Plan your Writer NSO exercise
Calculator · free · no signup · pre-IPOWriter is pre-IPO. Plan your NSO exercise tax (federal, state, FICA) at any expected valuation.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Seeded from secondary-market data, as of Jun 7, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$127,313
Hold 1 yr wins by $53,928 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $124,900 |
| Federal | |
| State | |
| Medicare | −$1,811 |
| Additional Medicare | −$1,124 |
| Market gain over 1 yr at 10.0% | $6,846 |
| LTCG on diversified gain (fed + state + NIIT) | −$1,924 |
| Net at year 1 | $73,385 |
Sell every share immediately; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Exercise + hold 1 yr
Best payout| Sale proceeds (year 1) | |
| LTCG tax (federal + state + NIIT) | −$23,000 |
| Net at year 1 | $127,313 |
Sold 3,043 shares at exercise to cover strike + tax; 1,957 shares held 1 yr for LTCG.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're exercising as a current employee.
Both columns are stated in year-1 dollars: sell-now proceeds compound at the market return and pay LTCG on the gain at year 1; any cash paid out of pocket on the hold side carries the same opportunity cost.
Net at year N — by hold period
Estimates only. Excludes AMT (NSOs do not trigger AMT), state-AMT, multi-state moves, and disqualifying-disposition edge cases. Not financial advice.
You calculated one NSO decision. The beta plans NSOs alongside RSUs and ISOs in a single multi-year tax plan.
Request beta access →About Writer
Writer is a privately held AI company, headquartered in San Francisco, CA.
Last reported secondary-market price: $34.98 per share (as of 2026-06-07). Your own 409A may differ.
Enterprise AI platform.
Equity grants at Writer typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
May Habib and Waseem Alshikh, who previously co-founded the localization SaaS Qordoba together, launched Writer in San Francisco in 2020 to build an enterprise AI platform for complex, multi-step agentic workflows rather than single-turn text generation. Writer sells to regulated industries (legal, finance, and healthcare), integrating with existing data systems and enforcing compliance guardrails. The company raised $200 million in a Series C at a $1.9 billion valuation in November 2024, co-led by Premji Invest, Radical Ventures, and ICONIQ Growth, bringing total disclosed funding to $369 million.
Sources: techcrunch.com · writer.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Writer.
Writer NSO exercise creates ordinary income on the bargain element (federal, state, and FICA) at the price on the day you exercise. The calculator works at any valuation, so you can model your exercise cost at the current 409A FMV, an expected IPO price, or post-IPO scenarios.
Example: at Writer's last reported price of $34.98, exercising 5,000 NSOs with a $10.49 strike creates a $122,450 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $33,061 and $55,102 depending on your bracket and state. The calculator above computes the exact figure for your situation and compares selling now vs. holding through the long-term capital-gains threshold.
All Writer tools → · Use the generic NSO Exercise Calculator for any company.
Writer equity questions
- How is a Writer NSO exercise taxed?
- Exercising a non-qualified stock option (NSO) creates ordinary income on the bargain element (the price on the day you exercise minus your strike), subject to federal income tax, state income tax, and FICA. The calculator above computes that tax for your Writer grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Writer grant ISOs, NSOs, or RSUs?
- Equity compensation at Writer typically takes the form of incentive stock options (ISOs) and non-qualified stock options (NSOs). Incentive stock options can trigger the alternative minimum tax (AMT) when you exercise.
- Are Writer shares eligible for QSBS?
- They might be. Qualified small business stock (QSBS) under Internal Revenue Code Section 1202 can exclude federal tax on much of the gain when shares were acquired at original issuance from a C-corporation while its gross assets were under $50 million, and held at least five years. Whether your Writer shares qualify turns on when you acquired them and the company's asset size at that time.
One piece of the puzzle.
OptionsAhoy plans your Writer equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.