Plan your Decagon ISO exercise
Calculator · free · no signup · pre-IPODecagon is pre-IPO. Plan your AMT impact at any valuation: current 409A, expected IPO price, or post-IPO scenarios.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Tax inputs
Grant timeline
Net final value at year 3 sale — optimized plan
$242,783
After-tax dollars at end of year 3, net of all federal + state taxes through the sale.
This year: exercise 2,640 shares (of 10,000 total).
= gross gain at sale − federal + state LTCG − AMT premium above baseline regular tax (time-valued)
AMT premium for exercising: $90,254 (on top of $228,434 regular tax across the horizon)
Optimized plan keeps $57,102 more than lump-sum, $796 more than even split.
Federal AMT crossover this year: 1,271 shares ($57,238 bargain element). Above that, each additional share this year adds federal AMT.
Estimates only. Not financial advice.
Net final value by year
Running tally: NTV from shares exercised through year y, minus AMT premium paid through year y. The last year matches the plan's headline NTV. Hover a year for plan totals.
Optimized exercise schedule
You pay the higher of Regular tax and Tentative AMT per jurisdiction, then subtract Credit recovered. The result is Net tax. Hover any number for the bracket-by-bracket breakdown.
| 1 | 2,640 | |||
| 2 | 2,567 | |||
| 3 | 4,793 |
Federal AMT credit
Earned
$80,681
Recovered
$0
Remaining
$80,681
The AMT credit only recovers in years where regular tax exceeds AMT — typically a year with no ISO exercise. Every year in this schedule has bargain element, so AMT exceeds regular tax in every year and the credit carries forward untouched. Try a longer horizon or fewer total shares to introduce a recovery year.
Plan comparison
Net value at the end of your hold horizon.
Lump-sum
All in Year 1
$185,681
−$57,102
Even split
Equal shares each year
$241,987
−$796
Optimized
Tax-aware schedule
$242,783
Highest
Estimates only. Excludes disqualifying dispositions, NSOs, multi-state moves, and AMT preferences other than ISO bargain elements. Long-term capital gains tax assumes a qualifying disposition (ISO held ≥1 yr from exercise and ≥2 yr from grant); state LTCG follows ordinary brackets except where the state grants preferential treatment (HI, ND, SC, WI, AR, NM) or has a dedicated LTCG-only tax (WA). Assumes you are within the $100K ISO limit (any portion of an annual ISO grant whose FMV at grant exceeds $100K is treated as NSO from the start, §422(d)). State AMT figures are 2025 (next-year values published in late 2026). Not financial advice.
QSBS note. If your shares qualify (typically pre-IPO C-corp grants held 5+ years), a federal rule lets you exclude up to $10M of gain on a future sale from federal tax. That single rule shifts exercise-timing math more than AMT does. (This is §1202 “qualified small-business stock”.) Modeled in beta, not here.
You optimized one grant in isolation. The beta optimizes ISOs alongside your RSUs, NSOs, and stock in one plan.
Request beta access →About Decagon
Decagon is a privately held AI company, incorporated in California and headquartered in San Francisco, CA.
$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)
Founded in 2023 by Jesse Zhang and Ashwin Sreenivas, Decagon builds autonomous AI agents that handle enterprise customer support across voice, chat, email, and SMS. The San Francisco company counts Eventbrite, Substack, Rippling, Bilt, Webflow, Duolingo, Chime, and Oura among its customers, with deflection rates averaging near 70 percent. 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.
The calculator works at any Decagon valuation: enter your strike, the current 409A FMV, an expected IPO price, or anywhere in between. AMT is triggered on the bargain element (FMV minus strike) when you exercise; the calculator models federal AMT, state AMT, and the multi-year credit-recovery path.
All Decagon tools → · Use the generic AMT + ISO Exercise Calculator for any company.
Decagon equity questions
- How much alternative minimum tax (AMT) will I owe exercising Decagon ISOs?
- Exercising incentive stock options (ISOs) does not create regular income tax, but the bargain element (the fair market value at exercise minus your strike price) counts toward the alternative minimum tax (AMT). The amount depends on the bargain element, your other income, your filing status, and your state. The calculator above models federal and state AMT, the AMT crossover point, and how the credit recovers in later years for your exact Decagon figures.
- 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.