As the year crawls to a close, Don and Tom torch the ritual of “New Year, New You” financial advice and take aim at the endless lists of five things you must do next year. They break down why year-end deadlines are mostly psychological theater, why prediction-based investing is a sucker’s game, and how even AI—when pressed—admits the truth: diversification beats cleverness, patience beats prediction, and complexity usually hides higher costs and worse outcomes. Along the way, they tackle 529 plans, proposed “Trump accounts,” Roth strategies for kids and retirees, factor investing myths, and the ongoing media obsession with whatever already went up last year. It’s a holiday episode for skeptics, cynics, and anyone tired of being told that this is finally the year everything changes.

0:04 Holiday cynicism, snow, trees plotting revenge, and Don declares war on Pollyanna finance

1:19 Year-end obsession: why December 31 is an arbitrary psychological trap

2:29 Why “five things to do in the new year” articles exist—and why they’re mostly nonsense

3:55 Asking AI for financial advice and accidentally getting decent answers

4:18 Don’s AI delivers brutal honesty: complexity isn’t sophistication, it’s camouflage

5:54 The most dangerous question of all: “What should I invest in next year?”

6:06 Everyone’s favorite prediction: AI stocks (again), and why that’s backward logic

6:29 The real answer: globally diversified equities, patiently held and largely ignored

8:07 Motley Fool, Morningstar, defense stocks, and the annual prediction circus

9:29 AI’s final verdict: everything after diversification is garnish people argue about on TV

10:33 Listener Brian on New York 529 plans, state tax deductions, and Roth rollover flexibility

11:30 How aggressive is too aggressive for a child’s college savings?

12:45 Why age-based 529 portfolios are often far more conservative than parents realize

14:10 When college money should actually shift to safety—and when it shouldn’t

15:43 The mysterious “Trump accounts”: proposed rules, confusion, and missing details

16:56 Tax treatment uncertainty, Roth myths, and why free money is still free money

18:39 Clear conclusion: this account doesn’t exist yet and nobody knows the real rules

20:05 Don’s full rant: pandering policies, financial clutter, and unnecessary complexity

22:07 Listener Larry on starting a Roth IRA for a 19-year-old with a one-fund solution

22:47 AVGE explained: global, factor-tilted, low-cost, and boring in the best way

24:15 AVGE vs. Vanguard Total World: interest vs. necessity

25:26 AVGE underperformance criticism and why one-year returns are meaningless

28:26 Why Avantis funds aren’t trying to “pick winners” and never claimed to

31:32 Listener Caroline on retirement withdrawals, IRAs, Roths, and tax reality

33:11 The unavoidable truth: you’ll pay taxes—now or later

35:43 How (and where) listeners can actually rate the show

38:01 Politics, labels, John Oliver, and why nuance is apparently illegal now

38:54 Capitalism, fairness, and refusing ideological purity tests

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