Leaving Character.AI? Plan your 90-day ISO window
Calculator · free · no signup · pre-IPOCharacter.AI is pre-IPO. Left with vested ISOs? Model the 90-day exercise-or-forfeit decision and its AMT cost at any valuation: current 409A or an expected exit price.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Seeded from secondary-market data, as of Aug 2, 2024
Tax inputs
Grant timeline
Recommended exercise quantity
Exercise all 10,000
With 10%/yr expected growth over the 3-yr hold, every share's expected after-tax gain exceeds its marginal AMT cost. Net value: $299,122 at horizon.
Net after-tax value vs. shares exercised
Each point is the expected after-tax NPV at your hold horizon if you exercise that many shares now and let the rest expire.
Year-by-year tax breakdown
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 | 10,000 | |||
| 2 | 0 | |||
| 3 | 0 |
Federal AMT credit
Earned
$241,054
Recovered
$29,764
Remaining
$211,290
The AMT credit only recovers in years where regular tax exceeds AMT — typically a year with no ISO exercise. It carries forward indefinitely (Form 8801) and applies in any future tax year where regular tax exceeds AMT.
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 solved the exercise window. The beta plans what comes after it: the new shares, your remaining equity, hedges, and taxes in one multi-year 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.
Sources: techcrunch.com
Researched 2026-05-07.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Character.AI.
If you are leaving Character.AI with vested incentive stock options (ISOs), most stock plans give you 90 days from departure to exercise or forfeit them. The calculator works at any valuation: enter your strike and the current 409A fair market value (FMV) or an expected exit price. It computes your window deadline, the alternative minimum tax (AMT) cost of exercising in full, and the partial-exercise share count that maximizes expected after-tax value.
Example: leaving Character.AI with 5,000 vested ISOs at a $26.4 strike, with the last reported price at $88, exercising all of them inside the 90-day window puts a $308,000 bargain element into one tax year. 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). Exercising fewer shares lowers that bill at the cost of forfeiting the rest; the calculator above finds the count that maximizes expected after-tax value for your exact figures.
All Character.AI tools → · Use the generic Post-Termination ISO Exercise Calculator for any company.
Character.AI equity questions
- I left Character.AI. How long do I have to exercise my ISOs?
- Most stock plans give you 90 days from your departure date to exercise vested incentive stock options (ISOs); unexercised options are forfeited when the window closes. Tax law is slightly wider: ISO treatment requires you to have been an employee within 3 months of exercise (Internal Revenue Code Section 422(a)(2)), so options exercised under an employer-extended window are taxed as non-qualified stock options (NSOs). Check your grant agreement for Character.AI's exact terms. The calculator above computes your deadline from your departure date, the alternative minimum tax (AMT) cost of exercising, and the share count that maximizes after-tax value.
- 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.