Andrew Flattery
Gentleman Speculator
Insights on investing, legacy, and the life well-lived from Andrew Flattery and Flattery Wealth Management, LLC. www.gentlemanspeculator.com
Author
Andrew Flattery
Category
Podcast website
Latest episode
Jun 25, 2026
Where to listen?
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Episodes
What We Have Been Reading | Brian O'Leary 21.06.2023 1:11:50
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...
Hail, Caesar!, Tally Ho Yacht Guy, & the Dignity of Work 17.05.2023 35:11
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...
True Financial Independence | Unchained's Trey Sellers 26.04.2023 48:19
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 w...
Monarchy, Patrimony, & Bitcoin | Prince Filip of Serbia Karađorđević 29.03.2023 48:58
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 Princ...
Confessions of a Stockbroker | Chris Rossi 22.02.2023 51:17
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...
Could Bitcoin be a 100 Bagger? 30.01.2023 36:08
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:/...
Best Pods of 2022 & What I've Changed My Mind About 31.12.2022 44:53
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-qDqm1jwErh...
BTC Financial Advisor Roundtable | Morgen Rochard & Jim Crider 14.12.2022 58:36
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 &a...
Tax Planning Mentality, BTC in a 401(k), Mitt's Massive IRA | Sean Mullaney 23.11.2022 45:10
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.gentlemanspe...
A few thoughts on the FTX story 18.11.2022 3:19
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 leg...
Jack White, Tinkering, & the Limits of Goals Based Planning 07.11.2022 38:26
Factory financial advice limits high achievers. Successful people will often credit things like skills acquired, stepping stone achievements, risk taking, connections made, and luck for their greatest accomplishments. They don’t credit a goals based plan for retirement that they made 30 years ago! Instead of being laser focused on retirement, the alternative is to be a craftsman in something, have...
Speculator Work is Real Work | Bitstein 26.10.2022 58:27
Andy Flattery speaks with bitcoin legend Bitstein about the fundamental economic question - what is the social good of speculation? Contrary to popular belief, correct speculation is not a zero sum game, but serves the purpose of correcting mispriced assets. Show Notes: https://simplewealthkc.com/ speculator-work-is-real-work--bitstein-podcast / Interlude/Outro: https://www.youtube.com/watch?v=JGB...
Nuns Building Citadels & Civilization (w/ the Help of Bitcoin) 12.10.2022 45:05
I had the wonderful privilege to make a pilgrimage to the monastery of the Benedictines of Mary, Queen of the Apostles. Here are my thoughts on the visit and my conversation with Mother Abbess Cecelia. We talked about restoring civilization, growing your own food, the life of a traditional nun, the latin mass, and bitcoin charity. If you would like to help the sisters build a new monastery in sout...
Responding to Peter Mallouk's Bitcoin Critiques 26.09.2022 46:11
Andy Flattery & Zach from Casa respond to the bitcoin comments of Creative Planning's Peter Mallouk: - BTC is "Palm or Blackberry..." but blockchain will revolutionize everything? - "Too speculative" to be a currency? - But "anyone can create their own cryptocurrency?" - Investors in the S&P 500 will benefit anyway (from companies who hold it on the balan...
Inbox: Matt Fradd 401(k) Debate, Buffett's Dad, & BOOSTS 07.09.2022 32:21
In this solo episode I answer listener questions from email and boostagrams: - the Jacob Imam vs. Trent Horn 401(k) debate on Matt Fradd's Pints with Aquinas podcast - Do we hate Warren Buffett now that he hates bitcoin? - Bitcoin beginner resources - Responding to listener boostagrams Show Notes: https://simplewealthkc.com/ inbox-matt-fradd-401k-debate-buffetts-dad--boosts-podcast / Interlud...
The Michael Saylor & Robert Breedlove "What is Money?" Book | Seth Simmons 17.08.2022 45:13
Robert Breedlove partnered with Seth Simmons to produce a book version of his What is Money? The Saylor Series. In this episode, Simmons tells his story of how he was able to convert the popular podcast series into book format and why this definitive Michael Saylor appearance is significant. Support the book by participating in the giveaway for What is Money? The Saylor Series. Show Notes: https:/...
Getting Your Bitcoin Off of Coinbase | Nick Neuman 03.08.2022 45:03
" So why won't there be bitcoin banks that do this (custody) for you? I think there will be, but there's always going to be one problem with this, which is that bitcoin transactions are irreversible. And so it's an inherent core change in the security model of bitcoin compared to the legacy banking system. And because of that, there's always going to be some level of addit...
Tips for High Inflation | Tim Wuebker 21.07.2022 1:17:58
Andy Flattery & Tim Wuebker discuss all things inflation: - how we got here - why inflation is likely to stick around - what families can do to cope - what bitcoin means with an inflationary currency Originally aired on Tim Wuebker's Seemingly Ordinary Podcast Interlude & Outro: https://www.youtube.com/watch?v=dI9q6P0mYAI Subscribe to emails at https://www.gentlemanspeculator.com/ And...
Against the Index Fund Religion | Logan Bolinger 06.07.2022 47:26
Andy Flattery speaks with Logan Bolinger, attorney, writer, and founder of Think Bitcoin LLC, about the problems with Index Fund investing. Show Notes: https://simplewealthkc.com/ against-the-indexing-religion--logan-bolinger-podcast / Interlude & Outro: https://www.youtube.com/watch?v=1AxVTvrD3HY Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple...
How to Sleep Well During a Bitcoin Bear Market 15.06.2022 51:49
The party is over and bitcoin is on sale. Andy Flattery and The Orange Pill Addicts discuss best practices to follow during bitcoin bear markets. Show Notes: https://simplewealthkc.com/ how-to-sleep-well-during-a-bitcoin-bear-market-podcast / Interlude & Outro: https://www.youtube.com/watch?v=bpA_5a0miWk Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner...
The Wall Street ESG Scheme | Kyle Hill 01.06.2022 41:40
It’s the month of June, which means it’s the month where your favorite financial services provider wants to make sure that you know that they have all the allowable and respectable opinions... they support The Current Thing! This episode is a critique of "sounding good" ESG. Because behind every rainbow flag logo, every trite slogan, and all obligatory pandering, there are Wall Street mo...
Earn, Save, Reject Altcoins | Morgen Rochard 11.05.2022 45:01
Andy Flattery speaks with Financial Advisor Morgen Rochard about the basics of financial planning, why bitcoin is for families, and why Financial Advisors have gravitated towards "crypto." Show Notes: https://simplewealthkc.com/earn-save-reject-altcoins--morgen-rochard-podcast/ Subscribe to emails at https://www.gentlemanspeculator.com/ Andy Flattery is the Owner of Simple Wealth Plannin...
Answering Client Questions about Bitcoin | Trent Dudenhoeffer 13.04.2022 45:19
Trent Dudenhoeffer, CFP®, CBP helps Andy Flattery answer client questions about bitcoin. What is it? Isn't it a bubble? Doesn't it use too much energy? Isn't it like MySpace? "I don't get it." Show Notes: https://simplewealthkc.com/?p=4907 Intro music is Ryan O'Connor's Interlude & Outro: https://www.youtube.com/watch?v=bayyRPSXGq0 Follow Andy Flattery...
Saving Money is Good For Everyone 02.03.2022 29:09
A key to understanding bitcoin is to first understand the importance of savings, because everything that you hear today about savings from the "default Keynesians" is wrong. In this episode, we take a deep look into the virtue of thrift with help from The Honeymooners, Hans-Hermann Hoppe, Robinson Crusoe, Pierre Rochard, Saifedean Ammous, Jimmy Song, and Bruce Springsteen. Show notes: h...
Cronyism, Jacksonian Hard Money Movement, & "Old Bullion" | Patrick Newman 02.02.2022 44:59
Andy Flattery talks with Patrick Newman about 19th century cronyism, Thomas Hart "Old Bullion" Benton, and the parallel to today's hard money debates surrounding bitcoin. Newman is the author of "Cronyism: Liberty Vs. Power in America, 1607-1849" Show Notes: https://simplewealthkc.com/cronyism-jacksonian-hard-money-movement-old-bullion-patrick-newman-podcast/ Interlude &am...
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