When 70% of your net worth suddenly lands in a single stock, you're not managing a portfolio anymore — you're gambling. Brad and Jonathan tackle the terrifying euphoria of runaway winners with Brian Feroldi, who walks through exactly when to take profits, how to stomach the volatility, and why your tax bill might be the least of your problems. As prices surge on holdings like Tesla, Bitcoin, or Ethereum, investors face an uncomfortable reality: what started as a balanced portfolio can morph into a concentrated bet. The conversation covers risk management principles, including Brian's checklist for evaluating when to hold or trim positions, the emotional toll of watching massive swings in net worth, and practical strategies for rebalancing without triggering unnecessary tax consequences. Introduction to Runaway Winners [00:00:00] Discussion on Tesla and Investment Psychology [00:01:17] Situations where stocks or crypto investments significantly increase in value The emotional and practical implications of holding high-performing assets "The best problem to have is when an investment skyrockets, dominating your net worth." [00:04:08] Brian Feroldi's Investment Checklist [00:09:32] Brian shares his checklist for evaluating whether to buy more or sell "Consider limiting your exposure to volatile stocks to 10% of your portfolio." [00:07:07] Risk Management and Emotional Responses [00:22:03] Understanding volatility is crucial for realizing market returns Developing a plan to handle potential downturns helps manage emotional stress "High returns come with inherent short-term volatility." [00:24:40] "Understanding volatility is essential for realizing market returns." [00:23:46] Understanding Capital Gains and Selling Strategies [00:36:46] Tax implications on sales and when to reassess concentrated investments "Knowing when to reassess a concentrated investment is crucial." [00:34:12] Key Takeaways Define a clear percentage limit for individual investments to maintain portfolio balance [00:07:17] Consider creating an investor policy statement to outline your investment strategy and limits [00:33:50] Related Resources Brian's Investment Checklist [00:08:01] ▶ Listen Next: Ep. 351 — Year-End Tax Planning Strategies | Essential Listening