07/22/2026
For many Chicago executives, a concentrated stock position is a double-edged sword: it is the primary source of your wealth, but also your greatest portfolio risk.
Whether you are holding RSUs, stock options, or founder shares, having a single company represent a large percentage of your net worth can be unsettling. The challenge is not just deciding to diversify, but determining how to do so without triggering an immediate and substantial tax bill.
In our latest blog post, we explore three tax-aware strategies specifically for executives in Chicago, Barrington, and across the North Shore:
1. Systematic Diversification & Rule 10b5-1 Plans: A structured approach to help spread taxable gains over multiple years while managing insider trading restrictions.
2. Exchange Funds (Swap Funds): A method to achieve diversification by pooling shares with other investors, potentially deferring capital gains taxes under specific conditions.
3. Equity Collars & Charitable Remainder Trusts (CRTs): Sophisticated tools designed to help manage downside risk or integrate your philanthropic goals into your exit strategy.
At Virtue Asset Management, we operate under a fiduciary standard, providing personalized, boutique-style advisory services to help high-net-worth families navigate these complexities.
Read the full guide on our website: https://virtueam.com/concentrated-stock-positions-3-tax-aware-strategies-chicago-executives-should-understand/