Wealth Building With Options

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Wealth Building With Options episodes

June 03, 2025Ep 17- Seasonality, Cycles & the Calendar Edge with Jeffrey Hirsch Editor-in-Chief of the Stock Trader's Almanac
Dan Passarelli is joined by Jeffrey Hirsch, editor-in-chief of the Stock Trader’s Almanac, to talk seasonality, market cycles, and the powerful edge of timing your trades around historical patterns. From family legacy to tactical trade execution, Jeff breaks down how decades of research—plus some good old-fashioned intuition—can give traders a powerful boost.
What You’ll Learn in This Episode:
Why "Buy in October and get your portfolio sober" might be better advice than “Sell in May and go away”
The most reliable fundamental metric for selecting value stocks
How Jeff’s family legacy shaped the Stock Trader’s Almanac—and how he came to embrace it
The surprising consistency of intraday trading patterns in a high-frequency world
Using seasonality with options: When to sell puts and calls for maximum edge
The power of the “best six months” and how to trade them with covered calls
Seasonal volatility trends—especially around August through October
Insights into election year cycles and how political shifts affect markets
A personal side of Jeff Hirsch: music, Broadway, and producing a musical inspired by The Elephant Man
Featured Guest:
Jeffrey Hirsch
Editor-in-Chief, Stock Trader’s Almanac
Market historian, strategist, and student of behavioral finance
Resources Mentioned:
Stock Trader’s Almanac
Learn more about Dan Passarelli and Market Taker Mentoring at 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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39 min
May 27, 2025Ep16 - OG CC Setups (part II)
Welcome back to Wealth Building with Options! In this episode, we’re diving deep into a trader's secret weapon: the Trade Objective of the covered call strategy — specifically, using covered calls to strategically exit a stock position.
If you’ve ever wondered:
How do I get the most out of a stock I already own?
What role does theta really play in my premium income?
How do I avoid leaving money on the table — or getting assigned too early?
…this episode is for you.
Dan Passarelli breaks down the nuances of “trading out of a stock you own” through smart strike selection, theta analysis, and volatility evaluation — and shares how to do it with confidence, precision, and better returns.
Here’s what you’ll learn:
Why traders should treat their trading like a real business — not a side hustle
The difference between the Skate Objective and the Trade Objective in covered calls
How theta, volatility, and time to expiration impact the effectiveness of your trade
The concept of aggregate theta and how to use it to compare expirations for maximum premium collection
Why tight bid/ask spreads and avoiding earnings dates are critical to your setup
The pros and cons of selling calls on stocks trading near all-time highs
How to incorporate both technical resistance and dividend timing into your decision-making

Special Guest: John Kmiecik
Dan is joined by trader and educator John Kmiecik, who shares his practical perspective on using theta and premium analysis to fine-tune covered call trades. They dig into real examples, including John’s experience with Comcast shares, and discuss how sometimes the best trade is the one you don’t make.
Listener Challenge:
Think about a stock you own that you’d consider selling at a higher price. Would a covered call help you exit at that level while collecting cash along the way? What would make it worth it — and what wouldn’t?
Resources & Mentions:
Dan's Substack – https://wealthbuildingwithoptions.substack.com for video extras, trade breakdowns, and AMA access
Episode 10 with Dr. Russell Rhoads
Episode 13 with Steven Sears
Subscribe now so you don’t miss Episode 17, featuring a very special guest and even more ways to take your option trading to the next level.
Ready to treat your trading like a business? This is where you start.
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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46 min
May 20, 2025Ep15 - OG CC Setups (part I)
In this deep-dive episode, Dan Passarelli lays out the OG Covered Call setup—the foundational approach to trading covered calls that every serious trader should understand. This episode is Part 1 of a two-part series that walks through the “Skate” Objective—a strategy focused on collecting premium while avoiding assignment.
Dan brings together technical chart analysis, volatility evaluation, and decades of options expertise to show you how to set up covered calls with confidence and precision.
Key Takeaways
Why sell options only when volatility is overpriced — and how to determine when that is
The importance of stock price and liquidity when choosing covered call candidates
Avoid earnings events and other scheduled volatility shocks that can ruin setups
The 10% Rule to minimize slippage and improve execution
Using technical resistance to “skate” profitably without getting assigned
Chart types explained (candles vs. bars vs. lines) and why candlesticks can give you an edge
How to evaluate volatility using the “1-2-3 Volatility Analysis”:
Tools & Concepts Covered
Covered Calls vs. Cash-Secured Puts
Option Chain Analysis
Implied Volatility (IV) vs. Historical Volatility (HV)
Resistance and Inflection Points
Strike Proximity and “Wiggle Room”
Using 6-month daily candle charts for timing and strike selection
Join the Community
Enjoying the podcast? Help grow the community:
Share the podcast with other traders
Subscribe in your favorite podcast app
Leave a review to support the show
Join the Wealth Building With Options Substack at 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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42 min
May 13, 2025Ep14 - Greek Geekery and Skewed Truth
Episode Summary:
In this episode, Dan dives into one of the most misunderstood aspects of options trading: the Greeks — and more importantly, where the real edge in trading actually comes from. Contrary to what many novice traders believe, theta is not the edge. The real advantage lies in volatility and skew.
With practical examples and 30 years of trading experience, Dan breaks down how delta works, why traders often misinterpret theta, and how cash-secured puts and covered calls use volatility pricing to your advantage.
In This Episode, You’ll Learn:
Why theta is not a reliable trading edge, despite popular belief
How delta works in directional trading and how to simplify its meaning
The true nature of short puts and why they behave like bullish stock positions
How risk premium gives option sellers an advantage
Why options behave like insurance policies — and how that helps traders
What volatility skew is and how to recognize it
How covered calls and cash-secured puts benefit from implied volatility mispricing
Key Concept:
Delta isn’t just a Greek — it’s the sensitivity of an option’s price relative to the underlying stock. When you understand how delta mirrors share ownership, your perspective on options changes completely. And when you understand skew, you start trading with a real edge.
Additional Resources:
To access bonus video content, trade adjustments, and subscriber-only episodes, visit:
wealthbuildingwithoptions.substack.com
Support the Show:
Share this podcast with fellow traders and subscribe to your favorite app so you don’t miss the next episode. A quick review or rating helps the show grow and reach more traders like you.
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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33 min
May 06, 2025Ep13 - The Golden Age of Options: A Conversation with Steven Sears
Episode 13 – The Golden Age of Options: A Conversation with Steven Sears
In this episode of Wealth Building With Options, Dan Passarelli sits down with one of the most influential voices in the options world—Steven Sears. A former senior editor at Barron’s, senior advisor to the Philadelphia Stock Exchange, and a key figure in the rise of electronic options trading, Sears brings decades of front-line experience and deep insight into how options can transform a portfolio.
In this wide-ranging and insightful conversation, you’ll discover:
Why we’re entering a “golden age” for options—and what it means for everyday investors
The power of compounding through covered calls and cash-secured puts
How top professionals select stocks to complement options strategies
Why managing volatility is more essential than ever in today’s market
The shift from speculative trading to disciplined, process-based investing
What most investors misunderstand about selling options—and how to fix it
The mindset that separates consistent winners from everyone else
Whether you're new to options or looking to sharpen your edge, this episode will challenge your assumptions, reframe your strategy, and inspire confidence in a smarter, steadier approach to building wealth.
Listen now and hear how Steven Sears sees the evolving landscape—and how you can thrive in it.
For more information about Dan Passarelli join him on Substack at 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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46 min
April 29, 2025Ep12 - 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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34 min
April 22, 2025Ep11- 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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Wah Wah Wah
Wah wah trumpet failed joke punch line.wav by Doctor_Jekyll -- https://freesound.org/s/240195/ -- License: Attribution 4.0
51 min
April 15, 2025Ep10 - 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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47 min
April 08, 2025Ep9 - 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:
Take a screenshot of the review.

Post it to our Substack or on social media.

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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Wah Wah Wah
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51 min
April 01, 2025Ep8 - 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:
The premium isn’t worth the risk.
Assignment means “losing money.”
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
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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45 min

About Wealth Building With Options

From the publisher's feed

Welcome to the Wealth Building With Options Podcast with Dan Passarelli. This podcast is dedicated to making you a calm, consistent and confident options trader. Inside each episode, Passarelli, an…