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?

Questions? Comments? Click!

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

Questions? Comments? Click!

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

Questions? Comments? Click!

Are you keeping too much money in cash because you’re waiting for the “right time” to invest? In this episode, Tom and Don explain why market timing has historically been one of the costliest investing mistakes—and why even the worstinvestment timing has dramatically outperformed sitting on the sidelines.

They also answer listener questions about immediate annuities, I Bonds, portfolio allocation, sequence-of-returns risk, and why using whole life insurance as an investing strategy is a bad idea.

00:05 – Why so much money is sitting in cash
03:21 – Americans hold over $20 trillion in cash-like accounts
05:08 – The enormous cost of waiting to invest
07:27 – Morningstar’s “Mind the Gap” study and investor behavior
10:41 – Cash is trash (except when it isn’t)
11:41 – How to earn more on your bank savings
15:55 – Should immediate annuities count as bonds in your portfolio?
17:23 – I Bonds vs. TIPS and inflation protection
19:50 – Is 20% cash too much in retirement?
20:43 – Whole life insurance for sequence-of-returns risk?
22:28 – Why the advisor’s recommendation raises red flags
23:39 – The real way to manage sequence risk in retirement

Questions? Comments? Click!

This week’s Friday Q&A is packed with six listener questions covering some of the biggest financial decisions people face before and during retirement. Topics include whether actively managed bond funds are worth the extra cost, how the new senior tax deduction may affect Roth conversions, whether a 24-year-old should keep a whole life insurance policy, financial planning before marriage, the role of mid-cap funds, and whether it’s worth abandoning a target-date fund before retirement. If you’ve ever wondered whether you’re making your portfolio more complicated than it needs to be, this episode is for you.

00:00 Welcome and Fourth of July schedule update
02:21 Active vs. passive bond funds: Avantis, Dimensional, or BND?
05:00 Using the new senior deduction to reduce Roth conversion taxes
08:01 Does a 24-year-old need whole life insurance?
10:35 Money conversations every engaged couple should have
15:53 Are mid-cap funds worth owning?
17:52 Should you leave a target-date fund before retirement?
23:37 How to submit your own questions

Questions? Comments? Click!

Why do so many retirees struggle to spend money they’ve spent decades saving? Don and Tom explore the psychology behind retirement spending, including the fear of running out of money, the reluctance to touch principal, and how guaranteed income sources like Social Security, pensions, and even simple immediate annuities can make retirees more comfortable enjoying their wealth. They discuss practical strategies for creating spending confidence, the importance of comprehensive retirement planning, and why delaying meaningful experiences can be riskier than spending. The episode also answers a listener question about setting up a Roth IRA for a teenager and examines the latest uncertainty surrounding 529-to-Roth transfers.

0:05 Introduction: Why retirees struggle to spend money they can afford to spend
1:36 Fear of running out versus fear of missing out in retirement
2:52 Why even millionaires worry about spending their savings
3:51 The saver mentality and the challenge of switching to spending mode
4:47 Research shows many retirees barely touch their nest eggs
5:29 YOLO, aging, and the reality of declining mobility later in life
6:02 Why retirees prefer spending Social Security, dividends, and interest over principal
8:04 Travel, aging, and the danger of postponing experiences
8:49 Creating confidence through retirement planning
9:56 Using Social Security and RMDs to cover essential expenses
10:12 Flexible withdrawal strategies for retirement spending
11:39 Could a simple immediate annuity help retirees spend more confidently?
12:42 Healthcare costs, aging, and changing spending patterns
13:30 Recency bias and how it distorts retirement decisions
14:48 Why lifelong savers have trouble becoming spenders
16:27 Summer slowdown and a request for more listener questions
17:58 Listener question: Setting up a Roth IRA for a 19-year-old daughter
19:16 Evaluating Avantis ETFs and M1 Finance for a young investor
19:48 Why a single-fund solution may be better for small accounts
20:56 The importance of emerging markets exposure
22:40 Understanding 529-to-Roth IRA transfer rules
24:33 The unanswered question of beneficiary changes and the 15-year rule

Questions? Comments? Click!

Tom welcomes legendary investor educator and longtime friend Paul Merriman for a wide-ranging conversation about the evolution of indexing, the proposed changes to the S&P 500, and why investors should understand both the strengths and limitations of traditional index funds. Paul explains why firms like Dimensional Fund Advisors and Avantis Investors use a more flexible, evidence-based approach than traditional indexing and discusses how academic research has reshaped portfolio construction over the past several decades.

The discussion also explores lessons from market history, including the importance of understanding major bear markets, determining appropriate risk levels, and building portfolios that align with personal goals rather than chasing maximum returns. Paul shares insights from the latest Dimensional Matrix Book and explains why he believes studying 100 years of market data helps investors stay disciplined during inevitable downturns.

Finally, Paul introduces a simple but powerful strategy for helping newborns and young children build substantial retirement wealth through small annual investments that can compound over many decades.

Timestamps

0:11 Special guest Paul Merriman joins Talking Real Money
0:55 Long friendship and investing partnership between Tom and Paul
1:20 S&P 500 rule changes and earlier inclusion of major IPOs like SpaceX
2:07 Historical examples of S&P 500 additions and omissions
2:35 Microsoft’s delayed entry into the S&P 500
2:56 NVIDIA replacing Enron in 2001
3:29 How index rule changes can affect future returns and volatility
4:08 Why indexing remains the preferred strategy for most investors
5:16 Traditional versus non-traditional index funds
6:37 How Avantis and Dimensional incorporate factors beyond company size
8:05 Why factor-based investing differs from traditional indexing
9:02 Problems with rigid index reconstitution schedules
10:16 Momentum, flexibility, and portfolio management advantages
11:22 Introduction to Dimensional’s annual Matrix Book
11:53 Using market history rather than forecasts to guide investing decisions
13:09 Lessons from past bubbles, crashes, and lost decades
14:20 Why Paul trusts academic research more than Wall Street forecasts
15:14 The case for small-cap value investing
15:49 Clarifying Paul’s allocation to small companies
16:53 Investing for heirs, charities, and future generations
18:10 Remembering investor panic during the 2008 financial crisis
19:18 Determining an appropriate risk level for retirement portfolios
20:43 Different investor goals: beating the market, maximizing returns, or minimizing risk
21:28 Peace of mind versus maximum growth
21:55 Helping young people build retirement wealth early
22:54 The $365-per-year retirement funding concept
24:09 Final thoughts and appreciation between Tom and Paul

Questions? Comments? Click!

Tom welcomes consumer advocate and longtime journalist Herb Weisbaum to discuss the surprisingly expensive and increasingly chaotic summer travel season. Herb explains why airfare and travel costs remain elevated, why airline prices may not fall even if fuel costs eventually decline, and how travelers can save money through flexibility, airline perks, and smart planning. The conversation also explores travel insurance, airline schedule cuts, baggage fees, vacation-rental scams, fake airline customer-service numbers, and the importance of using credit cards rather than debit cards for travel purchases. The episode is packed with practical consumer-protection advice for anyone traveling this summer.

0:05 Introduction to consumer advocate Herb Weisbaum and the challenges facing travelers this summer.
0:55 Airfare surge: domestic fares up roughly 18% year over year and international fares up about 8%.
1:23 Why airline ticket prices may stay high even if fuel costs eventually decline.
2:38 Airline executives signal that fare increases could become permanent if demand remains strong.
3:10 Strong travel demand despite higher prices and the impact of reduced low-cost competition.
3:42 Concerns about consumers financing vacations with credit cards and buy-now-pay-later programs.
4:36 Strategies travelers can use to reduce costs despite rising fares.
4:58 Rising checked baggage fees and how airline credit cards or elite status can help avoid them.
5:42 The value of flexible travel dates and considering less-crowded destinations.
6:30 Why booking trips sooner rather than later may be advantageous.
7:04 Travel insurance considerations, including “cancel for any reason” coverage.
7:39 Basic travel insurance limitations and war-related exclusions.
8:03 Airlines reducing schedules and eliminating routes because of fuel and operational pressures.
8:42 International carriers cutting thousands of flights and what it means for travelers.
9:24 Why this may be the most unpredictable travel season since the pandemic.
10:02 Practical advice for travelers facing uncertainty and disruptions.
10:18 The importance of airline apps for rebooking and managing travel disruptions.
10:42 Growing scams involving fake airline customer-service phone numbers appearing in search results.
11:46 A simple clue that a customer-service number may actually be a scammer.
12:19 Credit cards versus debit cards for travel purchases and fraud protection.
13:57 Why wire transfers, cryptocurrency payments, and peer-to-peer apps create major consumer risks.
14:58 Vacation rental scams involving major booking platforms.
16:25 A real-world family reunion rental scam and the challenges of obtaining refunds.
18:03 Differences between how major vacation-rental platforms handle payments and disputes.
18:59 World Cup travel, ticket scams, and avoiding fraudulent offers.
20:50 Why major events create ideal conditions for scammers.
21:46 Herb shares where listeners can find his articles, podcast, and consumer resources.

Questions? Comments? Click!