Plan your Perplexity NSO exercise
Calculator · free · no signup · pre-IPOPerplexity 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
$166,429
Hold 1 yr wins by $8,631 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $275,000 |
| Federal | |
| State | |
| Medicare | −$3,988 |
| Additional Medicare | −$2,475 |
| Market gain over 1 yr at 10.0% | $14,721 |
| LTCG on diversified gain (fed + state + NIIT) | −$4,137 |
| Net at year 1 | $157,798 |
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) | −$7,510 |
| Net at year 1 | $166,429 |
Sold 2,735 shares at exercise to cover strike + tax; 2,265 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 Perplexity
Perplexity is a privately held AI company, incorporated in Delaware and headquartered in San Francisco, CA.
Last reported secondary-market price: $65 per share (as of 2026-06-16). Your own 409A may differ.
$20B; AI search.
Equity grants at Perplexity typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Perplexity AI, Inc., or simply Perplexity, is an American privately held software company offering a web search engine that processes user queries and synthesizes responses. Perplexity products use large language models and incorporate real-time web search capabilities, providing responses based on current Internet content, citing sources used. Its real-time search engine is called Sonar and is based on Meta's Llama model. A free public version is available, while a paid Pro subscription offers access to more advanced language models and additional features.
Source: Wikipedia (CC BY-SA 4.0)
Founded in 2022 by Aravind Srinivas (ex-OpenAI), Denis Yarats, Johnny Ho, and Andy Konwinski, Perplexity runs an AI answer engine out of San Francisco, blending conversational search with Pro Search, Pages, and Spaces. The Comet AI browser debuted on desktop in July 2025, reached Android in November, and rolled out to iPhone on March 11, 2026, with OEM preload talks signaling a default-browser play. Valuation climbed from $14B in March 2025 to $20B in September, and reportedly $22.6B by January 2026. Apple ultimately chose Gemini over a Perplexity acquisition.
Sources: techcrunch.com · bloomberg.com · en.wikipedia.org
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Perplexity.
Perplexity 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 Perplexity's last reported price of $65, exercising 5,000 NSOs with a $19.5 strike creates a $227,500 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $61,425 and $102,375 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 Perplexity tools → · Use the generic NSO Exercise Calculator for any company.
Perplexity equity questions
- How is a Perplexity 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 Perplexity grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Perplexity grant ISOs, NSOs, or RSUs?
- Equity compensation at Perplexity 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 Perplexity 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 Perplexity 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 Perplexity equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.