Don and Tom take apart a clickbait Kiplinger piece touting the “five top buy-and-hold investments to manage market volatility,” arguing that the list is a random grab-bag of recent winners rather than a coherent portfolio. They explain why the suggested mix—VOO, VXUS, a healthcare sector ETF, Apple stock, and gold—does little to reduce volatility and instead layers on concentration risk, sector bets, and performance chasing. From there, they broaden the discussion into a more useful question: where should investors actually go for trustworthy information, how should listeners think about evaluating a financial advisor, and what really matters when judging portfolio design. The back half of the episode features a thoughtful call about investing a spendthrift trust for two sons over a 12-year horizon, plus a warning that advisor performance can’t be measured by returns alone without understanding risk, asset allocation, and the planning services being delivered.

0:05 Cold open, podcast intros, and Tom’s ever-growing aircraft museum
1:40 Don tees up a Kiplinger clickbait article on the “five top buy-and-hold investments” for market volatility
2:14 Why the article’s opening about political uncertainty and inflation could apply to almost any year
3:36 The one part they agree with: long-term wealth is built by disciplined exposure to quality assets, not reacting to headlines
4:53 The rise of numbered clickbait headlines and whether numbers in titles actually matter
5:53 Why “stability” and “stock picks” don’t belong in the same sentence
6:27 Kiplinger pick #1: VOO — fine as a broad U.S. stock fund, but hardly a volatility solution
7:06 Kiplinger pick #2: VXUS — the one recommendation they think mostly holds up
8:21 Kiplinger pick #3: XLV healthcare ETF — a sector bet masquerading as a defensive holding
9:33 Why a healthcare sector fund lags a total-world approach while adding unnecessary concentration
10:28 Kiplinger pick #4: Apple stock — and why adding a single stock you already own inside the S&P 500 makes little sense
10:59 The problem with betting on one company instead of owning the economy through broad diversification
12:20 Kiplinger pick #5: gold — and why recent gains don’t make it a volatility manager
12:48 Gold’s long-term history, lack of fundamentals, and why its recent performance actually illustrates volatility rather than reducing it
14:12 The bigger issue: how do you decide which financial publications or sources are worth trusting?
15:26 Why Vanguard and Dimensional research tend to be more reliable than headline-driven finance content
16:35 The real reason people click these articles: fear, underperformance anxiety, and the urge to “improve” a portfolio
17:23 Why the Kiplinger portfolio is missing the one thing you’d expect in a true volatility-management portfolio: bonds
18:51 Don and Tom’s plea to listeners: follow evidence-based advice rather than clickbait lists
19:30 Listener call from Brian in Bremerton about investing spendthrift trusts for his sons over a 12-year horizon
20:55 The challenge: balancing growth with the possibility of distributions for education, cars, weddings, or a house
23:08 Don’s suggested framework: keep a cash/fixed-income reserve for near-term needs and invest the rest aggressively for growth
24:48 Why a target-date fund may not be the best fit for this kind of trust structure
25:37 A practical allocation idea: roughly 80/20 with a global equity fund plus a broad bond fund
26:51 Brian explains that Roth IRA funding is already part of the family’s gifting and estate strategy
27:32 A listener from Seoul praises the show and begs them not to turn into a “humblebrag retirement call-in show”
29:49 Listener question: how do you measure whether your financial advisor is performing well?
30:42 Why advisor performance should not be judged by returns alone
32:11 The importance of understanding what services you’re actually paying for: planning, rebalancing, tax guidance, income strategy, and more
33:11 What to examine in a portfolio besides returns: risk level, asset allocation, and whether key asset classes are missing
34:11 Why even benchmark comparisons can be misleading if the portfolio isn’t properly diversified
35:18 The better question: is your advisor delivering the services and portfolio design you actually need?

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Can Tom beat the average American on a personal finance quiz?

Don puts Tom in the hot seat with eight questions drawn from a financial literacy quiz developed by researchers at Stanford University and TIAA. The topics range from earning, budgeting, inflation, investing, debt, insurance, and risk to evaluating investment advice. Along the way, there’s plenty of good-natured ribbing, a debate over compounding, and a reminder that even financial professionals can stumble on carefully worded questions.

Later, the guys answer listener questions about whether the small-cap value premium still exists despite the rise of private equity, and whether exotic portfolios like the “Golden Butterfly” really deserve their impressive back-tested reputations.

Plus, Tom gives an enthusiastic endorsement of Don’s Civil War novel, The Line Uncrossed.

00:18 – Tom faces an eight-question financial literacy quiz
03:49 – Inflation versus savings: the trickiest question
05:53 – Why diversification beats owning a single stock
07:11 – The power—and danger—of compound interest
08:50 – Insurance coverage young adults actually need
09:52 – Expected value and lottery math
11:10 – Appropriate investments for different ages
12:40 – Why compounding may be the most important concept in investing
13:39 – Which asset classes have historically produced the highest returns?
16:03 – Does the small-cap value premium still exist?
23:01 – Should investors trust the Golden Butterfly portfolio?
26:45 – Tom’s review of The Line Uncrossed
29:17 – Free meetings with Appella advisors
31:11 – Blue shirts, blue eyes, and wrapping up

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Don and Tom tackle the blurry line between free speech and market manipulation after the conviction of prominent short seller Andrew Left. They debate whether financial influencers should be allowed to profit from public stock recommendations, discuss why members of Congress continue trading individual stocks despite widespread public opposition, and explain why ordinary investors should avoid trying to outsmart people with superior information or influence.

The conversation then shifts into listener questions covering Roth employer matches, Roth IRA withdrawal rules, Roth conversion strategies for retirees, and whether paying taxes now simply to benefit heirs makes financial sense. Along the way, there’s plenty of lighthearted banter about soccer, politics, podcast reviews, and Don’s growing passion for his Litreading short story podcast.

00:05 – Introduction and Independence Day reflections
01:27 – Andrew Left convicted of stock market manipulation
03:24 – Is market manipulation protected free speech?
06:56 – Why Don opposes congressional stock trading
09:18 – Congress made over 13,000 stock trades in 2025
12:29 – Why public officials should be held to a higher standard
14:12 – The lesson for ordinary investors: you can’t beat insiders
15:27 – Podcast reviews, politics, and avoiding crypto
17:12 – Florida’s proposed property tax amendment
18:22 – Transition to listener questions
19:38 – Employer Roth 401(k) matching contributions
20:10 – Can you withdraw Roth IRA money before age 59½?
21:49 – Should retirees convert large IRAs to Roth accounts?
24:52 – Soccer, World Cup talk, and the “laws” of the game
26:44 – Don promotes Litreading and Short Storyverses

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