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Selling Naked Puts — Why I NEVER Hold Long-Dated Ones (The Rule Protecting My $2.8M)

Aug 7, 2026 · 13m

Summary

David Jaffe explains why selling long-dated naked puts is dangerous due to extended risk exposure and margin call potential during market crashes. He advocates for his "short the risk, long the reward" rule, keeping put obligations short-term while maintaining long-term upside through call debit spreads. Jaffe demonstrates this strategy with real trades on Micron and SMH, showing how rolling positions in can reduce risk while collecting credits.

Topics discussed

Serval AI ad: Automating IT workflows Intro: The rule of short risk, long reward Why long-dated naked puts are dangerous How crashes inflate long-dated put risk Case study: Rolling Micron puts to reduce risk SMH trade structure: Financing upside with short risk How rolling works and the theta decay advantage The margin call trap and portfolio verification Live plan: Rolling SMH puts to shrink risk window Conclusion, host bio, and call to action Wayfair Halloween decor advertisement
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