When one stock makes up a disproportionately large portion of your portfolio, knowing what to do with it, especially if it's highly appreciated, can feel overwhelming.

In this episode, Tom talks Lauren through considerations when looking at a portfolio with a highly concentrated stock position. They walk through what concentration actually means, why context matters more than any single percentage threshold, and a range of strategies worth knowing about.

Topics covered in this episode:

• What a concentrated stock position is and when it typically signals a need for closer attention
• Why there is no universal answer, and how the bigger financial picture changes everything
• Tax loss harvesting and how losses elsewhere in a portfolio can help offset gains
• Direct indexing as a technology-driven way to generate losses at scale
• Exchange funds and the trade-offs that come with them
• Options overlays, including collars and covered calls, as tools for managing risk
• Slow selling as a straightforward, often underused approach
• Charitable gifting, direct stock donations, and donor-advised funds
• Estate planning considerations, including the step-up in cost basis at death

Many of these strategies involve significant tax and legal considerations. Throughout the episode, Tom emphasizes the importance of working collaboratively with your financial planner, CPA, and estate planning attorney before taking any action.

This episode is for informational purposes only and is not tax, legal, or investment advice. Please consult qualified professionals before making any financial decisions.