Talking Real Money - Investing Talk

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