Episodes

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, f...

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 student...

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 than rely...

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 por...

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 th...

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 and ...

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 the sho...

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, and t...

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 Security ...

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 a t...

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 emoti...

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 Apple Podca...

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, contribution limits, and retirement withdrawal rules. The episode then pivots into listener questions about ACAT transfer anxiety during market volatility and a blistering takedown of indexed annuities, including misleading “bonuses,” surrender charges, and the illusion of “market re...

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 precious metals sales. They contrast long-term investing with speculation, discuss Jamie Dimon comments taken wildly out of context, and explain why gold’s recent surge says little about the future. Questions? Comments? Click!

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 discussion traces Fidelity’s evolution from mutual fund pioneer to 401(k) powerhouse, highlighting its adaptability as active stock picking gave way to index investing (driven in part by figures like Jack Bogle). It also examines the firm’s surprising embrace of cryptocurrency under ...

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 by chasing trends, but by developing a personal “craft” and aligning it with real-world need. They connect that concept to investing discipline—ignore noise, focus on what you can control—and emphasize experimentation early in life. The back half pivots to listener question...

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 diversification debate sparked by Markowitz and Bessembinder research. He emphasizes that financial advising is primarily a sales-driven business, warns against overly complex and leveraged investment strategies being pushed by Wall Street, reinforces the importance of broad diver...

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 Mobius—highlights why most investors are dramatically underexposed to this critical asset class. Don and Tom explain that while emerging markets bring higher volatility and currency risk, they also offer diversification, access to faster-growing economies, and exposure you ...

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 serious liquidity risks—all for returns that barely edge out (if at all) simple public market strategies. They argue that the supposed advantages—like the “illiquidity premium” and diversification—don’t hold up under scrutiny. The episode then pivots to smart listener quest...

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 while appearing legitimate. Don and Tom walk through how these schemes work, why they’re often legal but unethical, and how to avoid them with simple habits like ignoring unsolicited messages, using unique passwords, and booking travel directly. A listener question then piv...

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 actual needs. The episode leans hard into practical fixes: delay Social Security when it makes sense, build a real financial roadmap, ignore friends-as-advisors, and understand the difference between savings and portfolio strategy. A listener question adds clarity on when (and wh...

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 tackles ETF vs. mutual fund tax efficiency at Vanguard, pushes back on “fancy” portfolio add-ons like managed futures and long-term bonds, clarifies why employer 401(k) matches are always pre-tax, and gives a pragmatic take on so-called “Trump accounts” (free money… with strin...

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 personal market theories is just automated speculation—no edge, no accountability, and no evidence it works. They contrast this with decades of data showing that even professionals fail to beat simple index investing. The episode also tackles a listener question on Roth conversi...

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, while long-term returns are driven by economic growth and corporate earnings. They reinforce the importance of global diversification, push back hard against market-timing myths (with a great 1929 example), and remind investors that reacting to headlines is a losing game. Li...