555: Five Practices That Have Shaped My Career
I share five business practices that have carried me through internet bubbles, financial crises, business pivots, and now the rise of AI. 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 … [Read more...]
553: 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? 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 … [Read more...]
Portfolio Trade: Selling SMAX, Adding ILS and DBMF
552: 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. 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 … [Read more...]
551: 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. 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 … [Read more...]
Selling Gladstone Land Corp Preferred Shares
545: Burnout, Breaks, and the Courage to Spend with David Bach
David converses with best-selling author David Bach about preventing burnout through sabbaticals, moving to another country, why retirees should take Social Security as early as possible, and Bach's idea of a flat tax on IRA distributions. Show Notes David Bach's IRA Flat Tax Idea Related Episodes 506: Should You Retire Early and Live Outside Your Home Country? With Joshua Sheets Transcript Welcome to Money for the Rest of Us. This is a personal finance … [Read more...]
544: Sports Betting Is Not Investing
Can you really make money sports betting on low-risk, high-probability events? Topics covered include: The growing size and influence of the U.S. sports betting market Recent sports betting scandals How sports betting odds work An intriguing low-risk approach to sports betting Why the low-risk sports betting approach is still gambling with a negative expected return Behavioral biases that encourage sports betting Revisiting the difference between investing, … [Read more...]
543: Hoarding, FOMO, and Zcash: A Private Bitcoin
What’s the difference between hoarding and investing? There’s a reason markets built on productive assets—like stocks and bonds—are far larger than hoarding markets such as gold and cryptocurrency. In this episode, David explores why that is, and shares why he recently bought Zcash, and how it’s both similar to and different from Bitcoin. Show Notes Zcash CoinGecko The Largest Companies by Market Cap in October 2025—The Motley Fool (Accessed October 2025) DOJ Seizes $15 … [Read more...]
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