Taking Your Qs

This Friday Q&A covers real-world money decisions with real consequences, including how to invest life-insurance proceeds after a spouse’s death, why dividend-and-leverage strategies promoted online are fundamentally dangerous, and how inherited IRA rules actually work under the IRS’s 10-year framework. Don also tackles long-term HSA investing, explains why the 4% rule isn’t a one-size-fits-all solution (especially when advisor fees are involved), and even demonstrates an AI-generated version of himself to explore whether good advice can outlive the human delivering it. Equal parts practical guidance, hard math, and skeptical humor.

0:04 Friday Q&A returns, holiday illness, and how to submit questions

1:04 Investing life-insurance proceeds after a spouse’s death

1:45 Why portfolio allocation depends on income need, taxes, and risk tolerance

3:05 Why a fee-only fiduciary is essential for survivor planning

3:49 Living off dividends using leverage and margin

5:03 Why “paycheck into brokerage + leverage” strategies are dangerous

7:43 Dividend cuts, margin risk, and downturn math reality

9:29 Inherited IRA rules when the original owner had begun RMDs

11:32 The 10-year rule, annual RMDs, and IRS life-expectancy tables

12:48 Listener appreciation and the value of taking money seriously

14:01 How to invest an HSA that won’t be used for years

15:09 Adjusting the 4% rule when paying an advisor

15:54 AI voice demo, advisor value, and Vanguard’s Advisor Alpha