Wealth Building With Options

Ep28 - I Never Said Most of the Things I Said

In this episode of Wealth Building with Options, host Dan Passarelli dives deep into one of the most popular and misunderstood strategies in options trading: the Wheel Strategy. Drawing inspiration from a (possibly misattributed) Yogi Berra quote — “In theory, there’s no difference between theory and practice, but in practice there is” — Dan explores how the wheel works in real life, why some traders fail with it, and how to use it as a disciplined, systematic approach to grow wealth.

Joining Dan is frequent guest and fellow coach John Kmiecik, who shares his insights on both the mechanics and the psychology behind the wheel. Together, they unpack the nuances that make this strategy both powerful and deceptively simple.

What Dan Reveals in This Episode

• The Wheel Explained: How cash-secured puts and covered calls form a repeating system to generate consistent premiums.
• Theory vs. Practice: Why data shows the wheel can beat the market, but traders still fail without methodology and discipline.
• Pin Risk & Assignment Nuances: Unlikely but important scenarios every wheel trader should understand.
• Premium vs. Stock Scalping: Which matters more when trading the wheel, and how premiums can smooth out “wrong” outcomes.
• Trader Psychology: Why relaxation, patience, and mindset shift from “trader” to “investor” are essential for success.
• Practical Tips: From good-till-cancel buyback orders to managing emotions and avoiding overtrading.

Key Quotes

• “The wheel is an if-then series of steps traded cyclically, growing wealth faster than buy-and-hold.” – Dan Passarelli
• “Relax. You’re absolutely going to love this strategy. I can stake my life on it.” – John Kmiecik

Support the Show

Help grow the Wealth Building with Options community!

• Subscribe in your favorite podcast app.
• Leave a review to help other traders find the show.
• Consider a paid subscription for exclusive video extras, monthly AMAs, unusual options activity alerts, and Dan’s real covered call and cash-secured put trades.

Until next time—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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Ep27 - Frickin’ Hulu

In this episode of Wealth Building with Options, Dan Passarelli opens with a hilarious rant about Hulu's "double dipping" business model—charging subscribers AND showing ads—which becomes the perfect metaphor for today's topic: covered strangles and covered straddles. These underused strategies allow options traders to "double dip" by collecting premium from both calls and puts, creating excellent opportunities for wealth builders willing to embrace a more sophisticated approach.

Key Takeaways:

The Double-Dip Concept

• Just like Hulu gets paid by subscribers AND advertisers, covered strangles let you collect premium from both selling calls and selling puts
• You're getting two income streams from a single underlying position, though only one option can be assigned
• Dan shares a real trade he placed

What is a Covered Strangle?

• A 3-part position: Own 100 shares + sell an out-of-the-money call + sell an out-of-the-money cash-secured put
• Perfect for long-term value investors: "Buy more if the stock goes lower, sell if it goes higher"
• Warning: You risk doubling your position (200 shares) if assigned on the put

Real-World Example: American Eagle Outfitters (AEO)

• Stock at $10.96, sold $11 calls for $1.80, sold $9 puts for $1.00
• Total premium collected: $2.80 (over 25% of stock price!)
• Massive profit zone: Stock can trade anywhere from $8.58 to $13.80 and you still win
• That's nearly a 50% range where the strategy is profitable

Why These Strategies Work

• Theta is King: Time decay works in your favor on both options
• Range-Bound Stocks: Perfect for "boring, sideways" stocks that stay in wide ranges
• Long-Term Approach: Often uses LEAPS (6+ months) for maximum time premium collection

Covered Strangle vs. Covered Straddle

• Strangle: Different strikes (out-of-the-money call and put) - more conservative
• Straddle: Same strike price - more aggressive, always has one option in-the-money
• Find out what Dan prefers for flexibility and risk management

The "Set It and Forget It" Management Style

• The Thanksgiving Turkey Approach: Check monthly, not daily - let theta do the work
• Immediate GTC Orders: As soon as filled, Dan places good-til-cancelled orders to buy back 
• Only Trade on Fundamentals: Don't make changes based on mood - only for significant company news

Advanced Techniques

• Split-Time Strangles: Different expiration dates for calls and puts when legging into positions
• Ratio Variations: Dan's current trade uses 20 puts vs. 1 call for enhanced income generation
• Liquidity Requirements: Tight bid/ask spreads essential - this strategy doesn't work with wide markets

Critical Success Factors:

When to Use This Strategy

• You genuinely want to own more shares if the stock drops
• You're comfortable selling your shares if the stock rises significantly
• The stock has strong support levels and reasonable valuation
• Options have tight bid/ask spreads and good liquidity

Risk Management

• Understand you're adding risk, not truly "covering" it (Dan calls the name misleading)
• Be prepared for potential assignment on either side
• Only use on stocks you'd be happy to double down on
• Avoid if you think the stock might "explode" higher

Why Dan Loves This Strategy

• "Perfect for value investors" - aligns buying and selling with valuation
• Excellent for takeover candidates with strong support levels
• Can generate 25%+ returns in sideways markets
• Works especially well on lower-priced stocks due to volatility skew

The Bottom Line

Covered strangles and straddles aren't everyday strategies, but when market conditions align, they can be "freaking amazing." The key is patience, proper stock selection, and treating them like long-term investments rather than short-term trades.

Dan's Reality Check: "This is a very, very niche strategy... but for the right set of circumstances, gosh man, this can be really, really amazing."

Exclusive Content for Subscribers

Paid subscribers get video walk-throughs of P&L diagrams for these complex strategies - essential for visualizing how these trades work. As Dan notes, "It's an audio-only podcast, so that's really the only way I can show you how to do this."

Join the Community

Help grow the wealth-building community by:

• Subscribing on your favorite podcast platform
• Leaving a review to help others discover the show
• Supporting with a paid subscription at WealthBuildingPodcast.com for exclusive video content, trade alerts, and monthly live Q&A sessions

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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Ep 26 - Interview with Options Thought Leader, Andrew Lowenthal

A candid conversation with one of the options industry’s most influential figures, tracing the explosive growth of the options market, the evolution of strategies like covered calls and cash-secured puts, and what’s ahead for global adoption.

Key Takeaways

• From 1983 to 2025: Andy shares how a fractions test in the Chicago Board of Trade building launched his 40-year career with CBOE Global Markets.
• Explosive Growth: The options industry has grown from 10M to 55M contracts traded daily in under a decade—an incredible expansion in both volume and notional value.
• Flex Options Uncovered: Andy gives a deep dive into Flex Options, their origin, how they provide customizable hedging, and why they’re now essential for ETFs and institutional strategies.
• The Power of Education: Andy reflects on how CBOE’s early commitment to education—like the Options Institute—laid the foundation for modern retail adoption.
• Global Footprint: Andy helped launch and develop options markets around the world—from Kuala Lumpur and Prague to London and Singapore.
• Retail’s Rising Role: Once just 1-2% of all accounts, retail options trading has surged thanks to technology, accessibility, and self-directed broker platforms.
• Covered Calls & Cash-Secured Puts: Asset managers and advisors increasingly use these foundational strategies, not just for yield, but for smarter portfolio construction.
• Benchmarks & Innovation: Dan and Andy discuss CBOE's development of benchmark indexes like BXM and PUT, which paved the way for modern ETF strategies and institutional replication.
• New Frontiers: Andy shares his work with Adaptive Financial—a fintech platform that uses software to analyze portfolios and generate index option-based trades.
• Trading for Fun: In retirement, Andy has turned to more personal trading, refining his exit strategy and embracing the learning curve of options firsthand.

Quotes to Remember

“Options are the one tool that lets you express your market view—up, down, sideways, or on timing—however you see fit.”
— Andy Lowenthal

“The exit determines if you make money. Getting into the trade is the easy part.”
— Dan Passarelli

Topics Covered

• Early trading floor culture and open outcry
• The rise of hybrid and electronic systems
• International exchange development (Prague, Malaysia, Brazil, more)
• The explosion in options education and retail access
• Flex options and ETF adoption
• Covered calls, cash-secured puts, and benchmark indexes
• Software-driven portfolio optimization with index options
• Exits, edge, and trading as a lifelong skill
  

Featured Mentions

• CBOE Global Markets
• Adaptive Financial Solutions
• Wilson Innovators
• Options Institute
• Risk Management Conference (CBOE)
• Benchmark Indexes: BXM, PUT
• Flex Options and Buffer ETFs
  

Subscribe & Support

Enjoying the podcast? Help support the show and access exclusive content:

• Video walk-throughs of real trades
• Subscriber-only stock breakdowns
• Covered call & cash-secured put trades from Dan’s own account
• Live monthly Ask-Me-Anything webinars

Join here: wealthbuildingpodcast.com

Thanks to Our Paid Subscribers

A special shoutout to:

Sean K, Steve D, Nanan, Glen K, Jane (our newest!), Alex H, Bill H, VJ, Paul P, Myron, Mark, Spencer, John D, Douglas B, Ed B, Christopher L, Deborah, and Eric G.

 

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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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
  
  

Support the Show

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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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Ep24 - Commitment Issues

"There's the kind of stock you date, and the kind of stock you marry."

In this episode of Wealth Building With Options, Dan explores what it means to have "commitment issues"—not in relationships, but in trading. Sometimes you don't want to marry a stock for life. You just want to take it for a profitable spin while managing your risk. That's where short-term buy-writes shine.

What You'll Learn:

• The psychology behind "dating" vs. "marrying" stocks—and why everything is impermanent
• When short-term buy-writes outperform buy-and-hold strategies
• How to evaluate opportunities when you like the fundamentals but don't fully trust the stock
• The "money lying in the corner" approach—waiting for exceptional premium opportunities
• Why 3 weeks to 2 months is the sweet spot for short-term buy-writes
• Three exit strategies at expiration: roll, close, or accept assignment
• The three-way analysis method: always consider multiple approaches to any opportunity

Real Trade Breakdown:

The Perfect Setup: Dan walks through a $30 stock example where you can capture a 5% out-of-the-money call for 3% premium—creating potential 8% monthly returns (96% annualized when opportunities align).

Okta (OTA) Case Study: How Dan rolled from a covered call assignment at $98 into cash-secured puts at $96, then down to $95 strikes, capturing $2.15 in additional premium while positioning for better entry points.

Rigetti (RGTI) Quantum Play: A speculative quantum computing stock offering 10%+ monthly premiums—demonstrating how to play the "sweet spot" of risky stocks using short-term strategies.

Key Insights:

• Log-normal distribution reality: Most individual stocks actually lose money over time (despite the S&P 500's 10% annual average) because index committees actively select winners
• Annualized returns truth: While 8% monthly sounds like 96% annually, you can't always replicate perfect setups—but the math still provides valuable baseline comparisons against risk-free rates
• Gap risk management: Why Dan prefers closing entire positions on expiration day rather than letting calls expire
• Value vs. speculation balance: How to capture meaningful premiums on stocks with mixed fundamentals

The Bottom Line:

Short-term buy-writes let you profit from stocks you like but don't fully trust, capturing meaningful premiums while maintaining clear exit strategies. Perfect for traders who prefer calculated risks over permanent commitments—and smart enough to know that in trading, as in life, everything is temporary.

Support the Show: Love the podcast? Share it with a friend, leave a review, and consider a paid subscription on Substack (https://wealthbuildingwithoptions.substack.com) to access bonus episodes, detailed trade breakdowns, and monthly AMAs.

Subscribe now so you don't miss Episode 25—another masterclass in confident, systematic trading is coming your way.

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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Ep23 - The Day I Bit The Nurse

In this episode, Dan shares a hilarious childhood story (yes, he did bite a nurse) and takes a nostalgic look at Highlights magazine to set up a powerful trading lesson about spotting subtle—but meaningful—differences between two nearly identical options strategies: the buy-write and the cash-secured put.

Both strategies aim to acquire stock and generate income, and from a risk-reward standpoint, they appear almost interchangeable. But when you look closely—like Gallant and Goofus in Highlights—you’ll find key differences that can impact commissions, dividends, interest, mindset, and how you manage risk.

What You’ll Learn in This Episode

• A humorous childhood story that leads to a serious insight about how traders interpret similar setups differently
• The key mechanical difference between a covered call and a buy-write
• How a buy-write compares to a cash-secured put in terms of:
  • Maximum profit
  • Break-even price
  • Commissions
  • Option Greeks (Delta, Vega, Theta)
  • Dividends and interest impact
  • Mental framing and trade psychology
• Why buy-writes often look better on paper—but might not always be the better choice
• How your broker's assignment and commission policies could tilt the scales
• Why dividend-paying stocks may favor buy-writes over cash-secured puts
• The one question to ask yourself that might matter more than the math: How do I think about this trade?

Key Takeaways

• A buy-write = Buy stock + Sell call (same time, same trade ticket)
• A cash-secured put = Sell put with cash reserved to buy shares if assigned
• Both trades are synthetically similar—but taxes, dividends, mindset, and fees can make a meaningful difference
• The mental framing of a trade might be the most important variable of all
• Sometimes, “spotting the difference” is the key to making the right strategic decision

Subscribe & Support

• Enjoy the show? Share it with a fellow investor
• Subscribe to get future episodes on short-term vs. long-term buy-writes
• Want deeper dives and trade breakdowns? Support the show with a paid Substack subscription and you'll also get access to the video extras: 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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Ep22 - "Hey Butthole"

Dan Passarelli kicks off this episode with a wild story from the trading floor—complete with Hulk-like rage and a colorful nickname—and uses it to dive deep into one of the most powerful and misunderstood ideas in options trading: synthetic positions.

This episode explores how synthetics reveal the truth about covered calls and cash-secured puts—that they are, in fact, two sides of the same coin. Dan unpacks the logic behind synthetics, the Greeks that drive them, and why understanding this can make you a sharper, more strategic investor.

In This Episode:

• The infamous “Hey Butthole” trading floor story—and what it teaches about real-world trading
• Why a trader’s “172” call position wasn’t an error—it was a lesson in synthetics
• The delta-neutral mindset of market makers and how it unlocks synthetic thinking
• Covered calls vs. cash-secured puts: Why they’re synthetically identical (and when they’re not)
• Understanding put-call parity and its real-world implications
• The Greeks of synthetics: Delta, Theta, and the messy role of interest and early exercise
• How professional traders use synthetic stock, conversions, reversals, and synthetic straddles
• When a put and a call add up to more than 100 delta—and what that means
• How synthetics help you manage vertical spreads, identify arbitrage, and reduce capital requirements
• Why thinking in terms of synthetics leads to smarter, more flexible trading decisions
  

Why It Matters:

Understanding synthetics isn’t just academic—it’s foundational. If you truly grasp this concept, you’ll:

• Trade covered calls and cash-secured puts with more confidence
• Identify hidden equivalencies across strategies
• Improve capital efficiency and decision-making
• Spot arbitrage and mispricing opportunities others miss

Quote of the Episode:

“If I own 100 shares and I’m short one call, that’s a covered call. If I’m short a put at the same strike—guess what? At expiration, they behave exactly the same.”

Don’t Miss:

Next episode, Dan dives into buy-writes and how to use them effectively in today’s market conditions. Make sure you subscribe so you’re the first to know when it drops.

Resources & Links:

• Trading Option Greeks – by Dan Passarelli
• Join the community at WealthBuildingWithOptions.Substack.com for bonus episodes, trade breakdowns, and monthly AMAs

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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Ep21-The Edge of Reason: And the Reason for Edge

In this episode of Wealth Building with Options, host Dan Passarelli explores one of the most powerful, yet often overlooked, concepts in successful trading: edge. Whether you're seeking an advantage like a card counter at the blackjack table or building consistency through disciplined investing, edge—the measurable statistical advantage—is what separates consistent winners from the rest.

What You'll Learn in This Episode:

• What edge really means in trading and how even a small edge can compound into powerful long-term results
  
• The three primary sources of edge every options investor needs to understand:
  
  • Fundamental analysis (PE ratio, price-to-book, operating yield, current ratio)
    
  • Technical analysis (support, resistance, moving averages, volume)
    
  • Volatility analysis (historical vs. implied volatility, vertical skew, term structure)
    
• How smart investors use support and resistance levels to improve strike selection and time their trades more effectively
  
• Why volatility pricing can create opportunity if you know how to spot overpriced or underpriced options
  
• A practical framework for setting strike prices and choosing expirations for covered calls and cash-secured puts
  

Dan also shares stories from the trading floor and insights from professional mentors, blending theory with real-world examples in a way that brings clarity to complex topics.

Resources Mentioned:

• The Intelligent Investor by Benjamin Graham
  
• Buffettology by Mary Buffett
  
• How to Read a Financial Report by John and Tage Tracy
  

Final Thoughts:

Even a 1–2% edge can significantly improve your trading outcomes—especially when compounded over time. Dan explains how mastering these analytical tools can help you trade more confidently and profitably, while avoiding common mistakes.

Subscribe to the show to catch Episode 22, where Dan dives deep into buy-writes and how to maximize capital efficiency using this foundational strategy.

To support the show and get access to exclusive episodes, trade breakdowns, and AMAs, visit:
wealthbuildingwithoptions.substack.com

To learn more about Dan Passarelli and the Market Taker Mentoring community, visit MarketTaker.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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