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Wealth

How to Unwind a Concentrated Position

Three ways to reduce risk from a single large stock holding, like an RSU grant, without selling it all at once or triggering a huge tax bill.

Educational only. Not financial, tax or legal advice, and not a recommendation to buy or sell anything. Any dollar amounts or tax rules here are tied to the year they were written and change annually — verify current figures and talk to a qualified professional about your own situation.

A concentrated stock position is when a significant portion of your net worth is tied to one stock. This can happen through RSU grants, a long-held founder stake, an inheritance, or simply a stock that has run up over time. While a concentrated position can be a great wealth builder, it also increases risk: if the stock drops, so does your financial security.

When you're ready to unwind a concentrated position, rather than selling everything at once, here are three strategies to reduce risk while preserving upside potential and triggering minimal taxes.

Exchange Funds – Diversify Without Selling Immediately

  • Exchange funds (not ETFs) allow you to pool your stock with other investors and receive a diversified portfolio in return.
  • Since you're not selling, you defer capital gains taxes, making this an attractive option for high-net-worth investors.
  • After a set holding period (often seven years), you receive a basket of stocks, reducing exposure to a single company.

Direct Indexing – Custom Diversification With Tax Efficiency

  • Instead of selling in bulk, direct indexing allows you to gradually shift into a diversified portfolio.
  • You can harvest tax losses from underperforming stocks to offset capital gains on the concentrated position.
  • This strategy mimics an index fund but with more control over tax and risk management.

Options Overlay – Protect and Profit Without Selling

  • Use protective puts to hedge downside risk while keeping your stock.
  • Sell covered calls to generate income and reduce exposure at predefined price levels.
  • Options strategies allow for flexibility, letting you manage risk while maintaining potential upside.

Key Takeaway

A concentrated position can happen for many reasons, especially from RSUs. Concentrated positions can be risky, but exchange funds, direct indexing, and options overlays offer ways to diversify without an immediate tax hit.

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