January 20, 2026

Ep50 - That Which Is Measured Is Improved

35 minutes

Dan lays out the core performance metrics that help wheel traders evaluate, compare, and improve covered calls and cash-secured puts. He explains why isolating the option component of returns matters and why annualizing turns “apples to apples.” He also introduces a powerful long-term concept, the cumulative discount effect, where repeated premium collection steadily lowers your effective risk over cycles.

Key Topics

Why measuring trade performance leads to better decision-making

Separating the option “yield” from the stock’s P&L noise

Covered call metrics: static return, annualized yield, if-called return

Covered call reference points: breakeven/cost basis and indifference point

Why time value (extrinsic) is the key input in these formulas

Cash-secured put metrics: skate return on cash and annualized skate yield

Cash-secured put reference points: breakeven/cost basis and indifference point

Comparing cash-secured put yield to other investments (CDs, bonds, etc.)

The cumulative discount effect across wheel cycles

Why cumulative premium can reduce risk and improve Sharpe Ratio

Clarifying “cost basis” vs. tax cost basis

Key Takeaways

Metrics create clarity. You can’t improve what you don’t measure, especially in a strategy built on small edges.

Use time value, not total premium, for true option yield. Extrinsic is what decays and what you’re paid to harvest.

Annualize to compare fairly. Annualized yield lets you compare different expirations and even different underlyings.

Know your outcome scenarios. Static/skate metrics assume no assignment; if-called metrics assume assignment—both matter.

Cumulative discount is the long-game advantage. Over cycles, repeated premiums lower effective entry price, reduce risk and can improve risk-adjusted returns.

“Cost basis” here is conceptual, not tax guidance. Treat these as trading metrics—not tax accounting.

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Learn more about host Dan Passarelli and Market Taker Mentoring: MarketTaker.com

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Disclosure:

Options involve risk and are not suitable for all investors. Prior to buying or selling an option, investors must read Characteristics and Risks of Standardized Options (ODD) which can be found at https://www.theocc.com/company-information/documents-and-archives/options-disclosure-document

Don’t trade with money you are not prepared to lose. Anything discussed on this show is intended to be generalized information and not intended to be a recommendation to buy or sell any security. The host and guests are not familiar with listeners’ specific situations. For trading information relevant to your specific needs, speak with a licensed broker or advisor.

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