Talking Real Money - Investing Talk

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 construction over the past several decades.

The discussion also explores lessons from market history, including the importance of understanding major bear markets, determining appropriate risk levels, and building portfolios...

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 customer-service numbers, and the importance of using credit cards rather than debit cards for travel purchases. The episode is packed with practical consumer-protection advice for anyone traveling this summer.

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 when funding a major purchase from an IRA, and how investors should think about highly publicized investment opportunities.

0:05 – Roxy Butner returns to the show by...

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 attention to portfolio design than chasing the lowest possible expense ratio. They also dissect a highly tax-inefficient YieldMax fund tied to MicroStrategy an...

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 returns ignores both history and human behavior, discuss the role bonds play in managing risk and retirement income, and remind listeners that successful investing is about meeting your goals—not maximizing returns at any cost. They also answer a listener question about claiming Social Security early versus waiting until age 70 and revisit the importance of maintaining exposure to emerging markets despite their volatility.

0:12 The newest retirement “bett...

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 strategies, and the importance of diversification. They also respond to a listener defending Robinhood’s platform, debate gamification in investing, and discuss Philadelphia’s new automatic retirement savings program designed...

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 recommendations, compare Avantis and Vanguard products, answer a tax-efficient portfolio rebalancing question from a retired couple, and debunk a marketing pitch for “layered income portfo...

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 taxes, investing a potential $200,000 windfall, Roth versus traditional TSP contributions, and Paul Merriman’s popular Two-Fund for Life strategy. Along the way, Don shares his appreciation for readers of The Line Uncrossed an...

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 stabilizers rather than return generators, particularly for retirees. They also answer a listener question about covered-call ETFs, explaining how option premiums create...

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, behavioral, and retirement services provided by fiduciary advisors beyond portfolio construction. The episode concludes with a look at the growing number of highly speculative ETFs, including UFO-themed an...

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 recently retired investor concerned about market valuations and inflation, discussing small-value tilts, bond allocations, and the role of TIPS. Along the way, they wander into...

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 and market-timing assumptions to what should be a straightforward indexing approach. Listener questions cover the risks of holding 72% of retirement assets in an ESOP and whether a military...

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 maintaining a diversified portfolio and spending less than portfolio growth are the keys to retirement sustainability. He also addresses when retirees might safely move from a 4...

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 magic. Listener questions cover retirement asset allocation at age 50, the role of bonds as retirement approaches, balancing Roth and traditional retirement contributions in a high-tax state, and the surprisingly small...

Most Americans are far less prepared for retirement than many assume. Don and Tom discuss new Federal Reserve data showing that only about half of Americans have retirement accounts, the median retirement balance is just $200,000, and only a tiny percentage of retirees have more than $1 million saved. They explain why starting early, saving consistently, and avoiding speculative investing matter far more than chasing hot stocks or market trends. The episode also covers Social Security misconceptions, the challenges of retiring on limited income, concerns about Schwab’s Teen Investor Account, and the importance of teaching young people disciplined long-term investing ha...

Don and Tom tackle a Wall Street Journal financial decision-making quiz that explores how to prioritize competing goals such as retirement savings, high-interest debt, mortgages, and student loans. The discussion highlights the importance of employer matching contributions, the damaging impact of credit card debt, and the reality that many financial decisions depend on individual circumstances and risk tolerance. They then answer listener questions about retirement portfolio allocation, Fisher Investments’ sales tactics and fees, stock ownership concentration among wealthy Americans, and whether a federal retiree should consolidate TSP assets into a Vanguard IRA. The episode emphasizes building a financial plan be...

Don and Tom tackle some of the most common retirement planning mistakes, with a particular focus on taxes and the danger of becoming overly obsessed with them. They discuss taxable Social Security benefits, the importance of diversifying across account types, Roth conversion considerations, tax-loss harvesting, and why most retirement decisions ultimately fall into the category of “it depends.” They also answer a listener question about navigating poor 403(b) plan options and the advantages of a 457 plan for educators. Finally, they dive deep into a thoughtful challenge from a listener regarding Avantis and Dimensional factor funds versus traditional Vanguard index fund...

Don celebrates the continued success of the Friday Q&A format and the encouraging first week of sales for his novel The Line Uncrossed, including a strong Kirkus review, before tackling a series of listener questions centered on retirement income and fixed income investing. He explains how his combination of cash reserves, a CD ladder, and bond funds supports a disciplined withdrawal strategy, discusses why diversified bond funds like BND still play an important role in reducing portfolio volatility, rejects the idea that Social Security and pension income should be counted as bond allocations within an investment portfolio, argues...

This episode of Talking Real Money examines why financial advice so often turns into emotional debate instead of productive problem-solving. Don and Tom discuss how investors routinely underestimate spending, cling emotionally to employer stock, and defend strategies like dividend chasing, covered calls, crypto, or gold despite decades of evidence favoring diversified investing. They answer a listener question about aggressively paying down a 6.625% adjustable-rate mortgage versus maintaining liquidity, warn about commissioned advisors circling employees receiving RSU payouts, and correct a previous mistake regarding Roth employer matches under Secure 2.0 legislation. Along the way, the hosts mix humor, blunt honesty, and personal...

Tom and Don dismantle the myth of “free money” from high-dividend stocks and ETFs, explaining why chasing yield often leads to poor diversification, lower total returns, and disappointing long-term performance. Using examples like Campbell’s, Kraft Heinz, and Whirlpool, they show how dividend-paying companies can still destroy shareholder value while the broader market marches higher. The episode also features listener questions on military retirement planning with a pension-heavy income stream, asset allocation and Roth contributions near retirement, how to structure a UC retirement portfolio using low-cost index funds and small-cap value tilts, and the smartest way to generate retirement withdr...

Tom and Don tackle the impossible task of spotting market bubbles in real time, leaning on insights from Jason Zweigand Eugene Fama to argue that if bubbles were truly predictable, they wouldn’t exist. They discuss soaring semiconductor and AI-related stocks, speculative manias from tulips to SPACs to Bitcoin, and why diversification and disciplined rebalancing beat emotional market timing every time. Listener questions cover tax-loss harvesting and wash sales involving VT, VTI, and VXUS ETFs, family conversations about money, Roth conversion strategy for a wealthy near-retiree, and Dimensional’s refusal to chase hot IPOs despite the S&P 500’s changi...

Don opens the show with a deeply personal announcement: the release of his first novel, The Line Uncrossed, inspired by the life of his great-great-grandfather, a teenage Union soldier captured at Chickamauga and imprisoned at Andersonville. After sharing the journey behind the book, the episode shifts into listener Q&A covering the limited diversification benefits of international bond funds, skepticism toward direct indexing for retirees with taxable accounts, concerns about high-yield student loan investment schemes like Yrefy, ethical and practical issues surrounding Medicaid asset-protection trusts, and the surprising usefulness of adult-funded 529 plans as a backup Roth-style savings vehicle.

Don and Tom take on the uncomfortable reality that even supposedly “rules-based” index investing is starting to look suspiciously active, as major indexes like the S&P 500 consider bending long-standing rules to admit massive IPOs like SpaceX earlier than before. They explain why changing index rules matters more than most investors realize, debate whether index committees are chasing performance to stay competitive with the QQQ, and argue that broad global diversification may be safer than relying on any single benchmark. Listener questions cover retirement-saving strategies for LLC owners, how highly compensated employees can work around 401(k) discrimination limits, the pros...

Don and Tom unload on sensationalized financial journalism, taking aim at recent articles claiming the 4% withdrawal rule and classic 60/40 portfolios are “failing” retirees. They argue that the media increasingly prioritizes fear-driven headlines over practical investing wisdom, pushing emotionally charged narratives that ignore investor behavior and long-term historical returns. The duo also push back against claims that target-date funds could wipe out retirees, explaining why diversified portfolios remain far less risky than headlines suggest. Listener questions cover Robinhood’s controversial 2% transfer bonus, SEC transaction fees on ETF sales, Roth IRA liquidity concerns, rebalancing discipline, and the dangers of emotionally reacting to pol...

Tom and Don explore whether artificial intelligence is truly ready to replace financial advisors, sparked by a recent Wall Street Journal experiment using ChatGPT to build a long-term investment portfolio. They break down the AI-generated recommendations, highlighting both the surprisingly sensible use of low-cost index funds and the concerning inconsistencies, recency bias, and lack of academic factor tilts. Along the way, they discuss whether AI gives investors what they need or simply what they want, the future of fiduciary advice, and why human judgment still matters. Listener questions cover retirement planning basics, the foreign tax credit on international ETFs...

Tom and Don tackle one of retirement planning’s most misunderstood tools: reverse mortgages. Using the analogy of “selling your house in slow motion,” they explain how modern HECM reverse mortgages work, why they’ve become more regulated and potentially more useful, and why they may deserve consideration for retirees who are house-rich but cash-poor. The duo breaks down the real costs, the cash-flow benefits of eliminating a mortgage payment, and the tradeoffs between preserving home equity and improving retirement security. Listener questions cover the differences between money market funds and bond funds like Vanguard Total Bond Market ETF, ETF vers...

Don opens this Friday Q&A episode with a personal reflection on finally releasing his historical fiction novel The Line Uncrossed, inspired by his great-great-grandfather’s imprisonment at Andersonville during the Civil War. Listener questions then cover the wisdom (or insanity) of converting millions from a traditional IRA to a Roth all at once, the evolving role of “538” savings accounts, why covered calls and options strategies often disappoint despite sounding clever, skepticism over the show’s repeated praise of Avantis and Dimensional funds, and the surprisingly massive dollar amounts collected in ETF management fees. Throughout, Don leans hard into skeptici...

Don and Tom explore one of retirement’s biggest emotional and financial questions: where should you actually live once work winds down? They discuss the hidden realities behind “low-tax” retirement states, including insurance costs, healthcare expenses, weather extremes, and the importance of family and community. The episode also features listener questions on retirement cash management, why annuities often create more problems than solutions, retirement savings strategies for LLC owners, and the ultra-wealthy “buy, borrow, die” strategy using securities-backed lines of credit.

0:05 Retirement dreams and deciding where to live
1:49 The myth of “low-tax” retirement sta...

Don and Tom take aim at the booming annuity industry, arguing that most annuities are sold through fear, confusion, and unrealistic promises rather than honest financial planning. They explain why indexed annuities are especially problematic, why annuities should be viewed strictly as income tools rather than investments, and how even “good” annuities often return your own money back to you first. The episode also covers smarter retirement income strategies, including maximizing Social Security benefits, plus listener questions on “Trump accounts” and youth retirement accounts, taxable investing with DFAW vs. VT, factor investing, and whether U.S. government bonds remain safe des...

Don and Tom tackle the strange psychology of politics and investing, exploring how Republicans and Democrats consistently perceive the economy and markets differently depending on who occupies the White House. Drawing on research from Spencer Jakab, the University of Michigan, and Dimensional Fund Advisors, they argue that long-term market performance has historically shown little correlation to presidential party affiliation, despite investors’ emotional reactions. The episode also features a thoughtful listener discussion about pensions in public safety careers, including the hidden risks of not paying into Social Security and the limitations of pensions as wealth-building tools. Additional listener questions cover Va...

Tom and Don take aim at the persistent myth that active management adds meaningful long-term value, using a new study highlighted by Larry Swedroe showing that 1,260 balanced mutual funds dramatically underperformed simple low-cost index portfolios from 1990–2021. The duo contrasts expensive actively managed balanced funds with inexpensive index strategies like the Vanguard Balanced Index approach, illustrating how fees alone can devastate long-term returns. Along the way, they discuss the emotional challenge of rebalancing, the hidden costs inside broker-sold funds, and why simplicity usually beats complexity in investing. Listener questions cover paying off a high-interest HELOC, whether gold or silver make se...

This Q&A episode of Talking Real Money covers a wide range of listener questions, from proposed “youth retirement accounts” and 529 plans to the deceptive marketing tactics behind indexed annuity steak dinners. Don also shares details about his upcoming Civil War novel, The Line Uncrossed, releasing May 22. Other topics include Vanguard’s ETF stock split, the difference between quantitative investing and factor-based investing used by firms like Dimensional and Avantis, and a bizarre Apple Podcasts glitch that incorrectly labeled a recent episode as explicit content. Along the way, Don delivers a passionate takedown of indexed annuity sales tactics and marvel...

Tom takes a Wall Street Journal retirement-account quiz while Don gleefully plays game show host, leading to a surprisingly useful (and occasionally chaotic) discussion of HSAs, Roth IRAs, Trump accounts, 529 plans, contribution limits, and retirement withdrawal rules. The episode then pivots into listener questions about ACAT transfer anxiety during market volatility and a blistering takedown of indexed annuities, including misleading “bonuses,” surrender charges, and the illusion of “market returns without risk.” The show wraps with a spirited rebuttal to a listener defending annuities and a reminder that insurance companies aren’t charities—they’re math machines built to profit from your long...

Don and Tom react to the gold-pushing radio show that replaced Talking Real Money, breaking down misleading claims about gold investing, TSP accounts, and “tax-free” gold IRAs while exposing the fear-based marketing behind precious metals sales. They contrast long-term investing with speculation, discuss Jamie Dimon comments taken wildly out of context, and explain why gold’s recent surge says little about the future. Listener questions then shift the conversation toward international diversification, currency risk, sector tilts, Warren Buffett’s investing philosophy, and the dangers of overly aggressive retirement portfolios.

0:05 TRM celebrates escaping radio before being replaced...

This episode features an in-depth conversation with Justin Baer about his book House of Fidelity, exploring how Fidelity Investments helped transform investing from an elite activity into a mainstream necessity. The discussion traces Fidelity’s evolution from mutual fund pioneer to 401(k) powerhouse, highlighting its adaptability as active stock picking gave way to index investing (driven in part by figures like Jack Bogle). It also examines the firm’s surprising embrace of cryptocurrency under Abigail Johnson, as well as the complex family dynamics that shaped its leadership transition. The broader takeaway: even dominant firms must reinvent themselves—or risk becomi...

A graduation-season episode turns into a surprisingly deep conversation about careers in the age of AI, anchored by a New York Times article from Jodi Kantor. Don and Tom explore the idea that successful careers are built not by chasing trends, but by developing a personal “craft” and aligning it with real-world need. They connect that concept to investing discipline—ignore noise, focus on what you can control—and emphasize experimentation early in life. The back half pivots to listener questions, where Don dismantles buffered ETFs as overly complex, critiques commission-laden annuity practices masquerading as fiduciary advice, clarifies Social Security...

Don flies solo for a Friday Q&A, fielding questions on switching into financial services careers, the risks and reality of “enhanced” direct indexing strategies, whether newer Avantis ETFs add real value, and a classic diversification debate sparked by Markowitz and Bessembinder research. He emphasizes that financial advising is primarily a sales-driven business, warns against overly complex and leveraged investment strategies being pushed by Wall Street, reinforces the importance of broad diversification over clever stock picking, and closes by cautioning DIY retirees about the real complexity of managing withdrawals—suggesting that many would benefit from at least some level of pro...

This podcast audio was accidentally posted yesterday, so you might want to listen to our 4/29 episode, if you’ve already heard this one.

A listener-inspired revisit of emerging markets investing—sparked by the legacy of Mark Mobius—highlights why most investors are dramatically underexposed to this critical asset class. Don and Tom explain that while emerging markets bring higher volatility and currency risk, they also offer diversification, access to faster-growing economies, and exposure you simply can’t get from U.S. multinationals alone. The conversation reinforces a core principle: proper global diversification matters more than chasing...

Private equity gets sold as exclusive, sophisticated, and “what the smart money does,” but the reality is far less compelling. Don and Tom break down the illusion: limited transparency, questionable valuations, high fees, and serious liquidity risks—all for returns that barely edge out (if at all) simple public market strategies. They argue that the supposed advantages—like the “illiquidity premium” and diversification—don’t hold up under scrutiny. The episode then pivots to smart listener questions on early retirement planning and 457 vs. 401(k) decisions, reinforcing a core theme: complexity is often marketed as intelligence, but disciplined simplicity usually wins.

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