
Gentleman Speculator
Insights on investing, legacy, and the life well-lived from Andrew Flattery and Simple Wealth Planning LLC. www.gentlemanspeculator.com
Latest episodes

Jul 3, 2024 • 46min
Writing Books, Catholic Investing, Bitcoin vs. Ethereum | Devin Rose
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, and his "there and back again" story with Bitcoin. 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 discussed in this podcast. 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

Jun 25, 2024 • 53min
Lean Entrepreneurship, Twitter, Harrison Butker | Bryant Suellentrop
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 entrepreneurial spirit and example of taking calculated baby steps in business.www.simplewealthkc.com/post/lean-entrepreneurship-twitter-harrison-butker-bryant-suellentropSubscribe 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 discussed in this podcast. 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

May 9, 2024 • 55min
Notes on Young Michael Saylor
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-saylorSubscribe 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 discussed in this podcast. 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

Feb 19, 2024 • 37min
Against 'Die with Zero'
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, guidance, and purpose. Building family wealth and nurturing intergenerational connections are ways to leave a lasting impact that extends beyond one's lifetime.Episode page: www.simplewealthkc.com/post/against-die-with-zeroSubscribe 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 discussed in this podcast. 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 22, 2023 • 1h
Building Generational Wealth: A Catholic Perspective w/ Dorian Antešić
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 generational prosperity.Episode Links:The Noblesse Oblige - Andy Flattery on Catholic Money MastermindDorian on LinkedInhttps://www.antesic.com/Good King Wenceslaus - The Irish RoversTucker Carlson - All-In PodcastSubscribe 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 discussed in this podcast. 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

Sep 21, 2023 • 59min
The Freedom to Have an Opinion | Isaiah Douglass
I have a wonderful conversation with fellow Financial Advisor, Isaiah Douglass. We discuss:Building onlineJoining Swan Private ClientAndy hates soccer/Isaiah likes soccerCOVID breaking our brainsHow FAs simp for inflationBitcoin and the american dreamEpisode page: www.simplewealthkc.com/post/the-freedom-to-have-an-opinion-isaiah-douglassSubscribe 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 discussed in this podcast. 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

Sep 6, 2023 • 55min
"Bitcoin Monasteries" & Reclaiming the American Dream | Pablo Peniche
I get into a wide ranging discussion with self-described techbro, Pablo Peniche. We discuss:Dropping out of college 3 timesA vision for how Catholic monasteries could adopt bitcoinObsessing over great cultures of the past without larpingPeter Thiel's progress & decline thesisGatsby, Elon, and fostering better elitesThe Sovereign Collective > The Sovereign IndividualEpisode Page - https://www.simplewealthkc.com/post/bitcoin-monasteries-reclaiming-the-american-dream-pablo-penicheSubscribe 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 discussed in this podcast. 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

Aug 21, 2023 • 1h 6min
John Mayer is Probably into Bitcoin | Mike Marion
Financial advisor Mike Marion joins the conversation to discuss the anti-war movement and the great Ron Paul. They then shift gears to celebrate the remarkable talent and impact of recording artist John Mayer. Topics include Mayer's relevance in today's music industry, his approach to songwriting, weaponized nostalgia, and their favorite Mayer albums.

Jul 19, 2023 • 39min
Books that Turned Me From Financial Advisor Skeptic to Bitcoin Advocate
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 GreenblattThe Driver - Garet GarrettThe Bitcoin Standard - Saifedean AmmousThe Ethics of Money Production - Guido HulsmannBitcoin is Venice - Allen Farrington & Sacha MeyersEpisode page - www.simplewealthkc.com/post/books-that-turned-me-from-financial-advisor-skeptic-to-bitcoin-advocateSubscribe 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 discussed in this podcast. 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

Jun 21, 2023 • 1h 12min
What We Have Been Reading | Brian O'Leary
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 AsbridgeCaponeThe Franco Regime - Stanley PayneStart with No - Jim CampNo B.S. Time Management for Entrepreneurs - Dan KennedyExpect to Win, Hate to Lose - Matt FureySacred Then and Sacred Now - Tom WoodsOversubscribed - Daniel PriestleyThe Political Pope - George Neumayr The Biden Deception - George NeumayrBitcoin is Venice - Allen FarringtonRestoring the family - Marian HorvatSubmission - HouellebecqGod’s Will: The Life and Works of Sr. Mary WilhelminaLeisureville - Andrew BlechmanThe Father's Son - Jim SanoThe Cypresses Believe in God - Jose Maria GironellaThe Lord of the Rings - TolkienSong of Ice & Fire - George R.R. MartinThe Iliad & The Odyssey - HomerThe Long Ships - Frans BengtssonTexas - Michener Cryptonomicon - Neal Stephenson Born Standing Up - Steve MartinThe Medieval Machine - Jean GimpelDeflation & Liberty - Guido HulsmannEating the Dinosaur - Chuck KlostermanCinema Speculation - TarantinoBrian O’Leary is an independent media personality spanning several fields—podcasting, professional copywriting, internet marketing, broadcasting, and more. The mission of this “once & future” baseball coach is to restore, build, and promote a more robust and serious culture.https://briandoleary.com/flattery/https://crisismagazine.com/podcast/sister-wilhelmina-an-american-incorruptible 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 discussed in this podcast. 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
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