In this episode of Wealth Building with Options, Dan Passarelli dives deep into the motivations behind trading the wheel strategy—and why understanding them can make or break your results.

Dan begins with a mistake he sees all too often: traders push strikes too far away from the stock price, "running and hiding" instead of sticking to their true objective—getting assigned—which undermines their entire strategy. From there, he lays out the framework of the who, what, and why of the wheel strategy:

Who trades the wheel?

What is cycling into wheel trades?

Why trade the wheel? Dan highlights both trade objectives (intentionally getting assigned into or out of stock) and skate objectives (capturing premium without assignment). For cash-secured puts with trade objectives, he identifies three main sub-motivations:

The Cycle Mindset Revolution

A key takeaway: successful wheel trading isn't about the profitability of individual trades, but about completing profitable cycles. Dan explains how traders can recover from losses by continuing the sequence until the overall cycle closes in profit: "I sold this put at $1 and now I have to buy it back at $2.50. I'm down $1.50 but I sell another put at $1.25... It took me 3 trades to lock in 50 cents. That is a completed cycle." This mindset shift—focusing on cycles rather than one-off wins—separates successful wheel traders from those who give up too early.

Professional Insights

Dan also reveals how professional traders approach the wheel differently. Instead of hiding far out-of-the-money, institutional traders often sell "500, 1000, 2000 puts right at the money," showing why proper strike selection is critical when the goal is assignment.

Whether you're new to the wheel or already using it, this episode will fundamentally change how you think about each trade within the larger cycle—and why patience with the process, not individual results, drives long-term profitability. By the end, you'll understand why focusing on cycles, not individual trades, is the key to wheel success.

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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Most wheel traders obsess over single trades and miss the bigger picture. In this episode, Dan Passarelli shares the mindset shift that changed his covered call and cash-secured put trading: manage in cycles, not one-offs.

Using a powerful casino/blackjack analogy, Dan reveals why even professional card counters can lose money for six months straight despite having an edge—and how "how you play" determines your actual results, not just the statistical probabilities. He then introduces the Net Zero Roll, a practical technique to transfer short-term options losses from money to time by rolling up and out, keeping the wheel moving toward profit.

Through a detailed walkthrough of a real trading scenario (a May 15th, 170 call that goes against you), you'll discover how three separate trades in one cycle can deliver the same 85-cent profit you wanted from one trade—it just takes a bit longer. Dan emphasizes this was his personal epiphany that transformed his trading and inspired his upcoming book.

Key Takeaways

What You'll Discover

Action Steps

Coming Up

Dan mentions the second key area for wheel success—rewiring your brain—will be covered in upcoming episodes. This psychological framework will span several shows as it's central to his new book.

Resources

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

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

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

What You’ll Discover in This Episode:

Key Takeaways:

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 sits down with longtime market maker Kevin “Lex” Luthringshausen to demystify how options markets actually work behind the scenes. They cover dealer/market-maker behavior, why hedging is the real “edge,” how dispersion trading works, and what payment for order flow (PFOF) really is—and why it matters for retail traders. The conversation finishes with practical guidance for covered calls, cash-secured puts, and the “poor man’s covered call” (fig leaf), plus Lex’s favorite trading books and films.

Key Topics

Lex’s Practical Takeaways

Resources Mentioned

Connect

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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Options trading is all about choice—and in this episode, Dan Passarelli breaks down why those choices create real value for investors. From adjusting strikes to rolling trades, Dan dives deep into how flexibility and decision-making in the Wheel Strategy can drive long-term profitability.

He also shares personal reflections about family milestones, the importance of practical education, and how trading truth (not oversimplified textbook theory) is what truly pays.

What You’ll Discover in This Episode:

Key Takeaways:

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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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.

Support the Show

Help grow the Wealth Building with Options community!

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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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.

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."

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."

Help grow the wealth-building community by:

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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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.

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

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

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

Join here: wealthbuildingpodcast.com

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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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.

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.

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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"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.

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.

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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