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Episodes

Dec. 3, 2025

Hard to Pick

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...

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Dec. 2, 2025

Cold Calls & Commissions

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 ...

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Nov. 28, 2025

Black Friday Q&A

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...

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Nov. 26, 2025

The Right Time to Retire

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...

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Nov. 25, 2025

Value of Wisdom

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...

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Nov. 24, 2025

Nefarious Non-Profit?

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...

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Nov. 21, 2025

Speak Your Qs

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 0:...

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Nov. 20, 2025

Good Enough

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...

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Nov. 19, 2025

Simple Solutions

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...

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Nov. 18, 2025

No Absolutes

You and Tom take on the myth of hard-and-fast financial rules by walking through Real Simple’s list of nine “rules you can break.” From the latte factor to credit cards, budgeting, bulk shopping, and the old “retire at 65” trope, the conversation keeps coming back to a single theme: money isn’t black and white. You push back against absolutists like Dave Ramsey, emphasize discipline over dogma, and highlight the practical realities of saving behavior, debt, lifestyle choices, and risk. Listener ...

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Nov. 17, 2025

Retirement Robbers

A listener’s nightmare 401(k) story sparks a deep dive into how small employers can delay, misuse, or even lose employee retirement contributions before they ever reach the plan custodian. Don and Tom explain the Department of Labor’s weak enforcement, why small plans are most vulnerable, and what workers must do to protect themselves. Then the show tackles backdoor Roth timing rules, Social Security “worst-case” planning, the appeal (or lack of) of mid-cap ETFs, and how to unwind a hodgepodge p...

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Nov. 14, 2025

More Money Q&A

Don fields a full slate of listener questions on everything from SGOV vs. high-yield savings accounts to the differences between AVUV and DFSV, why international stocks belong in a portfolio (but shouldn’t dominate it), and whether equal-weighted funds solve the “Magnificent 7” concentration problem. He digs into target-date and bond-fund suitability for short-term money, clarifies what “rules-based” really means for Avantis and Dimensional, and gently deflates misconceptions about long-term int...

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Nov. 13, 2025

Annuity Reality

Don and Tom question a surprising Wall Street Journal column arguing that annuities should become the default option in 401(k) plans. They explore why the idea is gaining traction, where the logic breaks down, and how the insurance industry benefits when complexity outpaces understanding. Along the way, they dig into the real shortcomings of annuities—fees, opacity, inflation risk, liquidity traps—and why “guarantees” often mask the true cost. Listener questions follow, covering tax-efficient st...

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Nov. 12, 2025

Z Good and Z Bad

Tom and Don grade Gen Z investors from a recent Wall Street Journal article, discussing their portfolios, common mistakes like stock picking, active management, and crypto speculation. They move into practical retirement and college-planning questions from callers — including Roth vs. taxable accounts, 401(k) catch-up contributions, 529 plans, and college costs pushing $90 K a year. 0:04 Gen Z investing habits and media influence 1:59 Grading five young investors from a WSJ profile 7:43 Financia...

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Nov. 11, 2025

Investing Is Dull

Don and Tom tackle investor “magical thinking,” especially the belief that private equity, non-traded REITs, and other illiquid “exclusive” investments offer hidden superior returns. They walk through Jason Zweig’s recent reporting on a Florida pension fund that locked up money, paid higher fees, and earned under 1% a year. The conversation underscores why liquidity, transparency, and diversification matter far more than complexity or exclusivity. The episode also features listener questions on ...

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Nov. 10, 2025

Bring the Card

Tom welcomes consumer advocate Herb Weisbaum (ConsumerMan) to talk through the rising headaches of modern travel and everyday scams. Herb shares a recent Delta Airlines ordeal where he was nearly stranded overseas because he didn’t have the exact credit card used to purchase his ticket months earlier — a policy he and others say is poorly disclosed and inconsistently enforced. The conversation expands to robocall loan scams, fake toll violation texts, and AI-boosted fraud that’s becoming harder ...

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Nov. 7, 2025

Another Q Show

This Friday Q&A tackles a familiar voice: Bitcoin Bob tries again to make the case for crypto as protection against currency debasement. Don breaks down what “debasement” actually means, why inflation gradually reduces purchasing power, and why Bitcoin’s extreme volatility makes it a poor replacement for the U.S. dollar. Productive assets remain the historically reliable hedge. Then: a comparison of target-date funds vs. a DIY three-fund portfolio, guidance for a couple aiming for early retireme...

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Nov. 6, 2025

Leverage Dangers

Don and Tom take listeners on a wild ride through the booming (and frequently disastrous) world of leveraged ETFs. They break down how these funds promise double or triple the excitement but mathematically bleed away returns through volatility decay. A few listener questions follow, covering retirement cash buffers, negotiating advisory fees on large portfolios, and comparing IRTR vs AOM for a near-retiree allocation. Humor, subtle self-mockery, a Jonas Brothers detour, and a reminder that gambl...

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Nov. 5, 2025

Most Investors Fail

Don and Tom tackle the universal truths of investing — namely, that most investors underperform the market due to their own behavior. They discuss the persistence of emotional decision-making, the dangers of market timing, and the importance of diversification and sticking to a plan. Listener calls cover UGMA accounts, bond allocation in IRAs, downsizing for assisted living, robo-investing, annuities, and advisor ethics. The show mixes data-driven insight with classic Real Money humor and real-w...

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Nov. 4, 2025

Take More Risk?

Don and Tom tackle the timeless question: why do you invest? They challenge the “TINA” mindset (“There Is No Alternative”) and dissect new research claiming retirement savers should own no bonds at all. They argue that while stocks outperform over long stretches, bonds remain essential for emotional stability and survival during market crashes. Listeners join in with sharp questions about CD ladder withdrawal strategies, crypto-based dividend schemes, securities lending, and international ETF al...

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Nov. 3, 2025

Experts Need Experts

Don and Tom unpack why even smart, financially literate people sometimes need a financial advisor — prompted by Morningstar’s Christine Benz explaining why she hires one. They explore the value of second opinions, professional organization, tax guidance, spending permission, and succession planning. The conversation also draws lines around who doesn’t need an advisor (DIY investors under 50 with good discipline) versus who does (retirees, disorganized investors, and anyone over 65 facing complex...

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Oct. 31, 2025

Halloween Qs

Don answers a range of listener questions covering topics from Fidelity’s fully paid lending program to the Roth 401(k) decision and mortgage payoff strategies. He explains why stock lending rarely adds much value for ETF investors, why paying off a 2.6 percent mortgage makes little financial sense, and why even Berkshire Hathaway isn’t a substitute for true diversification. Listeners also learn about HSA payroll tax savings and how to build Roth flexibility without triggering the pro-rata rule....

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Oct. 30, 2025

Financial Deja Vu?

Don and Tom open with an honest reflection on market déjà vu—how today’s investing climate echoes the speculative excesses of 1929 and 2008. Citing Andrew Ross Sorkin’s new book 1929: Inside the Greatest Crash in Wall Street History, they discuss the modern “financialization” wave: private equity, venture capital, crypto, and private credit being repackaged for retail investors and even 401(k)s, often under looser regulation. They warn listeners about “mark to make-believe” valuations and Wall S...

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Oct. 29, 2025

Financial Cockroaches

Don and Tom go after one of their favorite targets: bad actors in the financial industry—especially those who flee regulation by becoming insurance salesmen. They break down a shocking new study showing that 98% of brokers kicked out by FINRA stay in the business by selling annuities and other insurance products, often with little oversight. The duo compares this behavior to “cockroaches,” slamming state insurance commissions for weak enforcement and minimal fines. Later, they tackle Washington ...

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