09/10/2026
Sold your tech stock or RSUs before making a tax plan? Read this. 👇
A client came to us after selling 100% of their stock.
Moving out of a concentrated position was the right call for their portfolio—but doing it without a tax plan created a massive, unnecessary capital gains tax bill for April.
Here is the truth about RSUs and big stock sales: Order of operations is everything.
If you sell first and ask questions later, you're forced into reactive damage control. If you plan before hitting the sell button, you can build a tax shield that absorbs those gains.
If you’ve already hit "sell" this year, here’s how we mitigate the damage before December 31:
1️⃣ Isolate the Tax Bill: Set aside your worst-case estimated tax owed in cash now so there are zero surprises or scrambles come tax time.
2️⃣ Harvest Losses via Direct Indexing: Move remaining cash into a custom index portfolio that tracks top holdings (like the S&P 500) while actively harvesting individual stock losses to lower this year’s gain.
3️⃣ Leverage Strategic Giving: If charitable giving is part of your goals, utilize a Donor-Advised Fund (DAF) before year-end to knock out another significant portion of taxable gain.
The Key Takeaway for Equity Holders:
The best time to plan for an RSU or stock sale is before you press the sell button. Running a tax-loss harvesting strategy alongside your stock position for a year or two creates a buffer of offsets that eats up future gains before they hit your return.
Selling first is fixable—it’s just more expensive than it needed to be.
📲 Holding vested RSUs or planning a major stock sale? Don't leave money on the table for the IRS.
👉 Book a strategy call with our team today, and let’s optimize your tax bill.
