Talking Real Money - Investing Talk

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Ep. 1746: Nothing Wins Oct 09, 2025

Show notes

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 allocation funds lose to “do-nothing” portfolios
1:45 What tactical allocation funds really are (a.k.a. expensive market timing)
2:52 Morningstar urges investors to “stay the course”
3:04 Revisiting “Mind the Gap” and why investors underperform their own funds
4:28 Data comparison: $10k in tactical vs. passive portfolio over 10 years
5:31 Why professionals can’t beat buy-and-hold investors
6:51 Human behavior, arrogance, and the illusion of market-timing skill
8:37 The need for a written plan and risk-based portfolio
9:58 If you have a plan, market noise stops mattering
10:22 Tangent: WWII documentaries vs. Taylor Swift’s Miss Americana
11:21 Listener question #1 – Paying off a low-rate mortgage vs. investing
13:35 Math and emotion collide: cheap money, liquidity, and peace of mind
15:35 Listener question #2 – TIAA Wealth Management fees and fiduciary standards
18:31 Reading TIAA’s ADV: possible fees up to 2% on small accounts
20:08 Comparing local RIAs vs. large institutions
21:08 Clarifying blended fees and fund costs
21:47 Listener question #3 – Vanguard advisor suggesting 60/40 allocation
22:53 Risk tolerance vs. risk need – the real balance
24:05 Investment Policy Statements and Vanguard’s advisory limitations
25:46 Call for more listener questions and upcoming Q&A shows
26:15 Don plugs Lit Reading and his new original story “A Chance of Death”
28:24 How AI collaboration shaped the story’s creation
30:59 Discussion of his next story, “Murder of Crows”
32:17 Invitation for audience feedback on Lit Reading stories
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Ep. 1745: Fourth Turning? Oct 08, 2025

Show notes

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 2030? AI job loss, collapsing dollar, wealth taxes
3:38 Don asks: what is this guy selling? Spoiler: $100M wealth club
6:01 $180k to join R360—clearly not for the average listener
6:33 Don’s “financial flinch reflex” PSA spoof (ad)
7:41 Tom: “We love being scared”—AI panic and deepfake video fears
9:07 Caller Sue (68): Ready to retire with $820k and SS? Don says yes
13:05 Sue’s next step: get a fiduciary checkup, maybe run Monte Carlo
14:10 Tom runs one: 50th percentile = she hits zero at 98
15:32 Flexible withdrawal rates might work better than rigid 4%
16:34 Listener voicemail: Should we switch from Roth to Traditional now?
18:16 DT’s Roth vs. traditional strategy: save taxes while you can
20:14 WSJ article on taxes and stock gains—do ETFs instead
21:25 Tax basics for investors: capital gains rates and efficiency
23:26 Mad Men nostalgia and mid-century tax rates
25:15 TV detour: Bewitched vs. I Dream of Jeannie vs. Outlander
27:10 Back to calls: Theodore asks about 403(b) options in Burlington
29:10 Don explodes: garbage annuity vendors dominate the plan
31:01 Aspire is the only halfway-decent vendor… if you avoid their advisors
33:54 Don tells how an Albuquerque teacher got Vanguard into their plan
35:44 Aspire hack: use FundSource for no-load mutual funds
36:14 Caller Steve: hold 20 stocks or sell and rebalance?
37:53 Tom: hybrid approach. Don: depends on need. Watch tax bracket
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Ep. 1744: Another Quarter Done Oct 07, 2025

Show notes

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 quarter-end reflections
1:40 Fears vs. reality: inflation, jobs, and trade wars
2:16 Q3 returns: U.S. stocks +8%, EM +9.6%, silver tops, cocoa flops
3:09 What you had to do to earn those returns: be invested, diversified, and ignore noise
5:13 Don scolds investors still avoiding value and international stocks
6:11 Chocolate aside, it’s been a strong year for stocks and bonds
7:42 Promo: Why guessing isn’t a retirement plan
7:51 Don recovers from a cough; Tom lists worst Q3 performers (lean hogs!)
9:13 Listener Chad argues for claiming Social Security early if you can earn 3%
11:08 Don crunches the math: break-even at age 81–82 if invested at 3%
12:57 Survivor benefits and why waiting helps your spouse
13:57 Don jokes about his wife stealing his life force and living to 112
14:54 Vaccine banter and intro to next caller
15:56 Caller Michael from Burien sells a condo, asks where to put $300k
19:07 Don and Tom suggest municipal bonds like VTEB for tax-free yield
20:20 Michael quotes a great retirement planning aphorism
20:29 Shift to ETF inflows and the downfall of mutual funds
29:13 Vanguard’s tax-free conversion model and Dimensional’s exemptive relief
30:49 What this shift means for investors with taxable accounts
31:17 Mutual funds may soon be the next buggy whips
32:22 Listener Connie asks: do you really get back Social Security withheld when working before FRA?
33:14 Tom and Don clarify: benefit adjusted later, but no “refund”
34:37 Caller Susan from Connecticut: what to do with $250k in cash
36:52 Don: You don’t need more products—you need a real financial plan
39:17 Flat-fee plans and how to find a true fiduciary
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Ep. 1743: Just Questions (and Answers) Oct 06, 2025

Show notes

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: Inheriting farmland — hold or sell?
6:04 Anton from Spokane: Medflation’s impact on Social Security COLA and Medicare premiums
10:45 Jason from Tigard: SPAXX vs. SGOV — which is better for short-term cash?
13:35 Ameriprise client: Should I use an SMA or fire my advisor?
18:41 Luke from Evans, GA: ETF turnover and what it really means
23:25 Tribute to Jonathan Clements — his life, legacy, and impact on index investing
27:10 Personal reflections, audience appreciation, and gratitude from Tom
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Ep. 1742: Copious Questions Oct 03, 2025

Show notes

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-year-old with uncertain job security and $850k retirement + $518k taxable—structuring allocations for early retirement
11:28 Roth vs. taxable brokerage contributions for flexibility before 59½
15:13 Clarifying 59½ rule—date vs. year of eligibility
17:11 Buffered ETFs explained and why they’re just Wall Street gimmicks
21:53 Rule of thumb for first-time homebuyers: mortgage % of income, 15 vs. 30-year terms, and why homes aren’t great investments
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Ep. 1741: A Miracle Plan Oct 02, 2025

Show notes

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 How confident Americans are about retirement security
1:37 “It would take a miracle” vs. “You need a plan”
2:37 The value of professional reviews and planning tools
3:52 No perfect time to retire, recency bias, and government as your “partner”
5:08 Retirement timing compared to parenthood decisions
6:06 The limits of Social Security and lifestyle realities
7:18 Adapting by working longer, delaying Social Security, or reducing expenses
8:25 Cutting wants, working part-time, or considering home equity solutions
9:23 Reverse mortgages and staged retirement strategies
10:03 Purpose, social life, and health in retirement
11:25 Listener question: international ETF with a 30%+ return (AVDV up 38% YTD)
13:02 Why diversification matters for capturing those “30 percenters”
13:22 Listener question: 529 rollovers to Roth IRAs and beneficiary changes
16:21 Listener case study: RN nearing retirement, Facet vs. Northwestern Mutual
18:07 Facet’s flat annual fee structure compared to traditional AUM fees
20:54 The pitfalls of Northwestern Mutual’s high fees and insurance roots
23:34 When to hire a fiduciary and why $1.5M+ means it’s time
25:30 Advisor costs vs. DIY investing, plus an extended “haircut analogy”
27:13 Shout-out to AI-generated Talking Real Money show art
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Ep. 1740: Behavior Prompting Oct 01, 2025

Show notes

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 Squarespace rant: how customer service died
4:13 Vanguard limiting fund lists—bias toward active funds?
6:22 AI is coming for investing advice
6:35 Listener call: $800K household, cheap mortgage, “living life” vs upgrading home
10:22 House affordability rules: 25–30% PITI, low-rate lock-in dilemma
12:19 Call from Jim in Bellevue: QQQI high-yield ETF
13:44 Why covered call income funds are risky, volatile, and gimmicky
17:41 Tech focus, March 2000 parallels, why diversification beats chasing yield
19:29 Covered call strategies—why they lose upside and add complexity
22:50 Listener email from Shauna: which Utah 529 portfolio to pick
24:36 Best choice = age-based glide path, simplicity and cost advantages
26:13 Follow-up caller: Roth IRAs for kids, risk of inflated wages and IRS scrutiny
29:24 Who checks wages? IRS shutdown jokes, K-1 confusions, AI tax analysis fail
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Ep. 1739: Clements' Consistent Counsel Sep 30, 2025

Show notes

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 banter.
1:04 Remembering Jonathan Clements and his influence
2:59 Pearl #1: Make and save money early, passion can wait
3:54 Pearl #2: Winning isn’t everything—avoiding losers matters most
5:05 Pearl #3: The tax code rewards patience and savers
5:50 Pearl #4: Don’t just stand there, do something (in life, not trading)
7:37 Reflection on his loss and the scarcity of sensible money voices
9:34 Critiquing Kiplinger article and annuity sales cloaked as fiduciary advice
11:44 Pearl #5: Humans are built to strive, not sit idle—retirement requires purpose
12:40 Preview of rising early-retirement questions in upcoming Q&A show
13:22 Vacation banter, Disney’s Aulani resort, and “surfing together” joke
14:13 Back to annuity sales, fiduciary mask problem, and misleading disclosures
17:39 Listener email anticipating annuity criticism—prediction fulfilled
18:12 Listener call: pushback on jargon, “basis points vs. bips” debate
20:13 Listener call: bond ETF BINC—why it’s loaded with junk and risky
25:22 Explaining Roth-only 401(k) catch-ups starting 2026 for $145k+ earners
27:22 Listener call: ETF vs. mutual fund conversions, Vanguard’s patent, Fidelity status
31:29 Listener call: couple with $1.6M in cash, wife afraid of investing
35:36 Don and Tom’s advice: show need via a financial plan, start with small stock exposure
35:59 Listener call from Italy: CDs, interest rates, and laddering vs. penalties
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Ep. 1738: ETF Showdown Sep 29, 2025

Show notes

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.
0:04 Middle-dweller banter and show open
0:54 Why ETFs replaced mutual funds as the easy route
1:23 The “big three” global ETFs: VT, AVGE, DFAW
2:34 Which is “better”? Spoiler: none—or all
2:56 Diversification: DFAW 13,700 stocks vs VT’s 10,000
4:00 Expense ratios: Vanguard’s cost advantage
4:32 Risk/return projections and why they’re guesses
6:22 Microcaps explain much of the differences
7:55 Why small/value stocks historically outperform
8:55 Style box breakdown: small vs large allocations
9:45 U.S. vs international exposure: “pandering portfolios”
10:57 Tech vs financials: sector allocations diverge
12:09 Recent performance snapshots, short vs long term
13:34 Index (VT), Factor (DFAW), Rules-based tilt (AVGE)
15:25 Long-term results: Avantis beats Vanguard despite higher fee
16:15 Risk/return symmetry: you could make a lot, lose a lot
16:45 Listener Q&A: $2B Powerball jackpot—lump sum or annuity?
18:01 Publishers Clearinghouse collapse leaves winners unpaid
21:07 Listener Q&A: Ameriprise SMA fees and pitfalls
23:48 Why Ameriprise’s “nice” advisors are still costly
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Ep. 1737: Questions and Critiques Sep 26, 2025

Show notes

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 and critiques Don & Tom’s take
5:55 Don responds, clarifies criticisms, and acknowledges Ramsey’s positive impact
8:00 Portfolio question from Andy: building a 60/40 with a value tilt
11:14 Flat fee vs. AUM advisors—when each makes sense
13:41 Bond question: Fidelity vs. Vanguard total bond funds, and role of international bonds
17:27 Don on thick skin as a talk show host and why critique is welcome
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