In what may be our last quiz, ever, Tom turns the tables and puts Don in the hot seat with a Wall Street Journal high-school personal finance quiz—covering the Magnificent Seven, Roth IRAs, TIPS, efficient markets, yield curves, market risk, and dollar-cost averaging. Don does reasonably well, but not without protesting a dubious “debt avalanche” question and getting tangled up in a couple of accounting and risk terms. After the quiz-show nonsense, the guys tackle a listener question from Jos...

Tom and Don tackle one of retirement’s hardest questions: how much can you safely spend from your portfolio without blowing up the rest of your life? They walk through the familiar 4% rule, flexible withdrawal strategies, why a flat 10% withdrawal is usually fantasyland, and why the “right” spending rate depends heavily on your age, timeline, and tolerance for adjusting in bad markets. They also answer a listener question about a 22-year-old’s investment allocation and close with a timely dis...

As parents age, money can get more complicated—bill paying, account access, healthcare decisions, investment management, and eventually the possibility that someone else may need to step in. In this episode, Don and Tom walk through how families can start that conversation before a crisis hits. They cover when to begin talking, what adult children should know about accounts and spending, why durable powers of attorney need to be checked with custodians in advance, and the importance of review...

Don and Tom take on the latest crypto hype cycle, arguing that Bitcoin remains speculation—not a reliable store of wealth—and that putting crypto inside retirement accounts is especially dangerous. They discuss a new self-directed IRA crypto platform, the risks of private equity and alternative assets in retirement plans, and why “get rich quickly” pitches should set off alarm bells. Then they answer two listener questions. First, Mark from Ohio asks how to prepare a retirement portfolio for ...

Don and Tom take apart a clickbait Kiplinger piece touting the “five top buy-and-hold investments to manage market volatility,” arguing that the list is a random grab-bag of recent winners rather than a coherent portfolio. They explain why the suggested mix—VOO, VXUS, a healthcare sector ETF, Apple stock, and gold—does little to reduce volatility and instead layers on concentration risk, sector bets, and performance chasing. From there, they broaden the discussion into a more useful question:...

Can Tom beat the average American on a personal finance quiz? Don puts Tom in the hot seat with eight questions drawn from a financial literacy quiz developed by researchers at Stanford University and TIAA. The topics range from earning, budgeting, inflation, investing, debt, insurance, and risk to evaluating investment advice. Along the way, there’s plenty of good-natured ribbing, a debate over compounding, and a reminder that even financial professionals can stumble on carefully worded ques...

Don and Tom tackle the blurry line between free speech and market manipulation after the conviction of prominent short seller Andrew Left. They debate whether financial influencers should be allowed to profit from public stock recommendations, discuss why members of Congress continue trading individual stocks despite widespread public opposition, and explain why ordinary investors should avoid trying to outsmart people with superior information or influence. The conversation then shifts into ...

Are you keeping too much money in cash because you’re waiting for the “right time” to invest? In this episode, Tom and Don explain why market timing has historically been one of the costliest investing mistakes—and why even the worstinvestment timing has dramatically outperformed sitting on the sidelines. They also answer listener questions about immediate annuities, I Bonds, portfolio allocation, sequence-of-returns risk, and why using whole life insurance as an investing strategy is a bad i...

This week’s Friday Q&A is packed with six listener questions covering some of the biggest financial decisions people face before and during retirement. Topics include whether actively managed bond funds are worth the extra cost, how the new senior tax deduction may affect Roth conversions, whether a 24-year-old should keep a whole life insurance policy, financial planning before marriage, the role of mid-cap funds, and whether it’s worth abandoning a target-date fund before retirement. If...

Why do so many retirees struggle to spend money they’ve spent decades saving? Don and Tom explore the psychology behind retirement spending, including the fear of running out of money, the reluctance to touch principal, and how guaranteed income sources like Social Security, pensions, and even simple immediate annuities can make retirees more comfortable enjoying their wealth. They discuss practical strategies for creating spending confidence, the importance of comprehensive retirement planni...