Plan your Character.AI ISO exercise
Calculator · free · no signup · pre-IPOCharacter.AI 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
Seeded from secondary-market data, as of Aug 2, 2024
Tax inputs
Grant timeline
Net final value at year 3 sale — optimized plan
$338,109
After-tax dollars at end of year 3, net of all federal + state taxes through the sale.
This year: exercise 3,012 shares (of 10,000 total).
= gross gain at sale − federal + state LTCG − AMT premium above baseline regular tax (time-valued)
AMT premium for exercising: $248,079 (on top of $228,434 regular tax across the horizon)
Optimized plan keeps $38,918 more than lump-sum, $1,038 more than even split.
Federal AMT crossover this year: 689 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 | 3,012 | |||
| 2 | 2,933 | |||
| 3 | 4,055 |
Federal AMT credit
Earned
$204,433
Recovered
$0
Remaining
$204,433
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
$299,192
−$38,918
Even split
Equal shares each year
$337,071
−$1,038
Optimized
Tax-aware schedule
$338,109
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 Character.AI
Character.AI is a privately held AI company, incorporated in Delaware and headquartered in Menlo Park, CA.
Last reported secondary-market price: $88 per share (as of 2024-08-02). Your own 409A may differ.
Conversational AI.
Equity grants at Character.AI typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Character.ai is a generative AI chatbot service where users can engage in conversations with customizable characters. It was designed by the developers of Google LaMDA, Noam Shazeer and Daniel de Freitas.
Source: Wikipedia (CC BY-SA 4.0)
Noam Shazeer and Daniel De Freitas founded Character.AI in 2021 after leaving Google, where Shazeer had led the team that built the LaMDA conversational model. The company raised more than $150 million largely from a16z and reached a $1 billion valuation as consumer chatbot demand surged in 2023. In August 2024, Google paid roughly $2.7 billion for a non-exclusive license to Character.AI's technology and rehired Shazeer, De Freitas, and members of the research team into DeepMind in a deal regulators have described as a reverse acquihire. Character.AI continued as an independent company under interim CEO Dominic Perella, with most staff staying, and uses both internally-developed and third-party language models to power its consumer chatbot product.
Sources: techcrunch.com · washingtonpost.com · cnbc.com
Equity comp at Character.AI
- In August 2024, Google struck a deal to license Character.AI's technology and hired the founding team (including Noam Shazeer and Daniel De Freitas) back to Google in a transaction valued at roughly $2.7 billion. Character.AI continued as an independent company under new leadership. Employees who joined before the acquihire held equity in an entity that lost its founding team but retained its technology license; post-deal equity value depends on the standalone company's performance, not Google's stock.
Researched 2026-05-07.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Character.AI.
The calculator works at any Character.AI 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.
Example: at Character.AI's last reported price of $88, exercising 5,000 ISOs with a $26.4 strike creates a $308,000 bargain element. Above the 2026 federal AMT exemption ($88,100 single, $137,000 married joint), the 28% AMT rate adds roughly $86,240 on top of regular tax before any state AMT (CA, CO, CT, MN). The credit recovers in later years when your regular tax exceeds AMT. The calculator above runs your exact figures.
All Character.AI tools → · Use the generic AMT + ISO Exercise Calculator for any company.
Character.AI equity questions
- How much alternative minimum tax (AMT) will I owe exercising Character.AI 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 Character.AI figures.
- Does Character.AI grant ISOs, NSOs, or RSUs?
- Equity compensation at Character.AI 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 Character.AI 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 Character.AI 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 Character.AI equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.