Talking Real Money - Investing Talk

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Ep. 1666: Asking Tom and Roxy Jun 13, 2025

Show notes

Tom and Roxy dive into listener questions with sharp advice and sharper metaphors—like why a 1,000-point drop in the Dow is more like a slight temperature dip than a financial catastrophe. They cover smart asset location (where to put what), consolidation tips for retirement accounts, the often-overlooked costs of rental real estate, and the emotional tug-of-war between risk tolerance and capacity as retirement nears. Plus: a gentle roast of Robert Kiyosaki, a Parisian travel tip, and a few digs at over-diversified portfolios.
0:05 Tom’s intro rant: fear headlines and market timing
1:39 Denominator blindness: why scary drops sound worse than they are
2:52 2.4% drop = sweater weather, not financial panic
3:55 Listener Q1 (Jeff): Where to hold stocks vs. bonds—taxable vs. IRA
4:17 Asset location strategy: not just S&P and short-term bonds
5:35 Duration, muni bonds, and why not all income is equal
6:24 One custodian, fewer accounts: simplify to win
7:41 Start with overall allocation, not tax location
9:16 Managing drawdowns, RMDs, and legacy with tax planning
10:54 Listener Q2 (Jason): Should I just let my equities grow?
11:40 Risk capacity vs. risk tolerance: don’t drive 90 if 65 gets you there
13:08 Why 90/10 in retirement rarely makes sense
14:27 Distributions and downturns: another case for bonds
15:28 Listener Q3 (Justin): Real estate vs. market income
16:22 Landlord reality check: equity ≠ cash flow
17:47 The tax myths of rental income vs. investments
19:40 How investors really generate income (total return strategy)
21:01 Time to develop a real estate exit plan?
21:38 Final thoughts, free reviews, and Roxy’s Parisian wisdom
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Ep. 1665: Retirement Disorder Jun 12, 2025

Show notes

This episode explores the psychological and financial side of retirement planning through the lens of entropy. Don and Tom dive into an article from Kiplinger that cleverly compares retirement to the second law of thermodynamics: left unmanaged, both money and purpose tend toward chaos. Only 4% of retirees say they're "living the dream"—and the duo explores why that number is so shockingly low. From maintaining routine and finding meaning to avoiding common money traps like over- or under-spending, this episode is packed with practical insights and sardonic banter. Plus, listener questions on Roth conversions for low-income parents and generating sustainable income in retirement portfolios.
0:04 Why we're talking thermodynamics on a money show1:40 The "Second Law" of Retirement: Life drifts toward chaos2:15 Only 4% of retirees say they're "living the dream"3:06 Why retirement can be scary—even for us4:44 Do something in retirement... but get paid for it?6:09 Volunteering vs. purposeful work (and airplane nostalgia)7:03 Retirement spending traps: splurging or hoarding8:09 The danger of financially supporting adult children9:43 Composer John Williams and the myth of retirement11:24 Three keys to a better retirement: social, purpose, activity12:04 Paul Merriman, semi-retirement, and finding meaning13:23 It all still comes down to money—and the freedom it brings14:42 Steve Martin's quote on money and dumb stuff15:30 Listener question: Tax-efficient Roth conversions for elderly parents20:07 Listener question: Income generation with ETFs vs. income funds22:51 Junk bonds, Franklin Income Fund risk, and total return25:48 Strategy tip: Keeping a year of cash to smooth out volatility26:11 Upcoming events and Apollo's July 9th appearance27:37 Free portfolio review offer and purpose in helping others28:51 Tom's boat motor saga and 1-star review nightmares
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Ep. 1664: Misplaced Money Jun 11, 2025

Show notes

Don and Tom dig into America’s $1.7 trillion in forgotten retirement accounts—29 million of them! They walk listeners through how to search for their own missing funds and share their own finds (or lack thereof). They answer questions about where to park $100K in short-term savings, when (or if) to convert to a Roth in your 70s, the pros and cons of ETFs versus mutual funds in taxable accounts, and the murky territory of backdoor Roth timing and the pro-rata rule. A listener also calls in with praise—and a gentle challenge—to donate or support the show, leading to reflections on how to really help Talking Real Money thrive.
0:05 Welcome back—same truth, new week: invest simply, diversify, and stop overthinking
1:24 Financial complexity is mostly unnecessary—simple portfolios work best
2:37 Listeners have lost $1.7 trillion in forgotten 401(k)s—here’s how to find yours
4:34 Don checks the retirement lost & found—comes up empty
6:33 Tom finds $29 from Starbucks—through a different database
7:36 Sites to check: National Registry, Lost & Found DB, MissingMoney.com
9:15 Caller Alan: What should I do with $100K in liquid, short-term funds?
11:30 Don’s “Three Easy Pieces” ladder strategy: savings + 1-year + 2-year CDs
14:13 Alan’s happy—Bread Savings gets a shout-out
15:43 Talking Real Money Friday Q&A is the listener favorite
17:00 Caller Joel: Should I switch my Vanguard mutual funds to ETFs?
19:14 Yes—especially in taxable accounts, for better tax efficiency
20:44 Caller Sue: At 77, is it too late to convert $100K from IRA to Roth?
27:05 Probably not worth it—tax impact likely the same or worse
29:51 Rethinking retirement tax math—it’s not “your” money until it’s taxed
33:19 Don checks reviews—guess who’s back with a grudge?
33:49 Caller Ray: Can I move IRA to 457 to avoid pro-rata on backdoor Roth?
36:40 Caller Jim: Mom’s advisor switched to LPL—should I worry?
38:59 Jim’s suggestion: listeners donate to a favorite charity in TRM’s name
40:04 Victory Capital funds: Don’s not a fan of their approach
42:41 Why broad diversification beats thematic ETFs with 100 holdings
44:12 Wrap-up: Where to listen, how to submit questions, and why reviews matter
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Ep. 1663: Financial IQ Test Jun 11, 2025

Show notes

Don and Tom salute high-schoolers who tackled the National Personal Finance Challenge, then test listeners (and each other) with the same nine-question quiz—covering basics like principal vs. balance, Roth RMD rules, CDs, vesting, inflation risk, callable bonds, and limit orders. Call-in segments dig into real-world money puzzles: whether to sink home-sale proceeds into a new mortgage at today’s 7 % rates, how (and whether) to value a military pension, rolling a TSP, and a head-scratcher about wildly swinging “management” fees inside a Fidelity IRA. A quick detour touches on Don’s upcoming birthday before they wrap with practical takeaways: know your income gap first, keep fees transparent, and remember—it’s “losing money safely” if cash just languishes.
0:04 Why everyone needs a working knowledge of money
1:22 National Personal Finance Challenge shout-out & why only 0.1 % of high-schoolers compete
2:04 Quiz Q1 — defining principal
4:01 Quiz Q2 — Roth vs. traditional IRA RMD rules
5:10 Invitation for listeners to tackle the quiz live on air
7:38 Quiz Q4 — why CDs pay more (funds locked for a term)
8:57 Quiz Q5 — what “vesting” really means
9:59 Quiz Q7 — parking cash in a sock = inflation risk
12:33 Quiz Q8 — callable bonds explained
13:51 Caller Hillary — use equity to pay down a 7 % mortgage or invest instead?
16:33 Liquidity vs. rate trade-off and psychological comfort of a lower payment
18:43 Model-airplane museum banter & show phone line reminder
20:46 Caller Justin — valuing a pension and TSP rollover strategy
23:45 Start with income needs, then size savings; why keeping TSP is fine if it’s your only IRA
28:13 Caller John — Fidelity “management fee” swings; how to pin your advisor down
33:25 Caller Will — cosmic birthday musings & the age of the universe
36:51 Quiz Q9 — limit orders, and Tom flunks Series 7 trivia
40:35 How few teens get real money education & resources to close the gap
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Ep. 1662: Too Many ETFs? Jun 09, 2025

Show notes

Don and Tom explore the evolution, promise, and pitfalls of Exchange-Traded Funds (ETFs). While ETFs have become the dominant investment vehicle, boasting $8 trillion in assets and more than 4,000 choices, the duo cautions against the “novelty trap” that lures investors into trendy, high-cost, low-diversification funds. They advocate sticking with time-tested providers like Vanguard, Schwab, and Avantis, and urge listeners to focus on strategy over hype. The episode also covers listener questions on Facet Wealth’s alternative investments and Roth IRA income limits, ending with a light jab at Portland’s real estate collapse and Don’s growing jet lag.
0:04 Opening banter and the rise of ETFs as mutual fund successors
1:28 ETF history from SPY to the $8 trillion juggernaut
2:21 Why ETFs caught on: low cost, tax efficiency, index focus
3:45 When Wall Street noticed: strategic beta and rule-based funds emerge
4:59 The novelty problem: gimmicky single-stock and crypto ETFs
6:57 How to filter the 4,000 ETFs to a trustworthy handful
7:34 Which fund families to consider—and which to avoid
8:58 Active vs. passive: the murky middle and the “passively active” dilemma
10:01 Conflicts of interest in ETF endorsements and advertising bias
11:19 ETF investing principles: keep it simple, diversified, and strategic
12:09 Why the industry lumps Dimensional and Avantis with active managers
14:09 Brief detour into Austin, Silicon Valley, and Portland real estate
15:22 Final ETF takeaway: old, boring, and proven beats shiny and new
17:01 Listener Q1: Is Facet Wealth’s alternative income strategy a red flag?
22:01 Listener Q2: Roth IRA income limits, backdoor Roths, and best next moves
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Ep. 1661: Q&A: Debt and Condos Jun 06, 2025

Show notes

In this Friday Q&A episode, Don answers a wide range of listener questions, covering everything from market timing behavior and condo pitfalls to portfolio simplification and strategic debt repayment. He offers heartfelt financial guidance with his usual mix of candor and compassion—including a personal confession about his own Social Security decision. Plus, he pleads (just a little) for positive Apple Podcast reviews to combat the crypto bros and insurance hawks.
0:04 Friday Q&A intro and how to submit voice questions
1:40 What do market-timing traders actually do with their cash during volatility?
4:25 Are condos and co-ops really “the devil”? Why Don’s skeptical
9:46 Listener shares Don sparked his investing journey in the ‘90s
11:15 Should a friend drop her advisor for a robo-platform—or go DIY with VT/BND?
17:32 Why Don prefers AVGE over VTI for broader, smarter diversification
18:15 Tiny differences in fees can mean big long-term results
18:58 Active-duty military caller: Should I pay off debt using savings and ditch whole life?
24:08 Listener nearing 70: Should I freeze my Social Security or just enjoy it now?
26:46 Don’s honest confession about his own SS filing decision
27:52 Why good reviews matter (and how to fight the crypto/insurance trolls)
29:43 Call live on Saturdays while Tom vacations… again
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Ep. 1660: Rube Goldberg Investing Jun 05, 2025

Show notes

A chaotic day leads Don into a deep (and entertaining) dive into the futility of market timing, spurred by a recent Morningstar article on Pacer’s Trendpilot ETF. Don and Tom break down the mechanics of the fund’s strategy, its underperformance compared to a simple 60/40 portfolio, and the long-term cost of trying to avoid downturns. Listener questions bring up diversification, Roth IRAs, and the eternal struggle with ticker symbols. Plus, a special heads-up for federal employees about an upcoming webinar. And yes, kilt ventilation is discussed.
0:04 “It never rains but it pours” rant, helicopters, kilts, and chaos
2:02 Welcome and the evolution from market timing believers to skeptics
3:13 Trendpilot ETF’s moving average strategy explained (kind of)
5:45 Morningstar says: strategy failed, underperformed S&P by 5% annually
6:58 97-year 60/40 portfolio beats Trendpilot in return and volatility
8:32 2020 example: Trendpilot missed the 38% rebound—ouch
9:59 Why market timing fails most investors over time
11:05 Loss aversion vs. long-term strategy with fixed income
13:08 Trendpilot’s $3.3B in AUM—but it still doesn’t justify market timing
14:23 Listener mail: VTEB vs VTBE, Series 65 textbook gems, diversification
18:26 How much in a single stock? Almost none
19:10 Roth IRA allocation question—AVUS, DFIV, AVUV, and maybe just AVGE
22:24 One-fund to rule them all: AVGE breaks it down across 15 funds
24:11 Federal employee webinar pitch – June 7 at appellowealth.com
25:39 Wrapping up with call-in info, dreams about forgetting the phone number, and kilts (again)
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Ep. 1659: The Best Not Best? Jun 04, 2025

Show notes

Don and Tom unpack Morningstar’s latest “5 of the Best” investing methods, praising the simplicity of balanced and target-date funds but warning against high-fee versions. They emphasize that no portfolio fits everyone and push for low-cost index solutions. Listeners call in with 401k rollover questions and political discomfort around financial firms—sparking a candid, occasionally funny chat about ethics, emotions, and retirement realities. The episode wraps with a challenge to fix Social Security and a request for more five-star Apple Podcast reviews before Don dies on the mic.
1:07 Morningstar’s ‘5 of the Best’ investing methods reviewed
1:48 Balanced funds and target-date funds: pros and cautions
2:48 Three-fund and custom-fit portfolios discussed
4:08 Critique of Morningstar’s recommended balanced funds
6:19 Expense ratios of target-date funds and better alternatives
7:17 Morningstar’s risky allocation advice near retirement
9:17 Why one-size-fits-all portfolios don’t work
10:14 Caller Sally: Should we move from T. Rowe Price 401k?
12:56 T. Rowe Price vs. Vanguard fee comparison
14:03 How to roll over a 401k into an IRA
17:39 Custom portfolios vs. simplicity and human behavior
21:42 Caller Lynn: Political discomfort with Schwab as custodian
26:26 Keeping an advisor despite ideological concerns
28:38 Raising the retirement age: Denmark vs. U.S.
32:48 Fixing Social Security: remove the wage cap
35:29 Listener reviews, crypto hate, and ETF conspiracy theories
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Ep. 1658: Crypto Markets Efficient? Jun 03, 2025

Show notes

In this episode of Talking Real Money, Don and Tom reluctantly return to the topic of Bitcoin, using its recent price spike to explore deeper questions about market efficiency, irrational investor behavior, and the legitimacy of crypto as an investment. With nods to Eugene Fama, Cliff Asness, and some well-aimed skepticism, the duo debates whether price reflects value or just hype. Alongside listener calls from California, Canada, and North Carolina, they address portfolio allocation, pension rollover strategies, and even debunk gold’s glitter as a bond replacement—punctuated by a truly explosive segment on “FartCoin.” Yes, really.
0:56 Tom and Don reluctantly dive into Bitcoin and crypto’s price spike
1:37 Are crypto markets truly efficient? Academia vs. reality
2:44 Price goes up because price went up? Questioning efficient market theory
4:17 Cliff Asness on how social media distorts collective investment judgment
6:23 Don restates the three ways to make money: work, luck, dishonesty
6:50 Harvard-style debate: Can markets be truly efficient?
8:24 Rational ignorance and emotional investing behavior
9:36 Fama says Bitcoin will go to zero within a decade
10:30 Dogecoin and meme coins: speculative absurdity vs. real purpose
12:06 Investment principles: Diversify, plan, ignore hype
13:51 Tom and Don are ‘contrary indicators’—Bitcoin jokes ensue
14:14 Call: Clinton in CA asks where to put pension payments he doesn’t need yet
16:13 Investment advice for 5-year+ horizon: high yield/cash/bond/stock mix
17:48 Tom’s wife builds a wheelbarrow, financial education “nonprofit” mailer
19:11 Crypto joke segment: FartCoin rises to $3.50… and the bad puns begin
22:02 Call: Jeff from Canada on gold returns vs. bond stability
24:24 Should gold be part of a diversified portfolio? Historical returns debunked
28:39 Gold bar nostalgia vs. investment logic
29:58 TRM T-shirt giveaway and gold vs. bonds as ‘cool’ vs. smart
31:30 Call: Zach in NC—Should he roll old 401(k) into state pension plan?
33:10 Breakdown of NC pension plan fund options and a 90/10 allocation strategy
36:03 Don signs up for a “non-sales” financial education class by an unlicensed guy
37:50 Red flags: financial advisor not registered anywhere, mystery deepens
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Ep. 1657: Only Six Minutes? Jun 02, 2025

Show notes

Don and Tom dive into a new study showing the average investor spends just six minutes researching a stock—most of it just watching the price move. From gut feelings to hometown bias, they unpack why individual stock picking is often driven by emotion, not logic. Along the way, they skewer myths about control, tax efficiency, and the Warren Buffett fantasy. Listener questions cover Roth 401k rollovers, Roth conversion timing, and Fidelity’s commingled active target-date funds—and why none of them beat a good portfolio of low-cost ETFs.
0:04 Stock picking takes 6 minutes, says NYU study
1:09 Why people pick stocks without research
1:56 Risk analysis ignored by most investors
2:57 The illusion of gut instinct investing
4:22 Beating the market is harder than it looks
5:44 The fantasy of picking only “good” stocks
7:10 The control myth and cost of stock picking
8:29 Buffett’s process vs. your fantasy
9:53 The illusion of control and tax myths
10:58 What real diversification means
12:11 You’re wasting time, not just money
13:11 Emotion makes individual stock picking harder
13:59 Familiarity bias in hometown investing
15:21 Listener Q1: Roth 401k rollover planning
16:27 How many ETFs should a multimillion Roth have?
17:59 Get fiduciary help or risk being sold garbage
18:21 Listener Q2: Roth conversion tax trap
20:17 RMDs aren’t the enemy—bad Roth math is
20:29 Listener Q3: Fidelity commingled target-date fund
21:35 Why active target funds fail investors
22:07 Better option: Three low-cost ETFs instead
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