The Concentrated Stock Problem

The Concentrated Stock Problem · A free playbook

For the RSUs, options, and ESPP shares you’ve been meaning to deal with.

Instant access. No spam, ever.

The Concentrated Stock Problem playbook open on a tablet

Why smart people
stay stuck.

As a tech professional with stock options, you already know your portfolio is overconcentrated.

The hard part is that selling has a number attached to it (the tax bill), and holding doesn’t (the risk), so the decision feels lopsided even when the math isn’t. Add in loyalty to the company, excitement about where it’s headed, and the nagging fear of selling right before it doubles, and it’s no wonder even financially savvy people end up doing nothing.

The framework in this playbook isn’t about forcing a sale. It’s about buying back your choices, and building a game plan that works for your unique situation.

A handful of yes/no questions, small enough to answer tonight, turns “should I sell my company stock” into an actual path: monitor it, don’t let it grow, hold it deliberately with a cap, sell the recent lots, or run a glide path across a few tax years. No spreadsheets, and no advisor call required to get started. There’s nothing to gather except numbers you already have.

What’s inside.

A working mother takes a call at her laptop while her young daughter looks on

How to determine your important exposure numbers
A decision tree that sorts your situation onto a clear path
A short playbook for whichever path is yours
The additional complications that might adjust the plan (unexercised options, QSBS, a coming job change, a state move, very large gains)
A decision log to make the plan yours

Who it’s for.

Built for people whose compensation got complicated before their financial plan caught up: multiple vesting schedules, ISOs sitting next to RSUs, an ESPP nobody’s looked at since enrollment, and a portfolio that’s quietly become one bet instead of many. Think senior engineers, engineering managers, directors, and VPs at companies like Apple, Google, Meta, or SpaceX.

In practice, that looks like:

RSUs vest every quarter and you have no clear plan for the shares
A concentrated position in company stock that’s both an opportunity and a risk you try not to think about
Multiple brokerage accounts across current and former employers with no unified strategy
The nagging feeling that you should have a handle on this by now, given what you earn