Each scheme behaves differently. RSU and NSO hit at ordinary income on vest or exercise; ESPP timing matters; long-term capital gains rates apply only if held 1+ year.
Effective: 29% on $121,000 proceeds
RSUs are ordinary income at vest, taxed at full federal + state + FICA. After that, hold for LTCG on appreciation (1+ year). Common practice: sell at vest to avoid concentration risk, since the W-2 income is unavoidable.
Federal marginal rates from 2024 brackets (2025 is close). LTCG: 0% / 15% / 20% federal plus 3.8% NIIT above $200k single / $250k MFJ, plus state. Short-term gains (held < 1 year) taxed at ordinary rates. NSO exercise creates a cash-flow obligation in the exercise year.
Worth runs each grant against your salary, state and capital-gains position to surface the net keep. Join the waitlist.
Almost always. NSO exercise generates an ordinary-income tax bill that's due in the year of exercise regardless of when you sell. Selling at exercise covers the bill, removes single-stock risk, and only loses the LTCG benefit on subsequent appreciation. Hold only if you have strong conviction on the stock.
Qualified saves the difference between your ordinary rate (say 32%) and the LTCG rate (15% federal) on the gain above the discount. On a $50k purchase with 15% discount and a 50% gain, qualified saves several thousand dollars over disqualified. Worth holding unless concentration risk is acute.
It doesn't really, the 0% LTCG bracket extends to $48,350 single / $96,700 MFJ, then 15% applies until $518,900 single / $583,750 MFJ, then 20%. The 5-point jumps in this calc are the bracket-edge effects modelled at the top-marginal level.