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Sept. 16, 2025

AI Advice

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 cos...

Show Notes

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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