Talking Real Money - Investing Talk

Investing isn’t a game, and treating it like one can quietly sabotage your future. This episode dismantles the idea of “trying out” investments or advisors the way Wall Street has trained people to do for decades. Don and Tom argue that real financial advice starts with planning, not products, and that a true fiduciary focuses on taxes, portfolio design, and long-term goals — not beating markets or selling what’s hot. Listener questions tackle portfolio overlap inside a 401(k), when simplicity beats customization, the reality behind so-called “Trump accounts” for children, and how to evaluate companies like Corbridge Financial in teacher ret...

0:04 Remembering the “good old days” of fat commissions

0:33 From $200 trades to zero commissions—what really changed

1:18 Free trading everywhere… so how do brokers make money now?

2:37 Robinhood’s explosive growth and the rise of trading culture

3:15 Trading volume triples in six years—what that signals

4:42 Payment for order flow, cash sweeps, and hidden costs

6:21 Are investors actually getting a deal from free trading?

7:13 Why frequent trading and poor returns go hand in hand

8:21 Dopamine, gambling mechanics, and Robinhood’s design problem

9:47 Day trading: the comebac...

This episode opens with a reality check on streaming delays before diving into the growing divide between investing and gambling, highlighted by Charles Schwab’s refusal to promote crypto, options, and prediction markets while Robinhood leans fully into high-intensity trading. Don and Tom warn that flashy features and frequent trading usually lead to worse outcomes, not better ones. Listener questions cover whether employees can roll a 401(k) during a plan change (usually no), how to cope with bad retirement plans, and how to choose between a high-cost growth fund and a low-cost index option. The show also tackles whether mi...

With Tom on vacation and an eerily convincing AI stand-in holding down the mic, Don kicks off 2026 by tackling one of the most persistent listener questions: how to actually find a true fiduciary—and how to eliminate salespeople fast. Using FINRA’s BrokerCheck as a simple filter, the show explains why the “B” matters, why dual-registered advisors are still a risk, and how complexity is often a red flag. From there, the conversation dives into the rise of RILAs (registered index-linked annuities), why their shiny back-tested returns don’t mean much, and how simpler balanced portfolios often do better with far l...

Wall Street is pitching “fixed-maturity ETFs” as the perfect solution for retirees who want certainty, income, and peace of mind—but are they actually solving a problem that already has simpler answers? In this episode, Don and Tom break down what bonds and CDs really do, why fixed-maturity funds are being pushed so hard right now, and how fees quietly eat away at the promised benefits. Along the way, they explain the real role of bonds in a portfolio, why chasing yield is a trap, and how diversification and simplicity still beat clever packaging. Listener questions tackle fiduciary responsibility in 401...

The calendar flipped, but the rules didn’t. In this New Year Friday Q&A, Don tackles listener questions on longevity annuities (QLACs), legacy insurance mistakes, advice-only advisory services, and the growing trend toward complex fixed-income systems and alternative investments. From insurance math that favors the house to eye-watering fees dressed up as innovation, the message stays consistent: simplicity beats sophistication, fees matter, and global diversification works the same whether you live in Seattle or Spain.

0:00 New year, new Q&A — and why January changes nothing

1:30 QLACs explained and why the math still favors insurers

This episode dismantles the idea that successful investing comes from finding the next hot thing. Instead, Don and Tom argue that good portfolios are built by eliminating what doesn’t belong: actively managed funds, sector ETFs, alternatives, high-yield bonds, gold, and other distractions that add complexity without purpose. Drawing on a Morningstar column by Amy Arnott, they reinforce that most investing mistakes come from chasing performance rather than embracing simplicity and discipline. The show also tackles listener questions on retirement “bucket” strategies, rebalancing timing, Dimensional fund structure, and annuities—emphasizing that bonds exist for stability, cash should be limited and intenti...

As the year crawls to a close, Don and Tom torch the ritual of “New Year, New You” financial advice and take aim at the endless lists of five things you must do next year. They break down why year-end deadlines are mostly psychological theater, why prediction-based investing is a sucker’s game, and how even AI—when pressed—admits the truth: diversification beats cleverness, patience beats prediction, and complexity usually hides higher costs and worse outcomes. Along the way, they tackle 529 plans, proposed “Trump accounts,” Roth strategies for kids and retirees, factor investing myths, and the ongoing media obsession with...

In this post-Christmas edition of Talking Real Money, Don McDonald and Tom Cock dismantle one of the most seductive myths in personal finance: the promise of high returns, no risk, and tax-free income. Using the lawsuit filed by Kyle Busch against Pacific Life as a case study, they expose the dark mechanics of indexed universal life insurance—hidden commissions, opaque costs, fabricated indexes, and returns that quietly disappoint. The episode then pivots to listener questions on diversification mistakes, Roth vs. traditional 401(k)s, late-career pivots into financial advice, ETF selection for retirees, and why doing less with your portfolio al...

A year-end Boxing Day Q&A covering realistic downside expectations for global portfolios, the marginal value of adding international small-cap value, details for RetireMeet 2026, and a deeply skeptical look at Medicaid-compliant annuities. The common thread: diversification helps, simplicity usually wins, and when complexity shows up early, commissions are often lurking nearby.

0:04 Boxing Day confusion, goodwill, and a short-format holiday Q&A

1:07 Why this is a shorter, four-question episode to wrap the year

2:17 How much can a globally diversified stock portfolio really fall

3:06 Limits of global market data and why 2008 still sets expe...

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 for expensive, speculative new ETFs, the episode reinforces a core principle: prices discovered by real markets beat internal e...

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, and boring consistency still work. The system may be flawed, but trying to beat it with casino tactics only helps the house.

0:04 Opening ra...

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 listener questions covering smart investing for an 18-year-old, retirement withdrawal sequencing, trust and estate planning pitfalls, and why complexity is often the real e...

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 diversified equity portfolio. Along the way, Don reinforces core themes: simplicity beats complexity, costs matter, taxes are inevitable, and diversification has no single “correct”...

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. total small-cap funds, tax consequences of rebalancing, and whether political risk should affect public fund investing. The takeaway: there’s no perfe...

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 versus U.S.-only investing, the dangers of concentration risk in the S&P 500, how recency bias distorts performance comparisons, and why owning m...

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, debt forgiveness taxes, and rollover mechanics. The show wraps with Don’s well-earned victory lap for Seasons Readings, now rubbing shoulders with Julie Andr...

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 retirement gap problem

0:52 Podcast platforms, Apple vs Spotify, and Don’s short-story empire

4:08 How TRM rank...

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 literally includes the word annuity. Skeptical, practical, and very on-brand.

0:17 Corny holiday Q&A musical intro...

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, and why feelings often overpower facts. Listener questions follow on retirement diversification, how much risk one really needs if Social Security covers the bills, whether younge...

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 worth owning. Throughout, Don and Tom hammer home the fundamentals: low costs matter, complexity harms investors, active management rarely pays, and your stock/bond mix—not gimmicks...

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 brackets, and the danger of thinking blue chips alone equal diversification.

0:04 Seasonal return of Ha or Duh and setup of Investopedia’s “investing rule...

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 purpose, how to implement a disciplined 5 percent retirement withdrawal strategy, the ins and outs of tax-free Vanguard mutual-fund-to...

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 plans, and walks through why 8% withdrawal fantasies collapse under real-world math.

0:04 Friday Q&A intro and listener call-ins Duration: 00:24:53

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 people realize. Listener questions cover overly complex portfolios, Edward Jones stock positions, odd-lot tender offers, and whether large-cap blue-chip stocks remove the need for bonds. The episode closes with a re...

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.

0:06 Thanksgiving haze, Manhattans, overeating, and setting up the show

2:24 Magnificent 7 vs S&P 493 and how concentrated returns distort hindsight

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 calls about Cambridge’s nearly 3% wrap fees, sociopathic insurance sales relatives, term-insurance needs for young families, Roth vs. pre-tax decisions, and how to find a real fiduciary advisor. The theme is consistent...

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 diversified portfolios—holiday weekend or not.

0:09 Don debates doing a Black Friday episode but decides to keep listeners company

1:58 How to submit questions on the webs...

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 their high cash allocations, discuss the shrinking role of physical cash, explain the real value of pre-1964 silver quarters, and handle calls on Social Security math...

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 story. Listener questions cover bad long-term-care/annuity hybrids, overcomplicated “bucket” strategies, responsible portfolio risk, and finally a breakdown of two expensive hi...

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-cap value, and the quality of Schwab’s 529 plan.

0:04 Don’s industry rant and a look at the “American Financial Education Alliance” disg...

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

0:44 Listener FSA dilemma and choosing between FSA funding or 401k

3:01 Why FSAs are painful and why a 401k wins when choo...

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 Tesla’s trillion-dollar pay package drama, Bito’s goofy “dividends,” SGOV vs. CD ladders, fears about private equity sneaking into retirement plans, and a few classic Don-and-Tom ta...

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 strategy, smishing scams, and a closing riff on Bitcoin’s extreme volatility versus gold. A packed episode on how bad habits, high fees, and fear derail investor...

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 calls round it out — including a thoughtful inheritance question and a late-career investor worried about having “run out of time,” which...

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 portfolio without triggering massive tax bills.

:04 When employers steal 401(k) contributions before depositing them

1:42 The WSJ...

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 international outperformance. Along the way he riffs on talk radio’s decline, teases Tom’s dad jokes, and reinforces the core message: diversify, know your time horizons, and don’t overthink what g...

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 stock cleanup at Schwab, spouse disagreements over individual stock picking, automatic ETF withdrawals at Vanguard, and building Dimensional portfolios inside Aspire plans.

0:04 Don’s rant: “W...

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 Financial-flinch reflex and planning plug

12:21 Listener: starting a 401(k) at 59

15:34 Listener: using taxable funds for a Roth contribution

20:24 Listener: Ro...

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 retirement withdrawal sequencing for a $9M portfolio, evaluating cash balance plans, and deciding between traditional vs. Roth 401(k) contributions. A recurring theme: boring portfolios win.

0:05 Magical thinking a...

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 to spot. Herb offers practical steps on how to avoid getting trapped, plus early holiday shopping advice as tariffs and supply issues...

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 retirement with multi-account withdrawal planning, a discussion of equity/bond allocation in personal portfolios, and what might happen to the small China exposu...

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 gambling is not investing.

0:04 Opening banter and the thrill-seeker pitch for leveraged ETFs

1:29 Leveraged single-stock ETFs explode from zero to $40B<...

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-world financial guidance.

0:04 Universal truths of investing and investor behavior

2:07 Why investors underperform their own funds (Morningstar “Mind the Gap”)

3:30 Market sentim...

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 allocation. The show wraps with a skeptical look at Vanguard’s growing tilt toward active management and new global funds from Avantis.

0:04 Why do you invest? De...

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 complexity). Later, they tackle listener questions about small-cap value ETFs — comparing AVUV, DFSV, and SLYV — and close with a retirement scenario review for a disciplined 77-year-old federal retiree. A lightheart...

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.

0:04 Friday Q&A intro and listener invitation

1:25 Fidelity’s fully paid lending program explained—small returns, limited upside<...

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 Street’s relentless drive to sell complexity to the masses. The conversation moves from cautionary history (leveraged trusts of 1929, margin loans, and subprime mortgages) to pres...

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 State’s ballot measure SR 8201 on investing long-term care funds, answer listener questions about 529 plans versus UTMAs, discuss 457 plan costs and fund choices, and clos...

Don and Tom tackle the timeless topic of diversification — why it’s back in style, why it’s so hard to maintain, and why most investors (and pros) still get it wrong. They walk through how market “leadership” shifts over decades, the global vs. U.S. split, and why comparing your portfolio to the S&P 500 is often a trap. Listener questions cover ETF access at T. Rowe Price and Vanguard, whether to invest or pay down debt, and how the 5% flexible withdrawal rule works in early retirement. Plus, the guys riff on Halloween candy inflation, Social Security COLA bumps, and...

Tom Cock and Apella Wealth advisor Roxy Butner team up for a lively listener Q&A episode covering everything from the new wave of penny-stock IPOs to retirement readiness and tax traps. Tom opens with a warning about the surge in risky penny-stock offerings, then the two dive into listener questions about annuity sales pressure at Fidelity, portfolio diversification mistakes, CD taxation myths, Roth conversions, and one standout 21-year-old listener getting her financial life off to a stellar start.

0:05 Tom opens with a warning about the explosion in penny-stock IPOs

1:26 Why “lottery-ticket” stocks nearly always burn...

Don and Tom tackle another full “Q Day,” answering listener questions on Roth fund selection, bond fund gimmicks, real estate returns, California’s odd HSA tax treatment, switching from Vanguard to Avantis, copying politician trades, and whether Vanguard’s Cash Plus account beats its money market fund. The episode mixes practical investing logic with humor, skepticism, and a bit of Don’s plug for his new storytelling podcast, New Tales Told.

0:04 Q Day begins — Don riffs on “Q” words and high-quality listener audio

1:42 Betsy from Minnesota asks: best funds for a Roth IRA (AVUV, VOO, AVGE)

2:3...

Don and Tom revisit the Social Security debate after new Wall Street Journal and New York Times articles challenge long-standing advice to delay claiming. They dismantle clickbait claims that “waiting doesn’t make sense,” highlighting emotional biases, unrealistic investment assumptions, and spousal benefit considerations. The episode also covers whether Social Security counts as an asset, then shifts to listener questions about 529-to-Roth rollovers for graduate school, switching funds in an IRA, and managing company stock in an ESOP-based 401(k).

0:00 Why they keep returning to Social Security and why 25% of retirees rely on it entirely

1:43 Two-thirds claim...

Don and Tom dive into common misconceptions about what’s really been the top-performing asset class over the past five years—spoiler: it’s not the S&P 500. They compare U.S. large-cap growth with international small-cap value, using Larry Swedroe’s data to highlight the importance of global diversification. Listeners call in about estate planning, withdrawal rates in retirement, and portfolio construction. The hosts explain community property rules, flexible withdrawal strategies backed by research, and which small-cap value ETFs they prefer. The episode closes with a reality check on Bitcoin’s latest crash, revisiting Mark Hulbert’s warning that crypto...

Don and Tom kick off by joking about their “record-breaking” call drought before diving headlong into the week’s biggest speculative loser: crypto. The duo dismantle the mythology around Bitcoin and its countless imitators, comparing the excitement of trading coins to sports betting and reminding listeners that portfolios are for investing, not gambling. They tie the current crypto crash to leverage, insider-like trades, and the same fraud patterns seen in history’s great financial cons—from Jay Gould’s gold-cornering to Elizabeth Holmes’ blood-testing farce. Later, they field listener questions on asset location, liquidity management, emerging-market exposure, and the danger of leve...

Don and Tom tackle a mix of market mania and listener questions, skewering speculative fads like meme stocks, SPACs, private credit ETFs, and covered-call funds. Don opens with a scam text story before the duo dive into the absurdity of “get-rich” products during a record-breaking market. They stress discipline, diversification, and turning off CNBC — repeatedly. Listener questions include Roth conversions in high tax brackets and funding a home purchase without wrecking retirement plans. The show ends on a hilarious tangent about listeners wearing backpack banners to promote Talking Real Money.

0:04 Scam text from Colorado and the hazards of liv...

Don answers six listener questions covering CD ladders vs. bond funds, global diversification for young investors, allocation shifts for early retirees, HSA documentation rules, 529 plan comparisons, and whether Dave Ramsey-style portfolios need bonds. He closes with practical guidance on holding cash for opportunities and a reminder about the value of disciplined, evidence-based investing.

0:10 Friday Q&A intro and how to send in questions

1:51 Are CD ladders a good replacement for bond funds?

3:37 How to build a disciplined CD ladder and avoid rate-timing mistakes

3:41 A father asks how to diversify his daughter’s...

Don swats a studio bug, then swats down the idea of dividend-driven retirement portfolios. Drawing on Jason Zweig’s interview with Richard Thaler, they explain why retirees should focus on total return—spending from a diversified portfolio rather than chasing yield. They hit Robinhood’s profit model, bid-ask spreads, and the need for automatic-enrollment retirement plans. A listener call leads to a discussion of Social Security timing, debt-free retirement, and (yes) hodgepodge-itis—Don’s term for chaotic portfolios. Things wrap with a jailed investor’s question, some gallows humor, and the usual banter about holidays and compliance.

0:04 Bug chaos an...

Don and Tom open with banter about the weather, baseball playoffs, and studio quirks before diving into what it means to be a “millionaire” today versus in 1890. They explore how much of modern net worth is illiquid, why home equity and retirement funds can trap wealth, and how planning for liquidity and income is crucial. The conversation transitions into a discussion of market volatility, rare earth trade tensions with China, and Brett Arends’ critique of index investing. They counter with historical perspective, humor (and potato chips), and advice about risk, rebalancing, and human behavior. Later, listener calls cover portfolio struct...

In this playful and insightful episode, Don and Tom explore how the beloved Friends characters might fare financially if they were retiring today. Using their signature mix of humor and practical investing wisdom, they analyze each character’s fictional career, personality, and spending habits to project their retirement readiness. The second half of the show returns to real-world money matters, answering listener questions about blending withdrawal strategies and fund choices in employer retirement plans.

0:04 Why this episode starts with a Friends reference—and yes, it’s copyright-friendly

0:31 Monica and Chandler Bing as retirement savers: organized, driven...

In this extended Friday Q&A episode, Don answers six listener-submitted questions covering a wide range of personal finance and investing topics. He kicks off with a fiery takedown of cryptocurrency as a viable asset class, arguing it’s based on hype and the greater fool theory. Other questions explore whether pensions should count as fixed income in asset allocation, the performance of Dimensional and Avantis funds versus traditional index funds, the pros and cons of Collective Investment Trusts in 401(k)s, and the strategic timing of Social Security. He ends by clarifying a common misconception about RMDs and Se...

Don and Tom dive into a new Morningstar report showing that tactical allocation funds—those run by “smart” managers who actively shift investments—significantly underperformed simple buy-and-hold index portfolios. They unpack why doing nothing often wins, discuss investor behavior gaps, and revisit the power of staying the course. Listener questions follow on mortgage payoffs, TIAA advisory fees, and adjusting stock/bond splits in retirement. The episode wraps with Don revealing his personal creative project—his short story A Chance of Death on his LitReading podcast—and a teaser for his next story, Murder of Crows.

0:23 Morningstar headline: tactical all

Don and Tom kick off this episode with a satirical bang—mocking the apocalyptic tone of a MarketWatch article about the “Fourth Turning,” a cyclical doom prophecy claiming America faces a cataclysmic reset every 80–100 years. Citing wars, depressions, and now AI, wealth taxes, and the fall of the dollar, the hosts break down the fatalistic tone, expose the fear-marketing behind it, and reassure listeners that, historically, markets have recovered—and rewarded long-term investors.

0:04 Faux alien warning: the Fourth Turning economic apocalypse is coming

1:16 Dissecting the MarketWatch article and the “Fourth Turning” theory

2:26 Peak catastrophe by...

The show kicks off with a sardonic take on turf wars between delivery drivers—yes, really—before diving into third-quarter market returns, investor behavior, and asset class performance. Don and Tom remind listeners (again) that sticking with a diversified portfolio beats timing markets or following headline noise. Listeners call in about Social Security strategies, inheritance accounts for minors, and what to do with large sums of cash in retirement. The show wraps with a smart look at ETF-to-mutual fund conversions and why the old-school fund industry is getting left in the dust.

0:11 Delivery turf wars joke and quar...

A lively, unscripted listener Q&A episode with no set topic — just a flood of great questions. Don and Tom tackle everything from inheriting farmland to the hidden cost of medical inflation, tax-efficient short-term investments, Ameriprise conflicts of interest, fund turnover ratios, and a heartfelt tribute to the late Jonathan Clements, a true pioneer of rational investing journalism. Plenty of wit, warmth, and straight talk about money — plus a personal moment of honesty from Tom about life, loss, and gratitude.

0:04 Cold open: “A show with no topics” banter and weather humor

2:07 Angie from St. Paul: Inheriti...

In the longest Q&A episode yet, Don answers seven listener questions covering everything from concentrated stock windfalls and early retirement asset allocation to Roth vs. taxable contributions, the real 59½ withdrawal date, the dangers of buffered ETFs, and the reality of home affordability. He stresses the importance of security over speculation, the need for actual retirement planning, and the pitfalls of gimmicky Wall Street products, all while weaving in his trademark skepticism and humor.

0:04 Friday Q&A intro and listener surge in questions

2:18 Jackpot in two small-cap stocks at age 70—should he sell?

6:28 42-ye...

Don and Tom tackle Americans’ retirement fears, highlighting a survey where one in five say it would take “a miracle” to retire securely. They stress the importance of planning over wishful thinking, cover the risks of recency bias, taxes, and underestimating longevity, and explain why flexibility—delaying Social Security, working part-time, downsizing, or even using a reverse mortgage—may be essential. Listener questions include a 30%+ ETF return (AVDV), the new rules allowing 529 rollovers to Roth IRAs, and a deep dive into Facet Wealth versus Northwestern Mutual, with a reminder about low-cost index investing and the value of fiduciary advice.

0:04...

Don and Tom tackle the creeping role of AI in financial advice—highlighting Vanguard’s new “nudges” on its platform—before pivoting into lively listener calls. The show explores the balance between saving and living (including an $800K earner debating a bigger house), the risks of high-yield gimmick ETFs like QQQI, the simplicity of age-based 529 plans, and the murky rules around paying kids into Roth IRAs. Humor, skepticism, and practical guidance keep the conversation grounded, with a side of leaf blowers, Italian villas, and Tom’s inevitable puns.

0:10 Don’s dramatic AI apocalypse intro and Vanguard “nudges”

1:20 Squares...

Don and Tom open with a tribute to financial writer Jonathan Clements, reflecting on his career and unique investing wisdom. They unpack five of his “pearls,” including saving early, avoiding big mistakes, and living an active, purposeful life. From there, they pivot into critiques of misleading annuity sales cloaked in fiduciary language, highlight changes coming to retirement account catch-up contributions, and tackle listener questions on bond ETFs, ETF vs. mutual fund conversions, CD strategies, and investing with a reluctant spouse. The show mixes respect for sensible investing voices with sharp criticism of gimmicks, all wrapped in listener calls and bant...

Don and Tom tackle the “big three” global equity ETFs—Vanguard VT, Dimensional DFAW, and Avantis AVGE—breaking down their diversification, costs, risk/return assumptions, style tilts (small/value vs large/growth), and geographic/sector weights. They highlight how DFA and Avantis add microcaps and factor tilts that Vanguard’s index omits, why fees are “pennies” but differences in construction matter, and why “rules-based” is more accurate than “active.” Listener questions cover lottery winnings (lump sum vs annuity), the collapse of Publishers Clearinghouse payouts, and Ameriprise’s pricey SMA accounts. The theme: investing lives in the middle ground—balancing risk, cost, and logic.

In this Friday Q&A edition of Talking Real Money, Don tackles listener questions ranging from the dangers of options trading and critiques of Dave Ramsey, to building a simple 60/40 portfolio, comparing flat-fee versus AUM advisors, and whether international bonds deserve a spot in a portfolio. Along the way, he mixes in humor, candid pushback, and practical advice while emphasizing clarity, simplicity, and the importance of asking good questions.

0:04 Intro, gratitude for enough listener questions to fill a show

1:20 Why Don won’t recommend any book on options trading

3:29 Caller defends Dave Ramsey an...

This episode tackles gold mania in its latest surge, debunking its “safe haven” myth with historical returns and practical comparisons to stocks. Don and Tom expose how Wall Street and fund providers exploit the hype, critique Ameriprise and high-yield muni funds, and answer listener questions on target-date funds vs DIY portfolios, HSA withdrawals, and advisor conflicts. The conversation balances humor, skepticism, and blunt warnings about chasing assets after dramatic run-ups.

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A candid hour on consumer self-defense. We open with iOS 26’s unknown-caller screening and a New York Times crime reporter nearly duped by a “Chase Bank” spoof—lesson: don’t trust caller ID, don’t transact with inbound callers, verify via the number on your card or the bank app, and remember spoofed numbers make simple blocking imperfect. Listeners jump in: a Rule of 55 correction (not 72(t)/72(q)), plus a sharp TSP/Roth asset-location play—keep core market cap in TSP, use Roth for small-value tilt (e.g., AVUV). Then the consumer beat: Florida HVAC sticker shock and why three bids mat...

This episode of Talking Real Money tackles myths about the Federal Reserve and interest rates, explains why mortgage and Treasury rates don’t automatically follow Fed moves, and reminds listeners that markets usually price in expected changes. Don and Tom then pop the cork on wine investing, showing that after costs it performs about as well as plain bonds—and far worse than a 60/40 portfolio. They compare wine and tobacco “sin stocks,” highlight the volatility of individual companies like Constellation Brands and Altria, and use that as a cautionary lesson against stock-picking. Listener calls cover asset location strategies (Roth vs. taxabl...

0:04 Why your home isn’t part of your investment portfolio

0:26 The myth of the American Dream and why owning may not make sense

1:33 A buyer’s remorse story from Atlanta

2:35 $3,000/month to own vs. $1,200/month to rent

3:34 Hidden expenses: $13,000 sewer connection surprise

4:31 “I can’t sell my house” = “I won’t lower the price”

5:35 Housing returns: even hot markets underperform stocks

6:19 Divorcees sharing homes to keep a 2% mortgage

7:35 Why paying off a low-rate mortgage often makes no sense

8:45 Don and Tom both bought home...

Don laments the shortage of voice-submitted questions for the Friday Q&A shows and urges listeners to speak their questions into their phones or computers instead of typing them. He answers four listener questions: whether to take a pension lump sum or annuity, whether to roll a 401(k) into an IRA and how much to keep saving with a union pension, a callout about financial jargon (especially “basis points”), and whether stocks are as speculative as cryptocurrency. Don emphasizes that the annuity option is unusually generous, consolidating accounts can simplify rebalancing, saving as much as possible remains wise, and owni...

This episode explores Americans’ financial well-being in 2025, using a Yahoo Finance/Marist survey as the springboard. Don and Tom discuss how their audience differs from the average American listener, how perceptions of financial health can be misleading, and what to actually do if your finances—or your feelings about them—are getting worse. They debate the usefulness of net worth tracking, stress the importance of financial literacy, and suggest automating savings. Listener questions cover indexed annuities, bond substitutes, tax implications, and long-term care sales pitches. They also read a letter defending Rick Edelman and challenging their dismissal of crypto, which...

Don goes solo this week and covers the wild state of “investing” in 2025 — including single-stock ETFs, leveraged funds, and zero-day options that look more like gambling than investing. He answers listener questions about Roth strategies for kids, aggressive long-term allocations, finding fiduciary advisors, dealing with inherited stock portfolios, and the ethics and fees of big Wall Street firms. Plus, he fields questions about new tax-focused ETFs and whether complicated multi-fund factor strategies are really worth the trouble.

0:04 Don jokes about ChatGPT replacing him, welcomes listeners

1:53 Today’s topic: 30% of new ETFs are tied to single stocks —...

This week Don hosts solo and brings in “Cath GPT” (ChatGPT) as a "live" guest to explore the rise of AI in personal finance. They cover what types of questions AI is best at answering, its limits for real-time data and stock trading, and the importance of privacy and skepticism. Don emphasizes planning before investing, critiques dollar-cost averaging with lump sums, and fields listener calls on shifting from commercial real estate to the market, Roth conversions, AVGE vs. AVUV, resetting cost basis in a low-income year, and avoiding dubious “legacy funds.” The show closes with reminders about planning, asking spoken q...

Don and Tom take listeners on a “mountaintop” look at today’s frothy markets, exploring elevated valuations, retail trading spikes, and record margin debt. They unpack what these numbers really mean, warn against trying to time the market, and reiterate the need for diversification and a long-term plan. Listener questions include a young investor’s Fidelity-heavy portfolio, a 30-something’s aggressive allocation and risk score mismatch, and a listener inquiry about “investwithroots.com,” which Don dissects as a private real-estate fund with fees and risks that outweigh its glossy promises.

0:04 Opening from the market “peak” and climbing metaphor

1:3...

Don answers listener questions on funding a taxable brokerage account, clarifies what “more buyers than sellers” really means, explains why fixed income is about psychology rather than income, gives advice on setting up joint accounts for aging parents, lays out a lifetime HSA allocation strategy, and clears up confusion about Appella Wealth’s connection to Talking Real Money.

0:04 Friday Q&A intro and thanks for listener questions

1:19 When to open a taxable brokerage account (AVGE + SGOV mix)

3:28 “More buyers than sellers” — why it’s really about demand vs. supply

6:23 Whether pension + Social Securit...

Don and Tom dig into international investing — why diversification across borders is essential, why timing international markets is a mistake, and how currency fluctuations affect returns. They revisit Japan’s lost decades, talk emerging markets, discuss John Bogle’s arguments against international investing, and explain why owning all markets all the time makes the most sense. Listener questions cover tax perceptions about California, long-term return comparisons, 401(k) rollover and Rule of 55 withdrawals, and the realities of retiring abroad — including the sticker shock of Guatemala’s healthcare spending.

0:04 Should you invest internationally now that foreign markets are rising?

1:29...

In this episode, Don and Tom dig into the podcast rankings to explain why Talking Real Money isn’t at the top—and why Dave Ramsey still is, despite offering more shame than substance. They explore the concept of financial shaming vs. education, reflect on listener Judy’s brilliant retirement planning, and take aim at stock-trading politicians, especially California Rep. Ro Khanna with his 4,700+ trades in one year. Listener questions cover inheritance allocation, condos as investments, and 401(k) vs. Roth vs. brokerage savings. Bonus: Tom yells at his grandkids, Don hates condos, and Congress gets roasted.

0:04 Who’s #1 in...

Don and Tom break down the overhyped expectations around recent market returns, referencing Jason Zweig’s analysis of 230 years of stock market data. They emphasize that spending and saving habits matter more than chasing 15% returns, and explain why realistic planning using a 3–6% real return assumption over 30-year rolling periods is more prudent. They also tackle questions about RMD strategies from Vanguard IRAs and the TSP’s F and G bond funds. The show ends with a tongue-in-cheek breakdown of NFL team valuations—yes, the Raiders rank surprisingly high.

0:04 Welcome, fatuousness defined, and realistic investing begins

0:52 Why you...

Don and Tom dive into the emotional, financial, and practical realities of supporting adult children. From layoffs to loans, down payments to dog surprises, this episode tackles the growing trend of parents funding their 20- and 30-something offspring—and how to do it without wrecking your retirement. Plus, listener questions about gifting stock, promissory note scams, and why shady annuity sellers keep showing up on the airwaves.

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In this Friday Q&A edition, Don fields listener questions on rolling over a large 401(k) after a layoff, whether IRA money should ever be used to buy real estate, Vanguard’s new active ETF offerings, choosing between Vanguard and Schwab 2035 target-date funds, and whether to treat a foreign apartment purchase as part of an investment portfolio. Along the way, he highlights diversification benefits, cautions against high-cost self-directed IRAs, and emphasizes that homes are assets but not investments.

0:04 Friday intro, royal “we,” and reminder on how to submit questions

1:42 Scott from Louisiana: rolling over a $1M reti...

Don and Tom dismantle the “passive bubble” trope, walk through Morningstar’s active/passive scorecard (great one-year anecdotes vs brutal long-run stats), and recap the steady shift of investor dollars toward indexing. A caller tries to drag the show into politics via data independence (BLS/Fed), prompting a level-headed reminder that markets price reality over rhetoric. The TSP’s revamped I Fund gets kudos for finally adding emerging markets (with a nudge to pair it with value tilts outside TSP). Two meaty segments cover long-term care: costs, weak benefits on traditional policies, when hybrids can make sense, and why many hou...

Don and Tom mark Labor Day weekend with a lively discussion of the so-called September Effect—Wall Street’s superstition about historically negative returns in September. They remind listeners that short-term market timing is a losing strategy and that knowing (not guessing) your risk tolerance and asset allocation matters most. The conversation ranges from Florida’s endless summer and biblical rains to ETF overload, collective investment trusts, tax quirks, and the futility of dodging volatility. Along the way, there’s humor about Costco, fertilizer, wrong numbers, and shameless plugs for Don’s LitReading podcast.

0:04 Labor Day banter, Florida he...

Tom kicks off with a check-in on bond market returns, reminding listeners that bonds are about stability, not yield-chasing. He’s joined by advisor Roxy Butner, who helps answer listener questions about fixed-allocation vs. target-date funds, how much international exposure is enough, Ameriprise “CL” fund share classes with high fees, and whether hybrid long-term care annuity products are worth considering. Together they emphasize cost awareness, simplicity, and aligning investments with real-life needs instead of sales-driven products.

0:04 Intro and bond returns update (BND, DFIGX, SWSBX)

2:30 Why bonds belong in portfolios despite modest returns

2:47 Mailbag intro...

Don fields listener questions from Asheville in this Friday Q&A edition. Topics include calculating investment returns with XIRR versus simple time-weighted methods, rebalancing U.S. vs. international allocations in a Vanguard portfolio, whether children can have multiple custodial accounts (and why 529s may be better), AVGE versus VT and why factor tilts matter long-term, and a skeptical look at Frank Vasquez’s Risk Parity Radio strategy that leans on commodities and “golden ratio” portfolio construction.

1:03 How to calculate investment returns (XIRR vs. time-weighted)

4:19 Portfolio allocation: VTI + VT + BND vs. simpler mix

7:10 Custodial UTMA a...

This episode of Talking Real Money digs into recency bias—our human tendency to expect the future to look like the recent past—and how it’s quietly reshaping retirement portfolios. Don and Tom examine rising stock allocations in 401(k)s and target-date funds, even among older investors, and why this performance-chasing is dangerous. They highlight the risks of target-date fund managers pandering to investors, the importance of rebalancing, and the need to stick to long-term allocation plans based on risk tolerance, not market trends. Listener questions cover immediate annuities, 529-to-Roth transfer rules, and whether paying an advisor’s 1% fee is w...

Tom Cock takes the reins while Don visits family, leading a live call-in show that covers liquidity risks in private investments and university endowments, skepticism over deferred income annuities, housing sale costs, Vanguard ETF gaps, the importance of diversification beyond the S&P 500, and why long-term investing discipline beats reacting to short-term volatility. Callers ask about annuities, real estate commissions, balanced ETFs, 100% stock allocations, and Wellington vs. total market strategies, with Tom stressing global diversification, risk awareness, and building portfolios for real life rather than chasing products or peer pressure.

0:04 Tom hosts solo, Don away visiting his m...

Tom Cock hosts this week’s Talking Real Money solo while Don visits his mom. He reflects on Appella Wealth’s annual client event, where clients talked more about travel, grandkids, and weather than money—showing that the firm’s real value is helping people worry less about markets and more about life. Tom takes listener calls covering whether to renew CDs or move into bond funds, the high costs of closed-end muni funds, portfolio planning with Roth IRAs and target-date funds, estate planning with mutual fund capital gains, and frustrations with annuities. Throughout, Tom stresses planning, simplicity, ignoring noise, a...

Don and Tom revisit their long-standing skepticism of Yieldstreet after CNBC’s investigation reveals major investor losses. They highlight how promises of high returns and low risk almost always end in disaster, connecting this lesson back to their 2022 warnings. The episode underscores the dangers of “magical” investments, the myth of passive income, and why retirement accounts should avoid private assets. Listener questions focus on Roth vs. pre-tax strategy, bracket management, and conversion rules—showing the complexity of tax planning when wealth accumulates.

0:04 Why “too good to be true” investments always fail eventually

1:08 Yieldstreet problems exposed—CNBC investigati...

This question heavy episode of Talking Real Money dives into six listener questions ranging from umbrella insurance and portfolio rebalancing to small-cap value allocation, AI’s role in financial planning, and advisory fees. Don critiques umbrella policies as overpriced peace-of-mind products, gives practical strategies for balancing across multiple accounts, stresses the value of both U.S. and international small-cap value, discusses the disruptive potential of AI in advice (with a cameo from “Kath”), and explains fiduciary fees, taxes, and client experience at a fee-only firm like Appella.

0:04 Big Q&A episode intro and listener reminder about submitting questions...

Why has the stock market been so persistently resilient despite crises like COVID, wars, and inflation? Don and Tom explore whether the current generation of investors is simply too inexperienced to remember real bear markets—and what that means for the future. They reflect on market history, including the 2000–2009 “lost decade,” and warn against overconfidence and overconcentration in U.S. large caps. The episode covers lessons from diversification, the value of bonds, the illusion of wealth during bull markets, and listener questions about rebalancing strategies, tax-efficient withdrawals, and international fund choices. They wrap up with a hilarious movie segment and a pl...

Don and Tom explore why real-life investors consistently underperform the market—thanks to emotional decisions, frequent trading, and flashy sector bets. They break down Morningstar’s “Mind the Gap” study and explain why your behavioral return often lags the market return. Listener questions lead into heated critiques of 403(b) plans packed with annuities, an exploration of the risks of overconcentration in the S&P 500, second-home planning in retirement, and the tax headache of unwinding inherited tech stocks. It’s a fast-paced episode packed with practical advice and sharp jabs at high-fee products and financial marketing nonsense.

0:04 Investor returns vs...

This lively episode of Talking Real Money features trivia-packed investing fun, smart listener questions, and sharp commentary from Don and Tom. They dive into a Wall Street Journal quiz on investing genius, exploring surprising historical returns and market myths. Listener calls span a range of financial planning topics—from special needs trusts and Roth IRAs for kids to emergency fund placement and ETF selection.

0:04 Don and Tom banter about working weekends and boomers in the office

1:55 Wall Street Journal quiz: Are you a stock market genius?

3:20 Which stock created the most wealth in 100 ye...

In this episode, Don and Tom confront the emotionally charged—and often financially tragic—decision to claim Social Security early. They debunk three common justifications: fear of system insolvency, false break-even math, and “I just want my money.” Don shares his own benefit numbers as a real-world example of the value of waiting, especially for married couples. They also address why many can’t wait and explore whether alternatives like balanced portfolios or annuities make sense. Later, they roast misleading “hybrid pension” annuity schemes from KCIS, field smart ETF questions about AVGE and AVNM, and talk target-date funds, including why some belon...

Listener Q&A covering early retirement feasibility, VT vs. SPGM ETF comparison, tax-efficient liquidation of a legacy mutual fund, recommended financial planning resources and Monte Carlo tools, and the pros and cons of laddering target-date funds.

1:36 Can $120K a year work with two pensions and a 7% return?

4:57 VT vs. SPGM — same global reach or hidden differences?

8:58 Selling Grandma’s mutual fund without gifting Uncle Sam

11:44 Best deep-dive planning books and free Monte Carlo tools

15:56 Target-date laddering — smart risk tweak or needless fuss?

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