Options Boot Camp 386: Tax Tips for Options Traders

The Wheel Strategy is often touted as the ultimate "income generator," but most traders get it wrong because they lack the right mindset. In this episode, Mark Longo is joined by Dan Passarelli to discuss his brand-new book, Build Consistent Wealth with Options. They go beyond the basic mechanics to explore the three pillars of the Wheel, why most retail traders fail when they actually get assigned, and how to "rewire your brain" for probabilistic investing. Whether you're a passive investor or an active trader looking for an edge, this deep dive into the "Cycle-Recycle" method will change how you view covered calls and cash-secured puts forever. In this episode, we cover: The Three Pillars: Mindset, Objectives, and Methodology. The "Cycle-Recycle" Trade: Why the Wheel only works as a continuous system. The "Skate" vs. "Trade" Objective: How to decide if you actually want the stock. The PAS Indicator: Dan's custom tool for finding the "sweet spot" in premium. Alpha & Taxes: Maximizing your edge while managing the "silent killers" of wealth.

It's Tax Day on the network! Mark Longo and Dan Passarelli tackle the most requested topic of the season: how to keep the IRS out of your options profit. From the simplicity of the IRA "end run" to the mathematical beauty of 60/40 tax treatment on Section 1256 contracts (like SPX), the drill instructors break down how to optimize your tax bill. In this episode, we cover: The IRA Advantage: Why tax-deferred accounts are an options trader's best friend. Section 1256 Contracts: How to get long-term tax rates on short-term trades. The Complexity of Basis: Why multi-leg spreads can become an accountant's nightmare. Double Calendars: Dan clarifies the "Friday-Monday" spread strategy discussed in previous episodes. Defending The Wheel: Dan responds to critics who call his favorite strategy "garbage." Listener Mail Call: Binging 13 years of options education and overcoming the "overwhelming" start. Check out tastytrade - named best broker for options trading. Genius loves Company.

Can you handle the Double Calendar? In this episode of Options Boot Camp, the drill instructors tackle a strategy never before discussed on the network. Mark Longo is joined by the "Calendar King of Chicago" himself, John Kmiecik from Market Taker Mentoring (MTM), to break down the Double Calendar Spread. John reveals how the addition of Monday and Wednesday expirations for heavy hitters like Nvidia, Apple, and Tesla has completely shifted the risk-reward profile of time spreads. The guys also dive into the "Viceroy Special"—the definitive answer to when you should stop trading options and just buy the stock. On the Drill Floor: The Double Calendar: How to trade two ranges at once with lower cost and risk. The Mid-Week Edge: Leveraging new Monday/Wednesday expirations to your advantage. Spicy Volatility: Strategies to lean into (and which to avoid) when the VIX hits 30. The Rate Cut Debate: Is the market pricing in a pivot or more pain? Whether you're looking to harvest premium or survive a market whipsaw, this episode turns complex concepts into actionable drills. Genius Loves Company: See why Investopedia named Tastytrade the best broker for options in 2024. Get low pricing, elite education, and a support team that actually gets how traders trade at tastytrade.com/podcasts .

Happy April Fool's Day! In this special "Options Fool's Day" edition of Options Boot Camp, Mark Longo is joined by guest instructor John Kmiecik from Market Taker Mentoring (filling in for Dan Passarelli, who may or may not be riding donkeys in Santorini). While the spirit of the day is lighthearted, the lessons on what NOT to do are very real. The duo dives into a "too good to be true" scenario involving high-ratio spreads, exploring the seductive but dangerous world of "free lunch" trading. We also have a bit of fun with some "breaking" (and completely fabricated) OCC volume numbers to see if the golden goose of options trading is finally cooked. In this episode, we cover: The March Pro Trading Crate Giveaway: We crown our latest winner! The "Infinite Return" Myth: A deep dive into ratio spreads, 1x4 lopsided trades, and why "zero outlay" usually comes with a massive hidden price tag. Market Satire: Analyzing the (fake) cracks in options volume and what the real state of the industry looks like. Education vs. Pranks: Distinguishing between sound strategy and the "nonsense" that can lead a small account to ruin. Disclaimer: This episode contains April Fool's satire. Please do not attempt 1x4 net short ratio spreads at home unless you enjoy financial ruin!

Is the "Wheel Strategy" making you nervous in a high-volatility market? In this episode, Mark Longo and Dan Passarelli field listener questions about navigating black swan fears, the "Greeks" you should watch when the market moves fast, and whether the AI narrative in Nvidia still has legs. Dan also prepares for his upcoming trip to Greece by getting some questionable advice from Mark about riding donkeys in Santorini and ordering "Euros" at the local taverna. Key topics covered in this episode: The Wheel Strategy vs. Credit Spreads: Is it time to cap your downside when the VIX hits 22? Vega and Gamma Focus: How your attention should shift between Greeks in a fast-moving market. Nvidia (NVDA) Outlook: Dealing with underwater bull call spreads after the GTC conference. 0DTE Expansion: Will we see more zero-day contracts added to the roster this year? UVIX vs. SVIX: A deep dive into leveraged and inverse VIX products and how to use them to hedge "weekend risk."

Fall in, recruits! Mark Longo is back in the Chi-Town studio, braving the cold to get you into peak options trading shape. With the energy markets in a state of high alert and WTI futures seeing massive volume, your drill instructors are here to break down the complex world of oil. In this week's Options Drills, Mark and Dan Passarelli explore: Going to the Source: The benefits of trading WTI and Brent futures for pure, one-to-one correlation. The USO Dilemma: A deep dive into the much-maligned US Oil Fund. We discuss the "Negative Oil" ghosts of 2020 and the impact of negative roll yield. Equity Surrogates: Using XLE (Energy Select Sector SPDR) and individual giants like Chevron (CVX) as portfolio proxies. The Volatility Play: How to view geopolitical crises through the lens of VIX, UVIX, and SVIX. Whether you're looking to generate income or hedge against $100+ crude, this is your tactical briefing.

To maximize your reach, I've tailored these descriptions to how people actually find content on each platform. For Libsyn, the focus is on scannability for podcast apps and Google search. For YouTube, the focus is on "Watch Time" signals, Chapters, and keywords that trigger the video algorithm. 1. Libsyn Show Description (RSS & Podcast Apps) Focus: Clear summary, scannability, and high-value links. Options Boot Camp 381: We've Got Two Questions...One for Each of Ya! Is the "Wheel" turning against you? Are you obsessing over direction while the pros look elsewhere? In this episode of Options Boot Camp, your drill instructors Mark Longo and Dan Passarelli tackle a rapid-fire mail call to help you navigate the complexities of the options market. From the viability of the Ratio Stock Repair strategy to the psychological divide between beginner and veteran traders, we break down the tactics you need to survive and thrive. We also dive deep into the changing landscape of Crypto Options, specifically how the explosion of IBIT (BlackRock's Bitcoin ETF) has shifted market skew to look more like traditional equities—and what that means for your income-generating strategies. In This Episode: The Wheel Strategy: Is Ratio Stock Repair the best escape hatch for a losing wheel trade? Beginner vs. Pro: Why novices fixate on Delta while experts prioritize Volatility and Time. 0DTE Popularity: Analyzing the massive liquidity surge in equity zero-days. The 90% Myth: Debunking the classic "options expire worthless" statistic. Time Spreads (Calendars): The one thing most traders get wrong about Volatility Term Structure. Bitcoin Evolution: How IBIT has "democratized" Bitcoin options and changed the skew. Check out more from the Options Insider Radio Network: Pro Trading Crate: theoptionsinsider.com/pro Education & Brokerage: tastytrade.com/podcasts Advanced Training: markettaker.com

Fall in, recruits! Today, we're taking one of the most classic range-bound strategies and putting it through the 0DTE (Zero Days to Expiration) ringer. Is the Iron Condor the ultimate strategy for the current market environment, or a recipe for disaster? Mark Longo and Dan Passarelli break down the "Great Iron Condor Renaissance." We move past the basic definitions and get into the "drills," applying this strategy to the new Monday and Wednesday weekly options in the Mag 7. In this episode, we cover: The Iron Condor Refresher: A deep dive into the mechanics—selling strangles vs. selling spreads. 0DTE Strategy: Why these are getting hot again and how to pick your "danger zone." The Apple ($AAPL) and Nvidia ($NVDA) Experiments: We look at real-time 0DTE setups to see where the "juice" is hiding. Strike Selection: Why Dan prefers support and resistance over standard deviation in the 0DTE world. Pro Trader Crate: We announce this month's lucky winner! Check out more from the Options Insider Radio Network: Pro Membership: theoptionsinsider.com/pro Education & Brokerage: tastytrade.com/podcasts Dan's Training: markettaker.com/reg

In this episode, the "drill instructors" Mark Longo and Dan Passarelli return for Round 3 of their battle against the machines. With Nvidia (NVDA) earnings taking center stage, they put a premium AI model to the test: can a chatbot actually teach you how to trade the "volatility crush," or is it just repeating bad habits? In this episode, you'll learn: The AI Framework: Analyzing the 6-step checklist for earnings success. The Volatility Crush: Why buying "cheap" weekly calls is often a trap. Strategy Showdown: Comparing Iron Condors and Credit Spreads vs. Long Straddles. Risk Management: Why the 1% to 3% rule is the only way to survive earnings season. Ready to trade options and futures yourself? Go to https://tastytrade.com/podcasts to get on the tastytrade site and start trading today.  

On this episode of Options Boot Camp, hosts Mark Longo and Dan Passarelli break down the real-world price tag of portfolio protection. Using current market examples, they walk through what it costs to hedge SPY with puts across different strikes and timeframes, why "insurance" isn't free, and how volatility levels can dramatically change the math. They also tackle the evergreen debate: SPY/SPX puts vs VIX calls—and why VIX products may behave more like a speculative "kicker" than a true one-to-one hedge. Plus, a listener-driven roundtable on hedging with gold and metals, the clash between 0DTE and potential 24/5 trading, and a practical primer on volume vs open interest (and why the bid/ask spread often tells the real story). Key topics include: The real cost of hedging SPY (near-term vs longer-dated puts) Strike selection, "deductibles," and the insurance analogy How elevated volatility impacts hedge pricing VIX calls as a hedge (and why timing matters more than ever) Hedging with metals: correlation, pros/cons, and when it fails 0DTE vs 24-hour trading: are these trends incompatible? Volume vs open interest for liquidity (and what to check first) Hosts: Mark Longo (The Options Insider Media Group) & Dan Passarelli (Market Taker Mentoring) This episode is brought to you by tastytrade — check them out for powerful options trading tools, education, and low pricing at tastytrade.com/podcasts.