Talking Real Money - Investing Talk

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