Gentleman Speculator

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 i...

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 ...

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 Mor...

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 ...

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...

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...

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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...

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, w...

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Andy Flattery is the Owner of Simple Wealth Planning, a Registered Investment Adv...

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 hi...

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...

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...

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 fa...

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 inter...

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 ...

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/...

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

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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
• Bitcoi...