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ASYMMETRY® Observations are Mike Shell’s observations of all things asymmetry, asymmetric risk/reward, asymmetric payoffs, and asymmetric investment returns.


Markets Aren't Driven by Averages Thumbnail

Markets Aren't Driven by Averages

Most portfolios are built on averages and optimization. But markets don’t move on averages—and investors don’t live through drawdowns like a spreadsheet assumes. Under pressure, loss aversion changes decisions in predictable ways: winners get cut too early, losers get held too long, and volatility clusters. The real risk isn’t just market risk. It’s behavioral risk. That’s why we design systematic risk management that defines downside in advance and lets upside trends compound.

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VIX Term Structure: The Hidden Edge in Market Complacency Thumbnail

VIX Term Structure: The Hidden Edge in Market Complacency

The steep contango in the VIX futures curve signals market complacency—but also reveals an asymmetric opportunity. This post explores how volatility suppression breeds fragility, why tail risk is mispriced during calm regimes, and how long-volatility positions can deliver convex payoffs when the curve snaps.

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Exit Planning Is the Rotation Event Thumbnail

Exit Planning Is the Rotation Event

Exit planning isn’t about retirement — it’s the rotation event that moves business owners from effort-based income to capital-driven freedom. This ASYMMETRY® Observation explains why selling a business is only the beginning, and how engineered risk management keeps owners off the treadmill for good.

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