Jonathan Wellum: The Biggest Mistake Investors Make With Winning Stocks

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 biggest winners still deserve a place in your portfolio: https://bit.ly/4fktjJb Chapters: 00:00 Why Selling Is So Difficult 01:05 The First Reason to Sell 02:02 When a Stock Gets Too Expensive 03:00 Finding Better Opportunities 03:50 Why Trimming Beats Selling Everything 04:35 The Tax Trap Investors Face 06:20 Don't Confuse Stocks With the Market 07:31 Risk Starts With What You Don't Know 09:57 Rules for Selling Winners 11:15 Patience Is Your Greatest Edge Connect with us online: Website: https://www.wealthion.com X: https://www.x.com/wealthion Instagram: Instagram: wealthionofficial LinkedIn: LinkedIn: wealthion #Wealthion #Wealth #Finance #Investing #PortfolioReview #InvestmentAdvice #FinancialPlanning #WealthManagement #StockMarket #ValueInvesting #JonathanWellum #WarrenBuffett #LongTermInvesting #WealthBuilding #InvestSmart #Compounding #DividendInvesting #BehavioralFinance #FinancialEducation #PersonalFinance #Stocks #InvestingStrategy ________________________________________________________________________ IMPORTANT NOTE: The information, opinions, and insights expressed by our guests and our hosts do not necessarily reflect the views of Wealthion or the views of their respective employers. They are intended to provide a diverse perspective on the economy, investing, and other relevant topics to enrich your understanding of these complex fields. While we value and appreciate the insights shared by our esteemed guests and hosts, they are to be viewed as personal opinions and not as investment advice or recommendations from Wealthion or their respective employers. These opinions should not replace your own due diligence or the advice of a professional financial advisor. We strongly encourage all of our audience members to seek out the guidance of a financial advisor who can provide advice based on your individual circumstances and financial goals. Wealthion has a distinguished network of advisors who are available to guide you on your financial journey. However, should you choose to seek guidance elsewhere, we respect and support your decision to do so. The world of finance and investment is intricate and diverse. It's our mission at Wealthion to provide you with a variety of insights and perspectives to help you navigate it more effectively. We thank you for your understanding and your trust.