unprecedented fiscal and monetary stimulus (zero rates, liquidity programs, trillions in aid, helicopter money) sparked a rapid V-shaped market recovery.</p><p><strong>Cultural Context:</strong> #1 song was "Blinding Lights" by The Weeknd; best-selling book was A Promised Land by Barack Obama; DJ LeMahieu won the AL batting title (.364) in the shortened MLB season.</p><h3><strong>2022: Inflation/Fed Bear</strong></h3><p><strong>Peak:</strong> Jan 3, 2022 &#8211; S&amp;P 4796.56<br> <strong>Trough:</strong> Oct 12, 2022 &#8211; S&amp;P 3577.03 (&#8722;25.4%)<br> <strong>Duration:</strong> ~9 months.</p><p><strong>What Happened:</strong> Post-pandemic inflation surged to 40-year highs (~9% in June 2022) as stimulus-boosted demand outstripped supply. The Federal Reserve hiked interest rates at the fastest pace since the early 1980s. Russia's invasion of Ukraine spiked commodity prices, worsening inflation.</p><p><strong>Cultural Context:</strong> #1 song was "As It Was" by Harry Styles; best-selling book was It Ends with Us by Colleen Hoover as chick lit takes over; Jeff McNeil (NY Mets) won the batting title (.326).</p><p><strong>If You Stayed the Course:</strong> By Oct 2022, a $1 investment from 1929 had grown to roughly<a href="https://www.officialdata.org/us/stocks/s-p-500/1929"> $7,700 with dividends reinvested</a> &#8211; so there is evidence of long-term market resilience despite the worst drawdowns.</p><h3><strong>The Bottom Line.</strong> </h3><p>Nobody should want all-time highs every minute. It&#8217;s actually a good thing if the Fed doesn&#8217;t bail out your portfolio every time you cozy up on the La-Z-Boy to turn on MSNBC.</p><p>Take the long view. Remember that Joe Mauer MVP season, spin some Perry Como on the record player, and don&#8217;t yet count out the future of American industry because the TV tells you to.</p>]]></content:encoded></item><item><title><![CDATA[Wyatt O'Rourke - Financialization of Bitcoin, Bitcoinization of Finance]]></title><description><![CDATA[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.]]></description><link>https://www.gentlemanspeculator.com/p/wyatt-orourke-financialization-of</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/wyatt-orourke-financialization-of</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Wed, 02 Apr 2025 18:14:33 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/160438115/0f16be0d02d080a88a68d364f1f9d935.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<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&amp;P 500, NASDAQ, and gold. I then welcome <a href="https://wyattorourke.com/">Wyatt O'Rourke</a>, founder of <a href="https://basilic.io/">Basilic Financial</a> 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. </p><p>00:00 Bitcoin's Four-Year Performance Analysis</p><p>06:48 <a href="https://www.youtube.com/watch?v=odKl7lOfzC0&amp;list=PLz126cGMTd8Ra4jt2uXBPSZ02_e2WWBuT&amp;index=56">Si Bheag, Si Mhor</a> &#183; Planxty</p><p>10:26 Financialization of Bitcoin</p><p>13:20 Bitcoin Derivatives and Loan Market</p><p>27:11 The Space: A Bitcoin Citadel</p><p>37:00 Noblesse Oblige and Bitcoin</p><p>44:19 Elon Musk and Donald Trump</p>]]></content:encoded></item><item><title><![CDATA[Edward Stratemeyer & Adventures in Fiction Publishing]]></title><description><![CDATA[From The Hardy Boys to Leo & Henry]]></description><link>https://www.gentlemanspeculator.com/p/edward-stratemeyer-and-adventures</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/edward-stratemeyer-and-adventures</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Fri, 07 Mar 2025 19:58:18 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/158609650/55760d89d5cc6a728c190e365a900519.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<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, <a href="https://www.amazon.com/Quest-Lost-Sword-Adventures-Henry/dp/B0DQGRY8FV">'The Adventures of Leo and Henry.</a></p><p>Links:</p><ul><li><p>Buy <a href="https://www.amazon.com/Quest-Lost-Sword-Adventures-Henry/dp/B0DQGRY8FV">The Quest for the Lost Sword: The Adventures of Leo &amp; Henry</a></p></li><li><p>Intro: The Rocketeer (James Horner)</p></li><li><p><span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Anthony Esolen&quot;,&quot;id&quot;:40681817,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com/public/images/21680783-95c3-4d6a-9f62-9efe87775dd5_230x324.jpeg&quot;,&quot;uuid&quot;:&quot;9ed63e87-9072-4e82-8d3e-d29764708663&quot;}" data-component-name="MentionToDOM"></span> - <a href="https://tanbooks.com/products/books/defending-boyhood-how-building-forts-reading-stories-playing-ball-and-praying-to-god-can-change-the-world/?srsltid=AfmBOorhzg_nKP6BCD3hYpDX1rnjsC_HotU8VvW94q1HJG3l6uZaPchf">Defending Boyhood: How Building Forts, Reading Stories, Playing Ball, and Praying to God Can Change the World</a></p></li><li><p><span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Dave Greene&quot;,&quot;id&quot;:1884956,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substackcdn.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fbucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com%2Fpublic%2Fimages%2Fd6bb22b4-9018-4692-b5e5-9eeab0484b9d_200x186.jpeg&quot;,&quot;uuid&quot;:&quot;c32d3255-2773-4840-b4a7-dfd29d5086c0&quot;}" data-component-name="MentionToDOM"></span> - <a href="https://substack.com/@fiddlersgreene/p-148284957">An Age of Illiteracy </a></p></li><li><p>Cover art: <a href="https://passage.press/products/hb"> Passage Press - The Hardy Boys: The House on the Cliff</a></p></li><li><p>Edward Stratemeyer and the Stratemeyer syndicate - Deidre Johnson</p></li><li><p><a href="https://www.youtube.com/watch?v=O-czOkfbV9I">The Mystery of Edward Stratemeyer Documentary - Lucasfilm</a></p></li><li><p>EconTalk -<a href="https://www.econtalk.org/amor-towles-on-a-gentleman-in-moscow-and-the-writers-craft/"> Amor Towles on A Gentleman in Moscow and the Writer's Craft 8-29-22</a></p></li><li><p><span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Calmversations&quot;,&quot;id&quot;:1895409,&quot;type&quot;:&quot;pub&quot;,&quot;url&quot;:&quot;https://open.substack.com/pub/calmversations&quot;,&quot;photo_url&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/62705f81-a5df-4eda-9580-bad672915af7_1280x1280.png&quot;,&quot;uuid&quot;:&quot;4384dcd4-66a8-41aa-aaba-19c3a31df767&quot;}" data-component-name="MentionToDOM"></span> - <a href="https://www.youtube.com/watch?v=tHqPdlzxiXw">Scary Ideas- &amp; The Mainstream Legitimacy Crisis</a> - with <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Jonathan Keeperman&quot;,&quot;id&quot;:255415298,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/8acdedb4-105e-4374-b015-06baffe12c24_1000x1000.png&quot;,&quot;uuid&quot;:&quot;ee9c1cc2-f420-4dc5-856c-78413019526b&quot;}" data-component-name="MentionToDOM"></span> </p></li><li><p>Outro: The Adventures of Tintin theme</p><p></p></li></ul><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!H-4C!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fed82e7dc-41c8-4c53-a6ea-a50c6debca8f_4032x3024.jpeg" data-component-name="Image2ToDOM"><div 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sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!H-4C!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fed82e7dc-41c8-4c53-a6ea-a50c6debca8f_4032x3024.jpeg" width="1456" height="1092" 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srcset="https://substackcdn.com/image/fetch/$s_!H-4C!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fed82e7dc-41c8-4c53-a6ea-a50c6debca8f_4032x3024.jpeg 424w, https://substackcdn.com/image/fetch/$s_!H-4C!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fed82e7dc-41c8-4c53-a6ea-a50c6debca8f_4032x3024.jpeg 848w, https://substackcdn.com/image/fetch/$s_!H-4C!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fed82e7dc-41c8-4c53-a6ea-a50c6debca8f_4032x3024.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!H-4C!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fed82e7dc-41c8-4c53-a6ea-a50c6debca8f_4032x3024.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p>]]></content:encoded></item><item><title><![CDATA[2024 Investor Letter]]></title><description><![CDATA[My annual commentary for clients at Simple Wealth Planning]]></description><link>https://www.gentlemanspeculator.com/p/2024-investor-letter</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/2024-investor-letter</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Mon, 27 Jan 2025 12:30:41 GMT</pubDate><enclosure url="https://substack-post-media.s3.amazonaws.com/public/images/a3c68b7d-40b7-4689-b326-74060ddf35ac_1650x1275.png" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I am pleased to share my 2024 letter to investment clients at <a href="https://www.simplewealthkc.com/">my firm</a>, now available here for any of you who might have an interest.</p><p>In this year's letter, I comment on the firm's investment approach, '100 Baggers,' Microstrategy (MSTR), and the role of luck.</p><p>Thanks for reading!</p><p><strong><a href="https://cdn.prod.website-files.com/641943f24cf884769a1713d1/67927c71378d93d96cdad9a5_Simple%20Wealth%202024%20Annual%20Letter.pdf">Simple Wealth 2024 Investor Letter</a></strong></p><p>Best,</p><p>Andy Flattery</p><p></p><div class="subscription-widget-wrap-editor" data-attrs="{&quot;url&quot;:&quot;https://www.gentlemanspeculator.com/subscribe?&quot;,&quot;text&quot;:&quot;Subscribe&quot;,&quot;language&quot;:&quot;en&quot;}" data-component-name="SubscribeWidgetToDOM"><div class="subscription-widget show-subscribe"><div class="preamble"><p class="cta-caption">Thanks for reading Gentleman Speculator! Subscribe for free to receive new posts and support my work.</p></div><form class="subscription-widget-subscribe"><input type="email" class="email-input" name="email" placeholder="Type your email&#8230;" tabindex="-1"><input type="submit" class="button primary" value="Subscribe"><div class="fake-input-wrapper"><div class="fake-input"></div><div class="fake-button"></div></div></form></div></div>]]></content:encoded></item><item><title><![CDATA[I Wrote a Hardy Boys-esque Boys' Book]]></title><description><![CDATA[NOW AVAILABLE: The Adventures of Leo & Henry (AUDIO)]]></description><link>https://www.gentlemanspeculator.com/p/i-wrote-a-hardy-boys-esque-boys-book-467</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/i-wrote-a-hardy-boys-esque-boys-book-467</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Mon, 16 Dec 2024 08:35:39 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/153116506/1822457715e7d19e99b64b14db310a70.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p> <a href="https://www.amazon.com/dp/B0DQGRY8FV/ref=tmm_pap_swatch_0?_encoding=UTF8&amp;qid=&amp;sr=">The Adventures of Leo &amp; Henry - The Quest for the Lost Sword</a></p><p>The book is now available for purchase on <a href="https://www.amazon.com/dp/B0DQGRY8FV/ref=tmm_pap_swatch_0?_encoding=UTF8&amp;qid=&amp;sr=">Amazon</a> and <a href="https://andyflattery.gumroad.com/l/xjetx">Gumroad</a> (digital version only). </p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!hZaW!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!hZaW!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 424w, https://substackcdn.com/image/fetch/$s_!hZaW!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 848w, https://substackcdn.com/image/fetch/$s_!hZaW!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!hZaW!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!hZaW!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg" width="1456" height="2184" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:2184,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:866991,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!hZaW!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 424w, https://substackcdn.com/image/fetch/$s_!hZaW!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 848w, https://substackcdn.com/image/fetch/$s_!hZaW!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!hZaW!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F524c83fc-c56a-463b-801f-bf20b9975502_1500x2250.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p>]]></content:encoded></item><item><title><![CDATA[I Wrote a Hardy Boys-esque Boys' Book]]></title><description><![CDATA[NOW AVAILABLE: The Adventures of Leo & Henry]]></description><link>https://www.gentlemanspeculator.com/p/i-wrote-a-hardy-boys-esque-boys-book</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/i-wrote-a-hardy-boys-esque-boys-book</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Sat, 14 Dec 2024 12:24:47 GMT</pubDate><enclosure url="https://substackcdn.com/image/fetch/$s_!AHie!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg" length="0" type="image/jpeg"/><content:encoded><![CDATA[<p>I just self-published a book - <a href="https://www.amazon.com/dp/B0DQGRY8FV/ref=tmm_pap_swatch_0?_encoding=UTF8&amp;qid=&amp;sr=">The Adventures of Leo &amp; Henry - The Quest for the Lost Sword</a>. This is a boys' book, I suspect for around ages 8+, and a quick read (under 80 pages). It is also my first book and was born out of the bedtime stories I make up for my sons.</p><p>Yes, their names are Leo and Henry.. and yes, they are the heroes!</p><p>This project is also an homage to a pastiche of things I enjoyed when I was their age, satiating my own nostalgia for unabashed boys&#8217; stuff. It&#8217;s The Hardy Boys, Tom Swift Jr, and imagining what it may have been like if a young Indiana Jones were Catholic.</p><p>This particular story is a fairly straightforward adventure. When a medieval heirloom, the Sword of St. Henry (I made it up), is stolen from its rightful caretaker, the boys embark on a quest to recover it. They encounter mystery, legend, and a sinister SECRET ORDER.</p><p>The book is now available for purchase on <a href="https://www.amazon.com/dp/B0DQGRY8FV/ref=tmm_pap_swatch_0?_encoding=UTF8&amp;qid=&amp;sr=">Amazon</a> and <a href="https://andyflattery.gumroad.com/l/xjetx">Gumroad</a> (digital version only). </p><p>I am also giving away the PDF for free for those who want the bootleg version (see below).</p><p>..but wait, why is Flattery larping as an author now? Great question. The answer is that it seems kids pull unlikely things out of Dads in our desire to thrill them. So I had a lot of fun doing this and will likely be doing more, (if my audience of two demands it).</p><div class="file-embed-wrapper" data-component-name="FileToDOM"><div class="file-embed-container-reader"><div class="file-embed-container-top"><image class="file-embed-thumbnail-default" src="https://substackcdn.com/image/fetch/$s_!0Cy0!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack.com%2Fimg%2Fattachment_icon.svg"></image><div class="file-embed-details"><div class="file-embed-details-h1">The Quest For The Lost Sword Andy Flattery Bootleg Pdf</div><div class="file-embed-details-h2">7.77MB &#8729; PDF file</div></div><a class="file-embed-button wide" href="https://www.gentlemanspeculator.com/api/v1/file/1e7a4e77-cd63-41f2-9f18-56fec5c4bb23.pdf"><span class="file-embed-button-text">Download</span></a></div><a class="file-embed-button narrow" href="https://www.gentlemanspeculator.com/api/v1/file/1e7a4e77-cd63-41f2-9f18-56fec5c4bb23.pdf"><span class="file-embed-button-text">Download</span></a></div></div><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!AHie!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!AHie!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg 424w, https://substackcdn.com/image/fetch/$s_!AHie!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg 848w, 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data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:2184,&quot;width&quot;:1456,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:866991,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/jpeg&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:false,&quot;topImage&quot;:true,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!AHie!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg 424w, https://substackcdn.com/image/fetch/$s_!AHie!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg 848w, https://substackcdn.com/image/fetch/$s_!AHie!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg 1272w, https://substackcdn.com/image/fetch/$s_!AHie!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F348a145d-0a5c-4c8e-9b5c-33f3dec90214_1500x2250.jpeg 1456w" sizes="100vw" fetchpriority="high"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p></p>]]></content:encoded></item><item><title><![CDATA[Notes on Trump, Getting Unstuck, and the American Empire]]></title><description><![CDATA[I share some personal views on another Trump presidency and allow myself a moment to indulge in some optimism.]]></description><link>https://www.gentlemanspeculator.com/p/notes-on-trump-getting-unstuck-and</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/notes-on-trump-getting-unstuck-and</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Thu, 21 Nov 2024 11:32:57 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/151956951/fe0a5c5ea4451c635b3a21cbec110ca4.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<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 <a href="https://www.youtube.com/watch?v=wwJV_NuN43Y">on Bari Weiss&#8217;s show</a>, <a href="https://www.youtube.com/watch?v=kLmfyF7p0P0">Trump&#8217;s Rogan appearance</a>, Michael Goldstein <a href="https://www.youtube.com/watch?v=PBAuHv5cPl8">on the Art of Bitcoin Rhetoric</a>, the <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Kurt Steiner&quot;,&quot;id&quot;:19086169,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/0648b794-4faa-4b55-a955-0d3bdf5cbc13_400x400.jpeg&quot;,&quot;uuid&quot;:&quot;5dd7dd67-79db-4699-bf61-7009a3a8b2ee&quot;}" data-component-name="MentionToDOM"></span> piece on <a href="https://substack.com/home/post/p-149804672">American Empire: A Morale Project</a>, and <span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Isaac Simpson&quot;,&quot;id&quot;:15547569,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substackcdn.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F4abcc9dd-a931-4904-85d6-14622aa83eea_1324x1414.png&quot;,&quot;uuid&quot;:&quot;ba6ebd47-c133-4104-b7ba-6fa1d1fb21c7&quot;}" data-component-name="MentionToDOM"></span>&#8217;s piece <a href="https://www.theblaze.com/frontier/main-street">on the El Segundo Hard Tech movement</a>.&nbsp;</p><p>00:00 Body of an American - The Pogues</p><p>01:17 Thoughts on Trump </p><p>10:31 Trump's Policies&nbsp;</p><p>17:53 The Power of Memes and Bitcoin</p><p>20:50 Reflections on the Future of America</p><p>23:36 The Decline of Rome and America</p><p>27:14 The American Empire: Great and Good?</p><p>30:14 The Stagnation and Decadence of Modern America</p><p>34:15 El Segundo Hard Tech movement</p><p>38:46 The Stock Market and American Capitalism </p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!NN78!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!NN78!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 424w, https://substackcdn.com/image/fetch/$s_!NN78!,w_848,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 848w, https://substackcdn.com/image/fetch/$s_!NN78!,w_1272,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 1272w, https://substackcdn.com/image/fetch/$s_!NN78!,w_1456,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 1456w" sizes="100vw"><img src="https://substackcdn.com/image/fetch/$s_!NN78!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp" width="1000" height="1366" data-attrs="{&quot;src&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp&quot;,&quot;srcNoWatermark&quot;:null,&quot;fullscreen&quot;:null,&quot;imageSize&quot;:null,&quot;height&quot;:1366,&quot;width&quot;:1000,&quot;resizeWidth&quot;:null,&quot;bytes&quot;:208420,&quot;alt&quot;:null,&quot;title&quot;:null,&quot;type&quot;:&quot;image/webp&quot;,&quot;href&quot;:null,&quot;belowTheFold&quot;:true,&quot;topImage&quot;:false,&quot;internalRedirect&quot;:null,&quot;isProcessing&quot;:false,&quot;align&quot;:null,&quot;offset&quot;:false}" class="sizing-normal" alt="" srcset="https://substackcdn.com/image/fetch/$s_!NN78!,w_424,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 424w, https://substackcdn.com/image/fetch/$s_!NN78!,w_848,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 848w, https://substackcdn.com/image/fetch/$s_!NN78!,w_1272,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 1272w, https://substackcdn.com/image/fetch/$s_!NN78!,w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F303a67e0-e109-4759-aae5-c244a63c74b1_1000x1366.webp 1456w" sizes="100vw" loading="lazy"></picture><div class="image-link-expand"><div class="pencraft pc-display-flex pc-gap-8 pc-reset"><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container restack-image"><svg role="img" width="20" height="20" viewBox="0 0 20 20" fill="none" stroke-width="1.5" stroke="var(--color-fg-primary)" stroke-linecap="round" stroke-linejoin="round" xmlns="http://www.w3.org/2000/svg"><g><title></title><path d="M2.53001 7.81595C3.49179 4.73911 6.43281 2.5 9.91173 2.5C13.1684 2.5 15.9537 4.46214 17.0852 7.23684L17.6179 8.67647M17.6179 8.67647L18.5002 4.26471M17.6179 8.67647L13.6473 6.91176M17.4995 12.1841C16.5378 15.2609 13.5967 17.5 10.1178 17.5C6.86118 17.5 4.07589 15.5379 2.94432 12.7632L2.41165 11.3235M2.41165 11.3235L1.5293 15.7353M2.41165 11.3235L6.38224 13.0882"></path></g></svg></button><button tabindex="0" type="button" class="pencraft pc-reset pencraft icon-container view-image"><svg xmlns="http://www.w3.org/2000/svg" width="20" height="20" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round" class="lucide lucide-maximize2 lucide-maximize-2"><polyline points="15 3 21 3 21 9"></polyline><polyline points="9 21 3 21 3 15"></polyline><line x1="21" x2="14" y1="3" y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a><figcaption class="image-caption">The Kansas City Spirit - Norman Rockwell</figcaption></figure></div><p></p>]]></content:encoded></item><item><title><![CDATA[Don't Retire, Pull a Mel Gibson]]></title><description><![CDATA[Doing a Life's Work After 60, the Country Gentleman, and "Traditional" Retirement]]></description><link>https://www.gentlemanspeculator.com/p/dont-retire-pull-a-mel-gibson</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/dont-retire-pull-a-mel-gibson</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Wed, 23 Oct 2024 11:57:52 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/150579584/7df6e73919fb4ec0c876101602327ca6.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<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&#8217;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&#8217;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 &#8220;Traditional&#8221; things</p><h4>Links:&nbsp;</h4><ul><li><p>James Horner -<a href="https://www.youtube.com/watch?v=2pxFcFI6lvg"> The Legend&nbsp;</a></p></li><li><p><a href="https://www.gentlemanspeculator.com/p/why-you-should-never-retire-96a?utm_source=publication-search">This is Why You Should Never Retire</a></p></li><li><p><a href="https://youtu.be/LUQN7dZzX6E?si=PO52A61Pl4oR6-LD">Mel Gibson reveals more amazing stories live on stage in London! (IMP EPISODE 12)</a></p></li><li><p>Jim Caviezel <a href="https://www.youtube.com/watch?v=9zTJiWXf7fs">Reveals What's Happening With 'Resurrection' Film</a></p></li><li><p>Randall Wallace <a href="https://www.youtube.com/watch?v=okHM3IBRuF0">Details 'Passion of the Christ' Sequel</a></p></li><li><p><a href="https://www.youtube.com/watch?v=J38SJqZ-nYc&amp;t=50s">The Patriot</a></p></li><li><p><span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;The American Tribune&quot;,&quot;id&quot;:116484563,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substack-post-media.s3.amazonaws.com/public/images/585428bc-87c2-43fa-a47f-320eb051e082_500x500.png&quot;,&quot;uuid&quot;:&quot;6d85eaff-b2c6-4b65-be4a-ab0a8cc1dc71&quot;}" data-component-name="MentionToDOM"></span> -<strong><a href="https://www.theamericantribune.news/p/the-death-of-the-gentleman-and-the"> </a></strong><a href="https://www.theamericantribune.news/p/the-death-of-the-gentleman-and-the">The Death of the Gentleman and the Birth of Bureaucratic Tyranny</a></p></li><li><p>Oliveira - Nobility and Analogous Traditional Elites: A Theme Illuminating American Social History</p></li><li><p><span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Alaric The Barbarian&quot;,&quot;id&quot;:99435489,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://bucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com/public/images/78d68dbe-0f18-4a18-91dd-50fa86ecbe92_350x510.jpeg&quot;,&quot;uuid&quot;:&quot;299ab155-401b-4f59-8083-b45d40eec4a2&quot;}" data-component-name="MentionToDOM"></span> - <a href="https://x.com/0xAlaric/status/1836085095675105450">Things that are more &#8220;traditional&#8221; than a 32 year old SWE and a 28 year old PM buying a farm with NVIDIA gains to larp as pioneers</a></p></li><li><p><span class="mention-wrap" data-attrs="{&quot;name&quot;:&quot;Titus Techera&quot;,&quot;id&quot;:3517950,&quot;type&quot;:&quot;user&quot;,&quot;url&quot;:null,&quot;photo_url&quot;:&quot;https://substackcdn.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fbucketeer-e05bbc84-baa3-437e-9518-adb32be77984.s3.amazonaws.com%2Fpublic%2Fimages%2Fcdbb9026-4a45-40ce-9f2c-d27929b42db4_183x183.jpeg&quot;,&quot;uuid&quot;:&quot;a4f0dfdf-02cc-4bdb-9d47-983d21c02139&quot;}" data-component-name="MentionToDOM"></span> - <a href="https://lawliberty.org/the-third-wave-of-journalism/">The Third Wave of Journalism</a></p></li><li><p>James Horner - <a href="https://youtu.be/ELajXGKwQ34?si=bAmoK6XRB_QHkYke">A Gift of a Thistle</a></p></li></ul>]]></content:encoded></item><item><title><![CDATA[Leandro González-Sicilia - Multi-Generational Family Businesses, Luxury Investing, Hermès ]]></title><description><![CDATA[I welcome Leandro of Best Anchor Stocks to Gentleman Speculator.]]></description><link>https://www.gentlemanspeculator.com/p/leandro-gonzalez-sicilia-multi-generational</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/leandro-gonzalez-sicilia-multi-generational</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Mon, 07 Oct 2024 10:05:57 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/149822196/13959ed89220a1087c0c38d14d6bc4b3.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p>I welcome <a href="https://x.com/Invesquotes">Leandro</a> of <a href="https://www.bestanchorstocks.com/">Best Anchor Stocks</a> 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 Herm&#232;s. 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&#8217;s a deep researcher, and a bottom-up, long-term investor who avoids the noise. </p><p></p><p><a href="https://open.spotify.com/track/2MCBSxOnkMcVkbaLplGYjX">Great Indoors - John Mayer</a></p><p>01:28 Meet Leandro</p><p>08:09 Debunking Common Investing Tropes </p><p>12:26 The Timeless Appeal of Luxury Brands</p><p>15:27 Luxury and Social Status</p><p>22:58 Herm&#232;s</p><p>31:08 On Family-Owned, Publicly Traded Businesses</p><p></p>]]></content:encoded></item><item><title><![CDATA[Clay Finck - 100 Baggers, Quality Investing, Bitcoin for Stock Pickers]]></title><description><![CDATA[My conversation with Clay from 'We Study Billionaires']]></description><link>https://www.gentlemanspeculator.com/p/clay-finck-100-baggers-quality-investing-4bd</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/clay-finck-100-baggers-quality-investing-4bd</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Wed, 25 Sep 2024 10:00:00 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/149399622/457343def14aa5a336940b1ff0adc15b.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p>In this episode of <em>GENTLEMAN SPECULATOR</em>, I sit down with <a href="https://x.com/clay_finck">Clay Finck</a> from 'We Study Billionaires' to discuss <a href="https://www.simplewealthkc.com/post/could-bitcoin-be-a-100-bagger">Chris Mayer's book '100 Baggers,'</a> the quality investing ethos, and the friction stock analysts 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.&nbsp;</p><p>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.</p><p>03:15 Clay's Journey to the Investors Podcast</p><p>06:36 Avoiding Clickbait</p><p>10:07 Midwest small town values and investing</p><p>13:45 Chris Mayer&#8217;s &#8216;100 Baggers&#8217;</p><p>24:42 Constellation Software</p><p>32:51 Bitcoin for stock pickers</p><p>Subscribe to emails at <a href="https://www.gentlemanspeculator.com/">https://www.gentlemanspeculator.com/</a> <br><br>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. <strong><br></strong></p><div class="captioned-image-container"><figure><a class="image-link image2 is-viewable-img" target="_blank" href="https://substackcdn.com/image/fetch/$s_!Zsfu!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffa18a303-e0f2-410f-bf2d-26024c350da7_1456x816.jpeg" data-component-name="Image2ToDOM"><div class="image2-inset"><picture><source type="image/webp" srcset="https://substackcdn.com/image/fetch/$s_!Zsfu!,w_424,c_limit,f_webp,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Ffa18a303-e0f2-410f-bf2d-26024c350da7_1456x816.jpeg 424w, 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y2="10"></line><line x1="3" x2="10" y1="21" y2="14"></line></svg></button></div></div></div></a></figure></div><p><br></p>]]></content:encoded></item><item><title><![CDATA[The Real Zorro, Noblesse Oblige, Gentleman Speculator]]></title><description><![CDATA[https://www.gentlemanspeculator.com/]]></description><link>https://www.gentlemanspeculator.com/p/the-real-zorro-noblesse-oblige-gentleman-86b</link><guid isPermaLink="false">https://www.gentlemanspeculator.com/p/the-real-zorro-noblesse-oblige-gentleman-86b</guid><dc:creator><![CDATA[Andrew Flattery]]></dc:creator><pubDate>Wed, 11 Sep 2024 10:00:00 GMT</pubDate><enclosure url="https://api.substack.com/feed/podcast/149399623/f9b83c6461b80e5b9a43122daaadf0a4.mp3" length="0" type="audio/mpeg"/><content:encoded><![CDATA[<p><a href="https://www.gentlemanspeculator.com/">https://www.gentlemanspeculator.com/<br></a><br>You heard right. The Reformed Financial Advisor Podcast? It's gone. Dead and buried. From now on, it's <em>Gentleman Speculator</em>. Cleaner. Sharp as a stiletto heel. Like Alain Delon's tailored slacks.&nbsp;<br><br>Money is a tool. But this isn&#8217;t about counting beans anymore. We&#8217;re talking shadows, where the real power reveals itself. The true Zorro? It's William Lamport. And he doesn&#8217;t just fight with a sword; he fights with secrets. Bruce Wayne&#8217;s noblesse oblige? That&#8217;s not rotten lefty philanthropy&#8212;it&#8217;s blood, sweat, and munificence bestowed on a world that can't get clean.<br><br>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.<br><br>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&#8217;s all connected&#8212;sleuthing, speculating, playing the long game. And if you're not seeing the big picture, you're already yesterday's news.<br><br>But don&#8217;t expect an easy listen. The rabbit hole&#8217;s deep, one misstep and you're in free fall.&nbsp;<br><br>Welcome to Gentleman Speculator.</p><p>Subscribe to emails at <a href="https://www.gentlemanspeculator.com/">https://www.gentlemanspeculator.com/</a> <br><br>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. <strong><br></strong><br></p>]]></content:encoded></item></channel></rss>