Talking Real Money - Investing Talk

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

Don tackles six listener questions in a rare full-stack Q&A Friday. He breaks down a shady universal life insurance pitch, dismantles the myth of “smart” market timing with limit orders, and offers clarity on Roth conversions, rebalancing strategies, and inherited IRA hacks. A master class in how to stop making dumb money moves. 0:04 Intro – Friday Q&A episode with a goal: 6 questions in one show 1:18 How to ask your questions (and why spoken questions get on air) 2:55 Rachel (NC): Friend sold a $7,000+/yr universal life policy — is it a scam? (Yes) 4:09 Breakdown of how much goes to commissions, costs, and investments in year one 6:44 Better choice: Buy term and invest the difference 8:47 Backdoor Roth IRA Timing: Can I convert a 2025 non-deductible IRA in 2026 and still have it count for 2025? (Sort of, but not really) 11:08 Andrew: Used a limit order during market dip to rebalance — did it work or just get lucky? 14:22 Why timing systems (even “disciplined” ones) fail over time 15:23 S&P 500 Addition Bump: Can you profit from companies added to the index? (Unlikely) 17:37 Tesla example and the dangers of trying to front-run institutional traders 18:22 Casey in Albuquerque: What does rebalancing really mean? (All of it—stocks/bonds, small/large, U.S./intl.) 21:21 Eric: Can you offset inherited IRA RMDs by making IRA/401(k) contributions with that income? (Yes, if within limits) Learn more about your ad choices. Visit megaphone.fm/adchoices

Don is joined by Mike DeJoseph from Vanguard to unpack the meaning and real-world impact of Advisor’s Alpha—Vanguard’s research showing how good financial advisors can add up to 3% annually in net value to client portfolios. They break down the origins of the concept (internally coined back in 2001), clarify what alpha actually means, and dig into where that added value comes from: behavioral coaching, tax-efficient strategies, lower costs, smarter withdrawal planning, and disciplined asset allocation. Mike emphasizes that unlike investment alpha, which is a zero-sum game, advisor alpha is a positive-sum benefit rooted in planning and emotional guidance. They challenge misleading marketing from high-fee brokers, expose the damage of poor advisor behavior, and highlight what separates a “good” advisor from a truly great one—namely, those who align clients’ values with their money. The conversation ends with a forward look at AI’s role in advice: not replacing advisors, but augmenting their ability to listen, guide, and support clients like financial therapists. 0:04 Don introduces rare guest: Mike DeJoseph of Vanguard 0:35 The origin of Vanguard’s Advisor’s Alpha paper 1:27 What is alpha? And what makes it positive for advisors 2:49 Advisor value beyond investment products 3:36 Explaining alpha in terms of benchmarks and behavior 5:05 Why investment alpha is rare, but advisor alpha isn’t 6:25 Positive-sum vs. zero-sum advice outcomes 7:37 Misunderstanding the 3% alpha number 9:48 Behavior, taxes, and cost drag reduce investor returns 11:06 How advisors improve tax allocation and drawdown 11:55 3% does not include asset allocation or manager selection 12:06 Why active manager outperformance remains elusive 13:17 Vanguard’s history with active management and costs 14:45 Active equity vs. active bond management 16:14 What makes an advisor “great,” not just good 17:39 Helping clients align money with values 18:27 Behavioral coaching during market downturns 21:07 Holistic financial advice vs. performance promises 21:47 Why 100% fiduciary advisors are rare—and how to spot one 22:45 Advisor compensation models: from commission to fees 24:06 Shocking stat: commissions down from 80% to 10% since 2010 25:16 How smart investors forced the industry to change 26:44 What a 3% fee does to advisor alpha 28:34 Overcharging kills word-of-mouth trust 29:43 What bad advisor behavior looks like 31:45 Vanguard’s approach to advisor education and ethics 33:41 Where the industry goes next: better advice, better business 34:19 AI’s role in improving advice, not replacing it 36:36 Tech that enhances human connection and insight 37:22 The future: more therapist, less product-seller 37:55 Final advice: if they talk about returns, walk away 38:44 Mike reflects on working with great advisors—and Vanguard’s mission Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom kick off this episode by responding to a one-star Apple Podcast reviewer who promised to upgrade to five stars—if they correct their allegedly false Bitcoin claims. Challenge accepted. Don clarifies his earlier “nobody uses Bitcoin” remark by digging into the actual numbers: only 15,000 businesses worldwide accept it, out of over 359 million—roughly 0.0004%, making it statistically more rare than a lightning strike. They also break down the real costs of converting Bitcoin to dollars: while some exchanges charge under 1%, Bitcoin ATMs routinely charge 5–25% in fees, with total costs sometimes exceeding 30%. Then, a listener calls in with a ChatGPT-generated portfolio featuring VUG, VEA, SMH, and AXON. Don tears it apart for being tech-heavy, overly concentrated, and missing broad market exposure—ironically, even ChatGPT agrees with him. Listeners also get advice on why ETFs are gradually replacing mutual funds, when (if ever) annuities make sense, and why indexed annuities are the financial industry’s version of timeshares: opaque, overpriced, and always sold, never bought. Despite the facts and the humor, Don doubts his five-star redemption is coming—but if Greg’s Mowing and Septic accepts Bitcoin, there’s still hope. 0:26 Don confronts repeat negative podcast reviewers 1:35 NavRep’s public offer: “Correct your Bitcoin lies and I’ll give 5 stars” 2:31 Bitcoin rebuttal: 15,000 businesses accept it—out of 359 million 5:13 Teaser: Bitcoin conversion fees part 2 coming up after the break 6:26 Don admits his imprecise “nobody accepts Bitcoin” claim 8:19 Clearing up the 8% Bitcoin conversion fee claim—context was ATMs 9:49 Bitcoin ATM fees average 17.5%, sometimes hit 30% 11:04 Exchange conversion under 1% is possible—but not for quick cash 13:10 Volatility and impracticality still make Bitcoin a poor currency 16:00 ChatGPT jokes: “Beer at a Baptist wedding” & “Greg the mower” 16:49 Caller Jason asks ChatGPT for a portfolio; Don and Tom cringe 17:46 ChatGPT suggested a tech-heavy, overly concentrated portfolio 20:40 Better suggestions: VT, AVGE, DFAW—not VUG/SMH/AXON 21:50 Don’s GPT criticizes Jason’s GPT: “No bonds, no value, no real estate” 23:43 Caller Scott nails TRM’s philosophy and nearly retires Don 26:12 The rare “pros” of annuities—and their bigger downsides 28:24 Indexed annuities: regular income taxed as ordinary income 30:02 Betting against the house: how annuity math favors insurers 31:44 Caller Jane asks if ETFs are better than mutual funds 32:05 ETF settlement is faster, but that’s not a reason to choose 33:30 Vanguard accounts support ETFs beyond their own funds 34:51 Updated: mutual funds now settle T+1, ETFs also T+1 36:26 Jane warned about National Life Group’s indexed annuity pitch 37:07 Why Don hates indexed annuities: high fees, low returns, opaque structure 39:27 Still selling like hotcakes: $27B in indexed annuities sold Q1 2025 40:35 Wrap-up: annuities remain unethical despite legality and popularity Learn more about your ad choices. Visit megaphone.fm/adchoices