Talking Real Money - Investing Talk

Latest Episodes:

Ep. 1716: Illiquid Alternatives Aug 27, 2025

Show notes

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 mom
0:51 Liquidity lessons from elite college endowments and alternatives
2:56 Why liquidity matters for retirement and emergencies
6:21 Caller Rich: $2M assets, pension, Social Security, annuity concerns, Tom warns against deferred income annuities
11:46 Caller Will: real estate commissions after lawsuits, Tom says budget ~10% of sale price
15:09 Tom warns about too-good-to-be-true “8% guarantees”
16:26 Caller Catherine: asks why Vanguard lacks a balanced ETF; Tom suggests DIY mix or wait for rollout
21:40 Tom stresses ignoring TikTok “advice” and staying the course; examples of small-cap rebounds
25:31 Global small/value stocks outperform S&P this year—own them all
26:49 Caller Joe: 100% S&P 500 allocation in retirement accounts; Tom warns about concentration, suggests global diversification
32:56 Caller Alan: Wellington Fund vs. more equities; Tom favors index funds and broader global exposure
37:28 Risk quiz, portfolio planning, and building for your own needs vs. peer influence
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Ep. 1715: Making Life Better Aug 26, 2025

Show notes

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, and putting money in its proper place.
0:04 Don out visiting his mom, Tom hosts solo
0:48 Market news and Appella Wealth annual client event recap
2:36 What clients really talk about: travel, family, weather—not money
3:25 Why clients worry less about markets when planning is in place
5:59 The importance of advisors (or DIY) in managing rebalancing, taxes, RMDs
7:09 Caller Bill (MN): Renew $200k CDs at 4% vs move into bond fund
11:25 Caller Jim (TX): High-fee muni closed-end funds, whether to sell
13:20 Caller Tom (VA): Planning Roth IRA allocations, target-date funds at Fidelity
18:53 Caller Gene (MD): $8M estate, big mutual fund gains, reducing taxes for heirs
28:12 Caller Bernadette (WA): Regrets annuity with USAA, options for moving it
31:18 Tom’s guidance: why annuities disappoint and fiduciary help matters
32:41 How to “put money in its place” if you’re a DIY investor
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Ep. 1714: Should Have Yielded Aug 25, 2025

Show notes

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 investigation findings
2:26 Losses and watch-list numbers from their portfolio
3:48 Investors chasing 20% returns and Adam Neumann connection
5:01 Private investments pitched as “smoother sailing”
6:14 Throwback to 2022 TRM episode warning about Yieldstreet
7:38 False promises of 8% “distributions” and return of capital
9:10 FBI and SEC probes; fees, liquidity issues, and risks
10:33 Why magical investments work… until they don’t
12:22 Don’s “Financial Fysics” rule: only 3 ways to make money
14:24 Private credit in 401(k)s—why Don hates the idea
15:36 Listener Q: Roth conversion strategy before retirement
17:17 Five-year rule confusion and conversion clarifications
18:52 Why splitting Roth and pre-tax can make sense
20:09 Listener Q: Roth vs. pre-tax for high earners in California
22:08 The need for predictive tax planning with large balances
22:26 Wealth requires planning, not winging it
24:12 Wrapping up—Yieldstreet’s lesson and Roth themes
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Ep. 1713: Busy Day of Q&A Aug 22, 2025

Show notes

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
1:14 Listener note on Mr. Bates vs. the Post Office documentary
2:49 Ivan asks about when to buy umbrella insurance
6:23 How to send in questions and live call-in info
6:41 Listener asks about rebalancing across 401k, Roth, taxable, and HSA
10:02 Jeff asks about U.S. vs. international small-cap value ETFs and missing T-shirts
12:34 Mike from Colorado describes using ChatGPT for Roth conversion and withdrawal planning; Don and Kath discuss AI’s impact on financial advice and SEC regulation
20:46 Ed from North Carolina asks about fiduciary fees, IRA penalties, and the new client experience at Appella
23:27 Advisor meeting cadence and availability explained
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Ep. 1712: Still Rising Aug 21, 2025

Show notes

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 plea to get financial plans in order as fall approaches.
0:04 Why has the market been so resilient for nearly 20 years?
1:01 Buy-the-dip culture vs. true bear market experience
2:20 Recalling the 2007–09 crash and its emotional aftermath
3:15 Younger investors haven’t seen long-term pain—yet
4:07 A history of “new paradigm” optimism before brutal downturns
5:30 Rising 401k balances vs. uncomfortable overconfidence
5:46 Buying the dip… or being the dip?
7:21 The savior during lost decades: diversification
8:45 “Winter is coming”—how to prepare like a Northerner
9:34 The return of bonds and rechecking your allocations
10:20 Hidden risks of U.S. stock concentration
11:14 Take 20%–50% off your portfolio mentally—it’s not all yours
11:44 Listener questions: mic technique and financial reality check
13:24 The movie theater saga: terrible options and funny reviews
17:00 Listener Q: Calendar rebalancing vs. opportunistic rebalancing
18:50 Listener Q: Selling winners vs. minimizing capital gains
20:10 Listener Q: Comparing AVDE, AVNM, and Dimensional ETFs
24:58 Tax-loss harvesting with Avantis and Dimensional
26:24 Amazon’s latest 3%-fresh movie disaster
28:12 Time to get your financial life in order—fall is coming
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Ep. 1711: Mind the Gap Aug 20, 2025

Show notes

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. market returns: why we underperform
1:32 Morningstar’s “Mind the Gap” study explained
2:59 Behavioral mistakes: trading too much, chasing sectors, style drift
4:48 Volatile funds lead to worse investor outcomes
6:39 Frank asks: What’s wrong with 403(b) plans?
9:14 The real problem with 403(b)s: annuities and teacher exploitation
13:12 Why annuities don’t belong in tax-deferred plans
14:04 How to escape a bad 403(b): 403bwise.org and “green light” plans
15:45 Listener Gabriel: Is S&P 500 enough for a long-term portfolio?
17:56 VOO vs. VT: Why global diversification matters
19:39 Concentration risk and emotional investing
22:08 Listener Garrett: Planning for a second home in retirement
25:10 Real estate reality: owning two homes isn’t always ideal
28:45 Listener Nina: Clarifying the senior tax deduction
30:07 Listener Jim: Where should I invest a $1M windfall?
32:47 Long-term strategy: globally diversified stock portfolios
34:27 Listener Lori: How to unwind a concentrated tech stock portfolio
35:20 Altria: A century of sin stocks and their surprising holdings
37:00 Program note: Tom solo next week—please call in!
38:46 English is weird: talk vs. tok, though vs. thru
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Ep. 1710: Investing Trivia Time Aug 19, 2025

Show notes

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 years? (Hint: it wasn’t Apple)
4:19 Why Altria (Philip Morris) beat the rest
5:31 Berkshire Hathaway drops 99%—would Buffett still beat the market?
6:37 Show mission: make investing simple, not complex
8:28 Caller Valerie: Investing for a daughter with disabilities using Vanguard ETFs
10:24 Portfolio review and discussion of special needs trusts
11:20 Structuring brokerage accounts with trust beneficiaries
13:31 Caller Steve: Roth IRAs for sons, target date vs. all-equity funds
14:36 Tom critiques Schwab’s target date funds—Vanguard preferred
16:20 Future value of $10K over 50 years at 10%—retirement math
17:20 Caller Sam: Can he gift stock into a Roth IRA? (Spoiler: No, but workarounds exist)
18:59 Economist “Felicity Foresight” exercise—guess the ending balance after 100 years of perfect timing
20:34 The shocking power of compound returns: $10 quintillion
22:15 Geography jokes, the U.S. “Middle East,” and why cruises go to Juneau
23:39 Written Question (Bruce): Keeping emergency funds in a Schwab money market fund
25:10 Online bank trust vs. FDIC insurance—why it’s safe
27:51 Don calls Tom a “premature curmudgeon”
28:30 Caller West: Should he add SGOV to his BND bond portfolio?
29:52 BND vs SGOV explained—behavior during rate changes
30:37 Back to WSJ quiz: investing trivia and early company names
31:31 Bezos almost named Amazon “Kadabra”; Google was almost “Backrub”
33:20 What’s a googol? And why Google isn’t even the biggest number
34:48 Shoeshine story: how Joe Kennedy dodged the ‘29 crash
36:39 Caller Diana: Investing for four grandkids—gold coins vs stocks
38:41 Why diversified ETFs beat Boeing stock or gold coins
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Ep. 1709: Social Insecurity? Aug 18, 2025

Show notes

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 belong only in tax-deferred accounts. The show ends on a lighter note with a detour into the surprising origin stories of Cocoa Beach, Florida—and a well-earned nod to Don’s daughter for her killer disclaimer voiceover.
0:04 Tom’s Goldilocks routine: too hot, too cold, never just right
1:05 Why early Social Security claims can be financially tragic
2:11 Top emotional excuses people use to claim early
3:19 The 2033 funding deadline and how Congress will likely delay action
4:16 Misconceptions about break-even math and spousal survivor benefits
5:01 Real example: Don’s $49K vs. $58K annual benefit if he waits
6:55 The “just want my money” crowd: emotional logic at its worst
8:13 Average claiming age has improved, but still too early for most
9:38 Can you bridge the income gap to delay claiming? Not if you’re broke
10:55 Permanent 30% cut if you claim at 62 vs. full retirement age
11:52 Why working longer might be the best—and only—solution
13:12 Retirement isn’t a permavacation: the mental toll of early retirement
14:18 Emotion vs. planning: the real battle in financial decisions
14:41 Listener Q: KCIS hybrid pension pitch = pure annuity sales
16:17 Indexed annuities, tax-free income claims, and SEC loopholes
17:50 Listener Q: AVNM vs. AVGE – how to structure your global ETF allocation
18:50 AVGE = one fund; AVNM + AVUS = smarter two-fund DIY
19:59 Listener Q: iShares target-date ETFs and the risk of fund closure
21:17 Why target-date funds don’t belong in taxable accounts
22:19 Why is Cocoa Beach called Cocoa? Three weird theories
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Ep. 1708: More Money Answers Aug 15, 2025

Show notes

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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Ep. 1707: Pecuniary Presidents Aug 14, 2025

Show notes

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 political financial activity, and the importance of aligned values in relationships for financial success.
0:05 Tom introduces Megan Gorman and her book All the President’s Money
1:16 Is there a link between being a good president and good with money?
2:16 Warren G. Harding as a bad president but skilled entrepreneur
3:22 Biggest lessons from presidents’ finances—marrying up and aligning values
5:56 Trump marriages and shared transactional values
6:15 How presidents historically made their money—land speculation, inheritance, entrepreneurship
8:40 Nixon’s failed frozen juice business and debt repayment
10:43 Eisenhower’s emotional control, poker skills, and marrying up
12:43 Gerald Ford as the master of the post-presidency pivot into celebrity and corporate roles
15:12 Debate over financial conflicts for presidents and members of Congress
17:13 Clinton financial evolution from poor money management to high net worth
19:38 The role of grit—Herbert Hoover’s rise from orphan to wealthy mining engineer
21:39 Woodrow Wilson’s lack of hustle contrasted with other hard-working presidents
22:30 Biggest takeaway—financial principles haven’t changed, but the American dream is harder to achieve today
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