Plan your OpenAI NSO exercise
Calculator · free · no signup · pre-IPOOpenAI 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 8, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$1,866,391
Sell + invest wins by $1,684,089 over Hold 1 yr.
Estimates only. Not financial advice.
Sell + invest
Best payout| Bargain element (sale − strike) | $3,617,700 |
| Federal | |
| State | |
| Medicare | −$52,457 |
| Additional Medicare | −$32,559 |
| Market gain over 1 yr at 10.0% | $174,122 |
| LTCG on diversified gain (fed + state + NIIT) | −$48,955 |
| Net at year 1 | $1,866,391 |
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
| Sale proceeds (year 1) | |
| LTCG tax (federal + state + NIIT) | $0 |
| Net at year 1 | $182,302 |
Sold 2,626 shares at exercise to cover strike + tax; 2,374 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 OpenAI
OpenAI is a privately held AI company, incorporated in Delaware and headquartered in San Francisco, CA.
Last reported secondary-market price: $733.54 per share (as of 2026-06-08). Your own 409A may differ.
~$500B+; 2026 IPO rumored.
Equity grants at OpenAI typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
OpenAI is an American artificial intelligence (AI) research organization headquartered in San Francisco, consisting of OpenAI Group PBC, a for-profit public benefit corporation (PBC), partially controlled by OpenAI Foundation, a nonprofit. OpenAI developed the generative pre-trained transformer (GPT) family of large language models, the DALL-E series of text-to-image models, and the Sora series of text-to-video models, which have influenced industry research and commercial applications. Its release of ChatGPT in November 2022 has been credited with catalyzing the AI boom, and widespread interest in generative AI.
Source: Wikipedia (CC BY-SA 4.0)
Founded 2015 by Sam Altman, Elon Musk (departed 2018), Ilya Sutskever, Greg Brockman and others as a non-profit AI lab, the San Francisco company spun up a capped-profit arm in 2019 and completed its restructure into OpenAI Group PBC in October 2025, with the OpenAI Foundation retaining a 26% stake. Products span GPT-5 and GPT-5.5, o-series reasoning models, ChatGPT consumer and Enterprise, the API, DALL-E, the now-discontinued Sora video generator, and Codex agents. Recent milestones: Altman's five-day ouster in November 2023, Sutskever and Mira Murati exits in 2024, and a $122B March 2026 round co-led by SoftBank, Amazon, and Nvidia at an $852B valuation. Monthly revenue runs about $2B.
Sources: en.wikipedia.org · bloomberg.com · openai.com
Equity comp at OpenAI
- OpenAI does not grant traditional stock options or RSUs. Instead, employees get Profit Participation Units (PPUs), a custom contract OpenAI created for itself. A PPU is a right to a share of OpenAI's future profits, with the total cap on what OpenAI can pay out across all partners set at $250 billion. Because PPUs are not stock and not options, the standard tax math (AMT for ISOs, ordinary-income on RSU vest) does not apply. The calculator on this page is best treated as a rough illustration until OpenAI converts equity to ordinary stock for an eventual IPO.
Sources: openai.com · theinformation.com
Researched 2026-05-06.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by OpenAI.
OpenAI 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 OpenAI's last reported price of $733.54, exercising 5,000 NSOs with a $220.06 strike creates a $2,567,400 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $693,198 and $1,155,330 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 OpenAI tools → · Use the generic NSO Exercise Calculator for any company.
OpenAI equity questions
- How is a OpenAI 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 OpenAI grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does OpenAI grant ISOs, NSOs, or RSUs?
- Equity compensation at OpenAI 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 OpenAI 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 OpenAI 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 OpenAI equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.