Behavior Prompting

Don and Tom tackle the creeping role of AI in financial advice—highlighting Vanguard’s new “nudges” on its platform—before pivoting into lively listener calls. The show explores the balance between saving and living (including an $800K earner debating a bigger house), the risks of high-yield gimmick ETFs like QQQI, the simplicity of age-based 529 plans, and the murky rules around paying kids into Roth IRAs. Humor, skepticism, and practical guidance keep the conversation grounded, with a side of leaf blowers, Italian villas, and Tom’s inevitable puns.

0:10 Don’s dramatic AI apocalypse intro and Vanguard “nudges”

1:20 Squarespace rant: how customer service died

4:13 Vanguard limiting fund lists—bias toward active funds?

6:22 AI is coming for investing advice

6:35 Listener call: $800K household, cheap mortgage, “living life” vs upgrading home

10:22 House affordability rules: 25–30% PITI, low-rate lock-in dilemma

12:19 Call from Jim in Bellevue: QQQI high-yield ETF

13:44 Why covered call income funds are risky, volatile, and gimmicky

17:41 Tech focus, March 2000 parallels, why diversification beats chasing yield

19:29 Covered call strategies—why they lose upside and add complexity

22:50 Listener email from Shauna: which Utah 529 portfolio to pick

24:36 Best choice = age-based glide path, simplicity and cost advantages

26:13 Follow-up caller: Roth IRAs for kids, risk of inflated wages and IRS scrutiny

29:24 Who checks wages? IRS shutdown jokes, K-1 confusions, AI tax analysis fail