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by J. David Stein
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- 5 days ago23 min
We Are All Wayfinders
Why we have to navigate investing, business, and life with a compass rather than a GPS. David also provides an update on what he has learned from hosting live portfolio cohorts and letting AI analyze his portfolio trades over the past 12 years.SponsorsSquare - Get up to $200 in hardwareDelete Me – Use code David20 to get 20% offInsiders Guide Email NewsletterGet our free Investors' Checklist when you sign up for the free Money for the Rest of Us email newsletterOur Premium ProductsAsset CampMoney for the Rest of Us PlusShow NotesAlmost Reckless by Amy Smilovic—Penguin Random HouseRelated Episodes555: Five Practices That Have Shaped My Career127: Investing Is WayfindingSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 2 weeks ago27 min
Five Practices That Have Shaped My Career
I share five business practices that have carried me through asset bubbles, financial crises, business pivots, and now the rise of AI.Topics covered include:Recommended note-taking app and practicesRecommended periodicalsHow to get better ideasWhy we need to understand the probabilities when pursuing a new courseThe latest insights on AI, prediction markets, and other topicsSponsorsSquare - Get up to $200 in hardwareDelete Me – Use code David20 to get 20% offLive Portfolio Cohort - May 2026Insiders Guide Email NewsletterGet our free Investors' Checklist when you sign up for the free Money for the Rest of Us email newsletterOur Premium ProductsAsset CampMoney for the Rest of Us PlusShow NotesResearchers Asked LLMs for Strategic Advice. They Got “Trendslop” in Return. By Angelo Romasanta, Llewellyn D.W. Thomas and Natalia Levina—Harvard Business ReviewPaul KedroskyGregor Macdonald - Cold Eye EarthPrediction Market Accuracy: Crowd Wisdom or Informed Minority? By Roberto Gomez Cram, Yunhan Guo, Theis Ingerslev Jensen, and Howard KungU.S. Soldier Charged With Using Classified Information To Profit From Prediction Market Bets—Office of Public Affairs, U.S. Department of Justice64% of business books are profitable. That’s the bottom line from our study of Business Book ROI.—Josh BernoffLibsyn Statistics, visualized—Livewire LabsThe Big Bang: A.I. Has Created a Code Overload By Mike Isaac and Erin Griffith—The New York TimesHigh earners race ahead on AI as workplace divide widens By Madhumita Murgia and John Burn-Murdoch—Financial TimesRelated Episodes496: Are You Taking Enough Aspirational Risk?535: Six Principles for Thriving Under Uncertainty and How Big Tech Is Doing the OppositeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 3 weeks ago3 min
Invitation to Our Live Portfolio Review and Rebalancing Special Webinar
Please attend our live webinar on portfolio construction and rebalancing scheduled for Thursday, April 30th, at 12PM Eastern, 9AM Pacific time. I will cover the five steps to constructing and rebalancing a portfolio. I will also answer your questions.You can sign up for this special webinar at https://moneyfortherestofus.com/webinar/See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- Apr 15, 202627 min
There Is No Perfect Portfolio. Just Good Enough
Why portfolio construction is messy, personal, and never perfect. We compare the pros and cons of several portfolio strategies, including target-date funds, risk parity, and role-based portfolios. We conclude with three AI-related fallacies that will help us better navigate the current moment.SponsorsSquare - Get up to $200 in hardwareDelete Me – Use code David20 to get 20% offLive Portfolio Cohort - May 2026Insiders Guide Email NewsletterGet our free Investors' Checklist when you sign up for the free Money for the Rest of Us email newsletterOur Premium ProductsAsset CampMoney for the Rest of Us PlusShow NotesMoney for the Rest of Us Live Portfolio CohortsWhy Everything Suddenly Is ‘Perfect’ by Paula Marantz Cohen—The Wall Street JournalYour Perfect Portfolio by Cullen Roche—Pan MacMillanMy Core Investment Values by Peter Lazaroff—Peter LazaroffShow Us Your Portfolio: Jared Dillian—Excess Returns: An Investing PodcastThe dystopian fantasy of uselessness by Stephen Cane—The Financial TimesInvestments MentionedState Street Bridgewater All Weather ETF (ALLW)RPAR Risk Parity ETF (RPAR)AQR Multi-Asset Fund (AQRIX)Related Episodes491: The Five Layers of Investing306: Three Approaches to Asset AllocationSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- Apr 1, 20267 min
A MFTROU Update, Cognitive Offloading Versus Cognitive Surrender, and Live Portfolio Cohorts
In this mini episode, I share some examples of how I am using Claude Cowork and other tools to boost my productivity and build investment portfolio analysis tools. I also share more details on the live portfolio cohorts we will be holding next month.You can learn more about our live portfolio cohorts here.Show NotesI Saw Something New in San Francisco - Ezra Klein - New York TimesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- Mar 25, 202627 min
Is Another Great Financial Crisis Coming? 5 Ways to Prepare
How the Iran conflict and other developments could lead to another major financial crisis. What is different today from 2008? Why trying to seed a revolution is so risky. And finally, what can we do to prepare ourselves for the next financial crisis?SponsorsDelete Me – Use code David20 to get 20% offLive Portfolio Cohort - May 2026Insiders Guide Email NewsletterGet our free Investors' Checklist when you sign up for the free Money for the Rest of Us email newsletterOur Premium ProductsAsset CampMoney for the Rest of Us PlusShow NotesRead Trump's full statement on Iran attacks—PBS NewsI Predicted the 2008 Financial Crisis. What Is Coming May Be Worse. By Richard Bookstaber—The New York TimesThe End of Theory: Financial Crises, the Failure of Economics, and the Sweep of Human Interaction By Richard BookstaberThe Poverty of Historicism By Karl PopperIran Is Trying to Defeat America in the Living Room By Karim Sadjadpour—The AtlanticIran war is the greatest threat to global energy ‘in history’, warns IEA By Malcom Moore—Financial Times‘Once and for All’ Means Never By Thomas L. Friedman—The New York TimesAI Isn’t Coming for Everyone’s Job By Adam Ozimek—The AtlanticRelated Episodes291: How To Survive the Coronavirus (COVID-19) Shutdown377: What If It’s Different This Time?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- Mar 11, 202625 min
AI Is Changing Me - and the Case for Good Enough
When is good enough actually good enough? AI is reshaping how I work and live. And a member with a portfolio that's beaten an all-in-one Vanguard LifeStrategy fund for ten years asks whether the complexity is worth it — or whether it's time to simplify.SponsorsMasterworks - Invest in multimillion-dollar artwork offeringsDelete Me – Use code David20 to get 20% offInsiders Guide Email NewsletterGet our free Investors' Checklist when you sign up for the free Money for the Rest of Us email newsletterOur Premium ProductsAsset CampMoney for the Rest of Us PlusShow NotesThe Upswing: How We Came Together a Century Ago and How We Can Do It Again by Robert Putnam—Simon &SchusterAn update on our model deprecation commitments for Claude Opus 3—AnthropicClaude's Corner—SubstackInvestments MentionedVanguard LifeStrategy Growth Fund Investor (VASGX)Related Episodes542: Don’t Take Financial Advice from AI491: The Five Layers of Investing419: How to Make Portfolio and Asset Allocation ChangesMasterworks DisclosuresListeners get priority access to Masterworks at https://www.Masterworks.com/davidArt correlation and appreciation data based on repeat-sales index of historical Post-War & Contemporary Art market prices and S&P 500 annualized return (includes dividends reinvested) from 1995 to 2025, developed by Masterworks. There are significant limitations to comparative asset class data. Indices are unmanaged and a Masterworks investor cannot invest directly in an index. Content creator (the “Endorser”) receives cash compensation from Masterworks, LLC (“Masterworks”). Endorser is a client of Masterworks. Masterworks can only make and accept sales after an offering statement has been filed, and “qualified”, by the SEC. Any offers may be revoked before notice of qualification. Indications of interest involve no obligation. Investing involves risk. Past performance not indicative of future returns. For further disclosure on Regulation A Offerings, Risks of Investing, Performance Metrics, Art Market Data, and more visit the offering documents filed with the SEC and Important Disclosures at masterworks.com/cd.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- Feb 25, 202627 min
What Average Really Looks Like — and Can Managed Futures Help?
How historical and expected returns for university endowments can guide us in setting reasonable return expectations. We also analyze managed futures strategies to see how they work, how they have performed, and how to use them in your investment portfolio.Insiders Guide Email NewsletterGet our free Investors' Checklist when you sign up for the free Money for the Rest of Us email newsletterOur Premium ProductsAsset CampMoney for the Rest of Us PlusShow Notes2025 NACUBO-Commonfund Study of Endowments (NCSE) Results—NACUBOPrinceton University cuts expectation for endowment returns by Sun Yu—The Financial TimesDemystifying Managed Futures by Brian K. Hurst, Yao Hua Ooi, and Lasse H. Pedersen—AQRInvestments MentionedAQR Managed Futures Strategy Fund I (AQMIX)iMGP DBi Managed Futures Strategy ETF (DBMF)KraneShares Mount Lucas Managed Futures Index Strategy ETF (KMLM)WisdomTree Managed Futures Strategy Fund (WTMF)First Trust Managed Futures Strategy Fund (FMF)Return Stacked US Stocks & Managed Futures ETF (RSST)Related Episodes524: Facing a Financial Squeeze: What Harvard’s Response Can Teach the Rest of Us204: Why Are Investment Returns So Low?180: Can You Outperform Harvard’s Endowment?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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About Money For the Rest of Us
A personal finance and investing podcast on money, how it works, how to invest it and how to live without worrying about it. J. David Stein is a former Chief Investment Strategist and money manager. For close to two decades, he has been teaching individuals and institutions how to invest and handle their finances in ways that are simple to understand. More info at moneyfortherestofus.com
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