RSUs, ESPP & Stock Options

“I'm looking at my ESPP shares and wondering if I should sell now or wait?”

CommonDeep Dive · 60 min · $170

Whether to sell ESPP shares now or wait often depends on how long the shares have been held, whether the sale would be a qualifying or disqualifying disposition, and how much of the gain may be tied to the discount that was taxed through payroll. The answer can also change based on current market value, your cost basis records, and whether you are trying to manage ordinary income, capital gains, or potential loss exposure. For many employees, the tax reporting detail matters as much as the investment decision, especially when shares were purchased through payroll deductions and held across multiple tax years. Working through the specifics with a CPA is the cleanest way to land on the right move.

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.