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Fundamentals & laws
RSUs
How RSUs are taxed
RSUs are taxed as ordinary income the day they vest, then as capital gains on anything they earn after that. The trap is the gap between what your employer withholds and what you actually owe, and on a big year it pulls in surtaxes and quarterly payments too.
How to read your W-2 and 1099-B for RSUs
The vesting income already sits in your W-2. The basis column on your 1099-B is the one you have to correct yourself, or the same dollars get taxed twice. Here is every number, where it lives, and a full vest worked start to finish.
Restricted stock
How restricted stock is taxed (and how 83(b) flips it)
Restricted stock is taxed as ordinary income as it vests, unless you file an 83(b) and flip the whole thing to capital gains. That one form is the difference between a tax bill on tomorrow's value and one on today's, and it quietly starts the clocks that decide your rate years later.
How to file an 83(b) election, step by step
The letter, the 30-day clock, the line-by-line fields, and the proof you keep, in one checklist. Filing 83(b) is simple, but it is unforgiving, so the order of operations matters.
ISOs
How ISOs are taxed at exercise and sale
ISOs skip ordinary tax at exercise, but the disposition decides everything: clear both holding clocks and the whole gain is long-term capital gains, miss either and the spread becomes ordinary income.
ISOs and the AMT: the complete guide
Exercising and holding ISOs can hand you a cash tax bill on a gain you never sold, and this is the whole story of how that happens and how to plan around it.
Form 3921 and Form 6251 for ISOs
One form your employer mails you, one form where the AMT shows up, and one form where the sale gets reported three different ways. Get them aligned and the ISO surprise loses its power.
NSOs
How NSOs are taxed: the bargain element and everything after
The spread between the stock price and your strike at exercise is ordinary income, taxed like salary that year. Then the shares are just stock. This is the whole NSO tax picture: the spread, the payroll surtaxes, the withholding gap, your real basis, and the capital gain after.
NSO exercise strategy: when to exercise, hold or sell, and the moves around it
The one lever an NSO hands you is the calendar. This is the whole playbook: when to exercise, whether to hold or sell, how to spread it, how to fund the tax, and how to give the shares away.
NSO traps: the double-counted basis, the cash bills, and the deadlines that kill grants
The expensive NSO mistakes are quiet ones. The double-counted 1099-B basis taxes you twice, under-withholding ambushes you in April, illiquid stock owes cash you can't raise, and two deadlines erase winning options. Here is all of it.
Reporting NSOs: your W-2, your 1099-B, and the basis fix
The spread lands in your wages on the W-2, the sale shows up separately on the 1099-B, and the basis is the link between them. Read them as one story, fix the basis on Form 8949, and you pay tax once instead of twice.
ESPPs
ESPP taxes: qualifying vs disqualifying dispositions, the complete guide
How long you hold ESPP shares changes how the discount is taxed, splitting your gain between salary rates and the lower capital-gains rate. This is the whole story: the two clocks, the two formulas, the basis trap that taxes you twice, and the state and AMT wrinkles most people miss.
ESPP reporting: Form 3922, Form 8949, and the basis fix
The form your employer sends, the forms you file, and the one adjustment that keeps you from paying tax on your discount twice. A full walkthrough with a worked example and a pre-sale checklist.
Hybrids & more
Secondary sales and tender offers for private shares
How employees turn private stock into cash before an IPO, what the price really means, what it taxes, and how much you should actually sell.
How SARs and phantom stock are taxed
Cash-settled equity looks like stock and gets taxed like salary. The whole payout is ordinary income the day it lands, there is no capital gains door, and the only real lever you have is timing.
QSBS
QSBS (Section 1202): the complete guide
Qualified small business stock can erase the federal tax on a startup-stock sale, sometimes the whole thing. This is the full story: which rules apply to your shares, how the exclusion is sized, the holding clock, and the per-issuer cap that decides how much you actually shelter.
How people accidentally blow their QSBS
Most QSBS gets lost by accident, not by bad luck. A redemption, an early sale, the wrong entity, a secondary purchase, or missing records can quietly kill a break worth more than the mistake ever felt at the time.
Reporting a QSBS exclusion on your return
The QSBS break is not automatic on your tax return. You report the full sale, then back the exclusion out with the right code, or the gain stays taxed.