About this episode

Jonathan Wellum discusses the critical decision of when to sell winning stocks and the common mistakes investors make.

When should you sell a stock that's been one of your biggest winners? According to veteran portfolio manager Jonathan Wellum of ROCKLINC Investment Partners, the default answer is almost never...unless the investment thesis has fundamentally changed. In this conversation with Maggie Lake, Wellum explains why long-term investors often hurt returns by selling too early, chasing market trends, or reacting emotionally to volatility. He outlines the three legitimate reasons to sell a stock, discusses why taxes shouldn't dictate investment decisions, explains how Warren Buffett approached trimming Apple, and shares why patience remains one of the greatest competitive advantages investors have. He also offers practical guidance on managing concentration risk, evaluating intrinsic value, and avoiding costly behavioral mistakes. If you're wondering whether it's time to take profits—or simply stay the course—this interview provides a disciplined framework for making better investment decisions. 💡 Jonathan Wellum says the hardest investing decision isn't what to buy—it's knowing when to sell. Get a free portfolio review from Jonathan and the team at ROCKLINC to determine whether your…

People in this episode

Host: Maggie Lake

Guest: Jonathan Wellum

Topics covered

• investment strategy
• stock selling
• long-term investing
• behavioral finance
• portfolio management

Keywords

• selling stocks
• investment thesis
• market trends
• concentration risk
• intrinsic value

Mentioned in this episode

Organizations: ROCKLINC Investment Partners

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