Plan your Gusto NSO exercise
Calculator · free · no signup · pre-IPOGusto 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 9, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$93,975
Hold 1 yr wins by $58,075 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $59,350 |
| Federal | |
| State | |
| Medicare | −$861 |
| Additional Medicare | −$534 |
| Market gain over 1 yr at 10.0% | $3,349 |
| LTCG on diversified gain (fed + state + NIIT) | −$941 |
| Net at year 1 | $35,900 |
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) | −$23,638 |
| Net at year 1 | $93,975 |
Sold 3,469 shares at exercise to cover strike + tax; 1,531 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 Gusto
Gusto is a privately held Cloud/SaaS company, incorporated in Delaware and headquartered in San Francisco, CA.
Last reported secondary-market price: $21.87 per share (as of 2026-06-09). Your own 409A may differ.
SMB payroll/HR.
Equity grants at Gusto typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Gusto, Inc. is a company that develops payroll, benefits, and human resource management software for businesses based in the United States.
Source: Wikipedia (CC BY-SA 4.0)
Joshua Reeves, Tomer London, and Edward Kim launched Gusto, originally ZenPayroll, in December 2012 to automate payroll, benefits, and HR administration for small businesses. The platform handles federal, state, and local tax filings automatically and has expanded to cover health insurance brokerage, workers' compensation, and time tracking. Gusto serves more than 400,000 businesses and generated $975 million in revenue in 2025, up 30% year over year. A June 2025 tender offer set its valuation at $9.3 billion. The company acquired retirement plan provider Guideline for roughly $600 million in November 2025.
Sources: en.wikipedia.org · sacra.com
Equity comp at Gusto
- Gusto has run at least three employee tender offers (company-organized windows where employees can sell some vested shares to outside buyers) since founding. The most recent confirmed offer closed in June 2025, raising over $200 million at a $9.3 billion valuation led by Ontario Teachers Pension Plan. It was open to current and former employees with at least two years of tenure. An earlier offer occurred in 2021 alongside the Series E round at roughly $9.5 billion valuation. Fortune reporting described the 2025 event as the third such offer, suggesting a third earlier liquidity event not well documented publicly.
- Recent share-sale events (industry term: tender offers):
- Jun 2025: $9.3B implied valuation, led by Ontario Teachers Pension Plan (Teachers Venture Growth) · fortune.com
Sources: fortune.com · finance.yahoo.com
Researched 2026-05-10.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Gusto.
Gusto 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 Gusto's last reported price of $21.87, exercising 5,000 NSOs with a $6.56 strike creates a $76,550 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $20,669 and $34,448 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 Gusto tools → · Use the generic NSO Exercise Calculator for any company.
Gusto equity questions
- How is a Gusto 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 Gusto grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Gusto grant ISOs, NSOs, or RSUs?
- Equity compensation at Gusto 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 Gusto 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 Gusto 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 Gusto equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.