Why 90% of Option Sellers Still Lose — Even When They’re ‘Doing Everything Right

Christopher Uhl - OVTLYR and OVTLYR November 18, 2025
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Christopher Uhl - OVTLYR and OVTLYR

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Are you looking to save time, make money, and start winning with less risk? Then head to https://www.ovtlyr.com. Is selling options really more profitable than buying them? In this episode, we settle the debate once and for all with real math, real trades, and real outcomes. You’ll see why so many traders get seduced by the idea of selling options — and why that strategy can quietly destroy your account if you don’t understand the math behind it. This isn’t theory. It’s a data-driven breakdown of what happens when you sell puts on a stock that’s trending down, like MicroStrategy (MSTR), versus what happens when you buy puts in the same setup. Using OVTLYR’s behavioral analytics, we walk through exactly how expectancy, time decay, and leverage work together — and how most retail traders get it backward. Key insights from this video: ✅ Why selling options looks safe but carries unlimited downside risk ✅ How one losing trade can wipe out six to twelve winners ✅ What “extrinsic value” really means and why sellers can never profit from intrinsic value ✅ How theta decay, delta movement, and volatility crush the illusion of safety ✅ Why “cut your losses” isn’t just advice, it’s a survival rule ✅ The golden rule of leverage that every trader must understand ✅ How OVTLYR traders use expectancy models to pick smarter entries and exits We start by revisiting the fundamentals of options — long puts, short puts, and how both sides of the same contract mirror each other. You’ll see how buyers profit when prices drop, while sellers only win if the stock stays flat or rises. The catch? The moment the stock breaks into a downtrend, the seller’s losses start accelerating faster than they can recover. To drive it home, the episode dives into a detailed case study of selling a $380 MicroStrategy put that instantly turns against the seller. What begins as a $500 credit turns into a $3,800 loss per contract, even though the stock only drops 10%. That’s a 723% loss compared to the maximum possible gain — and it happens simply because of how options pricing works. This example shows the danger of the “high probability” myth. Selling options may give you an 84% win rate on paper, but that means nothing if your losses are six to ten times larger than your winners. The math simply doesn’t hold up. With OVTLYR’s tools, traders can clearly see when probabilities deceive and how to flip the equation in their favor by focusing on high expectancy setups instead of high win rates. The episode also reveals what legendary traders like Larry Hite taught about cutting losses, managing risk, and surviving volatility. You’ll discover why professional traders use systematic plans, why selling options often breaks the golden rule of leverage, and how to avoid the same trap that has ruined countless accounts. If you’re serious about understanding the truth behind buying versus selling options, this video will change how you think about trading forever. Gain instant access to the AI-powered tools and behavioral insights top traders use to spot big moves before the crowd. Start trading smarter today 👉 https://ovtlyr.com Subscribe for more real talk and real signals. No fluff, no noise. Just strategies that help you save time, make money, and start winning with less risk. 👉 https://www.youtube.com/@ovtlyrdotcom #OptionsTrading #StockMarket #Investing #SwingTrading #OVTLYR #BehavioralAnalytics #TradingStrategy #BuyingOptions #SellingOptions #LearnToTrade #FinancialEducation #RiskManagement #ThetaDecay #Leverage #HighExpectancy #PlanM #TradingPsychology #MarketAnalysis #InvestingTips #AITrading 📌 Video: https://www.youtube.com/watch?v=f-kfY0sUr8A&list=WL&index=5&t=722s NO INVESTMENT ADVICE. The information available through the Service is for general informational purposes only and references to specific securities, investment programs or funds are only for illustrative or educational purposes. No portion of the Service is a solicitation, recommendation, endorsement, or offer by OVTLYR or any third-party service provider to buy or sell any securities or financial instruments. You should not construe any such information or other material on the Service as legal, tax, investment, financial, or other advice. OVTLYR is not a fiduciary by virtue of any person's use of the Service. You alone assume the sole responsibility for evaluating the merits and risks associated with your use of any information on the Service. Nothing herein constitutes an offer or a solicitation of the purchase or sale of any security to any person in any jurisdiction in which such an offer or solicitation is not authorized. All purchases and sales of securities must and are to be made through a registered securities broker or dealer of your choosing with whom you have a contractual relationship and have agreed to accept such broker's or dealer's terms and conditions.

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