Ep25 - Party Like A Pachyderm

In this episode, Dan explores the strategic rationale behind trading long-term buy-writes, even when they offer lower theta compared to shorter-term options. While conventional wisdom might suggest optimizing for higher theta, Dan lays out a compelling case for why going long may actually lead to more consistent, reliable results—especially when thinking like an investor rather than a trader.

What You’ll Learn

• Short-Term vs. Long-Term Buy-Writes: How these similar-looking strategies differ substantially in execution and outcome.
• Why Theta Isn’t Everything: Dan explains why he sometimes sacrifices short-term theta to gain longer-term predictability and more investor-style returns.
• The Tomato vs. Tomatillo Analogy: A lighthearted but powerful metaphor showing how two strategies that look the same can behave very differently.
• The Case Study: AEO (American Eagle Outfitters): A real-life example of a long-term buy-write trade:
  • Entry at $10.96
  • Selling Jan 2026 $11 calls for $1.80
  • Breakeven: $9.16
  • Static return: 16.4%
  • If-called return: 16.8%
  • Annualized return: 26.2%
• Understanding Volatility Over Time: Why longer-term predictions can be more reliable due to how volatility “smooths out” over time.
• Framing Buy-Writes Like Interest-Bearing Assets: Dan explains how viewing these positions like CDs or bonds (despite their risk) helps him stay grounded as a long-term investor.
• The Role of Interest Rates in Longer-Term Options: How rising interest rates affect call pricing and open up opportunities to sell higher strikes at compelling premiums.

Key Takeaways

• Long-term buy-writes may offer lower theta, but they provide better downside protection, reduced maintenance, and can function more like an investment than a trade.
• Annualized return is a helpful—but sometimes misleading—lens. Use it to evaluate risk-adjusted opportunity but avoid relying on it to boost ego.
• Selling slightly higher strikes in today’s interest rate environment can lead to “best of both worlds” scenarios with solid premium and upside potential.

Mentioned In This Episode

• Ticker: AEO – American Eagle Outfitters Concepts: Theta, Volatility Cone, Annualized Return, Interest Rates & Rho, Covered Calls, LEAPS
• Tool: Thinkorswim

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Shout-Outs

Special thanks to supporters including Alex H., Bill H., Paul P., Sean K., Steve D., Myron, Glen K., Spencer, and many others. Your backing keeps the show running and the content flowing.

Next Episode Preview

Dan welcomes a special guest to talk about a powerful addition to the buy-write strategy discussed today. Don't miss Episode 26!

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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