Ep31 - A Well-Endowed Trader with Some Issues

In this episode of Wealth Building with Options, host Dan Passarelli dives into one of the most powerful – and often overlooked – forces shaping trading decisions: the endowment effect. This behavioral economics concept explains why we tend to overvalue what we already own, and why that bias can hold traders and investors back from making better choices.

Drawing on research from Richard Thaler and examples ranging from coffee mugs to Super Bowl tickets, Dan shows how the endowment effect plays out in real-world trading—especially when running strategies like the wheel, covered calls, and cash-secured puts. He explores how our brains are wired against discipline, why letting go of a position feels harder than it should, and how traders can use tools like the “Would I do it now?” rule to cut through bias.

From Catholic confessions to Chicago hot dogs, from historical revolutions to behavioral finance studies, Dan blends humor, history, and hard-hitting trading lessons into a thought-provoking conversation that will help you rethink how you value your trades.

What You’ll Discover in This Episode:

• Why the endowment effect influences nearly every investor’s decisions.


• How behavioral economics challenges the assumptions of classical economics.


• The “Would I do it now?” rule for evaluating whether to keep or close a trade.


• Why rolling covered calls or puts can optimize outcomes over simply holding.


• How passive wheel traders differ from active wheel traders—and which approach may suit you best.


• Why predicting volatility is often easier (and more profitable) than predicting stock prices.

Key Takeaways:

• The brain is wired to make us cling to losing trades, but traders can retrain their decision-making process.


• Anchoring decisions to specific times or rules improves discipline and consistency.


• The wheel strategy can be profitable as a passive system, but active adjustments often lead to better returns.


• Options are often overpriced—creating opportunities for traders who understand risk premiums.

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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