Concentrated stock glidepath calculator

State rates by state: CA 13.3%; NY 10.9% (+ NYC ~3.9%); WA / TX / FL / NV / WY 0%. Most states tax LTCG at the same rate as ordinary income; a handful (AK, FL, NV, SD, TN, TX, WA, WY) have no income tax. The 3.8% federal NIIT is calculated automatically — it applies to both long-term and short-term capital gains when MAGI exceeds $200K (single) or $250K (MFJ).²

Reading the glidepath

The table models equal annual installments at a flat basis ratio and constant stock price. Three variables you control change the real outcome significantly:

• Speed vs. tax cost. Selling faster concentrates your gains in fewer tax years. A $2M position sold over 1 year may push $1.5M of gain into the 20% federal bracket; spread over 4 years, the same position might stay mostly in the 15% bracket. The difference on a $2M position can exceed $100K in federal tax alone.
• Holding period by lot. Shares acquired more than one year ago qualify for LTCG rates. RSUs that vested within the past 12 months are short-term and taxed at ordinary income rates in the year you sell. If your lockup just expired on shares from a recent vest, check your specific vest dates — switching one lot from short-term to long-term treatment can cut your rate by 15-20 percentage points.
• Lot selection within a year. If you have multiple RSU tranches with different vest dates and prices, you choose which lots to sell each year. High-basis lots reduce taxable gain. Earliest-vest lots that have already crossed the one-year mark are LTCG-eligible. This lot-level selection — matching lots to the right tax years — is the core of what an equity-comp advisor models before you start selling.

10b5-1 plans and blackout periods

If you are an officer, director, or other insider subject to trading blackout windows, a 10b5-1 trading plan lets you schedule future sales in advance — before you come into possession of material non-public information. Under the SEC's 2023 amendments,³ insider plans require a cooling-off period (90 days or the next earnings release, whichever is later) before the first sale executes. Once the plan is in place, sales execute automatically according to the schedule, eliminating the need to make sell-or-hold decisions during open windows. A fee-only advisor helps set the per-period amounts and lot selection before you submit the plan to your company's stock plan administrator.

What concentration target to use

There is no universal answer. Common benchmarks: most financial planners suggest below 20–25% for households near or in retirement; 30–40% is defensible for early-career employees with high earned income who can absorb downside risk. The more important goal is to have a written plan with specific amounts and dates — one that turns an emotionally charged quarterly decision into an automated process.

For SpaceX employees facing the post-IPO lockup: see the SpaceX equity guide. For Figma employees managing a recently-expired lockup: see Figma. For the IPO RSU tax gap from the settlement itself: see the RSU settlement tax estimator.

Turn this estimate into a lot-level plan

This calculator models equal annual installments with a flat basis ratio and constant stock price. A real glidepath accounts for your specific lots and vest dates, AMT credit carryforwards that offset future regular tax, estimated quarterly payment amounts, multi-state allocation if you moved states, and whether your company allows 10b5-1 plan automation. Get matched with a fee-only fiduciary who builds these plans for a living — free, no obligation.