Risk of Ruin

The Character Building Side Effect of Losing

21 snips
Dec 26, 2023
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ADVICE

Seek One-Off Events Where Algorithms Fail

  • Find trades where data-driven models perform poorly and human analysis adds value.
  • Focus on one-off events like elections where unique study yields mispriced options.
ANECDOTE

Beaten Early, Learned Fast At Morgan Stanley

  • Jason started at Morgan Stanley and learned by getting beaten by smarter market participants.
  • That early experience taught him edge capture and market-making fundamentals.
INSIGHT

Black Swan Markets Teach Tail Risk

  • The 2008 crisis created extreme trading opportunities and forced new risk awareness.
  • Witnessing system stress reshaped how Jason evaluates tail risk and sizing.
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