Talking Real Money

This Friday Q&A covers real-world money decisions with real consequences, including how to invest life-insurance proceeds after a spouse's death, why dividend-and-leverage strategies promoted online are fundamentally dangerous, and how inherited IRA rules actually work under the IRS's 10-year framework. Don also tackles long-term HSA investing, explains why the 4% rule isn't a one-size-fits-all solution (especially when advisor fees are involved), and even demonstrates an AI-generated version of himself to explore whether good advice can outlive the human delivering it. Equal parts practical guidance, hard math, and skeptical humor. 0:04 Friday Q&A returns, holiday illness, and how to submit questions 1:04 Investing life-insurance proceeds after a spouse's death 1:45 Why portfolio allocation depends on income need, taxes, and risk tolerance 3:05 Why a fee-only fiduciary is essential for survivor planning 3:49 Living off dividends using leverage and margin 5:03 Why “paycheck into brokerage + leverage” strategies are dangerous 7:43 Dividend cuts, margin risk, and downturn math reality 9:29 Inherited IRA rules when the original owner had begun RMDs 11:32 The 10-year rule, annual RMDs, and IRS life-expectancy tables 12:48 Listener appreciation and the value of taking money seriously 14:01 How to invest an HSA that won't be used for years 15:09 Adjusting the 4% rule when paying an advisor 15:54 AI voice demo, advisor value, and Vanguard's Advisor Alpha Learn more about your ad choices. Visit megaphone.fm/adchoices

Retirement income doesn't have to mean hoarding assets or obsessing over leaving an inheritance. In this episode of Talking Real Money, Don and Tom dig into a topic that still makes many investors flinch: reverse mortgages. Using recent research and real-world planning logic, they walk through why modern reverse mortgages aren't the shady last-ditch option they once were, how they can reduce cash-flow stress, and when they may (or may not) make sense as part of a broader retirement plan. Along the way, they tackle myths about heirs losing the house, unpack the true costs, and explain why being “house rich and cash poor” is a real planning problem. The show also answers listener questions on bond ladders using iShares iBonds ETFs, critiques Vanguard's newer fixed-income ETF BNDF, and closes with a reminder that yield chasing — even from respected firms — still carries risk. 0:04 Retirement isn't about dying rich — it's about spending your money on you 0:25 Why inheritance shouldn't be the primary goal (with one important exception) 1:21 Shirt colors, corporate culture, and the last people still wearing white dress shirts 2:48 Smoking everywhere: airplanes, hospitals, grocery stores — and why it mattered financially 4:12 Disney jokes, expensive vacations, and setting the tone 5:08 Introducing the real topic: reverse mortgages 5:15 Why reverse mortgages still scare people — and why that reputation exists 6:44 How FHA regulation changed the reverse-mortgage landscape 7:21 Are reverse mortgages really a “last resort”? 8:14 Using home equity to improve lifestyle, not just survive retirement 8:52 Are reverse mortgages expensive? Breaking down the real costs 10:53 Lending limits, age factors, and how much equity you can actually access 12:39 When the upfront costs make sense — and when they don't 14:35 Myth busted: heirs can still inherit the home 15:08 You still own your house — it's just a mortgage with no monthly payment 16:18 Reverse mortgages as liquidity, not a wealth-building tool 16:33 The importance of planning before touching home equity 16:45 $35 trillion locked in U.S. home equity — and why paying off mortgages isn't always smart 17:57 Downsizing versus staying put: another option entirely 19:59 Listener question: simplifying a complex bond ladder 21:17 Using iShares iBonds ETFs to build a disciplined bond ladder 22:32 The risk of breaking the ladder when rates change 23:41 Listener question: Vanguard's BNDF ETF 24:44 Why chasing yield in bond funds can backfire 26:06 Gimmicks, relevance, and Vanguard's shift away from leadership 26:33 RetireMeet 2026 preview and registration details Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode dismantles the myth of “one-size-fits-all retirement,” arguing that retirement isn't a date, an age, or a lifestyle—it's a personal transition that demands both an income plan and a purpose plan. Don and Tom explore the growing trend of “un-retiring,” why fear and economic anxiety are lousy motivators for going back to work, and how a lack of planning fuels unnecessary worry later in life. Listener questions cover smart uses of 529-to-Roth conversions, parking large sums of cash, Roth strategies for young investors, rebuilding emergency funds without sabotaging retirement, and why converting Vanguard mutual funds to ETFs in taxable accounts is often a no-brainer. The through-line is clear: stop predicting the future, stop reacting emotionally, and build flexible plans that let your money support the life you actually want. 0:04 Retirement isn't a script, a date, or a finish line 0:56 The myth of “retire at 65 and stop living” 1:20 The rise of “un-retiring” and why Disney hires retirees 3:22 Fear-based reasons people go back to work 4:28 Why retirees often worry more, not less 5:10 Studies showing how many retirees expect to work again 6:38 Income plans vs. purpose plans in retirement 7:16 The Dalai Lama, retirement, and dark humor 8:16 Using leftover 529 money for a future Roth IRA 10:31 Anton Chekhov's The Bet and money as a moral test 12:08 Parking $3.5M: T-bills vs. high-yield savings 14:30 Why holding massive cash piles is usually a mistake 16:21 Interest-rate predictions and the illusion of certainty 19:17 How (and where) people actually listen to podcasts 21:02 Mortgage rates under 6% and why context matters 23:15 Roth IRAs for young investors and compounding reality 25:12 VT vs. AVGE vs. AVGV for long-term simplicity 27:51 Disney's $60B expansion and what it says about costs 31:07 Rebuilding emergency funds without derailing retirement 33:32 Converting Vanguard mutual funds to ETFs in taxable accounts 35:20 Why small tax efficiencies matter over decades Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom Cock and Don McDonald kick off 2026 with a sharp, skeptical look at portfolio simplicity—what it really means, what it doesn't, and why promises like “no sacrifice in returns” should always raise an eyebrow. Using a Morningstar article as a springboard, they dig into active vs. index funds, one-fund and target-date strategies, and the behavioral traps that complexity creates. Listener calls drive deeper discussions around Avantis funds (AVGE vs. AVGV), value tilts, international exposure, Fidelity's zero-fee funds, and when simplicity actually beats sophistication. Along the way: holiday viruses, Jeopardy ETF fails, Tesla-as-a-value-stock arguments (sort of), and a reminder that knowing yourself as an investor matters more than chasing the “perfect” allocation. 0:04 Holiday hangover, fake presence, and welcoming 2026 1:27 Simplicity in investing and why complexity isn't intelligence 1:44 Morningstar's “simplify your portfolio” claim—skepticism engaged 3:01 Active funds vs. index funds (and Morningstar's awkward contradiction) 3:56 One-fund vs. multi-fund portfolios and why rebalancing is hard 5:24 Target-date funds as delegation for real humans 7:32 Hodgepodge-itis vs. fewer funds, fewer mistakes 8:52 Listener call: Roth IRA for an 8-year-old and AVGE vs. AVGV 12:20 Value tilt, international exposure, and long time horizons 13:44 AVGE vs. AVGV performance—why short-term results don't settle debates 16:57 VT compared to Avantis—diversification without tilts 17:32 Fidelity Zero funds—what's free and what's the catch 20:00 Jason from Sammamish: value, growth, Tesla, and confidence 23:36 SPY vs. SPYM and when cheap is just cheap 25:46 Listener call: escaping a Fidelity managed large-cap portfolio 29:58 What to say when an advisor tries to keep your money 31:24 Jeopardy contestants miss “ETF” (yes, really) 33:46 AVGE vs. VT—tilts, belief systems, and picking your poison Learn more about your ad choices. Visit megaphone.fm/adchoices

Predictions feel comforting—but they're usually nonsense. In this episode, Don and Tom dismantle the illusion of foresight by revisiting last year's loudest economic forecasts around tariffs, inflation, jobs, recessions, and markets. Drawing from a Wall Street Journal retrospective, they show how both political promises and expert predictions missed the mark, with reality landing squarely in the messy middle. The takeaway is classic Talking Real Money: nobody—not economists, not presidents, not pundits, and especially not you—has actionable insight into the future. That's why successful investing isn't about forecasts or hot takes, but about building a diversified portfolio, rebalancing when needed, and tuning out the noise. The episode wraps with listener questions on teen investing accounts and Roth conversion rules, plus a reminder that humility beats hubris every time markets get unpredictable. 0:04 The future is unpredictable—even when we pretend it isn't 0:26 Why we crave predictions and mistake luck for skill 0:53 Being “right” once doesn't mean anything 1:58 Tariffs, Trump, and the great forecasting divide 2:27 Inflation predictions that never showed up 3:53 Jobs, unemployment, and why both sides were wrong 5:49 Who actually paid for tariffs (hint: not who you think) 7:08 Recession fears vs. reality—and the AI wildcard 8:55 Why short-term predictions fail and macro trends survive 10:41 The truth usually lives between the extremes 11:31 Lao Tzu, Yogi Berra, and why nobody knows the future 13:20 The most dangerous “expert” investors trust: themselves 14:43 Listener question: investing for a 16-year-old 17:29 Roth IRA vs. UTMA/UGMA and simple fund choices 18:06 Listener question: Roth conversions and the five-year rule 20:54 Humor, offense, and why everyone needs to lighten up 21:14 RetireMeet 2026 details and special guest preview 23:14 Apella Wealth philosophy and free help reminder 24:39 The number one word of the year (still shocking) Learn more about your ad choices. Visit megaphone.fm/adchoices

Investing isn't a game, and treating it like one can quietly sabotage your future. This episode dismantles the idea of “trying out” investments or advisors the way Wall Street has trained people to do for decades. Don and Tom argue that real financial advice starts with planning, not products, and that a true fiduciary focuses on taxes, portfolio design, and long-term goals — not beating markets or selling what's hot. Listener questions tackle portfolio overlap inside a 401(k), when simplicity beats customization, the reality behind so-called “Trump accounts” for children, and how to evaluate companies like Corbridge Financial in teacher retirement plans. The show wraps with a reality check on World Cup ticket pricing that somehow makes active management look affordable by comparison. 0:04 Why “trying out” investments makes no more sense than test-driving surgery 1:26 The danger of treating investing like a game 2:29 How Wall Street gamified investing for nearly a century 3:45 What good advisors don't promise 4:10 Fiduciary planning versus transactional sales 5:14 Marketing narratives vs. real financial planning 6:55 Why big advisory firms spend fortunes on persuasion 7:48 Hot returns, sexy funds, and why chasing them fails 8:35 Investing to win vs. investing to reach a goal 9:56 Accepting market reality instead of competing with billionaires 11:27 Product versus planning — the core distinction 12:09 Listener question: fixing portfolio overlap inside a 401(k) 14:34 Why simpler portfolios usually work better 15:09 Using target-date funds to eliminate overlap and rebalancing headaches 16:19 What “Trump accounts” actually are — and what they aren't 18:39 Comparing Trump accounts to 529 plans 21:38 Corbridge Financial: when it's fine and when it's a trap 23:01 Appreciating listeners everywhere (yes, even Portland) 24:40 World Cup ticket prices that defy financial gravity Learn more about your ad choices. Visit megaphone.fm/adchoices

0:04 Remembering the “good old days” of fat commissions 0:33 From $200 trades to zero commissions—what really changed 1:18 Free trading everywhere… so how do brokers make money now? 2:37 Robinhood's explosive growth and the rise of trading culture 3:15 Trading volume triples in six years—what that signals 4:42 Payment for order flow, cash sweeps, and hidden costs 6:21 Are investors actually getting a deal from free trading? 7:13 Why frequent trading and poor returns go hand in hand 8:21 Dopamine, gambling mechanics, and Robinhood's design problem 9:47 Day trading: the comeback nobody needed 10:57 Why most day traders lose—and taxes make it worse 11:36 Prediction markets: gambling with an investing label 13:16 Listener questions begin 15:55 What is a tokenized stock—and why it's not investing 17:25 Bucket shops, NFTs, and synthetic “stocks” 18:45 Early retirement withdrawals and the Rule of 55 19:33 Default retirement plans stuffed with annuities—good idea? 21:20 Liquidity risk and why annuities aren't one-size-fits-all 22:26 Vanguard's new Core Plus Bond ETF (BNDP) 24:13 Chasing yield vs. using bonds for stability 26:20 Why bonds shouldn't be your return engine 27:36 Hoping for a calmer 2026 (good luck with that) Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode opens with a reality check on streaming delays before diving into the growing divide between investing and gambling, highlighted by Charles Schwab's refusal to promote crypto, options, and prediction markets while Robinhood leans fully into high-intensity trading. Don and Tom warn that flashy features and frequent trading usually lead to worse outcomes, not better ones. Listener questions cover whether employees can roll a 401(k) during a plan change (usually no), how to cope with bad retirement plans, and how to choose between a high-cost growth fund and a low-cost index option. The show also tackles whether mixing Avantis and Dimensional funds truly adds diversification, argues that over-engineering portfolios is counterproductive, and closes with a candid discussion about the decline of financial radio, the rise of podcasts, and why a strong financial plan matters more than recent market gains. 0:04 Recorded-not-live reality, streaming delays, and why nothing feels real anymore 1:56 Schwab draws a hard line between investing and gambling 2:56 Robinhood's casino-style features and the problem with pandering 6:12 Why trading more usually means ending up with less 6:52 Listener question: Can you roll a 401(k) during a plan change while still employed? 9:23 Why “in-service” rollovers usually aren't allowed before 59½ 11:53 What employees can do when stuck in a bad 401(k) plan 14:44 Fund choice question: Fidelity Growth vs. Vanguard 500 Index Trust 18:06 Why expenses, risk, and diversification matter more than past performance 19:21 Why podcasts are replacing traditional financial radio 22:06 How to listen to podcasts using Apple Podcasts and Spotify 27:22 Avantis vs. Dimensional: does doubling up add diversification? 31:52 Over-diversifying and the illusion of control 34:42 New-year reminder: returns don't equal good planning 35:25 The importance of having an actual financial plan Learn more about your ad choices. Visit megaphone.fm/adchoices

With Tom on vacation and an eerily convincing AI stand-in holding down the mic, Don kicks off 2026 by tackling one of the most persistent listener questions: how to actually find a true fiduciary—and how to eliminate salespeople fast. Using FINRA's BrokerCheck as a simple filter, the show explains why the “B” matters, why dual-registered advisors are still a risk, and how complexity is often a red flag. From there, the conversation dives into the rise of RILAs (registered index-linked annuities), why their shiny back-tested returns don't mean much, and how simpler balanced portfolios often do better with far less risk and confusion. Along the way, the hosts cover podcast reviews, investing in bourbon barrels (don't), Roth IRAs for teenagers (do), and close with Tom's five timeless investing rules for 2026: go global, simplify, define risk, rebalance, and understand your taxes. 0:04 New year, Tom on vacation, and the rise of AI Tom 0:22 AI voices, joke quality, and job security jokes 2:20 Welcome and the show's core mission 2:46 How to actually find a real fiduciary 3:30 BrokerCheck explained and why the “B” is a deal-breaker 5:24 Firm searches and fast advisor elimination 6:38 Why dual registration still isn't fiduciary 7:22 RILAs introduced and why “index-linked” is a warning sign 9:38 Hypothetical returns and misleading back-testing 11:19 Balanced index funds vs annuity complexity 13:00 Why RILAs solve no real investor problem 14:08 How to leave podcast reviews (and where) 15:22 Apple vs Spotify reviews and ratings reality 17:34 Ratings, trolls, and thin-skinned hosts 20:07 Tom's five investing rules for 2026 20:41 Go global—actually global 21:56 Fewer accounts, less mess 22:49 Know your risk before the market teaches you 23:50 Rebalancing after strong stock years 24:38 Understanding taxes by account type 27:33 Bourbon barrel investing pitch—hard pass 29:13 Custody risk and private-investment danger 31:35 No sales guests, ever 33:54 Roth IRAs for working teens 34:35 RetireMeet 2026 announcement Learn more about your ad choices. Visit megaphone.fm/adchoices

Wall Street is pitching “fixed-maturity ETFs” as the perfect solution for retirees who want certainty, income, and peace of mind—but are they actually solving a problem that already has simpler answers? In this episode, Don and Tom break down what bonds and CDs really do, why fixed-maturity funds are being pushed so hard right now, and how fees quietly eat away at the promised benefits. Along the way, they explain the real role of bonds in a portfolio, why chasing yield is a trap, and how diversification and simplicity still beat clever packaging. Listener questions tackle fiduciary responsibility in 401(k) plans, loaded mutual funds, and how much international exposure makes sense in retirement. 0:04 New year opener, time anxiety, and refusing to acknowledge large numbers 1:05 What a bond actually is—and what it guarantees (and doesn't) 1:54 CDs vs. bonds: fixed maturity products that already work 2:37 Why Wall Street suddenly “needs” fixed-maturity ETFs 3:22 BulletShares, yields, and the quiet problem of fund expenses 4:45 Larry Swedroe's blunt answer: skip the fund, buy the bonds 5:24 Yield fixation and how investors ignore cost and complexity 6:05 When fixed-maturity ETFs might make sense—and when they don't 7:14 I-Bonds, TreasuryDirect, and Don's practical reality check 7:48 A simple solution: total bond fund plus a CD ladder 8:28 Why fixed maturity doesn't mean fixed safety 10:09 Expense ratios compared: broad bond funds vs. sliced products 10:35 The real purpose of bonds in a portfolio 12:04 Putting 2022's bond losses in proper historical context 12:58 Eugene Fama on Wall Street “innovation” 13:20 Listener question: fiduciary responsibility in a 401(k) plan 16:30 Listener question: A-shares, B-shares, loads, and advisor honesty 19:14 Why high fund expenses hurt more than exit fees 20:52 Listener question: international exposure in retirement portfolios 22:18 Practical global diversification without precision theater 23:02 Why Don is flexible on allocations—but not on insurance sales 23:22 How to send in questions and closing banter Learn more about your ad choices. Visit megaphone.fm/adchoices

The calendar flipped, but the rules didn't. In this New Year Friday Q&A, Don tackles listener questions on longevity annuities (QLACs), legacy insurance mistakes, advice-only advisory services, and the growing trend toward complex fixed-income systems and alternative investments. From insurance math that favors the house to eye-watering fees dressed up as innovation, the message stays consistent: simplicity beats sophistication, fees matter, and global diversification works the same whether you live in Seattle or Spain. 0:00 New year, new Q&A — and why January changes nothing 1:30 QLACs explained and why the math still favors insurers 2:49 Longevity odds vs. guaranteed income myths 5:15 Trapped in a bad annuity — ride it out or cash out? 8:53 “Magic money,” bonuses, and negative real returns 10:46 Advice-only firms: Abundo Wealth and paying for simplicity 13:44 Bond ETFs vs. CD and Treasury ladder strategies 17:39 When “systematic” fixed income starts to smell like gimmicks 18:53 Alternatives, private credit, and outrageous expense ratios 22:18 Why Don defaults to simplicity — every time 24:35 Global diversification: same advice, any country 27:38 Happy New Year — and why boring still works Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode dismantles the idea that successful investing comes from finding the next hot thing. Instead, Don and Tom argue that good portfolios are built by eliminating what doesn't belong: actively managed funds, sector ETFs, alternatives, high-yield bonds, gold, and other distractions that add complexity without purpose. Drawing on a Morningstar column by Amy Arnott, they reinforce that most investing mistakes come from chasing performance rather than embracing simplicity and discipline. The show also tackles listener questions on retirement “bucket” strategies, rebalancing timing, Dimensional fund structure, and annuities—emphasizing that bonds exist for stability, cash should be limited and intentional, and any strategy must be personal, rules-based, and boring enough to actually work. 0:04 Opening banter, Apple censoring Tom's name, and the beige pudding world 1:12 Bitcoin critics, one-star reviews, and a bad 2025 for crypto 2:03 Core idea: good investing is about elimination, not prediction 2:56 Amy Arnott and the case against active management 4:07 Why past winners usually become future losers 5:28 REITs, once useful, now mostly redundant 6:01 Sector funds as performance-chasing traps 8:19 Alternatives, I Bonds, and junk bonds—complexity without payoff 10:04 Bonds explained properly: stability, not income or excitement 11:14 Gold (and Bitcoin) as non-productive speculation 13:21 Simplify first and portfolios become easier—and calmer 15:05 Retirement bucket strategy: where it helps and where it hurts 18:48 Cash as an emergency tool, not a long-term holding 21:04 MYGA annuities, safety trade-offs, and insurer risk 29:04 Insurance failures as cautionary history 31:04 DFAW explained: Core Equity 1 vs Core Equity 2 35:53 Rebalancing discipline: timing beats tinkering 39:11 Final reminder: stop watching your portfolio so much Learn more about your ad choices. Visit megaphone.fm/adchoices

As the year crawls to a close, Don and Tom torch the ritual of “New Year, New You” financial advice and take aim at the endless lists of five things you must do next year. They break down why year-end deadlines are mostly psychological theater, why prediction-based investing is a sucker's game, and how even AI—when pressed—admits the truth: diversification beats cleverness, patience beats prediction, and complexity usually hides higher costs and worse outcomes. Along the way, they tackle 529 plans, proposed “Trump accounts,” Roth strategies for kids and retirees, factor investing myths, and the ongoing media obsession with whatever already went up last year. It's a holiday episode for skeptics, cynics, and anyone tired of being told that this is finally the year everything changes. 0:04 Holiday cynicism, snow, trees plotting revenge, and Don declares war on Pollyanna finance 1:19 Year-end obsession: why December 31 is an arbitrary psychological trap 2:29 Why “five things to do in the new year” articles exist—and why they're mostly nonsense 3:55 Asking AI for financial advice and accidentally getting decent answers 4:18 Don's AI delivers brutal honesty: complexity isn't sophistication, it's camouflage 5:54 The most dangerous question of all: “What should I invest in next year?” 6:06 Everyone's favorite prediction: AI stocks (again), and why that's backward logic 6:29 The real answer: globally diversified equities, patiently held and largely ignored 8:07 Motley Fool, Morningstar, defense stocks, and the annual prediction circus 9:29 AI's final verdict: everything after diversification is garnish people argue about on TV 10:33 Listener Brian on New York 529 plans, state tax deductions, and Roth rollover flexibility 11:30 How aggressive is too aggressive for a child's college savings? 12:45 Why age-based 529 portfolios are often far more conservative than parents realize 14:10 When college money should actually shift to safety—and when it shouldn't 15:43 The mysterious “Trump accounts”: proposed rules, confusion, and missing details 16:56 Tax treatment uncertainty, Roth myths, and why free money is still free money 18:39 Clear conclusion: this account doesn't exist yet and nobody knows the real rules 20:05 Don's full rant: pandering policies, financial clutter, and unnecessary complexity 22:07 Listener Larry on starting a Roth IRA for a 19-year-old with a one-fund solution 22:47 AVGE explained: global, factor-tilted, low-cost, and boring in the best way 24:15 AVGE vs. Vanguard Total World: interest vs. necessity 25:26 AVGE underperformance criticism and why one-year returns are meaningless 28:26 Why Avantis funds aren't trying to “pick winners” and never claimed to 31:32 Listener Caroline on retirement withdrawals, IRAs, Roths, and tax reality 33:11 The unavoidable truth: you'll pay taxes—now or later 35:43 How (and where) listeners can actually rate the show 38:01 Politics, labels, John Oliver, and why nuance is apparently illegal now 38:54 Capitalism, fairness, and refusing ideological purity tests Learn more about your ad choices. Visit megaphone.fm/adchoices

In this post-Christmas edition of Talking Real Money, Don McDonald and Tom Cock dismantle one of the most seductive myths in personal finance: the promise of high returns, no risk, and tax-free income. Using the lawsuit filed by Kyle Busch against Pacific Life as a case study, they expose the dark mechanics of indexed universal life insurance—hidden commissions, opaque costs, fabricated indexes, and returns that quietly disappoint. The episode then pivots to listener questions on diversification mistakes, Roth vs. traditional 401(k)s, late-career pivots into financial advice, ETF selection for retirees, and why doing less with your portfolio almost always beats doing more. 0:04 Post-Christmas welcome, Kyle Busch jokes, and why rich people get fleeced too 1:18 Indexed Universal Life explained (and why it's not an investment) 1:45 The “bank on yourself” fantasy and why it never dies 2:27 $10.5 million in premiums and promises of $800K tax-free income 3:20 Why IULs avoid SEC and FINRA scrutiny entirely 4:21 The sixth premium notice that blew up the deal 4:41 How IULs implode if you stop paying—and why everything can vanish 5:52 “Tax-free income, high returns, no risk” exposed as marketing fiction 6:01 Hidden commissions, alleged 35% payouts, and zero disclosure 7:37 Proprietary indexes designed to benefit insurers, not investors 8:50 Internal Pacific Life doc: “Don't call yourself a financial planner” 9:57 Why consumers can't see costs, commissions, or real returns 11:37 Real-world IUL returns: roughly 3–5% annually 12:23 Why even Kyle Busch doesn't actually need life insurance 13:44 Caveat emptor—and why “Life” in the firm name should trigger alarms 14:03 Listener portfolio question: 60/15/25 isn't diversified 14:53 The S&P 500 isn't “the market” (and seven stocks prove it) 15:54 Simple global solutions vs. portfolio over-engineering 17:11 Podcast tech humor and March seminar tease 17:22 Listener praise—and teaching people how to find podcasts 18:11 2026 seminar date confirmed: March 7 19:23 Career pivot at 53: CFP vs. AFC vs. Series 65 22:02 Why fiduciary firms are hiring—and sales shops are traps 23:22 ETF selection for retirees: growth, risk, and tax efficiency 24:27 Why Morningstar confuses more than it helps 25:07 Dimensional, Avantis, and keeping portfolios simple 26:20 Final thoughts, free fiduciary consults, and year-end wrap Learn more about your ad choices. Visit megaphone.fm/adchoices

A year-end Boxing Day Q&A covering realistic downside expectations for global portfolios, the marginal value of adding international small-cap value, details for RetireMeet 2026, and a deeply skeptical look at Medicaid-compliant annuities. The common thread: diversification helps, simplicity usually wins, and when complexity shows up early, commissions are often lurking nearby. 0:04 Boxing Day confusion, goodwill, and a short-format holiday Q&A 1:07 Why this is a shorter, four-question episode to wrap the year 2:17 How much can a globally diversified stock portfolio really fall 3:06 Limits of global market data and why 2008 still sets expectations 4:11 Roughly 40% decline for global stocks in 2008 and how bonds softened the blow 4:54 Why worst-case scenarios are about expectations, not predictions 6:07 Listener portfolio with VXUS, AVUV, and SWTSX and whether to add AVDV 6:35 Balancing small-cap value exposure versus keeping things simple 7:56 Why a few basis points rarely justify added complexity 8:38 RetireMeet 2026 question and a well-earned jab at Tom's joke delivery 10:02 RetireMeet 2026 details and early seat reservations 10:29 Event date and location: March 7, Bellevue at Meydenbauer 11:44 Medicaid-compliant annuities explained through a real family scenario 13:57 Why MCAs are usually last-resort tools, not early planning solutions 15:49 Concerns about elder law attorneys, incentives, and hidden commissions 16:35 What MCAs really do: income conversion, not asset protection 17:28 Why skepticism is healthy and shopping non-commission options matters 18:43 Closing thoughts on trust, incentives, and surviving another financial year Learn more about your ad choices. Visit megaphone.fm/adchoices

It's surprisingly hard to know what something is really worth until someone actually tries to buy it—and that problem is front and center in private funds. Don and Tom unpack why private equity, private real estate, and other “alternative” investments often look calm and stable on paper, only to suffer brutal price drops once they finally trade in public markets. From a Wall Street Journal example of a private real estate fund losing roughly 40% overnight, to Morningstar's troubling enthusiasm for expensive, speculative new ETFs, the episode reinforces a core principle: prices discovered by real markets beat internal estimates every time. Along the way, listeners call in with real-world retirement questions, inherited IRA rules, portfolio simplification strategies, and a healthy dose of holiday banter. 0:04 What something is “worth” versus what someone will actually pay 1:06 Defining private funds and why valuation is murky 2:27 Private fund pricing versus real market pricing 3:56 BlueRock fund haircut: paper value meets reality 4:24 Market pricing, efficiency, and the wisdom of crowds 5:42 The myth of private investments being “less volatile” 6:27 Real estate as the perfect valuation example 7:39 Listener call: inherited IRA and annuity distribution rules 12:42 Holiday humor, crypto annuity joke, and Kentucky bourbon 16:01 Moving assets from Edward Jones, loads, and simplification 19:41 DIY portfolios versus advisor value 21:08 Morningstar's “Best and Worst New ETFs” critique 22:21 Why most new ETFs exist (and why you don't need them) 24:43 Shockingly high ETF expense ratios 26:27 Leveraged crypto ETFs and financial absurdity 27:37 Seasonal podcast plug and ratings gripe 28:44 Listener call: Boeing retirement and rollover planning 34:40 Holiday reflections, gratitude, and comfort over riches Learn more about your ad choices. Visit megaphone.fm/adchoices

A Wall Street Journal column argues that younger investors are turning to options, crypto, and betting as a rational response to a “rigged” economic system. Don and Tom aren't buying it. While acknowledging real headwinds—student debt, housing costs, wage gaps—they dismantle the idea that gambling is an intelligent adaptation. Drawing on history, lived experience, and actual math, they make the case that leverage, speed, and desperation reliably destroy wealth, while patience, diversification, and boring consistency still work. The system may be flawed, but trying to beat it with casino tactics only helps the house. 0:04 Opening rant on “financial nihilism,” generational scolding, and why Gen Z investing looks like gambling 1:21 Wall Street Journal column by Kyla Scanlon introduced and framed 2:53 Gambling vs. investing—why “the system is rigged” is a terrible excuse for riskier behavior 5:24 Don and Tom reflect on their own slow, uncomfortable paths to financial stability 6:04 Real-world counterexample: young coworkers who are saving, investing, and buying homes 7:41 Defining “financial nihilism” and why speed, leverage, and impatience backfire 9:00 What actually works: spend less, delay gratification, diversify, avoid leverage 10:46 Historical perspective—every generation faced headwinds, none solved them by gambling 12:39 The power of compounding, patience, and boring index investing 14:41 Critique of the “small chance of huge return beats slow decline” argument 17:12 Listener question: cap-weighted vs. equal-weighted index funds explained 19:11 Why equal weighting tilts toward value and smaller companies—and costs more 20:22 Millennial caller Jason offers empathy for generational frustration without endorsing gambling 23:48 Lifestyle expectations, flexibility, and why hardship doesn't justify reckless investing 27:27 Food, lifestyle, and historical context—what's better now, what isn't 29:25 Hormel vs. Motorola story revisited: why predicting winners is nearly impossible 36:29 Jaw-dropping returns: Hormel's long-term outperformance over flashy tech 38:45 Light holiday banter, gift absurdities, and wrapping up the show Learn more about your ad choices. Visit megaphone.fm/adchoices

Streaming was supposed to save us money. Instead, it quietly rebuilt cable… with better branding and worse self-control. Don and Tom trace the journey from rabbit-ear TV to today's subscription sprawl, where “it's only $14 a month” quietly becomes hundreds per year. They break down why streaming costs have exploded faster than inflation, how duplication and inertia drain wallets, and what actually works to fix it (bundling, pruning, and strategic binge-and-cancel). From there, the show pivots to listener questions covering smart investing for an 18-year-old, retirement withdrawal sequencing, trust and estate planning pitfalls, and why complexity is often the real enemy of good financial decisions. 0:04 Life before streaming: rabbit ears, three channels, and forced family labor 0:48 Rewatching Bewitched and realizing old TV was… not great 2:27 Cable's rise, early streaming optimism, and Netflix's cheap beginnings 3:30 Subscription creep: listing the modern streaming pileup 4:16 Streaming prices vs inflation — why this hurts more than groceries 6:43 Average household streaming costs and the real percentage increase 8:21 Duplicate subscriptions and why households overpay without realizing it 9:37 Live TV bundles, YouTube TV vs Hulu, and paying cable prices again 12:30 Binge-and-cancel as a legitimate cost-control strategy 14:02 Value judgments: paying for services you don't actually watch 15:20 Annual audits, forgotten subscriptions, and silent monthly leaks 18:17 Investing $9,000 for an 18-year-old with decades ahead 19:20 Why a Roth IRA plus one global ETF can be enough 20:53 Retirement withdrawals: taxable vs IRA confusion clarified 22:45 When wealth gets big enough that DIY stops making sense 24:00 Trusts, trustees, and why professional oversight is expensive 27:15 Estate planning as a team sport (advisor + attorney) 29:33 Why every TV character is suddenly a podcaster 30:49 Gratitude, rankings, and why the audience matters Learn more about your ad choices. Visit megaphone.fm/adchoices

In this holiday Friday Q&A, Don opens with a festive announcement about Season's Readings—now Apple-featured and temporarily commercial-free—before diving into listener questions on fixed annuities versus CDs, a creative (and complex) 529-to-Roth strategy tied to Georgia tax deductions, simplifying IRA management and RMDs at Schwab or Vanguard, the unavoidable tax traps of old investment clubs structured as partnerships, and the perennial question of how much U.S. large-cap exposure belongs in a diversified equity portfolio. Along the way, Don reinforces core themes: simplicity beats complexity, costs matter, taxes are inevitable, and diversification has no single “correct” allocation—only trade-offs aligned with philosophy and discipline. 0:04 Holiday welcome, Friday Q&A format, and how to submit questions 0:46 Season's Readings podcast announcement, Apple feature, and commercial-free holiday run 2:16 Fixed annuities vs CDs: safety, state guarantees, and annuity ladders 5:29 Using 529 plans as a long-term Roth pipeline with state tax deductions (Georgia example) 9:29 Moving an IRA to Schwab or Vanguard and automating RMDs 10:20 Investment clubs as partnerships: K-1s, capital gains, and tax inevitability 14:47 How much U.S. large-cap belongs in a diversified stock portfolio 18:54 Reviews, critics, Bitcoin pushback, and holiday sign-off Learn more about your ad choices. Visit megaphone.fm/adchoices

Market drops are a gift when you're young and a potential gut-punch when you're retired, and this episode walks through why that's true—and what to do about it. Don and Tom break down sequence-of-returns risk in plain English, then explore practical defenses: cash buffers, CD ladders, bucket strategies, flexible withdrawals, partial retirement, and why stocks still belong in retirement portfolios whether you like it or not. Listener questions tackle letting portfolios ride for heirs, value vs. total small-cap funds, tax consequences of rebalancing, and whether political risk should affect public fund investing. The takeaway: there's no perfect plan, only resilient ones—and behavior matters more than spreadsheets. 0:04 Why market drops are good for young investors and scary for retirees 0:28 Holiday cheer, audience growth pleas, and the gospel of paper questions 1:40 Why young investors should root for down markets 2:41 Sequence-of-returns risk explained without the jargon 3:20 Real-world retire-at-the-wrong-time examples (2000, 2008, 2020, 2022) 4:48 Why sequence risk is such a big retirement planning problem 5:40 What to do if you fear bad markets near retirement 6:08 Cash buffers and why they actually make sense in retirement 7:06 Bucket strategies and how they're supposed to work 7:36 CD ladders as a “get-me-through-the-bad-times” strategy 9:27 Flexible withdrawal strategies and lifestyle adjustments 10:37 Partial retirement, side hustles, and easing into retirement 11:33 Why retirees still need stock exposure 12:26 Even small equity allocations help fight inflation 13:20 There is no perfect withdrawal rate—only survivable ones 14:11 The realistic withdrawal range and why stocks are still required 15:33 Why professional fiduciary reviews actually matter 16:21 When life blows up your retirement plan anyway 18:55 Listener question: should a retiree just let stocks ride for heirs? 21:36 Washington CARES, politics, and investing public funds 23:18 Small-cap value vs. small-cap index: FSIVX vs. FSSNX 25:44 Why low-cost value tilts can still make sense 27:00 Smarter gifts: Roth IRAs, 529s, and future-you generosity Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode of Talking Real Money takes aim at the latest “easy money” illusion—house flipping—explaining why rising costs, higher interest rates, softer housing demand, and plain old competition have drained much of its appeal. Tom and Don connect flipping's decline to a familiar pattern of speculative behavior, much like day trading or past real estate manias, and reinforce why there are no reliable shortcuts to wealth. Listener calls drive a wide-ranging discussion on global diversification versus U.S.-only investing, the dangers of concentration risk in the S&P 500, how recency bias distorts performance comparisons, and why owning more markets matters more than making predictions. The episode wraps with practical retirement guidance for older investors, including simplifying portfolios with low-cost target-date funds, and closes with trademark humor and perspective. 0:05 Show open, intro banter, singing callbacks, and weekend rhythm 0:28 House flipping compared to day trading and FOMO investing 1:28 Why flipping activity is down sharply: costs, rates, and competition 3:41 The myth of “passive income” in real estate 4:50 Softer housing markets and demographic headwinds 6:02 No magic systems—long-term investing still wins 8:27 Lisa (Colorado): investing nonprofit funds at Vanguard 10:30 VOO vs VTI vs VT and the case for global diversification 12:29 Volatility, standard deviation, and diversification basics 14:44 Sharpe ratios, recency bias, and misleading performance metrics 16:54 Charles (Seattle): Boeing plans, VOO, and AVGE at Schwab 18:32 S&P 500 concentration risk and the “Magnificent Seven” 21:33 Jason (Sammamish): VTI vs VT debate and long-term market data 28:41 Debbie (Camano Island): portfolio risk concerns at age 73 31:20 Risk tolerance vs risk capacity in retirement 33:16 Vanguard target-date funds as a simple retirement solution 36:01 Lighter close with creative fundraising and holiday humor Learn more about your ad choices. Visit megaphone.fm/adchoices

A classic TRM episode that starts with Tom's ill-fated attempt to cross a flooded Snoqualmie River (spoiler: no walking on water) and turns into a timely lesson on market returns, diversification, and why comparing your portfolio to headline numbers is usually a mistake. Don and Tom unpack eye-popping 2025 performance across U.S., international, bonds, and small-cap value, warn against recency bias and overpriced active funds, and take several listener calls on Roth conversions, bad custodians, debt forgiveness taxes, and rollover mechanics. The show wraps with Don's well-earned victory lap for Seasons Readings, now rubbing shoulders with Julie Andrews and Hugh Bonneville in Apple's fiction charts. 0:04 Tom gets stranded by flooding after a questionable river-crossing idea 1:40 Flood damage reality check and sympathy for displaced homeowners 2:22 Market year-end context and “Dave Ramsey average” returns 3:32 Bond funds surprise with strong year-to-date performance 4:05 International and global funds crush expectations 5:46 Why your return may lag headlines: allocation, costs, and recency bias 6:20 Apples-to-apples portfolio comparisons matter 9:26 Active funds underperforming despite a strong market year 10:47 Global diversification pays off big in 2025 12:04 January prerecorded show tease and holiday logistics 13:25 Seasons Readings featured by Apple Podcasts—downloads explode 15:18 Fiction chart brag: sandwiched between Julie Andrews and Hugh Bonneville 16:25 Listener call: John Hancock IRA, forced conversions, and bad advice 19:06 Why liquidating inside an IRA is not a taxable event 20:17 Exposing high-cost, loaded funds and custodian nonsense 23:35 Listener question: Roth conversions, pensions, and IRMAA timing 26:36 Why “top tax bracket forever” is usually a myth 27:31 Listener call: debt settlement and taxable forgiveness income 30:13 When a 1099-C is a good deal anyway 31:56 Flood-era investment scams and terrible ideas 35:55 Clarifying direct rollovers vs. taking possession of funds 38:13 Roth IRAs for young earners—yes, even pizza money Learn more about your ad choices. Visit megaphone.fm/adchoices

If you're nearing retirement and uneasy about the math, you're not alone. Don and Tom tackle the uncomfortable reality that most near-retirees haven't actually run the numbers—and many won't like what they see when they do. Drawing on Vanguard data and real-world client experience, they break down three practical ways to shrink a retirement gap: working longer (but not necessarily full-time), thoughtfully tapping home equity, and spending less before and during retirement. 0:06 Opening and the retirement gap problem 0:52 Podcast platforms, Apple vs Spotify, and Don's short-story empire 4:08 How TRM ranks among investing podcasts and why that still feels surreal 5:24 Vanguard data: only 40% of near-retirees are on track 6:51 Kids, money, and why retirement math gets uncomfortable fast 7:51 Strategy #1: Working longer (and why part-time can be powerful) 9:41 Purpose, boredom, and the underrated psychology of retirement 10:00 Strategy #2: Home equity as a retirement resource 11:12 Downsizing, renting, HELOCs, and reverse mortgage trade-offs 13:05 Strategy #3: Spending less—before and during retirement 14:29 Reverse mortgage costs, limits, and real-world implications 17:01 Social Security timing and when immediate annuities actually help 18:40 Inflation risk, fixed income streams, and practical trade-offs 19:02 Listener Q: AVGE vs DFAW and understanding underlying holdings 21:48 Listener Q: Aggressive Roth portfolios intended for heirs 25:30 Listener Q: Washington 529 plans and GET vs traditional 529s 27:32 Listener Q: Quantum computing (short answer: no) 28:59 Sector investing, AI hype, and why diversification wins Learn more about your ad choices. Visit megaphone.fm/adchoices

A holiday-flavored Friday Q&A that covers a lot of ground without selling a single candy cane. Don answers listener questions on Medicare vs. Medicare Advantage (and the IRMAA buzzsaw), how to safely reposition an elderly parent's taxable account, whether to ditch target-date funds for a DIY equity portfolio, how to think about international small-cap ETFs, why teaching kids to pick stocks is a terrible idea, and what to expect when a “free portfolio review” comes from a company whose name literally includes the word annuity. Skeptical, practical, and very on-brand. 0:17 Corny holiday Q&A musical intro and setup 0:33 Friday Q&A format, how questions get on the show, and holiday vibe 2:00 Medicare vs. Medicare Advantage, IRMAA penalties, and why private insurers are exhausting 3:37 Why capital gains can make Medicare shockingly expensive 4:15 The profit motive problem with Medicare Advantage plans 4:37 Question transition and listener call-in reminder 5:43 Managing an 82-year-old's taxable account: safety vs. yield 6:18 Why bond funds like BND diversify interest-rate risk better than savings accounts 7:15 CD ladders: how they work and why discipline matters 7:39 Treasury funds vs. total bond funds for capital preservation 7:47 Closing thoughts on preservation-focused portfolios 8:52 Target-date funds vs. DIY 401(k) portfolios 9:20 Glide paths, rebalancing, and what target-date funds do well 10:35 100% equity risk, volatility, and why down markets help accumulators 10:53 Choosing between AVDV and AVES (international small value vs. emerging markets) 11:47 Why the correct answer is often “both” 12:33 Teaching high school students about investing 13:52 Why stock-picking education reinforces a dangerous myth 14:28 Luck vs. skill and the evidence against beating the market 15:39 Index funds, market efficiency, and investor behavior 16:49 Morningstar vs. other research tools 17:18 Empower's “free portfolio review” and what might be coming next 18:06 Portfolio concentration concerns and tech exposure 19:33 Humor break and annuity skepticism 20:55 What Empower actually is and what that implies 21:16 Empower as an RIA and how to treat their recommendations 21:52 Getting a second opinion from a fee-only advisor 22:58 Thanks, holiday wrap-up, and call for more questions Learn more about your ad choices. Visit megaphone.fm/adchoices

Today's show turns a national mood ring into a money lesson. Don and Tom walk through a new Wall Street Journal/NORC survey that sorts Americans into four emotional quadrants—comfortable optimists, comfortable pessimists, stressed optimists, and stressed pessimists. Tom takes the quiz live, landing squarely where most Americans do: personally comfortable, broadly pessimistic. The two unpack why sentiment is so gloomy despite solid personal finances, how risk tolerance shifts with market cycles, and why feelings often overpower facts. Listener questions follow on retirement diversification, how much risk one really needs if Social Security covers the bills, whether younger investors should ever be 100% in stocks, and the practical challenges of automatic withdrawals from ETF-based portfolios. 0:04 Don's intro and NPR-style location banter 1:08 Why the episode is about how we feel about money 1:40 Explaining the four sentiment quadrants in the WSJ/NORC poll 3:12 Tom begins the quiz: current financial satisfaction 4:23 Confidence levels across jobs, savings, and expenses 6:04 Vacations, stock market reactions, and financial worry 8:10 Comparing today's challenges to parents' generation 9:18 Buying a home, marriage, caregiving 10:07 Rating the strength of the U.S. economy 10:46 Optimism about the future and “the American dream” 11:26 Expectations for the next year and future generations 13:06 Results: Tom is a “comfortable pessimist” 14:44 Why pessimism dominates the national mood 15:16 What individuals can—and can't—control about tomorrow 16:29 Listener question: retiring at 63 with mixed assets and too much cash 19:14 How risk tolerance should drive allocation, not income sources 20:35 Fixing the portfolio's biggest issue: excess high-yield savings 21:54 Listener question: should a 47-year-old investor be 100% stocks? 23:11 Why very few people can stomach a 50% decline 23:59 The case for diversification even when accumulating 24:44 Listener question: automatic ETF withdrawals in retirement 26:15 Annual or semiannual rebalancing as a solution 27:28 ETFs vs. mutual funds: cost vs. convenience 29:13 Year-end cleanup and planning habits Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom take a sharp look at Vanguard's surprising new direction, especially the decision to fold annuities into 401(k) target-date funds through lightly regulated collective trusts. They contrast Vanguard's historical simplicity with today's trend toward complexity, comparing costs, structure, and risk across major providers. Listeners call in with questions about Roth conversions, Schwab target-date funds, entering the market after a forced delay, and whether TIPS or buffered ETFs are worth owning. Throughout, Don and Tom hammer home the fundamentals: low costs matter, complexity harms investors, active management rarely pays, and your stock/bond mix—not gimmicks—drives long-term success. 0:04 Opening and setup: Vanguard's recent drift toward complex products 1:03 Vanguard's dominance in target-date funds and why simplicity used to be the point 1:58 Vanguard adding annuities into 401(k) target-date funds — is this helping anyone? 3:11 What does an annuity inside a target-date fund even mean? 4:03 The 25% annuity allocation example and the misleading “8% payout” illusion 5:03 TIAA's role and why annuity costs remain unclear 6:28 Are annuities inside retirement plans a solution in search of a problem? 7:38 The fine print: Vanguard's new collective trusts and weak disclosure requirements 8:20 Why collective investment trusts are lightly regulated and potentially concerning 9:07 Caller: Roth conversions when you're withdrawing to live on — should you stop? 11:32 When Roth conversions lose their benefit and why you need cash for taxes 12:21 Caller: Are Schwab target-date funds worth it in a Roth? (Short answer: No.) 13:31 Why Schwab's higher fees and low international allocation are a problem 14:52 Active management inside target-date funds — unnecessary and risky 16:12 Risk vs. return: Schwab's higher volatility and lower historical performance 16:41 Caller: Missed market gains while transferring funds — how to get back in 18:49 When market discomfort signals a stock/bond misalignment 20:16 Comparing Schwab vs. Vanguard target-date funds over 15 years 21:37 Why lower cost + lower volatility + better return makes Vanguard the clear win 22:02 Should you fear future gimmicks like private credit inside target-date funds? 23:29 Caller PSA: Realizing capital gains in a low-income year 24:06 ETF explosion — 908 new ETFs this year, most using leverage or derivatives 25:29 Why “ETF” doesn't mean good; junk ETFs equal junk mutual funds 26:05 Structural benefits of ETFs and why the market prefers them 27:29 Soccer vs. NFL detour, then back to phone calls 29:07 Listener question from Colorado: Should you buy a TIPS fund? 31:01 Why TIPS rarely add value in diversified portfolios 33:22 TIPS behave more like inflation bets than true inflation protection 34:34 Why simple, short/intermediate, high-quality bonds—and CDs—often do the job 36:17 Caller: What is a buffered ETF, and why does it sound like an annuity? 37:29 Buffered ETFs explained: expensive, complicated, and unnecessary 38:30 Why gimmicks dominate product launches and how they hurt investors Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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.) Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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” Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Learn more about your ad choices. Visit megaphone.fm/adchoices

This Friday Q&A tackles a familiar voice: Bitcoin Bob tries again to make the case for crypto as protection against currency debasement. Don breaks down what “debasement” actually means, why inflation gradually reduces purchasing power, and why Bitcoin's extreme volatility makes it a poor replacement for the U.S. dollar. Productive assets remain the historically reliable hedge. Then: a comparison of target-date funds vs. a DIY three-fund portfolio, guidance for a couple aiming for early retirement with multi-account withdrawal planning, a discussion of equity/bond allocation in personal portfolios, and what might happen to the small China exposure inside global funds if geopolitical tensions escalated into war. 0:04 Friday Q&A intro and request for more listener questions 1:33 Bitcoin Bob returns: what “currency debasement” means 4:34 Bitcoin vs. the dollar: volatility and why stability matters 6:59 The real hedge: productive global assets over speculative tokens 8:29 Target-date funds vs. a three-fund portfolio in retirement 10:32 Asset allocation control vs. glide path defaults 11:20 Early retirement scenario: withdrawal sequencing, 72(t), and risk tolerance 14:55 When to add bonds and why emotional behavior matters 16:00 Don's and Tom's current equity/bond allocations 17:07 If the U.S. and China went to war: what happens to VT's China exposure? 20:26 Why global diversification limits catastrophic loss Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom take listeners on a wild ride through the booming (and frequently disastrous) world of leveraged ETFs. They break down how these funds promise double or triple the excitement but mathematically bleed away returns through volatility decay. A few listener questions follow, covering retirement cash buffers, negotiating advisory fees on large portfolios, and comparing IRTR vs AOM for a near-retiree allocation. Humor, subtle self-mockery, a Jonas Brothers detour, and a reminder that gambling is not investing. 0:04 Opening banter and the thrill-seeker pitch for leveraged ETFs 1:29 Leveraged single-stock ETFs explode from zero to $40B 3:26 MicroStrategy example: stock up ~30%, 2x ETF down ~65% 5:03 How volatility decay quietly destroys leveraged returns 7:36 5x ETFs and the “go to zero in one day” problem 9:01 When leverage stops being “investing” and starts being gambling 11:38 Listener question: Should retirees hold a bigger cash buffer to avoid selling in downturns? 14:37 Listener question: Should a $4M managed client negotiate fees? (Yes.) 17:43 IRTR vs AOM comparison for someone three years from retirement 22:54 Seasonal weather rant and hunkering down for productivity Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle the universal truths of investing — namely, that most investors underperform the market due to their own behavior. They discuss the persistence of emotional decision-making, the dangers of market timing, and the importance of diversification and sticking to a plan. Listener calls cover UGMA accounts, bond allocation in IRAs, downsizing for assisted living, robo-investing, annuities, and advisor ethics. The show mixes data-driven insight with classic Real Money humor and real-world financial guidance. 0:04 Universal truths of investing and investor behavior 2:07 Why investors underperform their own funds (Morningstar “Mind the Gap”) 3:30 Market sentiment, cash levels, and memories of 2000 and 2008 4:31 Peter Lynch on market corrections and investor overconfidence 5:40 The danger of timing the market and trusting stocks too much 6:40 “Financial Flinch Reflex” parody PSA (Appella Wealth ad) 7:41 Listener: diversifying a Vanguard UGMA for grandson's education 12:14 Listener: TSP rollover, age-based bond allocation, and risk tolerance 14:40 The right asset mix for long-term investors in their 40s 15:48 Listener: selling condo for assisted living — planning for late-life care 18:45 Spending vs. inheritance — why it's okay to use your own money 20:27 Producer's question: is SoFi robo-investing safe for beginners? 22:56 Emergency funds vs. long-term investing; debt priorities 26:03 Listener: spouse investing in individual stocks — handling differences 28:32 Listener: total market vs. S&P 500 core fund; AVGE and DFAW explained 30:17 Listener: 8% annuity “crediting rate” myth and why it's misleading 35:42 Real internal rate of return on annuities and risk comfort 37:12 Listener: following advisor from Ameriprise to a bank — fiduciary warning 39:36 Why commissioned products persist and how fiduciary rules differ Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle the timeless question: why do you invest? They challenge the “TINA” mindset (“There Is No Alternative”) and dissect new research claiming retirement savers should own no bonds at all. They argue that while stocks outperform over long stretches, bonds remain essential for emotional stability and survival during market crashes. Listeners join in with sharp questions about CD ladder withdrawal strategies, crypto-based dividend schemes, securities lending, and international ETF allocation. The show wraps with a skeptical look at Vanguard's growing tilt toward active management and new global funds from Avantis. 0:04 Why do you invest? Defining purpose versus chasing returns 1:29 The rise of “TINA investing” — there is no alternative to stocks? 2:30 Bonds as shock absorbers when markets collapse 3:57 Questioning global overweights in new stock research 5:01 The emotional toll of chasing maximum returns 6:12 Bonds' true role: keeping investors calm and consistent 7:50 Zweig's conclusion — even he still owns bonds 9:06 Retirement timing risk and the case for diversification 10:29 Caller Jay from Georgia — testing a five-year CD ladder withdrawal plan 12:34 Turning the CD ladder into part of a bond portfolio 13:46 What to do with the ladder during a market downturn 14:47 Caller Jason from Washington — Elon Musk, Bitcoin, and the “Strike/Strive” gimmick 15:49 The math behind high-yield crypto preferreds doesn't add up 17:18 When hype meets hazard: Ponzi parallels in risky yields 18:57 Why “everyone's doing it” isn't a defense for bad strategy 20:04 Why MicroStrategy's dividend promises defy logic 21:15 Listener question — securities lending in IRAs 23:09 How stock lending actually works (and why it barely pays) 24:18 Why most small investors shouldn't bother 27:15 Vanguard's new identity crisis: the push into active management 27:47 The profitability problem of index funds 28:53 Can Vanguard's active funds really beat their benchmarks? 31:48 Why past performance still fails as a predictor 33:14 Vanguard's crypto flirtation and industry pandering 35:43 Caller Craig from Seattle — expanding global exposure with AVNV 36:32 The case for adding Avantis International Value ETF 37:46 Early results and long-term expectations Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom unpack why even smart, financially literate people sometimes need a financial advisor — prompted by Morningstar's Christine Benz explaining why she hires one. They explore the value of second opinions, professional organization, tax guidance, spending permission, and succession planning. The conversation also draws lines around who doesn't need an advisor (DIY investors under 50 with good discipline) versus who does (retirees, disorganized investors, and anyone over 65 facing complexity). Later, they tackle listener questions about small-cap value ETFs — comparing AVUV, DFSV, and SLYV — and close with a retirement scenario review for a disciplined 77-year-old federal retiree. A lighthearted finish touches on long-term care insurance, empty nesting, and the Raiders' black hole stadium. 0:04 Reintroducing the need for financial help (but not that kind of help) 1:17 Christine Benz's surprising admission: she has a financial planner 2:27 The value of a “responsible second opinion” 3:25 Why Benz says peace of mind has real value 3:50 Reasons to hire an advisor: second opinions, tax guidance, rebalancing, perspective 4:54 When hourly financial advice makes sense 6:38 Organization and accountability as hidden benefits 8:08 The disinterested spouse problem 8:40 Why succession planning matters more than you think 9:32 “Permission to spend” — an underrated role of advisors 10:19 Who doesn't need an advisor: young savers and disciplined investors 11:27 When to get a second opinion even if you're DIY 12:18 Spotting bad advice and hidden annuities 13:03 Who does need an advisor: hodgepodge portfolios and over-50 investors 14:09 Complexity and the need for help beyond 65 14:47 The problem of small investors being preyed upon by salespeople 15:52 Listener question: adding small-cap value exposure 16:47 Comparing AVUV, DFSV, and SLYV performance and structure 19:00 Expense ratios and diversification differences 20:18 Don and Tom's ETF verdict 21:10 Retirement checkup: 77-year-old with pension and LTC coverage 22:06 Evaluating liquidity, income, and survivorship 23:48 The vanishing quality of long-term care policies 24:56 Tom's empty-nest plans and aching knee 25:43 Raiders jokes and the black-painted stadium Learn more about your ad choices. Visit megaphone.fm/adchoices