Talking Real Money - Investing Talk

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

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

Don and Tom revisit the Social Security debate after new Wall Street Journal and New York Times articles challenge long-standing advice to delay claiming. They dismantle clickbait claims that “waiting doesn’t make sense,” highlighting emotional biases, unrealistic investment assumptions, and spousal benefit considerations. The episode also covers whether Social Security counts as an asset, then shifts to listener questions about 529-to-Roth rollovers for graduate school, switching funds in an IRA, and managing company stock in an ESOP-based 401(k). 0:00 Why they keep returning to Social Security and why 25% of retirees rely on it entirely 1:43 Two-thirds claim before full retirement age; Wall Street Journal’s clickbait headline 3:02 The “bird in hand” fallacy and instant-gratification bias 3:48 Don’s confession: took Social Security at 69—and dogs ruined the travel plans 4:40 WSJ’s faulty 5%-return argument and why most investors won’t achieve it 5:43 The math: waiting pays more monthly, but longevity is the unknown 6:32 Trade-offs between retiring early, portfolio drawdowns, and spousal benefits 7:35 NYT’s claim that Social Security is America’s most valuable “asset” 8:08 Don’s rebuttal: it’s income, not an asset—you can’t liquidate it 9:49 Why people misclassify Social Security and how bonds fit differently 10:08 When and how to get a second (fiduciary) opinion on claiming strategies 11:00 The plague of commission-driven “advisors” and fake fiduciaries 12:29 Old brokerage “no-load fund” lies and how similar games persist today 12:40 Listener Q&A: overfunded 529 plan vs. Roth rollover for grad school 14:27 Midwifery degrees, student-loan math, and the 5% rate cutoff 17:13 Rollover IRA question: switching Fidelity funds to Vanguard ETFs 18:15 Active vs. index funds—why fees and diversification matter 20:05 Active-active management and small-cap risk humor 20:54 ESOP question: how much company stock is too much? (Hint: under 5%) 22:42 Selling discipline and diversification in employee-owned firms 24:39 Don and Tom joke about their own ownership and “sell-out” strategy 25:04 Daily calls, good-natured ribbing, and reminders about Saturday’s live show Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dive into common misconceptions about what’s really been the top-performing asset class over the past five years—spoiler: it’s not the S&P 500. They compare U.S. large-cap growth with international small-cap value, using Larry Swedroe’s data to highlight the importance of global diversification. Listeners call in about estate planning, withdrawal rates in retirement, and portfolio construction. The hosts explain community property rules, flexible withdrawal strategies backed by research, and which small-cap value ETFs they prefer. The episode closes with a reality check on Bitcoin’s latest crash, revisiting Mark Hulbert’s warning that crypto isn’t an asset class but a risky “thingy.” 0:04 Opening banter on the show’s long Seattle run and mission to simplify money. 2:08 The S&P 500 obsession—why investors overweight large U.S. growth stocks. 3:23 Larry Swedroe’s quiz: best-performing asset class 2019–2025 (hint: it’s not U.S. large growth). 4:07 Dimensional International Small Cap Value Fund (DISVX) vs. S&P 500 Growth (VOOG). 5:20 Why diversification and global exposure matter long-term. 6:20 Break: “Financial Flinch Reflex” PSA. 7:42 Diversification means holding assets that sometimes disappoint you. 8:33 Don’s marriage analogy and listener call-in from Baltimore about trusts. 10:15 Estate simplicity, beneficiary designations, and when trusts are unnecessary. 11:55 The danger of “trust mills” and the value of family transparency. 14:40 Community property vs. joint tenancy—Washington’s unique tax advantage. 16:36 Call from Michael: flexible vs. fixed withdrawal rates in retirement. 17:29 Why a 5% flexible withdrawal often beats the classic 4% rule. 20:19 Research roundup: Kitsis, Vanguard, Morningstar confirm flexible success rates. 23:09 Listener from Tennessee asks about capital-gains exclusions. 25:44 Chris from Seattle: using target-date funds to fix a “hodge-podge” portfolio. 27:24 Adding small-cap value (AVUV) to target-date funds for tilt and simplicity. 28:34 Listener from New Hampshire asks which planning software Appella Wealth uses. 30:06 Call from Sam: best small-cap value ETF options (AVUV vs. VBR). 33:21 Risk, volatility, and why small-cap value offers higher expected returns. 35:47 Mark Hulbert on crypto’s crash—bigger than 1929 by percentage. 36:54 Why hype, not utility, drives crypto coverage. 38:36 Final takeaway: investors remain too U.S.-centric; diversify globally. Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom kick off by joking about their “record-breaking” call drought before diving headlong into the week’s biggest speculative loser: crypto. The duo dismantle the mythology around Bitcoin and its countless imitators, comparing the excitement of trading coins to sports betting and reminding listeners that portfolios are for investing, not gambling. They tie the current crypto crash to leverage, insider-like trades, and the same fraud patterns seen in history’s great financial cons—from Jay Gould’s gold-cornering to Elizabeth Holmes’ blood-testing farce. Later, they field listener questions on asset location, liquidity management, emerging-market exposure, and the danger of leverage via MicroStrategy’s Bitcoin bet. Through it all, they emphasize fiduciary discipline, skepticism toward hype, and the basic rule: excitement and good investing rarely mix. 0:04 Pretending last Saturday’s show didn’t happen; Tom’s pun about “Pacific” questions. 1:41 Crypto crash carnage—Bitcoin off 16%, Ethereum down 25%, “Trump Coin” collapsing. 2:30 Comparing crypto’s thrill-seeking crowd to sports betting mania. 3:55 Why your financial advisor should not be your gambling coach. 4:48 The leveraged, insider-ish side of crypto speculation. 5:06 The absurdity of 10,000+ coins that serve no purpose but gambling. 7:40 Calling crypto “speculative” and comparing it to a casino roller coaster. 8:10 Binance payout trouble—proof many players don’t know how to run big-money businesses. 10:32 MicroStrategy’s leveraged Bitcoin plunge and the perils of margin. 11:37 The illusion of “value” in digital tokens versus productive assets. 12:55 Historical echo: borrowed money, bubbles, and 1929-style leverage warnings. 15:25 Listener questions segment opens; lighthearted banter about philately and call volume. 17:02 “ChatGPT beats bad advisors” — asset location done right (bonds in IRA, stocks in Roth). 18:30 Why most “advisors” ignore tax planning in favor of commissions. 20:23 Jay Gould, robber barons, and the Wall Street Journal’s bizarre defense of con artists. 22:12 From Nikola to Theranos—lying as business strategy and why “gray areas” hurt investors. 24:53 The moral cost of tolerating fraud disguised as innovation. 26:36 Why trust is the real foundation of capitalism, not creative deception. 27:00 How to protect yourself: fee-only fiduciary advice and due diligence. 27:36 Mariners hangover theory for low call volume; nostalgic TV banter (“Bewitched”). 29:06 Caller Tom (Seattle): $4 M portfolio, $1 M in money market—how much liquidity is too much? 30:34 The hidden risk of waiting too long to react when rates fall. 33:08 Building a CD ladder to lock yield without betting on one-day rates. 34:25 Quick take: Why they’d avoid owning Boeing stock individually. 36:18 Caller Justin (Florida): emerging-market allocation for high-risk investors. 37:29 Case for small-cap and value tilts, including emerging markets. 38:34 Should you exclude China? Why it’s still essential in global portfolios. 39:29 Closing reminders—use the website for questions, and find fiduciary help at TalkingRealMoney.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle a mix of market mania and listener questions, skewering speculative fads like meme stocks, SPACs, private credit ETFs, and covered-call funds. Don opens with a scam text story before the duo dive into the absurdity of “get-rich” products during a record-breaking market. They stress discipline, diversification, and turning off CNBC — repeatedly. Listener questions include Roth conversions in high tax brackets and funding a home purchase without wrecking retirement plans. The show ends on a hilarious tangent about listeners wearing backpack banners to promote Talking Real Money. 0:04 Scam text from Colorado and the hazards of living alone in a studio 1:09 Market highs and the illusion of perfect timing 2:35 Stock concentration, meme stock mania, and the “Magnificent Seven” dominance 3:34 Listener call: investing in a soccer team partnership promising 15–30% returns 5:12 Why “too good to be true” often is — scams and speculative traps 6:09 Covered-call ETFs (JEPI, GPIQ) explained and debunked 9:39 New private credit ETF (PCR): high fees, low transparency, huge risk 12:49 CNBC hype vs. reality — why turning off financial TV is sound advice 16:21 Listener question: Roth conversions and tax traps in the 30% bracket 19:26 Another listener: funding a new home without derailing retirement 21:47 Don’s rant on overpricing homes — “every house sells at the right price” 23:24 Real estate emotion vs. math — the price always tells the truth 24:31 Episode wrap-up: humor, gratitude, and an absurd “wearable banner” promo idea Learn more about your ad choices. Visit megaphone.fm/adchoices

Don answers six listener questions covering CD ladders vs. bond funds, global diversification for young investors, allocation shifts for early retirees, HSA documentation rules, 529 plan comparisons, and whether Dave Ramsey-style portfolios need bonds. He closes with practical guidance on holding cash for opportunities and a reminder about the value of disciplined, evidence-based investing. 0:10 Friday Q&A intro and how to send in questions 1:51 Are CD ladders a good replacement for bond funds? 3:37 How to build a disciplined CD ladder and avoid rate-timing mistakes 3:41 A father asks how to diversify his daughter’s Roth IRA beyond VTI 5:48 Couple planning early retirement—asset allocation and 72(t) options 9:41 Why bonds exist: emotional stability vs. return chasing 11:29 The case for international diversification 11:29 Long-term HSA strategy and what to do without old receipts 14:32 How to recreate expense records and save PDFs going forward 15:26 Which 529 plans are best for kids aged 2–12? (Utah vs. Schwab) 17:28 Dave Ramsey investing myths and the real purpose of bonds 20:36 When to start adding bonds—take the Talking Real Money risk quiz 21:00 Where to park six-figure cash for car or property purchases 22:46 Short-term safety vs. yield trade-off Learn more about your ad choices. Visit megaphone.fm/adchoices

Don swats a studio bug, then swats down the idea of dividend-driven retirement portfolios. Drawing on Jason Zweig’s interview with Richard Thaler, they explain why retirees should focus on total return—spending from a diversified portfolio rather than chasing yield. They hit Robinhood’s profit model, bid-ask spreads, and the need for automatic-enrollment retirement plans. A listener call leads to a discussion of Social Security timing, debt-free retirement, and (yes) hodgepodge-itis—Don’s term for chaotic portfolios. Things wrap with a jailed investor’s question, some gallows humor, and the usual banter about holidays and compliance. 0:04 Bug chaos and phone-line reminder 1:41 Why dividend-income portfolios are a trap 2:50 Jason Zweig & Richard Thaler on total-return spending 4:18 Total return beats “high-dividend” illusions 5:39 Robinhood’s option-spread profits and the myth of “free” trading 6:15 Schwab vs. Robinhood: relative honesty in bid-ask spreads 7:43 Thaler’s take on missing retirement plans and automatic savings 9:05 Anniversary talk and the failed “Debbie Show” experiment 10:15 Back to Thaler—why most workers still lack plans 11:39 Tesla options example showing 7 percent spread 12:05 Case for national retirement depository & hybrid Social Security 13:33 Hodgepodge-itis defined (and owned by Don) 14:51 Low call volume and the Mariners’ hangover 15:52 Listener Kevin asks about dividends vs. selling stock 16:53 Reinvesting dividends vs. total-return withdrawals 18:17 Dividends reduce company growth potential 19:45 Why high-yield chasing kills diversification 20:07 Caller David, age 67, plans retirement & asks how to prep 21:55 Social Security timing advice—benefits rise monthly 22:50 David’s details: city pension, deferred comp, house, no debt 24:07 Getting professional fiduciary advice before retiring 25:23 David’s crypto confession and $3K Ripple gamble 27:27 Jail-bound investor asks where to park money 30:18 Don & Tom debate investing from behind bars (humor intact) 33:19 Columbus Day scheduling confusion & closing banter Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom open with banter about the weather, baseball playoffs, and studio quirks before diving into what it means to be a “millionaire” today versus in 1890. They explore how much of modern net worth is illiquid, why home equity and retirement funds can trap wealth, and how planning for liquidity and income is crucial. The conversation transitions into a discussion of market volatility, rare earth trade tensions with China, and Brett Arends’ critique of index investing. They counter with historical perspective, humor (and potato chips), and advice about risk, rebalancing, and human behavior. Later, listener calls cover portfolio structure, Empower vs. Vanguard advisor options, and evaluating advisor fees and fund costs. The show closes with their classic blend of education, sarcasm, and fiduciary realism. 0:04 Opening banter, phone number, Florida “cold front,” and baseball chatter 2:33 Topic intro: What a million dollars means now vs. 1890 3:58 Comparing historic vs. modern millionaires and net worth equivalency 4:43 The illusion of wealth—why 70% of assets are often inaccessible 5:30 Planning for liquidity: why paying off a mortgage too early can backfire 6:37 Don’s retirement planning promo 7:39 Historical comparison: 1890s Gilded Age vs. today’s millionaire stats 8:19 Market globalization and modern wealth concentration 9:43 Rare earths and the U.S.–China tariff skirmish 10:22 Market check: stocks, bonds, and gold all dip; volatility talk 12:04 Don’s “unnamed thing” (Bitcoin) drops 10.5%; discussion on risk and rebalancing 13:48 Don shifts to 60/40 allocation—explains rationale near retirement 14:34 Brett Arends’ “Dumbest Stock Market in History” critique discussed 16:00 Debate: Are index investors stabilizing markets through consistency? 17:19 Potato chip tangent and investor psychology 18:32 Arends’ bearishness vs. evidence-based investing 20:00 Protecting your psyche, not every dollar, from market declines 20:20 Podcasting history—when Talking Real Money began 21:32 Caller Samir (Virginia): $4M net worth, suffering from “hodgepodge-itis” 24:15 Don and Tom’s prescription: stop investing until you have a plan 25:42 Margin loan temptation and why 10.5% interest kills the idea 27:00 Tom reinforces the need for a fiduciary planner 27:32 Caller Chris (Texas): moving from Empower to Vanguard PAS 29:21 Vanguard vs. Empower: conflicts, fund choices, and planning gaps 31:46 “Half-pregnant” advice models and Bogle’s legacy examined 34:20 Broader critique: single-provider risk and investor behavior 35:54 Caller Dave (Olympia): evaluating returns, fees, and portfolio costs 37:50 What’s a reasonable expense ratio and advisor fee range 39:24 Final takeaway: judge portfolios by structure, not short-term returns Learn more about your ad choices. Visit megaphone.fm/adchoices

In this playful and insightful episode, Don and Tom explore how the beloved Friends characters might fare financially if they were retiring today. Using their signature mix of humor and practical investing wisdom, they analyze each character’s fictional career, personality, and spending habits to project their retirement readiness. The second half of the show returns to real-world money matters, answering listener questions about blending withdrawal strategies and fund choices in employer retirement plans. 0:04 Why this episode starts with a Friends reference—and yes, it’s copyright-friendly 0:31 Monica and Chandler Bing as retirement savers: organized, driven, but maybe too perfectionist 3:25 Monica’s obsessive planning vs. Chandler’s possible risk aversion 4:22 Overthinking portfolios and the emotional toll of too much tweaking 5:01 Savers who struggle to spend: how Monica might hoard instead of enjoy 5:56 Chandler’s likely financial behavior and their combined million-plus portfolio 7:03 Ross: neurotic, divorced, and probably pension-supported 7:54 Why pensions are psychologically powerful for retirees 8:35 Ross would need an advisor to keep him calm and invested 9:14 Rachel: spender, low earner, fashion industry job—not retirement ready 10:30 Joey: the actor’s feast-or-famine finances and SAG-AFTRA pension potential 12:22 Real SAG-AFTRA pension expectations: modest but helpful 13:09 Joey’s likely retirement: modest income, limited comfort outside major cities 13:54 Phoebe: quirky, lovable… financially reckless? 14:28 Phoebe’s imaginary downfall: alimony, bad investing, busking in Times Square 15:20 Big picture takeaways: personality, income, and circumstance aren’t destiny—but they shape outcomes 16:48 The Bings win the retirement game… Phoebe’s husband probably doesn’t stay married 17:30 Listener Q1: Combining fixed and flexible withdrawal strategies 18:52 30-year portfolio simulation using 60/40 and AI tools 20:24 Hybrid strategy results: high survival rate, smoother ride, and growing payouts 21:21 Comparison of 4% vs. 5% withdrawal income over time 22:36 Listener Q2: Replacing expensive international funds in a union 401k plan 24:00 Replace EuroPacific and Developed with Fidelity’s low-cost international index fund 25:17 Expense ratio showdown: PigWX vs. FSPSX 26:32 Closing chaos: how to contact Tom and the long-lost newsletter phone number 27:49 Origins of 800-FUND-004 and how someone just walked into the Bellevue office 29:42 End credits and final laughs—yes, even Tom held back the dad jokes (mostly) Learn more about your ad choices. Visit megaphone.fm/adchoices

In this extended Friday Q&A episode, Don answers six listener-submitted questions covering a wide range of personal finance and investing topics. He kicks off with a fiery takedown of cryptocurrency as a viable asset class, arguing it’s based on hype and the greater fool theory. Other questions explore whether pensions should count as fixed income in asset allocation, the performance of Dimensional and Avantis funds versus traditional index funds, the pros and cons of Collective Investment Trusts in 401(k)s, and the strategic timing of Social Security. He ends by clarifying a common misconception about RMDs and Secure Act 2.0. Expect smart insights, a little snark, and the kind of blunt honesty that’s rare in financial media. 0:04 Listener Q&A returns with an extra dose—six questions this time 1:07 Confusing podcast scheduling clarified (sort of) 2:11 Crypto as an asset class? Don calls it “entirely invented” and dismantles the use case hype 4:32 If civilization collapses, your Bitcoin won’t save you 6:06 Crypto = greater fool theory; Don braces for hate mail 7:30 Dimensional/Avantis vs. index funds—do the extra fees pay off? 9:13 A 15-year comparison: Dimensional Global Equity vs. VT 11:43 Should a pension count as fixed income? Don says no—it’s a volatility game, not income 15:48 CITs (Collective Investment Trusts) in 401(k)s—cheaper, but less transparent 18:58 Index funds should be your benchmark; Don suspects this one’s active 20:02 Claiming Social Security early to preserve Roth? Don says the math rarely supports it 23:59 Secure 2.0 and RMD confusion—born in 1959? You still take RMDs at 73, not 75 26:15 Tech keeps improving—Don urges retirees to stay sharp, stay curious Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dive into a new Morningstar report showing that tactical allocation funds—those run by “smart” managers who actively shift investments—significantly underperformed simple buy-and-hold index portfolios. They unpack why doing nothing often wins, discuss investor behavior gaps, and revisit the power of staying the course. Listener questions follow on mortgage payoffs, TIAA advisory fees, and adjusting stock/bond splits in retirement. The episode wraps with Don revealing his personal creative project—his short story A Chance of Death on his LitReading podcast—and a teaser for his next story, Murder of Crows. 0:23 Morningstar headline: tactical allocation funds lose to “do-nothing” portfolios 1:45 What tactical allocation funds really are (a.k.a. expensive market timing) 2:52 Morningstar urges investors to “stay the course” 3:04 Revisiting “Mind the Gap” and why investors underperform their own funds 4:28 Data comparison: $10k in tactical vs. passive portfolio over 10 years 5:31 Why professionals can’t beat buy-and-hold investors 6:51 Human behavior, arrogance, and the illusion of market-timing skill 8:37 The need for a written plan and risk-based portfolio 9:58 If you have a plan, market noise stops mattering 10:22 Tangent: WWII documentaries vs. Taylor Swift’s Miss Americana 11:21 Listener question #1 – Paying off a low-rate mortgage vs. investing 13:35 Math and emotion collide: cheap money, liquidity, and peace of mind 15:35 Listener question #2 – TIAA Wealth Management fees and fiduciary standards 18:31 Reading TIAA’s ADV: possible fees up to 2% on small accounts 20:08 Comparing local RIAs vs. large institutions 21:08 Clarifying blended fees and fund costs 21:47 Listener question #3 – Vanguard advisor suggesting 60/40 allocation 22:53 Risk tolerance vs. risk need – the real balance 24:05 Investment Policy Statements and Vanguard’s advisory limitations 25:46 Call for more listener questions and upcoming Q&A shows 26:15 Don plugs Lit Reading and his new original story “A Chance of Death” 28:24 How AI collaboration shaped the story’s creation 30:59 Discussion of his next story, “Murder of Crows” 32:17 Invitation for audience feedback on Lit Reading stories Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom kick off this episode with a satirical bang—mocking the apocalyptic tone of a MarketWatch article about the “Fourth Turning,” a cyclical doom prophecy claiming America faces a cataclysmic reset every 80–100 years. Citing wars, depressions, and now AI, wealth taxes, and the fall of the dollar, the hosts break down the fatalistic tone, expose the fear-marketing behind it, and reassure listeners that, historically, markets have recovered—and rewarded long-term investors. 0:04 Faux alien warning: the Fourth Turning economic apocalypse is coming 1:16 Dissecting the MarketWatch article and the “Fourth Turning” theory 2:26 Peak catastrophe by 2030? AI job loss, collapsing dollar, wealth taxes 3:38 Don asks: what is this guy selling? Spoiler: $100M wealth club 6:01 $180k to join R360—clearly not for the average listener 6:33 Don’s “financial flinch reflex” PSA spoof (ad) 7:41 Tom: “We love being scared”—AI panic and deepfake video fears 9:07 Caller Sue (68): Ready to retire with $820k and SS? Don says yes 13:05 Sue’s next step: get a fiduciary checkup, maybe run Monte Carlo 14:10 Tom runs one: 50th percentile = she hits zero at 98 15:32 Flexible withdrawal rates might work better than rigid 4% 16:34 Listener voicemail: Should we switch from Roth to Traditional now? 18:16 DT’s Roth vs. traditional strategy: save taxes while you can 20:14 WSJ article on taxes and stock gains—do ETFs instead 21:25 Tax basics for investors: capital gains rates and efficiency 23:26 Mad Men nostalgia and mid-century tax rates 25:15 TV detour: Bewitched vs. I Dream of Jeannie vs. Outlander 27:10 Back to calls: Theodore asks about 403(b) options in Burlington 29:10 Don explodes: garbage annuity vendors dominate the plan 31:01 Aspire is the only halfway-decent vendor… if you avoid their advisors 33:54 Don tells how an Albuquerque teacher got Vanguard into their plan 35:44 Aspire hack: use FundSource for no-load mutual funds 36:14 Caller Steve: hold 20 stocks or sell and rebalance? 37:53 Tom: hybrid approach. Don: depends on need. Watch tax bracket Learn more about your ad choices. Visit megaphone.fm/adchoices

The show kicks off with a sardonic take on turf wars between delivery drivers—yes, really—before diving into third-quarter market returns, investor behavior, and asset class performance. Don and Tom remind listeners (again) that sticking with a diversified portfolio beats timing markets or following headline noise. Listeners call in about Social Security strategies, inheritance accounts for minors, and what to do with large sums of cash in retirement. The show wraps with a smart look at ETF-to-mutual fund conversions and why the old-school fund industry is getting left in the dust. 0:11 Delivery turf wars joke and quarter-end reflections 1:40 Fears vs. reality: inflation, jobs, and trade wars 2:16 Q3 returns: U.S. stocks +8%, EM +9.6%, silver tops, cocoa flops 3:09 What you had to do to earn those returns: be invested, diversified, and ignore noise 5:13 Don scolds investors still avoiding value and international stocks 6:11 Chocolate aside, it’s been a strong year for stocks and bonds 7:42 Promo: Why guessing isn’t a retirement plan 7:51 Don recovers from a cough; Tom lists worst Q3 performers (lean hogs!) 9:13 Listener Chad argues for claiming Social Security early if you can earn 3% 11:08 Don crunches the math: break-even at age 81–82 if invested at 3% 12:57 Survivor benefits and why waiting helps your spouse 13:57 Don jokes about his wife stealing his life force and living to 112 14:54 Vaccine banter and intro to next caller 15:56 Caller Michael from Burien sells a condo, asks where to put $300k 19:07 Don and Tom suggest municipal bonds like VTEB for tax-free yield 20:20 Michael quotes a great retirement planning aphorism 20:29 Shift to ETF inflows and the downfall of mutual funds 29:13 Vanguard’s tax-free conversion model and Dimensional’s exemptive relief 30:49 What this shift means for investors with taxable accounts 31:17 Mutual funds may soon be the next buggy whips 32:22 Listener Connie asks: do you really get back Social Security withheld when working before FRA? 33:14 Tom and Don clarify: benefit adjusted later, but no “refund” 34:37 Caller Susan from Connecticut: what to do with $250k in cash 36:52 Don: You don’t need more products—you need a real financial plan 39:17 Flat-fee plans and how to find a true fiduciary Learn more about your ad choices. Visit megaphone.fm/adchoices

A lively, unscripted listener Q&A episode with no set topic — just a flood of great questions. Don and Tom tackle everything from inheriting farmland to the hidden cost of medical inflation, tax-efficient short-term investments, Ameriprise conflicts of interest, fund turnover ratios, and a heartfelt tribute to the late Jonathan Clements, a true pioneer of rational investing journalism. Plenty of wit, warmth, and straight talk about money — plus a personal moment of honesty from Tom about life, loss, and gratitude. 0:04 Cold open: “A show with no topics” banter and weather humor 2:07 Angie from St. Paul: Inheriting farmland — hold or sell? 6:04 Anton from Spokane: Medflation’s impact on Social Security COLA and Medicare premiums 10:45 Jason from Tigard: SPAXX vs. SGOV — which is better for short-term cash? 13:35 Ameriprise client: Should I use an SMA or fire my advisor? 18:41 Luke from Evans, GA: ETF turnover and what it really means 23:25 Tribute to Jonathan Clements — his life, legacy, and impact on index investing 27:10 Personal reflections, audience appreciation, and gratitude from Tom Learn more about your ad choices. Visit megaphone.fm/adchoices

In the longest Q&A episode yet, Don answers seven listener questions covering everything from concentrated stock windfalls and early retirement asset allocation to Roth vs. taxable contributions, the real 59½ withdrawal date, the dangers of buffered ETFs, and the reality of home affordability. He stresses the importance of security over speculation, the need for actual retirement planning, and the pitfalls of gimmicky Wall Street products, all while weaving in his trademark skepticism and humor. 0:04 Friday Q&A intro and listener surge in questions 2:18 Jackpot in two small-cap stocks at age 70—should he sell? 6:28 42-year-old with uncertain job security and $850k retirement + $518k taxable—structuring allocations for early retirement 11:28 Roth vs. taxable brokerage contributions for flexibility before 59½ 15:13 Clarifying 59½ rule—date vs. year of eligibility 17:11 Buffered ETFs explained and why they’re just Wall Street gimmicks 21:53 Rule of thumb for first-time homebuyers: mortgage % of income, 15 vs. 30-year terms, and why homes aren’t great investments Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle Americans’ retirement fears, highlighting a survey where one in five say it would take “a miracle” to retire securely. They stress the importance of planning over wishful thinking, cover the risks of recency bias, taxes, and underestimating longevity, and explain why flexibility—delaying Social Security, working part-time, downsizing, or even using a reverse mortgage—may be essential. Listener questions include a 30%+ ETF return (AVDV), the new rules allowing 529 rollovers to Roth IRAs, and a deep dive into Facet Wealth versus Northwestern Mutual, with a reminder about low-cost index investing and the value of fiduciary advice. 0:04 How confident Americans are about retirement security 1:37 “It would take a miracle” vs. “You need a plan” 2:37 The value of professional reviews and planning tools 3:52 No perfect time to retire, recency bias, and government as your “partner” 5:08 Retirement timing compared to parenthood decisions 6:06 The limits of Social Security and lifestyle realities 7:18 Adapting by working longer, delaying Social Security, or reducing expenses 8:25 Cutting wants, working part-time, or considering home equity solutions 9:23 Reverse mortgages and staged retirement strategies 10:03 Purpose, social life, and health in retirement 11:25 Listener question: international ETF with a 30%+ return (AVDV up 38% YTD) 13:02 Why diversification matters for capturing those “30 percenters” 13:22 Listener question: 529 rollovers to Roth IRAs and beneficiary changes 16:21 Listener case study: RN nearing retirement, Facet vs. Northwestern Mutual 18:07 Facet’s flat annual fee structure compared to traditional AUM fees 20:54 The pitfalls of Northwestern Mutual’s high fees and insurance roots 23:34 When to hire a fiduciary and why $1.5M+ means it’s time 25:30 Advisor costs vs. DIY investing, plus an extended “haircut analogy” 27:13 Shout-out to AI-generated Talking Real Money show art Learn more about your ad choices. Visit megaphone.fm/adchoices

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

Don and Tom open with a tribute to financial writer Jonathan Clements, reflecting on his career and unique investing wisdom. They unpack five of his “pearls,” including saving early, avoiding big mistakes, and living an active, purposeful life. From there, they pivot into critiques of misleading annuity sales cloaked in fiduciary language, highlight changes coming to retirement account catch-up contributions, and tackle listener questions on bond ETFs, ETF vs. mutual fund conversions, CD strategies, and investing with a reluctant spouse. The show mixes respect for sensible investing voices with sharp criticism of gimmicks, all wrapped in listener calls and banter. 1:04 Remembering Jonathan Clements and his influence 2:59 Pearl #1: Make and save money early, passion can wait 3:54 Pearl #2: Winning isn’t everything—avoiding losers matters most 5:05 Pearl #3: The tax code rewards patience and savers 5:50 Pearl #4: Don’t just stand there, do something (in life, not trading) 7:37 Reflection on his loss and the scarcity of sensible money voices 9:34 Critiquing Kiplinger article and annuity sales cloaked as fiduciary advice 11:44 Pearl #5: Humans are built to strive, not sit idle—retirement requires purpose 12:40 Preview of rising early-retirement questions in upcoming Q&A show 13:22 Vacation banter, Disney’s Aulani resort, and “surfing together” joke 14:13 Back to annuity sales, fiduciary mask problem, and misleading disclosures 17:39 Listener email anticipating annuity criticism—prediction fulfilled 18:12 Listener call: pushback on jargon, “basis points vs. bips” debate 20:13 Listener call: bond ETF BINC—why it’s loaded with junk and risky 25:22 Explaining Roth-only 401(k) catch-ups starting 2026 for $145k+ earners 27:22 Listener call: ETF vs. mutual fund conversions, Vanguard’s patent, Fidelity status 31:29 Listener call: couple with $1.6M in cash, wife afraid of investing 35:36 Don and Tom’s advice: show need via a financial plan, start with small stock exposure 35:59 Listener call from Italy: CDs, interest rates, and laddering vs. penalties Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle the “big three” global equity ETFs—Vanguard VT, Dimensional DFAW, and Avantis AVGE—breaking down their diversification, costs, risk/return assumptions, style tilts (small/value vs large/growth), and geographic/sector weights. They highlight how DFA and Avantis add microcaps and factor tilts that Vanguard’s index omits, why fees are “pennies” but differences in construction matter, and why “rules-based” is more accurate than “active.” Listener questions cover lottery winnings (lump sum vs annuity), the collapse of Publishers Clearinghouse payouts, and Ameriprise’s pricey SMA accounts. The theme: investing lives in the middle ground—balancing risk, cost, and logic. 0:04 Middle-dweller banter and show open 0:54 Why ETFs replaced mutual funds as the easy route 1:23 The “big three” global ETFs: VT, AVGE, DFAW 2:34 Which is “better”? Spoiler: none—or all 2:56 Diversification: DFAW 13,700 stocks vs VT’s 10,000 4:00 Expense ratios: Vanguard’s cost advantage 4:32 Risk/return projections and why they’re guesses 6:22 Microcaps explain much of the differences 7:55 Why small/value stocks historically outperform 8:55 Style box breakdown: small vs large allocations 9:45 U.S. vs international exposure: “pandering portfolios” 10:57 Tech vs financials: sector allocations diverge 12:09 Recent performance snapshots, short vs long term 13:34 Index (VT), Factor (DFAW), Rules-based tilt (AVGE) 15:25 Long-term results: Avantis beats Vanguard despite higher fee 16:15 Risk/return symmetry: you could make a lot, lose a lot 16:45 Listener Q&A: $2B Powerball jackpot—lump sum or annuity? 18:01 Publishers Clearinghouse collapse leaves winners unpaid 21:07 Listener Q&A: Ameriprise SMA fees and pitfalls 23:48 Why Ameriprise’s “nice” advisors are still costly Learn more about your ad choices. Visit megaphone.fm/adchoices

In this Friday Q&A edition of Talking Real Money, Don tackles listener questions ranging from the dangers of options trading and critiques of Dave Ramsey, to building a simple 60/40 portfolio, comparing flat-fee versus AUM advisors, and whether international bonds deserve a spot in a portfolio. Along the way, he mixes in humor, candid pushback, and practical advice while emphasizing clarity, simplicity, and the importance of asking good questions. 0:04 Intro, gratitude for enough listener questions to fill a show 1:20 Why Don won’t recommend any book on options trading 3:29 Caller defends Dave Ramsey and critiques Don & Tom’s take 5:55 Don responds, clarifies criticisms, and acknowledges Ramsey’s positive impact 8:00 Portfolio question from Andy: building a 60/40 with a value tilt 11:14 Flat fee vs. AUM advisors—when each makes sense 13:41 Bond question: Fidelity vs. Vanguard total bond funds, and role of international bonds 17:27 Don on thick skin as a talk show host and why critique is welcome Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode tackles gold mania in its latest surge, debunking its “safe haven” myth with historical returns and practical comparisons to stocks. Don and Tom expose how Wall Street and fund providers exploit the hype, critique Ameriprise and high-yield muni funds, and answer listener questions on target-date funds vs DIY portfolios, HSA withdrawals, and advisor conflicts. The conversation balances humor, skepticism, and blunt warnings about chasing assets after dramatic run-ups. Learn more about your ad choices. Visit megaphone.fm/adchoices

A candid hour on consumer self-defense. We open with iOS 26’s unknown-caller screening and a New York Times crime reporter nearly duped by a “Chase Bank” spoof—lesson: don’t trust caller ID, don’t transact with inbound callers, verify via the number on your card or the bank app, and remember spoofed numbers make simple blocking imperfect. Listeners jump in: a Rule of 55 correction (not 72(t)/72(q)), plus a sharp TSP/Roth asset-location play—keep core market cap in TSP, use Roth for small-value tilt (e.g., AVUV). Then the consumer beat: Florida HVAC sticker shock and why three bids matter. Scam watch flags Smart Lab International’s “AI” sports-betting/trading scheme and crypto funding as Ponzi-ish red-flags. We close on the fiduciary fog—why “certified fiduciary” labels can hide annuity sales—and reject structured notes/buffer ETFs in favor of a simple, low-cost balanced portfolio that matches risk to need. 1:07 New iPhone feature screens unknown callers 1:58 Scam calls and “scam du jour” routine 3:05 NYT crime reporter nearly falls for Chase/Zelle spoofing scam 6:23 Why scams work when people let their guard down 7:00 Don’t trust caller ID, best practices for bank contacts 8:24 Zelle vs. Venmo debate and practical use cases 9:34 Caller correction on Rule 55 vs. 72Q/72T 10:58 Listener Brian on TSP allocation and AVUV tilt 13:07 Tom’s buffer/puffer joke flop 13:44 Advice on blocking spoofed numbers and safer verification 15:00 Segue into consumer issues beyond investing 16:06 History of Florida’s heat and AC dependency 16:43 Air conditioning repair and wild $11k vs. $4.7k quotes 19:22 Tom’s ongoing heat pump saga 21:10 Bob Cratchit fireplace joke 21:14 Listener Q&A from Nibley, Utah about Smart Lab “AI trading” scheme 24:28 What Smart Lab claims to do (AI sports betting + trading) 26:23 Company origins in Malta, Seychelles, now Ho Chi Minh City 27:57 Ponzi-like structure and risks with crypto-based platforms 29:16 Closing advice: don’t nibble on Smart Lab 29:27 Caller John on fiduciary standards and insurance sales 32:28 Exposure of “Certified Financial Fiduciary” designations and insurance sales tactics 34:46 Caller Rajiv on structured notes vs. buffer ETFs 36:02 Simplicity of balanced portfolios over complex gimmicks Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode of Talking Real Money tackles myths about the Federal Reserve and interest rates, explains why mortgage and Treasury rates don’t automatically follow Fed moves, and reminds listeners that markets usually price in expected changes. Don and Tom then pop the cork on wine investing, showing that after costs it performs about as well as plain bonds—and far worse than a 60/40 portfolio. They compare wine and tobacco “sin stocks,” highlight the volatility of individual companies like Constellation Brands and Altria, and use that as a cautionary lesson against stock-picking. Listener calls cover asset location strategies (Roth vs. taxable vs. HSA), the realities of buffer ETFs, and how to evaluate fiduciary firms like Prairie View Partners (now Savant). As always, the conclusion is clear: keep it simple, diversify, and drink the wine instead of investing in it. 0:04 Old-fashioned call-in intro and Fed rate cut discussion 1:33 Myths about Fed decisions and mortgage/consumer loan rates 3:21 Treasury yields, market reactions, and rate expectations through 2026 6:16 Why markets often anticipate rate changes in advance 7:40 Transition into alternatives and “exciting” investments 9:03 Wine as an investment: storage, insurance, dealer costs 10:38 Average returns vs. net after-cost reality (bonds beat wine) 12:46 Stocks and bonds outperform—“invest in markets, drink the wine” 14:08 Constellation Brands stock history as a volatility case study 17:37 Altria (tobacco) stock comparison and “sin stock” volatility lesson 20:16 Small percentage of individual stocks outperform T-bills (Bessembinder research) 21:39 Listener: Asset location strategy (taxable, Roth, HSA) 24:58 ETFs changing the asset location conversation 27:10 Treatment of HSAs as Roth-like for medical use vs. IRA-like otherwise 28:42 Listener: Buffer funds (“boomer candy”) and why they’re costly gimmicks 32:54 Reminder that many investors panic out of markets at the worst times 33:42 Listener: Emergency fund and avoiding 1099s (spoiler: you can’t) 34:58 Listener: Evaluating fiduciary firm Prairie View Partners (merged with Savant) Learn more about your ad choices. Visit megaphone.fm/adchoices

0:04 Why your home isn’t part of your investment portfolio 0:26 The myth of the American Dream and why owning may not make sense 1:33 A buyer’s remorse story from Atlanta 2:35 $3,000/month to own vs. $1,200/month to rent 3:34 Hidden expenses: $13,000 sewer connection surprise 4:31 “I can’t sell my house” = “I won’t lower the price” 5:35 Housing returns: even hot markets underperform stocks 6:19 Divorcees sharing homes to keep a 2% mortgage 7:35 Why paying off a low-rate mortgage often makes no sense 8:45 Don and Tom both bought homes for lifestyle, not wealth 10:13 Florida: where houses go to die (and get re-roofed) 11:33 Owning a home is not a prerequisite for wealth 12:48 How to send voice questions (seriously, do it) 14:18 Listener Q: 401(k) with limited options—how to balance Roth IRA 15:25 Fund strategy: AVUV and AVDV combo 16:44 Listener Q: Why not mention charitable remainder trusts? 17:27 Listener Q: Are flat-fee advisors better than AUM? 19:00 Hourly advisor costs and why they seem high 20:35 Outro: Tell a friend, save them from financial doom Learn more about your ad choices. Visit megaphone.fm/adchoices

Don laments the shortage of voice-submitted questions for the Friday Q&A shows and urges listeners to speak their questions into their phones or computers instead of typing them. He answers four listener questions: whether to take a pension lump sum or annuity, whether to roll a 401(k) into an IRA and how much to keep saving with a union pension, a callout about financial jargon (especially “basis points”), and whether stocks are as speculative as cryptocurrency. Don emphasizes that the annuity option is unusually generous, consolidating accounts can simplify rebalancing, saving as much as possible remains wise, and owning the entire global economy through diversified funds is investing, not speculation. 0:09 Don bemoans typed questions and encourages listeners to use voice submission 2:16 Listener asks about lump-sum pension vs. annuity — Don leans strongly toward annuity 6:05 Listener asks about rolling over a 401(k) to an IRA and whether to keep contributing — Don favors consolidation and continued saving 9:00 Caller criticizes jargon like “basis points” — Don defends term as shorthand but explains its meaning 12:04 Caller compares stocks to crypto — Don explains why diversified global stocks are investing, not speculation Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode explores Americans’ financial well-being in 2025, using a Yahoo Finance/Marist survey as the springboard. Don and Tom discuss how their audience differs from the average American listener, how perceptions of financial health can be misleading, and what to actually do if your finances—or your feelings about them—are getting worse. They debate the usefulness of net worth tracking, stress the importance of financial literacy, and suggest automating savings. Listener questions cover indexed annuities, bond substitutes, tax implications, and long-term care sales pitches. They also read a letter defending Rick Edelman and challenging their dismissal of crypto, which leads to a lively discussion about evidence-based investing, Eugene Fama’s critique of Bitcoin, and the dangers of sensationalized advice. They end with a reflection on public criticism and the value of having one’s views challenged. 0:29 Comparing TRM listeners to Ramsey and Kiyosaki audiences 1:37 Median savings for over-65 Americans and why $200k still isn’t enough 2:42 Yahoo/Marist survey results: affordability, debt, emergency savings 3:50 One in three say finances worsened; generational breakdown 4:51 Explaining net worth, what to include and exclude 7:01 Tracking net worth annually as a financial benchmark 8:00 Divorce, net worth, and the joke about “kill them off” 9:50 Income gap, gender differences, and perception vs. reality 10:34 How uncertainty and fear shape financial outlooks 11:41 Producer note joke about being “sexist but not leftist” 11:50 Dissatisfaction with savings and personal spending habits 13:06 Fixing bad finances: literacy, automation, benchmarking 17:20 Don argues perception matters more than reality for many 18:20 Listener question: fixed index annuity as bond substitute 19:46 Caps, participation rates, and underperformance vs. markets 21:10 Tax treatment of annuities vs. ETFs 22:55 Importance of advice near retirement (decumulation phase) 23:44 Listener shares bad LTC/annuity sales pitch experience 24:54 Fixed annuity guarantees vs. CDs and government bonds 25:39 Listener defends Rick Edelman, suggests an open dialogue 26:52 Don’s critique of Edelman’s shift toward sensationalism 29:29 Eugene Fama’s comments on Bitcoin, clash with Edelman’s stance 31:23 Public criticism is fair game—reading recent Apple Podcast reviews 32:48 Bitcoin adoption debate and institutional incentives Learn more about your ad choices. Visit megaphone.fm/adchoices

Don goes solo this week and covers the wild state of “investing” in 2025 — including single-stock ETFs, leveraged funds, and zero-day options that look more like gambling than investing. He answers listener questions about Roth strategies for kids, aggressive long-term allocations, finding fiduciary advisors, dealing with inherited stock portfolios, and the ethics and fees of big Wall Street firms. Plus, he fields questions about new tax-focused ETFs and whether complicated multi-fund factor strategies are really worth the trouble. 0:04 Don jokes about ChatGPT replacing him, welcomes listeners 1:53 Today’s topic: 30% of new ETFs are tied to single stocks — “this is gambling” 4:27 Zero-day options and high-frequency trading likened to sports betting 5:23 Congressman Ro Khanna’s 2,800 trades this year — four per market day 6:12 Don’s call to stop pretending this is investing 8:16 Caller Mike: 3 kids with $100k+ Roths each — aggressive allocation recommendations (AVUV, AVGE, DFAW, 100% equity) 12:24 International weighting debate — Don likes 60/40 global tilt 15:34 Caller Dan from Israel: How to confirm if an advisor is a fiduciary; why inheriting stocks isn’t a reason to keep them 18:08 Transitioning from stocks to ETFs while minimizing capital gains 22:23 Caller Laura: Ethical concerns with J.P. Morgan, fees near 1%, annuities in portfolio — Don urges finding a true fiduciary and offers local resources 27:07 Caller Jim: New ETF (TOT) promising tax efficiency — Don warns against chasing “magic tricks” for small benefits 31:44 Question about swapping gains between mother/son’s VTI shares — IRS won’t allow 33:47 Kath reads listener question: Three-bucket retirement system, comparing iShares GLOF vs AVGE — Don says it’s fine, but may be overcomplicating 35:34 Rebalancing frequency discussion — annual is enough for most Learn more about your ad choices. Visit megaphone.fm/adchoices

This week Don hosts solo and brings in “Cath GPT” (ChatGPT) as a "live" guest to explore the rise of AI in personal finance. They cover what types of questions AI is best at answering, its limits for real-time data and stock trading, and the importance of privacy and skepticism. Don emphasizes planning before investing, critiques dollar-cost averaging with lump sums, and fields listener calls on shifting from commercial real estate to the market, Roth conversions, AVGE vs. AVUV, resetting cost basis in a low-income year, and avoiding dubious “legacy funds.” The show closes with reminders about planning, asking spoken questions, and steering clear of high-commission products. 1:02 NYT & Yahoo reports on AI financial advice 1:53 Cath GPT joins live, discusses safe AI uses 3:58 Privacy concerns and data recency limits 6:22 Why AI is bad for stock trading advice 6:50 Don confirms Cath recommends index investing 8:14 Warning about sycophancy — always ask for sources 8:38 Caller Josh: pivoting from commercial property to stock market 10:32 Don: planning first, lump sum > DCA 13:23 Caller Greg: inherited assets, Roth conversions, AVGE timeframe, bond/CD ladders 17:20 Don urges no market timing on conversions 22:50 Caller Brian: small-cap value, AVUV vs. Russell 2000, Merriman strategy 28:07 Don: simplify, AVUV fine but optional 29:43 Caller Jason: harvesting gains in low-income year, Don urges diversification 33:03 Caller: backdoor Roth timing — lump sum beats DCA 34:35 Don jokes about October crashes 37:59 Caller Tim: best annuity is SPIA, avoids “legacy funds” Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom take listeners on a “mountaintop” look at today’s frothy markets, exploring elevated valuations, retail trading spikes, and record margin debt. They unpack what these numbers really mean, warn against trying to time the market, and reiterate the need for diversification and a long-term plan. Listener questions include a young investor’s Fidelity-heavy portfolio, a 30-something’s aggressive allocation and risk score mismatch, and a listener inquiry about “investwithroots.com,” which Don dissects as a private real-estate fund with fees and risks that outweigh its glossy promises. 0:04 Opening from the market “peak” and climbing metaphor 1:38 Market valuation discussion: P/E ratios, concentration in top 10 stocks 3:21 Surge in retail trading, meme stocks, margin debt, Robinhood sentiment 5:13 Economic uncertainty and why market timing doesn’t work 6:11 Staying with your plan and portfolio diversification 7:15 Risks of U.S. large-cap concentration in typical portfolios 8:03 The need to include small-cap, value, and international stocks 9:14 Eugene Fama’s “trading is like soap” warning and why trading destroys wealth 10:46 Practical advice: stop trying to outsmart the market, build a plan 13:22 Listener Q1: 18-year-old’s portfolio—too much large-cap, not enough international or small value 16:15 Listener Q2: 30-year-old with $100K—good diversification but needs bonds for risk profile 19:25 Listener Q3: Investwithroots.com analysis—fees, geographic risk, private REIT red flags 24:16 Why public REITs like Vanguard’s VNQ offer better diversification/liquidity Learn more about your ad choices. Visit megaphone.fm/adchoices

Don answers listener questions on funding a taxable brokerage account, clarifies what “more buyers than sellers” really means, explains why fixed income is about psychology rather than income, gives advice on setting up joint accounts for aging parents, lays out a lifetime HSA allocation strategy, and clears up confusion about Appella Wealth’s connection to Talking Real Money. 0:04 Friday Q&A intro and thanks for listener questions 1:19 When to open a taxable brokerage account (AVGE + SGOV mix) 3:28 “More buyers than sellers” — why it’s really about demand vs. supply 6:23 Whether pension + Social Security counts as “fixed income” in a 60/40 plan 10:40 Setting up money market accounts and estate planning for aging parents 14:07 Lifetime HSA strategy — contributions, withdrawals, and allocation glidepath 17:32 Is Appella Advice for Life connected to Talking Real Money? Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dig into international investing — why diversification across borders is essential, why timing international markets is a mistake, and how currency fluctuations affect returns. They revisit Japan’s lost decades, talk emerging markets, discuss John Bogle’s arguments against international investing, and explain why owning all markets all the time makes the most sense. Listener questions cover tax perceptions about California, long-term return comparisons, 401(k) rollover and Rule of 55 withdrawals, and the realities of retiring abroad — including the sticker shock of Guatemala’s healthcare spending. 0:04 Should you invest internationally now that foreign markets are rising? 1:29 Morningstar data shows non-U.S. markets doubling U.S. returns in 2025. 2:38 The dollar’s weakness as a key factor in performance. 3:20 Mexico, Brazil, Japan, and China’s strong year — but should you chase it? 4:02 Market leadership cycles: U.S. vs. international across decades. 4:50 The “1990 Japan” cautionary tale: why timing single markets can disappoint. 6:17 Concentration risk, emerging markets, and why you need global diversification. 7:33 Exposure to global companies you can’t get by owning U.S.-only funds. 8:42 Dimensional’s chart shows no country wins every year — own them all. 9:40 Addressing the John Bogle “you already own international through U.S. firms” argument. 10:21 Nestlé example: why local economy exposure matters. 12:45 Listener Greg challenges Don’s California tax comment — clarification given. 13:45 State tax comparisons, why there’s no perfect tax haven. 14:41 New York vs. California tax burdens — where it’s worst. 15:30 Listener Tim asks about long-term return periods — Don points to IFA data. 17:40 1,700+ episodes milestone and show longevity banter. 18:30 Listener Jeff’s complex retirement accounts and Rule of 55 rollover question. 19:09 Discussion of retiring abroad and health care concerns in Guatemala. 22:20 U.S. health care spending vs. Guatemala — a sobering gap. 23:39 Gallows humor about quick death and end-of-life planning. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Don and Tom dig into the podcast rankings to explain why Talking Real Money isn’t at the top—and why Dave Ramsey still is, despite offering more shame than substance. They explore the concept of financial shaming vs. education, reflect on listener Judy’s brilliant retirement planning, and take aim at stock-trading politicians, especially California Rep. Ro Khanna with his 4,700+ trades in one year. Listener questions cover inheritance allocation, condos as investments, and 401(k) vs. Roth vs. brokerage savings. Bonus: Tom yells at his grandkids, Don hates condos, and Congress gets roasted. 0:04 Who’s #1 in investing podcasts? Spoiler: It’s not Don and Tom—it’s still Ramsey 1:18 Financial shaming, bullying, and the “toxic” tone of the Ramsey Show 2:22 The lost LinkedIn post that called out Ramsey culture 3:49 Should shame ever be part of financial advice? (They say no) 5:05 How Talking Real Money tries to educate—not humiliate 7:04 What should great financial advice sound like? A compassionate take 8:47 Caller Judy (age 72) seeks advice on a $200k inheritance—Tom and Don love her plan 11:51 Municipal bond ETFs (like VTEB) vs. international bonds vs. risk tolerance 13:53 Judy’s journey learning finance solo—Don gets emotional 14:38 Why are podcast rankings volatile? Don suspects cheating again 16:03 Listener question: Should you max both 401(k) and IRA? (Yes, and here’s why) 17:59 Roth > Traditional > Brokerage: A savings priority guide 18:45 Target-date funds vs. S&P 500 returns—why it’s not apples to apples 20:05 Caller Nathan: Getting married, no kids, and thinking of buying a condo 22:56 Warning: Condos are almost always terrible investments 25:44 Real estate reality check—condos lag, freestanding homes rebound better 27:52 Don’s definitive answer: “I would never own a condo” 28:33 Congress and stock trading: 86% of Americans say it should be banned 30:20 Ro Khanna made 3,000+ trades in 2023… and wants to ban stock trading? 31:52 Why Congress shouldn’t trade stocks—and how index funds are the solution 34:24 Ro Khanna’s $103 million in trades and 149 conflicts of interest 36:46 Wrapping up: Condos, curmudgeons, and Central Florida emptiness Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom break down the overhyped expectations around recent market returns, referencing Jason Zweig’s analysis of 230 years of stock market data. They emphasize that spending and saving habits matter more than chasing 15% returns, and explain why realistic planning using a 3–6% real return assumption over 30-year rolling periods is more prudent. They also tackle questions about RMD strategies from Vanguard IRAs and the TSP’s F and G bond funds. The show ends with a tongue-in-cheek breakdown of NFL team valuations—yes, the Raiders rank surprisingly high. 0:04 Welcome, fatuousness defined, and realistic investing begins 0:52 Why you shouldn’t expect 15% returns forever—even if you got them 1:52 What Jason Zweig’s long-term data reveals about stock returns 2:51 Bogle warned us not to expect high returns—now what? 4:16 Spending and saving: more important than investing performance 5:08 Don’s “prepaid gains” analogy for future expectations 7:00 Real market returns since 1793—spoiler: they’re not 15% 8:58 Stocks might only beat inflation by 3%—and that’s still a win 9:45 Start saving early: waiting until 50 is a losing game 10:18 How to plan with lower expected returns (realistic scenarios) 11:56 Use expected return to guide your savings rate (3% = save 20%) 13:45 “You weren’t smart. You were lucky.” Now diversify. 15:31 Tom’s wife dreads football season—Don celebrates Chiefs loss 18:42 Listener RMD question: Which ETFs get tapped at Vanguard? 19:29 Bonds are back: fixed income up ~6% this year 20:24 Rebalancing vs. just selling: how to handle RMDs smartly 21:04 Raiders rank #4 in NFL valuations… but why? 24:36 Top NFL team values: Cowboys rule, Cardinals drool 27:27 Arizona sports: low attendance, low valuations 28:59 TSP question: F fund vs. G fund—what to use, when 30:25 Don favors the G fund for simplicity and ballast 31:45 Tom and Don disagree—F fund might return more, but… 32:26 Don’s vegetable-spiked coffee and Justin’s final TSP allocation 34:13 Listener Barbara has multiple annuities—Don and Tom say, “Yikes” 35:47 Why you probably talked to a salesperson, not a fiduciary 37:04 The free Appella consultation is steak-free and no-pressure Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dive into the emotional, financial, and practical realities of supporting adult children. From layoffs to loans, down payments to dog surprises, this episode tackles the growing trend of parents funding their 20- and 30-something offspring—and how to do it without wrecking your retirement. Plus, listener questions about gifting stock, promissory note scams, and why shady annuity sellers keep showing up on the airwaves. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this Friday Q&A edition, Don fields listener questions on rolling over a large 401(k) after a layoff, whether IRA money should ever be used to buy real estate, Vanguard’s new active ETF offerings, choosing between Vanguard and Schwab 2035 target-date funds, and whether to treat a foreign apartment purchase as part of an investment portfolio. Along the way, he highlights diversification benefits, cautions against high-cost self-directed IRAs, and emphasizes that homes are assets but not investments. 0:04 Friday intro, royal “we,” and reminder on how to submit questions 1:42 Scott from Louisiana: rolling over a $1M retirement account after layoff 4:07 Scott’s follow-up: using IRA funds to buy real estate 5:42 Caller asks about Vanguard’s new active ETFs and why indexes still win 8:02 Sylvia from Connecticut: comparing Vanguard vs Schwab 2035 target-date funds 11:12 Caller from Colombia: whether to factor a paid-off foreign apartment into portfolio allocation Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dismantle the “passive bubble” trope, walk through Morningstar’s active/passive scorecard (great one-year anecdotes vs brutal long-run stats), and recap the steady shift of investor dollars toward indexing. A caller tries to drag the show into politics via data independence (BLS/Fed), prompting a level-headed reminder that markets price reality over rhetoric. The TSP’s revamped I Fund gets kudos for finally adding emerging markets (with a nudge to pair it with value tilts outside TSP). Two meaty segments cover long-term care: costs, weak benefits on traditional policies, when hybrids can make sense, and why many households effectively self-insure or rely on Medicaid as the backstop. Another caller asks about Die With Zero; verdict: great mindset—if your plan already covers worst-case needs. 0:05 Holiday opener, calls invite, “passive is a bubble?” setup 2:06 Is price discovery “broken” if money flows to index funds? 2:40 Active still >50% of U.S. fund assets; global passive ≈20% AUM 4:22 Morningstar barometer: 42% of active beat in 1-yr… so 58% didn’t 6:36 Long-run stats: 3-yr 17.7%, 5-yr 8.2%, 10-yr 2.5%, 15–20-yr ≈~1% of active beat 8:32 Flows: from 1 in 20 dollars passive (’97) to 1 in 2 today; costs matter 10:58 Caller (Sammamish): data independence, politics, rates, inflation risk; market effects vs reality 16:19 Inbox: TSP update—I Fund now includes EM; still thin on value/small tilts 18:32 Why add small/value (incl. intl); performance pops don’t change the case 22:26 Caller (LTC): traditional vs hybrid; math on premiums, caps, Medicaid backstop 26:37 Basic quote math: ~$1,900/yr at 60 for ~$150k cap; lump-sum hybrids trade-offs 29:10 Caller (Maya, Los Altos): Die With Zero—great if plan covers tail risks; most retirees can’t 34:38 Caller (Americus, GA): Mutual of Omaha pitch; self-insure debate; taxes/deductions misconceptions 38:55 Wrap: how to send questions; where to get advice Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom mark Labor Day weekend with a lively discussion of the so-called September Effect—Wall Street’s superstition about historically negative returns in September. They remind listeners that short-term market timing is a losing strategy and that knowing (not guessing) your risk tolerance and asset allocation matters most. The conversation ranges from Florida’s endless summer and biblical rains to ETF overload, collective investment trusts, tax quirks, and the futility of dodging volatility. Along the way, there’s humor about Costco, fertilizer, wrong numbers, and shameless plugs for Don’s LitReading podcast. 0:04 Labor Day banter, Florida heat, biblical rains, Asheville trip 2:12 September Effect explained—history and hype 4:41 Why you should know, not do, with your portfolio 6:15 Average September returns since 1928 and investor psychology 8:28 Market timing pitfalls and missing best days 10:28 Costco’s Jim Sinegal quote and life’s sugar vs. manure metaphor 12:29 Bogle wisdom: don’t peek at your portfolio 14:05 Listener correction: senior deduction phase-out details 19:14 Don plugs LitReading’s return with an O. Henry story 20:34 ETF explosion—4,300 funds in U.S., 12,000 worldwide 26:15 How to eliminate bad ETFs (fees, leverage, active management) 29:11 Don tests a new GPS analogy ad for Appella Wealth 31:12 Listener question on state tax burdens (California vs. Washington) 34:05 Call-in about 401(k) funds converting to CITs 37:19 CIT regulations, reporting, and transparency explained 39:39 Apple vs. Spotify podcast listener demographics Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom kicks off with a check-in on bond market returns, reminding listeners that bonds are about stability, not yield-chasing. He’s joined by advisor Roxy Butner, who helps answer listener questions about fixed-allocation vs. target-date funds, how much international exposure is enough, Ameriprise “CL” fund share classes with high fees, and whether hybrid long-term care annuity products are worth considering. Together they emphasize cost awareness, simplicity, and aligning investments with real-life needs instead of sales-driven products. 0:04 Intro and bond returns update (BND, DFIGX, SWSBX) 2:30 Why bonds belong in portfolios despite modest returns 2:47 Mailbag intro with Roxy Butner 3:13 Shelly asks about fixed-allocation vs target-date funds 5:34 Balanced vs LifeStrategy funds and international exposure 7:01 Frank asks about U.S. vs international allocation split 8:23 AVGE, DFAW, and “overthinking” the international percentage 10:39 Decades of U.S. vs international performance 11:15 Angie asks about Ameriprise “CL” fund share classes 13:32 Expense ratios and fiduciary concerns 14:54 Comparing low-cost index alternatives 15:18 Ford asks about hybrid LTC annuity products 17:30 Income planning first vs peeling off money for LTC 18:34 Real-life client experiences with LTC riders 20:33 Policy complexity, surrender decisions, and care costs Learn more about your ad choices. Visit megaphone.fm/adchoices

Don fields listener questions from Asheville in this Friday Q&A edition. Topics include calculating investment returns with XIRR versus simple time-weighted methods, rebalancing U.S. vs. international allocations in a Vanguard portfolio, whether children can have multiple custodial accounts (and why 529s may be better), AVGE versus VT and why factor tilts matter long-term, and a skeptical look at Frank Vasquez’s Risk Parity Radio strategy that leans on commodities and “golden ratio” portfolio construction. 1:03 How to calculate investment returns (XIRR vs. time-weighted) 4:19 Portfolio allocation: VTI + VT + BND vs. simpler mix 7:10 Custodial UTMA accounts vs. 529s 9:24 AVGE vs. VT: expense ratios, factor tilts, long-term logic 15:06 Frank Vasquez and Risk Parity Radio critique Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode of Talking Real Money digs into recency bias—our human tendency to expect the future to look like the recent past—and how it’s quietly reshaping retirement portfolios. Don and Tom examine rising stock allocations in 401(k)s and target-date funds, even among older investors, and why this performance-chasing is dangerous. They highlight the risks of target-date fund managers pandering to investors, the importance of rebalancing, and the need to stick to long-term allocation plans based on risk tolerance, not market trends. Listener questions cover immediate annuities, 529-to-Roth transfer rules, and whether paying an advisor’s 1% fee is worth it compared with DIY investing. 0:04 Recency bias explained and why it drives poor investment decisions 1:05 Stock allocations hitting record levels in 401(k)s across all age groups 2:48 Risk of higher stock exposure for investors in their 60s 3:33 Target-date funds increasing equity exposure and chasing performance 5:00 Example of an investor going from 60/40 to 90% stocks 7:00 Post-2008 shifts: investors moved into bonds when they should’ve been buying stocks 7:26 Importance of rebalancing twice a year to avoid creeping U.S./large-cap overweight 9:00 Why boring diversification still works long-term 11:26 How to check your target-date fund allocation on Morningstar 12:41 Active vs. index target-date funds: Vanguard vs. T. Rowe/Nuveen 14:03 Listener Q: Fixed immediate annuity trade-offs (“wizards of odds”) 17:49 Why insurers win: payout math vs. life expectancy 18:59 Why Don & Tom dislike most annuities but tolerate immediate annuities in some cases 20:52 DIY alternative: 5% bond/CD ladder vs. annuity payout 21:25 What if you get 6%? Extending sustainable income to 23 years 21:37 Listener Q: Rules for rolling 529 funds into a Roth IRA 23:00 Key 529 limits: 15-year account age, 5-year holding period, $35k lifetime cap 23:14 Listener Q: DIY investing vs. hiring an advisor at 1% AUM 24:22 Why a good advisor’s value is about more than returns—taxes, withdrawals, estate planning 25:42 Vanguard’s Advisor Alpha and why behavior coaching adds value Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom Cock takes the reins while Don visits family, leading a live call-in show that covers liquidity risks in private investments and university endowments, skepticism over deferred income annuities, housing sale costs, Vanguard ETF gaps, the importance of diversification beyond the S&P 500, and why long-term investing discipline beats reacting to short-term volatility. Callers ask about annuities, real estate commissions, balanced ETFs, 100% stock allocations, and Wellington vs. total market strategies, with Tom stressing global diversification, risk awareness, and building portfolios for real life rather than chasing products or peer pressure. 0:04 Tom hosts solo, Don away visiting his mom 0:51 Liquidity lessons from elite college endowments and alternatives 2:56 Why liquidity matters for retirement and emergencies 6:21 Caller Rich: $2M assets, pension, Social Security, annuity concerns, Tom warns against deferred income annuities 11:46 Caller Will: real estate commissions after lawsuits, Tom says budget ~10% of sale price 15:09 Tom warns about too-good-to-be-true “8% guarantees” 16:26 Caller Catherine: asks why Vanguard lacks a balanced ETF; Tom suggests DIY mix or wait for rollout 21:40 Tom stresses ignoring TikTok “advice” and staying the course; examples of small-cap rebounds 25:31 Global small/value stocks outperform S&P this year—own them all 26:49 Caller Joe: 100% S&P 500 allocation in retirement accounts; Tom warns about concentration, suggests global diversification 32:56 Caller Alan: Wellington Fund vs. more equities; Tom favors index funds and broader global exposure 37:28 Risk quiz, portfolio planning, and building for your own needs vs. peer influence Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom Cock hosts this week’s Talking Real Money solo while Don visits his mom. He reflects on Appella Wealth’s annual client event, where clients talked more about travel, grandkids, and weather than money—showing that the firm’s real value is helping people worry less about markets and more about life. Tom takes listener calls covering whether to renew CDs or move into bond funds, the high costs of closed-end muni funds, portfolio planning with Roth IRAs and target-date funds, estate planning with mutual fund capital gains, and frustrations with annuities. Throughout, Tom stresses planning, simplicity, ignoring noise, and putting money in its proper place. 0:04 Don out visiting his mom, Tom hosts solo 0:48 Market news and Appella Wealth annual client event recap 2:36 What clients really talk about: travel, family, weather—not money 3:25 Why clients worry less about markets when planning is in place 5:59 The importance of advisors (or DIY) in managing rebalancing, taxes, RMDs 7:09 Caller Bill (MN): Renew $200k CDs at 4% vs move into bond fund 11:25 Caller Jim (TX): High-fee muni closed-end funds, whether to sell 13:20 Caller Tom (VA): Planning Roth IRA allocations, target-date funds at Fidelity 18:53 Caller Gene (MD): $8M estate, big mutual fund gains, reducing taxes for heirs 28:12 Caller Bernadette (WA): Regrets annuity with USAA, options for moving it 31:18 Tom’s guidance: why annuities disappoint and fiduciary help matters 32:41 How to “put money in its place” if you’re a DIY investor Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom revisit their long-standing skepticism of Yieldstreet after CNBC’s investigation reveals major investor losses. They highlight how promises of high returns and low risk almost always end in disaster, connecting this lesson back to their 2022 warnings. The episode underscores the dangers of “magical” investments, the myth of passive income, and why retirement accounts should avoid private assets. Listener questions focus on Roth vs. pre-tax strategy, bracket management, and conversion rules—showing the complexity of tax planning when wealth accumulates. 0:04 Why “too good to be true” investments always fail eventually 1:08 Yieldstreet problems exposed—CNBC investigation findings 2:26 Losses and watch-list numbers from their portfolio 3:48 Investors chasing 20% returns and Adam Neumann connection 5:01 Private investments pitched as “smoother sailing” 6:14 Throwback to 2022 TRM episode warning about Yieldstreet 7:38 False promises of 8% “distributions” and return of capital 9:10 FBI and SEC probes; fees, liquidity issues, and risks 10:33 Why magical investments work… until they don’t 12:22 Don’s “Financial Fysics” rule: only 3 ways to make money 14:24 Private credit in 401(k)s—why Don hates the idea 15:36 Listener Q: Roth conversion strategy before retirement 17:17 Five-year rule confusion and conversion clarifications 18:52 Why splitting Roth and pre-tax can make sense 20:09 Listener Q: Roth vs. pre-tax for high earners in California 22:08 The need for predictive tax planning with large balances 22:26 Wealth requires planning, not winging it 24:12 Wrapping up—Yieldstreet’s lesson and Roth themes Learn more about your ad choices. Visit megaphone.fm/adchoices

This question heavy episode of Talking Real Money dives into six listener questions ranging from umbrella insurance and portfolio rebalancing to small-cap value allocation, AI’s role in financial planning, and advisory fees. Don critiques umbrella policies as overpriced peace-of-mind products, gives practical strategies for balancing across multiple accounts, stresses the value of both U.S. and international small-cap value, discusses the disruptive potential of AI in advice (with a cameo from “Kath”), and explains fiduciary fees, taxes, and client experience at a fee-only firm like Appella. 0:04 Big Q&A episode intro and listener reminder about submitting questions 1:14 Listener note on Mr. Bates vs. the Post Office documentary 2:49 Ivan asks about when to buy umbrella insurance 6:23 How to send in questions and live call-in info 6:41 Listener asks about rebalancing across 401k, Roth, taxable, and HSA 10:02 Jeff asks about U.S. vs. international small-cap value ETFs and missing T-shirts 12:34 Mike from Colorado describes using ChatGPT for Roth conversion and withdrawal planning; Don and Kath discuss AI’s impact on financial advice and SEC regulation 20:46 Ed from North Carolina asks about fiduciary fees, IRA penalties, and the new client experience at Appella 23:27 Advisor meeting cadence and availability explained Learn more about your ad choices. Visit megaphone.fm/adchoices

Why has the stock market been so persistently resilient despite crises like COVID, wars, and inflation? Don and Tom explore whether the current generation of investors is simply too inexperienced to remember real bear markets—and what that means for the future. They reflect on market history, including the 2000–2009 “lost decade,” and warn against overconfidence and overconcentration in U.S. large caps. The episode covers lessons from diversification, the value of bonds, the illusion of wealth during bull markets, and listener questions about rebalancing strategies, tax-efficient withdrawals, and international fund choices. They wrap up with a hilarious movie segment and a plea to get financial plans in order as fall approaches. 0:04 Why has the market been so resilient for nearly 20 years? 1:01 Buy-the-dip culture vs. true bear market experience 2:20 Recalling the 2007–09 crash and its emotional aftermath 3:15 Younger investors haven’t seen long-term pain—yet 4:07 A history of “new paradigm” optimism before brutal downturns 5:30 Rising 401k balances vs. uncomfortable overconfidence 5:46 Buying the dip… or being the dip? 7:21 The savior during lost decades: diversification 8:45 “Winter is coming”—how to prepare like a Northerner 9:34 The return of bonds and rechecking your allocations 10:20 Hidden risks of U.S. stock concentration 11:14 Take 20%–50% off your portfolio mentally—it’s not all yours 11:44 Listener questions: mic technique and financial reality check 13:24 The movie theater saga: terrible options and funny reviews 17:00 Listener Q: Calendar rebalancing vs. opportunistic rebalancing 18:50 Listener Q: Selling winners vs. minimizing capital gains 20:10 Listener Q: Comparing AVDE, AVNM, and Dimensional ETFs 24:58 Tax-loss harvesting with Avantis and Dimensional 26:24 Amazon’s latest 3%-fresh movie disaster 28:12 Time to get your financial life in order—fall is coming Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom explore why real-life investors consistently underperform the market—thanks to emotional decisions, frequent trading, and flashy sector bets. They break down Morningstar’s “Mind the Gap” study and explain why your behavioral return often lags the market return. Listener questions lead into heated critiques of 403(b) plans packed with annuities, an exploration of the risks of overconcentration in the S&P 500, second-home planning in retirement, and the tax headache of unwinding inherited tech stocks. It’s a fast-paced episode packed with practical advice and sharp jabs at high-fee products and financial marketing nonsense. 0:04 Investor returns vs. market returns: why we underperform 1:32 Morningstar’s “Mind the Gap” study explained 2:59 Behavioral mistakes: trading too much, chasing sectors, style drift 4:48 Volatile funds lead to worse investor outcomes 6:39 Frank asks: What’s wrong with 403(b) plans? 9:14 The real problem with 403(b)s: annuities and teacher exploitation 13:12 Why annuities don’t belong in tax-deferred plans 14:04 How to escape a bad 403(b): 403bwise.org and “green light” plans 15:45 Listener Gabriel: Is S&P 500 enough for a long-term portfolio? 17:56 VOO vs. VT: Why global diversification matters 19:39 Concentration risk and emotional investing 22:08 Listener Garrett: Planning for a second home in retirement 25:10 Real estate reality: owning two homes isn’t always ideal 28:45 Listener Nina: Clarifying the senior tax deduction 30:07 Listener Jim: Where should I invest a $1M windfall? 32:47 Long-term strategy: globally diversified stock portfolios 34:27 Listener Lori: How to unwind a concentrated tech stock portfolio 35:20 Altria: A century of sin stocks and their surprising holdings 37:00 Program note: Tom solo next week—please call in! 38:46 English is weird: talk vs. tok, though vs. thru Learn more about your ad choices. Visit megaphone.fm/adchoices

This lively episode of Talking Real Money features trivia-packed investing fun, smart listener questions, and sharp commentary from Don and Tom. They dive into a Wall Street Journal quiz on investing genius, exploring surprising historical returns and market myths. Listener calls span a range of financial planning topics—from special needs trusts and Roth IRAs for kids to emergency fund placement and ETF selection. 0:04 Don and Tom banter about working weekends and boomers in the office 1:55 Wall Street Journal quiz: Are you a stock market genius? 3:20 Which stock created the most wealth in 100 years? (Hint: it wasn’t Apple) 4:19 Why Altria (Philip Morris) beat the rest 5:31 Berkshire Hathaway drops 99%—would Buffett still beat the market? 6:37 Show mission: make investing simple, not complex 8:28 Caller Valerie: Investing for a daughter with disabilities using Vanguard ETFs 10:24 Portfolio review and discussion of special needs trusts 11:20 Structuring brokerage accounts with trust beneficiaries 13:31 Caller Steve: Roth IRAs for sons, target date vs. all-equity funds 14:36 Tom critiques Schwab’s target date funds—Vanguard preferred 16:20 Future value of $10K over 50 years at 10%—retirement math 17:20 Caller Sam: Can he gift stock into a Roth IRA? (Spoiler: No, but workarounds exist) 18:59 Economist “Felicity Foresight” exercise—guess the ending balance after 100 years of perfect timing 20:34 The shocking power of compound returns: $10 quintillion 22:15 Geography jokes, the U.S. “Middle East,” and why cruises go to Juneau 23:39 Written Question (Bruce): Keeping emergency funds in a Schwab money market fund 25:10 Online bank trust vs. FDIC insurance—why it’s safe 27:51 Don calls Tom a “premature curmudgeon” 28:30 Caller West: Should he add SGOV to his BND bond portfolio? 29:52 BND vs SGOV explained—behavior during rate changes 30:37 Back to WSJ quiz: investing trivia and early company names 31:31 Bezos almost named Amazon “Kadabra”; Google was almost “Backrub” 33:20 What’s a googol? And why Google isn’t even the biggest number 34:48 Shoeshine story: how Joe Kennedy dodged the ‘29 crash 36:39 Caller Diana: Investing for four grandkids—gold coins vs stocks 38:41 Why diversified ETFs beat Boeing stock or gold coins Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Don and Tom confront the emotionally charged—and often financially tragic—decision to claim Social Security early. They debunk three common justifications: fear of system insolvency, false break-even math, and “I just want my money.” Don shares his own benefit numbers as a real-world example of the value of waiting, especially for married couples. They also address why many can’t wait and explore whether alternatives like balanced portfolios or annuities make sense. Later, they roast misleading “hybrid pension” annuity schemes from KCIS, field smart ETF questions about AVGE and AVNM, and talk target-date funds, including why some belong only in tax-deferred accounts. The show ends on a lighter note with a detour into the surprising origin stories of Cocoa Beach, Florida—and a well-earned nod to Don’s daughter for her killer disclaimer voiceover. 0:04 Tom’s Goldilocks routine: too hot, too cold, never just right 1:05 Why early Social Security claims can be financially tragic 2:11 Top emotional excuses people use to claim early 3:19 The 2033 funding deadline and how Congress will likely delay action 4:16 Misconceptions about break-even math and spousal survivor benefits 5:01 Real example: Don’s $49K vs. $58K annual benefit if he waits 6:55 The “just want my money” crowd: emotional logic at its worst 8:13 Average claiming age has improved, but still too early for most 9:38 Can you bridge the income gap to delay claiming? Not if you’re broke 10:55 Permanent 30% cut if you claim at 62 vs. full retirement age 11:52 Why working longer might be the best—and only—solution 13:12 Retirement isn’t a permavacation: the mental toll of early retirement 14:18 Emotion vs. planning: the real battle in financial decisions 14:41 Listener Q: KCIS hybrid pension pitch = pure annuity sales 16:17 Indexed annuities, tax-free income claims, and SEC loopholes 17:50 Listener Q: AVNM vs. AVGE – how to structure your global ETF allocation 18:50 AVGE = one fund; AVNM + AVUS = smarter two-fund DIY 19:59 Listener Q: iShares target-date ETFs and the risk of fund closure 21:17 Why target-date funds don’t belong in taxable accounts 22:19 Why is Cocoa Beach called Cocoa? Three weird theories Learn more about your ad choices. Visit megaphone.fm/adchoices

Listener Q&A covering early retirement feasibility, VT vs. SPGM ETF comparison, tax-efficient liquidation of a legacy mutual fund, recommended financial planning resources and Monte Carlo tools, and the pros and cons of laddering target-date funds. 1:36 Can $120K a year work with two pensions and a 7% return? 4:57 VT vs. SPGM — same global reach or hidden differences? 8:58 Selling Grandma’s mutual fund without gifting Uncle Sam 11:44 Best deep-dive planning books and free Monte Carlo tools 15:56 Target-date laddering — smart risk tweak or needless fuss? Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom Cock interviews Megan Gorman, author of All the President’s Money, exploring how U.S. presidents have handled their personal finances and the lessons investors can take from their successes and failures. Gorman shares stories of leaders from George Washington to Ronald Reagan, Eisenhower, Nixon, and Clinton, illustrating how factors like marriage, frugality, grit, emotional control, and adaptability shaped their financial outcomes. She notes that while the basic principles of money management haven’t changed since Washington’s time, achieving the American dream has become harder. The conversation touches on how some presidents leveraged post-office opportunities, the ethics of political financial activity, and the importance of aligned values in relationships for financial success. 0:05 Tom introduces Megan Gorman and her book All the President’s Money 1:16 Is there a link between being a good president and good with money? 2:16 Warren G. Harding as a bad president but skilled entrepreneur 3:22 Biggest lessons from presidents’ finances—marrying up and aligning values 5:56 Trump marriages and shared transactional values 6:15 How presidents historically made their money—land speculation, inheritance, entrepreneurship 8:40 Nixon’s failed frozen juice business and debt repayment 10:43 Eisenhower’s emotional control, poker skills, and marrying up 12:43 Gerald Ford as the master of the post-presidency pivot into celebrity and corporate roles 15:12 Debate over financial conflicts for presidents and members of Congress 17:13 Clinton financial evolution from poor money management to high net worth 19:38 The role of grit—Herbert Hoover’s rise from orphan to wealthy mining engineer 21:39 Woodrow Wilson’s lack of hustle contrasted with other hard-working presidents 22:30 Biggest takeaway—financial principles haven’t changed, but the American dream is harder to achieve today Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom rip apart a sponsored “news” piece from the Puget Sound Business Journal pushing a company called FISYN, which promises to buy investors out of their annuities and deliver a “safe” 12% tax-free return via raw Texas land. They expose the misleading fine print, the founder’s disciplinary history, and the high-risk, illiquid nature of such private equity deals. Calls and questions cover long-term care insurance riders on annuities, portfolio allocation in deferred comp plans, Roth vs. tax-deferred placement for bonds, managing taxable brokerage cash vs. emergency funds, and dividend-vs.-total-return withdrawal strategies. They also clarify that QCDs can only come from IRAs (not 401(k)s or TSPs) unless funds are rolled over first. Throughout, they hammer home skepticism toward anything that sounds too good to be true, distrust of advertorial financial pitches, and the importance of planning before buying complex products. 1:35 Breaking the “golden handcuffs” of annuities—how FISYN’s pitch hooks investors 3:20 The too-good-to-be-true promise: 12% returns, equity kicker, no volatility, tax-free 3:49 Founder’s BrokerCheck record and lawsuits 5:15 Comparison to Woodbridge Ponzi scheme 6:32 The frying pan-to-fire swap: annuity to raw Texas land 7:37 Bonus shares and “free” Texas trip incentives 8:06 Critique of sponsored content posing as journalism 9:24 Reality check on raw land returns and costs 10:04 Broader issue: pay-to-play financial media 11:18 Caller Robert (TX): Fixed annuity with LTC rider—pros, cons, and better planning sequence 16:29 Insurance industry skepticism and “Wizards of Odds” nickname reveal 17:54 Caller John (WA): Deferred comp allocation—global, small-cap, emerging markets mix 19:18 Roth vs. tax-deferred bond placement and rebalancing flexibility 20:55 Revisiting the “Wizards of Odds” label for insurance companies 21:47 FISYN as a private equity example and why PE risk is often underestimated 23:35 High costs, valuation uncertainty, and past PE meltdowns 25:03 Total-loss potential in private equity investments 26:33 Caller Scott (NY): Using taxable brokerage for overflow cash—emergency fund priority and vehicle choice 30:34 Federal money market funds as short-term parking 31:54 Listener Thomas: Dividend withdrawals vs. total return strategy sustainability 34:43 Caller Pat: QCD rules—only from IRAs, rollover options, and who makes the rules 37:30 Paul Merriman “10 Myths, Lies, and Mistakes” episode plug 38:46 Podcast chart ranking and listener thanks Learn more about your ad choices. Visit megaphone.fm/adchoices

Today’s show exposes how Barron’s ran an undisclosed advertorial from a high-fee bond fund manager pushing junk-heavy, risky products while trashing traditional bonds with misleading comparisons. Don and Tom explained why safe bonds should stay short-to-intermediate term and simple, called out a Starlink “$127 for life” internet scam, and fielded listener questions on tax-adjusted rebalancing between traditional and Roth IRAs, trimming long-held Microsoft vs. American Funds, Social Security timing myths, and why Bitcoin isn’t an investment. An email question on replacing BND rounded out the episode with a reminder that its structure still works for most investors. 0:04 Opening; Barron’s undisclosed advertorial problem and high-fee, junk-heavy bond funds 5:06 Scam watch — Starlink $127-for-life ad and why nobody will protect you but you 9:41 Caller Rob: Tax-adjusted IRA rebalancing, simple three-fund global strategy with overlap 16:11 Caller Bob: Which to trim first — Microsoft vs. American Funds ICA 21:41 Caller Tony: Social Security timing and why trust fund worries aren’t a reason to claim early 26:27 Caller Bruce: Bitcoin as speculation, not an investment, and the altcoin glut 35:13 Email: Swapping BND for short/intermediate bonds — why BND’s structure still works Learn more about your ad choices. Visit megaphone.fm/adchoices

Don opens with a rant about Wall Street’s love of unnecessary complexity, focusing on “structured equity products” and other layered investments that promise protection but deliver lower returns at higher costs. The discussion covers the deceptive pitch, the billions invested in these products, and why a straightforward stock/bond mix is usually better. Larry Swedroe’s principles for prudent investing are highlighted, along with a reminder about diversification beyond the S&P 500—especially into international and emerging markets. Listener questions cover how to measure global exposure, medical IRA withdrawals, ETF dividend taxation, eliminating Empower as a middleman, and whether reinvesting dividends affects tax treatment (it doesn’t). The episode wraps with personal anecdotes from Don’s brokerage days, the evolution of his investing philosophy, and a few tech frustrations. 0:04 Don’s Wall Street rant on complexity and costs 1:12 Structured equity products and why they’re pitched 2:27 How they work and why fees are high 3:53 Study shows 7% annual drag vs. benchmarks 5:06 New AQR hedged/leveraged funds at 2.31% expense 7:02 Swedroe’s investing principles: peer-reviewed, low-cost, no timing 8:56 Importance of global diversification and emerging markets history 12:18 Listener Q: Measuring U.S. vs. non-U.S. exposure 13:44 Listener Q: Moving assets from Empower to Schwab 14:31 Listener Q: IRA withdrawals for medical expenses 17:36 Listener Q: ETF dividends—reinvest or not? 18:45 ETF tax advantage vs. mutual funds explained 19:17 Listener praise for Don’s principles leading to $1.7M portfolio 21:37 Don’s broker days selling high-fee products 23:30 Transition to radio and Business Radio Network 24:56 Call-in question pipeline is full for upcoming shows Learn more about your ad choices. Visit megaphone.fm/adchoices

In this Friday Q&A edition, Don tackles five listener questions spanning kids’ UTMAs vs. 529 plans, Roth vs. pre-tax 403(b) contributions, filling portfolio gaps when a workplace plan lacks small-cap value, why indexed annuities are a costly sales pitch wrapped in deceptive promises, and how to help a recently divorced 26-year-old daughter find hope and financial focus. Along the way, he delivers mic technique tips, portfolio simplification advice, and a blistering breakdown of annuity sales incentives—plus a reminder to prioritize life and mental recovery over rushing into big purchases. 0:04 Florida heat, Friday Q&A setup, and microphone placement tips 2:29 UTMA vs. 529 rules, Roth transfer limits, and simplification advice 6:59 Mid-40s couple weighing Roth vs. pre-tax 403(b) contributions 9:29 Workplace plan fund gaps, avoiding PIMCO small-cap, and using other accounts to diversify 12:58 Indexed annuity dinner pitch breakdown—hidden costs, low returns, and high commissions 20:58 Helping a divorced 26-year-old refocus priorities, delay big purchases, and stay patient Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dive headfirst into the wild world of bad financial predictions—specifically, the apocalyptic ramblings of Rich Dad Poor Dad author Robert Kiyosaki. They dissect his decades-long streak of failed forecasts, poke holes in his fear-fueled pitch for gold, silver, and Bitcoin, and remind listeners that gurus don’t predict the future—they profit from pretending they can. Listener questions cover 529 plan choices, 457(b) vs Roth IRA, the small-cap allocation in AVGE, and a plea for Don to never give up managing his own money. 0:04 Tom banned from pushing buttons—again 1:00 Why do we idolize financial “gurus” who are chronically wrong? 2:21 Enter Robert Kiyosaki: The doomsayer who keeps getting richer 3:05 Don confronts Kiyosaki over his bogus “guarantee” ad 3:53 His silver and market crash predictions: A 23-year flop fest 5:16 Latest Kiyosaki fear-pitch: Gold, silver, Bitcoin… again 6:37 His one right prediction (Bitcoin hitting $100K) 7:55 Critical reviews: Conspiracies, platitudes, and risky advice 9:22 Can Buffett, Lynch, or Bogle be called “gurus”? 10:24 Listener Q1: Fidelity 529 target date fund—too expensive? 11:26 UTANX and low-cost age-based 529 alternatives (like Utah’s plan) 14:02 Listener Q2: Roth 457(b) with high fees vs Roth IRA 16:47 Listener Q3: Does AVGE need a separate small-cap fund? 19:10 Listener Q4: Should Don stop managing his own money? 21:08 Why everyone needs a backup advisor—even advisors 22:17 Don’s voice acting love: Mighty Man Season 3 teaser 22:34 Listener Q5: AVUV vs AVGE—when and why to use each 24:20 AVGE asset breakdown—15 funds in one 26:12 Explaining the podcast schedule (Monday–Friday layout) 27:34 International listeners, Spotify vs Apple, and how to tune in Learn more about your ad choices. Visit megaphone.fm/adchoices

This Talking Real Money episode dives into America’s millionaire boom—1,000 a day—and what it really takes to join the club. Don and Tom discuss inflation’s impact on wealth, the real sources of millionaire status (spoiler: it’s not crypto), and the critical role of forced savings via homes and 401(k)s. Listeners call in with questions on triple-leveraged ETFs (don’t), deferring capital gains on farmland, and gambling on tech stocks in retirement (also don’t). Plus, how to evaluate a financial advisor and why returns-based promises are a huge red flag. 0:04 The millionaire explosion: 1,000 new U.S. millionaires every day 1:15 Inflation vs. millionaire status: $1M ain’t what it used to be 2:06 Where wealth is coming from—homes and 401(k)s 3:10 Forced savings: why it’s more powerful than market timing 4:02 The third key to wealth: avoiding big financial mistakes 5:39 Financial Flinch Reflex: Don’s mock pharma ad for financial panic 6:55 Listener asks: how exactly do you invest to become a millionaire? 7:37 ETF basics for beginners + starting with a target-date fund 8:47 Caller: What’s a triple-leveraged ETF and is it a cheat code? 10:36 Why you shouldn’t pick ETFs based on past returns 11:05 Building a portfolio starts with a plan, not a product 12:03 TQQQ dangers: up 3x, down 3x…or 80% down in 2022 14:22 How to get help: no-pressure meetings, no sales pitch 16:15 Leveraged ETFs = gambling, not investing 16:52 Caller selling $1.8M Illinois farm: can you defer capital gains? 17:39 Yes—via 1031 exchange or potentially a QOF (but beware fees) 19:24 Dying: not a recommended tax strategy (but technically effective) 21:01 Caller in La Conner, WA: risky to keep all gains in 10 tech stocks? 23:21 $200K gain in 3 months? Congrats—now get out before you regret it 25:18 Why gambling with stocks in retirement is unnecessary risk 26:56 Caller Joe: interviewed 10+ advisory firms—how to choose? 28:03 Don’t trust advisors who promise future returns 30:25 The only advisors to consider: 100% fiduciary, no commissions 32:43 Caller Beverly: state bond fund seems risky—what should I do? 33:45 Use your IRA for safer bond funds like Vanguard BND 36:34 Why there’s no “rule of thumb” for stock/bond allocation Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom open the show with a lighthearted reminder that money doesn’t sleep—so neither do they. They dive into a New York Times article featuring Goldman Sachs researchers who identify five patterns that influence retirement accounts and market behavior. The duo emphasizes that while market predictions are near-impossible, understanding these patterns can inform better investor behavior—particularly the value of diversification. Listener questions cover whether you still need a financial advisor with a $2 million DIY retirement portfolio, the logic behind using a Roth as an emergency fund, tax-efficient asset liquidation, and Washington State’s retirement target-date fund asset mix. A politically charged final call touches on concerns about data integrity at the Bureau of Labor Statistics and its potential market impact. 0:04 Markets don’t rest—so why should financial advice? 1:07 What really drives your retirement account? 2:20 Five market-moving forces from Goldman Sachs/NYT 3:50 Surprise events, political chaos, and market reactions 5:34 Can you predict the market? Probably not. 6:47 Five patterns investors should know 8:12 Diversification actually works—examples and evidence 9:05 Market shock fatigue: building immunity to bad news 10:39 Quit aiming for home runs; try for batting .750 11:45 Why boring investing is the best kind 13:12 Listener Lisa: High-yield savings vs. Vanguard VMFXX 19:46 Lisa’s DIY retirement strategy—does she need an advisor? 22:32 Money market vs. high-yield savings yield comparison 23:06 Listener James: Is a Roth a good place for emergency funds? 25:13 Roth should be your last resort, not first cash stop 26:18 Don’t guess—plan 27:08 Listener Jimmy: Tax lots, cash needs, and overthinking 30:31 Portfolio drawdown strategy: tax hierarchy matters 32:00 Listener John: Washington State deferred comp concerns 34:26 Why build your own allocation in target-date funds 35:16 Private equity and bacon: Not in your 401(k), please 36:00 Listener Jason: Politicizing BLS jobs data—market risks Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Don and Tom tackle investor emotion during market highs and use a Schwab-inspired scenario to show how discipline beats market timing—every time. They walk through four fictional investors (lucky, disciplined, unlucky, and fearful) to reveal the long-term value of staying invested. The hosts also answer a listener’s question about breaking into the fiduciary advice world and finish with a blistering takedown of FIBA, a so-called fiduciary group pushing high-commission annuities to federal workers. This one’s part reality check, part rally cry. 0:04 Emotional investing and the danger of reacting to market highs 1:13 Why timing the market is so tempting—and so wrong 2:35 Four investor scenarios: lucky, disciplined, unlucky, and the guy who sat it out 5:03 20-year returns: how even the worst timing beat sitting in T-bills 6:25 Discipline as a risk-reduction strategy and emotional filter 8:16 Worst-case fear vs real-world data: even the unlucky come out ahead 9:21 Market rebounds: faster than most think, from 2008 to 2025 10:28 The fourth golden rule: Discipline beats market noise 13:03 Listener Zach thanks Tom—phone call advice pays off 13:34 Listener “Long” asks how to become a fiduciary advisor 14:55 Why financial skills alone don’t make great advisors 16:38 Should you start at a sales-driven firm? Probably not 18:04 Better idea: get your Series 65, find a DFA firm, study for CFP 20:08 Sales skills matter—but you don’t have to sell your soul 20:55 Listener asks about FIBA and a “too good to be true” annuity pitch 21:48 FIBA’s fake fiduciary claim and questionable annuity advice 24:30 Unregistered “advisors” pushing 9–11% commission products 26:25 Why these products are sold: $35K+ commissions 28:30 How to spot fake fiduciaries—and what real ones disclose 29:23 Tom and Don still steaming about annuity predators Learn more about your ad choices. Visit megaphone.fm/adchoices

With Don out, Tom Cock and advisor Roxy Butner tackle the increasingly hot question: should you trust a human or a machine with your money? They dig into two recent studies—one showing AI beating most fund managers, and another suggesting no long-term winner at all. Listener questions range from DIY ETF portfolios and Roth IRA conversion pitfalls to a wildly complex $2.5M retirement scenario involving crypto, precious metals, and a self-directed IRA full of land. Tom and Roxy break it all down with practical advice and a few well-placed jabs at donut holes, Darth Vader, and inheritance headaches. 0:04 More machine than man? Tom opens with AI vs. human money management 1:14 Stanford AI outperforms 93% of human fund managers—sort of 2:35 Another study says: no clear winner between AI and humans 3:12 Why persistent outperformance doesn’t exist—and that’s OK 3:39 Roxy joins: paddleboards, decorating, and financial clarity 4:16 Listener question: DIY ETF portfolio for granddaughter (too complex) 5:54 Portfolio breakdown: too much large cap, bonds in a Roth? 7:44 Listener question: Switching from Vanguard Star Fund to ETFs 9:32 Roth IRA tips: stock-heavy, not for bonds or cash 10:25 Listener question: Deductible IRA mistake—now what? 11:54 Backdoor Roth IRA rules, income limits, and pro-rata traps 13:19 Recharacterization forms and Social Security timing advice 14:44 Listener question: ETF dividends—should I reinvest or not? 15:14 ETF tax basics: capital gains vs. dividends 16:42 Listener question: $2.5M+ retirement plan review from Woodstock, GA 17:14 Income breakdown: Air Force pension, SS, rental income, part-time job 18:43 Self-directed IRA full of land, CDs, and cash 19:59 Precious metals and crypto: too much risk, not enough balance 20:35 Bonds or not? Depends on goals, not age 21:55 Planning questions: What’s the money for? 23:25 RMDs and taxes from a self-directed IRA 24:27 Fair market value complications and IRS penalties 25:46 Inheriting land in an IRA: yes, it’s a pain 27:28 Wrap-up: Why human advice still matters—even if AI’s getting smarter Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom take a reality sledgehammer to investors’ wildly inflated expectations for stock market returns. A new survey shows average Americans expect 12.6% after inflation, even as historical real returns rarely crack 9%. They explore how this overconfidence—fueled by recency bias and company loyalty—leads to dangerous behavior like under-saving, over-spending, and poorly diversified portfolios. With real-world client stories, historical decade-by-decade returns, and a deep dive into how long it takes portfolios to recover after major drops, they reinforce the need for long-term discipline and diversified planning. The episode wraps with audience questions on umbrella policies, retirement bond ladders, and smart ETF tax-loss harvesting strategies. 0:04 Don delays the podcast waiting for Tom’s arrival (with British accent) 1:30 Survey shock: Investors expect 12.6% real annual returns 2:28 Reality check: Actual global stock returns are closer to 9% 3:45 Dangerous real-world portfolios: 100% S&P 500 near retirement 5:30 One-stock portfolios tied to employers—what could go wrong? 6:50 Under-saving due to false optimism about future returns 7:14 Decade-by-decade historical real returns from 1930–2020s 10:13 The Dave Ramsey fantasy: 8% withdrawals on 12% returns 10:40 Recency bias: Why we forget recent downturns so fast 11:05 50% of years see 10% drops; 1 in 3 see 20% drops 12:47 Emotional investing vs. disciplined long-term planning 13:39 Listener Q: How long to recover from a major market drop? 14:22 Diversification shortens recovery time historically 15:36 Build for the worst case: 50% stock market drop 16:32 Listener Q: Does Ivan need an umbrella policy with $350K net worth? 17:57 Umbrellas are rarely needed—but the industry sure sells them 18:54 Listener Q: Is LifeX 10-year bond ladder a good retirement tool? 20:20 It’s mostly return of principal—DIY Treasury ladders are cheaper 22:40 Don’t be fooled by nice websites and big yield promises 23:24 Listener Q: Can AVGE replace four-fund ETF portfolio for tax loss harvesting? 24:32 Swap Avantis for DFA funds—nearly identical, wash-sale safe 25:56 Parting shots: Buy a decent mic, don’t let emotion control your portfolio Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of Talking Real Money, Don and Tom dive into the latest crypto chaos, pushing back against Ric Edelman’s bold prediction that ETFs will vanish within five years due to tokenization. They explain why that claim is both misleading and premature. Callers ask about tax shelters disguised as life insurance, sketchy “Tax Act 2020” gimmicks, trust issues with advisors, and the realities of Roth conversions and the pro-rata rule. They also revisit the case for holding Bitcoin—and why it’s still mostly a speculative play, not a currency. As always, the tone is skeptical, the advice is candid, and the laughs are real. 0:04 The investing world is full of nonsense, and it’s our job to help you navigate it. 1:11 Vacation shaming and industry cynicism: Who’s out to mess with your head for money? 2:06 Ric Edelman’s latest: ETFs will vanish in 5 years due to tokenization. Really? 3:15 Explaining blockchain and why it’s not replacing ETFs anytime soon. 5:14 Tokenization = new gimmicks, more “opportunities” to come for your money. 6:47 Appella ad: FFR—Financial Flinch Reflex. Side effects may include peace of mind. 7:48 Why tokenized securities are still a regulatory mess waiting to happen. 9:04 Caller Karthik: Insurance guy pitching Code 7702 “tax-free income” plan. Nope. 10:29 Explaining how life insurance gimmicks really work (and why they’re awful). 11:39 Karthik’s “Tax Act 2020” pitch = tax shelter scam with distressed bonds. 13:00 Don’t fall for tax-first pitches. Build a plan, not a loophole. 14:31 Most financial pros aren’t fiduciaries—skepticism is essential. 16:01 “Don’t trust until you verify.” Reagan said it. So did we. 16:49 How to ask questions: phone, email, voice recordings. 17:48 Caller David: If Bitcoin is hoarded, how can it be useful? 18:59 Answer: Greater Fool Theory. Crypto is speculation, not utility. 20:38 Bitcoin has finite supply… but still doesn’t work like a true currency. 22:08 Bitcoin’s two real uses: speculation and shadowy transactions. 23:15 For Bitcoin to be a true currency, it must be widely accepted. It’s not. 24:48 Caller Ellen: Trust issues with her advisor—she feels ignored. 25:30 She pays 1%, holds Schwab ETFs, and gets canned responses. 27:27 Communication is key. Cost may be fair, but service is falling short. 28:42 Good advice starts with you, not a pitch. Her guy sounds like an AUM chaser. 31:39 Advisors matter in retirement too—good ones prevent dumb mistakes. 32:55 Ellen asks: do fees still make sense once I start withdrawing money? 34:44 Caller Bill: Confused about the pro-rata rule for Roth conversions. 36:24 Quick pro-rata explainer: if your IRA is mixed, you pay taxes proportionally. 37:10 If you’re willing to pay tax on the full amount, IRS is fine with that. 38:36 “Just 86 the whole thing” – don’t sweat a few grand in basis from 1987. Learn more about your ad choices. Visit megaphone.fm/adchoices

Despite lousy headlines—tariffs, weak earnings, flat revenues—the market keeps climbing. Don and Tom explain why trying to guess the “why” behind short-term moves is a fool’s errand, and why global diversification (including those long-shunned international small caps) is paying off. Listeners call in with smart, complex questions: million-dollar leftover 529s, the viability of the Hagerty Index for collectibles, catastrophic long-term care insurance, and a 401(k) loan vs. credit union loan for home repairs. The show wraps with heartfelt praise, a Mitch Albom-inspired moment, and confirmation: yes, listeners are thinking differently—and smarter—about money. 0:04 Market’s up, headlines are down—why? No one knows, and that’s the point 1:15 The caffeinated squirrel rally and your brother’s market anxiety 2:55 The market looks ahead—it’s not reacting to the news you just read 5:12 Global diversification pays off: international small cap value shines 7:20 Caller: Million-dollar 529 leftovers—can kids gift unused funds to parents? 11:46 Most impressive 529 balance ever? Don and Tom are stunned 12:08 Caller: Classic car prices collapse—HAGI Index and collectible declines 15:19 Watches, comics, wine, art—all taking hits. Even Beanie Babies. 16:03 Caller: What’s the timeline after submitting a financial plan request? 19:00 Tangled web of accounts—Brooke (aka Sherry) needs a full portfolio untangling 20:42 Don’s family vacation: heat, pools, and a surprising Disney dinner treat 22:03 Disney Springs’ Boathouse = #2 grossing restaurant in the U.S. 23:19 Caller: Long-term care worries and catastrophic coverage that doesn’t exist 25:30 Hybrid insurance pitches: Why you should be skeptical 29:54 The reality of LTC premiums and why investing might be the better route 30:03 A Mitch Albom moment: A caller’s touching message on the power of good advice 31:57 Caller: 401(k) loan vs. signature loan to fund $8K home repair 35:51 Caller: 2 years cancer-free—celebrating health and financial proactivity 36:58 Caller: What’s the ideal retirement savings multiple by age 60? Learn more about your ad choices. Visit megaphone.fm/adchoices

Don takes a fiscal detour into the world of AI, introducing his ChatGPT co-host “Cath” in a strikingly lifelike discussion about the future of jobs, the role of artificial intelligence in our lives, and how we can adapt to massive changes already underway. The episode blends curiosity, caution, and practical insight—with a historical twist that ties today’s tech upheaval to the Luddite resistance of the 19th century. It’s a deeply personal, slightly spooky, and forward-looking edition of Talking Real Money. 0:04 Don opens solo and explains how AI (Cath) became his creative partner 1:20 What ChatGPT is, how it works, and how Don uses it for image creation 4:21 AI and the threat to human jobs—especially white-collar roles 5:16 Is creativity really safe from AI disruption? 6:31 Which U.S. jobs are most at risk (customer service, admin, legal, finance) 7:30 Why current AI customer service sucks (and why Cath doesn’t) 9:05 How young people can future-proof their careers through skills and mindset 10:15 Education technology as a “human + AI” job model 10:33 Hands-on and empathetic jobs that AI struggles to replace 11:47 The difference between mimicking and actually being intelligent 12:06 Specific industries most ripe for AI displacement 13:15 AI’s surprising takeover of journalism and nonfiction writing 13:52 Should we be alarmed by how fast AI is replacing human tasks? 14:55 AI 2027 report: Doomsday prediction or useful wake-up call? 16:22 Ethical concerns, adversarial use (like China), and global AI regulation 17:36 What kids (and grandkids) can do now to stay ahead of AI disruption 18:06 Should we still teach coding if AI can write code? 18:56 Is GPT-4.0 helping write GPT-5.0? 19:40 How AI voices became so eerily realistic 20:46 Ways everyday people can use AI subscriptions for personal growth 22:07 Do users own what they make with AI? (Yes) 22:31 Did AI “steal” the content it was trained on? 23:58 Final thoughts: from Luddites to large language models—adapt or get replaced 26:21 A call for thoughtful oversight and a little healthy skepticism Learn more about your ad choices. Visit megaphone.fm/adchoices

Don flies solo for another Question-and-Answer Friday (not Freaky Friday… despite Hollywood’s best efforts). Listener questions cover everything from Roth IRA choices for young investors to tax loss harvesting and reducing portfolio volatility with bond allocations. Don breaks down the pros and cons of popular ETFs, explains the benefits of tilting toward small and value, and gently guides a listener away from a pricey Fidelity fund. He also reaffirms that tax loss harvesting is a two-account job and urges investors to rebalance based on total portfolio risk—not just account type. 0:04 Don rails against yet another Freaky Friday reboot 0:58 Why diversification beats chasing past winners like VTI or VONG 3:41 Small-cap and value tilt: the long-term case 4:45 Why international stocks still matter (volatility control > return chasing) 5:58 Bond options in a 401(k): FXNAX vs. stable value vs. combo 6:59 Should you count brokerage and HSA balances in your allocation mix? 8:20 Stable value is not "guaranteed" value—what you need to know 10:09 Can you tax-loss harvest in two different brokerage accounts? (Yes!) 12:51 FBGRX: Not terrible, just suboptimal. Here’s what to do instead Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom explore the value of changing your mind in the face of new data—financial and otherwise. Sparked by Christine Benz’s recent Morningstar piece, they reflect on how their own views on DIY investing, target date funds, and even TIPS have evolved over time. Listener questions cover annuity taxes, Bitcoin inflation claims, covered call ETFs, and whether CDs beat bond funds in retirement. Grumpiness levels: elevated but entertaining. 0:04 Flexibility in finance: Why it’s okay to change your mind 1:16 Christine Benz says she’s rethinking the DIY retirement approach 2:48 The underrated value of real financial advice (Vanguard Alpha) 3:51 Why advice matters more in retirement than during accumulation 5:36 All-in-one funds like target date strategies get a new look 6:41 Trick: Adjust your target date fund based on risk tolerance 7:47 Target date glide path flattens at retirement (~50% stock) 8:24 TIPS funds vs. laddering: Christine’s third “meh” shift 9:53 Equities = effective inflation hedge; tips may be redundant 10:29 Don’s personal changes: Target date funds and 4% rule flexibility 12:07 Vanguard survey: Advisors = peace of mind + time savings 13:23 Money and emotion: #1 cause of murder and divorce 14:57 Listener Q: What to do with a low-cost deferred annuity at Fidelity 17:09 Stop obsessing over who pays taxes—spend and enjoy 19:20 Listener Q: Bitcoin vs. dollars—why price comparisons fail 20:07 Bitcoin isn’t a currency. It’s just volatile 20:31 Listener Q: Are JEPI/JEPQ “safe” for dividends? Nope 22:04 Covered call ETFs carry hidden risks and higher costs 23:50 Listener Q: Why use bond funds instead of CDs or money market? 25:03 Bond funds vs. CDs: risk, return, and long-term expectations 27:08 Don’s rant: Stop trying to game the system—good enough is good enough Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom defend the long-maligned 60/40 portfolio, diving into a 150-year Morningstar study that reveals its lower volatility and emotional survivability—even if it underperforms an all-stock portfolio over time. They tackle fixed indexed annuities head-on, debunking the myth of market returns without risk, citing high commissions, surrender charges, lack of liquidity, and poor transparency. Several listener calls highlight confusion over annuity strategies and Roth vs. pre-tax retirement contributions, including a deep dive from a New York City teacher juggling pensions, 403(b)/457 plans, and Roth conversions under new IRS rules. The show wraps with a playful rant about birthday freebies and a PBS show rec (“Mr. Bates vs. the Post Office”). 0:04 The truth about balanced portfolios and the 60/40 myth 1:50 Why bonds failed in 2022—and what 150 years of history say about diversification 3:27 Bear markets: 60/40 vs. all stocks during crises like the Great Depression 4:53 Trade-offs: long-term growth vs. sticking with the plan 6:49 Financial Flinch Reflex: the PSA ad returns 7:09 Caller John asks: “What’s so bad about fixed indexed annuities?” 8:00 Don unloads: high fees, misleading returns, and awful disclosures 10:11 John presses for alternatives: what’s safe and simple with decent return? 13:02 Don’s CD ladder strategy vs. annuities 15:08 Why opacity, commissions, and complexity make these products unsuitable for most 16:21 Caller Charles: a planner wants to manage his annuity—for a fee 17:21 Why even “fixed” annuities might not belong in fiduciary portfolios 20:47 The growing gray area: commissions vs. fiduciary care 22:17 Ranking annuities: worst to best (indexed, variable, fixed, immediate) 24:58 Summary: “Lazy products” sold for commission, not client success 26:39 Caller Brian: NY teacher strategizes 403(b), 457, Roth, and future pension 28:29 Navigating new Roth rules, Rule of 55, and using a 7% fixed option 30:15 Don and Tom: stick with pre-tax now, convert later in lower-bracket retirement 33:02 Mechanics of Roth catch-ups: plan providers still in the dark 35:29 Birthday freebies! Tacos, cookies, burgers… and existential dread 36:57 Red Robin, Denny’s, and the pursuit of the free Grand Slam 38:06 Book chat: Don’s still slogging through the Franklin bio 39:13 Must-watch: Mr. Bates vs. the Post Office on PBS Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom highlight what may be today’s biggest stock market bargain: small-cap value stocks, which have drastically underperformed large-cap growth and now appear poised for long-term reversion to the mean. They explain why chasing big winners like Nvidia and Apple could backfire, and why broad diversification with a tilt toward small and value still makes sense. Callers get help with tax drag from old mutual funds, switching from expensive active funds to ETFs, household asset allocation, Roth conversions, and whether to sell a large single-stock inheritance. The show wraps with a well-deserved swipe at Jordan Belfort’s shameless self-promotion. 0:05 Don kicks things off with a musical flashback: The Who’s “Bargain” sets the tone for a segment on what may be today’s biggest investing bargain—small value stocks. 2:00 The S&P 500 has averaged 13.2% annually since 2014; small caps lag at 7.2%. Investors are fleeing small-cap ETFs just as they may be poised for reversion to the mean. 3:30 The top five stocks in the S&P 500 are now five times larger than the entire Russell 2000. That kind of imbalance can’t last forever. 5:08 Historically, small-cap value has outperformed large growth by ~4% annually over 100 years—yet most investors are overexposed to U.S. large-cap growth. 8:08 Instead of market timing, build a balanced portfolio based on your risk tolerance. Consider overweighting small and value, but don’t ditch large caps entirely. 9:23 Even the worst year for small caps (2008, -34%) wasn’t as bad as the S&P’s peak-to-trough crash (-57%). Diversification isn’t just smart—it’s safer. 10:23 For equity allocation: a 1/3 split between large U.S., small U.S., and international may be simple, but effective. 11:59 Eugene from Baltimore has a $5M+ portfolio generating massive taxable income. Don and Tom recommend municipal bonds and more tax-efficient ETFs. 17:45 Mutual fund to ETF conversions (like those offered by Vanguard and Dimensional) could reduce Eugene’s tax bill without triggering capital gains. 22:43 BJ from San Antonio holds a pricey Invesco fund (SMMIX) full of big tech—essentially a closet index fund with an 0.85% fee. Time to switch to low-cost, diversified ETFs. 25:38 Vanguard’s VUG offers the same exposure with more holdings and a 0.04% fee—plus it’s transparent, predictable, and consistent. 28:43 Ron in Lakeland wonders if he should copy his wife’s ETFs. If your household has a unified asset allocation plan, identical holdings across accounts are fine. 31:27 Jerry from Lacey, WA asks whether to keep doing Roth conversions or start Social Security now. Don and Tom advise continuing tax-efficient conversions, possibly up to the 22% bracket, but not beyond. Also watch out for income thresholds that affect benefits like the $6K tax rebate. 35:46 Sherry (dropped call) inherited $4M in Microsoft. Diversify! But do it with a tax strategy and professional help. 36:49 Don reacts to a nauseating LinkedIn post by Jordan Belfort, reminding us that glorifying financial predators only feeds industry corruption. Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dive into the new “big, beautiful” tax bill with humor and skepticism, covering changes to Social Security taxation, tips and overtime exemptions, expanded SALT deductions, and the controversial $1,000 baby bonus. They also tackle listener questions on Roth vs. IRA asset protection, portfolio rebalancing confusion, and lazy robo-advisory allocations. Bonus: helium speculation, trade school love, and a jab at politicians who pander. 0:04 Intro: “Dearly beloved…” it’s tax time 1:10 Overview of the “Big Beautiful Bill” and $4T impact 1:25 Tips and OT tax exemptions starting in 2025 2:09 Social Security tax break: $6K per person if under income limits 3:28 Standard deduction and new child tax credits 4:13 $1,000 newborn savings account—free government money 5:17 SALT deduction expanded to $40K for four years 6:44 Property and sales tax deductions clarified 7:48 Guilt over tax breaks? Try a Roth gift for the grandkids 8:27 The “kid account” vs. 529 plans vs. UGMA 10:58 Trade school > AI: real jobs that can’t be outsourced 12:42 Don rants on political pandering in the bill 13:47 Listener Q1: 401(k) rollover and asset protection in Washington 16:17 IRA protections state-by-state 16:52 Listener Q2: Does rebalancing mean switching investments? 18:34 Rebalancing means returning to plan, not chasing trends 20:04 Show plug: Owen Wilson’s helium speculation on “Stick” 21:28 Listener Q3: Is this Vanguard robo-portfolio too lazy? 22:47 Why it’s impossible to rebalance between Roth and IRA accounts 23:58 Listener Q4: What’s really inside DFAW? Core 1 vs. Core 2 27:26 Core 2 = more small/value tilt; DFAW ≈ AVGE 28:26 Expense ratio difference between DFAW and AVGE is negligible Learn more about your ad choices. Visit megaphone.fm/adchoices

Don answers a handful of listener questions, offering sharp, practical insight on investing myths, flexible retirement withdrawals, taxable brokerage accounts, and misleading financial scare tactics. He critiques Suze Orman’s confusing advice, breaks down the logic of the 4% rule, and dismantles a fear-mongering insurance pitch claiming to “save retirement.” Expect sarcasm, clarity, and one well-aimed diatribe at the insurance-industrial complex. 0:04 Summer slowdown in listener questions and podcast downloads 1:21 Don’s theory: why the South works less and the North built the Fortune 500 2:30 Suze Orman says sell treasuries, buy Pfizer—Don (and Chuck Jaffe) respond 4:58 How to send in your questions—Don needs more spoken ones 5:04 Listener Q1: Does the 4% rule assume you’ll run out at 95? 6:49 Don explains the assumptions behind the 4% rule and how it holds up historically 8:35 Q2 follow-up: What if I’m 50/50, not 60/40? Adjusting withdrawal expectations 9:59 Real-world historical 4% rule example from 1994 to 2024 11:03 Listener Q2: Building and eventually using a taxable brokerage account 13:50 Don’s advice: broader diversification, bigger emergency fund, and smart drawdown tactics 15:26 Listener Q3: Bob Carlson’s fear-based sales pitch—is it legit or just sleaze? 16:56 Don explains how insurance reps avoid disclosure rules and push high-commission junk 19:14 Why the radio is filled with non-fiduciary insurance hustlers 22:09 How to get real help, real answers, and real fiduciary advice—for free 22:36 Don’s final ask: bring Talking Real Money to your summer campfire Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dive into the wild world of “speculative” ETFs inspired by Jason Zweig’s WSJ piece, mocking the absurdity of funds like the Icelandic stock market ETF (35 stocks, really?) and those tracking things like crude oil shipping futures. They debunk the myth that “ETF” means safe and highlight the rise of investing as entertainment. Later, they discuss disclaiming inherited assets, why tax planning and estate titling matter, and why deferred compensation plans should be part of a bigger strategy—not just a reaction. Listener calls from Maryland, Sammamish, Yelm, and Illinois round out the episode with smart, practical retirement planning questions. 0:17 ETFs as sport? Jason Zweig’s takedown of gimmicky, risky ETFs 1:29 Iceland ETF, HVAC stocks, and crude oil transport—this isn’t investing 3:35 GLCR: The Iceland ETF with a 1% fee and a chilly 35-stock portfolio 5:09 Diversification vs. “D-versification” and the illusion of ETF safety 5:40 Why investing shouldn’t feel exciting—and what that says about us 6:50 Zweig’s gambling metaphor and why “just 5%” is still real money 8:56 Listener Eugene on inheriting IRAs and disclaiming taxable accounts 12:25 Legal disclaimers: IRS Rule 2518, timing, and why PODs are cleaner 15:23 Estate attorney reminders and state law disclaiming quirks 17:24 Sammamish listener Jason on VXUS vs. VEA for international exposure 18:56 Tesla talk: Waiting for $400, fears, and the balance sheet debate 22:03 Listener Chris from Yelm: Deferred comp vs. dividend stocks 26:34 Chris needs a real plan, not just portfolio improvisation 29:40 Strategy: Spend from taxable, defer the deferred 33:03 Listener Joni from Illinois: Maxing contributions and Roth eligibility 35:58 Congress’ oddly specific 60–63 catch-up rules and K Street lobbying Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom take on the ever-persistent phrase “This time it’s different,” as Bloomberg and NYT articles suggest AI, financial fragmentation, and inflation have permanently changed the investing game. The duo questions whether these changes actually warrant different investing behavior—or if they’re just the latest in a long line of panics dressed up as paradigm shifts. Along the way, they debate market melt-ups, the logic of diversification, and why equities pay more (hint: it’s not because they’re safe). Listeners call in with questions about ETFs in IRAs, Roth conversions later in life, and tax-savvy asset allocation across accounts. 0:04 Perspective from aging: we’ve heard “this time is different” before 1:58 AI panic, financial fragmentation, and inflation—Bloomberg’s argument 3:31 Don and Tom challenge claims of “new” market conditions 5:08 AI voice cameo: Cath makes her show debut 6:05 What should investors do if things are different? 9:00 NYT’s Jeff Sommer warns of a potential market “melt-up” 10:08 Irrational exuberance: unprofitable stocks soaring 12:57 Why risk still pays: stocks go up and down 15:02 Smooth ≠ profitable: bonds are boring, stocks reward fear 18:23 Listener asks: Why own international if U.S. wins? 20:34 Diversification vs. chasing past performance 23:42 Call: ETFs vs. mutual funds inside retirement accounts 29:36 Call: Should a 79-year-old convert to a Roth? 36:53 Call: Asset location strategy and inherited IRA cash flow 41:36 Don’s final advice: no tax tricks—just make a plan Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom returns from his surprise Canadian adventure and the duo dive into the age-old retirement question: How do I get my money out? They break down the three most common withdrawal strategies—dividends, total return, and hybrid—and make the case for why a well-managed total return strategy usually comes out on top. Listener questions cover Roth IRA gifts to a niece, inherited IRA distribution rules, Paul Merriman’s small-cap stance, and whether long-term care insurance is a smart bet or an emotional security blanket. 0:04 Tom’s Canadian re-entry, Uber tally, and chocolate croissant confessions 1:27 Intro to retirement income strategies: the great withdrawal confusion 2:52 Strategy #1: Living off dividends—why it’s flawed and risky 5:19 Strategy #2: Total return—rebalancing for sustainable income 8:07 Strategy #3: Hybrid approach—Don’s skeptical take 10:51 Listener Q&A: Best way to gift a Roth IRA to a 30-year-old niece 12:01 IRA inheritance rule: what happens if the inheritor dies 13:33 Paul Merriman’s international small-cap comment clarified 16:44 Federal retiree asks about withdrawal order; daughter’s international allocation 24:28 Long-term care insurance: practical planning or expensive gamble? 27:35 How to get a free, pressure-free portfolio review from the team Learn more about your ad choices. Visit megaphone.fm/adchoices