
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 topics
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Show Notes
Researchers Asked LLMs for Strategic Advice. They Got “Trendslop” in Return. By Angelo Romasanta, Llewellyn D.W. Thomas and Natalia Levina—Harvard Business Review
Paul Kedrosky
Gregor Macdonald - Cold Eye Earth
Prediction Market Accuracy: Crowd Wisdom or Informed Minority? By Roberto Gomez Cram, Yunhan Guo, Theis Ingerslev Jensen, and Howard Kung
U.S. Soldier Charged With Using Classified Information To Profit From Prediction Market Bets—Office of Public Affairs, U.S. Department of Justice
64% of business books are profitable. That’s the bottom line from our study of Business Book ROI.—Josh Bernoff
Libsyn Statistics, visualized—Livewire Labs
The Big Bang: A.I. Has Created a Code Overload By Mike Isaac and Erin Griffith—The New York Times
High earners race ahead on AI as workplace divide widens By Madhumita Murgia and John Burn-Murdoch—Financial Times
Related Episodes
496: Are You Taking Enough Aspirational Risk?
535: Six Principles for Thriving Under Uncertainty and How Big Tech Is Doing the Opposite
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Apr 29
27 min

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/
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Apr 22
3 min

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.
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Show Notes
Money for the Rest of Us Live Portfolio Cohorts
Why Everything Suddenly Is ‘Perfect’ by Paula Marantz Cohen—The Wall Street Journal
Your Perfect Portfolio by Cullen Roche—Pan MacMillan
My Core Investment Values by Peter Lazaroff—Peter Lazaroff
Show Us Your Portfolio: Jared Dillian—Excess Returns: An Investing Podcast
The dystopian fantasy of uselessness by Stephen Cane—The Financial Times
Related Episodes
491: The Five Layers of Investing
306: Three Approaches to Asset Allocation
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Apr 15
27 min

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 Notes
I Saw Something New in San Francisco - Ezra Klein - New York Times
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Apr 1
7 min

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?
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Show Notes
Read Trump's full statement on Iran attacks—PBS News
I Predicted the 2008 Financial Crisis. What Is Coming May Be Worse. By Richard Bookstaber—The New York Times
The End of Theory: Financial Crises, the Failure of Economics, and the Sweep of Human Interaction By Richard Bookstaber
The Poverty of Historicism By Karl Popper
Iran Is Trying to Defeat America in the Living Room By Karim Sadjadpour—The Atlantic
Iran 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 Times
AI Isn’t Coming for Everyone’s Job By Adam Ozimek—The Atlantic
Related Episodes
291: How To Survive the Coronavirus (COVID-19) Shutdown
377: What If It’s Different This Time?
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Mar 25
27 min

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.
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Show Notes
The Upswing: How We Came Together a Century Ago and How We Can Do It Again by Robert Putnam—Simon &Schuster
An update on our model deprecation commitments for Claude Opus 3—Anthropic
Claude's Corner—Substack
Investments Mentioned
Vanguard LifeStrategy Growth Fund Investor (VASGX)
Related Episodes
542: Don’t Take Financial Advice from AI
491: The Five Layers of Investing
419: How to Make Portfolio and Asset Allocation Changes
Masterworks Disclosures
Listeners get priority access to Masterworks at https://www.Masterworks.com/david
Art 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.
Mar 11
25 min

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.
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Show Notes
2025 NACUBO-Commonfund Study of Endowments (NCSE) Results—NACUBO
Princeton University cuts expectation for endowment returns by Sun Yu—The Financial Times
Demystifying Managed Futures by Brian K. Hurst, Yao Hua Ooi, and Lasse H. Pedersen—AQR
Investments Mentioned
AQR 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 Episodes
524: Facing a Financial Squeeze: What Harvard’s Response Can Teach the Rest of Us
204: Why Are Investment Returns So Low?
180: Can You Outperform Harvard’s Endowment?
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Feb 25
27 min

In this episode, we look at asset location, how to decide which investments belong in taxable, tax-deferred, and tax-free accounts, how where we live shapes the opportunities available to us, and how capital ultimately expands our choices.
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Show Notes
The Hidden Healthcare Infrastructure Americans Cross the Border to Find—Kogod School of Business
FARMWORKER SERVICE CENTER PROPOSAL AND ACTION PLAN FOR THE CITY OF CALEXICO AND IMPERIAL VALLEY by JAVIER MORENO—Calexico
Location as an Asset by Adrien Bilal and Esteban Rossi-Hansberg—Princeton
It Is Not Climate Denial But Adaptation Denial That Holds Us Back by Mathis Wackernagel and Peter Raven—SSRN
The Overlooked Edge: The Case for Asset Location in Managed Portfolios—Morningstar
Revisiting the conventional wisdom regarding asset location by Sachin Padmawar and Daniel Jacobs—Vanguard
Asset location for equity by Sachin Padmawar and Daniel Jacobs—Vanguard
This powerful strategy can create more spendable wealth by Tom Lenkiewicz—J.P. Morgan
Asset location strategies for tax efficient investing—BlackRock
What would Yale do? Implementing after-tax asset allocation by Frances Walsh and Patrick Geddes—BlackRock
Related Episodes
540: Beyond Munis — New ETFs for Tax-Efficient Bond Investing
506: Should You Retire Early and Live Outside Your Home Country? With Joshua Sheats
425: How Profits Motivate Change
Masterworks Disclosures
Listeners get priority access to Masterworks at https://www.Masterworks.com/david
Art 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 11
23 min

A new ETF allows individuals to earn income by insuring against natural disasters through investing in catastrophe bonds. We break down the historical returns, risk, fees, and structure of this intriguing investment opportunity.
Topics covered include:What types of natural disasters are increasingHow insurance companies use reinsurance and cat bonds to protect against extreme lossesWhy home insurance premium increases should be lower in 2026How cat bonds are structured and what makes them a unique fixed income securityWhat to consider in deciding to invest in cat bonds.
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Investments Mentioned
Brookmont Catastrophic Bond ETF (ILS)
Stone Ridge High Yield Reinsurance Risk Premium Fund (SHRIX and SHRMX)
Show Notes
Miami Is Entering a State of Unreality by Mario Alejandro Ariza—The Atlantic
Historical Hurricane Tracks—NOAA
LA fires dominated insured losses of $127bn in 2025, says Aon by Eva Xiao and Lee Harris—The Financial Times
2026 Climate and Catastrophe Insight—AON
BERKSHIRE HATHAWAY INC. 2002 ANNUAL REPORT—Berkshire Hathaway
When, Where and How Often Insurers Fail—PACICC
Climate change presses on: Devastating wildfires and intense thunderstorms exacerbate losses for insurers—Munich RE
Reinsurance buyers experience market softening as reinsurers grow capital following strong returns—Guy Carpenter
Catastrophe bond sales hit record as insurers offload climate risks by Lee Harris and Ian Smith—The Financial Times
Swiss Re Global Cat Bond Performance Index returns 11.40% for 2025—Artemis
Catastrophe Bonds by Alexander Braun and Carolyn Kousky—Wharton
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Jan 28
23 min

We explore the forces likely to shape financial markets in 2026 and how to make better decisions as you pursue your goals this year.
Topics covered include:The difference between intentions and resolutionsKey behavioral biases and how to overcome themThe cautionary tale of a private real estate fund that went publicIs the affordability crisis real?The big test for AI in 2026The financial and economic outlook for the year
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Show Notes
A Slightly Better You in the New Year by Roland Fryer—The Wall Street Journal
Paying Not to Go to the Gym by Stefano DellaVigna and Ulrike Malmendier—American Economic Association
Handbook of Cognitive Biases—Federal Intelligence Service FIS
Employed full time: Median usual weekly real earnings: Wage and salary workers: 16 years and over—Federal Reserve Bank of St. Louis
America’s affordability crisis is (mostly) a mirage—The Economist
When Your Private Fund Turns $1 Into 60 Cents by Jason Zweig—The Wall Street Journal
Canadians Are Furious After Real Estate Funds Lock Up Their Money by Paula Sambo—Bloomberg
Blue Rock TI+ Annual Report—Securities and Exchange Commission
Which jobs have grown (and declined) fastest during your working life? by Andrew Van Dam—The Washington Post
Is AI More Like a Mind or a Market? by Walter Frick—Bloomberg
Don’t Fear the Bubble Bursting by Carl Benedikt Frey—The New York Times
Related Episodes
484: 7 Steps to Living a Longer Life
414: Use Caution with Private REITs like Blackstone’s BREIT
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Jan 14
32 min
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