Wealth Building With Options

Ep12 - I've Reached My Limit

Episode Summary:

In this episode, Dan Passarelli breaks down a powerful trading concept: using cash-secured puts as a smarter, more strategic version of limit orders. If you've ever hesitated about assignment or second-guessed a put trade, this episode is for you.

Dan shares real-world stories (including a Vegas twist involving a mastermind event that… wasn’t) and psychological lessons from 7,000+ trading days. He explains why assignment shouldn’t be feared, how premium collection changes the math on your trade entries, and how traders often let emotion sabotage what could be great opportunities.

Later, Dan welcomes back John Kmiecik, a trading coach who’s worked with hundreds (maybe thousands!) of students on mastering this mindset. Together, they explore:

• Why traders often fear assignment more than they should
• How selling puts is like getting paid to place a limit order
• Real trading examples from John (including his recent strategy with Comcast)
• The psychological traps that can derail traders — and how to avoid them
• Tactical advice for identifying price levels where you're truly comfortable owning stock

Key Takeaways:

• Assignment isn’t failure — it's part of the plan when using puts to enter stock positions.
• Cash-secured puts can lower your effective purchase price, even without assignment.
• Psychology is everything. Fear, regret, and hesitation often cost more than any bad trade.
• A put that doesn’t get assigned? You still keep the premium. That’s the hidden win.
• Planning your response before you enter a trade is the key to long-term consistency.

Next Steps: 

• Subscribe to Dan’s Substack, https://wealthbuildingwithoptions.substack.com for Video Extras, trade recaps, and monthly AMA sessions.
• To work with Dan and John you can connect with them at Markettaker.com
• Options involve risk and may not be suitable for all investors. Read Characteristics and Risks of Standardized Options before investing. https://www.theocc.com/getmedia/a151a9ae-d784-4a15-bdeb-23a029f50b70/riskstoc.pdf

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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Ep11- Cash-Secured Puts: The Brother from Another Mother

In this episode, Dan dives into a powerful but often misunderstood options strategy: the cash-secured put. Often considered the sibling of the covered call, this strategy blends the best of investing discipline with the premium-collecting power of options trading.

What You’ll Learn:

• Why Dan used to hate cash-secured puts—and what changed his mind
  
  
• How selling puts can feel like setting a “limit order with benefits”
  
  
• The psychology behind financial freedom and higher-frequency trading
  
  
• The critical difference between trading and investing mindsets
  
  
• When assignment is part of the plan (and how to make that work for you)
  
  
• Key mechanics of the trade: risk, reward, and break-even calculations
  
  
• Real-life example: selling puts on WXYZ (Wanda’s Extra Yarn & Zippers Inc.)
  
  
• Why many traders stress less with cash-secured puts than with covered calls
  
  

Special Segment:

Dan brings on options coach John Kmiecik to talk about:

• How traders use cash-secured puts in one-on-one coaching sessions
  
  
• Why this strategy might be less stressful than covered calls
  
  
• How to manage trades if you don’t want to be assigned
  
  
• The role of sizing, account value, and portfolio allocation when using this strategy
  
  
• Common pitfalls like averaging down without a plan
  
  

Bonus for Subscribers:

Paid subscribers get access to:

• Video extras that break down P&L diagrams for cash-secured puts
  
  
• Real trade examples from Dan’s IRA
  
  
• Monthly Ask Me Anything sessions and more
  
  

Subscribe on Substack at:
wealthbuildingwithoptions.substack.com

Key Quote:

“Cash-secured puts aren’t just trades — they’re a mindset shift. They’re how investors say, ‘I’ll buy the stock… but only at my price.’”

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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Ep10 - Jumping into the Deep End of Covered Calls with Russell Rhoads

Episode Summary:
In this special episode, Dan Passarelli is joined by longtime friend and options expert Russell Rhoads—Associate Clinical Professor at Indiana University, former CBOE educator, and seasoned trader. They dive deep into real-world options education, covering everything from teaching college students about derivatives to building structured outcomes with options.

Topics Covered:

• Why concepts matter more than complex math when teaching options
  
  
• Covered calls and cash-secured puts as strategic investing tools
  
  
• How to use implied volatility (IV) and the at-the-money straddle for strike selection
  
  
• Surprising insights from Russell’s backtest on covered call strategies during earnings weeks
  
  
• The evolving perception of options in retail vs. institutional circles
  
  
• Understanding the VIX term structure and what today’s flat curve might be signaling
  
  
• How to “become the issuer” of your own structured product using options
  
  
• Why selling options—especially in calm markets—can give you the edge
  
  
• Tips for navigating earnings season with confidence
  
  

Key Takeaways:

• A consistent covered call strategy can outperform buy-and-hold—especially if you exit during earnings weeks
  
  
• The at-the-money straddle is a powerful, underused tool for estimating expected moves and timing trades
  
  
• Retail traders can learn to structure their own risk and reward profiles, just like institutional structured products
  
  
• The VIX futures term structure reveals market uncertainty—and today's unusual flat curve might be a red flag
  
  

Guest Bio:
Russell Rhoads is an experienced options educator, researcher, and practitioner. He teaches at Indiana University’s Kelley School of Business and consults with financial exchanges. Previously, he was the Director of Education at the CBOE’s Options Institute.

Resources Mentioned:

• Learn more about Dan: MarketTaker.com
  
  
• For options disclosures: Characteristics and Risks of Standardized Options (PDF)www.theocc.com/getmedia/a151a9ae-d784-4a15-bdeb-23a029f50b70/riskstoc.pdf
  

Subscribe & Review:
Don’t miss the next episode, “Cash-Secured Puts: The Brother from Another Mother” – Subscribe now and leave a review to help grow the Wealth Building With Options community!

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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Ep9 - Effing Around and Finding Out Why Covered Calls Work

Welcome back, Wealth Builders! In this episode, Dan Passarelli takes a deep dive into why covered calls continue to outperform the market over time—but only when done right. If you've ever wondered what gives covered calls their edge, this is your episode.

Key Topics Covered

• The Truth Behind Covered Calls: Why the strategy works statistically—but why most investors still fail with it.
  
  
• The Option Greeks Breakdown:
  
  
  • Delta (directional sensitivity)
    
    
  • Theta (time decay)
    
    
  • Vega (volatility sensitivity)
    
    
• The Hidden Edge: Risk Premium: How options have historically been overpriced since the 1987 crash, and how sellers can benefit.
  
  
• Volatility & Market Inefficiency: A critique of the Efficient Market Hypothesis and what it means for options traders.
  
  
• Why Repetition Matters: The compounding edge of consistently selling covered calls over time.
  
  
• Guest Interview: Henry Schwartz, VP of Market Intelligence at Cboe Global Markets, shares expert insights into the structural reasons options tend to be overpriced and how sellers can harness that edge.

“The price one can sell an option for is greater than the value it adds. That’s the whole magic of covered calls.” – Dan Passarelli

Free Gift: Covered Call Strategy Guide

Leave a review on Apple Podcasts, Spotify, or wherever you listen.
Then:

1. Take a screenshot of the review.
   
   
2. Post it to our Substack or on social media.
   
   
3. Use the hashtag #WBWO.
   
   

And we’ll send you Dan’s Covered Call Strategy Guide for free!

Mentioned in This Episode

• Dan’s book: Trading Option Greeks
  
  
• Black-Scholes Model origins
  
  
• Ken Griffin’s early arbitrage trades at Harvard
  
  
• University of Chicago’s Efficient Market Theory
  
  
• CBOE Global Markets and options data insights - https://go.cboe.com/l/77532/2025-02-13/flrl76/77532/1739470545lScFNDr9/State_of_Industry_January_2025_NEW.pdf

Tools for Traders

• Learn more about Dan at MarketTaker.com
  
  
• Subscribe to our Substack Newsletter https://wealthbuildingwithoptions.substack.com
  
  
• Follow Dan on social media
  • Instagram-https://www.instagram.com/markettakermentoring/
  • YouTube-https://youtube.com/markettakermentoring
  • Twitter-https://twitter.com/Dan_Passarelli
  • Facebook- https://www.facebook.com/markettaker

Don't miss Episode 10 with a very special surprise guest—someone with game-changing insight into options trading that you won’t want to miss.

Until then...
Invest excellently.

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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Ep8 - They Lied to You! (Not) Why Covered Calls Work

Episode Summary:

In this eye-opening episode, Dan Passarelli challenges the common misconceptions surrounding covered calls. While most traders focus on “why” covered calls work, Dan flips the script and digs into the false narratives and misguided logic that lead investors astray.

Dan explains why some of the most popular justifications for trading covered calls are intellectually lazy—and how overlooking key factors like option pricing models and probability curves can lead to missed opportunities or unnecessary losses.

This episode lays the foundation for next week’s deeper dive into the true reason covered calls work.

Key Takeaways:

• You’ve been misled: Many reasons given for why covered calls "work" are based on flawed logic, not solid data.

• Probability ≠ Profit: High-probability trades don’t always equal good trades—context and pricing matter.

• The 3 flawed logics covered call traders often fall into:

  1. The premium isn’t worth the risk.

  2. Assignment means “losing money.”

  3. Covered calls always add value, so trade them blindly.

• What really matters: Understanding the options pricing model, probability curves, and the indifference point.

• Analogy alert: Dan compares covered calls to buying a car—price must reflect value or the deal isn’t worth it.

• Guest Insight: Henry Schwartz of Cboe Global Markets joins to share data-backed insights into how buy-write strategies are used and who’s trading them.

Featured Concepts:

• Log-normal distribution curves and probability modeling

• Indifference point explained with a $119/$122 call example

• Options pricing mechanics: volatility, time, interest rates

• How pricing impacts strategy effectiveness

Special Offer:

Leave a review for the podcast on Apple Podcasts, Spotify, or your preferred platform.
Then screenshot your review and post it to our Substack or social media with the hashtag #WBWO.
We’ll send you Dan’s Covered Call Strategy Guide PDF—free.

Resources Mentioned:

• Wealth Building With Options on SubStack-https://wealthbuildingwithoptions.substack.com/
• MarketTaker.com – Learn more about Dan Passarelli and his work
• Options Disclosure Document (ODD) – Characteristics and Risks of Standardized Options (https://www.theocc.com/getmedia/a151a9ae-d784-4a15-bdeb-23a029f50b70/riskstoc.pdf)

• Connect with Henry Schwartz and Cboe Global Markets at cboe.com

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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Ep7 - The Future of Options Trading with Fidelity’s Greg Stevens

Episode Summary:

In this special Thought Leader Series episode of Wealth Building with Options, host Dan Passarelli sits down with longtime friend and industry veteran Greg Stevens, Vice President of Options Strategy at Fidelity Investments.

With nearly 30 years of experience across firms like Charles Schwab, the CBOE, and now Fidelity, Greg shares how the options trading landscape has evolved and why education remains the cornerstone of trading success. From the early days of dial-up trading to today's powerful digital platforms, Greg and Dan explore how strategy, risk management, and planning shape trader outcomes.

This episode is packed with real talk on covered calls, cash-secured puts, credit spreads, investor mistakes, how Fidelity supports options traders—and why having a trading plan matters more than ever.

Key Topics Covered:

• Greg’s journey into the options world (and how he was “dragged” in)
  
  
• Why options education is critical in today’s trading environment
  
  
• The evolution of self-directed trading and investor expectations
  
  
• Most popular options strategies among Fidelity clients
  
  
• The real reasons covered calls and cash-secured puts are so popular
  
  
• What separates successful traders from those who struggle
  
  
• Why planning for profits and losses is essential
  
  
• Fidelity’s tools, including commission-free closing of short options under $0.65
  
  
• Greg’s favorite books and movies on trading (hint: Trading Places is a classic)
  
  

Resources Mentioned:

• Characteristics and Risks of Standardized Options (Options Disclosure Document)-https://www.theocc.com/getmedia/a151a9ae-d784-4a15-bdeb-23a029f50b70/riskstoc.pdf
  
  
• Learn more about host Dan Passarelli: www.markettaker.com
  
  
• Books referenced:
  
  
  • Options as a Strategic Investment by Lawrence G. McMillan
    
    
  • Trading Options Greeks by Dan Passarelli
    
    
  • Trading Index Options by Dan Bittman
    
    

Final Takeaway:

“Even a bad plan is better than no plan at all. You can adjust a bad plan—but you can’t fix what doesn’t exist.”

Subscribe & Stay Informed:

If you enjoyed this episode, please subscribe, leave a review, and share it with fellow traders looking to level up their options game. Subscribe on your favorite podcasting platform or on https://wealthbuildingwithoptions.substack.com

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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Ep6 - How Covered Calls Work

Episode Summary: In this meaty episode of Wealth Building with Options, host Dan Passarelli breaks down one of the most powerful strategies for investors—covered calls. Whether you're a beginner looking to understand the basics or an experienced investor searching for new insights, this episode dives into the mechanics of covered calls, why they work, and how to use them effectively to enhance portfolio performance.

Dan explains the key principles behind covered calls, including risk management, profit potential, and why this strategy remains a staple for successful investors. He also discusses real-world applications, shares a practical covered call example, and introduces the importance of risk graphs (P&L diagrams) for visualizing potential outcomes. Plus, Dan highlights how covered calls can be modified and adapted to fit different investing styles, including conservative long-term wealth-building and active trading approaches.

Key Topics Discussed:

• What is a Covered Call? Breaking down its structure and purpose.
• The Two Components of a Covered Call: Stock ownership and short call options.
• Why Covered Calls Work: How they generate additional income while managing risk.
• Profit & Risk Scenarios: What happens if the stock price rises, falls, or stays flat.
• Real-World Example: Applying covered calls to a hypothetical stock trade.
• Advanced Considerations: Adjusting covered calls, selecting strike prices, and expiration dates.
• Common Mistakes & How to Avoid Them: Ensuring you maximize your covered call returns.

Dan also encourages listeners to help grow the Wealth Building with Options community by leaving a review and subscribing to the show. As a special incentive, listeners who post a review and submit proof on social media with the hashtag #WBWO will receive a free Covered Call Strategy Guide via the podcast’s Substack page.

Exclusive Subscriber Benefits: Paid subscribers receive bonus video content, detailed trade breakdowns, and access to a monthly Ask Me Anything (AMA) session. Join at wealthbuildingwithoptions.substack.com for in-depth resources and direct engagement with Dan and his team.

What’s Next? This episode is the first part of a two-episode series on covered calls. The next installment, Episode 7: Why Covered Calls Work, will explore the deeper reasoning behind this strategy, including statistical advantages, behavioral finance insights, and how institutions use covered calls to outperform the market.

Subscribe & Stay Updated! Never miss an episode—subscribe to Wealth Building with Options on your favorite podcast platform.

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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Ep5 - Options: Better Tools

Episode Summary: In this episode of Wealth Building with Options, host Dan Passarelli explores the foundational concepts of options trading. Using relatable analogies, Dan breaks down the mechanics of options, explaining calls, puts, and their practical applications. Additionally, he discusses how options function as financial tools for risk management, investment growth, and wealth protection.

Special guest John Kmiecik, Head Coach at Market Taker Mentoring, joins the conversation to share his insights from years of experience working with traders. Together, Dan and John dive into the psychology of trading, the advantages of selling premium, and why many traders transition from buying options to selling them. They also touch on the importance of developing consistent trading habits and how covered calls and cash-secured puts can serve as powerful strategies for investors.

Key Topics Discussed:

• Understanding Options Through Analogies: Comparing options to insurance, gas price guarantees, and even pizza coupons.

• Defining Calls and Puts: Explanation of how each type of option works and how they can be utilized by traders.

• Options as Financial Contracts: Exploring how options serve as tools for hedging risk, leveraging investments, and increasing portfolio efficiency.

• Common Misconceptions About Options Expiration: Understanding statistics around exercised, expired, and closed options.

• The Psychology of Options Trading: How trader mindset affects decision-making and success.

• Why Selling Options is a Popular Strategy: Examining the benefits of selling premium for generating income and managing risk.

• The Importance of Habit Formation in Trading: How discipline and repetition lead to better financial outcomes.

• Preview of Future Episodes: A look ahead to covered call strategies and their wealth-building potential.

Guest Spotlight: John Kmiecik John Kmiecik, the Head Coach at Market Taker Mentoring, has extensive experience educating traders. With a background that includes working with Goldman Sachs and a hedge fund, John has helped thousands of traders develop strategies for long-term success. In this episode, he shares insights on the advantages of selling premium and the importance of understanding both sides of the options market.

Actionable Takeaways:

• Start viewing options as financial contracts that can be leveraged for portfolio growth and risk management.

• Consider the advantages of selling options as part of your trading strategy.

• Focus on habit formation to build consistency in trading.

• Stay tuned for the next episode, which will cover covered call strategies in depth.

Resources Mentioned:

• See Dan and John's trade ideas on SubStack-https://wealthbuildingwithoptions.substack.com

• Market Taker Mentoring: MarketTaker.com

• Characteristics and Risks of Standardized Options: https://www.theocc.com/getmedia/a151a9ae-d784-4a15-bdeb-23a029f50b70/riskstoc.pdf

Subscribe & Stay Updated! Never miss an episode—subscribe to Wealth Building with Options on your favorite podcast app. Episode 6 will cover covered call trading and how it can help investors generate wealth faster.

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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