Don and Tom welcome Weston Wellington of Dimensional Funds for a rare and richly insightful conversation covering market volatility, media noise, diversification, and the enduring wisdom of index investing. Weston compares Spam to Motorola, skewers financial hype, and champions simplicity in investing—and yes, he might just sing if you let him. The conversation explores how far the financial industry has evolved (and still has to go), why most investors get in their own way, and whether AI or just good old-fashioned “aggregated intelligence” holds the future of smart money management.

0:04  Don’s surprise “singing telegram” and guest intro
0:53  Weston Wellington on volatility and market uncertainty
2:47  Why volatility is the “price we pay to play”
3:32  The media’s role in investor anxiety
4:57  Should investors act on daily financial advice?
6:15  Portfolio changes should reflect personal changes, not headlines
7:24  Spam vs. Motorola: A lesson in stock picking
9:44  Dimensional’s stance on individual stock ownership
10:02  Diversification as “the closest thing to a free lunch”
11:07  Are alternative investments the new magic bullet?
12:43  Mutual funds vs. ETFs—what works best and when
15:27  Industry evolution: from 8% loads to indexing dominance
18:29  Where Dimensional fits in the modern fund landscape
21:01  AI vs. “aggregated intelligence” in managing portfolios
24:04  How regular people can find real financial advice
25:34  The key to success: Temperament, not timing
26:44  Weston’s side gig as a roving birthday singer
27:58  Why Weston hasn’t been invited lately (and he's lonely)

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