Plan your Zipline NSO exercise
Calculator · free · no signup · pre-IPOZipline 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
$149,326
Hold 1 yr wins by $34,731 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $197,450 |
| Federal | |
| State | |
| Medicare | −$2,863 |
| Additional Medicare | −$1,777 |
| Market gain over 1 yr at 10.0% | $10,691 |
| LTCG on diversified gain (fed + state + NIIT) | −$3,004 |
| Net at year 1 | $114,595 |
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) | −$16,578 |
| Net at year 1 | $149,326 |
Sold 2,840 shares at exercise to cover strike + tax; 2,160 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 Zipline
Zipline is a privately held Hardware company, incorporated in Delaware and headquartered in South San Francisco, CA.
Last reported secondary-market price: $49.49 per share (as of 2026-06-16). Your own 409A may differ.
Drone logistics.
Equity grants at Zipline typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Zipline International Inc. is an American company that designs, manufactures, and operates delivery drones, with distribution centers in the United States, Rwanda, Ghana, Japan, Nigeria, Côte d'Ivoire, and Kenya. Its drones deliver blood products, vaccines, and medical supplies, and the company also makes deliveries on behalf of food and retail businesses, including partnerships with Walmart and Chipotle Mexican Grill. As of January 2026, Zipline's drones have completed more than two million commercial deliveries and flown over 120 million miles.
Source: Wikipedia (CC BY-SA 4.0)
Founded in 2014 by Keller Rinaudo Cliffton, Keenan Wyrobek, William Hetzler, and Ryan Oksenhorn, Zipline operates autonomous delivery drones from South San Francisco. Platform 1, a 44-pound fixed-wing aircraft, pioneered medical supply runs across Rwanda, Ghana, Nigeria, Kenya, and Cote d'Ivoire. Platform 2, launched April 2025, is a hybrid VTOL that lowers packages via a tethered droid with one-meter precision, now serving Walmart in Arkansas and the Dallas-Fort Worth metroplex plus a Cleveland Clinic medication pilot. A January 2026 round led by Valor Equity Partners added $600 million at a $7.6 billion valuation, with over 2 million cumulative deliveries logged.
Sources: en.wikipedia.org · techcrunch.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Zipline.
Zipline 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 Zipline's last reported price of $49.49, exercising 5,000 NSOs with a $14.85 strike creates a $173,200 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $46,764 and $77,940 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 Zipline tools → · Use the generic NSO Exercise Calculator for any company.
Zipline equity questions
- How is a Zipline 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 Zipline grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Zipline grant ISOs, NSOs, or RSUs?
- Equity compensation at Zipline 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 Zipline 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 Zipline 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 Zipline equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.