Jason Buck, founder and CIO of Mutiny Funds, joins Infinite Loops to tell the painful and darkly funny story of how the 2007–2008 crash destroyed his real estate business, wiped out his paper wealth, and taught him one of the hardest lessons in markets: being right is not the same thing as making money.
Jason explains how he went from real estate developer to volatility trader and eventually built his philosophy around survival, resilience, and the “Cockroach Portfolio.” He and Jim explore why true diversification always feels uncomfortable, why human behavior is the most persistent source of market mistakes, and why investing beliefs often resemble religion.
TIMESTAMPS
0:00 Intro
0:56 Jason Buck’s Circuitous Career
6:50 The Crash That Changed Everything
10:27 Investing as Religion
13:36 Why Diversification Should Hurt
22:29 The Cockroach Portfolio
39:01 Everyone Was Complicit in 2008
46:20 Right About the Crash, Wrong Trade
1:13:37 Walking Across Nihilism
1:57:28 Jason’s Final Question Responses
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