Talking Real Money - Investing Talk

In this special seasonal episode, you and Tom resurrect Ha or Duh, tearing through Investopedia readers’ “rules to live by” and dismantling the silliest ones with mock gravitas. Between the dad-joke arms race, a spirited defense of compounding, strong opinions on due diligence, and a surprising detour into crypto-mad zip codes, the show blends real financial guidance with holiday-season chaos. The episode also hits deeper listener questions on rebalancing, Roth vs. pre-tax strategy in high brackets, and the danger of thinking blue chips alone equal diversification. 0:04 Seasonal return of Ha or Duh and setup of Investopedia’s “investing rules” 1:32 Rule 1: Never sell because of emotions — duh 2:44 Rule 2: “Only invest in what you know” — emphatic huh 3:35 Rule 3: Good investment in a bad market — phrasing unclear, lean duh 4:26 Rule 4: Never underestimate compounding — mega-duh 5:35 Rule 5: Cash and patience as “positions” — hard huh 6:25 Segment break into calls 7:49 Back to Ha or Duh lightning round 8:33 Buy low, sell high — duh (with caveats) 9:58 “Losses are tuition you won’t get at uni” — pass 10:21 Hold for the long term — duh 11:09 Marathon, not sprint — duh 11:39 Is education the best investment? Nuanced disagreement 12:45 “Always do your own due diligence” — modified duh (about advisors, not stocks) 15:22 FOMO avoidance — duh 16:27 Final rule: Start now — biggest duh of all 17:41 Wrap-up and transition back to regular Q&A 18:06 Listener question: Finding the “sociopath son” episode 19:28 Setup for Friday’s Q&A episode 20:18 Don’s town turns into “free Disney World” during holidays 21:51 Disney hotel pricing shock and personal stories 23:42 Don’s new original Christmas story: Santaverse 24:01 Story podcasts spike; Short Storyverses mention 25:28 Listener from Bothell: 90% blue chips, 10% cash — how to rebalance? 26:39 Why blue chips aren’t diversified and the S&P concentration problem 28:52 Listener in high bracket asks when Roth beats pre-tax 30:26 SECURE Act 2.0 catch-up rules; Roth vs. pre-tax philosophy 32:10 Monte Carlo vs. unknowable future tax rates 33:26 Why all-Roth 401(k)s would simplify life 34:28 Advice: Likely stay pre-tax in 24% bracket 35:50 Shocking stats: Seattle among highest crypto-owning zip codes 37:24 Air Force bases dominate crypto ownership — why it’s dangerous Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Don and Tom saddle up for a tour through Schwab’s “Good, Bad, and Ugly.” They applaud CEO Rick Wurster’s warning about the growing overlap between gambling and investing, take a hard look at Schwab’s retail-side conflicts and non-fiduciary sales practices, and then recoil at the truly ugly: Schwab’s acquisition of Forge Global and its push to open private-company speculation to everyday investors. From there, they field listener questions about crypto’s pointless search for a purpose, how to implement a disciplined 5 percent retirement withdrawal strategy, the ins and outs of tax-free Vanguard mutual-fund-to-ETF conversions, and whether a younger spouse should convert a large TSP balance to Roth. It’s classic Talking Real Money: skeptical, practical, consumer-first, and mildly exhausted by the Wild West of modern finance. 0:04 Investing as the Wild West and why caveat emptor still defines the industry 0:24 Schwab’s role as custodian vs. broker and how they reshaped trading costs 1:14 Schwab’s discount-broker origins and institutional dominance 2:37 Free trades, market influence, and why Schwab became the industry’s leader 3:52 CEO Rick Wurster’s warning about gambling creeping into investing 4:43 Sports betting numbers, prop bets, and why only 5 percent come out ahead 5:54 The “bad”: Schwab retail selling and the fiduciary confusion 6:40 The “ugly”: Schwab buying Forge Global and pushing private-company speculation 7:23 Why private equity is riskier, pricier, illiquid, and over-hyped 8:17 The myth of private companies outperforming public ones 9:22 Why the Wild West persists: weak oversight, self-dealing, and revolving doors 10:48 Listener question: stablecoins, crypto legitimation, and the greater-fool problem 13:00 Currency concerns and why crypto still solves nothing 13:50 5 percent withdrawal strategy: when and how to draw from your portfolio 15:28 Rebalancing, total return withdrawals, and annual cash-flow discipline 16:47 Why withdrawals should follow rebalancing, not lead it 17:56 Vanguard mutual-fund-to-ETF conversions: how they work and why they’re useful 20:10 Expense-ratio savings vs. capital-gains distributions 20:55 TSP-to-Roth conversion question: tax-rate timing matters 22:44 Only convert if you can pay taxes from outside savings 23:08 Reminder: free adviser meetings, no sales pressure 24:10 TRM’s longevity and approaching episode 2,000 Learn more about your ad choices. Visit megaphone.fm/adchoices

This Friday Q&A episode tackles a wide range of listener questions: whether someone with full pension income still needs bonds, how to fix a cluttered 403(b) invested through Corebridge, what to make of Bill Bengen’s new comments about higher withdrawal rates, how inherited IRAs are taxed over the 10-year rule, and a quick explanation of the difference between “securities” and “equities.” Along the way, Don delivers a vintage KOA radio tag, explains why simplicity beats complexity in retirement plans, and walks through why 8% withdrawal fantasies collapse under real-world math. 0:04 Friday Q&A intro and listener call-ins 1:19 Do you need bonds when pensions cover all expenses? 3:01 Why fixed income still matters (and how to gauge risk tolerance) 4:33 Listener request: Don recreates a KOA radio tagline 7:29 A messy CoreBridge 403(b): what funds to keep and how simple it can be 11:37 Target-date vs. multi-fund portfolios and a small value tilt option 12:05 Bill Bengen’s new withdrawal rate comments — does 8% make any sense? 14:07 Why high withdrawal rates implode in historical simulations 16:02 Inherited IRA: what’s actually taxed and how to plan distributions 18:35 The bracket danger of big lump-sum withdrawals 19:31 Final question: difference between a security and an equity 21:15 Why music licensing on podcasts is a nightmare Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode digs into the unwelcome December surprise of capital-gains distributions, especially from actively managed mutual funds. Don and Tom break down Morningstar’s latest list of high-distribution offenders, spotlighting the astonishing 83% capital-gains payout from the Royce Midcap Total Return Fund. They compare the tax drag, costs, turnover, and long-term underperformance of these funds against index funds and ETFs, and explain why tax-efficient investing matters far more than most people realize. Listener questions cover overly complex portfolios, Edward Jones stock positions, odd-lot tender offers, and whether large-cap blue-chip stocks remove the need for bonds. The episode closes with a reminder that detailed portfolio triage is best handled in one-on-one meetings. 0:04 Capital-gains season returns and why high fund returns can still hurt 0:29 Don & Tom on weather, wardrobe, and warming up in Florida 1:30 December capital-gains distributions and why they happen 2:07 Morningstar’s warning: active funds with big capital-gains payouts 3:06 Vanguard, T. Rowe Price, and American Funds distribution levels 4:09 The biggest offender: Royce Midcap Total Return Fund 5:41 Why 35 funds will distribute more than 10% of assets 5:52 The stunning number: Royce’s 83% capital-gains distribution 6:52 Why big outflows and poor performance drive big taxable events 7:21 Royce’s turnover, tiny size, high costs, and weak long-term returns 8:47 Why it’s critical to hold active funds only in tax-advantaged accounts 10:07 ETFs vs mutual funds: tax efficiency and turnover differences 11:42 Comparing Royce to Avantis AVGE on fees, turnover, and performance 12:16 How AVGE tracks its index vs Royce’s massive underperformance 13:33 When selling an active fund before a distribution may or may not help 14:05 Listener question: overly detailed allocation request — why it needs a meeting 16:29 Why some questions require one-on-one analysis 18:20 Why Appella’s free meetings exist (and what they’re not) 20:35 Odd-lot tender offers explained 22:14 Listener: selling Edward Jones stock holdings and leaving EJ 23:42 Why small, young investors should clean up taxable accounts early 24:24 The long decline of commission-based brokerage 25:26 Bothell check-in: blue-chip stocks vs bonds 27:18 Historical returns: 98 years of total market vs small-cap value 28:49 Why bonds exist in a portfolio despite low recent returns 29:30 Closing thoughts on discipline, diversification, and realism Learn more about your ad choices. Visit megaphone.fm/adchoices

A fast, funny Thanksgiving-weekend show where you and Tom unpack why a tiny handful of stocks drive the S&P’s returns, revisit forgotten winners like Hormel and McDonald’s, explain why “you can’t pick them in advance,” and tie it all back to building global, diversified portfolios. Listener calls cover early-retirement withdrawals with 72(t), whether AVGV should replace AVGE, a Thanksgiving relative obsessed with dividends, and a listener being pitched a 1.24% Fidelity “wealth management” upsell. 0:06 Thanksgiving haze, Manhattans, overeating, and setting up the show 2:24 Magnificent 7 vs S&P 493 and how concentrated returns distort hindsight 4:49 1985’s shock winners: Hormel, Lowe’s (the other one), Franklin Resources 7:41 The 1980–1990 decade: Hormel and McDonald’s huge runs and why none were predictable 8:10 Why you need small, value, and international beyond the S&P 500 10:58 Caller: retiring at 56, 72(t) rules, penalties, and whether IRA vs 401(k) location matters 14:28 Correction: SEPP applies only to the chosen account, not all pre-tax assets 16:36 Travel while you can: knees, age, lie-flat flights, and holiday banter 20:21 Caller: AVGE vs AVGV, value tilts, the overlap, and whether it’s worth the swap 22:49 Why AVGV exists (and why advisors may not need it) 27:35 Thanksgiving email: dividend-obsessed relative critiques VXUS payouts 29:53 What dividends really mean—and don’t—and why payout “stability” is useless 35:49 Voicemail: Fidelity wants 1.24% to “manage” half a 401(k); is it worth it? (No.) Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom and Don spend this post-Thanksgiving episode dismantling the illusion that big insurance companies—Northwestern Mutual in particular—are “financial advisors” rather than high-pressure sales organizations built on whole-life commissions. Don recounts his own early days as a Dean Witter cold-call cowboy, and the two walk listeners through a damning Guardian investigation revealing recruitment practices, high-pressure quotas, and the wealth-destroying math behind whole life. The phones open to calls about Cambridge’s nearly 3% wrap fees, sociopathic insurance sales relatives, term-insurance needs for young families, Roth vs. pre-tax decisions, and how to find a real fiduciary advisor. The theme is consistent: avoid sales machines masquerading as advice, and keep investors from being devoured by the industry’s worst incentives. 0:04 Tech glitches, Thanksgiving jokes, and Tom’s three-week vacation cadence 1:45 Why this is “not the best-of”—it may be the worst-of 2:26 Don’s Dean Witter cold-call origin story and the culture of selling, not advising 3:35 Northwestern Mutual’s rebrand and the Guardian investigation 4:08 False promises: “You’ll make $200K in three years” 5:12 The cold-calling boot camp and why only one trainee survived (Don) 6:46 Inside the student recruitment pipeline and the friends-and-family harvesting 8:11 Whole life math: the S&P at +3700% vs. Northwestern at +44% 10:50 Why whole life persists: commissions 12:41 Wrap-up of the Guardian findings and the industry’s structural sleight-of-hand 16:23 CALL: Cambridge Wealth “index” portfolio with hidden fees 23:14 The reveal: Cambridge’s small-account wrap fees approach 3% per year 25:54 CALL: Son-in-law selling insurance, knows it’s a ripoff, loves the money 28:55 Thanksgiving family drama and the “sociopath vs. psychopath” riff 29:59 CALL: How much term life insurance should a high-income parent carry? 32:52 CALL (same): Splitting Roth vs. pre-tax contributions when income is high 34:28 CALL: How to find a true fiduciary (and avoid annuity traps) 37:59 The advisor interview form and how to make salespeople disqualify themselves Learn more about your ad choices. Visit megaphone.fm/adchoices

A light Black Friday edition tackles four listener questions covering Vanguard’s Digital Advisor, the timing of Social Security versus IRA withdrawals, whether to swap target-date funds for a VT/BND mix, and the wisdom (or lack thereof) of adding managed-futures ETFs. The show ends with a look at whether international bonds meaningfully improve diversification (answer: barely). The through-line? Keep investing simple, avoid expensive complexity, and stick with risk-appropriate, broadly diversified portfolios—holiday weekend or not. 0:09 Don debates doing a Black Friday episode but decides to keep listeners company 1:58 How to submit questions on the website and call on Saturdays 2:16 Q1: Is Vanguard’s Digital Advisor worth using? 2:56 Pros and cons: low cost, limited choices, avoid the active-fund version 4:29 Transition to Q2 4:55 Q2: Should a spouse take Social Security at 62 or delay and live off an IRA? 5:50 Pension changes the math—delay for the 8%/yr benefit 7:13 Target-date vs. VT/BND performance and Roth allocation logic 8:32 Risk tolerance matters more than account type 9:09 Actual performance: 2035 fund vs. VT/BND nearly identical 9:42 Q3: Adding managed-futures ETFs as a diversifier 10:23 Why Don strongly opposes adding complexity and high-expense hedges 11:36 Expense ratios make them non-starters 11:56 Q4: Should investors add international bonds? 12:46 Tiny diversification benefit; generally not worth it for DIY investors 14:38 Correlation improvement maxes out around one-tenth of one percent Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom run through a Wall Street Journal list of “subtle signs it might be time to retire,” reacting to each one with their usual mix of disbelief, personal anecdotes, and gentle ribbing. The episode wanders into tech reluctance, job promotions nobody wants, Sunday dread, obsessive 401(k) checking, volunteering guilt, missing peers, feeling left out of friends’ retirements, boss-related misery, and aging knees. They also answer listener questions about Schwab Intelligent Portfolios and their high cash allocations, discuss the shrinking role of physical cash, explain the real value of pre-1964 silver quarters, and handle calls on Social Security math. Tom repeatedly tracks his daughter’s high-school soccer match on-air, providing live updates as the drama unfolds. 1:06 WSJ list of “subtle signs it’s time to retire” begins 1:40 Sign #1: Feeling numb arriving at work 2:11 Why neither host relates to workplace numbness 2:59 Sign #2: Shrinking from new tech tools (Tom jokes incoming) 3:40 Don embraces AI, Tom… less so 4:21 Sign #3: Avoiding promotions; why neither wants a bigger job 5:16 Sign #4: The “Sunday scaries” 5:50 Sign #5: Constantly checking your 401(k) balance 6:26 Mid-list recap before the break 7:42 Second half of the list introduced 8:57 Sign #6: Wanting to volunteer more 9:40 Sign #7: Realizing all your peers have retired 10:11 Don jokes about dying at his desk 11:34 Sign #8: Feeling left out as friends enjoy retirement trips 12:40 Sign #9: Hating your boss (and why that’s not a retirement issue) 12:56 Sign #10: Achy knees and “retire before you can’t enjoy things” 13:35 Doctors, guarantees, and aging joints 14:43 Call for listener questions 15:04 Call: Schwab Intelligent Portfolios’ big cash allocations 16:28 How Schwab makes money on the spread 18:20 Transparency vs. hidden fees 20:20 Back from break — Wednesday podcast explanation 21:31 Don hates change (the coin kind and the life kind) 22:30 Historical buying power of coins 22:56 Pre-1964 silver quarter value 24:15 Odds of finding one in circulation 25:10 What amount of money makes you bend over and pick it up? 25:47 Cleaning out the garage vs. hunting silver coins 27:36 Halftime soccer update: the comeback begins 29:02 Caller: misunderstanding “8% interest” from Social Security discussion 30:26 Caller Paul on cash vs. cashless society 31:51 Coca-Cola prices through time 32:57 Only 12–18% of payments today are cash 34:02 Holiday well-wishes and generational shifts 35:34 Bewitched, credit checks, and pre-internet detective work Learn more about your ad choices. Visit megaphone.fm/adchoices

This episode opens with a warning to younger investors who take TikTok advice over historical perspective, especially around claiming Social Security early. Don and Tom walk through the guaranteed 8%+inflation benefit increase from delaying, why “take it at 62 and invest it” collapses under market reality, and how fear is driving a surge in early claims. They pivot to Bitcoin’s sharp drop and why crypto speculation is driven by greed, not protection, before teasing Don’s upcoming crypto short story. Listener questions cover bad long-term-care/annuity hybrids, overcomplicated “bucket” strategies, responsible portfolio risk, and finally a breakdown of two expensive high-volatility mutual funds—both easily beaten by low-cost index alternatives. 0:04 Message to younger investors about lacking market perspective 1:19 Why TikTok advice on claiming Social Security early is flawed 2:17 The real 8%+inflation annual increase from delaying benefits 2:27 The “take it at 62 and invest it” myth 3:47 Tom recounts Paul Merriman calling his allocation aggressive 4:49 Rising panic-driven Social Security filings 5:21 Don’s 69 vs. 70 claiming decision 6:11 Survivor benefit logic many forget 7:42 Imagining a sudden 30% crash—except it’s Bitcoin 8:29 Bitcoin’s drop from 124K to mid-80s, plus MicroStrategy leverage 9:58 Crypto culture, crypto research, and Don’s upcoming story 10:58 Crypto as a greed play, not protection 12:37 Emotions sabotage investing; the plan removes them 13:51 Why risk needs to match the plan, not ego 15:24 Crypto story teaser + Short Storyverses email plug 16:31 Listener question: NY Life Asset Flex LTC pitch 17:49 Why hybrid LTC/annuity products are weak and commission-heavy 19:47 “Bucket” confusion and the need for purpose 21:30 Caller Eugene: $250K “play money” 23:43 Reality check: could you watch $250K drop to $125K? 24:06 Why timing dips doesn’t work 25:20 Better uses for excess cash in your 70s 27:08 Tom: time for full planning review at age 77 28:38 Fund analysis: Morgan Stanley Growth A 29:25 Fund analysis: Invesco Equity & Income A 30:30 Why moving to low-cost Vanguard indexes is the logical move Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom go deep on a shady “non-profit” financial education group that funnels retirees into high-commission indexed annuities, using a listener tip to unpack the advisor’s fake credentials, mismatched ADV filings, dubious fiduciary claims, and the simple math that reveals where the money really comes from. Along the way, they cover how to investigate advisors yourself, why financial fairy tales persist, and answer listener questions on Avantis gold holdings, private equity’s impact on small-cap value, and the quality of Schwab’s 529 plan. 0:04 Don’s industry rant and a look at the “American Financial Education Alliance” disguise. 1:01 How pseudo-nonprofits target advisors and consumers with “no-sales” sales pitches. 2:20 Tom’s take on the recycled seminar game and fake educator designations. 3:40 Listener tip sparks Don’s PI dive into the flyer, claims, and contradictions. 4:49 How to vet advisors using BrokerCheck and Form ADV. 5:58 The firm’s tiny AUM and impossible economics of their claimed operations. 8:02 The Maryland house vs. the Lakewood Ranch mansion — where the money REALLY comes from. 9:25 The inevitable reveal: indexed annuity commissions driving the whole machine. 10:18 Breaking down the seminar pitch language and the deceptive “market returns without risk” promise. 11:24 Why the sales story collapses under math and dividends. 12:34 The “licensed fiduciary” myth and regulatory reality for small firms. 14:38 How consumers get fooled by the fiduciary framing in seminar mailers. 16:13 Don and Tom dissect the pre-fab radio/TV show factories behind these advisors. 17:19 Why the meeting is the real sales trap — and how to avoid it. 18:48 Don’s plea: stop believing financial fairy tales. 19:26 Don jokes about infiltrating steak-dinner seminars undercover. 20:14 Transition to listener Q&A from Maryland: AVDV’s gold exposure. 21:26 Why Avantis owns gold miners without being “in gold.” 23:47 Momentum, value screens, and why the gold weight makes sense. 24:26 Gold Hill, Oregon 529 question: Is the Schwab plan good? 25:30 Age-based 529s and Schwab’s low-cost structure. 27:28 Private equity fears: will it starve small-cap value indexes? 28:41 Why the concern is mostly a media creation, not an investment reality. 29:48 Don on the IPO–private–IPO cycle and how markets actually work. 30:11 Why private equity performs worse in bad markets. Learn more about your ad choices. Visit megaphone.fm/adchoices

A lively Friday Q&A episode tackling listener questions about FSAs vs. 401(k) contributions, BND vs. BKAG bond funds, intermediate-term bonds vs. CD ladders, Avantis fund-of-funds fees and structure, and the financial implications of New York City’s newly elected socialist mayor. The show blends practical investing guidance with jokes about annuity-salesperson Halloween costumes and a detour into political fears vs. economic realities. 0:04 Opening, Friday Q&A setup, thanks to Tom’s grandkids 0:44 Listener FSA dilemma and choosing between FSA funding or 401k 3:01 Why FSAs are painful and why a 401k wins when choosing one or the other 5:57 Comparing BND and BKAG bond funds, holdings, universe, credit quality 9:01 Listener joke: “scariest Halloween costume is an annuity salesperson” 9:55 Moving CD-ladder money to VGIT or BIV; differences and trade-offs 12:22 Thoughts on iShares LifePath target-date ETF (ITDC) 12:33 Why Avantis fund-of-funds exist and whether you pay double fees 15:36 Underlying fund costs inside AVGE and how the total expense ratio works 16:21 Question about NYC’s new socialist mayor and financial impact fears 17:54 Walking through political fears vs. practical economic reality 21:55 Why one politician can’t radically reshape a city’s economic fate Learn more about your ad choices. Visit megaphone.fm/adchoices

You and Tom spend this episode unpacking a surprisingly liberating idea for investors: that average is good enough. Kicking off with your own story about a two-star podcast rating, you two stumble into a bigger truth—most people are chasing a level of portfolio perfection that doesn’t matter. Christine Benz’s Morningstar piece becomes the backbone of the discussion, contrasting “maximizers” (engineers, tinkerers, over-optimizers) with “satisfizers” (simple, diversified, sane). From there you hit Tesla’s trillion-dollar pay package drama, Bito’s goofy “dividends,” SGOV vs. CD ladders, fears about private equity sneaking into retirement plans, and a few classic Don-and-Tom tangents. The message: stop overthinking, build a sensible portfolio, and go live your life. 0:04 Don’s two-star review existential crisis and the epiphany about doing things for joy 1:16 Why being “average” in investing (and life) is perfectly fine 1:45 Elon Musk compensation debate and ETF shareholders not getting a vote 3:12 Don’s “brilliant raving lunatic” take on Elon and Tesla’s dominance 4:38 The kings of tangentiality finally introduce the show 5:55 Christine Benz and the “Good Enough Portfolio” philosophy 6:36 Maximizers vs. satisfizers explained (plus Bogle bobbleheads) 8:53 Why over-optimization rarely improves results 9:56 Happiness and second-guessing: satisfizers win 11:22 Time costs, tax worries, and the illusion of finding a perfect portfolio 12:33 Two-fund vs. ten-fund portfolios and why simplicity works 13:55 Working harder doesn’t usually make you richer—your job does 14:25 Listener letter: long-time fan from Silverdale reminisces about 1988 15:26 Tom recalls being put on the air after several glasses of wine 16:03 Acorns user asks about BITO’s wild “dividends” 18:10 Why BITO’s payouts are actually return of capital and cannibalization 19:58 BITO’s volatility roller-coaster (standard deviation 53) 20:12 SGOV vs. CD ladders for short-term retirement cash 22:07 Why emergency funds shouldn’t sit in a Roth IRA 22:58 Listener concerned about private equity creeping into 401(k)s 23:52 PE risks, political pressure, and greater-fool concerns 25:27 Don thanks listener “AlwaysLearning1953” for the positive review 26:49 Murder of Crows, sound effects, and the power of scary crows 27:36 New Tales Told update—more stories on the way 28:38 Saturday live show reminder and flyover banter 28:58 Don’s Kansas/Leavenworth childhood story detour Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom open with the investor mistakes Christine Benz highlighted in Morningstar: portfolio sprawl, concentration in the same large-cap tech names, clinging to ancient active funds, ignoring reallocations, and failing at both asset allocation and asset location. The show then shifts into calls—first about fears of an “AI crash,” then a heartbreaking case of an 80-year-old widow stuck in an expensive, incoherent Schwab-built portfolio, which Don dismantles live. Later, Roth conversion strategy, smishing scams, and a closing riff on Bitcoin’s extreme volatility versus gold. A packed episode on how bad habits, high fees, and fear derail investors—and how a simple, globally diversified plan avoids most of it. 0:04 Intro and Christine Benz’s list of common portfolio mistakes 0:56 Portfolio sprawl and “hodgepodge-itis” 1:32 Overloaded baskets of large-cap tech stocks 2:52 The 31-year-old underperforming fund problem 3:54 Active vs. passive: the shift the industry still hasn’t admitted 4:03 Asset allocation errors driven by ignoring the plan 4:51 Why rebalancing matters (and why people never do it) 5:40 Asset location mistakes and why taxes demand a smarter structure 6:15 Why these errors are easy to fix with a simple plan 7:58 Don solo; open phones 8:23 Caller: Fear of an “AI crash” and whether it can tank the market 11:16 Building a portfolio that can withstand any crash 13:01 International ballast and why planning matters more than predictions 14:27 Don solo again; open phones 15:17 Smishing scams and the rise of SMS-based fraud 16:13 How cheap scam-software makes fraud explode 17:08 Caller: 80-year-old widow with an awful Schwab portfolio 18:27 Don investigates the tickers—high fees, obscure funds, bad structure 19:57 Schwab dropped her; Don: “This advisor should be fired” 21:07 Why the portfolio lost money and what those numbers really mean 22:26 Active funds, high turnover, and tax drag 24:01 Don’s verdict: unload the mess and move to simple, low-cost indexing 25:01 Why a target-date fund may be the cleanest fix 26:33 Take the risk quiz; why advisors should be boring 27:00 Don vents about industry incompetence and fee-only failures 28:23 Why advisors chase “exciting” instead of sound 30:02 Caller: Roth conversion when 70% of assets are in traditional IRAs 31:25 Why conversion benefits are minor but sometimes worthwhile 32:33 Strategy: convert up to top of the 24% bracket 33:19 Wrap-up and call for last questions 34:56 Gold vs. Bitcoin: which is actually stable? 36:09 Why Bitcoin’s volatility makes it a terrible “currency” Learn more about your ad choices. Visit megaphone.fm/adchoices

You and Tom take on the myth of hard-and-fast financial rules by walking through Real Simple’s list of nine “rules you can break.” From the latte factor to credit cards, budgeting, bulk shopping, and the old “retire at 65” trope, the conversation keeps coming back to a single theme: money isn’t black and white. You push back against absolutists like Dave Ramsey, emphasize discipline over dogma, and highlight the practical realities of saving behavior, debt, lifestyle choices, and risk. Listener calls round it out — including a thoughtful inheritance question and a late-career investor worried about having “run out of time,” which you defuse with smart, flexible solutions. 0:04 Absolutism vs. nuance in personal finance 1:24 Dave Ramsey’s black-and-white rules 1:57 The latte rule and small vs. big expenses 3:36 Pay-yourself-first as the only rule that really works 4:57 Are credit cards bad? Protection, perks, and pitfalls 6:26 Truth lives between extremes 7:45 “Breakable” money rules from Real Simple 8:39 The myth of retiring at 65 9:59 Why more people work past traditional retirement age 11:00 Don’s TV story and accidental age-compliment 12:59 Is bulk shopping really a money saver? 13:55 Why strict budgets fail 15:04 Tom’s failing FaceTime and tech-phobia 16:02 Caller: leaving money to grandkids who vanished 19:43 Family lawsuits when inheritances differ 20:23 Caller: asset location and bond placement 24:55 Should you draw from 401(k) or IRA first? 28:43 Caller: “Am I out of time to retire?” 33:00 Solving retirement shortfall with portfolio structure 36:16 Don runs the numbers — immediate annuity option Learn more about your ad choices. Visit megaphone.fm/adchoices

A listener’s nightmare 401(k) story sparks a deep dive into how small employers can delay, misuse, or even lose employee retirement contributions before they ever reach the plan custodian. Don and Tom explain the Department of Labor’s weak enforcement, why small plans are most vulnerable, and what workers must do to protect themselves. Then the show tackles backdoor Roth timing rules, Social Security “worst-case” planning, the appeal (or lack of) of mid-cap ETFs, and how to unwind a hodgepodge portfolio without triggering massive tax bills. :04 When employers steal 401(k) contributions before depositing them 1:42 The WSJ case: three-year hunt for missing contributions 3:02 Why small employers are the highest-risk group 5:02 DOL enforcement loopholes and the “administratively feasible” dodge 7:04 What to do if your contributions never show up 8:09 Fidelity bonds, audits, and how recovery really works 9:39 Big-company plans vs. small plans 10:36 Inside the Amazon layoff notice fiasco 11:54 Listener question: timing a backdoor Roth in 2026 for the 2025 tax year 13:40 The Form 8606 trap and pro-rata consequences 15:03 Listener question: Should you assume Social Security cuts in your plan? 16:41 Why benefits probably won’t be cut—even though the system needs fixing 18:04 Listener question: Should anyone buy a mid-cap ETF? 18:46 Why good portfolios already own plenty of mid-caps 19:36 Listener question: Fixing 20 years of hodgepodge-itis at age 72 21:22 Taxes, capital gains, and the slow cleanup strategy 23:52 Why Wellington and Wellesley don’t fit a modern portfolio 25:20 Personal banter: vacations, spending guilt, and sci-fi Learn more about your ad choices. Visit megaphone.fm/adchoices

Don fields a full slate of listener questions on everything from SGOV vs. high-yield savings accounts to the differences between AVUV and DFSV, why international stocks belong in a portfolio (but shouldn’t dominate it), and whether equal-weighted funds solve the “Magnificent 7” concentration problem. He digs into target-date and bond-fund suitability for short-term money, clarifies what “rules-based” really means for Avantis and Dimensional, and gently deflates misconceptions about long-term international outperformance. Along the way he riffs on talk radio’s decline, teases Tom’s dad jokes, and reinforces the core message: diversify, know your time horizons, and don’t overthink what good academic research already tells us. 0:04 Don opens Q&A Friday and reflects on radio’s slow fade 2:20 SGOV vs. high-yield savings accounts for emergency cash 5:13 Why AVUV and DFSV only overlap ~40% despite similar factors 8:43 Which fund is “wilder”: AVUV vs. DFA small value 9:54 Why international stocks belong in a portfolio—but not overweighted 11:41 Long-term U.S. vs. international return history 14:51 S&P 500 concentration and equal-weight ETF considerations 18:44 Equal-weight vs. small-value tilt vs. rules-based funds 20:07 Where to put 2–3 year money: savings, CDs, BND, or a near-dated target-date fund? 23:13 Better language than “active”: rules-based vs. systematic Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom question a surprising Wall Street Journal column arguing that annuities should become the default option in 401(k) plans. They explore why the idea is gaining traction, where the logic breaks down, and how the insurance industry benefits when complexity outpaces understanding. Along the way, they dig into the real shortcomings of annuities—fees, opacity, inflation risk, liquidity traps—and why “guarantees” often mask the true cost. Listener questions follow, covering tax-efficient stock cleanup at Schwab, spouse disagreements over individual stock picking, automatic ETF withdrawals at Vanguard, and building Dimensional portfolios inside Aspire plans. 0:04 Don’s rant: “What the world needs now is… more annuities?” 1:20 WSJ’s argument: make annuities the 401(k) default 2:05 Why income complexity doesn’t justify default annuities 3:01 Do annuities actually solve longevity risk? 3:29 Inflation, joint-life costs, and who really wins 4:20 Insurance industry reputation and the unanswered criticisms 5:15 High fees, opacity, and why mistrust is earned 5:59 Are annuity sales tactics the real barrier? 7:02 Should annuities be in 401(k)s at all? Don vs. Tom 7:36 Why annuities are mostly sold, not bought 9:10 Liquidity traps and major-life-event risks 10:01 Why “plans” matter more than “products” 10:57 Listener questions: why nobody calls anymore 11:14 Q1: Selling a brokerage full of individual stocks at Schwab 12:46 Q1b: How to convince a spouse who loves stock picking 14:21 Indexing vs. anecdotal evidence 16:21 SPIVA data and why active managers lose 17:02 Q2: Can Vanguard automate ETF withdrawals? 19:05 Fractional shares and why purchases are allowed 20:25 Q3: Aspire 403(b) options and DFA overload 23:46 How many DFA funds do you really need? 24:44 Micro-cap risks and portfolio sprawl 25:42 Tom’s pumpkin-patch grandkid cameo Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom and Don grade Gen Z investors from a recent Wall Street Journal article, discussing their portfolios, common mistakes like stock picking, active management, and crypto speculation. They move into practical retirement and college-planning questions from callers — including Roth vs. taxable accounts, 401(k) catch-up contributions, 529 plans, and college costs pushing $90 K a year. 0:04 Gen Z investing habits and media influence 1:59 Grading five young investors from a WSJ profile 7:43 Financial-flinch reflex and planning plug 12:21 Listener: starting a 401(k) at 59 15:34 Listener: using taxable funds for a Roth contribution 20:24 Listener: Roth 401(k) catch-ups and 529 trade-offs 26:08 College costs and saving priorities 28:43 Listener: opening a 529 for a grandchild 36:12 Listener: portfolio check (AVUV + bond ladder) and AVGE recommendation Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom tackle investor “magical thinking,” especially the belief that private equity, non-traded REITs, and other illiquid “exclusive” investments offer hidden superior returns. They walk through Jason Zweig’s recent reporting on a Florida pension fund that locked up money, paid higher fees, and earned under 1% a year. The conversation underscores why liquidity, transparency, and diversification matter far more than complexity or exclusivity. The episode also features listener questions on retirement withdrawal sequencing for a $9M portfolio, evaluating cash balance plans, and deciding between traditional vs. Roth 401(k) contributions. A recurring theme: boring portfolios win. 0:05 Magical thinking and the fantasy of “special” investments 1:52 Private equity realities: higher fees, no liquidity, often lower returns 2:46 The Indian Shores pension fund case 3:44 Withdrawal limits and 0.7% 5-year returns 4:34 Why endowments can do illiquid assets but you probably shouldn’t 5:21 “Roach motel” investing and lack of transparency 8:35 How mutual funds must provide daily liquidity vs. private funds that don’t 8:49 Excitement is bad; investing should be boring 9:54 Caller: $9M portfolio—withdraw taxable first or convert IRAs? 11:51 Traditional IRAs vs taxable sequencing strategy 14:17 Why taxable first lowers tax impact and preserves flexibility 16:03 Blackstone senior housing REIT losses and why “sure things” fail 17:39 Diversification protects you when single bets go bad 18:06 Why private deals appeal emotionally (exclusivity + status) 20:38 Caller: Tesla & concerns about private equity creeping into ETFs 23:07 Why mainstream ETFs won’t adopt illiquid private assets 24:43 REIT ETFs behave more like stabilizing bond substitutes 26:02 LeaveMeAlone email-unsubscribe tool discovery 28:04 Listener questions: send via site or voice form 30:51 Cash balance plan concerns—likely a stable value/insurance product 33:08 Another listener: Edward Jones 401(k) with American Funds C-shares 34:30 High-fee small-plan 401(k)s—why they happen and how to fix 36:27 Caller: Should we switch to Roth 401(k) contributions? Probably not here. Learn more about your ad choices. Visit megaphone.fm/adchoices

Tom welcomes consumer advocate Herb Weisbaum (ConsumerMan) to talk through the rising headaches of modern travel and everyday scams. Herb shares a recent Delta Airlines ordeal where he was nearly stranded overseas because he didn’t have the exact credit card used to purchase his ticket months earlier — a policy he and others say is poorly disclosed and inconsistently enforced. The conversation expands to robocall loan scams, fake toll violation texts, and AI-boosted fraud that’s becoming harder to spot. Herb offers practical steps on how to avoid getting trapped, plus early holiday shopping advice as tariffs and supply issues push prices up. A lively, useful consumer-protection episode. 0:10 Tom introduces Herb Weisbaum and today’s consumer-focused discussion 1:14 Tom’s Heathrow airline mess and why travelers feel powerless 2:08 Herb’s far worse Delta experience: denied boarding without original credit card 3:44 Calling a neighbor at 3am to photograph the card and save the trip 5:13 Delta’s justification: “We’re protecting you from fraud” 6:20 Why airlines can mistreat travelers and get away with it 7:04 U.S. vs. EU passenger rights and compensation differences 8:32 Text scams: fake unpaid toll notices are surging 9:46 The new wave of “pre-approved loan” robocall scams 10:48 AI makes scam messages grammatically perfect and harder to detect 11:04 Slow down, don’t engage, verify before responding 12:20 Let unknown calls go to voicemail to avoid social pressure 14:07 Holiday shopping preview: tariffs, supply constraints, scarcity in decor and toys 15:55 Black Friday all season long—price tracking and refund requests 16:27 Brief detour into kid gifts, backpacks, and questionable plush monsters 17:21 Checkbook.org and ConsumerMan resources for unbiased help 18:17 Herb’s love of model trains and signing off Learn more about your ad choices. Visit megaphone.fm/adchoices