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

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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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?

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

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?

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

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

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.

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

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

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.

Should you borrow money to magnify returns in your 401 (k), IRA, or other tax-deferred retirement account?

We examine Basic Capital, which allows investors to leverage their retirement account investments.

We also explore how the wealthy don't use debt to generate wealth but to manage it. 

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Show Notes

Basic Capital

This 30-Year-Old’s Startup Is Bringing Leverage to 401(k) Savers by Suzanne Woolley—Bloomberg

This startup is offering mortgages for 401(k)s by Liz Hoffman—Semafor

Startup Failure by Elizabeth Pollman—SSRN

Related Episodes

353: The Pros and Cons of Infinite Banking and Whole Life Insurance

238: The U.S. Is More Socialist Than Denmark Regarding Home Mortgages

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As Baby Boomers continue to retire, some analysts expect financial markets to feel the strain. We examine whether demographic shifts truly shape stock and bond returns, or what other factors matter more.

Topics covered include:

• Will retiring baby boomers lead to lower stock prices or higher interest rates
• Some earlier demographic predictions and how they worked out
• How do natural interest rates reflect the demand and supply of capital
• Why demographics are only one factor that determines economic growth and financial market returns

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Show Notes

Zeihan

Harry Dent

Measuring the Natural Rate of Interest—Federal Reserve Bank of New York

Distribution of Household Wealth in the U.S. since 1989—The Federal Reserve

Related Episodes

Related Episodes

487: Are We Heading for a 2030s Depression? Global Economic and Population Shifts

445: From Boom to Bust—Why China’s Stocks Lagged Behind Its Economy & Where to Invest Next

395: How Population Trends Will Impact Growth, Inflation, Investing and Well Being

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.