Most investors obsess over what to buy. Very few have a clear, repeatable plan for when to sell.

In this episode of Stock Spotlight, I break down the risk-aware and thesis-driven selling framework I use to protect capital early, avoid deep losses and continuously upgrade portfolio quality over time. Selling is not about calling tops. It is about defining your downside before emotion sets in, managing uncertainty when conviction is still forming and only staying invested when the business continues to validate the original thesis.

I walk through how I set downside boundaries during the first 0-90 days of ownership, why thesis drift becomes the most important long-term sell signal and how I use KPIs to keep the decision grounded in evidence instead of narrative. You’ll hear exactly how this played out in two real examples from my own portfolio, including Duolingo and e.l.f. Beauty, where the “why” behind the sell mattered as much as the timing.

I finish by sharing the five questions I now ask before exiting any position. If you’re a long-term investor who wants a structured way to sell with discipline instead of regret, this episode lays out the full framework.

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00:00 Opening

01:12 Why Selling Matters

02:31 Early Risk Management

05:13 Thesis-Driven Selling

09:05 Reallocating Capital & Improving Quality

10:58 Case Study - $DUOL

14:18 Case Study - $ELF

17:17 5 Questions to Ask Before Selling

17:57 Closing

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Intro Music: Andrey Rossi – Seize the Day

Outro Music: Ra – Prospect

*Music provided by Uppbeat Premium

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Subscribe to my YouTube channel: https://www.youtube.com/@stockspotlightpodcast

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Disclosure: The host of Stock Spotlight is not a licensed financial advisor. The information and opinions shared during the show are for entertainment purposes only.