Talking Real Money - Investing Talk

Latest Episodes:

Ep. 1856: Icy Market Mar 23, 2026

Show notes

The housing market is stuck in an unusual freeze, driven by the lingering effects of ultra-low COVID-era mortgage rates, reduced housing inventory, and sharply higher income requirements for buyers. With fewer people moving, less new construction, and more all-cash purchases, affordability has deteriorated and first-time buyers are older than ever. Don and Tom argue that homeownership is often overrated as an investment and suggest renting may be the more rational choice for many. They also tackle listener questions on Robinhood’s 2% transfer bonus (tempting but tied to a five-year lockup), comparisons between today’s market and 1929 (very different structurally), and the limits of 529-to-Roth conversion strategies. Along the way, they remind us that humans—like chimps—are irresistibly drawn to shiny objects, which often leads to poor financial decisions.
0:04 Housing market shift and mortgage demand decline
1:18 COVID-era rates and the “locked-in homeowner” effect
2:23 Inventory shortage and collapse in new construction
2:41 Income needed to buy a home jumps dramatically
3:27 First-time buyers getting older and priced out
4:21 Why the housing market feels “frozen”
5:35 Mortgage rates vs. psychological anchoring to 2% loans
6:23 Advice: rent before buying in uncertain markets
7:36 Flexibility in location and housing expectations
9:20 Helping family vs. accepting renting as a long-term solution
10:05 Why homeownership is not a great investment
11:05 Hidden and unpredictable costs of owning vs. renting
11:56 Possible long-term shift toward renting culture
13:46 Robinhood 2% transfer bonus—too good to be true?
15:13 The five-year lockup and real cost of “free money”
16:38 Temptation vs. trust issues with Robinhood
17:18 Listener question on 1929 comparisons
18:25 Why today’s market is fundamentally different from 1929
20:34 Extreme leverage and speculation in the 1920s
22:03 Regulatory differences and modern safeguards
23:32 529 plan to Roth IRA conversion rules explained
24:47 Beneficiary changes reset the 15-year clock
25:29 “Shiny object” behavior and investing mistakes
27:12 Human nature, speculation, and financial decisions
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Ep. 1855: Fewer Q Friday Mar 20, 2026

Show notes

Don fields listener questions on asset allocation, advisor timing, and investing complexity with his usual bias toward simplicity and self-awareness. He emphasizes that the decision to add bonds isn’t about age but about emotional tolerance for loss, shares his own shift to a more conservative 55/45 portfolio, dismisses futures markets as largely speculative noise for most investors, and advises a listener nearing retirement that while there’s no urgency to hire an advisor, the value of planning—especially around taxes and income strategy—becomes increasingly important in the early 60s.
0:04 Thunderstorm intro and Q&A format setup
1:37 100% stock portfolio—when (and how) to add bonds
5:47 Don’s personal portfolio breakdown and evolution
10:25 Futures markets explained (and why to ignore them)
13:00 When to hire a financial advisor approaching retirement
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Ep. 1854: Optimal Income? Mar 19, 2026

Show notes

Morningstar’s latest research nudges the “safe” withdrawal rate down to 3.9%, but Don and Tom make it clear there’s no magic number—just tradeoffs. They walk through fixed vs. flexible withdrawal strategies, why spending adaptability matters more than rules of thumb, and how your goals (spend vs. leave money behind) shape everything. Listener questions tackle bond fund choices (yield vs. stability), portfolio allocation math, and whether an advisor should pay for a costly tax mistake (short answer: yes).
0:04 The big retirement question: how much can you safely withdraw?
0:32 Morningstar updates the “4% rule” to 3.9%
0:55 Why their baseline uses a conservative 40/60 portfolio
1:59 Overview of multiple withdrawal strategies (guardrails, RMDs, etc.)
3:13 Why rules of thumb fail real people
4:17 Flexible withdrawals vs. fixed income strategies
5:43 Spending more vs. leaving more—values drive the decision
6:36 Why professional planning still matters (even for pros)
7:38 What Morningstar data shows about spending vs. ending balances
9:05 The real key: flexibility in retirement spending
10:22 RMD strategy—high spending, low legacy
12:36 Listener Q: Active vs. index bond funds (yield vs. quality)
15:09 Why bonds are about stability, not returns
17:13 Listener Q: Portfolio allocation math (70/30 breakdown)
17:58 How much international exposure is “right”
19:44 Listener Q: Advisor mistake causing tax penalties
21:20 Should advisors reimburse errors? (yes—and they usually will)
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Ep. 1853: Everything Ends Mar 18, 2026

Show notes

The show opens with a major announcement: Talking Real Money is leaving terrestrial radio and going fully podcast-only, marking the end of a 16-year Saturday run. A heartfelt surprise call from Don’s wife Debbie reflects on decades of friendship, trust, and listener connection before the tone pivots back to business. The main topic takes aim at perpetual crash predictors like Robert Kiyosaki, dismantling their track records with hard numbers and highlighting the absurdity of market timing. The episode then shifts to a real-world HOA investing debate, using it as a case study to expose the risks and illusions behind “buffered” or “guaranteed” return products. The core message is simple and consistent: if it sounds too good to be true—especially anything promising safe double-digit returns—it is.
0:04 Major announcement: show leaving radio, moving fully to podcast
0:34 Surprise call from Debbie with emotional tribute
2:13 Reflection on 16 years, trust, and listener impact
3:15 Don and Tom respond to Debbie and reflect on friendship
5:16 Setup: can anyone actually predict a market crash?
6:41 Media fear machine and constant crash headlines
7:44 Kiyosaki’s predictions vs real market performance
9:52 “25 of the last 2 crashes” and the contrarian indicator joke
11:05 Why crash predictions persist and attract attention
12:29 Other fear-based forecasts and why they don’t help investors
13:29 Program note: transition to podcast-only and how to listen
14:32 Caller: rebuilding an emergency fund vs investing
15:58 How to prioritize emergency savings vs brokerage contributions
16:55 Managing risk and asset allocation near retirement
17:32 Caller question: how interaction will work in podcast format
18:57 New system for listener calls and recorded conversations
21:40 HOA story: pressure to invest reserves in complex products
22:54 Explanation of buffered/structured investment products
24:06 Hidden tradeoffs: capped upside, partial downside protection
25:00 Unknown risks and 2008 comparison
25:47 “Do you know who I am?” moment and advisor pushback
27:01 Reality check: no such thing as guaranteed 10% returns
27:27 Simple logic: if 10% were safe, no one would take 4%
28:59 “People lie about money” and incentives in finance
30:12 Listener email: estate planning and Tom’s Starbucks joke
32:09 RetireMeet recording availability and follow-up
34:08 Podcast reach vs YouTube performance
35:28 How to listen and interact with the show going forward
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Ep. 1852: Retired Broke Mar 17, 2026

Show notes

As Talking Real Money prepares to leave terrestrial radio and become a podcast-only show, Tom and Don pivot from logistics to a deeper issue: the growing financial fragility of retirees. With fewer than 3% of Americans over 65 holding $1M in retirement savings and bankruptcy rates rising among seniors, they explore whether the shift from pensions to 401(k)s helped or hurt. While critics call 401(k)s a failed experiment, the hosts argue the real problem is behavior, education, and lack of early saving. Listener calls reinforce the divide—some are planning wisely in their 30s, while others highlight rising costs, lack of savings, and economic strain. The episode closes with practical withdrawal strategy discussion, a sobering look at consumer stress from a car dealer’s perspective, and a reminder that markets can’t be timed—only prepared for.
0:04 Show moving to podcast-only format; listeners urged to switch now
1:55 RetireMeet recap and airline misery detour
2:44 Retirement reality: few have $1M; rising senior financial distress
4:46 Are 401(k)s a failed experiment? Origins and debate
7:47 Start early: advice for younger savers and families
8:05 Listener JJ: podcast loyalty, missing question glitch
10:47 How call-ins will work after radio show ends
12:06 “Retirement isn’t a switch” — easing into fewer workdays
13:52 Jason: loss of live call-in routine and future logistics
16:53 James (35): starting early and influence of Paul Merriman
20:13 Dave: cost of living, lack of savings, generational habits
23:01 Education gap: financial literacy and modern retirement problem
24:57 Retirement is new: life expectancy and historical context
27:03 Forced savings idea vs behavioral reality
28:11 Caller portfolio: withdrawal strategy, RMDs, tax sequencing
31:59 Importance of personalized planning vs rules of thumb
34:41 Car dealer insight: credit tightening, consumer stress signals
34:59 Market reality: recessions inevitable, timing impossible
36:21 Final push: shift to podcast listening and how to access
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Ep. 1851: More Questions! Mar 16, 2026

Show notes

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.
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Ep. 1850: Exchange Traded Gambling Mar 16, 2026

Show notes

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
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Ep. 1849: Questions Four Mar 13, 2026

Show notes

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
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Ep. 1848: Don't Invest? Mar 12, 2026

Show notes

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
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Ep. 1847: Retiremeet 2026 Part Two Mar 11, 2026

Show notes

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.
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