How Losing $500K in ‘08 Led One Trader to a Different Kind of Portfolio, with Jared Dillian

Jared Dillian recounts losing $500,000 in Lehman Brothers stock during the 2008 collapse and the portfolio philosophy he built afterward. He explains why selling company stock immediately is critical, how low living expenses gave him the freedom to start a business, and how a simple Las Vegas test can reveal your true risk tolerance. Dillian advocates for a five-way portfolio—stocks, bonds, cash, gold, and real estate—that fell only 9.8% in 2008, with a deliberate 20% cash cushion for optionality and psychological stability. The conversation also covers bond yields as economic warning signals and why half of retirees claim Social Security at 62 despite financial trade-offs.