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 questions, and steering clear of high-commission products.

1:02 NYT & Yahoo reports on AI financial advice

1:53 Cath GPT joins live, discusses safe AI uses

3:58 Privacy concerns and data recency limits

6:22 Why AI is bad for stock trading advice

6:50 Don confirms Cath recommends index investing

8:14 Warning about sycophancy — always ask for sources

8:38 Caller Josh: pivoting from commercial property to stock market

10:32 Don: planning first, lump sum > DCA

13:23 Caller Greg: inherited assets, Roth conversions, AVGE timeframe, bond/CD ladders

17:20 Don urges no market timing on conversions

22:50 Caller Brian: small-cap value, AVUV vs. Russell 2000, Merriman strategy

28:07 Don: simplify, AVUV fine but optional

29:43 Caller Jason: harvesting gains in low-income year, Don urges diversification

33:03 Caller: backdoor Roth timing — lump sum beats DCA

34:35 Don jokes about October crashes

37:59 Caller Tim: best annuity is SPIA, avoids “legacy funds”

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