• More Questions!
    Mar 6 2026
    This Friday Q&A episode tackles several thoughtful listener questions covering 401(k) investment choices, Roth conversion strategies, bond market fears, inherited IRA planning, and investment club mechanics. Don explains why opaque collective investment trusts and “cycle” funds often hide market-timing strategies, cautions against making large Roth conversions based on predictions about future tax rates, and reassures investors worried about inflation and national debt that markets already incorporate widely known risks. The episode closes with a practical endorsement of a listener’s strategy to gradually withdraw from an inherited IRA to fund Roth contributions, emphasizing simplicity, discipline, and avoiding emotionally driven portfolio decisions. 0:04 Don realizes the intro still says “radio” even though the show is now mostly a podcast. 0:26 Friday Q&A format explained and reminder to submit questions at TalkingRealMoney.com. 1:00 Question 1: 33-year-old with $330k in a 401(k) invested in opaque “intermediate cycle” and wealth-preservation funds. 2:26 Don explains collective investment trusts (CITs) and why their lack of transparency is problematic. 5:25 Market-timing strategies disguised as “cycle” funds and why simple equity funds may be better. 6:47 Question 2: Listener corrects earlier discussion about transferring securities from investment clubs. 8:37 How in-kind transfers can avoid capital gains when leaving an investment club—depending on club rules and brokerage policies. 10:31 Question 3: Complex Roth conversion strategy involving IRMAA tiers and future tax assumptions. 14:31 Don warns against making large conversions based on predictions about future tax rates. 16:07 Why gradual conversions preserve flexibility compared with large upfront tax bets. 17:28 Question 4: Concern about national debt and whether to replace BND with VTIP (TIPS). 18:56 Don argues markets already price known risks like debt and inflation expectations. 20:11 How TIPS work and when they actually help investors. 21:46 Reminder that emotional reactions to economic fears often lead to bad portfolio decisions. 22:10 Question 5: Using withdrawals from an inherited IRA to fund Roth IRA contributions. 22:52 Strategy: withdraw gradually to fund Roth contributions while staying within tax brackets. 24:15 Don endorses the plan as simple, tax-efficient, and compliant with the 10-year inherited IRA rule. 25:09 Closing comments and reminder to submit questions. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    23 mins
  • Exchange Traded Gambling
    Mar 16 2026
    Exchange-traded funds began as simple, low-cost index vehicles, but their popularity has sparked a flood of increasingly speculative products. Don and Tom explain how more than 1,000 new ETFs launched in the past year—many involving leverage, crypto exposure, or even single-stock bets—turning what was once a sensible investment wrapper into a playground for risky financial engineering. They discuss why firms are rushing into ETFs to capture investor dollars, how leveraged products can devastate portfolios, and why investors must focus on what’s inside an ETF rather than the label itself. The episode also answers listener questions about the cost structure of Avantis’s AVGE fund-of-fund ETF, strategies for gradually escaping tax-inefficient mutual funds like American Funds, and the rules governing cost-basis transfers when moving brokerage accounts. 0:04 ETFs used to be simple—now Wall Street is turning them into gambling products 1:24 Explosion of new ETFs: 1,000 launched in a year and most offer nothing new 3:07 Why firms are rushing into ETFs: chasing the $1.5 trillion flowing into them 4:23 Leveraged crypto ETFs (like 2× Dogecoin) and how investors lost 70% quickly 6:15 Greed, leverage, and investor behavior driving risky ETF products 7:48 The absurd rise of single-stock ETFs—paying fees to own one stock 8:55 Leveraged commodity ETFs and the danger of massive one-day losses 9:45 Margin speculation and the historical lesson of the 1929 crash 10:31 An ETF is just a wrapper—what’s inside determines whether it’s sensible 11:51 Simple rule: avoid ETFs charging more than about 0.35% annually 12:08 Using Morningstar to check ETF costs and holdings 14:26 AVGE question: how fund-of-fund ETF expenses actually work 16:47 Escaping tax-inefficient mutual funds like American Funds 19:56 Capital Group’s ETF strategy vs traditional loaded mutual funds 22:28 Cost basis rules when transferring accounts between custodians Learn more about your ad choices. Visit megaphone.fm/adchoices
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    31 mins
  • Questions Four
    Mar 13 2026
    In this Friday Q&A episode, Don answers four listener questions covering fund recommendations, special-needs financial planning, retirement withdrawal strategy, and tax-efficient health savings. First, he addresses whether Talking Real Money receives commissions for mentioning Avantis and Dimensional funds (they do not) and explains why those firms’ evidence-based strategies stand out. A second caller asks about planning for a child with a lifelong disability, prompting Don to stress the importance of working with a specialist attorney to establish structures such as special-needs trusts and ABLE accounts. Another listener questions whether all-in-one funds complicate retirement withdrawals, but Don argues that simple portfolio withdrawals beat complex optimization strategies. The episode closes with a teacher nearing retirement asking whether drawing from a 457 plan to keep funding an HSA is worthwhile, which Don notes can create a powerful tax advantage similar to a Roth conversion. 0:05 Friday Q&A intro and reminder to submit voice questions at TalkingRealMoney.com 0:50 Listener asks whether Don and Tom receive commissions for recommending Avantis or Dimensional funds 1:33 Don explains the evidence-based origins of Dimensional and Avantis and confirms there are no commissions or compensation 4:15 Caller asks how to financially plan for a child with a lifelong neurological disability 5:15 Don stresses the importance of working with a special-needs attorney and explains tools like ABLE accounts and special-needs trusts 7:09 Listener asks whether all-in-one funds like VT or AVGE create problems when withdrawing money in retirement 8:27 Don argues simplicity is better than optimization and recommends withdrawing from the portfolio as a whole rather than trying to pick winners 10:49 Teacher retiring at 54 asks whether it makes sense to withdraw from a 457 plan to continue maximizing HSA contributions 12:38 Don explains how using taxable withdrawals to fund an HSA can effectively create a Roth-like tax benefit Learn more about your ad choices. Visit megaphone.fm/adchoices
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    18 mins
  • Don't Invest?
    Mar 12 2026
    A debate over jelly bean flavors quickly pivots into a takedown of a flashy Inc. Magazine article claiming people shouldn’t save for retirement. Don and Tom dissect the “cash-flow over investing” pitch from entrepreneur Joseph Drups, exposing the realities of running small businesses, the risks behind claims of passive income, and the likelihood that the real money comes from selling the system rather than executing it. The conversation then turns to listener questions, including the differences between Avantis ETFs AVGE and AVTM and a thoughtful inquiry about whether factor investing from firms like Avantis and Dimensional justifies higher fees compared with traditional cap-weighted index funds. 0:04 Jelly bean debate returns: Costco Jelly Belly flavors, jalapeño surprises, and the “Pepto-Bismol” mystery bean 1:58 Inc. article claims you shouldn’t save for retirement 2:45 Entrepreneur Joseph Drups’ “cash-flow over investing” strategy 4:08 The myth of passive income from small businesses 5:46 Valuing a business vs. claiming low net worth 7:17 Reality check: most small businesses fail 10:06 Drups Ventures model and e-commerce brand acquisitions 11:10 The $100/month “Fast FI Club” and selling the system 13:55 Entrepreneurship vs. unrealistic promises of passive income 15:28 Impatience and the risks of chasing quick financial independence 16:44 Listener question: Avantis AVTM vs. AVGE 19:11 What actually defines a “true” index fund 23:06 Bogleheads critique of smart beta and factor strategies 24:08 Evidence for small-cap and value premiums since 1926 27:18 Fees vs. expected factor premiums 28:00 Recency bias and long periods when factors underperform 30:53 Raisin Bran bag conspiracy theory and aging complaints Learn more about your ad choices. Visit megaphone.fm/adchoices
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    36 mins
  • Retiremeet 2026 Part Two
    Mar 11 2026
    Broadcast from RetireMeet 2026 in Bellevue, Don and Tom reflect on the evolution of retirement planning—from a narrow focus on investments to a broader conversation about purpose, relationships, and life after work. They interview Paul Merriman, who discusses portfolio construction, the role of small-cap value stocks, risk tolerance, and long-term investing discipline. The conversation also explores withdrawal strategies, market history, and how investor behavior during downturns often determines success more than asset allocation itself. The episode closes with a major announcement: the Talking Real Money radio show will end in April and transition fully to a podcast format with five weekly episodes. 0:27 Reflections on the event and praise for speakers like Christine Benz and Paul Merriman. 1:54 Growing focus on purpose and lifestyle in retirement, not just money. 3:11 Audience turnout and attendees traveling from across the country for RetireMeet. 3:51 The importance of a holistic approach to retirement planning including relationships and lifestyle. 5:25 Estate planning conversation and the uncomfortable reality of thinking about life after we’re gone. 6:01 How to listen to the podcast and transition from radio listening to podcast apps. 6:41 Introduction of Paul Merriman and discussion of portfolio construction and asset classes. 8:15 Understanding risk tolerance and balancing portfolios for different ages. 9:41 Investor behavior during crises like 2008 and the tech crash of 2000–2002. 10:32 Cap-weighted vs equal-weighted S&P 500 and tax implications. 11:48 Why investors should document how they feel during market highs and lows. 12:06 Using nearly 100 years of market data to understand future volatility. 14:42 The evolution of financial planning from investment management to comprehensive planning. 16:19 Financial education gaps and rising bankruptcy rates among retirees. 18:00 Debate over whether 401(k)s replaced pensions successfully. 20:52 Merriman explains small-cap value investing and why unpopular stocks can outperform. 23:12 Why most investors don’t hold small-cap value despite historical advantages. 26:11 Long-term investing and the importance of patience through underperformance cycles. 28:24 Withdrawal strategy research showing dramatic compounding over long periods. 30:05 Whether future market returns can resemble historical returns. 31:41 The danger of reacting to news headlines and wars when investing. 33:52 Talking Real Money radio show ends in April and shifts to a podcast-only format with five episodes weekly. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    38 mins
  • Retiremeet 2026 Part One
    Mar 10 2026
    Broadcast live from RetireMeet in Bellevue, Don announces that after nearly four decades of Saturday radio shows, Talking Real Money will end its live radio run on March 28 and continue exclusively as a podcast. The episode features conversations with Joe Saul-Sehy of Stacking Benjamins and Morningstar’s Christine Benz about how people should approach retirement. The central theme is flipping the traditional process: design the life first and the money second. Guests emphasize “play-testing” retirement activities before leaving work, gradually transitioning into retirement rather than stopping abruptly, maintaining strong social connections, and keeping purposeful work or learning in later life. The discussion closes with Benz’s practical financial steps for retirement planning, including tracking spending, accounting for Social Security and pensions, and using flexible withdrawal strategies supported by fiduciary advice. 0:04 Live broadcast from RetireMeet in Bellevue and show introduction 2:58 Don announces the end of the Saturday live radio show after nearly 40 years 3:59 Transition to a podcast-only format beginning in April 4:43 How listeners can switch to listening via podcast apps or the website 6:41 Introduction of Stacking Benjamins host Joe Saul-Sehy 8:09 Discussion of Stacking Benjamins community meetup groups 9:25 Trivia detour about the $500 bill featuring William McKinley 9:36 Joe’s retirement philosophy: design the life first, then the financial plan 10:56 “Begin with the end in mind” when planning retirement 11:23 The concept of “play-testing” retirement activities before retiring 13:51 Warning about AI impersonation podcasts and fake financial shows 15:20 Joe Saul-Sehy’s career change after selling his advisory firm 16:37 Discovering a passion for teaching about money through media 17:33 Continuing meaningful work rather than fully retiring 18:07 Humor about a future podcast called “Two Old White Guys Waiting to Die” 18:48 Core message: experiment with retirement interests now 19:38 Christine Benz of Morningstar joins the conversation 21:04 Retirement as more than leisure—importance of purpose 21:59 Gradually transitioning into retirement during your 50s 22:58 Shaping work to emphasize what you enjoy most 24:21 Christine’s approach to scaling back work travel 26:22 Lifelong learning through podcasting and interviews 27:49 Whether it’s okay not to retire if you enjoy your work 28:27 Relationships and social connection as the key to retirement happiness 29:40 Introverts and maintaining meaningful friendships 30:05 Research on aging, happiness, and social environments 31:28 Discussion about the future of retirement communities 33:56 Christine’s three key financial steps before retirement 34:42 Calculating retirement spending and non-portfolio income 35:22 Safe withdrawal rates: 3.9% fixed vs flexible strategies near ~5.7% 36:09 The value of fiduciary financial advisors in retirement planning Learn more about your ad choices. Visit megaphone.fm/adchoices
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    43 mins
  • The Wisdom of Crowds
    Mar 10 2026
    Don and Tom start with the classic “jelly beans in a jar” experiment to explain the wisdom of crowds and why large groups often produce surprisingly accurate predictions. That idea leads to a discussion of modern prediction markets like Kalshi and Polymarket, which sometimes outperform professional economists when forecasting things like GDP, inflation, or Federal Reserve decisions. But the hosts emphasize that these predictions ultimately don’t matter to investors, pointing instead to the long-term evidence that active fund managers consistently fail to beat the market. They highlight massive investor flows away from active funds toward index and rules-based strategies and remind listeners that successful investing is far simpler than many believe: save regularly, diversify broadly, keep costs low, and avoid emotional decisions. Listener questions cover tax-efficient asset location across account types, retirement withdrawal strategies including the 5% variable rule, and why short-term differences between funds like AVUV and DFAS are largely irrelevant. 0:04 Jelly beans and the “wisdom of crowds” analogy 2:24 Prediction markets and why crowds sometimes beat expert forecasts 3:29 Research showing prediction markets rival or outperform professional economists 6:01 Why gamblers may make better predictions than professional forecasters 7:04 Betting on prediction markets themselves and recession/interest-rate predictions 8:08 Why economic predictions ultimately don’t matter for investors 8:19 $1 trillion outflow from active mutual funds and the shift to passive investing 9:39 SPIVA data showing 98% of active funds underperform over 10 years 10:46 Index funds vs “rules-based” or evidence-based funds 11:43 The dramatic shift from active to index investing over the past decades 12:41 Why investors don’t need forecasts to succeed 14:28 Listener question: Asset allocation across taxable, IRA, and Roth accounts 17:14 Listener question: RMD timing and the 5% variable withdrawal strategy 20:36 How the 5% variable withdrawal approach works in retirement 22:36 Listener question: AVUV vs DFAS performance differences 24:48 Why short-term performance comparisons are largely meaningless 26:15 Market timing losses despite a strong 2025 market 27:10 Final reminder: No one can predict the future, not even brokers Learn more about your ad choices. Visit megaphone.fm/adchoices
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    31 mins
  • Free Money?
    Mar 5 2026
    AI hype is colliding with financial reality. Don and Tom examine Elon Musk’s suggestion that artificial intelligence could create such abundance that retirement savings might become unnecessary. They unpack the economics behind universal basic income, including the staggering cost—even a modest payment would require trillions in new revenue—and explain why most Americans aren’t betting their futures on Silicon Valley promises. The episode also answers listener questions about confusing target-date fund holdings, what to do with an overfunded 529 plan, and how to reduce taxable investment distributions by placing assets in the right accounts. Along the way they revisit lessons from past technological revolutions, discuss the importance of work beyond income, and continue their campaign against the scourge of gas-powered leaf blowers. 0:04 AI panic and Elon Musk’s claim that AI could make retirement savings unnecessary. 1:52 Musk’s vision of AI-driven abundance and universal income replacing traditional retirement planning. 3:36 The practical question: who actually pays for universal income checks? 5:30 Historical tax rates in the 1960s vs. today’s marginal tax structure. 6:21 Survey shows 94% of readers still plan to save despite AI predictions. 7:17 Boston College researchers warn Musk’s comments send a dangerous retirement message. 8:23 Why universal basic income would require major government policy and taxes. 8:45 Past technology revolutions didn’t distribute wealth evenly. 9:27 Why humans need work for purpose, not just income. 10:33 The math problem: even $1,000/month UBI would require about $3.1 trillion annually. 11:54 Historical comparison to the Luddite era and displaced workers. 13:18 Listener question: What “short-term debt and net other assets” mean in a Fidelity target-date fund. 17:38 Listener question: Overfunding a 529 plan and potential Roth rollover strategies. 20:45 Listener question: Using Vanguard Tax-Managed Balanced Fund to reduce taxable distributions. 23:28 Asset location strategy: placing bonds in IRAs and stocks in taxable accounts. 24:49 Where to easily find mutual fund returns using Morningstar. 25:46 Tom’s Scottsdale advisory meetings announcement. 26:45 The crusade against gas-powered leaf blowers. Learn more about your ad choices. Visit megaphone.fm/adchoices
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    29 mins