Don and Tom open with an honest reflection on market déjà vu—how today’s investing climate echoes the speculative excesses of 1929 and 2008. Citing Andrew Ross Sorkin’s new book 1929: Inside the Greatest Crash in Wall Street History, they discuss the modern “financialization” wave: private equity, venture capital, crypto, and private credit being repackaged for retail investors and even 401(k)s, often under looser regulation. They warn listeners about “mark to make-believe” valuations and Wall Street’s relentless drive to sell complexity to the masses. The conversation moves from cautionary history (leveraged trusts of 1929, margin loans, and subprime mortgages) to present-day parallels like Bitcoin ETFs and private-market tokens. The takeaway: avoid opaque, speculative products; stick with transparent, low-cost diversification. In the Q&A, they answer listener questions about simplifying global portfolios with VT vs. VTI/VXUS, and about selling or donating concentrated stock positions from employee plans.

0:04 Opening disclaimers and acknowledgment that the episode isn’t meant to scare investors

1:18 Historical parallels—1929, 1987, 2008—and the feeling of “market déjà vu”

2:10 Introducing Andrew Ross Sorkin’s new book 1929 and his NYT column on modern speculation

3:20 Financialization and the loosening of investor protections in the 2020s

4:33 Wall Street’s constant invention of confusing products that favor sellers

4:58 Robinhood’s Vlad Tenev and the illusion of democratizing risk

6:12 Lowering the barriers to private markets and what that means for investors

7:26 Echoes of 1929: leveraged ETFs, margin-like structures, and “Russian-doll” debt

8:29 The perils of leverage and speed of modern market declines

9:02 Private-market tokens and the “mark-to-make-believe” problem

10:25 Overvaluation, lack of liquidity, and Wall Street’s interest in 401(k) assets

11:41 Historical leverage shifts—from banks to private credit

12:58 Why trusting financial “authorities” can be dangerous

13:32 Emotional honesty: people lie, and investors must self-protect

14:42 Jealousy, lottery-thinking, and envy as behavioral pitfalls

15:36 Investing as elimination—avoid what’s complex, costly, or confusing

16:48 Listener Q&A: two-fund simplicity (VT + BND) vs. multi-ETF tinkering

18:38 The temptation to overweight U.S. equities

20:00 Contrarian case for international exposure (VXUS)

21:15 ESPP stock cleanup: when to sell concentrated holdings

22:44 Charitable giving of appreciated stock for tax efficiency

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