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Selling Puts Is Easy Until One Starts Losing, Here's the Exit - Professional Investor Reacts

Sep 30, 2026 · 33m

Summary

The host shares a personal story of losing over $200,000 by selling puts and calls, using the experience to critique the "wheel" strategy and the "efficient market theory." He explains the mechanics of short puts, emphasizing that while they are bullish trades, they carry unlimited downside risk that violates the golden rule of leverage. The episode details a specific exit strategy based on multiples of the initial credit received, such as closing a trade when the loss reaches two times the premium collected. Finally, the host introduces the concept of convexity, illustrating how it benefit…

Topics discussed

Intro: Losing $200k and the golden rule of leverage Defining short puts and the bullish nature of the trade Why the Wheel strategy is broken and dangerous The 84% win rate trap and the cost of losses Case study: Holding losers on Apple in 2017 Calculating break-even points for short puts The problem with rolling and holding losing trades Critique of efficient market theory and trends Strategy: Closing puts at 2x the credit received The danger of cutting winners and holding losers Sponsor segments: LinkedIn, Gatorade, Amex Analogy: Short selling explained with a coffee mug Practical example: Setting exit points on Comcast The insidious nature of time decay and daily losses Estimating future option prices using current strikes Understanding convexity in long vs short options Outro and preview of earnings trade strategy
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