Money For the Rest of Us

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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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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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
Sam Hartzmark on Dividends - Meb Faber Research
The New American Hustle: Dividends Over Day Jobs - Denitsa Tsekova and Vildana Hajric - Bloomberg
Covered Calls Uncovered - Roni Israelov and Lars N. Nielsen - Financial Analysts Journal
Volatility Risk Premiums Embedded in Individual Equity Options: Some New Insights - Nikunj Kapadia and Gurdip singh Bakshi
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Investment Mentioned
Invesco S&P 500 BuyWrite ETF (PBP)
JPMorgan Equity Premium Income ETF (JEPI)
WisdomTree Equity Premium Income Fund (WTPI)
YieldMax TSLA Option Income Strategy ETF (TSLY)
Tesla (TSLA)
YieldMax NVDA Option Income Strategy ETF (NVDY)
NVIDIA (NVDA )
YieldMax MSTR Option Income Strategy ETF (MSTY)
Strategy (MSTR)
Related Episodes
471: Unlocking Income—A Comprehensive Guide to Investing in Covered Call ETFs
466: Does Dividend Investing Still Work?
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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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Show Notes
Almost Reckless by Amy Smilovic—Penguin Random House
Related Episodes
555: Five Practices That Have Shaped My Career
127: Investing Is Wayfinding

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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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Live Portfolio Cohort - May 2026
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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 Jensen, and Howard Kung
U.S. Soldier Charged With Using Classified Information To Profit From Prediction Market Bets—Office of Public Affairs, U.S. Department of Justice
64% of business books are profitable. That’s the bottom line from our study of Business Book ROI.—Josh Bernoff
Libsyn Statistics, visualized—Livewire Labs
The Big Bang: A.I. Has Created a Code Overload By Mike Isaac and Erin Griffith—The New York Times
High earners race ahead on AI as workplace divide widens By Madhumita Murgia and John Burn-Murdoch—Financial Times
Related Episodes
496: Are You Taking Enough Aspirational Risk?
535: Six Principles for Thriving Under Uncertainty and How Big Tech Is Doing the Opposite

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