Stripe RSU sell-vs-hold
Calculator · free · no signup · pre-IPOStripe is pre-IPO. After IPO, RSUs vest as ordinary income. Should you sell at vest or hold through the 12-month LTCG cliff?
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your vest
Seeded from secondary-market data, as of Jun 16, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1 yr
$43,140
Sell + invest wins by $969 over Hold 1 yr.
Estimates only. Not financial advice.
Heads-up: under-withholding. Your employer withholds federal tax at the IRS supplemental rate (22.0% on this vest, ≈ $15,842). Your marginal federal rate on this vest is 32.5%, owing $23,375. Expect to settle the $7,533 gap at tax time.
The hidden purchase
Tax was paid at vest either way. Holding is mathematically equivalent to taking $40,246 in after-tax cash and buying $40,246 of this stock today.
Most diversification frameworks would advise against a purchase that size in a single name; the right answer depends on your conviction in this stock. Holding past one year converts the gain to LTCG.
Sell + invest
Best payout| Vest value (shares × price) | $72,010 |
| Federal | |
| State | |
| Medicare | −$1,044 |
| Additional Medicare | −$648 |
| Market gain over 1 yr at 10.0% | $4,025 |
| Cap-gain tax on diversified gain — LTCG (federal + state + NIIT) | −$1,131 |
| Net at year 1 yr | $43,140 |
Sell every share at vest; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Hold 1 yr
| Vest value (shares × price) | $72,010 |
| Vest tax (federal + state + FICA) | |
| Single-stock gain at sale (after 20% drag) | $2,677 |
| Cap-gain tax on stock — LTCG (federal + state + NIIT) | −$752 |
| Net at year 1 yr | $42,171 |
Sold 441 shares to cover vest tax (net-settled); kept 559 shares 1 yr to qualify for long-term capital gains.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're still employed at vest.
Both columns are stated in year-1 yr dollars. The sell side compounds at the market return; the hold side compounds at your single-stock expected return after a 20% volatility drag.
Estimates only. Assumes net-settled (sell-to-cover) vesting; double-trigger and pre-IPO RSUs are out of scope. Excludes multi-state moves, AMT interactions on other equity, and 83(b) elections. Not financial advice.
You evaluated one RSU vest. The beta plans every vest of every grant across years, with concentration and AMT in the loop.
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.
Most pre-IPO companies grant ISOs or NSOs rather than RSUs. If you hold Stripe RSUs, this calculator works at any valuation.
Example: 500 Stripe RSUs vesting at $72.01 per share is $36,005 of ordinary income on vest day. After roughly 32% combined federal + state + FICA (~$11,522), the post-tax share value is ~$24,483. Holding 12 months for long-term capital-gains treatment then only matters for the price change between vest and sale; the ordinary income at vest is already locked in. The calculator runs both paths through the same after-tax math.
All Stripe tools → · Use the generic RSU Sell-vs-Hold Calculator for any company.
Stripe equity questions
- Should I sell or hold my Stripe RSUs at vest?
- Stripe restricted stock units (RSUs) are taxed as ordinary income on their value at vest whether or not you sell. The only open decision is what to do with the shares afterward: sell at vest and reinvest, or hold past twelve months for long-term capital-gains treatment on any further gain. The calculator above runs both paths through the same after-tax math so you can compare them directly.
- 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.
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