Talking Real Money - Investing Talk Podcast

In this Friday Q&A episode, Don answers a wide range of listener questions, covering everything from market timing behavior and condo pitfalls to portfolio simplification and strategic debt repayment. He offers heartfelt financial guidance with his usual mix of candor and compassionincluding a personal confession about his own Social Security decision. Plus, he pleads (just a little) for positive Apple Podcast reviews to combat the crypto bros and insurance hawks.

0:04Friday Q&A intro and how to submit voice questions

1:40What do market-timing traders actuallydowith their cash during volatility?

4:25Are condos and co-ops really the devil? Why Dons skeptical

9:46Listener shares Don sparked his investing journey in the 90s

11:15Should a friend drop her advisor for a robo-platformor go DIY with VT/BND?

17:32Why Don prefers AVGE over VTI for broader, smarter diversification

18:15Tiny differences in fees can mean big long-term results

18:58Active-duty military caller: Should I pay off debt using savings and ditch whole life?

24:08Listener nearing 70: Should I freeze my Social Security or just enjoy it now?

26:46Dons honest confession abouthisown SS filing decision

27:52Why good reviews matter (and how to fight the crypto/insurance trolls)

29:43Call live on Saturdays while Tom vacations again Learn more about your ad choices. Visit megaphone.fm/adchoices

A chaotic day leads Don into a deep (and entertaining) dive into the futility of market timing, spurred by a recent Morningstar article on Pacers Trendpilot ETF. Don and Tom break down the mechanics of the funds strategy, its underperformance compared to a simple 60/40 portfolio, and the long-term cost of trying to avoid downturns. Listener questions bring up diversification, Roth IRAs, and the eternal struggle with ticker symbols. Plus, a special heads-up for federal employees about an upcoming webinar. And yes, kilt ventilation is discussed.

0:04It never rains but it pours rant, helicopters, kilts, and chaos

2:02Welcome and the evolution from market timing believers to skeptics

3:13Trendpilot ETFs moving average strategy explained (kind of)

5:45Morningstar says: strategy failed, underperformed S&P by 5% annually

6:5897-year 60/40 portfolio beats Trendpilot in return and volatility

8:322020 example: Trendpilot missed the 38% reboundouch

9:59Why market timing fails most investors over time

11:05Loss aversion vs. long-term strategy with fixed income

13:08Trendpilots $3.3B in AUMbut it still doesnt justify market timing

14:23Listener mail: VTEB vs VTBE, Series 65 textbook gems, diversification

18:26How much in a single stock? Almost none

19:10Roth IRA allocation questionAVUS, DFIV, AVUV, and maybe just AVGE

22:24One-fund to rule them all: AVGE breaks it down across 15 funds

24:11Federal employee webinar pitch June 7 at appellowealth.com

25:39Wrapping up with call-in info, dreams about forgetting the phone number, and kilts (again) Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom unpack Morningstars latest 5 of the Best investing methods, praising the simplicity of balanced and target-date funds but warning against high-fee versions. They emphasize that no portfolio fits everyone and push for low-cost index solutions. Listeners call in with 401k rollover questions and political discomfort around financial firmssparking a candid, occasionally funny chat about ethics, emotions, and retirement realities. The episode wraps with a challenge to fix Social Security and a request for more five-star Apple Podcast reviews before Don dies on the mic.

1:07Morningstars 5 of the Best investing methods reviewed

1:48Balanced funds and target-date funds: pros and cautions

2:48Three-fund and custom-fit portfolios discussed

4:08Critique of Morningstars recommended balanced funds

6:19Expense ratios of target-date funds and better alternatives

7:17Morningstars risky allocation advice near retirement

9:17Why one-size-fits-all portfolios dont work

10:14Caller Sally: Should we move from T. Rowe Price 401k?

12:56T. Rowe Price vs. Vanguard fee comparison

14:03How to roll over a 401k into an IRA

17:39Custom portfolios vs. simplicity and human behavior

21:42Caller Lynn: Political discomfort with Schwab as custodian

26:26Keeping an advisor despite ideological concerns

28:38Raising the retirement age: Denmark vs. U.S.

32:48Fixing Social Security: remove the wage cap

35:29Listener reviews, crypto hate, and ETF conspiracy theories Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode of Talking Real Money, Don and Tom reluctantly return to the topic of Bitcoin, using its recent price spike to explore deeper questions about market efficiency, irrational investor behavior, and the legitimacy of crypto as an investment. With nods to Eugene Fama, Cliff Asness, and some well-aimed skepticism, the duo debates whether price reflects value or just hype. Alongside listener calls from California, Canada, and North Carolina, they address portfolio allocation, pension rollover strategies, and even debunk gold’s glitter as a bond replacement—punctuated by a truly explosive segment on “FartCoin.” Yes, really.

0:56 Tom and Don reluctantly dive into Bitcoin and crypto’s price spike

1:37 Are crypto markets truly efficient? Academia vs. reality

2:44 Price goes up because price went up? Questioning efficient market theory

4:17 Cliff Asness on how social media distorts collective investment judgment

6:23 Don restates the three ways to make money: work, luck, dishonesty

6:50 Harvard-style debate: Can markets be truly efficient?

8:24 Rational ignorance and emotional investing behavior

9:36 Fama says Bitcoin will go to zero within a decade

10:30 Dogecoin and meme coins: speculative absurdity vs. real purpose

12:06 Investment principles: Diversify, plan, ignore hype

13:51 Tom and Don are ‘contrary indicators’—Bitcoin jokes ensue

14:14 Call: Clinton in CA asks where to put pension payments he doesn’t need yet

16:13 Investment advice for 5-year+ horizon: high yield/cash/bond/stock mix

17:48 Tom’s wife builds a wheelbarrow, financial education “nonprofit” mailer

19:11 Crypto joke segment: FartCoin rises to $3.50… and the bad puns begin

22:02 Call: Jeff from Canada on gold returns vs. bond stability

24:24 Should gold be part of a diversified portfolio? Historical returns debunked

28:39 Gold bar nostalgia vs. investment logic

29:58 TRM T-shirt giveaway and gold vs. bonds as ‘cool’ vs. smart

31:30 Call: Zach in NC—Should he roll old 401(k) into state pension plan?

33:10 Breakdown of NC pension plan fund options and a 90/10 allocation strategy

36:03 Don signs up for a “non-sales” financial education class by an unlicensed guy

37:50 Red flags: financial advisor not registered anywhere, mystery deepens Learn more about your ad choices. Visit megaphone.fm/adchoices

Don and Tom dive into a new study showing the average investor spends just six minutes researching a stock—most of it just watching the price move. From gut feelings to hometown bias, they unpack why individual stock picking is often driven by emotion, not logic. Along the way, they skewer myths about control, tax efficiency, and the Warren Buffett fantasy. Listener questions cover Roth 401k rollovers, Roth conversion timing, and Fidelity’s commingled active target-date funds—and why none of them beat a good portfolio of low-cost ETFs.

0:04 Stock picking takes 6 minutes, says NYU study

1:09 Why people pick stocks without research

1:56 Risk analysis ignored by most investors

2:57 The illusion of gut instinct investing

4:22 Beating the market is harder than it looks

5:44 The fantasy of picking only “good” stocks

7:10 The control myth and cost of stock picking

8:29 Buffett’s process vs. your fantasy

9:53 The illusion of control and tax myths

10:58 What real diversification means

12:11 You’re wasting time, not just money

13:11 Emotion makes individual stock picking harder

13:59 Familiarity bias in hometown investing

15:21 Listener Q1: Roth 401k rollover planning

16:27 How many ETFs should a multimillion Roth have?

17:59 Get fiduciary help or risk being sold garbage

18:21 Listener Q2: Roth conversion tax trap

20:17 RMDs aren’t the enemy—bad Roth math is

20:29 Listener Q3: Fidelity commingled target-date fund

21:35 Why active target funds fail investors

22:07 Better option: Three low-cost ETFs instead Learn more about your ad choices. Visit megaphone.fm/adchoices