Fundamentals &amp; laws

How RSUs work

An RSU is a promise of shares once you vest. That one fact, the gap between the promise and the shares, decides when you owe tax, what you own, and what you walk away with if you leave.

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

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Restricted stock awards (RSAs): the complete guide

An RSA is real stock you own at grant, on a vesting schedule, common at the earliest startups. That ownership from day one is what makes the 83(b) election possible, why founders reverse-vest, and what decides who keeps shares when someone leaves.

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.

Checklist Start here

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 work

Incentive stock options can turn your entire gain into long-term capital gains, no ordinary income at all. The path is narrow, every step has a deadline, and this is the whole map from grant to sale.

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.

Deep dive Start here

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 work: the complete guide

Non-qualified stock options are the plain option: a fixed price to buy, ordinary income at exercise, capital gains after. This is the whole story, from the 409A that sets your strike to the day you exercise and what it costs.

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

How an ESPP works: the complete guide

An employee stock purchase plan lets you buy company stock at a discount, often with a lookback that quietly doubles the deal. For most people who have one, it is the best return available at work, and this is the whole story of how it runs.

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

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How SARs and phantom stock work

SARs and phantom stock pay you cash that tracks the share price without making you buy a single share. Both feel like equity right up until the tax bill, which looks nothing like equity.

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

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What makes stock qualify as QSBS

QSBS is not a label you choose at sale. It is a stack of conditions your stock had to meet the day it was issued: the right entity, a small-enough company, original issuance straight from the company, a qualifying business, and a long enough hold.