Talking Real Money - Investing Talk

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

Don answers a range of listener questions covering topics from Fidelity’s fully paid lending program to the Roth 401(k) decision and mortgage payoff strategies. He explains why stock lending rarely adds much value for ETF investors, why paying off a 2.6 percent mortgage makes little financial sense, and why even Berkshire Hathaway isn’t a substitute for true diversification. Listeners also learn about HSA payroll tax savings and how to build Roth flexibility without triggering the pro-rata rule. 0:04 Friday Q&A intro and listener invitation 1:25 Fidelity’s fully paid lending program explained—small returns, limited upside 3:47 When stock lending might make sense for rare or hard-to-borrow shares 4:33 Mortgage payoff debate—2.6% rate vs. 7% investing return 5:30 Don confirms: investing wins, emotion aside 7:09 Caller argues for Berkshire Hathaway B as the “perfect” one-stock portfolio 9:14 Don dismantles the myth—Buffett’s own warnings, risk concentration 11:23 401(k) vs. Roth 401(k)—how to decide and why a plan matters 14:04 Backdoor Roth options for self-employed spouses 15:32 Importance of long-term planning once portfolios near $1 million 15:56 HSA payroll advantage—no Social Security tax on contributions 17:11 Using a Roth to store “extra mortgage” money until retirement 18:08 Why paying off a low-rate mortgage later may not make sense 19:37 Free fiduciary portfolio checkup offer from Apella Wealth Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom open with an honest reflection on market déjà vu—how today’s investing climate echoes the speculative excesses of 1929 and 2008. Citing Andrew Ross Sorkin’s new book 1929: Inside the Greatest Crash in Wall Street History, they discuss the modern “financialization” wave: private equity, venture capital, crypto, and private credit being repackaged for retail investors and even 401(k)s, often under looser regulation. They warn listeners about “mark to make-believe” valuations and Wall Street’s relentless drive to sell complexity to the masses. The conversation moves from cautionary history (leveraged trusts of 1929, margin loans, and subprime mortgages) to present-day parallels like Bitcoin ETFs and private-market tokens. The takeaway: avoid opaque, speculative products; stick with transparent, low-cost diversification. In the Q&A, they answer listener questions about simplifying global portfolios with VT vs. VTI/VXUS, and about selling or donating concentrated stock positions from employee plans. 0:04 Opening disclaimers and acknowledgment that the episode isn’t meant to scare investors 1:18 Historical parallels—1929, 1987, 2008—and the feeling of “market déjà vu” 2:10 Introducing Andrew Ross Sorkin’s new book 1929 and his NYT column on modern speculation 3:20 Financialization and the loosening of investor protections in the 2020s 4:33 Wall Street’s constant invention of confusing products that favor sellers 4:58 Robinhood’s Vlad Tenev and the illusion of democratizing risk 6:12 Lowering the barriers to private markets and what that means for investors 7:26 Echoes of 1929: leveraged ETFs, margin-like structures, and “Russian-doll” debt 8:29 The perils of leverage and speed of modern market declines 9:02 Private-market tokens and the “mark-to-make-believe” problem 10:25 Overvaluation, lack of liquidity, and Wall Street’s interest in 401(k) assets 11:41 Historical leverage shifts—from banks to private credit 12:58 Why trusting financial “authorities” can be dangerous 13:32 Emotional honesty: people lie, and investors must self-protect 14:42 Jealousy, lottery-thinking, and envy as behavioral pitfalls 15:36 Investing as elimination—avoid what’s complex, costly, or confusing 16:48 Listener Q&A: two-fund simplicity (VT + BND) vs. multi-ETF tinkering 18:38 The temptation to overweight U.S. equities 20:00 Contrarian case for international exposure (VXUS) 21:15 ESPP stock cleanup: when to sell concentrated holdings 22:44 Charitable giving of appreciated stock for tax efficiency Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom go after one of their favorite targets: bad actors in the financial industry—especially those who flee regulation by becoming insurance salesmen. They break down a shocking new study showing that 98% of brokers kicked out by FINRA stay in the business by selling annuities and other insurance products, often with little oversight. The duo compares this behavior to “cockroaches,” slamming state insurance commissions for weak enforcement and minimal fines. Later, they tackle Washington State’s ballot measure SR 8201 on investing long-term care funds, answer listener questions about 529 plans versus UTMAs, discuss 457 plan costs and fund choices, and close with a fun chat about Halloween chaos and coffee and cocoa prices. 0:04 Opening rant on misbehavior in the financial industry and the perils of “bad advisors.” 1:03 How fired brokers reappear as insurance salesmen—98% stay in the industry. 3:10 Why state insurance oversight is toothless and how low the penalties really are. 5:14 Insurance firms masquerading as planners—why fiduciary-only advisors matter. 6:03 The study’s “cockroach” comparison and why the problem persists. 7:37 How to vet your advisor using FINRA’s BrokerCheck and state insurance lookups. 9:16 State vs. federal regulation—why the insurance lobby spent $200 million to avoid SEC oversight. 11:08 Caller Beth from Washington asks about SR 8201—investing long-term care funds in stocks. 13:27 The fiduciary perspective: diversification and realistic expectations. 15:23 Caller Gene from Puyallup on 529 plans vs. UTMAs for grandkids. 17:55 Tax control, gift rules, and the best state 529 options. 19:20 Holiday gifting and a little banter about who’s on Tom’s “nice list.” 20:22 Halloween costumes, tourists, and Celebration, Florida trick-or-treat madness. 23:28 Behind the scenes: Don reveals the entire “Talking Real Money” production staff (himself). 24:32 Podcast email list plug—how to subscribe at TalkingRealMoney.com. 25:35 Explaining podcasts for the AM radio crowd—how to find Talking Real Money on your phone. 27:30 Listener question from Matthew in Illinois about 457 plan costs and hidden fees. 30:38 The truth about 457s, penalties, and why Schwab’s low-cost ETFs may be smarter. 32:34 Caller Rob from Bellevue discusses attending RetireMeet and noticing the Apella building. 33:18 Wrapping with cocoa and coffee futures—good news for chocolate, bad for espresso lovers. 37:49 Don plugs Litreading’s Scary Story Season before switching to Christmas stories. Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle the timeless topic of diversification — why it’s back in style, why it’s so hard to maintain, and why most investors (and pros) still get it wrong. They walk through how market “leadership” shifts over decades, the global vs. U.S. split, and why comparing your portfolio to the S&P 500 is often a trap. Listener questions cover ETF access at T. Rowe Price and Vanguard, whether to invest or pay down debt, and how the 5% flexible withdrawal rule works in early retirement. Plus, the guys riff on Halloween candy inflation, Social Security COLA bumps, and Don’s LitReading “Scary Story Season.” 0:04 Show open — Saturday radio edition and why repetition matters in financial education 1:03 The fashion of diversification — and why it’s “back in style” 2:27 International and small-cap value resurgence 3:15 Why investors chase past returns instead of diversifying 4:02 Gold, inflation, and recency bias — lessons from the 1980s 5:21 U.S. vs. international allocation debate: market cap vs. 50/50 6:20 The long wait for Japan’s market recovery 7:41 Practical diversification tools — AVGE, DFAW, VT 8:19 Stop comparing everything to the S&P 500 9:08 Historical proof: global portfolio vs. S&P since 1931 10:02 Caller Charlie — buying Avantis or DFA ETFs through T. Rowe Price or Vanguard 12:39 How fund custodians differ from managers 13:27 Checking portfolio exposure with Morningstar 14:42 Caller Gabe — invest or pay off debt? 16:45 When to pay off a car loan vs. mortgage 19:35 How to handle multiple mortgages and long-term plans 20:22 Social Security’s 2026 COLA bump and the “good news/bad news” of $102 more a month 22:21 Inflation realities — coffee, beef, and Halloween candy 25:02 Candy talk — shrinkflation and Don’s trick-or-treat haul 25:54 LitReading plug: “Scary Story Season” and Philip K. Dick’s The Hanging Man 27:34 Search “Don McDonald” in Apple Podcasts — chiropractor cameo included 29:05 Listener Victor (a.k.a. George) — can $4 million last 60 years with 5% withdrawals? 31:38 How the flexible withdrawal method works in practice 33:49 Retirement purpose, Monte Carlo results, and FIRE skepticism 37:41 Kindleberger quote on bubbles and envy: “There’s nothing so disturbing as to see a friend get rich.” 38:55 Kindleberger’s background and Manias, Panics, and Crashes Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom Cock and Apella Wealth advisor Roxy Butner team up for a lively listener Q&A episode covering everything from the new wave of penny-stock IPOs to retirement readiness and tax traps. Tom opens with a warning about the surge in risky penny-stock offerings, then the two dive into listener questions about annuity sales pressure at Fidelity, portfolio diversification mistakes, CD taxation myths, Roth conversions, and one standout 21-year-old listener getting her financial life off to a stellar start. 0:05 Tom opens with a warning about the explosion in penny-stock IPOs 1:26 Why “lottery-ticket” stocks nearly always burn investors 2:21 Diversify, stay tax-efficient, and skip the hype 2:30 Roxy joins for listener Q&A 3:38 Fidelity’s annuity pitch — a listener wonders if it’s time to leave 5:05 Who’s truly fiduciary: Fidelity vs. Vanguard vs. Apella 6:14 Vanguard dipping a toe into crypto 6:51 Quabina from Ohio: $2.2M at 47 — diversified enough to retire at 55? 8:14 Missing global diversification and bonds in an all-U.S. portfolio 9:57 Early-retirement planning challenges and healthcare costs 10:20 How to design the right stock-bond-international mix 11:36 Daniel from California: Are long CDs taxed as capital gains? 13:04 Why CD interest is always ordinary income — and muni bond alternatives 13:29 Year-end planning: RMDs, Roth conversions, and tax optimization 14:45 Common tax mistakes and mis-placed assets 15:19 Emily from Ohio: “Young and Dumb” — a 21-year-old investing the smart way 18:51 Building a first Roth IRA and why bonds don’t belong yet 20:00 One-fund simplicity: AVGE vs. VOO 21:41 Long-term mindset: global diversification and patience pay off Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle another full “Q Day,” answering listener questions on Roth fund selection, bond fund gimmicks, real estate returns, California’s odd HSA tax treatment, switching from Vanguard to Avantis, copying politician trades, and whether Vanguard’s Cash Plus account beats its money market fund. The episode mixes practical investing logic with humor, skepticism, and a bit of Don’s plug for his new storytelling podcast, New Tales Told. 0:04 Q Day begins — Don riffs on “Q” words and high-quality listener audio 1:42 Betsy from Minnesota asks: best funds for a Roth IRA (AVUV, VOO, AVGE) 2:39 Don suggests simplifying to AVGE, but warns of risk and emotional resilience 4:12 Jesse from Seattle on CPAG “tax-efficient” bond ETF — Don calls it a gimmick 5:55 Don’s math: CPAG only helps slightly at 35% tax bracket, not worth complexity 9:06 Listener compares 403(b) vs. home value growth — Don confirms results typical 12:45 Real estate’s weak real return over time and lifestyle vs. investment value 12:45 California HSA confusion — Don explains CA taxes HSAs like normal accounts 15:22 Nathan from Georgia: Vanguard vs. Avantis funds, and “copy politician trades” 17:20 Don: Avantis adds small/value tilt, AVGE can simplify portfolio management 19:14 Don: “copy-trade” apps are expensive, delayed, and silly gimmicks 20:58 James from Virginia: Vanguard Cash Plus vs. money market funds 22:34 Don explains FDIC difference and risk-reward tradeoff, prefers money market 24:11 Closing reflections, legacy talk, and plug for New Tales Told Learn more about your ad choices. Visit megaphone.fm/adchoices