Talking Real Money - Investing Talk

Episode

• Clickbait Investing 02.07.2026 38mnt

  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:...
• Another Money Quiz 01.07.2026 33mnt

  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...
• You Can't Beat 'Em 30.06.2026 30mnt

  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 ...
• Cash Can Be Trash 29.06.2026 29mnt

  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...
• Q&A Big Day 26.06.2026 25mnt

  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...
• You Only Live Once 25.06.2026 30mnt

  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...
• They're Back... 24.06.2026 26mnt

  Tom welcomes legendary investor educator and longtime friend Paul Merriman for a wide-ranging conversation about the evolution of indexing, the proposed changes to the S&P 500, and why investors should understand both the strengths and limitations of traditional index funds. Paul explains why firms like Dimensional Fund Advisors and Avantis Investors use a more flexible, evidence-based approach than traditional indexing and discusses how academic research has reshaped portfolio constructi...
• Summer Travel Tips 23.06.2026 24mnt

  Tom welcomes consumer advocate and longtime journalist Herb Weisbaum to discuss the surprisingly expensive and increasingly chaotic summer travel season. Herb explains why airfare and travel costs remain elevated, why airline prices may not fall even if fuel costs eventually decline, and how travelers can save money through flexibility, airline perks, and smart planning. The conversation also explores travel insurance, airline schedule cuts, baggage fees, vacation-rental scams, fake airline c...
• Tom and Roxy Qs&As 22.06.2026 25mnt

  Tom welcomes back advisor Roxy Butner for a wide-ranging discussion that begins with practical financial advice for new graduates and quickly expands into questions from listeners about student loans, emergency funds, retirement savings, portfolio construction, mortgages in retirement, and the coming frenzy around a potential SpaceX IPO. Along the way, they explore the tradeoffs between debt repayment and investing, the role of small-cap value tilts in diversified portfolios, why taxes matter...
• Penny Wise? 18.06.2026 28mnt

  Don and Tom take on one of investors’ biggest blind spots: focusing on tiny costs while ignoring the factors that have a far greater impact on long-term wealth. Using a recent Jason Zweig article as a springboard, they explain how taxes can reduce stock market returns far more than the difference between low-cost fund expense ratios. The discussion covers tax-efficient investing, asset location, ETFs versus mutual funds, dividend taxation, capital gains, and why investors should pay more atte...
• Older and More Aggressive? 17.06.2026 27mnt

  NOTE: This episode was accidentally uploaded as yesterday's podcast. To make the information match, the correct podcast for 6/16 has been uploaded in yesterday's place. If you heard this episode yesterday, please check out the newest episode in the June 16th podcast preceding this one. Sorry for the error. Don and Tom take on the latest attempt to reinvent retirement investing: the claim that retirees should hold 90% stocks and just 10% bonds. They explain why focusing on recent stock return...
• Better Income? 16.06.2026 30mnt

  Should retirees live off dividends and bond interest, or use a total return strategy? Don and Tom tackle one of the most persistent myths in retirement investing: that dividend-paying stocks create safer retirement income. They explain why dividends are not “free money,” how dividend-focused portfolios can create hidden risks, and why most academic research favors a diversified total return approach. The conversation explores dividend traps, covered-call income funds, sustainable withdrawal s...
• Advice Evolution 15.06.2026 37mnt

  Don takes listeners on a journey through nearly four decades of investment advice, explaining how his thinking evolved from recommending active mutual funds in the 1980s to embracing index funds, factor investing, and eventually ETFs. Along the way, he and Tom discuss Vanguard’s rise, Don’s early relationship with Paul Merriman, the emergence of Dimensional Fund Advisors and Avantis, and why their recommendations have changed over time. They also address listener skepticism about fund recomme...
• Fewer Questions 12.06.2026 23mnt

  Don answers a diverse collection of listener questions covering Roth conversions, indexed annuities, emergency fund management, TSP contributions, inherited money, and portfolio construction. He delivers a forceful warning about indexed annuities and commission-driven insurance sales after one listener considers using an annuity bonus to offset Roth conversion taxes. Other questions explore whether short-term bond funds belong inside a Roth IRA, how much attention investors should pay to taxe...
• How Bonds Work 11.06.2026 28mnt

  Don and Tom tackle rising bond yields and the anxiety they create for investors, explaining why higher bond yields mean lower bond prices and why recent moves in long-term Treasury rates have sparked comparisons to the period before the 2008 financial crisis. They discuss inflation fears, interest rate policy, and why investors should be cautious about reading too much into bond market movements as predictors of future stock returns. The conversation reinforces the role of bonds as portfolio ...
• Hot IPOs, Cold Returns? 10.06.2026 28mnt

  Don and Tom examine the coming wave of blockbuster IPOs, including rumored offerings from SpaceX, Anthropic, and OpenAI, and explain why investor excitement often leads to disappointing results. Drawing on research from Dimensional Fund Advisors and examples such as Uber, Facebook, and Groupon, they discuss the historical underperformance of IPOs and the dangers of buying into hype. They then answer a listener’s question about assets-under-management fees, explaining the broader planning, tax...
• What is Risk? 09.06.2026 29mnt

  Don and Tom explore the difference between smart risk and dumb risk in investing, sparked by new survey data showing younger investors increasingly believe they must take big risks to achieve their financial goals. They discuss the rise in stock trading, options speculation, and meme-stock behavior, contrasting those activities with evidence-based risks such as broad stock market investing, factor tilts, and maintaining efficient use of cash. They also answer a listener question from a recent...
• Not Bogle's Vanguard 08.06.2026 34mnt

  Don and Tom question whether the investment industry—and increasingly Vanguard—keeps creating new products simply to stay relevant rather than solve real investor problems. They critique Vanguard’s new Target Retirement Lifetime Income Fund, which combines a target-date fund with an annuity, arguing that it sacrifices liquidity, introduces inflation risk, and obscures costs. They also take aim at Vanguard’s new Active/Passive Model Portfolio Series, suggesting it adds unnecessary complexity a...
• Stormy Q&A DAY 05.06.2026 22mnt

  Don records through a booming Florida thunderstorm while tackling five listener questions. He discusses a thoughtful strategy for using a UTMA account to teach investing and potentially fund a future Roth IRA, then provides a detailed overview of what goes into a true financial plan, including cash flow analysis, insurance, estate planning, tax strategy, retirement projections, and investment management. Another listener asks about investing for a long life, prompting Don to explain why maint...
• Worried About Inflation? 04.06.2026 32mnt

  Don and Tom tackle investors’ obsession with inflation protection and the financial industry’s willingness to sell expensive products that promise impossible outcomes. Using PIMCO’s Inflation Response Multi-Asset Fund as a case study, they explain why complex, high-cost inflation hedges often create more problems than they solve. The discussion explores historical inflation, why stocks remain the most effective long-term defense against rising prices, and the dangers of chasing investment mag...