Talking Real Money - Investing Talk

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Ep. 1766: Another Q Show Nov 07, 2025

Show notes

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 exposure inside global funds if geopolitical tensions escalated into war.
0:04 Friday Q&A intro and request for more listener questions
1:33 Bitcoin Bob returns: what “currency debasement” means
4:34 Bitcoin vs. the dollar: volatility and why stability matters
6:59 The real hedge: productive global assets over speculative tokens
8:29 Target-date funds vs. a three-fund portfolio in retirement
10:32 Asset allocation control vs. glide path defaults
11:20 Early retirement scenario: withdrawal sequencing, 72(t), and risk tolerance
14:55 When to add bonds and why emotional behavior matters
16:00 Don’s and Tom’s current equity/bond allocations
17:07 If the U.S. and China went to war: what happens to VT’s China exposure?
20:26 Why global diversification limits catastrophic loss
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Ep. 1765: Leverage Dangers Nov 06, 2025

Show notes

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
3:26 MicroStrategy example: stock up ~30%, 2x ETF down ~65%
5:03 How volatility decay quietly destroys leveraged returns
7:36 5x ETFs and the “go to zero in one day” problem
9:01 When leverage stops being “investing” and starts being gambling
11:38 Listener question: Should retirees hold a bigger cash buffer to avoid selling in downturns?
14:37 Listener question: Should a $4M managed client negotiate fees? (Yes.)
17:43 IRTR vs AOM comparison for someone three years from retirement
22:54 Seasonal weather rant and hunkering down for productivity
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Ep. 1764: Most Investors Fail Nov 05, 2025

Show notes

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 sentiment, cash levels, and memories of 2000 and 2008
4:31 Peter Lynch on market corrections and investor overconfidence
5:40 The danger of timing the market and trusting stocks too much
6:40 “Financial Flinch Reflex” parody PSA (Appella Wealth ad)
7:41 Listener: diversifying a Vanguard UGMA for grandson’s education
12:14 Listener: TSP rollover, age-based bond allocation, and risk tolerance
14:40 The right asset mix for long-term investors in their 40s
15:48 Listener: selling condo for assisted living — planning for late-life care
18:45 Spending vs. inheritance — why it’s okay to use your own money
20:27 Producer’s question: is SoFi robo-investing safe for beginners?
22:56 Emergency funds vs. long-term investing; debt priorities
26:03 Listener: spouse investing in individual stocks — handling differences
28:32 Listener: total market vs. S&P 500 core fund; AVGE and DFAW explained
30:17 Listener: 8% annuity “crediting rate” myth and why it’s misleading
35:42 Real internal rate of return on annuities and risk comfort
37:12 Listener: following advisor from Ameriprise to a bank — fiduciary warning
39:36 Why commissioned products persist and how fiduciary rules differ
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Ep. 1763: Take More Risk? Nov 04, 2025

Show notes

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? Defining purpose versus chasing returns
1:29 The rise of “TINA investing” — there is no alternative to stocks?
2:30 Bonds as shock absorbers when markets collapse
3:57 Questioning global overweights in new stock research
5:01 The emotional toll of chasing maximum returns
6:12 Bonds’ true role: keeping investors calm and consistent
7:50 Zweig’s conclusion — even he still owns bonds
9:06 Retirement timing risk and the case for diversification
10:29 Caller Jay from Georgia — testing a five-year CD ladder withdrawal plan
12:34 Turning the CD ladder into part of a bond portfolio
13:46 What to do with the ladder during a market downturn
14:47 Caller Jason from Washington — Elon Musk, Bitcoin, and the “Strike/Strive” gimmick
15:49 The math behind high-yield crypto preferreds doesn’t add up
17:18 When hype meets hazard: Ponzi parallels in risky yields
18:57 Why “everyone’s doing it” isn’t a defense for bad strategy
20:04 Why MicroStrategy’s dividend promises defy logic
21:15 Listener question — securities lending in IRAs
23:09 How stock lending actually works (and why it barely pays)
24:18 Why most small investors shouldn’t bother
27:15 Vanguard’s new identity crisis: the push into active management
27:47 The profitability problem of index funds
28:53 Can Vanguard’s active funds really beat their benchmarks?
31:48 Why past performance still fails as a predictor
33:14 Vanguard’s crypto flirtation and industry pandering
35:43 Caller Craig from Seattle — expanding global exposure with AVNV
36:32 The case for adding Avantis International Value ETF
37:46 Early results and long-term expectations
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Ep. 1762: Experts Need Experts Nov 03, 2025

Show notes

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 lighthearted finish touches on long-term care insurance, empty nesting, and the Raiders’ black hole stadium.
0:04 Reintroducing the need for financial help (but not that kind of help)
1:17 Christine Benz’s surprising admission: she has a financial planner
2:27 The value of a “responsible second opinion”
3:25 Why Benz says peace of mind has real value
3:50 Reasons to hire an advisor: second opinions, tax guidance, rebalancing, perspective
4:54 When hourly financial advice makes sense
6:38 Organization and accountability as hidden benefits
8:08 The disinterested spouse problem
8:40 Why succession planning matters more than you think
9:32 “Permission to spend” — an underrated role of advisors
10:19 Who doesn’t need an advisor: young savers and disciplined investors
11:27 When to get a second opinion even if you’re DIY
12:18 Spotting bad advice and hidden annuities
13:03 Who does need an advisor: hodgepodge portfolios and over-50 investors
14:09 Complexity and the need for help beyond 65
14:47 The problem of small investors being preyed upon by salespeople
15:52 Listener question: adding small-cap value exposure
16:47 Comparing AVUV, DFSV, and SLYV performance and structure
19:00 Expense ratios and diversification differences
20:18 Don and Tom’s ETF verdict
21:10 Retirement checkup: 77-year-old with pension and LTC coverage
22:06 Evaluating liquidity, income, and survivorship
23:48 The vanishing quality of long-term care policies
24:56 Tom’s empty-nest plans and aching knee
25:43 Raiders jokes and the black-painted stadium
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Ep. 1761: Halloween Qs Oct 31, 2025

Show notes

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
3:47 When stock lending might make sense for rare or hard-to-borrow shares
4:33 Mortgage payoff debate—2.6% rate vs. 7% investing return
5:30 Don confirms: investing wins, emotion aside
7:09 Caller argues for Berkshire Hathaway B as the “perfect” one-stock portfolio
9:14 Don dismantles the myth—Buffett’s own warnings, risk concentration
11:23 401(k) vs. Roth 401(k)—how to decide and why a plan matters
14:04 Backdoor Roth options for self-employed spouses
15:32 Importance of long-term planning once portfolios near $1 million
15:56 HSA payroll advantage—no Social Security tax on contributions
17:11 Using a Roth to store “extra mortgage” money until retirement
18:08 Why paying off a low-rate mortgage later may not make sense
19:37 Free fiduciary portfolio checkup offer from Apella Wealth
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Ep. 1760: Financial Deja Vu? Oct 30, 2025

Show notes

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 present-day parallels like Bitcoin ETFs and private-market tokens. The takeaway: avoid opaque, speculative products; stick with transparent, low-cost diversification. In the Q&A, they answer listener questions about simplifying global portfolios with VT vs. VTI/VXUS, and about selling or donating concentrated stock positions from employee plans.
0:04 Opening disclaimers and acknowledgment that the episode isn’t meant to scare investors
1:18 Historical parallels—1929, 1987, 2008—and the feeling of “market déjà vu”
2:10 Introducing Andrew Ross Sorkin’s new book 1929 and his NYT column on modern speculation
3:20 Financialization and the loosening of investor protections in the 2020s
4:33 Wall Street’s constant invention of confusing products that favor sellers
4:58 Robinhood’s Vlad Tenev and the illusion of democratizing risk
6:12 Lowering the barriers to private markets and what that means for investors
7:26 Echoes of 1929: leveraged ETFs, margin-like structures, and “Russian-doll” debt
8:29 The perils of leverage and speed of modern market declines
9:02 Private-market tokens and the “mark-to-make-believe” problem
10:25 Overvaluation, lack of liquidity, and Wall Street’s interest in 401(k) assets
11:41 Historical leverage shifts—from banks to private credit
12:58 Why trusting financial “authorities” can be dangerous
13:32 Emotional honesty: people lie, and investors must self-protect
14:42 Jealousy, lottery-thinking, and envy as behavioral pitfalls
15:36 Investing as elimination—avoid what’s complex, costly, or confusing
16:48 Listener Q&A: two-fund simplicity (VT + BND) vs. multi-ETF tinkering
18:38 The temptation to overweight U.S. equities
20:00 Contrarian case for international exposure (VXUS)
21:15 ESPP stock cleanup: when to sell concentrated holdings
22:44 Charitable giving of appreciated stock for tax efficiency
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Ep. 1759: Financial Cockroaches Oct 29, 2025

Show notes

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 close with a fun chat about Halloween chaos and coffee and cocoa prices.
0:04 Opening rant on misbehavior in the financial industry and the perils of “bad advisors.”
1:03 How fired brokers reappear as insurance salesmen—98% stay in the industry.
3:10 Why state insurance oversight is toothless and how low the penalties really are.
5:14 Insurance firms masquerading as planners—why fiduciary-only advisors matter.
6:03 The study’s “cockroach” comparison and why the problem persists.
7:37 How to vet your advisor using FINRA’s BrokerCheck and state insurance lookups.
9:16 State vs. federal regulation—why the insurance lobby spent $200 million to avoid SEC oversight.
11:08 Caller Beth from Washington asks about SR 8201—investing long-term care funds in stocks.
13:27 The fiduciary perspective: diversification and realistic expectations.
15:23 Caller Gene from Puyallup on 529 plans vs. UTMAs for grandkids.
17:55 Tax control, gift rules, and the best state 529 options.
19:20 Holiday gifting and a little banter about who’s on Tom’s “nice list.”
20:22 Halloween costumes, tourists, and Celebration, Florida trick-or-treat madness.
23:28 Behind the scenes: Don reveals the entire “Talking Real Money” production staff (himself).
24:32 Podcast email list plug—how to subscribe at TalkingRealMoney.com.
25:35 Explaining podcasts for the AM radio crowd—how to find Talking Real Money on your phone.
27:30 Listener question from Matthew in Illinois about 457 plan costs and hidden fees.
30:38 The truth about 457s, penalties, and why Schwab’s low-cost ETFs may be smarter.
32:34 Caller Rob from Bellevue discusses attending RetireMeet and noticing the Apella building.
33:18 Wrapping with cocoa and coffee futures—good news for chocolate, bad for espresso lovers.
37:49 Don plugs Litreading’s Scary Story Season before switching to Christmas stories.
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Ep. 1758: Hard to Diversify Oct 28, 2025

Show notes

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 Don’s LitReading “Scary Story Season.”
0:04 Show open — Saturday radio edition and why repetition matters in financial education
1:03 The fashion of diversification — and why it’s “back in style”
2:27 International and small-cap value resurgence
3:15 Why investors chase past returns instead of diversifying
4:02 Gold, inflation, and recency bias — lessons from the 1980s
5:21 U.S. vs. international allocation debate: market cap vs. 50/50
6:20 The long wait for Japan’s market recovery
7:41 Practical diversification tools — AVGE, DFAW, VT
8:19 Stop comparing everything to the S&P 500
9:08 Historical proof: global portfolio vs. S&P since 1931
10:02 Caller Charlie — buying Avantis or DFA ETFs through T. Rowe Price or Vanguard
12:39 How fund custodians differ from managers
13:27 Checking portfolio exposure with Morningstar
14:42 Caller Gabe — invest or pay off debt?
16:45 When to pay off a car loan vs. mortgage
19:35 How to handle multiple mortgages and long-term plans
20:22 Social Security’s 2026 COLA bump and the “good news/bad news” of $102 more a month
22:21 Inflation realities — coffee, beef, and Halloween candy
25:02 Candy talk — shrinkflation and Don’s trick-or-treat haul
25:54 LitReading plug: “Scary Story Season” and Philip K. Dick’s The Hanging Man
27:34 Search “Don McDonald” in Apple Podcasts — chiropractor cameo included
29:05 Listener Victor (a.k.a. George) — can $4 million last 60 years with 5% withdrawals?
31:38 How the flexible withdrawal method works in practice
33:49 Retirement purpose, Monte Carlo results, and FIRE skepticism
37:41 Kindleberger quote on bubbles and envy: “There’s nothing so disturbing as to see a friend get rich.”
38:55 Kindleberger’s background and Manias, Panics, and Crashes
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Ep. 1757: T&R Q&A Oct 27, 2025

Show notes

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 investors
2:21 Diversify, stay tax-efficient, and skip the hype
2:30 Roxy joins for listener Q&A
3:38 Fidelity’s annuity pitch — a listener wonders if it’s time to leave
5:05 Who’s truly fiduciary: Fidelity vs. Vanguard vs. Apella
6:14 Vanguard dipping a toe into crypto
6:51 Quabina from Ohio: $2.2M at 47 — diversified enough to retire at 55?
8:14 Missing global diversification and bonds in an all-U.S. portfolio
9:57 Early-retirement planning challenges and healthcare costs
10:20 How to design the right stock-bond-international mix
11:36 Daniel from California: Are long CDs taxed as capital gains?
13:04 Why CD interest is always ordinary income — and muni bond alternatives
13:29 Year-end planning: RMDs, Roth conversions, and tax optimization
14:45 Common tax mistakes and mis-placed assets
15:19 Emily from Ohio: “Young and Dumb” — a 21-year-old investing the smart way
18:51 Building a first Roth IRA and why bonds don’t belong yet
20:00 One-fund simplicity: AVGE vs. VOO
21:41 Long-term mindset: global diversification and patience pay off
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