Gentleman Speculator

Brian O’Leary is back on the pod to talk about the dad book. This is the airport nonfiction, narrative history, and adventure bio, etc. The Wall Street Journal just declared this ‘category’ a dying breed. As Dads with books, Brian and I draft our favorite picks. We talk Charles Manson and the CIA, why a German U-boat off the East Coast makes Shadow Divers impossible to put down, and the case for J...

Eric Jorgenson is back on the pod to talk about his new book, The Book of Elon, a five-year project distilling Elon Musk’s most useful ideas in his own words. Eric and I talk about why Musk is the greatest living entrepreneur, the recursive logic of ‘stacking S-curves,’ and the case for a generation of builders rather than financiers. Along the way: the 2008 split-the-money story, the toy casting...

I dive into what I’m calling peak America, that is the Peter McAllister (Dad) character from Home Alone . Watching this at age 41 and the movie is now a meditation on what’s worth fighting for. I get into how the McAllister house functions as a ‘castle’ for the kind of multi-generational family life that Johann Kurtz writes about in Leaving a Legacy: Inheritance, Charity, & Thousand-Year Families...

I speak with with the semi-pseudonymous Johann Kurtz on his terrific new book Leaving a Legacy: Inheritance, Charity, & Thousand-Year Families. Johann lays out the foundation for why it can be moral to leave an inheritance when pared with virtue. We talk how ‘Die with Zero’ misses the mark, why true charity is necessarily multi-generational, family business as a conduit for generational continuity...

I chat with editors Zack Grafman and Frank Theodat about the need for aspirational books for boys. Many recommendations from the Dads here, including classics like The Hardy Boys, Treasure Island, Jules Verne but also some new stuff (Redwall, How to Train your Dragon, even some video games). We also talk the (potential) opportunity within independent publishing to create and distribute through “un...

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...

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,...

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 Ques...

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

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 S...

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...

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...

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 li...

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 Wi...

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, portabi...

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...

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 Catholi...

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...

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,...

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...

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 no...

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.gentlemanspeculato...

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...

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 a...

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 Produc...