Episodes

  • Friday, Again?

    Friday, Again?
    Oct 10 2025
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    31 mins
  • Nothing Wins

    Nothing Wins
    Oct 9 2025
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    36 mins
  • Fourth Turning?

    Fourth Turning?
    Oct 8 2025
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    45 mins
  • Another Quarter Done

    Another Quarter Done
    Oct 7 2025
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    45 mins
  • Just Questions (and Answers)

    Just Questions (and Answers)
    Oct 6 2025
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    32 mins
  • Copious Questions

    Copious Questions
    Oct 3 2025
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    30 mins
  • A Miracle Plan

    A Miracle Plan
    Oct 2 2025
    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 Learn more about your ad choices. Visit megaphone.fm/adchoices
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    31 mins
  • Behavior Prompting

    Behavior Prompting
    Oct 1 2025
    Don and Tom tackle the creeping role of AI in financial advice—highlighting Vanguard’s new “nudges” on its platform—before pivoting into lively listener calls. The show explores the balance between saving and living (including an $800K earner debating a bigger house), the risks of high-yield gimmick ETFs like QQQI, the simplicity of age-based 529 plans, and the murky rules around paying kids into Roth IRAs. Humor, skepticism, and practical guidance keep the conversation grounded, with a side of leaf blowers, Italian villas, and Tom’s inevitable puns. 0:10 Don’s dramatic AI apocalypse intro and Vanguard “nudges” 1:20 Squarespace rant: how customer service died 4:13 Vanguard limiting fund lists—bias toward active funds? 6:22 AI is coming for investing advice 6:35 Listener call: $800K household, cheap mortgage, “living life” vs upgrading home 10:22 House affordability rules: 25–30% PITI, low-rate lock-in dilemma 12:19 Call from Jim in Bellevue: QQQI high-yield ETF 13:44 Why covered call income funds are risky, volatile, and gimmicky 17:41 Tech focus, March 2000 parallels, why diversification beats chasing yield 19:29 Covered call strategies—why they lose upside and add complexity 22:50 Listener email from Shauna: which Utah 529 portfolio to pick 24:36 Best choice = age-based glide path, simplicity and cost advantages 26:13 Follow-up caller: Roth IRAs for kids, risk of inflated wages and IRS scrutiny 29:24 Who checks wages? IRS shutdown jokes, K-1 confusions, AI tax analysis fail Learn more about your ad choices. Visit megaphone.fm/adchoices
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    37 mins