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!