In this episode of EWA’s FIN-LYT Podcast, Jamison Smith, Drew Deimel, and Ben Ruttenberg tackle a common challenge facing high earners today: managing concentrated stock positions. With the rise of AI, tech, and the dominance of the “Magnificent 7,” many investors now hold a significant portion of their net worth in a single stock or sector. While this concentration may have created substantial wealth, it can also introduce serious risk and complexity as retirement or financial independence approaches.

The conversation explores why selling a highly successful stock can feel so difficult emotionally, especially when it represents years of loyalty, belief, or career success. Jamison, Drew, and Ben break down the psychology behind concentration risk and explain why diversification isn’t about giving up upside, but about protecting what you’ve already built. They also discuss how creating a clear, rules-based exit strategy can help remove emotion from critical financial decisions.

From there, the episode walks through practical strategies to reduce risk and manage taxes. These include direct indexing and tax loss harvesting, NUA strategies for company stock in retirement plans, donor advised funds, ETF tax free exchanges, Roth positioning, option strategies, and timing sales during lower income years. Each approach is framed around balancing tax efficiency, risk management, and peace of mind.

Whether you’re holding a single stock that’s grown far larger than intended or navigating equity compensation from a long career at one company, this episode offers a clear framework for turning concentrated wealth into long-term financial security.

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