Talking Real Money - Investing Talk

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Ep. 2011: Four Questions Before Halloween Oct 30, 2026

Show notes

On Halloween Eve, Don takes four listener questions about starting young, retiring early, managing risk, and making the most of Social Security. The costumes may be spooky, but the answers are practical.
First, he weighs whether an 18-year-old without earned income should keep an Acorns account or move to a taxable brokerage account. Then he explains why someone retiring before 59½ may still benefit from pre-tax workplace contributions, with Rule 72(t) and Roth basis providing potential bridges.
Don also looks at how much investment risk makes sense when pensions and Social Security already cover most spending, and why delaying Social Security can be more valuable than reaching for income from a 10-year Treasury—especially for the surviving spouse.
01:00 Halloween Eve and today’s questions
03:58 Investing accounts for young adults
06:24 Taxable brokerage versus tax-deferred savings
09:05 Portfolio risk and when to claim Social Security
13:29 Treasuries versus delaying Social Security

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Ep. 2010: The Market Timing Mirage Oct 29, 2026

Show notes

Market timing always looks easy in hindsight: just miss the 30 worst days. The catch is that the market’s best and worst days cluster together, so getting out means risking the rebound. Don and Tom unpack the seductive math, the impossible two-part prediction, and why diversified buy-and-hold investing remains the boring answer that actually works.
A 73-year-old widow asks what to do after an insurance agent who sold her two EquiTrust annuities calls with another idea. Don and Tom question whether the proposed withdrawals could lead to another commission-paying sale, and examine the conflicts behind the recommendation. They explain why her pension, Social Security, and Vanguard portfolio already cover her needs—and why ending the relationship may be the cleanest move.
They also tackle traditional versus Roth contributions in a municipal 457 plan, including the Roth catch-up rule for higher earners, then examine America’s latest passive-income obsession: laundromats. The conclusion is simple—whether it’s real estate, washing machines, or markets, there is no wealth without work or risk.
01:15 AI jingle and prog-rock memories
03:10 The fantasy of missing the market’s worst days
11:23 Famous market timers and bad forecasts
16:31 Listener questions
17:03 The annuity agent calls again
24:11 Traditional versus Roth 457 contributions
28:34 The laundromat passive-income boom

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Ep. 2009: Finding Your Fiduciary Oct 28, 2026

Show notes

Finding an advisor means looking beyond the word “fiduciary.” Don and Tom explore what it takes to find someone who puts your interests first all the time, why experience and a team matter, and what an ongoing fee should buy beyond portfolio management. They also discuss the challenge of handing over the financial reins—and making sure your spouse has someone to call.
Listener questions tackle adding bonds before a career change, the tax tradeoffs of bonds in a brokerage account, why retirement accounts are not an emergency fund, and how to evaluate Roth conversions when spouses have different retirement timelines.
01:04 Finding a fiduciary who always puts you first
02:08 Why a do-it-yourself investor hired an advisor
05:03 Minimums, experience, and a backup team
07:47 Financial planning beyond the portfolio
09:14 What advisory fees should buy
14:12 Letting go of the financial reins
17:10 Keeping personal biases out of investment decisions
19:44 Adding bonds before a career change
22:47 Bond interest and taxable accounts
26:13 Emergency savings belong outside retirement accounts
29:31 Roth conversions and two retirement timelines
35:17 Disclosures

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Ep. 2008: The Bond Tango Oct 27, 2026

Show notes

Rising interest rates can make bond prices fall—and still be good news for savers. Don and Tom explain the bond-price mechanics, why higher yields matter, and why bonds belong in a portfolio for stability rather than excitement.
They compare BND, money markets, and bond ladders, then explain how rebalancing and holding high-quality bonds to maturity can quiet the noise. Listener questions cover why money markets alone aren't enough and a blunt review of the costly, illiquid Ares Core Infrastructure Fund pitched to an 85-year-old investor.
Plus, Talking Real Money celebrates crossing 2,000 episodes and asks listeners to follow and rate the show.
01:05 The Bond Tango: rates and bond prices
08:50 Why bonds stabilize a portfolio
16:35 BND vs. money markets and bond ladders
19:23 An unsuitable private infrastructure pitch
27:02 Celebrating 2,000 episodes
31:57 Supporting TRM and Don's story podcasts

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Ep. 2007: Follow the Money Oct 26, 2026

Show notes

Financial Physics Rule 15 says to follow the money. Don and Tom explain why an advisor's compensation still matters, how commissions and fee-based arrangements can muddy the picture, and why transparent fee-only advice and peer-reviewed evidence remain the better starting points.
Listener questions cover choosing broad, low-cost bond ETFs without panicking over tiny short-term moves, a correction to the S&P 500's streak of double-digit gains, and why Roth conversions should be evaluated year by year instead of treated as automatic.
Plus, Don detours into The Economist's look at Celebration, Florida—and discovers that Halloween trick-or-treating is really just another return-on-investment calculation.
01:00 Financial Physics Rule 15: Follow the Money
06:47 Fee-only vs. fee-based advice
16:34 Choosing bond ETFs amid rate fears
20:10 Correcting the S&P 500 streak
23:43 Roth conversions are not automatic
28:08 The town Disney built and Halloween ROI

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Ep. 2006: Five Questions, No Magic Answers Oct 23, 2026

Show notes

Don takes five listener questions with no magic tricks required: how simple a young investor’s Roth IRA can be, whether socialist economies have stock markets, and what rising U.S. debt really means for Treasury investors and the dollar.
He explains why a globally diversified fund can do most of the heavy lifting, why modern economies are hybrids rather than neat ideological labels, and how stocks, TIPS, and global diversification can help with inflation risk—without pretending there is a perfect hedge against a true dollar collapse.
Then Don tackles the hard math of creating retirement income for a recently widowed friend, including survivor benefits, immediate annuities, and a reverse mortgage, before closing with how target-maturity corporate bond ETFs can form a rolling ladder.
00:00 Friday Q&A and a Frightly October
02:46 A simple Roth IRA portfolio
04:44 Do socialist economies have stock markets?
07:43 Treasury debt, inflation, and dollar risk
13:28 Retirement income after losing a spouse
17:39 Rolling a target-maturity bond ladder
19:49 The Financial Fysicist and listener questions
22:01 Disclosures

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Ep. 2005: The Habanero Portfolio Oct 22, 2026

Show notes

A little hot pepper can improve a meal. Eating the whole habanero is another experience entirely. Can the same be said for your portfolio? Don and Tom explore why small-company, value, and profitability tilts have historically rewarded investors—and why chasing those higher returns can demand more patience than most people have. A strategy that looks terrific over decades can feel unbearable while it trails the market for years. The question is how much you can actually stick with.

Plus, a listener discovers that a value fund in his retirement plan is holding nearly half its assets in cash. Another asks whether converting a bond mutual fund to an ETF makes sense inside an IRA. And an offer from Schwab raises a tempting question: should you let your broker lend out your shares for extra income? Don and Tom examine the tradeoffs behind each decision, with an emphasis on keeping investing simple, diversified, and manageable.

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Ep. 2004: The Annuity Rules Keep Changing Oct 21, 2026

Show notes

Indexed annuities promise market-like gains without market losses—but Don and Tom explain how commissions, surrender charges, spreads, participation rates, and even changing contract terms can leave investors with disappointing returns and very little transparency.
They also discuss how much cash belongs in a retirement “reservoir,” why falling bond prices do not make high-quality bonds riskier than stocks, and how MYGA tax deferral works through a 1035 exchange.
01:31 Musical royalties and an annuity joke
02:26 Why indexed-annuity sales keep soaring
05:52 When the insurer changes the rules
11:32 Investments Don would avoid
14:41 Designing a retirement cash reservoir
22:05 Why bond-fund prices have fallen
26:22 Extending MYGA tax deferral
29:34 Free portfolio analysis
31:51 Disclosures

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Ep. 2003: Seven Styles, One Portfolio Oct 20, 2026

Show notes

Don and Tom dismantle the idea that investors need to choose one narrow “style.” Growth, value, small companies, momentum, and passive investing are ingredients—not competing identities—and the sensible answer is a globally diversified, low-cost portfolio built to work together.
They also answer questions about arranging stocks and bonds across a Roth and rollover IRA, helping a late-starting saver use a 403(b) and Roth IRA, and whether a 30-year Treasury yielding more than 5% is really a safe long-term retirement plan.
00:00 Sauce, songs, and financial simplicity
02:11 Seven supposed investing styles
07:45 Why diversification is the real strategy
11:53 Investor behavior and smarter portfolios
13:36 Building a 50/50 retirement allocation
15:52 Starting retirement savings at 46
20:37 The appeal—and danger—of a 30-year Treasury
25:07 Nashville, time warps, and episode-number confusion
31:54 Disclosures

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Ep. 2002: The Buggy Whip Theory Oct 19, 2026

Show notes

The “Buggy Whip Theory” is a reminder that even when investors correctly see the future coming, they rarely know which company—or which part of a new industry—will actually win. Don and Tom trace the lesson from ice delivery and buggy whips to streaming, airlines, and artificial intelligence.
They also explain why rebalancing is portfolio maintenance rather than market timing, what falling municipal-bond prices really mean, and how to calculate international exposure as a percentage of the stock portion of a portfolio.
00:58 The Monday financial-physics edition
02:28 The Buggy Whip Theory
06:22 Ice companies, refrigerators, and 7-Eleven
07:21 Seeing the future still doesn’t identify the winner
09:42 Artificial intelligence and the Nvidia surprise
11:11 Diversification beats prediction and FOMO
14:34 Rebalancing versus market timing
16:26 Evaluating Vanguard’s municipal-bond ETF
21:24 How much international stock exposure?
23:36 Podcast diversification and the follow button
27:57 Disclosures

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