Plan your Decagon NSO exercise
Calculator · free · no signup · pre-IPODecagon 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 Jul 31, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$105,253
Hold 1 yr wins by $59,345 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $76,850 |
| Federal | |
| State | |
| Medicare | −$1,114 |
| Additional Medicare | −$692 |
| Market gain over 1 yr at 10.0% | $4,283 |
| LTCG on diversified gain (fed + state + NIIT) | −$1,203 |
| Net at year 1 | $45,908 |
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) | −$24,397 |
| Net at year 1 | $105,253 |
Sold 3,312 shares at exercise to cover strike + tax; 1,688 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 →Related calculators: Stock Concentration Calculator · Multi-Year ISO Exercise Schedule Calculator
About Decagon
Decagon is a privately held AI company, incorporated in California and headquartered in San Francisco, CA.
Last reported secondary-market price: $25.37 per share (as of 2026-07-31). Your own 409A may differ.
$4.5B Series D.
Equity grants at Decagon typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Decagon AI, Inc. is an American artificial intelligence company that develops conversational AI agents for customer service. The company is headquartered in San Francisco, California with additional offices in New York City and London.
Source: Wikipedia (CC BY-SA 4.0)
Decagon builds autonomous AI agents that handle enterprise customer support across voice, chat, email, and SMS, counting Eventbrite, Substack, Rippling, Bilt, Webflow, Duolingo, Chime, and Oura among its customers, with deflection rates averaging near 70 percent. Jesse Zhang and Ashwin Sreenivas founded the San Francisco company in 2023. Andreessen Horowitz and Accel led a $35M Series A in 2024, followed by a $65M round and a $131M Series C at a $1.5B valuation in June 2025. A $250M Series D in January 2026 tripled the valuation to $4.5B.
Sources: decagon.ai · decagon.ai · businesswire.com
Equity comp at Decagon
- In March 2026, Decagon completed its first tender offer (a company-organized window where employees can sell some vested shares to outside buyers) at a $4.5 billion valuation. The offer was co-led by Series D investors including Coatue Management, Index Ventures, and Andreessen Horowitz, and was open to Decagon's 300-plus employees. The company's valuation tripled from $1.5 billion in June 2025 to $4.5 billion by January 2026, and the tender marked the first opportunity for early employees to convert some equity to cash.
- Recent share-sale events (industry term: tender offers):
- Mar 2026: $4.5B implied valuation, led by Coatue Management · decagon.ai
Sources: decagon.ai · techcrunch.com
Researched 2026-05-07.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Decagon.
Decagon 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 Decagon's last reported price of $25.37, exercising 5,000 NSOs with a $7.61 strike creates a $88,800 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $23,976 and $39,960 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 Decagon tools → · Use the generic NSO Exercise Calculator for any company.
Decagon equity questions
- How is a Decagon 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 Decagon grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Decagon grant ISOs, NSOs, or RSUs?
- Equity compensation at Decagon 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 Decagon 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 Decagon 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 Decagon equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.