Money For the Rest of Us
A personal finance and investing podcast on money, how it works, how to invest it and how to live without worrying about it. J. David Stein is a former Chief Investment Strategist and money manager. For close to two decades, he has been teaching individuals and institutions how to invest and handle their finances in ways that are simple to understand. More info at moneyfortherestofus.com
Episodes
David shares nine lessons a listener followed to become a millionaire.
Topics covered include:
- The benefit of underspending on housing
- What rate of return and how much would you need to save to grow a portfolio to one million dollars
- Why historical studies of the S&P 500 returns are misleading
- David's recent portfolio mistake
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SpaceX, Anthropic, and OpenAI are all going public. Why now? And what will their weight be in index funds? What other U.S. ETF options are there if you don't want to have such a high concentration in stocks tied to AI. And finally, if you do buy SpaceX, what would need to happen to earn a reasonable return on your investment?
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We explore the free dividend fallacy and how it applies to option income strategies. We break down the return drivers of covered call ETFs and examine the long-term performance record and volatility. Finally, we explain why it's better to own a single stock than a single-stock covered call ETF, such as MSTY, NVDY, or TSLY, offered by YieldMax.
Show Notes
The Dividend Disconnect - Samuel M. Hartzmark and David H. Solomon
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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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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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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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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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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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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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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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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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 ...
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
Spo...
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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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 capi...
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.
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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 differe...
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.
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How AI gets simple finance wrong, and how to make it work for you, not mislead you
Topics covered include:
- How AI ignores the time value of money
- A detailed example of ChatGPT misleading by making a simple math mistake
- Some examples of opportunity costs and sunk costs when making financial decisions
- Understanding how AI works can help us use it more effectively
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