About this episode
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 Learn more about your ad choices. Visit megaphone.fm/adchoices