Talking Real Money - Investing Talk

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 stronger consumer protection than debit cards.

Then it’s listener-question time: a free-dinner annuity pitch promising 12% to 15%, whether to b...

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 and a 20-fund hodgepodge.

Also: the hidden tradeoffs in fractional rental-property platforms such as Arrived, why IRMAA anxiety can ou...

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 have very different tolerances for risk.

Finally: whether retirees still need emergency cash, how much umbr...

Rule Four of Financial Physics 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 tend to arrive when markets are already falling. The guys also look at using qualified charitable distributions fr...

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 skilled-nursing bill that changes the investment plan for good reasons—not because of market timing.

There’s also a...

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 plan for a $200,000 windfall, a near-term car purchase, Roth contributions, and the money left for a brokerage account.

Th...

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 do next. The hosts also weigh simplifying banking at Fidelity or Schwab, the Social Security shortfall, and th...

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 caller pressure-tests the flexible 5% withdrawal idea, followed by questions on delaying Social Secu...

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 for business owners to building a global portfolio in Singapore, choosing bonds near retirement, using a self-directed 401(k) window, and making a...

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 all planning: Roth conversions and IRMAA, choosing a HELOC over a 401(k) loan, and resisting the urge to let th...

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 wonderfully strange: whether a 0.70% advisory fee earns its keep, how a concentrated tech fund hides risk behind a hu...

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 refreshingly simple: match the account to the goal, favor broad diversification, and resist stories that make in...

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.

They also answer listener questions about retirement withdrawal order, Roth conversions, reinsurance funds, high investment costs, a...

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 protecting retirement assets.

00:12 Financial Fysics returns: Rule #2—Supply and Demand
02:04 Tom returns from vacatio...

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)

15:47 Helping a friend avoid an expensive annuity

19:40 Should index investors worry about SpaceX?

21:38 Bucket strategy and...

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
05:20 Liquidity problems with private investments
07:27 The high cost of private equi...

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 compare Avantis global ETFs with Vanguard’s Total World Stock ETF, debate the value of factor tilts, and marvel at how...

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 listener asks about a simple three-fund retirement portfolio, international diversification, small-cap value, Roth asse...

Money Monday has arrived, and Don kicks off a new weekly series based on his book Financial Physics. 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 or withdraw money from a Roth IRA. Along the way they discuss Roth conversion strategy, Florida...

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 where to keep nearly $300,000 set aside for a home purchase in the next t...

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 Joseph in Pennsylvania: should your stock/bond allocation be based on a fixed percentage of your portfolio, or should it be...

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 discussion of the latest Social Security trust fund warning, what it actually means, and the only real ways Congress...

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 reviewing wills, beneficiaries, and backup decision-makers. They also talk about the emotional side of these transitions, including independence, trust, and the da...

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 a likely market downturn and how withdrawals and rebalancing should work once retirement begins. Later, Doug from Utah asks whe...

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: where should investors actually go for trustworthy information, how should listeners think about evaluating a financial advisor, and what really matters when jud...

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 questions.

Later, the guys answer listener questions about whether the small-cap value premium still exists despite the rise of pr...

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 listener questions covering Roth employer matches, Roth IRA withdrawal rules, Roth conversion strategies for retirees, and whether paying taxes now simply to benefit heirs makes financial sense...

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 idea.

00:05 – Why so much money is sitting in cash
03:21 – Americans hold over $20 trillion in cash-like...

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’ve ever wondered whether you’re making your portfolio more complicated than it needs to be, this episode is for you.

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 planning, and why delaying meaningful experiences can be riskier than spending. The episode also answers a listener question about setting up a Roth IRA for a teenager and ex...

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...