- 23 minutes 20 secondsWe 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.
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Show Notes
Almost Reckless by Amy Smilovic—Penguin Random House
Related Episodes
555: Five Practices That Have Shaped My Career
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13 May 2026, 5:00 pm - 27 minutes 55 secondsFive 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 practices
- Recommended periodicals
- How to get better ideas
- Why we need to understand the probabilities when pursuing a new course
- The latest insights on AI, prediction markets, and other topics
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Live Portfolio Cohort - May 2026
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Show Notes
Gregor Macdonald - Cold Eye Earth
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
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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29 April 2026, 6:00 pm - 3 minutes 57 secondsInvitation 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.
22 April 2026, 10:00 am - 27 minutes 28 secondsThere 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.
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Live Portfolio Cohort - May 2026
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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
Investments Mentioned
State Street Bridgewater All Weather ETF (ALLW)
RPAR Risk Parity ETF (RPAR)
AQR Multi-Asset Fund (AQRIX)
Related Episodes
491: The Five Layers of Investing
306: Three Approaches to Asset Allocation
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15 April 2026, 12:00 pm - 7 minutes 6 secondsA 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 Notes
I Saw Something New in San Francisco - Ezra Klein - New York Times
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1 April 2026, 6:00 pm - 27 minutes 14 secondsIs 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?
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Show Notes
Read Trump's full statement on Iran attacks—PBS News
The Poverty of Historicism By Karl Popper
Iran Is Trying to Defeat America in the Living Room By Karim Sadjadpour—The Atlantic
‘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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25 March 2026, 6:00 pm - 25 minutes 36 secondsAI 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.
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Show Notes
An update on our model deprecation commitments for Claude Opus 3—Anthropic
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.
11 March 2026, 5:00 pm - 27 minutes 52 secondsWhat 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.
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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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25 February 2026, 6:00 pm - 23 minutes 33 secondsAsset Location: Where You Invest, Where You Live, What You Can Access
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
Location as an Asset by Adrien Bilal and Esteban Rossi-Hansberg—Princeton
The Overlooked Edge: The Case for Asset Location in Managed Portfolios—Morningstar
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
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.
11 February 2026, 6:00 pm - 23 minutes 59 secondsWhy Catastrophe Bonds Yield 12%. Should You Invest?
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 increasing
- How insurance companies use reinsurance and cat bonds to protect against extreme losses
- Why home insurance premium increases should be lower in 2026
- How cat bonds are structured and what makes them a unique fixed income security
- What 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
2026 Climate and Catastrophe Insight—AON
BERKSHIRE HATHAWAY INC. 2002 ANNUAL REPORT—Berkshire Hathaway
When, Where and How Often Insurers Fail—PACICC
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.
28 January 2026, 7:00 pm - 32 minutes 42 secondsWhat Will Drive Financial Markets in 2026—and How to Make It Your Best Year
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 resolutions
- Key behavioral biases and how to overcome them
- The cautionary tale of a private real estate fund that went public
- Is the affordability crisis real?
- The big test for AI in 2026
- The 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
Handbook of Cognitive Biases—Federal Intelligence Service FIS
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
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
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.
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