Talking Real Money - Investing Talk

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Ep. 1776: Speak Your Qs Nov 21, 2025

Show notes

A lively Friday Q&A episode tackling listener questions about FSAs vs. 401(k) contributions, BND vs. BKAG bond funds, intermediate-term bonds vs. CD ladders, Avantis fund-of-funds fees and structure, and the financial implications of New York City’s newly elected socialist mayor. The show blends practical investing guidance with jokes about annuity-salesperson Halloween costumes and a detour into political fears vs. economic realities.
0:04 Opening, Friday Q&A setup, thanks to Tom’s grandkids
0:44 Listener FSA dilemma and choosing between FSA funding or 401k
3:01 Why FSAs are painful and why a 401k wins when choosing one or the other
5:57 Comparing BND and BKAG bond funds, holdings, universe, credit quality
9:01 Listener joke: “scariest Halloween costume is an annuity salesperson”
9:55 Moving CD-ladder money to VGIT or BIV; differences and trade-offs
12:22 Thoughts on iShares LifePath target-date ETF (ITDC)
12:33 Why Avantis fund-of-funds exist and whether you pay double fees
15:36 Underlying fund costs inside AVGE and how the total expense ratio works
16:21 Question about NYC’s new socialist mayor and financial impact fears
17:54 Walking through political fears vs. practical economic reality
21:55 Why one politician can’t radically reshape a city’s economic fate
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Ep. 1775: Good Enough Nov 20, 2025

Show notes

You and Tom spend this episode unpacking a surprisingly liberating idea for investors: that average is good enough. Kicking off with your own story about a two-star podcast rating, you two stumble into a bigger truth—most people are chasing a level of portfolio perfection that doesn’t matter. Christine Benz’s Morningstar piece becomes the backbone of the discussion, contrasting “maximizers” (engineers, tinkerers, over-optimizers) with “satisfizers” (simple, diversified, sane). From there you hit Tesla’s trillion-dollar pay package drama, Bito’s goofy “dividends,” SGOV vs. CD ladders, fears about private equity sneaking into retirement plans, and a few classic Don-and-Tom tangents. The message: stop overthinking, build a sensible portfolio, and go live your life.
0:04 Don’s two-star review existential crisis and the epiphany about doing things for joy
1:16 Why being “average” in investing (and life) is perfectly fine
1:45 Elon Musk compensation debate and ETF shareholders not getting a vote
3:12 Don’s “brilliant raving lunatic” take on Elon and Tesla’s dominance
4:38 The kings of tangentiality finally introduce the show
5:55 Christine Benz and the “Good Enough Portfolio” philosophy
6:36 Maximizers vs. satisfizers explained (plus Bogle bobbleheads)
8:53 Why over-optimization rarely improves results
9:56 Happiness and second-guessing: satisfizers win
11:22 Time costs, tax worries, and the illusion of finding a perfect portfolio
12:33 Two-fund vs. ten-fund portfolios and why simplicity works
13:55 Working harder doesn’t usually make you richer—your job does
14:25 Listener letter: long-time fan from Silverdale reminisces about 1988
15:26 Tom recalls being put on the air after several glasses of wine
16:03 Acorns user asks about BITO’s wild “dividends”
18:10 Why BITO’s payouts are actually return of capital and cannibalization
19:58 BITO’s volatility roller-coaster (standard deviation 53)
20:12 SGOV vs. CD ladders for short-term retirement cash
22:07 Why emergency funds shouldn’t sit in a Roth IRA
22:58 Listener concerned about private equity creeping into 401(k)s
23:52 PE risks, political pressure, and greater-fool concerns
25:27 Don thanks listener “AlwaysLearning1953” for the positive review
26:49 Murder of Crows, sound effects, and the power of scary crows
27:36 New Tales Told update—more stories on the way
28:38 Saturday live show reminder and flyover banter
28:58 Don’s Kansas/Leavenworth childhood story detour
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Ep. 1774: Simple Solutions Nov 19, 2025

Show notes

Don and Tom open with the investor mistakes Christine Benz highlighted in Morningstar: portfolio sprawl, concentration in the same large-cap tech names, clinging to ancient active funds, ignoring reallocations, and failing at both asset allocation and asset location. The show then shifts into calls—first about fears of an “AI crash,” then a heartbreaking case of an 80-year-old widow stuck in an expensive, incoherent Schwab-built portfolio, which Don dismantles live. Later, Roth conversion strategy, smishing scams, and a closing riff on Bitcoin’s extreme volatility versus gold. A packed episode on how bad habits, high fees, and fear derail investors—and how a simple, globally diversified plan avoids most of it.
0:04 Intro and Christine Benz’s list of common portfolio mistakes
0:56 Portfolio sprawl and “hodgepodge-itis”
1:32 Overloaded baskets of large-cap tech stocks
2:52 The 31-year-old underperforming fund problem
3:54 Active vs. passive: the shift the industry still hasn’t admitted
4:03 Asset allocation errors driven by ignoring the plan
4:51 Why rebalancing matters (and why people never do it)
5:40 Asset location mistakes and why taxes demand a smarter structure
6:15 Why these errors are easy to fix with a simple plan
7:58 Don solo; open phones
8:23 Caller: Fear of an “AI crash” and whether it can tank the market
11:16 Building a portfolio that can withstand any crash
13:01 International ballast and why planning matters more than predictions
14:27 Don solo again; open phones
15:17 Smishing scams and the rise of SMS-based fraud
16:13 How cheap scam-software makes fraud explode
17:08 Caller: 80-year-old widow with an awful Schwab portfolio
18:27 Don investigates the tickers—high fees, obscure funds, bad structure
19:57 Schwab dropped her; Don: “This advisor should be fired”
21:07 Why the portfolio lost money and what those numbers really mean
22:26 Active funds, high turnover, and tax drag
24:01 Don’s verdict: unload the mess and move to simple, low-cost indexing
25:01 Why a target-date fund may be the cleanest fix
26:33 Take the risk quiz; why advisors should be boring
27:00 Don vents about industry incompetence and fee-only failures
28:23 Why advisors chase “exciting” instead of sound
30:02 Caller: Roth conversion when 70% of assets are in traditional IRAs
31:25 Why conversion benefits are minor but sometimes worthwhile
32:33 Strategy: convert up to top of the 24% bracket
33:19 Wrap-up and call for last questions
34:56 Gold vs. Bitcoin: which is actually stable?
36:09 Why Bitcoin’s volatility makes it a terrible “currency”
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Ep. 1773: No Absolutes Nov 18, 2025

Show notes

You and Tom take on the myth of hard-and-fast financial rules by walking through Real Simple’s list of nine “rules you can break.” From the latte factor to credit cards, budgeting, bulk shopping, and the old “retire at 65” trope, the conversation keeps coming back to a single theme: money isn’t black and white. You push back against absolutists like Dave Ramsey, emphasize discipline over dogma, and highlight the practical realities of saving behavior, debt, lifestyle choices, and risk. Listener calls round it out — including a thoughtful inheritance question and a late-career investor worried about having “run out of time,” which you defuse with smart, flexible solutions.
0:04 Absolutism vs. nuance in personal finance
1:24 Dave Ramsey’s black-and-white rules
1:57 The latte rule and small vs. big expenses
3:36 Pay-yourself-first as the only rule that really works
4:57 Are credit cards bad? Protection, perks, and pitfalls
6:26 Truth lives between extremes
7:45 “Breakable” money rules from Real Simple
8:39 The myth of retiring at 65
9:59 Why more people work past traditional retirement age
11:00 Don’s TV story and accidental age-compliment
12:59 Is bulk shopping really a money saver?
13:55 Why strict budgets fail
15:04 Tom’s failing FaceTime and tech-phobia
16:02 Caller: leaving money to grandkids who vanished
19:43 Family lawsuits when inheritances differ
20:23 Caller: asset location and bond placement
24:55 Should you draw from 401(k) or IRA first?
28:43 Caller: “Am I out of time to retire?”
33:00 Solving retirement shortfall with portfolio structure
36:16 Don runs the numbers — immediate annuity option
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Ep. 1772: Retirement Robbers Nov 17, 2025

Show notes

A listener’s nightmare 401(k) story sparks a deep dive into how small employers can delay, misuse, or even lose employee retirement contributions before they ever reach the plan custodian. Don and Tom explain the Department of Labor’s weak enforcement, why small plans are most vulnerable, and what workers must do to protect themselves. Then the show tackles backdoor Roth timing rules, Social Security “worst-case” planning, the appeal (or lack of) of mid-cap ETFs, and how to unwind a hodgepodge portfolio without triggering massive tax bills.
:04 When employers steal 401(k) contributions before depositing them
1:42 The WSJ case: three-year hunt for missing contributions
3:02 Why small employers are the highest-risk group
5:02 DOL enforcement loopholes and the “administratively feasible” dodge
7:04 What to do if your contributions never show up
8:09 Fidelity bonds, audits, and how recovery really works
9:39 Big-company plans vs. small plans
10:36 Inside the Amazon layoff notice fiasco
11:54 Listener question: timing a backdoor Roth in 2026 for the 2025 tax year
13:40 The Form 8606 trap and pro-rata consequences
15:03 Listener question: Should you assume Social Security cuts in your plan?
16:41 Why benefits probably won’t be cut—even though the system needs fixing
18:04 Listener question: Should anyone buy a mid-cap ETF?
18:46 Why good portfolios already own plenty of mid-caps
19:36 Listener question: Fixing 20 years of hodgepodge-itis at age 72
21:22 Taxes, capital gains, and the slow cleanup strategy
23:52 Why Wellington and Wellesley don’t fit a modern portfolio
25:20 Personal banter: vacations, spending guilt, and sci-fi
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Ep. 1771: More Money Q&A Nov 14, 2025

Show notes

Don fields a full slate of listener questions on everything from SGOV vs. high-yield savings accounts to the differences between AVUV and DFSV, why international stocks belong in a portfolio (but shouldn’t dominate it), and whether equal-weighted funds solve the “Magnificent 7” concentration problem. He digs into target-date and bond-fund suitability for short-term money, clarifies what “rules-based” really means for Avantis and Dimensional, and gently deflates misconceptions about long-term international outperformance. Along the way he riffs on talk radio’s decline, teases Tom’s dad jokes, and reinforces the core message: diversify, know your time horizons, and don’t overthink what good academic research already tells us.
0:04 Don opens Q&A Friday and reflects on radio’s slow fade
2:20 SGOV vs. high-yield savings accounts for emergency cash
5:13 Why AVUV and DFSV only overlap ~40% despite similar factors
8:43 Which fund is “wilder”: AVUV vs. DFA small value
9:54 Why international stocks belong in a portfolio—but not overweighted
11:41 Long-term U.S. vs. international return history
14:51 S&P 500 concentration and equal-weight ETF considerations
18:44 Equal-weight vs. small-value tilt vs. rules-based funds
20:07 Where to put 2–3 year money: savings, CDs, BND, or a near-dated target-date fund?
23:13 Better language than “active”: rules-based vs. systematic
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Ep. 1770: Annuity Reality Nov 13, 2025

Show notes

Don and Tom question a surprising Wall Street Journal column arguing that annuities should become the default option in 401(k) plans. They explore why the idea is gaining traction, where the logic breaks down, and how the insurance industry benefits when complexity outpaces understanding. Along the way, they dig into the real shortcomings of annuities—fees, opacity, inflation risk, liquidity traps—and why “guarantees” often mask the true cost. Listener questions follow, covering tax-efficient stock cleanup at Schwab, spouse disagreements over individual stock picking, automatic ETF withdrawals at Vanguard, and building Dimensional portfolios inside Aspire plans.
0:04 Don’s rant: “What the world needs now is… more annuities?”
1:20 WSJ’s argument: make annuities the 401(k) default
2:05 Why income complexity doesn’t justify default annuities
3:01 Do annuities actually solve longevity risk?
3:29 Inflation, joint-life costs, and who really wins
4:20 Insurance industry reputation and the unanswered criticisms
5:15 High fees, opacity, and why mistrust is earned
5:59 Are annuity sales tactics the real barrier?
7:02 Should annuities be in 401(k)s at all? Don vs. Tom
7:36 Why annuities are mostly sold, not bought
9:10 Liquidity traps and major-life-event risks
10:01 Why “plans” matter more than “products”
10:57 Listener questions: why nobody calls anymore
11:14 Q1: Selling a brokerage full of individual stocks at Schwab
12:46 Q1b: How to convince a spouse who loves stock picking
14:21 Indexing vs. anecdotal evidence
16:21 SPIVA data and why active managers lose
17:02 Q2: Can Vanguard automate ETF withdrawals?
19:05 Fractional shares and why purchases are allowed
20:25 Q3: Aspire 403(b) options and DFA overload
23:46 How many DFA funds do you really need?
24:44 Micro-cap risks and portfolio sprawl
25:42 Tom’s pumpkin-patch grandkid cameo
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Ep. 1769: Z Good and Z Bad Nov 12, 2025

Show notes

Tom and Don grade Gen Z investors from a recent Wall Street Journal article, discussing their portfolios, common mistakes like stock picking, active management, and crypto speculation. They move into practical retirement and college-planning questions from callers — including Roth vs. taxable accounts, 401(k) catch-up contributions, 529 plans, and college costs pushing $90 K a year.
0:04 Gen Z investing habits and media influence
1:59 Grading five young investors from a WSJ profile
7:43 Financial-flinch reflex and planning plug
12:21 Listener: starting a 401(k) at 59
15:34 Listener: using taxable funds for a Roth contribution
20:24 Listener: Roth 401(k) catch-ups and 529 trade-offs
26:08 College costs and saving priorities
28:43 Listener: opening a 529 for a grandchild
36:12 Listener: portfolio check (AVUV + bond ladder) and AVGE recommendation
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Ep. 1768: Investing Is Dull Nov 11, 2025

Show notes

Don and Tom tackle investor “magical thinking,” especially the belief that private equity, non-traded REITs, and other illiquid “exclusive” investments offer hidden superior returns. They walk through Jason Zweig’s recent reporting on a Florida pension fund that locked up money, paid higher fees, and earned under 1% a year. The conversation underscores why liquidity, transparency, and diversification matter far more than complexity or exclusivity. The episode also features listener questions on retirement withdrawal sequencing for a $9M portfolio, evaluating cash balance plans, and deciding between traditional vs. Roth 401(k) contributions. A recurring theme: boring portfolios win.
0:05 Magical thinking and the fantasy of “special” investments
1:52 Private equity realities: higher fees, no liquidity, often lower returns
2:46 The Indian Shores pension fund case
3:44 Withdrawal limits and 0.7% 5-year returns
4:34 Why endowments can do illiquid assets but you probably shouldn’t
5:21 “Roach motel” investing and lack of transparency
8:35 How mutual funds must provide daily liquidity vs. private funds that don’t
8:49 Excitement is bad; investing should be boring
9:54 Caller: $9M portfolio—withdraw taxable first or convert IRAs?
11:51 Traditional IRAs vs taxable sequencing strategy
14:17 Why taxable first lowers tax impact and preserves flexibility
16:03 Blackstone senior housing REIT losses and why “sure things” fail
17:39 Diversification protects you when single bets go bad
18:06 Why private deals appeal emotionally (exclusivity + status)
20:38 Caller: Tesla & concerns about private equity creeping into ETFs
23:07 Why mainstream ETFs won’t adopt illiquid private assets
24:43 REIT ETFs behave more like stabilizing bond substitutes
26:02 LeaveMeAlone email-unsubscribe tool discovery
28:04 Listener questions: send via site or voice form
30:51 Cash balance plan concerns—likely a stable value/insurance product
33:08 Another listener: Edward Jones 401(k) with American Funds C-shares
34:30 High-fee small-plan 401(k)s—why they happen and how to fix
36:27 Caller: Should we switch to Roth 401(k) contributions? Probably not here.
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Ep. 1767: Bring the Card Nov 10, 2025

Show notes

Tom welcomes consumer advocate Herb Weisbaum (ConsumerMan) to talk through the rising headaches of modern travel and everyday scams. Herb shares a recent Delta Airlines ordeal where he was nearly stranded overseas because he didn’t have the exact credit card used to purchase his ticket months earlier — a policy he and others say is poorly disclosed and inconsistently enforced. The conversation expands to robocall loan scams, fake toll violation texts, and AI-boosted fraud that’s becoming harder to spot. Herb offers practical steps on how to avoid getting trapped, plus early holiday shopping advice as tariffs and supply issues push prices up. A lively, useful consumer-protection episode.
0:10 Tom introduces Herb Weisbaum and today’s consumer-focused discussion
1:14 Tom’s Heathrow airline mess and why travelers feel powerless
2:08 Herb’s far worse Delta experience: denied boarding without original credit card
3:44 Calling a neighbor at 3am to photograph the card and save the trip
5:13 Delta’s justification: “We’re protecting you from fraud”
6:20 Why airlines can mistreat travelers and get away with it
7:04 U.S. vs. EU passenger rights and compensation differences
8:32 Text scams: fake unpaid toll notices are surging
9:46 The new wave of “pre-approved loan” robocall scams
10:48 AI makes scam messages grammatically perfect and harder to detect
11:04 Slow down, don’t engage, verify before responding
12:20 Let unknown calls go to voicemail to avoid social pressure
14:07 Holiday shopping preview: tariffs, supply constraints, scarcity in decor and toys
15:55 Black Friday all season long—price tracking and refund requests
16:27 Brief detour into kid gifts, backpacks, and questionable plush monsters
17:21 Checkbook.org and ConsumerMan resources for unbiased help
18:17 Herb’s love of model trains and signing off
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