the high w-2 income playbook

A prospective client came to us with $2M tied up in a single stock. They felt stuck between two bad options: sell and trigger a massive capital gains bill, or hold and hope the stock kept performing.

Holding felt like the safer choice. But here's what most concentrated stockholders don't realize: from 1980 to 2020, 44% of the largest U.S. public companies suffered permanent declines of 70% or more. Looking at the Nasdaq-100 from 2001 to 2025, 75% of individual stocks underperformed the index, and 45% actually lost money.

They let you swap your pool your concentrated position into a fund alongside other investors in return for shares of a diversified portfolio, without triggering capital gains taxes today. Because no stock is sold, there's no taxable event.