Wealth Building With Options

Dan talks with professional options trader, quantitative strategist and author Euan Sinclair. With nearly 30 years of experience, Euan shares his data-driven perspective on volatility, risk and why the Wheel has more academic support than many popular retail strategies.

Dan and Euan also challenge several common options beliefs, including the idea that time decay automatically creates an edge. They discuss why every options trade is ultimately a volatility trade, the importance of understanding your objective and why simple, well-tested strategies often beat overly complicated ones.

In this episode, Dan explains how discounted cash flow models can help investors estimate what a stock may actually be worth. He breaks down the basic components of a DCF model, then uses real stocks to show both its usefulness and its limitations.

Dan also explains why a DCF valuation should never be treated as a prediction. Assumptions matter, small changes can produce very different results and DCF analysis works best as one part of a broader stock-selection process.

In this episode, Dan explains how volatility skew can help traders make more informed decisions when selecting strikes for covered calls and cash-secured puts. He starts with the volatility risk premium behind option selling, then breaks down how implied volatility can vary across different strikes on the same stock. That difference, known as vertical skew, can reveal where option buyers and sellers are creating unusual pricing opportunities.

Dan explains the typical volatility pattern, why lower-strike options often carry higher implied volatility and what it means when that relationship changes. Using a real-world example, he shows how strong...

Dan tackles a part of trading that rarely gets discussed: how to talk with your spouse or partner about putting family money into a trading account. Drawing on his own experience and more than three decades of working with traders, Dan explains why concerns about risk, losses and financial responsibility are reasonable, especially when your partner doesn't yet have the context behind your trading plan.

Dan walks through the conversations traders should have before committing money, time or resources to trading. He covers building a clear trading plan, setting risk limits, preparing for drawdowns, getting proper education...

Dan challenges the idea that calm, sideways markets are always best for trading the Wheel. His argument is more counterintuitive: Volatile markets can create some of the best opportunities for covered calls and cash-secured puts, provided traders have clear objectives, understand how to adjust positions and are comfortable with the stocks they may end up owning.

Dan explains why falling markets can create attractive buying opportunities through cash-secured puts, while sharp rallies can create opportunities to sell covered calls at higher strikes. He also digs into adjustment techniques such as net zero rolls and shows how “wish li...

In this episode, Dan tackles one of the most overlooked parts of trading the Wheel: accurately tracking results over time. A single cash-secured put or covered call doesn't tell the whole story. To understand how a Wheel position is actually performing, you need to account for every option credit and debit, assignment, stock transaction and completed cycle associated with the underlying.

Dan explains why brokerage platforms aren't designed to track a long-running “big cycle” of Wheel trades and why reconstructing performance after the fact can become a tedious spreadsheet exercise. He walks through the challenges of calculating resu...

Dan explains how certain Wheel trades can create an opportunity to “double dip” by collecting option premium from both sides of a stock position. The strategy is a covered strangle, combining stock ownership with a short call and a short put. Dan uses a real position in The Metals Co. (TMC) to show how this setup can develop naturally while trading the Wheel.

Dan walks through why he chose to sell puts instead of covered calls while TMC was trading near $4, what happened when one tranche of those puts was assigned and how the additional shares opened the...

Dan sits down with Kevin Davitt, head of Nasdaq's Index Options Content, to explore the evolution of options markets and how index options can fit into strategies familiar to individual investors. Kevin brings experience as an options market maker and former senior instructor at the CBOE Options Institute, giving him a unique perspective on how options markets, technology and education have changed over the years.

Dan and Kevin dig into whether the Wheel can be adapted to cash-settled index options such as NDX and XND. They discuss the important differences between index options and traditional equity options...

Dan sits down with Robert Savage of Savage Markets to explore the macro forces shaping today's investment landscape. With more than 40 years of experience in global markets, Robert brings a unique perspective from his career in foreign exchange, commodities, options, research and market strategy. He explains how options data can provide forward-looking information and why investors should pay attention to forces well beyond the individual stocks in their portfolios.

Dan and Robert discuss prediction markets, currency moves, the Japanese yen, interest rates, inflation, supply shocks and the possibility of stagflation. They also examine how these forces can...

AI can be a powerful research assistant for investors, but only if you know how to ask the right questions. In this episode, Dan shares the AI prompts he uses to research potential stock investments, analyze companies and dig deeper into fundamentals. From simple questions about what a company actually does to more advanced analysis of financial ratios, earnings trends and discounted cash flow, Dan demonstrates how AI can help investors conduct more thorough research.

Dan also explains one of the biggest dangers of relying on AI for investment research: inaccurate or outdated information. He shares how...

As he does during his live weekly Wealth Builder Trade Room, Dan takes listeners inside his own IRA to demonstrate how he manages Wheel trades in real time. He walks through several positions and explains the thought process behind deciding whether to sell puts, write calls, roll an existing position, wait for a better opportunity or simply let the trade develop.

Using examples from his actual portfolio, Dan shows how the Wheel is less about finding one perfect trade and more about methodically managing a series of decisions. He covers assignment, net zero rolls, earnings volatility, technical...

Dan sits down with Market Taker Mentoring head coach John Kmiecik for a candid conversation about the Wheel strategy, what they’re seeing from real traders, and why a strategy that can sometimes feel “boring” may be exactly what many investors need. John shares how students are incorporating the Wheel into their portfolios, including traders with smaller accounts, and why the strategy can provide a very different experience from the constant ups and downs of swing trading.

Dan and John also dig into what makes the Wheel work, from the volatility risk premium and changing implied volatility enviro...

Finding a great Wheel trade starts long before choosing a strike price or expiration. In this episode, Dan walks through his step-by-step process for finding candidates for covered calls and cash-secured puts. The process begins with a fundamental distinction: Are you evaluating a stock or ETF you already own or searching for a completely new opportunity? From there, whether you want to skate and collect premium or trade into or out of the stock determines which tools matter most.

Dan explains how he combines fundamental analysis with technical tools including support and resistance, RSI and his PAS...

In Part 2 of this series, Dan expands on the metrics every Wheel trader should understand by focusing on break-even calculations, cumulative discount effect, stock price basis and the often-overlooked role of interest rates. These metrics provide a more complete picture of long-term performance by tracking the combined impact of option premium, assignments, stock price movement and capital efficiency rather than evaluating each trade in isolation.

Dan also explains why different calculations require different stock price references, how cash and interest rates influence option pricing and trade selection, and why investors should evaluate Wheel trades as part of...

Dan introduces the performance metrics he relies on to evaluate every Wheel trade. Rather than focusing on option premium alone, he explains how measuring returns correctly helps investors compare opportunities, improve decision-making and treat trading like a business. By understanding the numbers behind each trade, investors can benchmark their performance and make more informed choices over time.

Dan breaks down the calculations behind static return, annualized return, if-called return, skate return on cash and skate yield, explaining not only how they're calculated but why they matter. He also explores the psychological benefits of using objective metrics to...

In this episode of Wealth Building With Options, Dan Passarelli walks through a real-world covered call case study using AT&T stock. Rather than focusing on theory, Dan explains the decision-making process behind managing a dividend-focused Wheel strategy—from entering the trade with cash-secured puts to determining when it's time to exit using covered calls.

If you've ever wondered when to sell a covered call, how to balance dividend income with option premium, or how to think like a professional options trader instead of chasing individual trades, this episode is for you.

In This Episode

Dan welcomes Market Taker Mentoring Head Coach John Kmiecik for a behind-the-scenes discussion about how real investors are using the wheel strategy. Drawing from John's experience coaching hundreds of options traders, they explore the common habits, misconceptions and breakthroughs they see from beginners to advanced traders, along with the techniques that consistently lead to better results.

They also discuss why the wheel has become one of the most popular options strategies, the psychology behind cash-secured puts vs. covered calls, the importance of understanding synthetic positions and why trade management often sets successful wheel traders apart. They also...

Dan explores the trade objective approach to cash-secured puts by breaking down a real Adobe trade from his own account. Inspired by Warren Buffett's well-known use of cash-secured puts, Dan demonstrates how investors can use them strategically to acquire high-quality stocks at attractive prices or generate income while waiting for the right opportunity.

Throughout the episode, Dan shares every step of his decision-making process, from evaluating Adobe's valuation and technical support levels to selecting the ideal strike price and expiration. He also explains how cumulative option premium, rolling strategies and changing market conditions influence long-term results, giving...

My Exact Process for Covered Calls Episode Summary

What separates a covered call from a consistently profitable covered call?

In this episode, Dan Passarelli walks through an actual Amazon covered call from start to finish, explaining every decision he made—from selecting the expiration and strike price to managing the trade after entry. Along the way, he introduces the PAS (Price History Anchored Strike) Indicator, the proprietary tool he developed after discovering that no existing technical indicator was designed specifically for option traders.

Rather than teaching theory, Dan breaks down his real-world decision-making process, showing ho...

Can the Wheel Strategy be successfully packaged into an ETF?

In this episode, Dan Passarelli sits down with Rob Pascarella, co-founder of Peerless ETFs and Head Trader of the Peerless Option Income Wheel ETF (Ticker: WEEL), to discuss the creation of the first ETF designed to systematically implement the Wheel Strategy.

Rob shares his journey from engineer to portfolio manager, explains why put-selling remains largely overlooked in the ETF industry, and reveals how WEEL seeks to generate income through a disciplined, rules-based options process.

Dan and Rob also explore volatility, diversification, risk management...

Dan walks listeners through a real-world cash-secured put case study using Target Corp. (TGT) as an example. He demonstrates how to evaluate a trade from start to finish, including technical and fundamental analysis, option selection, trade execution, liquidity considerations, and management planning. The episode emphasizes that successful wheel trading is not just about understanding option mechanics, but about developing a repeatable process for finding, executing and managing high-probability trades.

Dan sits down with Steve Quirk, Chief Brokerage Officer at Robinhood Markets, for an in-depth conversation about retail investing, options trading, market behavior and the evolution of the modern trader. Steve shares insights from nearly four decades in the industry—from starting on the trading floor after the 1987 market crash to helping shape trading technology at TD Ameritrade and Robinhood. Dan and Steve discuss what successful investors do differently, why retail traders may be more sophisticated than they’re often given credit for and how options strategies like the wheel fit into a long-term wealth-building plan.

Dan explores a counterintuitive idea: Sometimes the best way to use the Wheel Strategy is not to use it at all. While covered calls and cash-secured puts can be powerful tools for generating income and reducing portfolio volatility, there are market environments—particularly strong trends and low-volatility conditions—where selling options may limit opportunity more than it helps. Dan explains how wheel traders must balance collecting premium against participating in major directional moves, and why understanding market context is critical to long-term success.

In this episode, Dan explains how covered calls and cash-secured puts can still work in trending markets if traders understand when to roll, when to close and how to plan before the trade is ever entered. Using examples from Build Consistent Wealth With Options, he breaks down how support, resistance, premium, market regime and trader psychology all factor into managing wheel trades when the stock moves farther than expected.

In this special episode, Dan and Market Taker Mentoring head coach John Kmiecik discuss one of the biggest challenges traders face: consistency. They explore why smart, hardworking traders still struggle despite studying strategies, taking courses and spending years trying to improve — and why the missing piece is often structure, accountability and personalized coaching rather than more information.

Dan and John share powerful stories from their own trading careers; lessons learned from mentoring traders around the world; and practical insights into the psychology of execution, discipline, emotional control, and building a trading plan that actually fits a trader’s pe...

Dan sits down with longtime options industry veteran Kevin “Lex” Luthringshausen to discuss the evolution of options trading, retail trading technology and what separates successful traders from struggling ones. From Lex’s early days as a market maker at the Chicago Board Options Exchange to today’s AI-driven trading landscape, the conversation explores how the industry has transformed over the past four decades.

Dan and Lex also dive into covered calls, cash-secured puts, trade management, market efficiency, automation and the rise of zero-DTE trading. Along the way, Lex shares practical wisdom about discipline, emotional control and why having a...

Dan breaks down which market environments are most favorable for the wheel strategy and why. While sideways, range-bound markets create ideal conditions for consistent income through covered calls and cash-secured puts, trending markets introduce new challenges. Dan also dives into the psychological side of trading, explaining how regime changes can trigger emotional responses that impact decision-making and performance.

In this milestone episode, Dan celebrates the official release of his new book, Build Consistent Wealth With Options. He reflects on the journey behind the book—years of trading experience, teaching and refining the wheel strategy—and thanks listeners for being part of that process through the podcast. What began as a companion to the book evolved into a full educational series, documenting the concepts and insights that ultimately shaped the final product.

Dan emphasizes that this book represents the culmination of decades of work and that, unlike many trading authors, he chose not to hold anything back...

Dan breaks down the poor man’s covered call, a strategy that uses a longer-term in-the-money call instead of stock, paired with a shorter-term out-of-the-money call sold against it. The result is a capital-efficient alternative to a traditional covered call, with less downside exposure but its own tradeoffs in time decay, volatility and assignment risk. Dan explains how to set these trades up, what greeks matter most, and how to manage and roll them effectively.

Dan explains why cash management is more complicated than it first appears for wheel traders. It’s not just about how much of your account is “in cash,” but how much is actually available to trade, manage positions and respond to new opportunities. Dan walks through how account size, skill level, market conditions and strategy type all affect cash allocation, and he shares a real-world example of why being “fully invested” can leave you unable to close or roll a covered call when you need to.

In this episode of Wealth Building with Options, Dan Passarelli tackles a unique—but very real—challenge faced by investors with large, concentrated stock positions.

If a significant portion of your wealth is tied up in a single stock—whether from years at a company, stock-based compensation, or inheritance—you may face a difficult tradeoff:

But what happens when you’re generating income with covered calls… and suddenly get assigned?

That’s where things can get complicated.

What You...

When markets crash, most investors panic.

They react emotionally. They sell at the worst possible time. And they miss the very opportunities that could change their long-term results.

In this episode, Dan Passarelli breaks down what really happens during market selloffs—and how disciplined traders can position themselves to take advantage of fear instead of being controlled by it.

Key Topics

Dan breaks down how to think about in-the-money covered calls and in-the-money cash-secured puts. These trades can be powerful tools when you want to sell stock more efficiently or buy it at an effective discount, but they require a different mindset. Dan explains how to separate intrinsic value from time value, how to evaluate the real benefit of the trade and how to weigh assignment probability against the risk of missing a larger move.

Dan explains when option assignment is predictable, when it isn’t and why understanding the other side of the trade matters. He breaks down expiration mechanics, strike-price pinning, early exercise around dividends, deep in-the-money put assignment and hard-to-borrow stocks. He points out that while assignment is usually straightforward, in certain situations strategy and market mechanics can make outcomes much less obvious.

Dan continues the conversation on liquidity, execution and trade management by focusing on good-till-canceled (GTC) orders, gap risk and the trade-offs of handling illiquid options. He explains when it makes sense to let options expire rather than overpay to close them, why rolling illiquid in-the-money options is often impractical and how traders can still create solid opportunities in wide markets.

Dan is joined by returning guest John Kmiecik to unpack the real-world consequences of trading illiquid options (wide bid/ask spreads, low volume/open interest and “roach motel” trades you can’t exit efficiently). They also discuss how expanding strike/expiration listings can fragment liquidity, even in big names, and when a “one-sided” wheel trade can justify holding through expiration.

Dan explains why execution price is the one place retail traders truly “compete” with market makers and how improving it can dramatically reduce slippage, the biggest hidden cost in options trading. You’ll learn how market makers manage risk (delta-neutral hedging) and why they demand compensation through the bid/ask spread, plus practical tactics for middling markets, using resting orders and handling illiquid options without getting trapped by wide spreads.

Dan breaks down the real costs of trading and why commissions, while worth managing, are rarely the biggest threat to your returns. The true hidden expense is slippage, driven largely by liquidity. He walks through how to evaluate option liquidity using bid-ask spreads, size, volume and open interest, and sets the stage for mastering the critical execution skill of middling the market.

Dan explains how wheel-style covered calls can turn “meh” or even speculative stocks into strategic, risk-managed income plays through cumulative premium and even share-loan income. He also explores the often-overlooked reality that trading is a business with costs, especially taxes, commissions/fees and slippage. He shares two real trade stories to show how premium collection can create downside cushion and discusses practical tax considerations.

Dan shifts from cash-secured put “double threat” setups to covered calls, especially the skate objective (keeping premium without assignment). He explains why technical analysis is often the most practical way to add edge to covered call strike selection, particularly by using resistance, momentum tools like RSI and realistic range expectations. He also walks through how to sanity-check any setup with annualized yield and what to do if the stock runs through your strike (accept assignment vs. roll proactively).