Talking Real Money - Investing Talk

Latest Episodes:

Ep. 1836: Extra Income? Feb 23, 2026

Show notes

Don and Tom examine Kiplinger’s list of top retirement side gigs and separate practical ideas from pipe dreams, questioning whether executive coaching, IT consulting, online reselling, and landlord life truly offer “passive” or realistic income. They highlight more viable options like tutoring, handyman work, and tour guiding while emphasizing purpose over paycheck. Listener questions cover the risks of private credit and alternative investments, plus smart strategies for consolidating multiple 401(k) accounts without triggering unintended tax consequences.
0:04 Old guys still podcasting intro
1:38 Kiplinger’s retiree side-gig list
3:26 Executive coaching reality check
4:40 AI and tech consulting skepticism
6:32 Consulting and client ego problems
7:53 AI vs. content writers
9:06 Bookkeeping for small businesses
9:29 Online selling isn’t easy money
11:19 Tutoring as a steady option
12:17 Handyman work pays well
13:44 Tour guide opportunities
14:17 Landlord myth of “passive” income
16:00 Where to find side gigs
16:47 Bridge jobs for healthcare
17:08 Purpose-driven retirement
19:14 Private credit and alternative risks
23:46 Consolidating multiple 401(k)s
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Ep. 1835: Crypto Qs Return Feb 20, 2026

Show notes

After a bump in crypto-fueled listener calls, Don tackles a mix of practical and philosophical money questions: why Fidelity’s new “stablecoin” isn’t an investment at all, whether a heavily conditioned city 401k match is worth the risk versus a flexible Roth 457, how to safely reposition an 85-year-old’s idle savings without sacrificing liquidity, and why actively managed mutual funds can generate painful surprise tax bills. The episode closes with the return of Bitcoin Bob, sparking a spirited debate over whether Bitcoin is a currency, a commodity, or a “store of wealth” — and whether something that swings 50% qualifies for that title.
0:04 Crypto episode follow-up, listener call surge, and AI voice processing update
1:52 Fidelity’s new stablecoin FIDD — why it’s pointless for investors
3:41 City retirement plan dilemma: conditional 401k match vs. Roth 457 flexibility
8:24 When complicated employer matches aren’t worth the hoops
9:31 Helping an 85-year-old move idle savings — high-yield savings vs. brokerage
11:40 Janus mid-cap fund capital gains surprise and ETF tax efficiency
13:11 Why mid-cap alone isn’t diversification — broader ETF alternatives
15:19 Bitcoin Bob returns: currency vs. commodity vs. “store of wealth”
19:53 Volatility reality check — why Bitcoin fails the store-of-wealth test
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Ep. 1834: Going So Low Feb 19, 2026

Show notes

Vanguard lowers fees yet again, pushing its average expense ratio down to just six basis points — a move that underscores how dramatically fund costs have fallen over time. Don and Tom contrast this with shockingly expensive ETFs charging double-digit annual fees and explain why those costs are nearly impossible to overcome. They unpack the difference between pure index funds and factor-based funds like Avantis and Dimensional, clarify common confusion around rebalancing and fund-of-funds strategies, answer listener questions about increasing international exposure, and explain why evidence-based investing includes diversification across bonds and real estate — not just stocks. The episode reinforces a core message: fees matter far more than most investors realize, especially the ones they never see.
0:04 Vanguard cuts fees again — average expense ratio now just 0.06%
1:23 Brief detour into model aircraft before returning to money talk
3:43 Fund expense ratios explained — what investors are really paying
5:00 The shock factor: ETFs charging 12%–14% annually
10:08 Why ultra-high expense ratios are nearly impossible to justify
11:13 Vanguard vs. factor funds — why Avantis and Dimensional cost more
14:41 The invisible cost problem — how expense ratios quietly drain returns
16:03 Militia Long Short ETF (ORR) — high fees, no track record
21:02 Listener question: Increasing international exposure inside IRAs
23:03 One fund vs. multiple funds in taxable accounts — rebalancing clarification
24:09 Why Dimensional and Avantis offer mid-cap, REIT, and bond funds
25:51 Evidence-based diversification beyond equities
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Ep. 1833: Even 500 Is Too Few Feb 18, 2026

Show notes

Don and Tom tackle S&P 500 concentration risk and the dominance of the Magnificent Seven, explaining why diversification still matters despite compelling active management narratives. They clarify the difference between currency and investment in a pointed Bitcoin vs. U.S. dollar discussion, then pivot to fixed income strategy—highlighting why low-cost, large-scale bond funds like BND often outperform higher-fee “active” alternatives that quietly take more credit risk. Listener calls cover 401(k) catch-up contributions, bond ETF selection for retirement income planning, and whether using excess RMD funds for Roth conversions really adds value after taxes and IRMAA considerations. As always, the theme is disciplined investing over storytelling.
0:04 Technical chaos intro and why better investing still matters
1:32 S&P 500 concentration risk and the “Magnificent Seven” problem
2:40 The dangerous “but” in diversification pitches
3:43 Small, value, and momentum factors explained briefly
5:33 Active management as narrative creation
9:57 Bitcoin vs. U.S. dollar as currency vs. investment
13:29 What actually makes something an investment
15:08 Bond ETFs for retirement years 5–8: BND vs. Avantis
17:42 Why bond fund size and expenses matter
21:36 Active bond ETFs, credit risk, and hidden tradeoffs
25:38 401(k) catch-up contributions clarified
30:21 Roth conversions, RMD strategy, and tax math realities
34:09 IRMAA considerations and Medicare premium surprises
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Ep. 1832: Over Active? Feb 17, 2026

Show notes

Don and Tom dissect a Morningstar article naming the “best core stock funds” for 2026, noting the sharp decline in recommended actively managed funds and the dominance of low-cost index funds. While they applaud the shift away from expensive stock pickers, they argue Morningstar’s “core” approach still leads to unnecessary complexity and heavy large-cap (especially S&P 500) concentration, with little exposure to small-cap, value, and emerging markets. They advocate instead for simple, globally diversified, factor-tilted funds like DFAW, AVGE, or AVGV. Listener questions cover switching from AVGE to AVGV inside an IRA (risk tolerance matters), improving a 32-year-old’s 401(k) allocation (use a Roth IRA to add small/value exposure), and a sharp analogy comparing passive investing to driving with traffic rather than weaving aggressively for no gain.
0:04 Investing in a “wonderful world” by ignoring noise
1:14 AI audio tools that may replace editors (and shorten meetings)
5:06 Morningstar’s 2026 “Best Core Funds” list shifts toward indexing
6:39 Why “core” still means large-cap heavy and incomplete diversification
9:50 The problem with piling into multiple S&P 500 funds
12:14 Why Dimensional and Avantis are missing from the list
13:26 One-fund global solutions: DFAW, AVGE, AVGV
17:44 Listener analogy: aggressive driving vs. active investing
19:08 IRA question: Switching from AVGE to AVGV and risk tolerance
20:34 32-year-old’s 401(k) allocation and using a Roth IRA to add small/value
28:40 Retirement workshop plug and who should attend
30:21 Free fiduciary advice vs. actually hiring an advisor
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Ep. 1831: Nicer Qs Feb 13, 2026

Show notes

In this Friday Q&A episode, Don introduces a new AI audio enhancement tool that dramatically improves the sound quality of listener questions, then dives into a series of practical retirement issues. He tackles whether converting a $2 million term life policy to whole life after a disability makes sense (and what must be guaranteed in writing), explains how to properly freeze a deceased parent’s credit and handle inherited POD accounts and IRAs under the 10-year rule, pushes back on the increasingly discussed “bond trough” retirement strategy by emphasizing emotional risk over theoretical logic, and closes with reassurance for listeners considering retiring part-time in Mexico, explaining how U.S. retirement accounts, tax treaties, and global banking make the process far simpler than many assume.
0:04 Friday intro and new AI tool that dramatically improves caller audio quality
2:01 Whole life conversion offer after disability — “free” premiums and what to demand in writing
5:57 How to submit spoken questions and call-in info
6:22 After a parent’s death: credit freezes, deceased alerts, and final credit reports
7:41 Inheriting POD accounts and an IRA — step-up in basis and the 10-year IRA rule
9:57 AVGE vs. AVGV fake-out and real question: bond “trough” strategy in retirement
11:24 Logical vs. emotional risk tolerance — why most retirees can’t handle 50% drawdowns
13:40 Retiring internationally (Mexico example) — IRAs abroad, tax treaties, and practical
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Ep. 1830: Know You Can't Know Feb 12, 2026

Show notes

Markets may feel calm despite geopolitical noise, but uncertainty is the permanent condition of investing—and the price of admission for higher returns. Don and Tom unpack Jason Zweig’s reminder that investors hate uncertainty (tough), discuss the surge in speculation from leveraged ETFs to prediction markets, and explain why “play money” accounts should stay small. They field listener questions on building an investment policy statement, rebalancing without sabotaging returns, simplifying overly complex ETF portfolios, choosing international small-cap exposure, and setting up custodial accounts (with a nod to Roth IRAs for working teens). The core message: take only the risk you need, not the risk your inner con man wants.
0:00 The podcast that never ends; investors hate uncertainty
1:19 Jason Zweig revisits 2008 and the permanence of market uncertainty
3:16 Calm markets, speculative behavior, and the rise of prediction markets
6:00 “Play money” accounts and the danger of confusing gambling with investing
8:18 Take the risk you need—not the risk you want
9:05 Writing down how you feel during downturns
11:51 Listener question: Rebalancing and creating an Investment Policy Statement
17:09 25-year-old portfolio review: Too much complexity, wrong tilts
20:27 International small-cap choice: AVDV vs. AVDS
23:26 Custodial accounts for teens and the Roth IRA opportunity
26:10 RetireMeet 2026 promotion and event details
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Ep. 1829: When Dull is Desirable Feb 11, 2026

Show notes

Talking Real Money opens with a stark illustration of why Bitcoin fails as a usable currency, showing how volatility can destroy real-life budgets overnight. Don and Tom compare crypto to historic speculative bubbles, argue that stability—not hype—is the core function of money, and dismantle the “store of value” narrative. The show then shifts to practical listener calls covering CD ladders, Treasury yields, retirement readiness, estate planning, and early-retirement balance. Throughout, they emphasize boring, diversified, evidence-based investing over speculation, reminding listeners that long-term financial security comes from discipline, planning, and emotional restraint—not chasing the next hot trend.
0:04 Bitcoin paycheck scenario and real-world income collapse
1:04 Currency volatility vs. household budgeting reality
2:22 Bitcoin’s 45% drop and “currency vs. speculation” argument
3:24 Hyperinflation examples and why stability matters
4:03 “Greater fool” theory and vanishing crypto hype
4:47 Why Bitcoin fails as a functional currency
5:59 Tulip mania and historical bubbles comparison
6:59 Tangible assets vs. pure speculation
7:39 “At least you can live in a house” argument
8:26 Michael Saylor, HODL culture, and empty promises
9:30 NFT collapse and Beeple example
10:11 Crypto returns vs. real assets
11:14 Listener question: CDs vs. Treasuries
12:22 Current CD rates and Bankrate reference
13:56 Risks of long-term bonds and rate changes
15:32 Don’s real CD ladder example
16:37 Fixed income diversification strategy
18:35 Hot money leaving crypto for prediction markets
19:45 Generational blind spots and bubble psychology
21:08 Retirement planning call: housing proceeds and savings
23:57 Social Security timing and cash-flow planning
25:41 Importance of fee-only fiduciary planning
27:32 Vernita Toll Bridge digression (classic TRM)
30:33 Estate planning: wills vs. trusts
33:49 RetireMeet promotion and resources
35:43 FIRE listener call: saving vs. living balance
38:58 Permission to spend responsibly
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Ep. 1828: A Better Way Feb 10, 2026

Show notes

0:04 Dow hits 50,000 while most stocks lag—why it’s a meaningless headline
0:59 Robinhood and Palantir slide—speculators start getting nervous
1:39 Jason Zweig on low-volatility funds—and why timing them is a trap
1:55 Why the Dow is a terrible “index” built on 1890s math
3:22 Diversified portfolios quietly up nearly 6% YTD in early 2026
3:32 Small-cap value up 13%—the payoff of long-term discipline
4:05 “We didn’t predict this”—why diversification beats market bragging
4:54 Portfolios should already be built for downturns
5:10 The danger of reacting after markets “stumble”
7:09 Average vs. median net worth—why averages mislead
8:26 How billionaires distort financial statistics
9:09 “Lies, damned lies, and statistics” origins
10:06 AI-enhanced listener call audio and Friday Q&A podcast
10:37 DFFVX vs. AVUV—Dimensional vs. Avantis small-cap value
13:33 Why track records don’t matter for similar funds
13:53 Super Bowl sirloin cooking advice
15:17 Whole life insurance review—why to cash out in retirement
17:08 When cash-value insurance makes sense (rarely)
19:22 Surprise downloads of Christmas stories in February
20:57 Caller asks about “set-it-and-forget-it” investing
24:26 Risk tolerance when retiring soon
26:08 Using AVGE for global diversification
27:48 Why near-retirees should get professional reviews
30:28 Emergency funds—never use a Roth
31:37 High-yield savings accounts around 4%+
34:11 Portfolio balance and realistic expectations
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Ep. 1827: Alternative Employment Feb 09, 2026

Show notes

Don and Tom step away from pure investing talk to explore how AI, layoffs, and stagnant wages are reshaping career paths—especially for young people and midlife career changers. Drawing on a Wall Street Journal article, they make the case that skilled trades and blue-collar careers are increasingly attractive alternatives to vulnerable white-collar jobs. They discuss service advisor roles, union trades, and apprenticeship paths, then pivot to listener questions on Robinhood bonuses, switching to financial advising later in life, and the risks of moving from AVGE to AVGV. Throughout, they emphasize self-knowledge, discipline, and long-term thinking—whether choosing a career or building a portfolio.
0:04 Why this episode is about earning money, not just investing
0:31 Encouraging parents to rethink college-only career paths
1:15 AI, layoffs, and the shrinking white-collar job market
2:32 Crash Champions and the rise of service advisor careers
3:31 Don’s dealership days and why he left the car business
5:12 Learning to drive stick shift the hard way
6:46 Apprenticeships, $60K starting pay, and growth potential
7:34 Work-life balance in blue-collar vs. white-collar jobs
8:36 Why contractors struggle with communication and planning
9:05 Demand for skilled trades and handyman services
9:47 Labor shortages: factory, construction, and auto techs
10:36 Demographics and the retirement of skilled workers
11:35 Pensions, unions, and taking responsibility for retirement
12:45 Finding yourself in your 20s and career experimentation
13:04 New Tales Told plug and early radio career story
14:23 Listener: Robinhood bonuses and disciplined investing
15:41 Why Robinhood encourages risky behavior
17:23 Listener: Becoming a financial advisor at 55
18:31 Barriers to entry and starting an independent RIA
19:14 Why people skills matter more than math skills
20:45 How AI will reshape the advisory profession
22:07 Shift from brokerage to fiduciary advising
23:18 Listener: Switching from AVGE to AVGV
24:47 Risk tolerance and fund volatility
26:31 Splitting funds and managing behavioral risk
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