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

Related Episodes

491: The Five Layers of Investing

306: Three Approaches to Asset Allocation

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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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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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Live Portfolio Cohort - May 2026

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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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