RSUs, ISOs, ESPP shares, 83(b) elections, and the AMT math behind stock that gets taxed the moment it vests or you exercise.
Selling qualified small business stock before the five-year mark normally means paying full freight on the gain. IRC §1045 defers all of it if you buy replacement QSBS within 60 days, and on a $6,050,000 exit that is $1,428,000 that does not come due.
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IRC §83(i) lets a qualified employee defer federal income tax on vested private company stock for up to 5 years. The 80% employee rule and a mandatory escrow keep most plans out, and the deferral locks in the vest-date value even if the shares fall to a quarter of it.
Read postSection 422(a)(2) gives you three months after employment ends before an ISO exercise is taxed as an NSO. On a $200,000 spread in 2026 that swap costs about $27,000 of extra tax. How the window works, and the disability, death, and extended-window exceptions.
Read postIncentive stock options only get ISO treatment up to $100,000 of grant-date value that first becomes exercisable in a calendar year. Above that line the excess is a nonqualified option, taxed as wages the moment you exercise, and an acquisition can push a whole grant over it.
Read postThe AMT you pay to exercise and hold incentive stock options comes back. It is a §53 minimum tax credit you recover on Form 8801, faster if you sell the shares, and there is one case where it barely moves.
Read postThe IRS taxed your RSUs as wages at the vest-day price. The round trip back down is a capital loss you deduct at $3,000 a year, and a layoff usually means selling at the bottom. The asymmetry is fixable, but only in advance.
Read postCompany stock is down and the losses look harvestable, but an RSU holder has a problem no index-fund investor has: the next vest is an acquisition whether you want it or not, and on a monthly schedule it always lands inside the 30-day window.
Read postThe IRS opened electronic filing of Form 15620 in July 2025, so an 83(b) election is now a portal session instead of a certified-mail ritual. The 30-day deadline did not move, the copy to your company is still required, and a few quirks of the online form can still burn founders.
Read postYour RSUs vested, the company sold shares to cover the tax, and you still got a five-figure bill in April. The reason is the flat 22% supplemental wage withholding rate. If your bracket is 32% or 35%, that rate is built to come up short. Here is the 2026 math and the two ways to close the gap before you owe a penalty.
Read postOBBBA reset the AMT exemption phaseout thresholds to $500,000 and $1,000,000 for 2026 and doubled the phaseout rate to 50%. The number of incentive stock options you can exercise before the alternative minimum tax kicks in just shrank, and the marginal rate above the threshold is now an effective 42%. Here is the new crossover math.
Read postBrokers do not include the bargain element from an ESPP disqualifying disposition in the cost basis reported on Form 1099-B. Here is how the ESPP disqualifying disposition cost basis problem creates double tax, the Form 8949 code B adjustment that fixes it, and how to claim a refund before the §6511 window closes.
Read postThe One Big Beautiful Bill Act rewrote three of Section 1202's most important numbers: the holding period, the per-issuer cap, and the gross-assets test. Here's what the new QSBS math means for founders, early employees, and anyone weighing a C corporation conversion.
Read postISOs, RSUs, ESPP shares, and 83(b) elections create tax the moment they vest or exercise, and the AMT bill can land months later. We model the spread, time the sales, and file the elections on the clock, so the windfall is not eaten by a surprise in April.