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 Show Notes There are no show notes for this episode. Episode Sponsors NetSuite Delete Me – Use code David20 to get 20% … [Read more...]
558: Will You Be Forced to Own SpaceX and Other AI Stocks?
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? 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 … [Read more...]
557: Don’t Fall in the Dividend Trap
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 like MSTY, NVDY, or TSLY offered by YieldMax. Show Notes The Dividend Disconnect by Samuel M. Hartzmark and David H. Solomon—Ivey Sam Hartzmark on Dividends—Meb Faber Research The … [Read more...]
556: We Are All Wayfinders
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. Show Notes Almost Reckless by Amy Smilovic—Penguin Random House Episode Sponsors Square – Get up to $200 in hardware Delete Me – Use code David20 to get 20% off Related Episodes 555: Five Practices That Have Shaped My … [Read more...]
554: There Is No Perfect Portfolio. Just Good Enough
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. Show Notes 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 … [Read more...]
550: Asset Location: Where You Invest, Where You Live, What You Can Access
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. Show Notes The Hidden Healthcare Infrastructure Americans Cross the Border to Find—Kogod School of Business FARMWORKER SERVICE CENTER PROPOSAL AND ACTION PLAN FOR THE CITY OF CALEXICO AND IMPERIAL VALLEY by JAVIER MORENO—Calexico Location … [Read more...]
549: Why Catastrophe Bonds Are Yielding 12%, and Should You Invest?
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 lower in 2026 How cat bonds are structured … [Read more...]
548: What Will Drive Financial Markets in 2026—and How to Make It Your Best Year
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 Show Notes A Slightly Better You … [Read more...]
547: Debt Is For Managing Wealth, Not Creating It
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. Show Notes Basic Capital This 30-Year-Old’s Startup Is Bringing Leverage to 401(k) Savers by Suzanne Woolley—Bloomberg This startup is offering mortgages for 401(k)s by Liz … [Read more...]
546: Do Retiring Baby Boomers Actually Move Markets? And How Much Do Demographics Really Matter
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 capital Why demographics are only one factor that … [Read more...]
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