RSUs, ESPP & Stock Options

“What's better for me tax-wise: selling my ESPP shares now or holding them?”

CommonDeep Dive · 60 min · $170

The tax tradeoffs for ESPP shares often depend on how long the shares have been held, whether the sale is a qualifying or disqualifying disposition, and how much the stock price has moved since purchase. In many cases, the answer also turns on the discount received through the plan, any ordinary income that may be recognized, and whether the shares are concentrated alongside other employer stock. Holding can change the character of the gain, while selling now can simplify recordkeeping and reduce exposure to market swings, so the better fit often depends on timing and your broader income picture. A CPA who reads your specifics can usually tell you, in plain English, where this lands.

In your 60-minute session, the KGOB advisor handling it will:

Read your exact situation and tell you, in plain English, what’s actually going on.
Lay out your options and the trade-offs — no jargon, no judgment.
Give you a clear next step you can act on, whether that’s with us or on your own.