Talking Real Money - Investing Talk

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Ep. 1756: Questions Abound Oct 24, 2025

Show notes

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)
2:39 Don suggests simplifying to AVGE, but warns of risk and emotional resilience
4:12 Jesse from Seattle on CPAG “tax-efficient” bond ETF — Don calls it a gimmick
5:55 Don’s math: CPAG only helps slightly at 35% tax bracket, not worth complexity
9:06 Listener compares 403(b) vs. home value growth — Don confirms results typical
12:45 Real estate’s weak real return over time and lifestyle vs. investment value
12:45 California HSA confusion — Don explains CA taxes HSAs like normal accounts
15:22 Nathan from Georgia: Vanguard vs. Avantis funds, and “copy politician trades”
17:20 Don: Avantis adds small/value tilt, AVGE can simplify portfolio management
19:14 Don: “copy-trade” apps are expensive, delayed, and silly gimmicks
20:58 James from Virginia: Vanguard Cash Plus vs. money market funds
22:34 Don explains FDIC difference and risk-reward tradeoff, prefers money market
24:11 Closing reflections, legacy talk, and plug for New Tales Told
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Ep. 1755: Now or Later? Oct 23, 2025

Show notes

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 before full retirement age; Wall Street Journal’s clickbait headline
3:02 The “bird in hand” fallacy and instant-gratification bias
3:48 Don’s confession: took Social Security at 69—and dogs ruined the travel plans
4:40 WSJ’s faulty 5%-return argument and why most investors won’t achieve it
5:43 The math: waiting pays more monthly, but longevity is the unknown
6:32 Trade-offs between retiring early, portfolio drawdowns, and spousal benefits
7:35 NYT’s claim that Social Security is America’s most valuable “asset”
8:08 Don’s rebuttal: it’s income, not an asset—you can’t liquidate it
9:49 Why people misclassify Social Security and how bonds fit differently
10:08 When and how to get a second (fiduciary) opinion on claiming strategies
11:00 The plague of commission-driven “advisors” and fake fiduciaries
12:29 Old brokerage “no-load fund” lies and how similar games persist today
12:40 Listener Q&A: overfunded 529 plan vs. Roth rollover for grad school
14:27 Midwifery degrees, student-loan math, and the 5% rate cutoff
17:13 Rollover IRA question: switching Fidelity funds to Vanguard ETFs
18:15 Active vs. index funds—why fees and diversification matter
20:05 Active-active management and small-cap risk humor
20:54 ESOP question: how much company stock is too much? (Hint: under 5%)
22:42 Selling discipline and diversification in employee-owned firms
24:39 Don and Tom joke about their own ownership and “sell-out” strategy
25:04 Daily calls, good-natured ribbing, and reminders about Saturday’s live show
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Ep. 1754: Surprising Win Oct 22, 2025

Show notes

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 isn’t an asset class but a risky “thingy.”
0:04 Opening banter on the show’s long Seattle run and mission to simplify money.
2:08 The S&P 500 obsession—why investors overweight large U.S. growth stocks.
3:23 Larry Swedroe’s quiz: best-performing asset class 2019–2025 (hint: it’s not U.S. large growth).
4:07 Dimensional International Small Cap Value Fund (DISVX) vs. S&P 500 Growth (VOOG).
5:20 Why diversification and global exposure matter long-term.
6:20 Break: “Financial Flinch Reflex” PSA.
7:42 Diversification means holding assets that sometimes disappoint you.
8:33 Don’s marriage analogy and listener call-in from Baltimore about trusts.
10:15 Estate simplicity, beneficiary designations, and when trusts are unnecessary.
11:55 The danger of “trust mills” and the value of family transparency.
14:40 Community property vs. joint tenancy—Washington’s unique tax advantage.
16:36 Call from Michael: flexible vs. fixed withdrawal rates in retirement.
17:29 Why a 5% flexible withdrawal often beats the classic 4% rule.
20:19 Research roundup: Kitsis, Vanguard, Morningstar confirm flexible success rates.
23:09 Listener from Tennessee asks about capital-gains exclusions.
25:44 Chris from Seattle: using target-date funds to fix a “hodge-podge” portfolio.
27:24 Adding small-cap value (AVUV) to target-date funds for tilt and simplicity.
28:34 Listener from New Hampshire asks which planning software Appella Wealth uses.
30:06 Call from Sam: best small-cap value ETF options (AVUV vs. VBR).
33:21 Risk, volatility, and why small-cap value offers higher expected returns.
35:47 Mark Hulbert on crypto’s crash—bigger than 1929 by percentage.
36:54 Why hype, not utility, drives crypto coverage.
38:36 Final takeaway: investors remain too U.S.-centric; diversify globally.
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Ep. 1753: Crypto's Crazy Oct 21, 2025

Show notes

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 leverage via MicroStrategy’s Bitcoin bet. Through it all, they emphasize fiduciary discipline, skepticism toward hype, and the basic rule: excitement and good investing rarely mix.
0:04 Pretending last Saturday’s show didn’t happen; Tom’s pun about “Pacific” questions.
1:41 Crypto crash carnage—Bitcoin off 16%, Ethereum down 25%, “Trump Coin” collapsing.
2:30 Comparing crypto’s thrill-seeking crowd to sports betting mania.
3:55 Why your financial advisor should not be your gambling coach.
4:48 The leveraged, insider-ish side of crypto speculation.
5:06 The absurdity of 10,000+ coins that serve no purpose but gambling.
7:40 Calling crypto “speculative” and comparing it to a casino roller coaster.
8:10 Binance payout trouble—proof many players don’t know how to run big-money businesses.
10:32 MicroStrategy’s leveraged Bitcoin plunge and the perils of margin.
11:37 The illusion of “value” in digital tokens versus productive assets.
12:55 Historical echo: borrowed money, bubbles, and 1929-style leverage warnings.
15:25 Listener questions segment opens; lighthearted banter about philately and call volume.
17:02 “ChatGPT beats bad advisors” — asset location done right (bonds in IRA, stocks in Roth).
18:30 Why most “advisors” ignore tax planning in favor of commissions.
20:23 Jay Gould, robber barons, and the Wall Street Journal’s bizarre defense of con artists.
22:12 From Nikola to Theranos—lying as business strategy and why “gray areas” hurt investors.
24:53 The moral cost of tolerating fraud disguised as innovation.
26:36 Why trust is the real foundation of capitalism, not creative deception.
27:00 How to protect yourself: fee-only fiduciary advice and due diligence.
27:36 Mariners hangover theory for low call volume; nostalgic TV banter (“Bewitched”).
29:06 Caller Tom (Seattle): $4 M portfolio, $1 M in money market—how much liquidity is too much?
30:34 The hidden risk of waiting too long to react when rates fall.
33:08 Building a CD ladder to lock yield without betting on one-day rates.
34:25 Quick take: Why they’d avoid owning Boeing stock individually.
36:18 Caller Justin (Florida): emerging-market allocation for high-risk investors.
37:29 Case for small-cap and value tilts, including emerging markets.
38:34 Should you exclude China? Why it’s still essential in global portfolios.
39:29 Closing reminders—use the website for questions, and find fiduciary help at TalkingRealMoney.com.
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Ep. 1752: Protect Yourself Oct 20, 2025

Show notes

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 living alone in a studio
1:09 Market highs and the illusion of perfect timing
2:35 Stock concentration, meme stock mania, and the “Magnificent Seven” dominance
3:34 Listener call: investing in a soccer team partnership promising 15–30% returns
5:12 Why “too good to be true” often is — scams and speculative traps
6:09 Covered-call ETFs (JEPI, GPIQ) explained and debunked
9:39 New private credit ETF (PCR): high fees, low transparency, huge risk
12:49 CNBC hype vs. reality — why turning off financial TV is sound advice
16:21 Listener question: Roth conversions and tax traps in the 30% bracket
19:26 Another listener: funding a new home without derailing retirement
21:47 Don’s rant on overpricing homes — “every house sells at the right price”
23:24 Real estate emotion vs. math — the price always tells the truth
24:31 Episode wrap-up: humor, gratitude, and an absurd “wearable banner” promo idea
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Ep. 1751: Friday Means... Oct 17, 2025

Show notes

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 Roth IRA beyond VTI
5:48 Couple planning early retirement—asset allocation and 72(t) options
9:41 Why bonds exist: emotional stability vs. return chasing
11:29 The case for international diversification
11:29 Long-term HSA strategy and what to do without old receipts
14:32 How to recreate expense records and save PDFs going forward
15:26 Which 529 plans are best for kids aged 2–12? (Utah vs. Schwab)
17:28 Dave Ramsey investing myths and the real purpose of bonds
20:36 When to start adding bonds—take the Talking Real Money risk quiz
21:00 Where to park six-figure cash for car or property purchases
22:46 Short-term safety vs. yield trade-off
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Ep. 1750: Income Sources Oct 16, 2025

Show notes

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 and phone-line reminder
1:41 Why dividend-income portfolios are a trap
2:50 Jason Zweig & Richard Thaler on total-return spending
4:18 Total return beats “high-dividend” illusions
5:39 Robinhood’s option-spread profits and the myth of “free” trading
6:15 Schwab vs. Robinhood: relative honesty in bid-ask spreads
7:43 Thaler’s take on missing retirement plans and automatic savings
9:05 Anniversary talk and the failed “Debbie Show” experiment
10:15 Back to Thaler—why most workers still lack plans
11:39 Tesla options example showing 7 percent spread
12:05 Case for national retirement depository & hybrid Social Security
13:33 Hodgepodge-itis defined (and owned by Don)
14:51 Low call volume and the Mariners’ hangover
15:52 Listener Kevin asks about dividends vs. selling stock
16:53 Reinvesting dividends vs. total-return withdrawals
18:17 Dividends reduce company growth potential
19:45 Why high-yield chasing kills diversification
20:07 Caller David, age 67, plans retirement & asks how to prep
21:55 Social Security timing advice—benefits rise monthly
22:50 David’s details: city pension, deferred comp, house, no debt
24:07 Getting professional fiduciary advice before retiring
25:23 David’s crypto confession and $3K Ripple gamble
27:27 Jail-bound investor asks where to park money
30:18 Don & Tom debate investing from behind bars (humor intact)
33:19 Columbus Day scheduling confusion & closing banter
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Ep. 1749: Many Have Millions Oct 15, 2025

Show notes

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 structure, Empower vs. Vanguard advisor options, and evaluating advisor fees and fund costs. The show closes with their classic blend of education, sarcasm, and fiduciary realism.
0:04 Opening banter, phone number, Florida “cold front,” and baseball chatter
2:33 Topic intro: What a million dollars means now vs. 1890
3:58 Comparing historic vs. modern millionaires and net worth equivalency
4:43 The illusion of wealth—why 70% of assets are often inaccessible
5:30 Planning for liquidity: why paying off a mortgage too early can backfire
6:37 Don’s retirement planning promo
7:39 Historical comparison: 1890s Gilded Age vs. today’s millionaire stats
8:19 Market globalization and modern wealth concentration
9:43 Rare earths and the U.S.–China tariff skirmish
10:22 Market check: stocks, bonds, and gold all dip; volatility talk
12:04 Don’s “unnamed thing” (Bitcoin) drops 10.5%; discussion on risk and rebalancing
13:48 Don shifts to 60/40 allocation—explains rationale near retirement
14:34 Brett Arends’ “Dumbest Stock Market in History” critique discussed
16:00 Debate: Are index investors stabilizing markets through consistency?
17:19 Potato chip tangent and investor psychology
18:32 Arends’ bearishness vs. evidence-based investing
20:00 Protecting your psyche, not every dollar, from market declines
20:20 Podcasting history—when Talking Real Money began
21:32 Caller Samir (Virginia): $4M net worth, suffering from “hodgepodge-itis”
24:15 Don and Tom’s prescription: stop investing until you have a plan
25:42 Margin loan temptation and why 10.5% interest kills the idea
27:00 Tom reinforces the need for a fiduciary planner
27:32 Caller Chris (Texas): moving from Empower to Vanguard PAS
29:21 Vanguard vs. Empower: conflicts, fund choices, and planning gaps
31:46 “Half-pregnant” advice models and Bogle’s legacy examined
34:20 Broader critique: single-provider risk and investor behavior
35:54 Caller Dave (Olympia): evaluating returns, fees, and portfolio costs
37:50 What’s a reasonable expense ratio and advisor fee range
39:24 Final takeaway: judge portfolios by structure, not short-term returns
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Ep. 1748: Retiring Friends Oct 14, 2025

Show notes

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, but maybe too perfectionist
3:25 Monica’s obsessive planning vs. Chandler’s possible risk aversion
4:22 Overthinking portfolios and the emotional toll of too much tweaking
5:01 Savers who struggle to spend: how Monica might hoard instead of enjoy
5:56 Chandler’s likely financial behavior and their combined million-plus portfolio
7:03 Ross: neurotic, divorced, and probably pension-supported
7:54 Why pensions are psychologically powerful for retirees
8:35 Ross would need an advisor to keep him calm and invested
9:14 Rachel: spender, low earner, fashion industry job—not retirement ready
10:30 Joey: the actor’s feast-or-famine finances and SAG-AFTRA pension potential
12:22 Real SAG-AFTRA pension expectations: modest but helpful
13:09 Joey’s likely retirement: modest income, limited comfort outside major cities
13:54 Phoebe: quirky, lovable… financially reckless?
14:28 Phoebe’s imaginary downfall: alimony, bad investing, busking in Times Square
15:20 Big picture takeaways: personality, income, and circumstance aren’t destiny—but they shape outcomes
16:48 The Bings win the retirement game… Phoebe’s husband probably doesn’t stay married
17:30 Listener Q1: Combining fixed and flexible withdrawal strategies
18:52 30-year portfolio simulation using 60/40 and AI tools
20:24 Hybrid strategy results: high survival rate, smoother ride, and growing payouts
21:21 Comparison of 4% vs. 5% withdrawal income over time
22:36 Listener Q2: Replacing expensive international funds in a union 401k plan
24:00 Replace EuroPacific and Developed with Fidelity’s low-cost international index fund
25:17 Expense ratio showdown: PigWX vs. FSPSX
26:32 Closing chaos: how to contact Tom and the long-lost newsletter phone number
27:49 Origins of 800-FUND-004 and how someone just walked into the Bellevue office
29:42 End credits and final laughs—yes, even Tom held back the dad jokes (mostly)
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Ep. 1747: Friday, Again? Oct 10, 2025

Show notes

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 Secure Act 2.0. Expect smart insights, a little snark, and the kind of blunt honesty that’s rare in financial media.
0:04 Listener Q&A returns with an extra dose—six questions this time
1:07 Confusing podcast scheduling clarified (sort of)
2:11 Crypto as an asset class? Don calls it “entirely invented” and dismantles the use case hype
4:32 If civilization collapses, your Bitcoin won’t save you
6:06 Crypto = greater fool theory; Don braces for hate mail
7:30 Dimensional/Avantis vs. index funds—do the extra fees pay off?
9:13 A 15-year comparison: Dimensional Global Equity vs. VT
11:43 Should a pension count as fixed income? Don says no—it’s a volatility game, not income
15:48 CITs (Collective Investment Trusts) in 401(k)s—cheaper, but less transparent
18:58 Index funds should be your benchmark; Don suspects this one’s active
20:02 Claiming Social Security early to preserve Roth? Don says the math rarely supports it
23:59 Secure 2.0 and RMD confusion—born in 1959? You still take RMDs at 73, not 75
26:15 Tech keeps improving—Don urges retirees to stay sharp, stay curious
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