In which I bring you one of the sharpest minds in fundamental equity analysis, my friend Ryan O'Connor of Crossroads Capital. Ryan is a multidisciplinary thinker who combines rigorous fundamental analysis with a lot of of wit and wisdom. In this conversation, we dive deep into one of his ideas, none other than Nintendo. We discuss Ryan’s original contrarian thesis, how the business transformation has played out, and what to expect with recent release of the Switch 2. If you enjoy this discussion...
Jun 17, 2025•1 hr 24 min
I start the pod with some insights from the last four-year cycle in Bitcoin investing, comparing its annualized returns and drawdowns with other market proxies like the S&P 500, NASDAQ, and gold. I then welcome Wyatt O'Rourke , founder of Basilic Financial and author of 'The Bitcoinization of Finance,' to discuss Bitcoin's integration into traditional finance. Wyatt gets into private credit funds, Bitcoin-backed mortgages, and the importance of sound custody solutions. We then digress to a c...
Apr 02, 2025•58 min
I talk boys books passed down through generations, including classic adventure series like the Hardy Boys. I also examine the life and contributions of Edward Stratemeyer, the mastermind behind the Hardy Boys, Tom Swift, and the Bobbsey Twins. Inspired by these classics, I share my own venture in children's literature with my new book series, 'The Adventures of Leo and Henry. Links: * Buy The Quest for the Lost Sword: The Adventures of Leo & Henry * Intro: The Rocketeer (James Horner) * Anth...
Mar 07, 2025•45 min
The Adventures of Leo & Henry - The Quest for the Lost Sword The book is now available for purchase on Amazon and Gumroad (digital version only). This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.gentlemanspeculator.com...
Dec 16, 2024•2 min
I share some personal views on another Trump presidency and allow myself a moment to indulge in some optimism. We get into the concept of America's decline, comparing it to the fall of Rome, and explore the potential for continuation of the empire. I riff on the commentary of Peter Thiel on Bari Weiss’s show , Trump’s Rogan appearance , Michael Goldstein on the Art of Bitcoin Rhetoric , the Kurt Steiner piece on American Empire: A Morale Project , and Isaac Simpson ’s piece on the El Segundo Har...
Nov 21, 2024•51 min
I delve into Mel Gibson's spot-on perspective on retirement, which I contend is unnatural in the modern hedonistic context. I explore Gibson’s commitment to staying creative and active into his later years, doing work that matters, and contrast this with our societal norm of subsidized and unexamined retirement. 02:47 The Problem with Subsidized Retirement 08:23 Mel Gibson's Future Projects 14:13 The Passion of the Christ Sequel 23:26 Mel’s Redemption Arc 23:48 True Elites 25:41 The Landed Gentr...
Oct 23, 2024•45 min
I welcome Leandro of Best Anchor Stocks to Gentleman Speculator. Leandro is the co-founder of an investment research service and an equity analyst I deem worthy of paying attention to. We discuss the value of multi-generational family businesses, focusing especially on Hermès. Despite challenges, there is a small subset of public companies where being family controlled is a benefit. We talk luxury investing, how luxury brands are a reflection of human nature, and a contrast between European and ...
Oct 07, 2024•45 min
In this episode of GENTLEMAN SPECULATOR , I sit down with Clay Finck from 'We Study Billionaires' to discuss Chris Mayer's book '100 Baggers,' the quality investing ethos, and the friction stock analyst have with bitcoin. Clay shares his journey from being an actuary in Nebraska to going full time with The Investors Podcast Network. Highlights include specific companies like Copart and Constellation Software. Clay is one of the few guys I can have a conversation with about long-term investing, t...
Sep 25, 2024•48 min
https://www.gentlemanspeculator.com/ You heard right. The Reformed Financial Advisor Podcast? It's gone. Dead and buried. From now on, it's Gentleman Speculator . Cleaner. Sharp as a stiletto heel. Like Alain Delon's tailored slacks. Money is a tool. But this isn’t about counting beans anymore. We’re talking shadows, where the real power reveals itself. The true Zorro? It's William Lamport. And he doesn’t just fight with a sword; he fights with secrets. Bruce Wayne’s noblesse oblige? That’s not ...
Sep 11, 2024•45 min
In conversation again with Tim Wuebker. We discussed inflation, deflation, hard money, and the moral case for Bitcoin. I recall how the 2008 financial crisis led me to question the stability of traditional financial systems and eventually turned me towards Bitcoin, especially during the money-printing spree of 2020. We delved into the advantages of Bitcoin, such as its deflationary nature, portability, and cryptographic security, while also addressing the challenges, including its public ledger ...
Aug 06, 2024•56 min
While bitcoin is in common parlance now in market commentary, politics, and internet culture, few understand what could be an idea hiding in plain sight. This is good news for us, as herein lies the opportunity. July 2024 Special Report - Andrew Flattery Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opi...
Jul 27, 2024•20 min
I have a deep and varied conversation with Devin Rose, a Catholic author, blogger, and software engineer. We dive into topics like writing books, moral guidance for Catholic investors, and the debate between Bitcoin and Ethereum. Devin shares his personal journey from militant atheism to Catholicism, his experiences with homesteading, and his insights on investing in a way that aligns with Catholic values. Devin also talks about his various book projects, including his effort in fiction writing,...
Jul 03, 2024•46 min
In this Reformed Financial Advisor pod I talk with my friend Bryant Suellentrop, who shares his journey from from scratch to success in various businesses. Bryant reveals how he transitioned from a web design business to a profitable cleaning company and ultimately founded a recruiting agency, Elevate and Delegate. He discusses the advantages of virtual work, using twitter for business growth, and the importance of ownership in the HARRISON BUTKER story. Bryant is a good dude, I like his entrepr...
Jun 25, 2024•53 min
I dive into evolution of Michael Saylor alongside his company, MicroStrategy, illustrating Saylor's rise from humble beginnings, the establishment of MicroStrategy driven by his tech foresight, and the challenges he faced post an accounting scandal in 2000. I consider Saylor as a visionary who deftly navigates through adversities, embraces innovations like Bitcoin, displays skin in the game, and always a willingness to risk it all. Episode page: www.simplewealthkc.com/post/notes-on-young-michael...
May 09, 2024•55 min
In this episode, I delve into optimizing life while leaving a meaningful legacy. I critique the "Die With Zero" concept, popularized by Bill Perkins and others. Perkins stresses intentional living by managing time, wealth, and health effectively, but at the expense of family wealth and legacy. I also explore the societal shift towards individualism and instant gratification and contrast it with the traditional values of family and legacy. The role of the family can be in providing support, guida...
Feb 19, 2024•37 min
In this episode of The Reformed Financial Advisor podcast, I explore the topic of family wealth from a Catholic perspective. My guest is Dorian Antešić, a finance professional and Croatia's Catholic bitcoiner. We discuss his graduate school thesis on family wealth, Bitcoin, how Tucker Carlson said inheritance is a huge problem, a Benedictine monastery in Croatia, family dynasties, and the noblesse oblige. All in all an interesting conversation that combines legacy, finance, and the pursuit of ge...
Dec 22, 2023•1 hr
I have a wonderful conversation with fellow Financial Advisor, Isaiah Douglass. We discuss: Building online Joining Swan Private Client Andy hates soccer/Isaiah likes soccer COVID breaking our brains How FAs simp for inflation Bitcoin and the american dream Episode page: www.simplewealthkc.com/post/the-freedom-to-have-an-opinion-isaiah-douglass Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All op...
Sep 21, 2023•59 min
I get into a wide ranging discussion with self-described techbro, Pablo Peniche. We discuss: Dropping out of college 3 times A vision for how Catholic monasteries could adopt bitcoin Obsessing over great cultures of the past without larping Peter Thiel's progress & decline thesis Gatsby, Elon, and fostering better elites The Sovereign Collective > The Sovereign Individual Episode Page - https://www.simplewealthkc.com/post/bitcoin-monasteries-reclaiming-the-american-dream-pablo-peniche Sub...
Sep 06, 2023•55 min
I have a conversation with Mike Marion about the anti-war movement and the great Ron Paul, before we shift into a celebration of recording artist John Mayer. Mayer is one of the essential artists of the last 20 years, comparable to my muse, Jack White, and someone we can learn from too. Episode page - www.simplewealthkc.com/post/john-mayer-is-probably-into-bitcoin-mike-marion Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Regis...
Aug 21, 2023•1 hr 6 min
My descent into bitcoin madness happened gradually, then suddenly. I comment on the books that I read on my way from agnostic to bitcoin maximalist. Books discussed: The Church and the Market - A Catholic Defense of the Free Economy - Thomas E Woods Jr. You Can Be a Stock Market Genius - Joel Greenblatt The Driver - Garet Garrett The Bitcoin Standard - Saifedean Ammous The Ethics of Money Production - Guido Hulsmann Bitcoin is Venice - Allen Farrington & Sacha Meyers Episode page - www.simpl...
Jul 19, 2023•39 min
Warren Buffett says to read 500 pages a week. Yet The Atlantic recently reported that kids aren't "following in love with reading" anymore... what gives? Brian O'Leary joins me to launch a sermon on the value of reading right now and then we launch into our list. Books discussed: The Crusades - Thomas Asbridge Capone The Franco Regime - Stanley Payne Start with No - Jim Camp No B.S. Time Management for Entrepreneurs - Dan Kennedy Expect to Win, Hate to Lose - Matt Furey Sacred Then and Sacred No...
Jun 21, 2023•1 hr 12 min
Andy Flattery does a solo mixtape episode commenting on the Coen Brothers' "Hail, Caesar!," the craftsmanship of Tally Ho Yacht restoration project, and Fr. Paul Scalia's lecture on leisure, the basis of culture. In making these connections he attempts to unpack the tension between workaholism, the dignity of work, diligence, and sloth. Episode page: https://simplewealthkc.com/hail-caesar-tally-ho-yacht-guy-the-dignity-of-work-podcast/ Subscribe to emails at https://www.gentlemanspeculator.com/ ...
May 17, 2023•35 min
Trey Sellers of Unchained and Andy Flattery discuss how bitcoin relates to the Financial Independence Retire Early (FIRE) movement. Bitcoin allows individuals to hold their wealth in money itself rather than subpar assets like real estate, stocks, bonds, or gold. Sellers explains that the demonetization of assets occurs when traditional money loses value over time and individuals have to choose where to store their value. He argues that the monetary premium for these other assets, such as real e...
Apr 26, 2023•48 min
Andy Flattery & Prince Filip Karađorđević discuss the history of his storied family dynasty, dating back over two centuries, life as a royal in exile, and the promise that he sees in the Serbian people today. Filip explains why he supports bitcoin and the hope he has in leaving a family legacy for his son. Guest: HRH Prince Filip, Hereditary Prince of Serbia and Yugoslavia, also known as Prince Filip Karađorđević, is the Chief Strategy Officer at JAN3, a technology company that helps nation-...
Mar 29, 2023•49 min
Let's talk about real life boiler room stories with Wall Street veteran Chris Rossi. Show notes: https://simplewealthkc.com/confessions-of-a-stockbroker--chris-rossi-podcast/ Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertain...
Feb 22, 2023•51 min
I used to work with a regular joe who accumulated and held the same stock for decades, amassing a small fortune. His crutch- no brokerage accounts. Instead, he kept the stock certificates secured in safety deposit boxes.. Cold storage! In this episode, I unpack Chris Mayer's modern classic "100 Baggers" and consider bitcoin in light of the book's principles. Show notes: https://simplewealthkc.com/ could-bitcoin-be-a-100-bagger-podcast / Subscribe to emails at https://www.gentlemanspeculator.com/...
Jan 30, 2023•36 min
In the final episode of 2022, I unveil the most downloaded episodes of The Reformed Financial Advisor this year, read the BOOSTS, share my favorite podcasts, and shill a few book, youtube, and music recommendations. Merry Christmas & Happy New Year! Twitter thread on the most downloaded episodes of 2022: https://twitter.com/andyflattery/status/1609186663640567815?s=20&t=-441JhSU-qDqm1jwErh81A Twitter thread on my favorite podcasts of 2022: https://twitter.com/andyflattery/status/16089004...
Dec 31, 2022•45 min
Financial Advisors gather to discuss the intersection of bitcoin and financial advice. In this episode of The Reformed Financial Advisor, I chat with Morgen Rochard & Jim Crider on all things orange pilled and the RIA world: - The dead end of "trying to make money on bitcoin" - What is going well regarding tools and the regulatory environment - What is on our wish list of products & services - Why FAs should take their own advice and play the long game with bitcoin - Introducing the Bitc...
Dec 14, 2022•59 min
In this episode I speak with the FI Tax Guy, Sean Mullaney, author of the book Solo 401(k): The Solopreneurs Retirement Account . We talk: - The Tax Planning mentality - Writing a book to standout as an expert - Is Bitcoin in a 401(k) even a good idea? - What Romney SHOULD have done with his huge IRA Outro: https://www.youtube.com/watch?v=ZOaj1TCMows Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. ...
Nov 23, 2022•45 min
Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Advisor. All opinions expressed by Andy and guests are solely their own opinions and do not reflect the opinions of Simple Wealth Planning. This podcast is for informational and entertainment purposes only and should not be relied upon as investment, tax, or legal advice. Clients of Simple Wealth Planning may maintain positions in bitcoin and the securities di...
Nov 18, 2022•3 min
