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Episodes

We post new episodes verey weekday (except holidays).
May 15, 2026

May Questions

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....
May 14, 2026

Retirement Relocation Reality

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...
May 13, 2026

Selling Fear

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 especi...
May 12, 2026

Red Hot or Icy Blue?

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 rese...
May 11, 2026

Active Management Myth

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 lo...
May 8, 2026

Another Busy Q&A Day

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 share...
May 7, 2026

Retirement Quiz

Tom takes a Wall Street Journal retirement-account quiz while Don gleefully plays game show host, leading to a surprisingly useful (and occasionally chaotic) discussion of HSAs, Roth IRAs, Trump accounts, 529 plans, contribut...
May 6, 2026

Fear Sells Gold

Don and Tom react to the gold-pushing radio show that replaced Talking Real Money , breaking down misleading claims about gold investing, TSP accounts, and “tax-free” gold IRAs while exposing the fear-based marketing behind p...
May 5, 2026

From Funds to Crypto

This episode features an in-depth conversation with Justin Baer about his book House of Fidelity , exploring how Fidelity Investments helped transform investing from an elite activity into a mainstream necessity. The discussi...
May 4, 2026

Future Proof Jobs?

A graduation-season episode turns into a surprisingly deep conversation about careers in the age of AI, anchored by a New York Times article from Jodi Kantor. Don and Tom explore the idea that successful careers are built not...
May 1, 2026

Friday Querisode

Don flies solo for a Friday Q&A, fielding questions on switching into financial services careers, the risks and reality of “enhanced” direct indexing strategies, whether newer Avantis ETFs add real value, and a classic divers...
April 30, 2026

Emerging Markets Matter

This podcast audio was accidentally posted yesterday, so you might want to listen to our 4/29 episode, if you’ve already heard this one. A listener-inspired revisit of emerging markets investing—sparked by the legacy of Mark ...
April 29, 2026

Smart Money Myths

Private equity gets sold as exclusive, sophisticated, and “what the smart money does,” but the reality is far less compelling. Don and Tom break down the illusion: limited transparency, questionable valuations, high fees, and...
April 28, 2026

Booking Scams

This episode shifts from investing to protection, starting with increasingly sophisticated scams—from fake Microsoft emails to deceptive hotel booking sites highlighted by The New York Times that can triple the cost of a stay...
April 27, 2026

Okay, Boomer

Boomers take the blame (with a grin) while unpacking the real retirement mistakes that still trip people up today—failing to plan, claiming Social Security too early, relying on bad advice, and mismatching portfolios to actua...
April 24, 2026

Flood of Questions

A rapid-fire Friday Q&A dives into one of retirement’s biggest debates—flexible withdrawals versus the traditional 4% rule—with Don explaining why adaptability may be the key to never running out of money. The episode also ta...
April 23, 2026

AI Trading Trap

AI-powered trading is the latest shiny object designed to make investors feel smarter while quietly encouraging more trading (and more profits for platforms). Don and Tom break down why letting an “AI agent” execute your pers...
April 22, 2026

War vs. Markets

War headlines dominate attention, but history shows they rarely have lasting impacts on stock markets. Don and Tom break down why geopolitical events—despite their emotional weight—typically cause only short-term volatility, ...
April 21, 2026

Hard to Save

Roxy Butner joins the show to break down practical retirement saving strategies—especially for entrepreneurs who struggle to pay themselves first. The conversation covers foundational options like IRAs and Roth IRAs, then mov...
April 20, 2026

Why Retire?

Don and Tom tackle the idea that retirement isn’t what it used to be—and maybe shouldn’t be at all. From historical retirement ages (when most people never made it) to today’s longer, healthier lives, they explore why many pe...
April 17, 2026

Qs and Stuff

A wide-ranging Q&A episode tackles the real-world tradeoffs investors actually face: whether Paul Merriman’s aggressive small/value “ultimate” portfolio is worth the complexity and risk, how much stock to put in scary online ...
April 16, 2026

Annuity Tricks

Annuities promise peace of mind—but often at a steep and poorly understood cost. Don and Tom break down when (rarely) annuities might make sense, why most—including fixed indexed annuities and QLACs—tilt heavily in favor of t...
April 15, 2026

Start Young

Starting early beats almost everything else in investing—and this episode drives that home with eye-opening math and a brand-new tool for jumpstarting a kid’s retirement. Don and Tom break down the new “Youth Retirement Accou...
April 14, 2026

On Your Side?

This episode exposes the misleading language behind “best interest” financial sales practices, using the insurance-backed fight against the Department of Labor’s fiduciary rule as the main example. Don and Tom explain why rol...