Individual options provide value. Option portfolios create antifragility.
Correlated vs. Uncorrelated Options
Like financial portfolios, option portfolios require correlation analysis.
Robert's correlation matrix: - Negatively correlated: Tech skills vs. traditional expertise - Uncorrelated: Geographic options vs. skill options - Positively correlated: Network options vs. opportunity access
He built portfolios with negative and zero correlations for true diversification.
The Barbell Option Portfolio
Applying barbell thinking to options creates robust portfolios.
Jennifer's option barbell: - Safe options: Professional certifications, stable relationships, proven skills - Speculative options: Startup equity, experimental projects, frontier knowledge - Empty middle: No moderate options consuming resources without extreme potential
This structure provided both security and unlimited upside.
Dynamic Option Rebalancing
Option portfolios require active management as conditions change.
William's rebalancing triggers: - Value realization: Exercise and replace - Decay detection: Refresh or abandon - Correlation shifts: Adjust portfolio mix - New opportunities: Integrate strategically - Resource changes: Resize positions
Regular rebalancing maintained optimal option exposure.