Talking Real Money - Investing Talk

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Ep. 1786: Huh? or Duh! Dec 09, 2025

Show notes

In this special seasonal episode, you and Tom resurrect Ha or Duh, tearing through Investopedia readers’ “rules to live by” and dismantling the silliest ones with mock gravitas. Between the dad-joke arms race, a spirited defense of compounding, strong opinions on due diligence, and a surprising detour into crypto-mad zip codes, the show blends real financial guidance with holiday-season chaos. The episode also hits deeper listener questions on rebalancing, Roth vs. pre-tax strategy in high brackets, and the danger of thinking blue chips alone equal diversification.
0:04 Seasonal return of Ha or Duh and setup of Investopedia’s “investing rules”
1:32 Rule 1: Never sell because of emotions — duh
2:44 Rule 2: “Only invest in what you know” — emphatic huh
3:35 Rule 3: Good investment in a bad market — phrasing unclear, lean duh
4:26 Rule 4: Never underestimate compounding — mega-duh
5:35 Rule 5: Cash and patience as “positions” — hard huh
6:25 Segment break into calls
7:49 Back to Ha or Duh lightning round
8:33 Buy low, sell high — duh (with caveats)
9:58 “Losses are tuition you won’t get at uni” — pass
10:21 Hold for the long term — duh
11:09 Marathon, not sprint — duh
11:39 Is education the best investment? Nuanced disagreement
12:45 “Always do your own due diligence” — modified duh (about advisors, not stocks)
15:22 FOMO avoidance — duh
16:27 Final rule: Start now — biggest duh of all
17:41 Wrap-up and transition back to regular Q&A
18:06 Listener question: Finding the “sociopath son” episode
19:28 Setup for Friday’s Q&A episode
20:18 Don’s town turns into “free Disney World” during holidays
21:51 Disney hotel pricing shock and personal stories
23:42 Don’s new original Christmas story: Santaverse
24:01 Story podcasts spike; Short Storyverses mention
25:28 Listener from Bothell: 90% blue chips, 10% cash — how to rebalance?
26:39 Why blue chips aren’t diversified and the S&P concentration problem
28:52 Listener in high bracket asks when Roth beats pre-tax
30:26 SECURE Act 2.0 catch-up rules; Roth vs. pre-tax philosophy
32:10 Monte Carlo vs. unknowable future tax rates
33:26 Why all-Roth 401(k)s would simplify life
34:28 Advice: Likely stay pre-tax in 24% bracket
35:50 Shocking stats: Seattle among highest crypto-owning zip codes
37:24 Air Force bases dominate crypto ownership — why it’s dangerous
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Ep. 1785: Nobody’s Perfect Dec 08, 2025

Show notes

In this episode, Don and Tom saddle up for a tour through Schwab’s “Good, Bad, and Ugly.” They applaud CEO Rick Wurster’s warning about the growing overlap between gambling and investing, take a hard look at Schwab’s retail-side conflicts and non-fiduciary sales practices, and then recoil at the truly ugly: Schwab’s acquisition of Forge Global and its push to open private-company speculation to everyday investors. From there, they field listener questions about crypto’s pointless search for a purpose, how to implement a disciplined 5 percent retirement withdrawal strategy, the ins and outs of tax-free Vanguard mutual-fund-to-ETF conversions, and whether a younger spouse should convert a large TSP balance to Roth. It’s classic Talking Real Money: skeptical, practical, consumer-first, and mildly exhausted by the Wild West of modern finance.
0:04 Investing as the Wild West and why caveat emptor still defines the industry
0:24 Schwab’s role as custodian vs. broker and how they reshaped trading costs
1:14 Schwab’s discount-broker origins and institutional dominance
2:37 Free trades, market influence, and why Schwab became the industry’s leader
3:52 CEO Rick Wurster’s warning about gambling creeping into investing
4:43 Sports betting numbers, prop bets, and why only 5 percent come out ahead
5:54 The “bad”: Schwab retail selling and the fiduciary confusion
6:40 The “ugly”: Schwab buying Forge Global and pushing private-company speculation
7:23 Why private equity is riskier, pricier, illiquid, and over-hyped
8:17 The myth of private companies outperforming public ones
9:22 Why the Wild West persists: weak oversight, self-dealing, and revolving doors
10:48 Listener question: stablecoins, crypto legitimation, and the greater-fool problem
13:00 Currency concerns and why crypto still solves nothing
13:50 5 percent withdrawal strategy: when and how to draw from your portfolio
15:28 Rebalancing, total return withdrawals, and annual cash-flow discipline
16:47 Why withdrawals should follow rebalancing, not lead it
17:56 Vanguard mutual-fund-to-ETF conversions: how they work and why they’re useful
20:10 Expense-ratio savings vs. capital-gains distributions
20:55 TSP-to-Roth conversion question: tax-rate timing matters
22:44 Only convert if you can pay taxes from outside savings
23:08 Reminder: free adviser meetings, no sales pressure
24:10 TRM’s longevity and approaching episode 2,000
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Ep. 1784: Always Question Season Dec 05, 2025

Show notes

This Friday Q&A episode tackles a wide range of listener questions: whether someone with full pension income still needs bonds, how to fix a cluttered 403(b) invested through Corebridge, what to make of Bill Bengen’s new comments about higher withdrawal rates, how inherited IRAs are taxed over the 10-year rule, and a quick explanation of the difference between “securities” and “equities.” Along the way, Don delivers a vintage KOA radio tag, explains why simplicity beats complexity in retirement plans, and walks through why 8% withdrawal fantasies collapse under real-world math.
0:04 Friday Q&A intro and listener call-ins
1:19 Do you need bonds when pensions cover all expenses?
3:01 Why fixed income still matters (and how to gauge risk tolerance)
4:33 Listener request: Don recreates a KOA radio tagline
7:29 A messy CoreBridge 403(b): what funds to keep and how simple it can be
11:37 Target-date vs. multi-fund portfolios and a small value tilt option
12:05 Bill Bengen’s new withdrawal rate comments — does 8% make any sense?
14:07 Why high withdrawal rates implode in historical simulations
16:02 Inherited IRA: what’s actually taxed and how to plan distributions
18:35 The bracket danger of big lump-sum withdrawals
19:31 Final question: difference between a security and an equity
21:15 Why music licensing on podcasts is a nightmare
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Ep. 1783: Year-End Tax Shock Dec 04, 2025

Show notes

This episode digs into the unwelcome December surprise of capital-gains distributions, especially from actively managed mutual funds. Don and Tom break down Morningstar’s latest list of high-distribution offenders, spotlighting the astonishing 83% capital-gains payout from the Royce Midcap Total Return Fund. They compare the tax drag, costs, turnover, and long-term underperformance of these funds against index funds and ETFs, and explain why tax-efficient investing matters far more than most people realize. Listener questions cover overly complex portfolios, Edward Jones stock positions, odd-lot tender offers, and whether large-cap blue-chip stocks remove the need for bonds. The episode closes with a reminder that detailed portfolio triage is best handled in one-on-one meetings.
0:04 Capital-gains season returns and why high fund returns can still hurt
0:29 Don & Tom on weather, wardrobe, and warming up in Florida
1:30 December capital-gains distributions and why they happen
2:07 Morningstar’s warning: active funds with big capital-gains payouts
3:06 Vanguard, T. Rowe Price, and American Funds distribution levels
4:09 The biggest offender: Royce Midcap Total Return Fund
5:41 Why 35 funds will distribute more than 10% of assets
5:52 The stunning number: Royce’s 83% capital-gains distribution
6:52 Why big outflows and poor performance drive big taxable events
7:21 Royce’s turnover, tiny size, high costs, and weak long-term returns
8:47 Why it’s critical to hold active funds only in tax-advantaged accounts
10:07 ETFs vs mutual funds: tax efficiency and turnover differences
11:42 Comparing Royce to Avantis AVGE on fees, turnover, and performance
12:16 How AVGE tracks its index vs Royce’s massive underperformance
13:33 When selling an active fund before a distribution may or may not help
14:05 Listener question: overly detailed allocation request — why it needs a meeting
16:29 Why some questions require one-on-one analysis
18:20 Why Appella’s free meetings exist (and what they’re not)
20:35 Odd-lot tender offers explained
22:14 Listener: selling Edward Jones stock holdings and leaving EJ
23:42 Why small, young investors should clean up taxable accounts early
24:24 The long decline of commission-based brokerage
25:26 Bothell check-in: blue-chip stocks vs bonds
27:18 Historical returns: 98 years of total market vs small-cap value
28:49 Why bonds exist in a portfolio despite low recent returns
29:30 Closing thoughts on discipline, diversification, and realism
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Ep. 1782: Hard to Pick Dec 03, 2025

Show notes

A fast, funny Thanksgiving-weekend show where you and Tom unpack why a tiny handful of stocks drive the S&P’s returns, revisit forgotten winners like Hormel and McDonald’s, explain why “you can’t pick them in advance,” and tie it all back to building global, diversified portfolios. Listener calls cover early-retirement withdrawals with 72(t), whether AVGV should replace AVGE, a Thanksgiving relative obsessed with dividends, and a listener being pitched a 1.24% Fidelity “wealth management” upsell.
0:06 Thanksgiving haze, Manhattans, overeating, and setting up the show
2:24 Magnificent 7 vs S&P 493 and how concentrated returns distort hindsight
4:49 1985’s shock winners: Hormel, Lowe’s (the other one), Franklin Resources
7:41 The 1980–1990 decade: Hormel and McDonald’s huge runs and why none were predictable
8:10 Why you need small, value, and international beyond the S&P 500
10:58 Caller: retiring at 56, 72(t) rules, penalties, and whether IRA vs 401(k) location matters
14:28 Correction: SEPP applies only to the chosen account, not all pre-tax assets
16:36 Travel while you can: knees, age, lie-flat flights, and holiday banter
20:21 Caller: AVGE vs AVGV, value tilts, the overlap, and whether it’s worth the swap
22:49 Why AVGV exists (and why advisors may not need it)
27:35 Thanksgiving email: dividend-obsessed relative critiques VXUS payouts
29:53 What dividends really mean—and don’t—and why payout “stability” is useless
35:49 Voicemail: Fidelity wants 1.24% to “manage” half a 401(k); is it worth it? (No.)
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Ep. 1781: Cold Calls & Commissions Dec 02, 2025

Show notes

Tom and Don spend this post-Thanksgiving episode dismantling the illusion that big insurance companies—Northwestern Mutual in particular—are “financial advisors” rather than high-pressure sales organizations built on whole-life commissions. Don recounts his own early days as a Dean Witter cold-call cowboy, and the two walk listeners through a damning Guardian investigation revealing recruitment practices, high-pressure quotas, and the wealth-destroying math behind whole life. The phones open to calls about Cambridge’s nearly 3% wrap fees, sociopathic insurance sales relatives, term-insurance needs for young families, Roth vs. pre-tax decisions, and how to find a real fiduciary advisor. The theme is consistent: avoid sales machines masquerading as advice, and keep investors from being devoured by the industry’s worst incentives.
0:04 Tech glitches, Thanksgiving jokes, and Tom’s three-week vacation cadence
1:45 Why this is “not the best-of”—it may be the worst-of
2:26 Don’s Dean Witter cold-call origin story and the culture of selling, not advising
3:35 Northwestern Mutual’s rebrand and the Guardian investigation
4:08 False promises: “You’ll make $200K in three years”
5:12 The cold-calling boot camp and why only one trainee survived (Don)
6:46 Inside the student recruitment pipeline and the friends-and-family harvesting
8:11 Whole life math: the S&P at +3700% vs. Northwestern at +44%
10:50 Why whole life persists: commissions
12:41 Wrap-up of the Guardian findings and the industry’s structural sleight-of-hand
16:23 CALL: Cambridge Wealth “index” portfolio with hidden fees
23:14 The reveal: Cambridge’s small-account wrap fees approach 3% per year
25:54 CALL: Son-in-law selling insurance, knows it’s a ripoff, loves the money
28:55 Thanksgiving family drama and the “sociopath vs. psychopath” riff
29:59 CALL: How much term life insurance should a high-income parent carry?
32:52 CALL (same): Splitting Roth vs. pre-tax contributions when income is high
34:28 CALL: How to find a true fiduciary (and avoid annuity traps)
37:59 The advisor interview form and how to make salespeople disqualify themselves
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Ep. 1780: Black Friday Q&A Nov 28, 2025

Show notes

A light Black Friday edition tackles four listener questions covering Vanguard’s Digital Advisor, the timing of Social Security versus IRA withdrawals, whether to swap target-date funds for a VT/BND mix, and the wisdom (or lack thereof) of adding managed-futures ETFs. The show ends with a look at whether international bonds meaningfully improve diversification (answer: barely). The through-line? Keep investing simple, avoid expensive complexity, and stick with risk-appropriate, broadly diversified portfolios—holiday weekend or not.
0:09 Don debates doing a Black Friday episode but decides to keep listeners company
1:58 How to submit questions on the website and call on Saturdays
2:16 Q1: Is Vanguard’s Digital Advisor worth using?
2:56 Pros and cons: low cost, limited choices, avoid the active-fund version
4:29 Transition to Q2
4:55 Q2: Should a spouse take Social Security at 62 or delay and live off an IRA?
5:50 Pension changes the math—delay for the 8%/yr benefit
7:13 Target-date vs. VT/BND performance and Roth allocation logic
8:32 Risk tolerance matters more than account type
9:09 Actual performance: 2035 fund vs. VT/BND nearly identical
9:42 Q3: Adding managed-futures ETFs as a diversifier
10:23 Why Don strongly opposes adding complexity and high-expense hedges
11:36 Expense ratios make them non-starters
11:56 Q4: Should investors add international bonds?
12:46 Tiny diversification benefit; generally not worth it for DIY investors
14:38 Correlation improvement maxes out around one-tenth of one percent
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Ep. 1779: The Right Time to Retire Nov 26, 2025

Show notes

Don and Tom run through a Wall Street Journal list of “subtle signs it might be time to retire,” reacting to each one with their usual mix of disbelief, personal anecdotes, and gentle ribbing. The episode wanders into tech reluctance, job promotions nobody wants, Sunday dread, obsessive 401(k) checking, volunteering guilt, missing peers, feeling left out of friends’ retirements, boss-related misery, and aging knees. They also answer listener questions about Schwab Intelligent Portfolios and their high cash allocations, discuss the shrinking role of physical cash, explain the real value of pre-1964 silver quarters, and handle calls on Social Security math. Tom repeatedly tracks his daughter’s high-school soccer match on-air, providing live updates as the drama unfolds.
1:06 WSJ list of “subtle signs it’s time to retire” begins
1:40 Sign #1: Feeling numb arriving at work
2:11 Why neither host relates to workplace numbness
2:59 Sign #2: Shrinking from new tech tools (Tom jokes incoming)
3:40 Don embraces AI, Tom… less so
4:21 Sign #3: Avoiding promotions; why neither wants a bigger job
5:16 Sign #4: The “Sunday scaries”
5:50 Sign #5: Constantly checking your 401(k) balance
6:26 Mid-list recap before the break
7:42 Second half of the list introduced
8:57 Sign #6: Wanting to volunteer more
9:40 Sign #7: Realizing all your peers have retired
10:11 Don jokes about dying at his desk
11:34 Sign #8: Feeling left out as friends enjoy retirement trips
12:40 Sign #9: Hating your boss (and why that’s not a retirement issue)
12:56 Sign #10: Achy knees and “retire before you can’t enjoy things”
13:35 Doctors, guarantees, and aging joints
14:43 Call for listener questions
15:04 Call: Schwab Intelligent Portfolios’ big cash allocations
16:28 How Schwab makes money on the spread
18:20 Transparency vs. hidden fees
20:20 Back from break — Wednesday podcast explanation
21:31 Don hates change (the coin kind and the life kind)
22:30 Historical buying power of coins
22:56 Pre-1964 silver quarter value
24:15 Odds of finding one in circulation
25:10 What amount of money makes you bend over and pick it up?
25:47 Cleaning out the garage vs. hunting silver coins
27:36 Halftime soccer update: the comeback begins
29:02 Caller: misunderstanding “8% interest” from Social Security discussion
30:26 Caller Paul on cash vs. cashless society
31:51 Coca-Cola prices through time
32:57 Only 12–18% of payments today are cash
34:02 Holiday well-wishes and generational shifts
35:34 Bewitched, credit checks, and pre-internet detective work
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Ep. 1778: Value of Wisdom Nov 25, 2025

Show notes

This episode opens with a warning to younger investors who take TikTok advice over historical perspective, especially around claiming Social Security early. Don and Tom walk through the guaranteed 8%+inflation benefit increase from delaying, why “take it at 62 and invest it” collapses under market reality, and how fear is driving a surge in early claims. They pivot to Bitcoin’s sharp drop and why crypto speculation is driven by greed, not protection, before teasing Don’s upcoming crypto short story. Listener questions cover bad long-term-care/annuity hybrids, overcomplicated “bucket” strategies, responsible portfolio risk, and finally a breakdown of two expensive high-volatility mutual funds—both easily beaten by low-cost index alternatives.
0:04 Message to younger investors about lacking market perspective
1:19 Why TikTok advice on claiming Social Security early is flawed
2:17 The real 8%+inflation annual increase from delaying benefits
2:27 The “take it at 62 and invest it” myth
3:47 Tom recounts Paul Merriman calling his allocation aggressive
4:49 Rising panic-driven Social Security filings
5:21 Don’s 69 vs. 70 claiming decision
6:11 Survivor benefit logic many forget
7:42 Imagining a sudden 30% crash—except it’s Bitcoin
8:29 Bitcoin’s drop from 124K to mid-80s, plus MicroStrategy leverage
9:58 Crypto culture, crypto research, and Don’s upcoming story
10:58 Crypto as a greed play, not protection
12:37 Emotions sabotage investing; the plan removes them
13:51 Why risk needs to match the plan, not ego
15:24 Crypto story teaser + Short Storyverses email plug
16:31 Listener question: NY Life Asset Flex LTC pitch
17:49 Why hybrid LTC/annuity products are weak and commission-heavy
19:47 “Bucket” confusion and the need for purpose
21:30 Caller Eugene: $250K “play money”
23:43 Reality check: could you watch $250K drop to $125K?
24:06 Why timing dips doesn’t work
25:20 Better uses for excess cash in your 70s
27:08 Tom: time for full planning review at age 77
28:38 Fund analysis: Morgan Stanley Growth A
29:25 Fund analysis: Invesco Equity & Income A
30:30 Why moving to low-cost Vanguard indexes is the logical move
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Ep. 1777: Nefarious Non-Profit? Nov 24, 2025

Show notes

Don and Tom go deep on a shady “non-profit” financial education group that funnels retirees into high-commission indexed annuities, using a listener tip to unpack the advisor’s fake credentials, mismatched ADV filings, dubious fiduciary claims, and the simple math that reveals where the money really comes from. Along the way, they cover how to investigate advisors yourself, why financial fairy tales persist, and answer listener questions on Avantis gold holdings, private equity’s impact on small-cap value, and the quality of Schwab’s 529 plan.
0:04 Don’s industry rant and a look at the “American Financial Education Alliance” disguise.
1:01 How pseudo-nonprofits target advisors and consumers with “no-sales” sales pitches.
2:20 Tom’s take on the recycled seminar game and fake educator designations.
3:40 Listener tip sparks Don’s PI dive into the flyer, claims, and contradictions.
4:49 How to vet advisors using BrokerCheck and Form ADV.
5:58 The firm’s tiny AUM and impossible economics of their claimed operations.
8:02 The Maryland house vs. the Lakewood Ranch mansion — where the money REALLY comes from.
9:25 The inevitable reveal: indexed annuity commissions driving the whole machine.
10:18 Breaking down the seminar pitch language and the deceptive “market returns without risk” promise.
11:24 Why the sales story collapses under math and dividends.
12:34 The “licensed fiduciary” myth and regulatory reality for small firms.
14:38 How consumers get fooled by the fiduciary framing in seminar mailers.
16:13 Don and Tom dissect the pre-fab radio/TV show factories behind these advisors.
17:19 Why the meeting is the real sales trap — and how to avoid it.
18:48 Don’s plea: stop believing financial fairy tales.
19:26 Don jokes about infiltrating steak-dinner seminars undercover.
20:14 Transition to listener Q&A from Maryland: AVDV’s gold exposure.
21:26 Why Avantis owns gold miners without being “in gold.”
23:47 Momentum, value screens, and why the gold weight makes sense.
24:26 Gold Hill, Oregon 529 question: Is the Schwab plan good?
25:30 Age-based 529s and Schwab’s low-cost structure.
27:28 Private equity fears: will it starve small-cap value indexes?
28:41 Why the concern is mostly a media creation, not an investment reality.
29:48 Don on the IPO–private–IPO cycle and how markets actually work.
30:11 Why private equity performs worse in bad markets.
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