Stock Option Planning

Maximizing the Value of Your Stock Compensation

We evaluate your past and expected equity activity, helping to formulate a strategy that primarily optimizes for taxes. Whether you’re a founder, executive, or employee, we have the deep expertise to help you take advantage of your company-issued stock options.

Equity Compensation Strategy

Collaborative Work.
Stock Compensation Education.
Strategy Formulation.

Even smart people often do dumb things with stock options. A disciplined stock option exercise strategy can prevent some big mistakes and significantly increase the value of your option grant.

We provide you with the necessary resources to facilitate your decisions, explaining the options and risks associated with each choice.

We work collaboratively with you to achieve your goals and offer complete transparency around our own costs and compensation.

Customize our services to your needs, thinking long-term to build an individualized service that is right for you.

Frequently Asked Questions

How much should I exercise?
When should I exercise?
When should I sell my stock?
How much should I sell this year?
What should I sell first (e.g. NQSO / ISO / RSU)?
What is my tax bracket going to be in the next 5 years?
How much cushion do I have in your current tax bracket?
Should I sell the shares at vesting or hold them?
Should I sell the shares at vesting or hold them?

Equity Compensation Planning Areas


Incentive Stock Options (ISO)

Incentive stock options (ISOs) qualify for special tax treatment under the IRS Code and are not subject to Social Security, Medicare, or withholding taxes. However, to qualify they must meet criteria specified under the tax code. We help our clients create scenarios where they can minimize the tax impact of selling ISO stock.


Non-Qualified Stock Options (NQSO)

A nonqualified stock option (NQSO) is a type of stock option that does not qualify for special favorable tax treatment. We help clients develop a strategy that can help minimize the tax impact of exercising NQSOs.


Restricted Stock & Restricted Stock Units (RSU)

We help our clients create a unified vesting schedule (which includes Restricted Stock & RSUs). This allows our clients to make informed decisions.


Employee Stock Purchase Plan (ESPP)

An employee stock purchase plan (ESPP) enables you to purchase company stock often at a discount from the market price. We help our clients understand your company’s ESPP enrollment procedures, how to make changes, and whether the plan is a tax-qualified Section 423 ESPP or a nonqualified ESPP.

Sample Outputs

Stock Options Process

Introductory Call

Learn about your personal situation, explain our services, and disclose fully how we will be paid

Introductory Call

Sign the Agreement

Agree on the scope of work, timeline, and fees. We both sign the Financial Planning Agreement (FPA)
Sign the Agreement

Document & Data Gathering

Gather all the necessary documents, critical information, and calendarize future meetings
Document & Data Gathering

Meeting #1

In this meeting, we go over general strategy and the 1st scenario (base case).
Meeting #1

Final Meeting

Guided by your input, we meet to go over the other two (2) scenarios and decide on a plan of action (how much to exercise, what stock to sell, and when to sell).
Final Meeting

Curious about learning more? Let’s talk.