Episodes

It’s surprisingly hard to know what something is really worth until someone actually tries to buy it—and that problem is front and center in private funds. Don and Tom unpack why private equity, private real estate, and other “alternative” investments often look calm and stable on paper, only to suffer brutal price drops once they finally trade in public markets. From a Wall Street Journal example of a private real estate fund losing roughly 40% overnight, to Morningstar’s troubling enthusiasm f...

A Wall Street Journal column argues that younger investors are turning to options, crypto, and betting as a rational response to a “rigged” economic system. Don and Tom aren’t buying it. While acknowledging real headwinds—student debt, housing costs, wage gaps—they dismantle the idea that gambling is an intelligent adaptation. Drawing on history, lived experience, and actual math, they make the case that leverage, speed, and desperation reliably destroy wealth, while patience, diversification, a...

Streaming was supposed to save us money. Instead, it quietly rebuilt cable… with better branding and worse self-control. Don and Tom trace the journey from rabbit-ear TV to today’s subscription sprawl, where “it’s only $14 a month” quietly becomes hundreds per year. They break down why streaming costs have exploded faster than inflation, how duplication and inertia drain wallets, and what actually works to fix it (bundling, pruning, and strategic binge-and-cancel). From there, the show pivots to...

In this holiday Friday Q&A, Don opens with a festive announcement about Season’s Readings—now Apple-featured and temporarily commercial-free—before diving into listener questions on fixed annuities versus CDs, a creative (and complex) 529-to-Roth strategy tied to Georgia tax deductions, simplifying IRA management and RMDs at Schwab or Vanguard, the unavoidable tax traps of old investment clubs structured as partnerships, and the perennial question of how much U.S. large-cap exposure belongs in a...

Market drops are a gift when you’re young and a potential gut-punch when you’re retired, and this episode walks through why that’s true—and what to do about it. Don and Tom break down sequence-of-returns risk in plain English, then explore practical defenses: cash buffers, CD ladders, bucket strategies, flexible withdrawals, partial retirement, and why stocks still belong in retirement portfolios whether you like it or not. Listener questions tackle letting portfolios ride for heirs, value vs. t...

This episode of Talking Real Money takes aim at the latest “easy money” illusion—house flipping—explaining why rising costs, higher interest rates, softer housing demand, and plain old competition have drained much of its appeal. Tom and Don connect flipping’s decline to a familiar pattern of speculative behavior, much like day trading or past real estate manias, and reinforce why there are no reliable shortcuts to wealth. Listener calls drive a wide-ranging discussion on global diversification ...

A classic TRM episode that starts with Tom’s ill-fated attempt to cross a flooded Snoqualmie River (spoiler: no walking on water) and turns into a timely lesson on market returns, diversification, and why comparing your portfolio to headline numbers is usually a mistake. Don and Tom unpack eye-popping 2025 performance across U.S., international, bonds, and small-cap value, warn against recency bias and overpriced active funds, and take several listener calls on Roth conversions, bad custodians, ...

If you’re nearing retirement and uneasy about the math, you’re not alone. Don and Tom tackle the uncomfortable reality that most near-retirees haven’t actually run the numbers—and many won’t like what they see when they do. Drawing on Vanguard data and real-world client experience, they break down three practical ways to shrink a retirement gap: working longer (but not necessarily full-time), thoughtfully tapping home equity, and spending less before and during retirement. 0:06 Opening and the ...

A holiday-flavored Friday Q&A that covers a lot of ground without selling a single candy cane. Don answers listener questions on Medicare vs. Medicare Advantage (and the IRMAA buzzsaw), how to safely reposition an elderly parent’s taxable account, whether to ditch target-date funds for a DIY equity portfolio, how to think about international small-cap ETFs, why teaching kids to pick stocks is a terrible idea, and what to expect when a “free portfolio review” comes from a company whose name liter...

Today’s show turns a national mood ring into a money lesson. Don and Tom walk through a new Wall Street Journal/NORC survey that sorts Americans into four emotional quadrants—comfortable optimists, comfortable pessimists, stressed optimists, and stressed pessimists. Tom takes the quiz live, landing squarely where most Americans do: personally comfortable, broadly pessimistic. The two unpack why sentiment is so gloomy despite solid personal finances, how risk tolerance shifts with market cycles, ...

Don and Tom take a sharp look at Vanguard’s surprising new direction, especially the decision to fold annuities into 401(k) target-date funds through lightly regulated collective trusts. They contrast Vanguard’s historical simplicity with today’s trend toward complexity, comparing costs, structure, and risk across major providers. Listeners call in with questions about Roth conversions, Schwab target-date funds, entering the market after a forced delay, and whether TIPS or buffered ETFs are wort...

In this special seasonal episode, you and Tom resurrect Ha or Duh, tearing through Investopedia readers’ “rules to live by” and dismantling the silliest ones with mock gravitas. Between the dad-joke arms race, a spirited defense of compounding, strong opinions on due diligence, and a surprising detour into crypto-mad zip codes, the show blends real financial guidance with holiday-season chaos. The episode also hits deeper listener questions on rebalancing, Roth vs. pre-tax strategy in high brack...

In this episode, Don and Tom saddle up for a tour through Schwab’s “Good, Bad, and Ugly.” They applaud CEO Rick Wurster’s warning about the growing overlap between gambling and investing, take a hard look at Schwab’s retail-side conflicts and non-fiduciary sales practices, and then recoil at the truly ugly: Schwab’s acquisition of Forge Global and its push to open private-company speculation to everyday investors. From there, they field listener questions about crypto’s pointless search for a pu...

This Friday Q&A episode tackles a wide range of listener questions: whether someone with full pension income still needs bonds, how to fix a cluttered 403(b) invested through Corebridge, what to make of Bill Bengen’s new comments about higher withdrawal rates, how inherited IRAs are taxed over the 10-year rule, and a quick explanation of the difference between “securities” and “equities.” Along the way, Don delivers a vintage KOA radio tag, explains why simplicity beats complexity in retirement ...

This episode digs into the unwelcome December surprise of capital-gains distributions, especially from actively managed mutual funds. Don and Tom break down Morningstar’s latest list of high-distribution offenders, spotlighting the astonishing 83% capital-gains payout from the Royce Midcap Total Return Fund. They compare the tax drag, costs, turnover, and long-term underperformance of these funds against index funds and ETFs, and explain why tax-efficient investing matters far more than most peo...

A fast, funny Thanksgiving-weekend show where you and Tom unpack why a tiny handful of stocks drive the S&P’s returns, revisit forgotten winners like Hormel and McDonald’s, explain why “you can’t pick them in advance,” and tie it all back to building global, diversified portfolios. Listener calls cover early-retirement withdrawals with 72(t), whether AVGV should replace AVGE, a Thanksgiving relative obsessed with dividends, and a listener being pitched a 1.24% Fidelity “wealth management” upsell...

Tom and Don spend this post-Thanksgiving episode dismantling the illusion that big insurance companies—Northwestern Mutual in particular—are “financial advisors” rather than high-pressure sales organizations built on whole-life commissions. Don recounts his own early days as a Dean Witter cold-call cowboy, and the two walk listeners through a damning Guardian investigation revealing recruitment practices, high-pressure quotas, and the wealth-destroying math behind whole life. The phones open to ...

A light Black Friday edition tackles four listener questions covering Vanguard’s Digital Advisor, the timing of Social Security versus IRA withdrawals, whether to swap target-date funds for a VT/BND mix, and the wisdom (or lack thereof) of adding managed-futures ETFs. The show ends with a look at whether international bonds meaningfully improve diversification (answer: barely). The through-line? Keep investing simple, avoid expensive complexity, and stick with risk-appropriate, broadly diversifi...

Don and Tom run through a Wall Street Journal list of “subtle signs it might be time to retire,” reacting to each one with their usual mix of disbelief, personal anecdotes, and gentle ribbing. The episode wanders into tech reluctance, job promotions nobody wants, Sunday dread, obsessive 401(k) checking, volunteering guilt, missing peers, feeling left out of friends’ retirements, boss-related misery, and aging knees. They also answer listener questions about Schwab Intelligent Portfolios and thei...

This episode opens with a warning to younger investors who take TikTok advice over historical perspective, especially around claiming Social Security early. Don and Tom walk through the guaranteed 8%+inflation benefit increase from delaying, why “take it at 62 and invest it” collapses under market reality, and how fear is driving a surge in early claims. They pivot to Bitcoin’s sharp drop and why crypto speculation is driven by greed, not protection, before teasing Don’s upcoming crypto short st...

Don and Tom go deep on a shady “non-profit” financial education group that funnels retirees into high-commission indexed annuities, using a listener tip to unpack the advisor’s fake credentials, mismatched ADV filings, dubious fiduciary claims, and the simple math that reveals where the money really comes from. Along the way, they cover how to investigate advisors yourself, why financial fairy tales persist, and answer listener questions on Avantis gold holdings, private equity’s impact on small...

A lively Friday Q&A episode tackling listener questions about FSAs vs. 401(k) contributions, BND vs. BKAG bond funds, intermediate-term bonds vs. CD ladders, Avantis fund-of-funds fees and structure, and the financial implications of New York City’s newly elected socialist mayor. The show blends practical investing guidance with jokes about annuity-salesperson Halloween costumes and a detour into political fears vs. economic realities. 0:04 Opening, Friday Q&A setup, thanks to Tom’s grandkids ...

You and Tom spend this episode unpacking a surprisingly liberating idea for investors: that average is good enough. Kicking off with your own story about a two-star podcast rating, you two stumble into a bigger truth—most people are chasing a level of portfolio perfection that doesn’t matter. Christine Benz’s Morningstar piece becomes the backbone of the discussion, contrasting “maximizers” (engineers, tinkerers, over-optimizers) with “satisfizers” (simple, diversified, sane). From there you hit...

Don and Tom open with the investor mistakes Christine Benz highlighted in Morningstar: portfolio sprawl, concentration in the same large-cap tech names, clinging to ancient active funds, ignoring reallocations, and failing at both asset allocation and asset location. The show then shifts into calls—first about fears of an “AI crash,” then a heartbreaking case of an 80-year-old widow stuck in an expensive, incoherent Schwab-built portfolio, which Don dismantles live. Later, Roth conversion strate...