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Dan puts implied volatility in its proper place: It’s not the single most important factor in wheel trading, but it meaningfully improves outcomes over time. Using a field-goal analogy, Dan explains how volatility analysis adds a “little edge” on each trade that compounds across many cycles. He then goes deeper into when volatility matters most, plus a practical framework for evaluating whether selling puts or calls into earnings creates a favorable “sweet spot.”
IV is an edge, not the core driver. Underlying price movement and theta are usually more influential in wheel outcomes, but IV adds incremental advantage that compounds over time.
Active and passive wheel traders use IV differently. Active traders may require confirmation that options are overpriced; passive traders may prioritize keeping the cycle going and capturing the long-run risk premium.
Humility matters in volatility forecasting. You can’t know with certainty whether options are mispriced until after expiration, so rules-based processes help reduce overconfidence.
Regime awareness beats day-to-day noise. A few low-IV days are normal; weeks or months of a pattern can justify sitting out or adjusting tactics, especially in strong rebound “freight train” markets.
Extremes cut both ways. Slightly high IV can be attractive for selling, but extremely high IV may signal risk you don’t understand.
Earnings setups can be evaluated objectively. Compare historical earnings gaps with the option’s break-even/indifference “sweet spot” to judge whether premium meaningfully compensates for the expected move.
If selling calls to exit stock into earnings, assignment probability matters. At-the-money or slightly in-the-money calls can improve assignment odds and provide more downside cushion, but the true advantage comes from time premium, not intrinsic value.
Learn more about host Dan Passarelli and Market Taker Mentoring: MarketTaker.com
Get exclusive content including video trade walk-throughs, Dan's actual trades, monthly AMA webinars and more: wealthbuildingpodcast.com
Subscribe on your preferred platform and leave a review to help more traders discover the show.
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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Dan explains why wheel traders must think about technical analysis differently from momentum or breakout traders. Using a Home Depot analogy, Dan shows how the right tool for the job matters—especially when selecting indicators for skate-objective trades. He dives into oscillators (with a focus on RSI) and introduces a new strike-selection concept he’s developing.
Wheel traders don’t want momentum. Strong trends often force rolls, increase trade count and slow down wheel cycles.
Technical analysis should reduce activity, not increase it. The goal is fewer trades per cycle, not more signals.
Oscillators are better tools for wheel traders. Indicators like RSI help identify waning momentum rather than breakouts.
RSI can improve strike selection. Overbought and oversold reversals—and divergences—can increase the odds of skating successfully.
Indicators don’t predict the future. They provide a small statistical edge when used correctly.
Volatility matters as much as price. Understanding whether options are overpriced or underpriced is critical for consistent income strategies.
Learn more about host Dan Passarelli and Market Taker Mentoring: MarketTaker.com
Get exclusive content including video trade walk-throughs, Dan's actual trades, monthly AMA webinars and more: wealthbuildingpodcast.com
Subscribe on your preferred platform and leave a review to help more traders discover the show.
Next Episode Preview: Next time, Dan goes deeper into volatility analysis, expanding on how wheel traders can evaluate implied volatility, historical volatility, and upcoming catalysts to improve covered call and cash-secured put decisions.
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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Dan demystifies one of the most misunderstood areas of technical analysis: support and resistance. Rather than treating these levels as “magic lines on a chart,” Dan explains the market mechanics behind them—how real buy and sell orders, supply and demand, and human decision-making actually move prices.
Key Topics
Why support and resistance are commonly misunderstood
Technical analysis as a map of human behavior (price, not value)
The basics of market mechanics: bids, asks and order size
How supply and demand move prices tick-by-tick
How horizontal support and resistance levels are created
Why price levels hold—and the three main reasons they break
Moving averages (SMA/EMA) as dynamic support and resistance
Why the 200-day moving average matters to institutions
“Death cross” and “golden cross” and what they signal
Applying support/resistance to wheel strike selection for skate trades
Key Takeaways
Support and resistance aren’t magic. They reflect real buying and selling pressure created by market participants.
Technical analysis explains price behavior, not valuation. It tracks what price and volume did—and how traders reacted.
Prices move through order flow. Buyers absorb offers to push price up; sellers take out bids to push price down.
Support/resistance can fail for predictable reasons. Levels break when supply/demand overwhelms the other side, participants finish their trades or new information changes valuation inputs.
Moving averages can become self-reinforcing levels. Long-term averages like the 200-day influence institutional decisions and can behave like support or resistance.
Wheel traders can use these levels to improve skate trades. Support can inform cash-secured put strikes; resistance can inform covered call strikes.
Connect
Learn more about host Dan Passarelli and Market Taker Mentoring: MarketTaker.com
Get exclusive content including video trade walk-throughs, Dan's actual trades, monthly AMA webinars and more: wealthbuildingpodcast.com
Subscribe on your preferred platform and leave a review to help more traders discover the show.
Next Episode Preview: Next time, Dan continues building on technical analysis for wheel traders—going deeper into how to apply support, resistance and key chart-based levels to choose strikes that improve the probability of skating without assignment.
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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Dan breaks down the true “secret sauce” of successful wheel trading: pairing the right objective (trade vs. skate) with the right type of analysis (fundamental vs. technical). He demonstrates how to reverse-engineer strike prices using dividend yields and valuation metrics and walks through a real example using Verizon (VZ).
Every wheel trade needs a single, clear objective. Choose either skate (avoid assignment) or trade (seek assignment) to stay consistent and intentional.
Match your analysis to your objective. Use fundamentals for trade-objective entries and technicals for skate-objective premium selling.
Reverse-engineer your strike prices. Start with the yield or valuation you want, determine the stock price that achieves it, and choose the strike accordingly.
Premium can tweak your effective entry price—but don’t lose the plot. Premium helps refine entry, but fundamentals should guide the trade.
Wheel trading can be “almost win–win,” but risk still exists. Assignment locks in value; non-assignment yields premium—but price risk remains.
Conservative income plays can complement growth positions. High-yield value names can balance more aggressive holdings.
Learn more about host Dan Passarelli and Market Taker Mentoring: MarketTaker.com
Get exclusive content including video trade walk-throughs, Dan's actual trades, monthly AMA webinars and more: wealthbuildingpodcast.com
Subscribe on your preferred platform and leave a review to help more traders discover the show.
Next Episode Preview: Next time, Dan digs deeper into technical analysis for skate-objective trades, focusing on how horizontal support and resistance can help identify strike prices where the stock is less likely to move—boosting your confidence and consistency when selling premium.
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 trumpet failed joke punch line.wav by Doctor_Jekyll -- https://freesound.org/s/240195/ -- License: Attribution 4.0
Dramatic Drum Roll
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Dan compares buying stocks to buying a dry cleaning business to demystify fundamental investing. Learn how value investors like Warren Buffett evaluate companies, and why understanding P/E ratios, earnings, and dividends can help you select better strike prices for your wheel trades.
You actually own the business. When you buy stock, you own a proportional share of that company's revenue—it's literally your money.
Dividend investors think backwards. While most people chase rising stocks, dividend investors wait patiently for prices to fall so they can lock in higher yields.
Price isn't value. The stock market often disconnects from intrinsic value—that's where opportunities hide.
Your fundamentals matter for strike selection. Understanding earnings and dividend yield can help you choose more strategic strike prices for covered calls and cash-secured puts.
Learn more about host Dan Passarelli and Market Taker Mentoring: MarketTaker.com
Get exclusive content including video trade walk-throughs, Dan's actual trades, monthly AMA webinars, and more: wealthbuildingpodcast.com
Subscribe on your preferred platform and leave a review to help more traders discover the show.
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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Episode Summary
Denise Shull is a former CBOE floor trader turned performance coach specializing in decision-making under risk and uncertainty. She holds a master’s degree in neuropsychoanalysis from the University of Chicago, traded at firms like Schonfeld, and later ran a day trading desk during the internet boom. Her work shows how emotion and cognition are intertwined in every decision—a theme she explores in her book Market Mind Games, which helped inspire the Wendy Rhoades character on Showtime’s Billions. Today, she coaches hedge fund managers, traders, and elite athletes around the world on how to use emotions and intuition as a competitive edge.
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 trumpet failed joke punch line.wav by Doctor_Jekyll -- https://freesound.org/s/240195/ -- License: Attribution 4.0
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Finding quality trade ideas for the Wheel Strategy is essential—but where do you actually get them? In this episode, Dan Passarelli breaks down the best (and worst) sources for finding wheel trade candidates. From trade idea services and investment clubs to news media and DIY analysis, Dan explores the pros and cons of each approach and shares what really works for covered calls and cash-secured puts.
Dan also discusses why boring, sideways stocks make the best wheel candidates, why the pundits' favorite stocks are often the trickiest to trade, and teases an upcoming series on fundamental, technical, and volatility analysis for building your own watchlist.
What You'll Discover in This Episode:
Resources & Links:
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
Dramatic Drum Roll
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In this episode of Wealth Building with Options, Dan sits down with James Kostulias, Head of Trading Services at Schwab—where he oversees the end-to-end trading experience for clients at a firm averaging over 7 million trades per day for three consecutive quarters.
From Schwab’s latest Q4 Trader Sentiment Survey to the dramatic evolution from “options are too risky” to “options as risk management tools,” James shares an insider’s view of how retail trading has fundamentally transformed.
If you've ever wondered how serious traders think about hedging, income generation, and adapting to different market regimes, this conversation is packed with insights you can put to work in your own trading.
Guest Bio – James Kostulias
James Kostulias is Head of Trading Services at Schwab, where he oversees the end-to-end trading experience for clients, including the award-winning thinkorswim suite of platforms. With more than 25 years in financial services—much of it with TD Ameritrade in retail, technology, and active trader leadership roles—James has been at the forefront of the industry’s evolution from “options are too risky” to “options as risk management.”
He has served as a board member and former president of the Wall Street Technology Association, previously sat on FINRA’s Technology Advisory Committee, and is a graduate of the SIFMA Securities Institute program at Wharton. He holds a B.A. in Business Administration from Rutgers University along with Series 47, 24, and 63 licenses.
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.
Trumpet
Wah Wah Wah
Wah wah trumpet failed joke punch line.wav by Doctor_Jekyll -- https://freesound.org/s/240195/ -- License: Attribution 4.0
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dramatic drum roll.wav by ingsey101 -- https://freesound.org/s/51401/
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Why Traders Lie to Themselves — and How to Stop
When it comes to covered calls and cash-secured puts, most traders tell themselves comforting half-truths:
In this episode, Dan Passarelli unpacks the psychology behind these lies and how to replace emotional trading with data-driven discipline. Through relatable stories (including a red-light ticket and an ancient Roman twist), Dan shows why even the smartest investors fall into the trap of self-deception—and how to break free from it.
You can’t control the market—but you can control how you react.
Subscribe & Support: WealthBuildingPodcast.com — Get access to video extras, subscriber-only trade ideas, Dan’s real covered call and cash-secured put trades, monthly AMAs, and unusual options activity alerts.
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
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dramatic drum roll.wav by ingsey101 -- https://freesound.org/s/51401/ -- License: Attribution 3.0
Episode 38: The Objective of My Affliction
95% of traders lose money. Not because they're not smart—but because they're missing something fundamental.
In this episode:
This episode is short but mighty. Discover what separates the winning 5% from everyone else.
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.
Trumpet
Wah Wah Wah
Wah wah trumpet failed joke punch line.wav by Doctor_Jekyll -- https://freesound.org/s/240195/ -- License: Attribution 4.0
Dramatic Drum Roll
dramatic drum roll.wav by ingsey101 -- https://freesound.org/s/51401/
-- License: Attribution 3.0
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