Plan your Poolside NSO exercise
Calculator · free · no signup · pre-IPOPoolside is pre-IPO. Plan your NSO exercise tax (federal, state, FICA) at any expected valuation.
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Your grant
Seeded from secondary-market data, as of Sep 6, 2026
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$84,195
Hold 1 yr wins by $55,080 over Sell + invest.
Estimates only. Not financial advice.
Sell + invest
| Bargain element (sale − strike) | $47,950 |
| Federal | |
| State | |
| Medicare | −$695 |
| Additional Medicare | −$432 |
| Market gain over 1 yr at 10.0% | $2,716 |
| LTCG on diversified gain (fed + state + NIIT) | −$763 |
| Net at year 1 | $29,115 |
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) | −$22,290 |
| Net at year 1 | $84,195 |
Sold 3,613 shares at exercise to cover strike + tax; 1,387 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 Poolside
Poolside is a privately held AI company, incorporated in Delaware and headquartered in San Francisco, CA.
Last reported secondary-market price: $19.59 per share (as of 2026-09-06). Your own 409A may differ.
AI for code.
Equity grants at Poolside typically include incentive stock options (ISOs) and non-qualified stock options (NSOs).
Jason Warner, former CTO of GitHub, and Eiso Kant, a serial dev-tools entrepreneur, founded Poolside in April 2023. The company trains foundation models exclusively for software engineering tasks, using a method called Reinforcement Learning from Code Execution Feedback (RLCEF), which grades model outputs by actually running the generated code rather than relying on human labels. Poolside raised $500 million in an October 2024 Series B co-led by Bain Capital Ventures, with NVIDIA and DST Global participating. In October 2025 NVIDIA committed up to $1 billion in additional investment, lifting the valuation to $12 billion.
Sources: en.wikipedia.org · techcrunch.com
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Poolside.
Poolside 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 Poolside's last reported price of $19.59, exercising 5,000 NSOs with a $5.88 strike creates a $68,550 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $18,509 and $30,848 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 Poolside tools → · Use the generic NSO Exercise Calculator for any company.
Poolside equity questions
- How is a Poolside 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 Poolside grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Poolside grant ISOs, NSOs, or RSUs?
- Equity compensation at Poolside 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 Poolside 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 Poolside 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 Poolside equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.