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We analyze long-term stock returns when investing at market peaks and bottoms, and when stocks are cheap or expensive.
We also share what we think stocks will return over the next decade and why.
Finally, we simulate the investment outcomes for someone who invests $50 per week.
Episode Slides
Episode Transcript
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I provide a short update on Money for the Rest of Us and introduce our listener survey. All survey participants will get access to an exclusive podcast episode on my worst investing mistakes and what I learned.
Take the Money for the Rest of Us Listener Survey
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In this episode, we explore why the income we earn isn't the same as the return. We show how option income strategies work, what their historical returns have been, what drives the return, and what reasonable return expectations are.
We show why option income strategies have a positive expected return while sports betting has a negative expected return.
Finally, we look at other areas where we confuse income with the total return.
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Show Notes
Episode slide deck
Variance Risk Premia by Peter Carr and Liuren Wu—NYU
Cross section of option returns and idiosyncratic stock volatility by Jie Cao and Bing Han—The Journal of Financial Economics
The Price of Correlation Risk: Evidence from Equity Options by Joost Driessen, Pascal J. Maenhout, Grigory Vilkov—SSRN
Cross-section of option returns and volatility by Amit Goyal and Alessio Saretto—The Journal of Financial Economics
The Art of Put Selling: A 10 Year Study by John Marshall, Krag Gregory, Katherine Fogertey—Goldman Sachs
Low Stress Bets
Related Episodes
557: Don’t Fall in the Dividend Trap
549: Why Catastrophe Bonds Are Yielding 12%, and Should You Invest?
544: Sports Betting Is Not Investing
Article: Tail Events and Tail Risk
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Bad actors will use AI to disrupt the financial system, transportation networks, and utilities. We should prepare now for this inevitability. We share how in this episode. We also explain why the bull market in gold will likely continue.
Topics covered include:
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Show Notes
Episode 564 Slide Deck with Charts
Gold's Run Isn't Yet Done - Bhanu Baweja - Financial Times
Brief independent investigation of agents’ behavior, reasoning and collaboration in the OpenAI / Hugging Face hacking incident
Are Central Banks Moving Out of Dollar Assets? - Linda S. Goldberg, Oliver Hannaoui, and Sneha Parthasarathy - Federal Reserve Bank of New York
Related Episodes
541: Debasement Fears or Meme Fever? What’s Driving the Gold and Silver Rally
563: Why Interest Rates Keep Rising and What to Do About It
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The national debt exceeds $40 trillion, U.S. long-term Treasury yields are at 19-year highs, the U.S. Treasury Department is intervening in currency and bond markets. We unpack it all in this episode and show you how to position your investment portfolio to lock in higher yields and protect yourself from falling bond prices.
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Show Notes
Episode 563 Slide Deck
Debt to the Penny - U.S. Treasury
Historical debt and budget tables - U.S. White House
Average U.S. national debt interest rate - U.S. Treasury
Treasury Announces Increased Sizes of Nominal Long-End Liquidity Support Buybacks Beginning September 9 - U.S Treasury
America’s Risky Debt: What Markets See That Policymakers Don’t - Hanno Lustig
Related Episodes
525: No More AAA – What the U.S. Debt Downgrade Means for Investors
463: How to Lock in Higher Yields
464: More Ways to Lock in Higher Yields
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What are the steps to simplify your portfolio, given that it is likely spread across multiple accounts? We focus particularly on retirees, who have to weigh additional considerations like withdrawals, Roth conversions, and required minimum distributions.
We also explore which areas of the stock and bond markets are attractive right now as you seek to simplify and/or rebalance your portfolio.
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Show Notes and Related Content
A Complete Guide to Investing in I Bonds and TIPS (2026)
550: Asset Location: Where You Invest, Where You Live, What You Can Access
Free Investment Strategy Report
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We explore the expected size of AI-related debt, which vehicles hold it, what could go wrong, and how to protect yourself.
Topics covered include:
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Show Notes
AI debt slide deck used for episode
RBC Weighs $2 Billion Risk Transfer to Hedge Data Center-Linked Loans by Esteban Duarte and Paula Sambo—Bloomberg
Hyperscalers Tap External Financing as AI Capex Outruns Cash Flow—FactSet Insight
What History Tells Us About The AI Investment Boom by Larry Swedroe—Financial Advisor
Goldman Sachs Warns on AI’s Debt Tsunami — Is This the End of the AI Boom? by Rich Duprey—Yahoo! Finance
Progress and peril by Pablo Hernández de Cos—BIS
The Opportunities and Risks AI Presents for the Economy and Financial System by Governor Lisa D. Cook—The Federal Reserve
Financial Stability Report by The Board of Governors of the Federal Reserve System—The Federal Reserve
Financing the AI infrastructure boom: on- and off-balance sheet borrowing by Egemen Eren, Ingomar Krohn and Karamfil Todorov—BIS
How AI debt financing impacts duration supply and interest rates by Hugo De Vere, Srini Ramaswamy and Seth Searls—Federal Reserve Bank of Dallas
US Life Insurers Held $807 Billion of Hard-to-Sell Credit by Alexandre Rajbhandari—Bloomberg
Insurers are funding AI infrastructure – NAIC wants to know if the ratings hold up by Paul Lucas—Insurance Business
US Corporate Bonds Statistics—sifma
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How inflation numbers are manipulated to appear lower. How to change your mindset about inflation to get ahead of it.
Topics covered include:
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Money for the Rest of Us Plus
Show Notes
Preview of the 2026 Annual Update of the National Economic Accounts—BEA
The Inflation Outlook by Governor Stephen I. Miran—U.S. Federal Reserve
Toward A More Accurate Measure Of The Cost Of Living by The Advisory Commission To Study The Consumer Price Index —SSA
A Complete Guide to Understanding and Protecting Against Inflation by David Stein—Money for the Rest of Us
Live Retirement Portfolio Cohort—Money for the Rest of Us
Related Episodes
475: Inflation’s Illusion: Debunking the Normalcy of Currency Debasement
429: Which Inflation Protection Strategies Worked and Which Didn’t?
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David shares nine lessons a listener followed to become a millionaire.
Topics covered include:
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Insiders Guide Email Newsletter
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Money for the Rest of Us Plus
Related Episodes
498: What I Learned Investing in the Past Decade
454: How To Invest – Ten Rules of Thumb for Individual Investors
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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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Show Notes
Space Exploration Technologies Corp. Form S-1 Registration Statment Under the Securities Act of 1933—SEC
Elon Musk Is Dropping a Boulder in a Kiddie Pool by Matteo Wong—The Atlantic
Passive Aggressive: The Risks of Passive Investing Dominance by Chris Brightman and Campbell R. Harvey—SSRN
Passive Investing and Market Quality by Philipp Höfler, Christian Schlag, and Maik Schmeling—SSRN
Investments Mentioned
iShares Core S&P 500 ETF (IVV)
Tema S&P 500 Historical Weight ETF Strategy (DSPY)
Defiance Large Cap ex-Mag 7 (XMAG)
Invesco S&P 500 Equal Weight (RSP)
Invesco FTSE RAFI US 1000 (PRF)
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From the publisher's feed
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…
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