Talking Real Money

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

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

In this hard-hitting episode, Don and Tom expose “Retirement Planning University”—a slick, misleading marketing operation posing as a legitimate educational program. Despite hosting seminars at respected universities, the organization isn't accredited and exists primarily to funnel attendees into high-commission indexed annuities sold by Strategic Wealth Investment Group. The duo break down the tangled relationships, the legal gray zones (including a likely violation of Florida law), and the wildly under-disclosed conflicts buried deep in Form ADV filings. Plus: a call from a skeptical listener about global diversification, a backdoor Roth update in response to H.R.1, a heartwarming tribute to Tom's mother-in-law, and a brutal real-world annuity pitch targeting grieving beneficiaries. This one hits hard. 0:04 Thunder and fireworks, then a storm of a different kind: fake financial education 1:20 “Retirement Planning University” is not accredited—possibly illegal in Florida 2:38 Florida law: using “university” in a name can be a crime 4:21 Strategic Wealth Investment Group funnels money into their “nonprofit” 6:27 Don breaks down Form 990 and discovers $6.3M in funding with 1.8% used for education 8:50 A never-before-seen conflict disclosure: over a page of indexed annuity conflicts 11:02 Universities that rent space to these events—should they be ashamed? 13:56 Don confesses: used ChatGPT to surface filings, laws, and charity reports faster 15:40 Final verdict: it's not education—it's a sophisticated lead funnel 17:18 Caller Jack: Is VT too concentrated in tech megacaps like Apple and Nvidia? 19:22 Don: It's still globally diversified, but yes, value/small tilts help 21:57 A heartfelt tribute to Tom's mother-in-law and her one smart money move: LTC insurance 23:01 Caller Mark: Does the new tax bill kill backdoor Roths? 27:18 Don runs the full 900-page bill through GPT—no mention of Roth changes 28:56 Sidebar: elderly elephant tourists and Romanian bear selfies 30:36 Caller Mary: Advisor pitching a 1035 annuity swap to dodge IRMA 34:42 Don and Tom: Just pay the IRMA bump—don't buy another bad annuity 36:44 The IRMA fear is way overblown; it's just one year 39:18 Why aren't these practices banned? Because regulators are stretched thin 40:12 Don taught real adult education classes—but the next “educator” was a broker Learn more about your ad choices. Visit megaphone.fm/adchoices

Is your portfolio built by a broker or a model? Don and Tom break down the surprisingly persistent patterns of old-school broker portfolios—loaded with local stocks, overpriced “index” funds, and actively managed everything—versus the growing adoption of model portfolios based on actual research (not just a hunch and a handshake). Along the way, they torch high-fee index fund imposters, answer smart listener questions on global diversification, CD ladders, tax traps in variable annuities, and even debate whether a Japanese WWII bomber should really be called “Jill.” Oh, and Tom reads a brutal Apple Podcast review… and takes it like a champ. 0:04 Dumb money habits and the rise of model portfolios 1:23 Bellevue vs Florida weather showdown 2:34 Classic broker-built portfolio ingredients 3:55 Sprinkling in overpriced “index” funds 5:50 What a model portfolio is (and isn't) 6:53 Structure vs speculation: why models matter 8:31 Global diversification as a simple model 9:18 The difference between advice and product-pushing 10:24 When “index” doesn't mean cheap: top offender list 11:55 The 2.33% RIDEX fund shame parade 13:02 The Jill bomber sidetrack takes flight 13:54 Listener Laura's AVDE allocation dilemma 15:40 Two-fund model: Avantis U.S. + international 17:00 Logistical pronunciation issues and Bolden software 18:42 Rate assumptions for planning software 19:35 Tom's humor gets roasted in a 5-star review 20:52 Listener Carol's CD ladder tax question 22:38 Timing vs safety: the truth about “dry powder” 24:36 Mitchell's $550K variable annuity dilemma 26:10 Why annuity gains aren't capital gains 27:01 Low-cost annuity, but still no step-up 28:11 The opaque, intentionally confusing nature of insurance 29:41 Scheduling complaints and Don's one-day-off fantasy 32:12 Programming note: no podcast on market holidays 34:04 Calls, questions, and Jill Bomber sign-off chaos Learn more about your ad choices. Visit megaphone.fm/adchoices