Talking Real Money - Investing Talk

Don and Tom examine the promises behind fixed, indexed, and immediate annuities—and why the word ‘guaranteed’ deserves closer scrutiny. They explain how insurers invest policyholder money, what state guaranty pools actually cover, and why complexity can hide both cost and risk. Listener questions cover when to claim Social Security, how delaying benefits can protect a surviving spouse, the interaction between Social Security COLAs and Medicare Part B premiums, and where TIPS may—or may not—be...

Higher fees do not buy higher returns. Don and Tom unpack the fee-to-risk/reward ratio, show how fund costs compound against investors, and compare low-cost index funds with expensive active funds, hedge funds, and private equity. Then they answer listener questions about converting Vanguard mutual funds to ETFs without triggering taxes, leaving a home to a stepson while preserving the step-up in basis, and spotting financial articles that are really advertisements in disguise. 3:22 The fee...

Six listener questions drive this Friday edition, starting with whether a pre-retirement car purchase belongs on a 401(k) withdrawal. Don explains why preserving tax-deferred growth usually matters more than trying to micromanage one year's tax bracket. The conversation moves through realistic return assumptions, global diversification, and the cleanest way to donate appreciated stock. Don also weighs the risks and costs of a non-traded real estate fund and reviews a thoughtfully conservative...

Retirement planning gets dangerous when people drift toward either extreme. Don and Tom unpack a survey in which savers wildly overestimate the nest egg they need, yet also assume they can safely withdraw 10% a year. The better answer is a portfolio and spending plan built for the actual person. They turn to the mechanics of retirement income: whether to take IRA distributions monthly or annually, how tax-aware withdrawals can help, and when paying cash for a large purchase makes sense. A li...

Winter comes for markets, too. Don and Tom ask the useful question before the next bear market arrives: will your portfolio—and your nerves—be ready? They revisit painful declines, concentrated bets, and why a plan matters most when selling feels irresistible. They explain how rebalancing, a sensible mix of stocks and bonds, and tax-loss harvesting can help investors respond with discipline. Your risk tolerance is only half the equation; there is no prize for taking more risk than your goals ...

Coast FI promises that if you save enough early, your retirement money can coast the rest of the way. Don and Tom run the numbers and find the missing passengers: inflation, Social Security, uncertain returns, and the messy surprises of real life. They like aggressive early saving, but not treating a projection as a guarantee—or abandoning a valuable saving habit and employer match. The listener questions cover Treasury bills versus CDs in high-tax states, California municipal bonds, and how...

Exciting investments often arrive wrapped in a great story—and hide a much bigger risk. Don and Tom revisit Financial Physics Rule 10, explain the price of chasing sizzle, and separate investing from speculation. Then they answer whether quarterly advisor check-ins are reasonable and why a sound portfolio should not require constant tinkering. They close with a conservative IRA allocation question and the tradeoffs among U.S. stocks, global diversification, and short- versus broad-term bonds...

Friday’s listener questions cover the kind of decisions that sound simple until the details arrive. Don weighs the ease of Vanguard’s total bond fund against building a Treasury ladder, and explains why convenience can be a perfectly sensible investment feature. Then it’s overseas: how much international stock exposure belongs in a diversified portfolio, and why no single U.S./international split is scientifically “right.” The show also sorts out HSA investing, beneficiaries, and the rule fo...

Americans’ 401(k) balances are hitting records—but nearly one in five workers has an outstanding plan loan. Don and Tom explain why a properly sized emergency fund should protect retirement savings from life’s inevitable surprises. They also show why TLT and other long-term Treasury funds are not cash substitutes: when rates move, long-duration bonds can swing like stocks. A diversified bond allocation, regular rebalancing, and clear buckets matter more than chasing today’s yield. Then they...

Bond prices are falling as long-term rates rise, but that doesn't mean bonds have failed. Don and Tom explain why bond prices and yields move in opposite directions, why a normal yield curve can look painful, and why the real job of bonds is stability—not stock-like returns. They compare broad intermediate-term bond funds with Treasuries, including the state-tax advantage of VGIT for some investors, and revisit the long-run case for a balanced portfolio. The bottom line: stop trying to time ...

Financial advice is everywhere, but useful investing guidance is strangely hard to find. Don and Tom sort through the stock-picking headlines, social-media hype, and finfluencers who turn excitement and fear into clicks. Then Randy sends an annuity sales presentation that makes some very large claims. The guys examine the unsupported numbers, the misleading comparisons, and why a prospectus matters more than a polished pitch. Plus, is a rising equity glide path really a cornerstone of retir...

If an investment takes longer than a minute to explain, the confusion may be doing the selling. Don and Tom examine the confusion-to-risk ratio through structured notes, CDOs, variable annuities, equity-index annuities, leverage, hidden tradeoffs, and the costly products that prosper when buyers stop asking simple questions. Then they tackle tax-gain harvesting for a child, Massachusetts municipal bonds, and RMD timing. Want more Money Music? Hear extended versions from Don’s fictional AI ba...

Retirement questions rarely have one-number answers. Don works through a couple’s ambitious retirement goal after a late start, a new retiree’s urge to attack a 7% mortgage with Roth money, and the tax-smart sale of expensive mutual funds. He also explains why target-date funds can improve real-world results, clarifies the rules for new Trump accounts, and shows how spending from a brokerage account can create room for a Roth conversion. The common thread: run the right numbers before making ...

The best portfolio cannot help much if every spare dollar disappears at checkout. Don and Tom debate practical ways to slow impulse purchases, automate saving, and build better money habits—without banning the things that make life enjoyable. A live listener call turns to TIAA and 403(b) costs, diversification, and where stocks and bonds belong across Roth and traditional accounts. Then they discuss why a pension promise depends on who stands behind it, and what investors trade when they move...

Who is looking out for insurance customers—and who is paying the people who set the standards? Don and Tom examine insurance-industry incentives, questions about the NAIC’s funding and transparency, and why consumers should ask about commissions and costs. Then a listener challenges their take on rising equity glide paths and sequence-of-returns risk. They revisit the competing research and the role of personal risk tolerance, explain AVGE’s fund-of-funds expenses, and compare a broad-market ...

Target-date funds promise a simple glide path from growth to safety—but people with the same retirement date can have completely different needs. Don and Tom compare Vanguard, Fidelity, and BlackRock funds, examine costs and stock-bond mixes, and explain why simple does not mean specific. Then they revisit decades of failed crash predictions from Rich Dad, Poor Dad author Robert Kiyosaki. Want more Money Music? Hear extended versions from Don’s fictional AI band, The Financial Fysicist, on A...

Should retirement spending pass through a Roth? Can a nonprofit offer a 401(k) with ETFs? Does active management really win overseas? Don works through a packed listener-question episode covering Roth conversions, retirement-plan rollovers, SPIVA versus Morningstar, Treasuries and CDs, dividend reinvestment in retirement, and whether a variable universal life policy still earns its keep. Want more Money Music? Hear extended versions from Don’s fictional AI band, The Financial Fysicist, on Ap...

A CFP mark reflects meaningful education, but it does not guarantee clean disciplinary history, fee-only advice, or an unwavering fiduciary relationship. Don and Tom examine the gap between reassuring credentials and the disclosures investors may find through FINRA BrokerCheck and SEC adviser records. They explain what investors should verify before hiring anyone: compensation, dual registration, product sales, disclosures, and a written fiduciary commitment. The designation can matter—but i...

An 11.15% coupon sounds irresistible—until you read the trapdoors. Don and Tom unpack a listener’s BNP Paribas auto-callable structured note and ask the question Wall Street hopes nobody asks: what actually has to happen before you get paid? The answer includes contingent coupons, the worst-performing of three indexes, a five-year lockup, bank credit risk, and a cliff where a 41% market loss can become your 41% loss. Add a 1.5% advisory fee, and this complicated promise fails the show’s favo...

Dimensional Fund Advisors founder David Booth joins Don and Tom to explain why better investing begins with accepting uncertainty instead of pretending to predict it. They discuss staying calm through frightening markets, controlling what investors can control, and why missing a rebound can permanently damage a plan. Booth also traces the evidence behind factor investing—market, size, value, and profitability—and explains why robust research must survive different countries, decades, and dat...

Risk and reward are inseparable, even when an investment pitch makes the danger hard to see. Don and Tom explain why higher expected returns require accepting uncertainty, why recent gains do not erase future losses, and why products promising market-like returns without market risk deserve skepticism. Then they answer listener questions about market odds, taxes, Chime, and finding truly fiduciary advice. Questions? Comments? Click!

It’s Friday Q&A—with a small experiment. Don slips one AI-generated voice among the listener questions and challenges you to identify the robot, with his complete two-book library hanging in the balance. The financial questions are thoroughly human: where to keep a future car fund, whether an $11,000 Roth-conversion program earns its fee, when children can fund Roth IRAs, and what happens when bond holdings move from a traditional IRA into a Roth. Don also tackles the enviable problem o...

Robinhood says it wants to be everything to investors—but its fastest-growing attractions look a lot like a casino. Don and Tom examine prediction markets, options, crypto, payment for order flow, and the uneasy fit between fiduciary advice and a brightly lit door to speculation. They explain why gamification and enormous transfer bonuses can be especially dangerous for inexperienced investors. If the goal is long-term wealth rather than entertainment, a boring, diversified custodian still b...

The market’s long winning streak has investors wondering whether a crash is waiting in the wings. Don and Tom look at the S&P 500’s run, the lost decade that followed the 1990s boom, and why international diversification changed that outcome dramatically. They also explain why market timing asks the impossible: missing the worst days sounds wonderful, but missing the best days can be devastating. The less theatrical answer is still the useful one—make a plan, understand your tolerance fo...

Wall Street has declared yet another “year of the stock picker.” Don and Tom examine Morningstar and SPIVA data showing how few active large-cap funds beat their benchmarks—and why high fees, trading costs, taxes, short horizons, and fierce competition keep the odds tilted toward low-cost diversification. Then Greg asks where stocks and bonds belong while he begins Roth conversions. The discussion covers asset location, small-cap value exposure, international diversification, tax brackets, I...

Rule Seven of Financial Physics says there is no new news: by the time public information reaches you, the market has already reacted. Don and Tom explain why neither headlines nor illegal insider tips offer ordinary investors a durable edge, why fast trading and miracle systems disappoint, and why accepting market returns is the saner path. Then they compare JAAA with BND, help a student balance FAFSA concerns with emergency savings and a Roth IRA, warn against reaching for yield, and unta...

Friday’s question pile ranges from the safest bond fund around to the harder question of what retirement is actually for. Don sorts through the choices with his usual preference for simple, sturdy answers. He weighs the TSP G Fund against BND, checks the bona fides of Raisin and The College Investor, and argues that leaving work makes sense only when something better is waiting on the other side. Then comes a candid disagreement over 21-fund portfolios, followed by a pension decision for a ...

Being great at running a company does not make anyone a market oracle. Don and Tom unpack the money regrets of successful CEOs—and the costly confidence that often follows success. They draw the line between business skill and investment skill, explain why financial literacy matters, and make the case for diversification over hindsight, stock-picking games, and concentrated bets. Then they turn to listener questions on catching up at 43, investing a church endowment, an underperforming robo...

Could a nation of steadier 401(k) investors make markets calmer—or will algorithms, options, and meme-stock behavior keep the ride bumpy? Tom and Roxy weigh the forces pulling volatility in both directions. Next, an almost-80-year-old with a $4 million portfolio asks who should coordinate the inheritance plan. The answer is a team effort, with the financial advisor calling the plays and the CPA and estate attorney handling their specialties. They also decode RIA versus IAR, flag the conflic...

AI’s appetite for data centers is sending tech giants to the bond market—and some of that debt will still be around in 2075. Don and Tom look at the scale of the borrowing and why a tempting yield deserves a closer look. They separate coupon rate from yield to maturity, explain senior unsecured debt, and show how brutally interest-rate-sensitive a 50-year bond can be. The verdict: these bonds may belong in a broad index, but they don’t belong on your personal shopping list. Listener questio...

Why is financial forecasting so persuasive when its track record is so poor? Don and Tom open the Book of Financial Physics to Law No. 6—“Nobody Knows Nothing”—and explain why stock pickers, market timers, and highly paid pundits cannot reliably tell you what comes next. Then they answer listener questions about permanent life insurance and deferred income annuities, trusted contacts and two-factor authentication, and whether a wealthy client can copy an advisor’s portfolio while paying for ...

Required minimum distributions don’t have to trigger a fire sale. Don explains how an in-kind transfer can move an investment from an IRA to a brokerage account while preserving the holding and resetting its cost basis. Then it’s back to school: a cut-off Coverdell question, the unusual strength of the TSP G Fund, and a surprisingly useful 4% money market account that can behave a lot like checking. The finale sorts out UTMA 529 rules, beneficiary control, and why a low-cost age-based portf...

Wall Street can promise dazzling returns, but private equity’s fees, illiquidity, and tax drag may leave investors with far less than the headline number. Don and Tom unpack research showing how ordinary index funds and municipal bonds can deliver comparable after-tax results with much less risk. Then a startling poll claims many Americans believe stocks only help the richest—and that gambling may beat investing. The hosts push back with the math, then tackle when taxable brokerage accounts ...

Fresh from passing the CFP exam, Roxy Butner joins Tom to work through a classic retirement fork: take the richer lifetime teacher pension, or accept a $315,000 lump sum and invest it. The math matters, but so do longevity, survivor benefits, liquidity, investing temperament, and the temptation to spend the pile. Next comes a clever tax-payment question: can IRA withholding replace quarterly estimated payments during Roth-conversion years? They explain why paying conversion taxes from taxabl...

Just when you thought America had invented every possible retirement account, along comes the Radish. Don and Tom dig into the proposed employer-funded savings plan, the man who helped create the 401(k), and whether workers really need another tax-advantaged vegetable in an already crowded garden. The practical answer is simpler: start saving now. A Roth IRA and one broad global stock ETF can do more good than waiting for the perfect account—or learning every acronym in the retirement alphab...

Financial Physics rule five asks the uncomfortable question every investor should answer: what is the worst that could happen? Don and Tom revisit leverage in 1929, the crashes of 2000, 2008, and 2020, and the practical defenses that keep a bad market from becoming a ruined plan. Then the questions turn to retirement planning: managing IRMAA while considering Roth conversions, weighing long-term-care insurance against self-insuring, and judging whether a $1.6 million portfolio can support a ...

Don opens with a spirited defense of AI as a creative tool—especially when it makes ideas possible that would otherwise be too expensive or time-consuming. Technology changes the jobs around us, but learning to direct it responsibly can expand what one person can make. Then it’s on to listener questions: how charitable giving from a retirement account might work better through an IRA and qualified charitable distributions, whether dividends and bond interest should be reinvested, and why mon...

Chargebacks were built to protect consumers from stolen cards and crooked merchants. Now they’re increasingly used when a subscription surprises someone, a restaurant disappoints, or buyer’s remorse sets in. Don and Tom sort real fraud from “friendly fraud”—and explain why the first call should usually go to the merchant, not the bank. They also look at confusing statement names, recurring subscriptions, the cost merchants absorb when a dispute lands, and why credit cards generally provide s...

VT, DFAW, and AVGE all promise global diversification—but they take different roads to get there. Don and Tom compare cost, holdings, factor tilts, and the extra risk behind higher expected returns, then explain why the “best” one-fund solution depends on how much risk you actually need. Then a listener asks why advisors build portfolios with many funds when one might do. The answer runs through tax-loss harvesting, rebalancing, personalization, and the fine line between thoughtful design an...

From your 20s to your 60s, the priorities change—but the basic job doesn’t. Don and Tom walk through emergency savings, Roth IRAs, 401(k) matches, rebalancing, retirement planning, Social Security, Medicare, and estate planning, decade by decade. Then Mary calls with a smart Roth-conversion puzzle. They weigh whose IRA to convert, how much to move without wasting a low tax bracket, the age-59½ penalty, and why a household’s accounts should be managed as one portfolio—even when the spouses ha...

Rule Four of Financial Fysics says everything eventually rises—not every stock, not every year, but human productivity and global economic output over time. Don and Tom explain why buying the broad market is ownership in thousands of businesses, not a trip to the casino, and why international diversification matters when nobody knows which country will lead the next century. Then Kenneth asks whether a tiny slice of his emergency fund belongs in stocks. The answer is still no: emergencies te...

Can 21 funds deliver useful global diversification—or mostly camouflage overlap, cost, and complexity? Don opens the Friday Q&A by giving one listener a sharper set of questions to take back to an advisor, including what each fund actually contributes and what would be lost by owning fewer. The questions then move from portfolio architecture to retirement reality. A listener learns why RMDs and Roth conversions should not wag the retirement dog, and another faces a sudden $15,000-a-month...

Active fund managers have a new explanation for years of underperformance: index funds have made their old job harder. Don and Tom examine that award-winning excuse, revisit how indexing reshaped the business, and return to the stubborn arithmetic—when active management charges more, matching the market still means losing to it after fees. Listener questions widen the lens. A UK investor wants to move from 60/40 to 50/50 without taking needless currency risk, while a family needs a sensible ...

Listener questions take over the studio as Don and Tom work through a very big pile without sacrificing any more forests than necessary. The quick tour runs from life insurance in retirement to the seductive yield on floating-rate bank-loan ETFs—and why extra income usually comes with extra risk. Then a live call turns asset allocation into an actual retirement plan: how a couple can move from 90/10 to 70/30, use Roth space intelligently, and rebalance without guessing what the market will d...

AI stocks are booming, valuations are stretched, and capital spending is surging. Does that add up to a bubble—or just another story investors cannot reliably time? Tom and Don walk through Fidelity’s warning signs without pretending anyone can ring a bell at the top. The practical conclusion is less exciting and more useful: stay diversified, keep realistic expectations, include the fixed income your plan needs, and do not mistake a recent gain for money the market owes you forever. Then a...

Markets fluctuate. That sounds obvious—until a favorite stock climbs for years and investors start treating gravity as optional. Tom and Don revisit Financial Physics and the essential difference between a temporary market decline and permanent single-company damage. The cure is not predicting the next dip. It is connecting the return you need with the volatility you can tolerate, then owning thousands of companies and rebalancing instead of reacting. Questions range from IRA eligibility fo...

Bonds are supposed to be the brakes in a portfolio—but should those brakes be BND, a shorter-term fund, CDs, or a Treasury ladder? Don explains why duration, yield stability, and personal comfort make the answer more nuanced than one ticker. The Friday questions keep coming: pairing AVGE with VT, moving $5 million from real estate into a retirement portfolio, understanding an emerging-markets fund that became legally non-diversified, and building 529s for grandchildren. The final stretch is...

AI can crunch a portfolio, harvest losses, and explain an investment concept in seconds. But can it stop a nervous investor from selling at exactly the wrong moment—or understand the life behind the spreadsheet? Tom and Don test the robot-advisor promise, even asking ChatGPT to weigh in. The verdict is a useful division of labor: let technology handle repeatable mechanics, while human judgment, fiduciary responsibility, and behavior coaching remain hard to automate. Then the questions get w...

A quarter in the piggy bank has grown into a maze of UTMAs, 529s, custodial Roth IRAs, and the new child investment accounts. Tom and Don sort the options by what the money is actually for—and who keeps control. The 529 emerges as the flexible favorite, especially with its education uses and limited Roth rollover. Then the conversation turns to concentrated factor ETFs, the familiar Bitcoin argument, and whether private markets are really swallowing public investing. The through-line is ref...

Chasing performance feels like the easiest way to make money—but buying what has already gone up often means arriving late and leaving with less. In this episode of Talking Real Money, Tom and Don examine the “behavior gap”: the difference between an investment’s return and what investors actually earn after buying high, selling low, and chasing the latest market story. They explain why disciplined diversification and a sensible asset allocation usually beat a portfolio built around hot ideas...

The episode covers market bubbles, diversification, Social Security timing, and retirMarkets aren’t mysterious—they’re driven by one of the oldest economic principles there is. In this episode of Talking Real Money, Tom and Don explain why supply and demand can send prices soaring in the short run… and why disciplined investors should usually ignore the excitement. You’ll also hear practical answers to listener questions about Social Security timing, investment clubs, umbrella insurance, and ...

This week Don tackles seven excellent listener questions covering everything from credit cards and emerging markets to covered-call ETFs, annuities, retirement buckets, and whether investors should worry about new additions to stock indexes. 00:51 Summer surge in listener questions 01:15 LitReading success and thanks 02:01 Are credit cards really evil? 05:09 Emerging markets inside international funds 07:44 Paying kids for chores to fund Roth IRAs 10:58 Covered-call ETFs (JEPI and others) 15...

What exactly is a model portfolio—and should you trust one with your retirement? Tom and Don explain why professionally designed model portfolios can improve consistency and reduce advisor bias, but also why investors should be wary as firms like Morningstar begin adding private equity, private credit, and other alternative investments to traditional portfolios. 00:12 What is a model portfolio? 02:11 Why advisors should use investment models 03:31 Morningstar’s new private market portfolios 0...

Can keeping up with financial news actually make you a better investor—or just make you more confident about making bad decisions? Don and Tom dig into research on how markets react to news, why investors tend to overreact to splashy stories and underreact to boring numbers, and whether sophisticated traders can actually exploit those inefficiencies. Then, a caller nearing retirement asks how to build a conservative brokerage account to bridge the years before Social Security. Plus, the guys ...

Having a child later in life can change far more than your sleep schedule. It can completely rewrite your retirement plan. Don and Tom explore the financial realities of becoming a parent in your late 40s or 50s, from college savings and life insurance to delayed retirement and the temptation to sacrifice your own financial future for your children. Tom brings some very personal experience to the conversation—and a few stories about being mistaken for his daughter’s grandfather. Then, a liste...

Money Monday has arrived, and Don kicks off a new weekly series based on his book Financial Fysics. The first “law” may surprise you: according to Don, every dollar ever earned comes from just three sources—luck, theft, or work. He and Tom debate where investing belongs, why entrepreneurship remains one of the best paths to wealth, and how much luck really contributes to financial success. Then they answer a listener’s retirement planning question about whether to finance a Florida townhouse ...

Tom’s on vacation, but the listener questions are not. In this packed Q&A episode, Don tackles one of the most common retirement dilemmas: if your Social Security and annuity income already cover your expenses, do you still need a traditional emergency fund? From there, the questions keep coming. Don weighs in on what to do with “lazy money” earning only 3%, whether a MYGA is really a better deal than a CD ladder, how to structure a taxable brokerage account for long-term growth, and wher...

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...

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...

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 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...

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...

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...

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...

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...

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...

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 ...

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...

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...

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...

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...

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...

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 misconc...

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, Fishe...

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 o...

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...

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...

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 stre...

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...

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 ...

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 th...

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 ...

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...

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 a...

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 ...

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, an...

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 Securi...

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 ...

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 em...

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 Appl...