Episodes

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 wond...

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 refres...

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 p...

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) ...

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 com...

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 listen...

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 o...

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 k...

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...

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 discus...

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...

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 ...

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: wh...

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 li...

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 ide...

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...

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,...

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...

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 cust...

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 wh...

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 attenti...