Plan your Stripe NSO exercise
Calculator · free · no signup · pre-IPOStripe 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 16, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$177,091
Sell + invest wins by $3,977 over Hold 1 yr.
Estimates only. Not financial advice.
Sell + invest
Best payout| Bargain element (sale − strike) | $310,050 |
| Federal | |
| State | |
| Medicare | −$4,496 |
| Additional Medicare | −$2,790 |
| Market gain over 1 yr at 10.0% | $16,521 |
| LTCG on diversified gain (fed + state + NIIT) | −$4,642 |
| Net at year 1 | $177,091 |
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) | −$3,088 |
| Net at year 1 | $173,113 |
Sold 2,706 shares at exercise to cover strike + tax; 2,294 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 Stripe
Stripe is a privately held Fintech company, incorporated in Delaware and headquartered in South San Francisco, CA.
Last reported secondary-market price: $72.01 per share (as of 2026-06-16). Your own 409A may differ.
$95B; RSU-heavy comp.
Equity grants at Stripe typically include incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs).
Stripe, Inc. is an Irish and American multinational financial services and software as a service (SaaS) company dual-headquartered in South San Francisco, California, United States, and Dublin, Ireland. The company primarily offers payment-processing software and application programming interfaces for e-commerce websites and mobile applications.
Source: Wikipedia (CC BY-SA 4.0)
Brothers Patrick and John Collison founded Stripe in 2010 to solve a problem they had encountered themselves: accepting payments online required weeks of bank integrations and bespoke code. Stripe replaced that with a few lines of API. Today the company processes hundreds of billions of dollars in annual payments volume for millions of businesses worldwide. Its most recent primary funding round closed at $694 million in April 2024; by February 2026 an employee tender offer set its valuation at $159 billion.
Sources: en.wikipedia.org
Equity comp at Stripe
- Starting in 2022, Stripe stopped granting ISOs to new hires and switched to RSUs (restricted stock units, where you receive shares directly when they vest, taxed as ordinary income at vest). If you joined Stripe before 2022 and hold ISOs, your grant is fixed: you will not get more ISOs going forward. The AMT + ISO calculator on this page is most useful for planning when to exercise those existing grants. New hires after 2022 should use the RSU sell-vs-hold calculator instead, since they receive no ISOs.
- RSUs use double-trigger vesting. Two things must both happen before the shares are yours: (1) the normal time-based vesting completes, and (2) the company has a liquidity event (an IPO or an acquisition). Until both happen, you do not yet own the shares and you do not owe tax on them.
Sources: theinformation.com
Researched 2026-05-06.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Stripe.
Stripe 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 Stripe's last reported price of $72.01, exercising 5,000 NSOs with a $21.6 strike creates a $252,050 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $68,054 and $113,423 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 Stripe tools → · Use the generic NSO Exercise Calculator for any company.
Stripe equity questions
- How is a Stripe 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 Stripe grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Stripe grant ISOs, NSOs, or RSUs?
- Equity compensation at Stripe typically takes the form of incentive stock options (ISOs), non-qualified stock options (NSOs), and restricted stock units (RSUs). Incentive stock options can trigger the alternative minimum tax (AMT) when you exercise. Restricted stock units are taxed as ordinary income when they vest.
- Do Stripe RSUs use double-trigger vesting?
- Yes. Stripe restricted stock units (RSUs) vest only when two things both happen: the time-based schedule completes, and the company has a liquidity event such as an initial public offering (IPO) or an acquisition. Until both occur you do not own the shares and owe no tax on them.
- Are Stripe 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 Stripe 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 Stripe equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.