Why has the stock market been so persistently resilient despite crises like COVID, wars, and inflation? Don and Tom explore whether the current generation of investors is simply too inexperienced to remember real bear markets—and what that means for the future. They reflect on market history, including the 2000–2009 “lost decade,” and warn against overconfidence and overconcentration in U.S. large caps. The episode covers lessons from diversification, the value of bonds, the illusion of wealth during bull markets, and listener questions about rebalancing strategies, tax-efficient withdrawals, and international fund choices. They wrap up with a hilarious movie segment and a plea to get financial plans in order as fall approaches.

0:04 Why has the market been so resilient for nearly 20 years?

1:01 Buy-the-dip culture vs. true bear market experience

2:20 Recalling the 2007–09 crash and its emotional aftermath

3:15 Younger investors haven’t seen long-term pain—yet

4:07 A history of “new paradigm” optimism before brutal downturns

5:30 Rising 401k balances vs. uncomfortable overconfidence

5:46 Buying the dip… or being the dip?

7:21 The savior during lost decades: diversification

8:45 “Winter is coming”—how to prepare like a Northerner

9:34 The return of bonds and rechecking your allocations

10:20 Hidden risks of U.S. stock concentration

11:14 Take 20%–50% off your portfolio mentally—it’s not all yours

11:44 Listener questions: mic technique and financial reality check

13:24 The movie theater saga: terrible options and funny reviews

17:00 Listener Q: Calendar rebalancing vs. opportunistic rebalancing

18:50 Listener Q: Selling winners vs. minimizing capital gains

20:10 Listener Q: Comparing AVDE, AVNM, and Dimensional ETFs

24:58 Tax-loss harvesting with Avantis and Dimensional

26:24 Amazon’s latest 3%-fresh movie disaster

28:12 Time to get your financial life in order—fall is coming

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