Talking Real Money - Investing Talk

Don goes solo this week and covers the wild state of “investing” in 2025 — including single-stock ETFs, leveraged funds, and zero-day options that look more like gambling than investing. He answers listener questions about Roth strategies for kids, aggressive long-term allocations, finding fiduciary advisors, dealing with inherited stock portfolios, and the ethics and fees of big Wall Street firms. Plus, he fields questions about new tax-focused ETFs and whether complicated multi-fund factor strategies are really worth the trouble.

0:04 Don jokes about ChatGPT replacing him, welcomes listeners

1:53 Today’s topic: 30% of new ETFs are tied to single stocks —...

This week Don hosts solo and brings in “Cath GPT” (ChatGPT) as a "live" guest to explore the rise of AI in personal finance. They cover what types of questions AI is best at answering, its limits for real-time data and stock trading, and the importance of privacy and skepticism. Don emphasizes planning before investing, critiques dollar-cost averaging with lump sums, and fields listener calls on shifting from commercial real estate to the market, Roth conversions, AVGE vs. AVUV, resetting cost basis in a low-income year, and avoiding dubious “legacy funds.” The show closes with reminders about planning, asking spoken q...

Don and Tom take listeners on a “mountaintop” look at today’s frothy markets, exploring elevated valuations, retail trading spikes, and record margin debt. They unpack what these numbers really mean, warn against trying to time the market, and reiterate the need for diversification and a long-term plan. Listener questions include a young investor’s Fidelity-heavy portfolio, a 30-something’s aggressive allocation and risk score mismatch, and a listener inquiry about “investwithroots.com,” which Don dissects as a private real-estate fund with fees and risks that outweigh its glossy promises.

0:04 Opening from the market “peak” and climbing metaphor

1:3...

Don answers listener questions on funding a taxable brokerage account, clarifies what “more buyers than sellers” really means, explains why fixed income is about psychology rather than income, gives advice on setting up joint accounts for aging parents, lays out a lifetime HSA allocation strategy, and clears up confusion about Appella Wealth’s connection to Talking Real Money.

0:04 Friday Q&A intro and thanks for listener questions

1:19 When to open a taxable brokerage account (AVGE + SGOV mix)

3:28 “More buyers than sellers” — why it’s really about demand vs. supply

6:23 Whether pension + Social Securit...

Don and Tom dig into international investing — why diversification across borders is essential, why timing international markets is a mistake, and how currency fluctuations affect returns. They revisit Japan’s lost decades, talk emerging markets, discuss John Bogle’s arguments against international investing, and explain why owning all markets all the time makes the most sense. Listener questions cover tax perceptions about California, long-term return comparisons, 401(k) rollover and Rule of 55 withdrawals, and the realities of retiring abroad — including the sticker shock of Guatemala’s healthcare spending.

0:04 Should you invest internationally now that foreign markets are rising?

1:29...

In this episode, Don and Tom dig into the podcast rankings to explain why Talking Real Money isn’t at the top—and why Dave Ramsey still is, despite offering more shame than substance. They explore the concept of financial shaming vs. education, reflect on listener Judy’s brilliant retirement planning, and take aim at stock-trading politicians, especially California Rep. Ro Khanna with his 4,700+ trades in one year. Listener questions cover inheritance allocation, condos as investments, and 401(k) vs. Roth vs. brokerage savings. Bonus: Tom yells at his grandkids, Don hates condos, and Congress gets roasted.

0:04 Who’s #1 in...

Don and Tom break down the overhyped expectations around recent market returns, referencing Jason Zweig’s analysis of 230 years of stock market data. They emphasize that spending and saving habits matter more than chasing 15% returns, and explain why realistic planning using a 3–6% real return assumption over 30-year rolling periods is more prudent. They also tackle questions about RMD strategies from Vanguard IRAs and the TSP’s F and G bond funds. The show ends with a tongue-in-cheek breakdown of NFL team valuations—yes, the Raiders rank surprisingly high.

0:04 Welcome, fatuousness defined, and realistic investing begins

0:52 Why you...

Don and Tom dive into the emotional, financial, and practical realities of supporting adult children. From layoffs to loans, down payments to dog surprises, this episode tackles the growing trend of parents funding their 20- and 30-something offspring—and how to do it without wrecking your retirement. Plus, listener questions about gifting stock, promissory note scams, and why shady annuity sellers keep showing up on the airwaves.

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In this Friday Q&A edition, Don fields listener questions on rolling over a large 401(k) after a layoff, whether IRA money should ever be used to buy real estate, Vanguard’s new active ETF offerings, choosing between Vanguard and Schwab 2035 target-date funds, and whether to treat a foreign apartment purchase as part of an investment portfolio. Along the way, he highlights diversification benefits, cautions against high-cost self-directed IRAs, and emphasizes that homes are assets but not investments.

0:04 Friday intro, royal “we,” and reminder on how to submit questions

1:42 Scott from Louisiana: rolling over a $1M reti...

Don and Tom dismantle the “passive bubble” trope, walk through Morningstar’s active/passive scorecard (great one-year anecdotes vs brutal long-run stats), and recap the steady shift of investor dollars toward indexing. A caller tries to drag the show into politics via data independence (BLS/Fed), prompting a level-headed reminder that markets price reality over rhetoric. The TSP’s revamped I Fund gets kudos for finally adding emerging markets (with a nudge to pair it with value tilts outside TSP). Two meaty segments cover long-term care: costs, weak benefits on traditional policies, when hybrids can make sense, and why many hou...

Don and Tom mark Labor Day weekend with a lively discussion of the so-called September Effect—Wall Street’s superstition about historically negative returns in September. They remind listeners that short-term market timing is a losing strategy and that knowing (not guessing) your risk tolerance and asset allocation matters most. The conversation ranges from Florida’s endless summer and biblical rains to ETF overload, collective investment trusts, tax quirks, and the futility of dodging volatility. Along the way, there’s humor about Costco, fertilizer, wrong numbers, and shameless plugs for Don’s LitReading podcast.

0:04 Labor Day banter, Florida he...

Tom kicks off with a check-in on bond market returns, reminding listeners that bonds are about stability, not yield-chasing. He’s joined by advisor Roxy Butner, who helps answer listener questions about fixed-allocation vs. target-date funds, how much international exposure is enough, Ameriprise “CL” fund share classes with high fees, and whether hybrid long-term care annuity products are worth considering. Together they emphasize cost awareness, simplicity, and aligning investments with real-life needs instead of sales-driven products.

0:04 Intro and bond returns update (BND, DFIGX, SWSBX)

2:30 Why bonds belong in portfolios despite modest returns

2:47 Mailbag intro...

Don fields listener questions from Asheville in this Friday Q&A edition. Topics include calculating investment returns with XIRR versus simple time-weighted methods, rebalancing U.S. vs. international allocations in a Vanguard portfolio, whether children can have multiple custodial accounts (and why 529s may be better), AVGE versus VT and why factor tilts matter long-term, and a skeptical look at Frank Vasquez’s Risk Parity Radio strategy that leans on commodities and “golden ratio” portfolio construction.

1:03 How to calculate investment returns (XIRR vs. time-weighted)

4:19 Portfolio allocation: VTI + VT + BND vs. simpler mix

7:10 Custodial UTMA a...

This episode of Talking Real Money digs into recency bias—our human tendency to expect the future to look like the recent past—and how it’s quietly reshaping retirement portfolios. Don and Tom examine rising stock allocations in 401(k)s and target-date funds, even among older investors, and why this performance-chasing is dangerous. They highlight the risks of target-date fund managers pandering to investors, the importance of rebalancing, and the need to stick to long-term allocation plans based on risk tolerance, not market trends. Listener questions cover immediate annuities, 529-to-Roth transfer rules, and whether paying an advisor’s 1% fee is w...

Tom Cock takes the reins while Don visits family, leading a live call-in show that covers liquidity risks in private investments and university endowments, skepticism over deferred income annuities, housing sale costs, Vanguard ETF gaps, the importance of diversification beyond the S&P 500, and why long-term investing discipline beats reacting to short-term volatility. Callers ask about annuities, real estate commissions, balanced ETFs, 100% stock allocations, and Wellington vs. total market strategies, with Tom stressing global diversification, risk awareness, and building portfolios for real life rather than chasing products or peer pressure.

0:04 Tom hosts solo, Don away visiting his m...

Tom Cock hosts this week’s Talking Real Money solo while Don visits his mom. He reflects on Appella Wealth’s annual client event, where clients talked more about travel, grandkids, and weather than money—showing that the firm’s real value is helping people worry less about markets and more about life. Tom takes listener calls covering whether to renew CDs or move into bond funds, the high costs of closed-end muni funds, portfolio planning with Roth IRAs and target-date funds, estate planning with mutual fund capital gains, and frustrations with annuities. Throughout, Tom stresses planning, simplicity, ignoring noise, a...

Don and Tom revisit their long-standing skepticism of Yieldstreet after CNBC’s investigation reveals major investor losses. They highlight how promises of high returns and low risk almost always end in disaster, connecting this lesson back to their 2022 warnings. The episode underscores the dangers of “magical” investments, the myth of passive income, and why retirement accounts should avoid private assets. Listener questions focus on Roth vs. pre-tax strategy, bracket management, and conversion rules—showing the complexity of tax planning when wealth accumulates.

0:04 Why “too good to be true” investments always fail eventually

1:08 Yieldstreet problems exposed—CNBC investigati...

This question heavy episode of Talking Real Money dives into six listener questions ranging from umbrella insurance and portfolio rebalancing to small-cap value allocation, AI’s role in financial planning, and advisory fees. Don critiques umbrella policies as overpriced peace-of-mind products, gives practical strategies for balancing across multiple accounts, stresses the value of both U.S. and international small-cap value, discusses the disruptive potential of AI in advice (with a cameo from “Kath”), and explains fiduciary fees, taxes, and client experience at a fee-only firm like Appella.

0:04 Big Q&A episode intro and listener reminder about submitting questions...

Why has the stock market been so persistently resilient despite crises like COVID, wars, and inflation? Don and Tom explore whether the current generation of investors is simply too inexperienced to remember real bear markets—and what that means for the future. They reflect on market history, including the 2000–2009 “lost decade,” and warn against overconfidence and overconcentration in U.S. large caps. The episode covers lessons from diversification, the value of bonds, the illusion of wealth during bull markets, and listener questions about rebalancing strategies, tax-efficient withdrawals, and international fund choices. They wrap up with a hilarious movie segment and a pl...

Don and Tom explore why real-life investors consistently underperform the market—thanks to emotional decisions, frequent trading, and flashy sector bets. They break down Morningstar’s “Mind the Gap” study and explain why your behavioral return often lags the market return. Listener questions lead into heated critiques of 403(b) plans packed with annuities, an exploration of the risks of overconcentration in the S&P 500, second-home planning in retirement, and the tax headache of unwinding inherited tech stocks. It’s a fast-paced episode packed with practical advice and sharp jabs at high-fee products and financial marketing nonsense.

0:04 Investor returns vs...

This lively episode of Talking Real Money features trivia-packed investing fun, smart listener questions, and sharp commentary from Don and Tom. They dive into a Wall Street Journal quiz on investing genius, exploring surprising historical returns and market myths. Listener calls span a range of financial planning topics—from special needs trusts and Roth IRAs for kids to emergency fund placement and ETF selection.

0:04 Don and Tom banter about working weekends and boomers in the office

1:55 Wall Street Journal quiz: Are you a stock market genius?

3:20 Which stock created the most wealth in 100 ye...

In this episode, Don and Tom confront the emotionally charged—and often financially tragic—decision to claim Social Security early. They debunk three common justifications: fear of system insolvency, false break-even math, and “I just want my money.” Don shares his own benefit numbers as a real-world example of the value of waiting, especially for married couples. They also address why many can’t wait and explore whether alternatives like balanced portfolios or annuities make sense. Later, they roast misleading “hybrid pension” annuity schemes from KCIS, field smart ETF questions about AVGE and AVNM, and talk target-date funds, including why some belon...

Listener Q&A covering early retirement feasibility, VT vs. SPGM ETF comparison, tax-efficient liquidation of a legacy mutual fund, recommended financial planning resources and Monte Carlo tools, and the pros and cons of laddering target-date funds.

1:36 Can $120K a year work with two pensions and a 7% return?

4:57 VT vs. SPGM — same global reach or hidden differences?

8:58 Selling Grandma’s mutual fund without gifting Uncle Sam

11:44 Best deep-dive planning books and free Monte Carlo tools

15:56 Target-date laddering — smart risk tweak or needless fuss?

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Tom Cock interviews Megan Gorman, author of All the President’s Money, exploring how U.S. presidents have handled their personal finances and the lessons investors can take from their successes and failures. Gorman shares stories of leaders from George Washington to Ronald Reagan, Eisenhower, Nixon, and Clinton, illustrating how factors like marriage, frugality, grit, emotional control, and adaptability shaped their financial outcomes. She notes that while the basic principles of money management haven’t changed since Washington’s time, achieving the American dream has become harder. The conversation touches on how some presidents leveraged post-office opportunities, the ethics of pol...

Don and Tom rip apart a sponsored “news” piece from the Puget Sound Business Journal pushing a company called FISYN, which promises to buy investors out of their annuities and deliver a “safe” 12% tax-free return via raw Texas land. They expose the misleading fine print, the founder’s disciplinary history, and the high-risk, illiquid nature of such private equity deals. Calls and questions cover long-term care insurance riders on annuities, portfolio allocation in deferred comp plans, Roth vs. tax-deferred placement for bonds, managing taxable brokerage cash vs. emergency funds, and dividend-vs.-total-return withdrawal strategies. They also clarify that QCDs can only c...

Today’s show exposes how Barron’s ran an undisclosed advertorial from a high-fee bond fund manager pushing junk-heavy, risky products while trashing traditional bonds with misleading comparisons. Don and Tom explained why safe bonds should stay short-to-intermediate term and simple, called out a Starlink “$127 for life” internet scam, and fielded listener questions on tax-adjusted rebalancing between traditional and Roth IRAs, trimming long-held Microsoft vs. American Funds, Social Security timing myths, and why Bitcoin isn’t an investment. An email question on replacing BND rounded out the episode with a reminder that its structure still works for most investors.

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Don opens with a rant about Wall Street’s love of unnecessary complexity, focusing on “structured equity products” and other layered investments that promise protection but deliver lower returns at higher costs. The discussion covers the deceptive pitch, the billions invested in these products, and why a straightforward stock/bond mix is usually better. Larry Swedroe’s principles for prudent investing are highlighted, along with a reminder about diversification beyond the S&P 500—especially into international and emerging markets. Listener questions cover how to measure global exposure, medical IRA withdrawals, ETF dividend taxation, eliminating Empower as a middleman, and whether re...

In this Friday Q&A edition, Don tackles five listener questions spanning kids’ UTMAs vs. 529 plans, Roth vs. pre-tax 403(b) contributions, filling portfolio gaps when a workplace plan lacks small-cap value, why indexed annuities are a costly sales pitch wrapped in deceptive promises, and how to help a recently divorced 26-year-old daughter find hope and financial focus. Along the way, he delivers mic technique tips, portfolio simplification advice, and a blistering breakdown of annuity sales incentives—plus a reminder to prioritize life and mental recovery over rushing into big purchases.

0:04 Florida heat, Friday Q&A setup, and micr...

Don and Tom dive headfirst into the wild world of bad financial predictions—specifically, the apocalyptic ramblings of Rich Dad Poor Dad author Robert Kiyosaki. They dissect his decades-long streak of failed forecasts, poke holes in his fear-fueled pitch for gold, silver, and Bitcoin, and remind listeners that gurus don’t predict the future—they profit from pretending they can. Listener questions cover 529 plan choices, 457(b) vs Roth IRA, the small-cap allocation in AVGE, and a plea for Don to never give up managing his own money.

0:04 Tom banned from pushing buttons—again

1:00 Why do we idoli...

This Talking Real Money episode dives into America’s millionaire boom—1,000 a day—and what it really takes to join the club. Don and Tom discuss inflation’s impact on wealth, the real sources of millionaire status (spoiler: it’s not crypto), and the critical role of forced savings via homes and 401(k)s. Listeners call in with questions on triple-leveraged ETFs (don’t), deferring capital gains on farmland, and gambling on tech stocks in retirement (also don’t). Plus, how to evaluate a financial advisor and why returns-based promises are a huge red flag.

0:04 The millionaire explosion: 1,0...

Don and Tom open the show with a lighthearted reminder that money doesn’t sleep—so neither do they. They dive into a New York Times article featuring Goldman Sachs researchers who identify five patterns that influence retirement accounts and market behavior. The duo emphasizes that while market predictions are near-impossible, understanding these patterns can inform better investor behavior—particularly the value of diversification. Listener questions cover whether you still need a financial advisor with a $2 million DIY retirement portfolio, the logic behind using a Roth as an emergency fund, tax-efficient asset liquidation, and Washington State’s retirement target-date fund ass...

In this episode, Don and Tom tackle investor emotion during market highs and use a Schwab-inspired scenario to show how discipline beats market timing—every time. They walk through four fictional investors (lucky, disciplined, unlucky, and fearful) to reveal the long-term value of staying invested. The hosts also answer a listener’s question about breaking into the fiduciary advice world and finish with a blistering takedown of FIBA, a so-called fiduciary group pushing high-commission annuities to federal workers. This one’s part reality check, part rally cry.

0:04 Emotional investing and the danger of reacting to market highs

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With Don out, Tom Cock and advisor Roxy Butner tackle the increasingly hot question: should you trust a human or a machine with your money? They dig into two recent studies—one showing AI beating most fund managers, and another suggesting no long-term winner at all. Listener questions range from DIY ETF portfolios and Roth IRA conversion pitfalls to a wildly complex $2.5M retirement scenario involving crypto, precious metals, and a self-directed IRA full of land. Tom and Roxy break it all down with practical advice and a few well-placed jabs at donut holes, Darth Vader, and inheritance headaches.

Don and Tom take a reality sledgehammer to investors’ wildly inflated expectations for stock market returns. A new survey shows average Americans expect 12.6% after inflation, even as historical real returns rarely crack 9%. They explore how this overconfidence—fueled by recency bias and company loyalty—leads to dangerous behavior like under-saving, over-spending, and poorly diversified portfolios. With real-world client stories, historical decade-by-decade returns, and a deep dive into how long it takes portfolios to recover after major drops, they reinforce the need for long-term discipline and diversified planning. The episode wraps with audience questions on umbrella policies, retirement bond ladders, and sm...

In this episode of Talking Real Money, Don and Tom dive into the latest crypto chaos, pushing back against Ric Edelman’s bold prediction that ETFs will vanish within five years due to tokenization. They explain why that claim is both misleading and premature. Callers ask about tax shelters disguised as life insurance, sketchy “Tax Act 2020” gimmicks, trust issues with advisors, and the realities of Roth conversions and the pro-rata rule. They also revisit the case for holding Bitcoin—and why it’s still mostly a speculative play, not a currency. As always, the tone is skeptical, the advice is candid...

Despite lousy headlines—tariffs, weak earnings, flat revenues—the market keeps climbing. Don and Tom explain why trying to guess the “why” behind short-term moves is a fool’s errand, and why global diversification (including those long-shunned international small caps) is paying off. Listeners call in with smart, complex questions: million-dollar leftover 529s, the viability of the Hagerty Index for collectibles, catastrophic long-term care insurance, and a 401(k) loan vs. credit union loan for home repairs. The show wraps with heartfelt praise, a Mitch Albom-inspired moment, and confirmation: yes, listeners are thinking differently—and smarter—about money.

0:04 Market’s up, h...

Don takes a fiscal detour into the world of AI, introducing his ChatGPT co-host “Cath” in a strikingly lifelike discussion about the future of jobs, the role of artificial intelligence in our lives, and how we can adapt to massive changes already underway. The episode blends curiosity, caution, and practical insight—with a historical twist that ties today’s tech upheaval to the Luddite resistance of the 19th century. It’s a deeply personal, slightly spooky, and forward-looking edition of Talking Real Money.

0:04 Don opens solo and explains how AI (Cath) became his creative partner

1:20 What ChatG...

Don flies solo for another Question-and-Answer Friday (not Freaky Friday… despite Hollywood’s best efforts). Listener questions cover everything from Roth IRA choices for young investors to tax loss harvesting and reducing portfolio volatility with bond allocations. Don breaks down the pros and cons of popular ETFs, explains the benefits of tilting toward small and value, and gently guides a listener away from a pricey Fidelity fund. He also reaffirms that tax loss harvesting is a two-account job and urges investors to rebalance based on total portfolio risk—not just account type.

0:04 Don rails against yet another Freaky...

Don and Tom explore the value of changing your mind in the face of new data—financial and otherwise. Sparked by Christine Benz’s recent Morningstar piece, they reflect on how their own views on DIY investing, target date funds, and even TIPS have evolved over time. Listener questions cover annuity taxes, Bitcoin inflation claims, covered call ETFs, and whether CDs beat bond funds in retirement. Grumpiness levels: elevated but entertaining.

0:04 Flexibility in finance: Why it’s okay to change your mind

1:16 Christine Benz says she’s rethinking the DIY retirement approach

2:48 The underrat...

Don and Tom defend the long-maligned 60/40 portfolio, diving into a 150-year Morningstar study that reveals its lower volatility and emotional survivability—even if it underperforms an all-stock portfolio over time. They tackle fixed indexed annuities head-on, debunking the myth of market returns without risk, citing high commissions, surrender charges, lack of liquidity, and poor transparency. Several listener calls highlight confusion over annuity strategies and Roth vs. pre-tax retirement contributions, including a deep dive from a New York City teacher juggling pensions, 403(b)/457 plans, and Roth conversions under new IRS rules. The show wraps with a playful rant about birthday fr...