Episodes

In this Friday Q&A episode, Don answers a wide range of listener questions, covering everything from market timing behavior and condo pitfalls to portfolio simplification and strategic debt repayment. He offers heartfelt financial guidance with his usual mix of candor and compassion—including a personal confession about his own Social Security decision. Plus, he pleads (just a little) for positive Apple Podcast reviews to combat the crypto bros and insurance hawks. 0:04 Friday Q&A intro and how...

A chaotic day leads Don into a deep (and entertaining) dive into the futility of market timing, spurred by a recent Morningstar article on Pacer’s Trendpilot ETF. Don and Tom break down the mechanics of the fund’s strategy, its underperformance compared to a simple 60/40 portfolio, and the long-term cost of trying to avoid downturns. Listener questions bring up diversification, Roth IRAs, and the eternal struggle with ticker symbols. Plus, a special heads-up for federal employees about an upcomi...

Don and Tom unpack Morningstar’s latest “5 of the Best” investing methods, praising the simplicity of balanced and target-date funds but warning against high-fee versions. They emphasize that no portfolio fits everyone and push for low-cost index solutions. Listeners call in with 401k rollover questions and political discomfort around financial firms—sparking a candid, occasionally funny chat about ethics, emotions, and retirement realities. The episode wraps with a challenge to fix Social Secur...

In this episode of Talking Real Money, Don and Tom reluctantly return to the topic of Bitcoin, using its recent price spike to explore deeper questions about market efficiency, irrational investor behavior, and the legitimacy of crypto as an investment. With nods to Eugene Fama, Cliff Asness, and some well-aimed skepticism, the duo debates whether price reflects value or just hype. Alongside listener calls from California, Canada, and North Carolina, they address portfolio allocation, pension ro...

Don and Tom dive into a new study showing the average investor spends just six minutes researching a stock—most of it just watching the price move. From gut feelings to hometown bias, they unpack why individual stock picking is often driven by emotion, not logic. Along the way, they skewer myths about control, tax efficiency, and the Warren Buffett fantasy. Listener questions cover Roth 401k rollovers, Roth conversion timing, and Fidelity’s commingled active target-date funds—and why none of the...

Don fields a fresh batch of listener questions in this all-audio edition. A longtime fan asks whether a municipal bond ETF (VTEB) is a smarter place than a money market fund for short-term cash—Don explains why liquidity and risk matter more than yield. Another listener wants help navigating how much cash retirees should keep and when to use it—Don breaks it into two simple buckets: one for living, one for emergencies. A third caller gets a red flag for being pitched Cliffwater’s CCLFX fund by a...

Don and Tom roll through Memorial Day weekend with a little heat from the audience, a breakdown of where Americans get their financial advice (hint: it’s not great), and some solid, real-world investing guidance. They take a couple of strong listener calls—one on geopolitical market fear and another from a small business owner unsure how to save for retirement. Plus, Don flaunts a ridiculous cash stash and his new Rodecaster Pro II. Yes, it’s that kind of show. 0:04 Memorial Day weekend caller ...

This episode brings the heat on so-called “financial educators” masquerading as fiduciaries while hawking high-commission indexed annuities. Don and Tom dissect the misleading promises of 9% guaranteed returns, break down real disclosure numbers, and expose the enormous commissions driving these “recommendations.” Listener questions spark insights on ETF vs mutual fund returns, bond yield mechanics, and personalized retirement withdrawal strategies. Oh, and say goodbye to the penny—it’s headed f...

Tom takes a break from vacationing to join Don in a deep dive on target date funds—the good, the mediocre, and the fee-loaded ugly. They break down performance data, highlight major fund differences, and remind listeners why understanding your own risk tolerance still matters. Listener questions spark advice on Roth IRAs for young investors and strategies for holding large tax payments. All with classic banter, bad jokes, and a quick jab at the Raiders. 0:04 Tom’s back (briefly), and the banter...

In this lighter (but still info-packed) Friday Q&A episode, Don tackles a mixed bag of real-world money questions—from Roth conversions and selling the family home to foreign tax credits and the emotional overload of trying to do everythingat once. Listeners wrestle with software vs. strategy, gifting real estate to their kids, and finding financial sanity in mid-life. Don reminds us: good advice doesn’t come with a magic wand, but it does come with a bit of permission to slow down. 0:56 Roth c...

Don shares a deeply personal tale from 2007 when, as an HOA treasurer, he dodged a financial landmine involving auction-rate securities—just before the 2008 crisis froze their liquidity. That real-life scare flows into a fierce takedown of today’s institutional obsession with illiquid assets like private equity, especially in university endowments. Harvard’s high-risk strategies, retirement plans promoting alternatives, and the seductive myths of market outperformance get picked apart. Don and T...

Tom and Don open the show with tech woes and quips before diving into a serious discussion about the U.S. credit rating downgrade and its implications for borrowing costs and long-term debt. They offer practical investing advice in light of the downgrade—think short- and intermediate-term bonds and global diversification. Listener calls bring a colorful array of financial situations: a comfortably retired couple managing rental income, a military retiree with credit card debt, a candid debt hist...

Don returns from a exhausting, comedy-of-errors flight to discuss how the markets pulled an equally wild round trip—plunging, then rebounding to the tune of $8 trillion. He and Tom break down the April stock and bond tantrum, laugh off predictions of recession, and offer practical guidance for scared investors, risk-takers, and those tempted by annuities. Listener questions cover mortgages vs. investing, the role of fixed annuities, and a touching thank-you from a longtime fan who retired well t...

Don and Tom welcome Weston Wellington of Dimensional Funds for a rare and richly insightful conversation covering market volatility, media noise, diversification, and the enduring wisdom of index investing. Weston compares Spam to Motorola, skewers financial hype, and champions simplicity in investing—and yes, he might just sing if you let him. The conversation explores how far the financial industry has evolved (and still has to go), why most investors get in their own way, and whether AI or ju...

Don’s back from NYC with pride (and maybe jet lag), tackling a full slate of thoughtful listener questions. From Roth conversions and the TSP G Fund to cash balance plan gimmicks, RMD timing, overpriced 401(k) plans, and yes, the eternal question: Are annuities ever worth it? Don delivers straight talk, a little outrage, and no-nonsense advice—with some well-placed jabs at the industry’s smoke and mirrors. 0:04 Don returns from NYU graduation trip and thanks listeners for sending questions0:56 ...

Don and Tom launch into a globe-trotting episode—complete with multilingual greetings and a cameo from Cookie Monster—before diving into the serious question of global investing. They challenge the "home country bias" that keeps investors overly concentrated in U.S. stocks, highlight the recent performance gap favoring international small-cap value, and remind listeners that chasing returns and market timing are just two sides of the same bad investing coin. With personal anecdotes, Japan’s long...

In this episode, Don and Tom rewind to the not-so-golden era of Wall Street paperwork, bringing a modern perspective to old-school investing habits. They tackle listener questions around dividend investing, the allure of individual stocks, and whether the 'buy and hold forever' mindset still holds up in the era of ETFs. Along the way, they dismantle outdated advice, give historical context to stock certificate culture, and steer listeners back toward diversified, evidence-based strategies. A lit...

Don and Tom take aim at America's favorite financial myths—starting with the widespread belief that real estate and gold are the best long-term investments. They present nearly 100 years of historical data to show why stocks have far outpaced both. The conversation also tackles misleading annuity pitches, a classic pension lump sum dilemma, and the age-old question facing 20-somethings: save for a house or retirement? Callers bring smart questions about guaranteed annuities, where to park sur...

In this episode, Don and Tom tackle the investor's most persistent foe—fear—especially during volatile markets. They draw on insights from Vanguard and others to reinforce the value of long-term investing, explain why missing a few key days in the market can devastate returns, and stress the importance of rebalancing over reacting. The duo also takes on political distractions, market timing myths, asset location dilemmas, and the emotional turbulence that causes people (including Don’s wife!)...

In this extra-packed Friday Q&A episode, Don powers through a barrage of listener questions while recovering from an attempted heart ablation (yep, he's okay—but not fixed). He dives into everything from sketchy SIMPLE IRA fees and Roth rollover rules, to when it actually makes sense to take Social Security. You’ll also hear a checklist of questions to grill a potential financial advisor with, a primer on small-cap value stocks, and a lightning-round suggestion for international bond exposure. A...

On this Talking Real Money episode, Don and Tom tag-team one of the biggest financial myths around: your house as a retirement plan. With over $35 trillion locked in U.S. home equity, they challenge the idea that owning a home equals wealth. From the emotional pull of mortgage payoffs to the liquidity traps of reverse mortgages and HELOCs, the duo breaks down the risks, rewards, and real returns of homeownership. Then it’s on to listener questions about IRAs, 401(k)s, rollovers, and... fiber (ye...

Tom and Roxy Butner to co-host a packed episode of Talking Real Money, tackling the ever-elusive "magic number" for retirement with a healthy dose of realism, humor, and data. They dig into a Northwestern Mutual study that shows Americans lowering their retirement savings goals—even as confidence continues to slip. Roxy breaks down why retirement planning is all about cash flow, not some mythical lump sum. They field questions on company stock in 401(k)s, bonus check strategies, RMD tax ...

Tom Cock takes the mic solo (with Don recovering from a “procedure”) and brings in advisor Roxy Butner for a special live episode. They reflect on Warren Buffett’s decision to retire in 2025, discussing lessons from his value investing strategy and massive cash holdings. Listener questions roll in on topics like compound interest assumptions, the risks of holding company stock, ETF mechanics, and how best to diversify for retirement. They also recommend the YouTube documentary Tune Out the Noise...

Don and Tom get real about the most important lessons every young person should learn about money—before life (and bad decisions) get in the way. From money values to compound interest, tax realities to the unpredictability of markets, they each offer a list of financial truths no teen should graduate without. Along the way, they drop stories from their own lives, take questions from listeners, and somehow end up discussing soccer (and why Don still doesn’t get it). 0:04 Back to basics: What yo...