Wealth Building With Options

Dan takes a critical but balanced look at backtesting and why it often leads traders astray, especially when it comes to strike and expiration selection for covered calls and cash-secured puts. Drawing on decades of experience and firsthand work with traders and developers, Dan explains why backtesting tools have structural limitations, how those limitations create misleading conclusions, and why...

Dan ties the wheel strategy to New Year’s resolutions, emphasizing that the wheel only works when it’s traded consistently and in cycles. He explains how to systematize the process so it fits into real life—reducing friction, minimizing time demands and making long-term wealth building sustainable. Key Topics Why the wheel succeeds only as a cyclical strategy Commitment to process over individual...

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 se...

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. Key Topics Why trends and momentu...

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 o...

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). Key Topics Defining the skate objective vs. the trade objective Why trade...

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. Key Topics The dry cleaner analogy: why buying stock is just like buying a business P/E ratios: what they reveal wh...

Episode Summary In this conversation, Dan sits down with performance coach and former trader Denise Shull, author of Market Mind Games and the real-life inspiration for Wendy Rhoades on Billions. Denise explains why the old mantra “take the emotion out of trading” is scientifically wrong—and how learning to work with your emotions, instead of against them, can dramatically improve your decision-ma...

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 p...

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...

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: “I’d be fine owning the stock if it drops.” “I’d be fine selling my shares if they get called away.” But when those scenarios actually happen—when a stock gaps lower or rallies far past a strike—those same traders often panic, blame the market,...

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: What if most traders are making the same mistake with every single trade? What's the simple two-word framework that changes everything? Why don't even experienced traders understand the real secret to consistent profitability? What...

Summary: Dan Passarelli sits down with coach John Kmiecik to unpack why smart traders still struggle with losses, risk, and variance—and how to reframe decisions using Prospect Theory. They cover loss aversion, the disposition effect, myopic loss aversion, “house money” mental accounting, and practical coaching tactics (like multiple exits and portfolio-level thinking) to build discipline. Dan als...

In this episode, Dan Passarelli explores how biology and psychology quietly influence every trading decision—often more than logic or data. Through a story that begins in the Chicago trading pits and leads all the way to a conference in Hong Kong, Dan recounts his unexpected encounter with John Coates, a former Goldman Sachs trader turned neuroscientist and author of The Hour Between Dog and Wolf....

Have you ever "felt" something was off in the market—before you could explain why? In early 2021, Dan noticed unusual behavior across several stocks; days later, the Archegos Capital blow-up surfaced. It wasn't clairvoyance—it was his subconscious processing patterns his conscious mind hadn't connected yet. In this episode, Dan explores how biology and psychology shape trading decisions: why fear...

What If You Could Turn a Losing Trade Into a Winner—Without Taking the Loss? Most covered call and cash-secured put traders hit a wall when their trades go against them. The stock blows through their strike price, they're staring at a loss, and panic sets in. But what if there was a way to defer that loss, improve your odds, and keep your original credit intact? Enter the net-zero roll—the techniq...

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 e...

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" d...

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...

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-...

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 tr...

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 trad...

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...

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...

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...