Don swats a studio bug, then swats down the idea of dividend-driven retirement portfolios. Drawing on Jason Zweig’s interview with Richard Thaler, they explain why retirees should focus on total return—spending from a diversified portfolio rather than chasing yield. They hit Robinhood’s profit model, bid-ask spreads, and the need for automatic-enrollment retirement plans. A listener call leads to a discussion of Social Security timing, debt-free retirement, and (yes) hodgepodge-itis—Don’s term for chaotic portfolios. Things wrap with a jailed investor’s question, some gallows humor, and the usual banter about holidays and compliance.

0:04 Bug chaos and phone-line reminder

1:41 Why dividend-income portfolios are a trap

2:50 Jason Zweig & Richard Thaler on total-return spending

4:18 Total return beats “high-dividend” illusions

5:39 Robinhood’s option-spread profits and the myth of “free” trading

6:15 Schwab vs. Robinhood: relative honesty in bid-ask spreads

7:43 Thaler’s take on missing retirement plans and automatic savings

9:05 Anniversary talk and the failed “Debbie Show” experiment

10:15 Back to Thaler—why most workers still lack plans

11:39 Tesla options example showing 7 percent spread

12:05 Case for national retirement depository & hybrid Social Security

13:33 Hodgepodge-itis defined (and owned by Don)

14:51 Low call volume and the Mariners’ hangover

15:52 Listener Kevin asks about dividends vs. selling stock

16:53 Reinvesting dividends vs. total-return withdrawals

18:17 Dividends reduce company growth potential

19:45 Why high-yield chasing kills diversification

20:07 Caller David, age 67, plans retirement & asks how to prep

21:55 Social Security timing advice—benefits rise monthly

22:50 David’s details: city pension, deferred comp, house, no debt

24:07 Getting professional fiduciary advice before retiring

25:23 David’s crypto confession and $3K Ripple gamble

27:27 Jail-bound investor asks where to park money

30:18 Don & Tom debate investing from behind bars (humor intact)

33:19 Columbus Day scheduling confusion & closing banter

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Don and Tom open with banter about the weather, baseball playoffs, and studio quirks before diving into what it means to be a “millionaire” today versus in 1890. They explore how much of modern net worth is illiquid, why home equity and retirement funds can trap wealth, and how planning for liquidity and income is crucial. The conversation transitions into a discussion of market volatility, rare earth trade tensions with China, and Brett Arends’ critique of index investing. They counter with historical perspective, humor (and potato chips), and advice about risk, rebalancing, and human behavior. Later, listener calls cover portfolio structure, Empower vs. Vanguard advisor options, and evaluating advisor fees and fund costs. The show closes with their classic blend of education, sarcasm, and fiduciary realism.

0:04 Opening banter, phone number, Florida “cold front,” and baseball chatter

2:33 Topic intro: What a million dollars means now vs. 1890

3:58 Comparing historic vs. modern millionaires and net worth equivalency

4:43 The illusion of wealth—why 70% of assets are often inaccessible

5:30 Planning for liquidity: why paying off a mortgage too early can backfire

6:37 Don’s retirement planning promo

7:39 Historical comparison: 1890s Gilded Age vs. today’s millionaire stats

8:19 Market globalization and modern wealth concentration

9:43 Rare earths and the U.S.–China tariff skirmish

10:22 Market check: stocks, bonds, and gold all dip; volatility talk

12:04 Don’s “unnamed thing” (Bitcoin) drops 10.5%; discussion on risk and rebalancing

13:48 Don shifts to 60/40 allocation—explains rationale near retirement

14:34 Brett Arends’ “Dumbest Stock Market in History” critique discussed

16:00 Debate: Are index investors stabilizing markets through consistency?

17:19 Potato chip tangent and investor psychology

18:32 Arends’ bearishness vs. evidence-based investing

20:00 Protecting your psyche, not every dollar, from market declines

20:20 Podcasting history—when Talking Real Money began

21:32 Caller Samir (Virginia): $4M net worth, suffering from “hodgepodge-itis”

24:15 Don and Tom’s prescription: stop investing until you have a plan

25:42 Margin loan temptation and why 10.5% interest kills the idea

27:00 Tom reinforces the need for a fiduciary planner

27:32 Caller Chris (Texas): moving from Empower to Vanguard PAS

29:21 Vanguard vs. Empower: conflicts, fund choices, and planning gaps

31:46 “Half-pregnant” advice models and Bogle’s legacy examined

34:20 Broader critique: single-provider risk and investor behavior

35:54 Caller Dave (Olympia): evaluating returns, fees, and portfolio costs

37:50 What’s a reasonable expense ratio and advisor fee range

39:24 Final takeaway: judge portfolios by structure, not short-term returns

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In this playful and insightful episode, Don and Tom explore how the beloved Friends characters might fare financially if they were retiring today. Using their signature mix of humor and practical investing wisdom, they analyze each character’s fictional career, personality, and spending habits to project their retirement readiness. The second half of the show returns to real-world money matters, answering listener questions about blending withdrawal strategies and fund choices in employer retirement plans.

0:04 Why this episode starts with a Friends reference—and yes, it’s copyright-friendly

0:31 Monica and Chandler Bing as retirement savers: organized, driven, but maybe too perfectionist

3:25 Monica’s obsessive planning vs. Chandler’s possible risk aversion

4:22 Overthinking portfolios and the emotional toll of too much tweaking

5:01 Savers who struggle to spend: how Monica might hoard instead of enjoy

5:56 Chandler’s likely financial behavior and their combined million-plus portfolio

7:03 Ross: neurotic, divorced, and probably pension-supported

7:54 Why pensions are psychologically powerful for retirees

8:35 Ross would need an advisor to keep him calm and invested

9:14 Rachel: spender, low earner, fashion industry job—not retirement ready

10:30 Joey: the actor’s feast-or-famine finances and SAG-AFTRA pension potential

12:22 Real SAG-AFTRA pension expectations: modest but helpful

13:09 Joey’s likely retirement: modest income, limited comfort outside major cities

13:54 Phoebe: quirky, lovable… financially reckless?

14:28 Phoebe’s imaginary downfall: alimony, bad investing, busking in Times Square

15:20 Big picture takeaways: personality, income, and circumstance aren’t destiny—but they shape outcomes

16:48 The Bings win the retirement game… Phoebe’s husband probably doesn’t stay married

17:30 Listener Q1: Combining fixed and flexible withdrawal strategies

18:52 30-year portfolio simulation using 60/40 and AI tools

20:24 Hybrid strategy results: high survival rate, smoother ride, and growing payouts

21:21 Comparison of 4% vs. 5% withdrawal income over time

22:36 Listener Q2: Replacing expensive international funds in a union 401k plan

24:00 Replace EuroPacific and Developed with Fidelity’s low-cost international index fund

25:17 Expense ratio showdown: PigWX vs. FSPSX

26:32 Closing chaos: how to contact Tom and the long-lost newsletter phone number

27:49 Origins of 800-FUND-004 and how someone just walked into the Bellevue office

29:42 End credits and final laughs—yes, even Tom held back the dad jokes (mostly)

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In this extended Friday Q&A episode, Don answers six listener-submitted questions covering a wide range of personal finance and investing topics. He kicks off with a fiery takedown of cryptocurrency as a viable asset class, arguing it’s based on hype and the greater fool theory. Other questions explore whether pensions should count as fixed income in asset allocation, the performance of Dimensional and Avantis funds versus traditional index funds, the pros and cons of Collective Investment Trusts in 401(k)s, and the strategic timing of Social Security. He ends by clarifying a common misconception about RMDs and Secure Act 2.0. Expect smart insights, a little snark, and the kind of blunt honesty that’s rare in financial media.

0:04 Listener Q&A returns with an extra dose—six questions this time

1:07 Confusing podcast scheduling clarified (sort of)

2:11 Crypto as an asset class? Don calls it “entirely invented” and dismantles the use case hype

4:32 If civilization collapses, your Bitcoin won’t save you

6:06 Crypto = greater fool theory; Don braces for hate mail

7:30 Dimensional/Avantis vs. index funds—do the extra fees pay off?

9:13 A 15-year comparison: Dimensional Global Equity vs. VT

11:43 Should a pension count as fixed income? Don says no—it’s a volatility game, not income

15:48 CITs (Collective Investment Trusts) in 401(k)s—cheaper, but less transparent

18:58 Index funds should be your benchmark; Don suspects this one’s active

20:02 Claiming Social Security early to preserve Roth? Don says the math rarely supports it

23:59 Secure 2.0 and RMD confusion—born in 1959? You still take RMDs at 73, not 75

26:15 Tech keeps improving—Don urges retirees to stay sharp, stay curious

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Don and Tom dive into a new Morningstar report showing that tactical allocation funds—those run by “smart” managers who actively shift investments—significantly underperformed simple buy-and-hold index portfolios. They unpack why doing nothing often wins, discuss investor behavior gaps, and revisit the power of staying the course. Listener questions follow on mortgage payoffs, TIAA advisory fees, and adjusting stock/bond splits in retirement. The episode wraps with Don revealing his personal creative project—his short story A Chance of Death on his LitReading podcast—and a teaser for his next story, Murder of Crows.

0:23 Morningstar headline: tactical allocation funds lose to “do-nothing” portfolios

1:45 What tactical allocation funds really are (a.k.a. expensive market timing)

2:52 Morningstar urges investors to “stay the course”

3:04 Revisiting “Mind the Gap” and why investors underperform their own funds

4:28 Data comparison: $10k in tactical vs. passive portfolio over 10 years

5:31 Why professionals can’t beat buy-and-hold investors

6:51 Human behavior, arrogance, and the illusion of market-timing skill

8:37 The need for a written plan and risk-based portfolio

9:58 If you have a plan, market noise stops mattering

10:22 Tangent: WWII documentaries vs. Taylor Swift’s Miss Americana

11:21 Listener question #1 – Paying off a low-rate mortgage vs. investing

13:35 Math and emotion collide: cheap money, liquidity, and peace of mind

15:35 Listener question #2 – TIAA Wealth Management fees and fiduciary standards

18:31 Reading TIAA’s ADV: possible fees up to 2% on small accounts

20:08 Comparing local RIAs vs. large institutions

21:08 Clarifying blended fees and fund costs

21:47 Listener question #3 – Vanguard advisor suggesting 60/40 allocation

22:53 Risk tolerance vs. risk need – the real balance

24:05 Investment Policy Statements and Vanguard’s advisory limitations

25:46 Call for more listener questions and upcoming Q&A shows

26:15 Don plugs Lit Reading and his new original story “A Chance of Death”

28:24 How AI collaboration shaped the story’s creation

30:59 Discussion of his next story, “Murder of Crows”

32:17 Invitation for audience feedback on Lit Reading stories

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Don and Tom kick off this episode with a satirical bang—mocking the apocalyptic tone of a MarketWatch article about the “Fourth Turning,” a cyclical doom prophecy claiming America faces a cataclysmic reset every 80–100 years. Citing wars, depressions, and now AI, wealth taxes, and the fall of the dollar, the hosts break down the fatalistic tone, expose the fear-marketing behind it, and reassure listeners that, historically, markets have recovered—and rewarded long-term investors.

0:04 Faux alien warning: the Fourth Turning economic apocalypse is coming

1:16 Dissecting the MarketWatch article and the “Fourth Turning” theory

2:26 Peak catastrophe by 2030? AI job loss, collapsing dollar, wealth taxes

3:38 Don asks: what is this guy selling? Spoiler: $100M wealth club

6:01 $180k to join R360—clearly not for the average listener

6:33 Don’s “financial flinch reflex” PSA spoof (ad)

7:41 Tom: “We love being scared”—AI panic and deepfake video fears

9:07 Caller Sue (68): Ready to retire with $820k and SS? Don says yes

13:05 Sue’s next step: get a fiduciary checkup, maybe run Monte Carlo

14:10 Tom runs one: 50th percentile = she hits zero at 98

15:32 Flexible withdrawal rates might work better than rigid 4%

16:34 Listener voicemail: Should we switch from Roth to Traditional now?

18:16 DT’s Roth vs. traditional strategy: save taxes while you can

20:14 WSJ article on taxes and stock gains—do ETFs instead

21:25 Tax basics for investors: capital gains rates and efficiency

23:26 Mad Men nostalgia and mid-century tax rates

25:15 TV detour: Bewitched vs. I Dream of Jeannie vs. Outlander

27:10 Back to calls: Theodore asks about 403(b) options in Burlington

29:10 Don explodes: garbage annuity vendors dominate the plan

31:01 Aspire is the only halfway-decent vendor… if you avoid their advisors

33:54 Don tells how an Albuquerque teacher got Vanguard into their plan

35:44 Aspire hack: use FundSource for no-load mutual funds

36:14 Caller Steve: hold 20 stocks or sell and rebalance?

37:53 Tom: hybrid approach. Don: depends on need. Watch tax bracket

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The show kicks off with a sardonic take on turf wars between delivery drivers—yes, really—before diving into third-quarter market returns, investor behavior, and asset class performance. Don and Tom remind listeners (again) that sticking with a diversified portfolio beats timing markets or following headline noise. Listeners call in about Social Security strategies, inheritance accounts for minors, and what to do with large sums of cash in retirement. The show wraps with a smart look at ETF-to-mutual fund conversions and why the old-school fund industry is getting left in the dust.

0:11 Delivery turf wars joke and quarter-end reflections

1:40 Fears vs. reality: inflation, jobs, and trade wars

2:16 Q3 returns: U.S. stocks +8%, EM +9.6%, silver tops, cocoa flops

3:09 What you had to do to earn those returns: be invested, diversified, and ignore noise

5:13 Don scolds investors still avoiding value and international stocks

6:11 Chocolate aside, it’s been a strong year for stocks and bonds

7:42 Promo: Why guessing isn’t a retirement plan

7:51 Don recovers from a cough; Tom lists worst Q3 performers (lean hogs!)

9:13 Listener Chad argues for claiming Social Security early if you can earn 3%

11:08 Don crunches the math: break-even at age 81–82 if invested at 3%

12:57 Survivor benefits and why waiting helps your spouse

13:57 Don jokes about his wife stealing his life force and living to 112

14:54 Vaccine banter and intro to next caller

15:56 Caller Michael from Burien sells a condo, asks where to put $300k

19:07 Don and Tom suggest municipal bonds like VTEB for tax-free yield

20:20 Michael quotes a great retirement planning aphorism

20:29 Shift to ETF inflows and the downfall of mutual funds

29:13 Vanguard’s tax-free conversion model and Dimensional’s exemptive relief

30:49 What this shift means for investors with taxable accounts

31:17 Mutual funds may soon be the next buggy whips

32:22 Listener Connie asks: do you really get back Social Security withheld when working before FRA?

33:14 Tom and Don clarify: benefit adjusted later, but no “refund”

34:37 Caller Susan from Connecticut: what to do with $250k in cash

36:52 Don: You don’t need more products—you need a real financial plan

39:17 Flat-fee plans and how to find a true fiduciary

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A lively, unscripted listener Q&A episode with no set topic — just a flood of great questions. Don and Tom tackle everything from inheriting farmland to the hidden cost of medical inflation, tax-efficient short-term investments, Ameriprise conflicts of interest, fund turnover ratios, and a heartfelt tribute to the late Jonathan Clements, a true pioneer of rational investing journalism. Plenty of wit, warmth, and straight talk about money — plus a personal moment of honesty from Tom about life, loss, and gratitude.

0:04 Cold open: “A show with no topics” banter and weather humor

2:07 Angie from St. Paul: Inheriting farmland — hold or sell?

6:04 Anton from Spokane: Medflation’s impact on Social Security COLA and Medicare premiums

10:45 Jason from Tigard: SPAXX vs. SGOV — which is better for short-term cash?

13:35 Ameriprise client: Should I use an SMA or fire my advisor?

18:41 Luke from Evans, GA: ETF turnover and what it really means

23:25 Tribute to Jonathan Clements — his life, legacy, and impact on index investing

27:10 Personal reflections, audience appreciation, and gratitude from Tom

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In the longest Q&A episode yet, Don answers seven listener questions covering everything from concentrated stock windfalls and early retirement asset allocation to Roth vs. taxable contributions, the real 59½ withdrawal date, the dangers of buffered ETFs, and the reality of home affordability. He stresses the importance of security over speculation, the need for actual retirement planning, and the pitfalls of gimmicky Wall Street products, all while weaving in his trademark skepticism and humor.

0:04 Friday Q&A intro and listener surge in questions

2:18 Jackpot in two small-cap stocks at age 70—should he sell?

6:28 42-year-old with uncertain job security and $850k retirement + $518k taxable—structuring allocations for early retirement

11:28 Roth vs. taxable brokerage contributions for flexibility before 59½

15:13 Clarifying 59½ rule—date vs. year of eligibility

17:11 Buffered ETFs explained and why they’re just Wall Street gimmicks

21:53 Rule of thumb for first-time homebuyers: mortgage % of income, 15 vs. 30-year terms, and why homes aren’t great investments

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Don and Tom tackle Americans’ retirement fears, highlighting a survey where one in five say it would take “a miracle” to retire securely. They stress the importance of planning over wishful thinking, cover the risks of recency bias, taxes, and underestimating longevity, and explain why flexibility—delaying Social Security, working part-time, downsizing, or even using a reverse mortgage—may be essential. Listener questions include a 30%+ ETF return (AVDV), the new rules allowing 529 rollovers to Roth IRAs, and a deep dive into Facet Wealth versus Northwestern Mutual, with a reminder about low-cost index investing and the value of fiduciary advice.

0:04 How confident Americans are about retirement security

1:37 “It would take a miracle” vs. “You need a plan”

2:37 The value of professional reviews and planning tools

3:52 No perfect time to retire, recency bias, and government as your “partner”

5:08 Retirement timing compared to parenthood decisions

6:06 The limits of Social Security and lifestyle realities

7:18 Adapting by working longer, delaying Social Security, or reducing expenses

8:25 Cutting wants, working part-time, or considering home equity solutions

9:23 Reverse mortgages and staged retirement strategies

10:03 Purpose, social life, and health in retirement

11:25 Listener question: international ETF with a 30%+ return (AVDV up 38% YTD)

13:02 Why diversification matters for capturing those “30 percenters”

13:22 Listener question: 529 rollovers to Roth IRAs and beneficiary changes

16:21 Listener case study: RN nearing retirement, Facet vs. Northwestern Mutual

18:07 Facet’s flat annual fee structure compared to traditional AUM fees

20:54 The pitfalls of Northwestern Mutual’s high fees and insurance roots

23:34 When to hire a fiduciary and why $1.5M+ means it’s time

25:30 Advisor costs vs. DIY investing, plus an extended “haircut analogy”

27:13 Shout-out to AI-generated Talking Real Money show art

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