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Sale
RSUs
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.
Case study: a full vesting year at a public company
An engineer with a large RSU year, and the tax bill nobody warned her about.
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.
Sell at vesting or hold? The complete RSU decision
Sell at vesting unless you can name a real reason to hold. This is the whole decision, start to finish: the default, how to fund the tax, when holding earns its keep, how to diversify a pile you already have, and how to give shares away without paying gains.
The RSU tax traps that hit in April, and how to dodge them
The flat rate your company withholds at vesting is almost always lower than what you owe, and that gap is just the first of the RSU traps. This is the complete field guide: the withholding gap, estimated taxes, the double-taxed 1099-B, short-term gains, blackouts, wash sales, acceleration, and the private-company bill on shares you cannot sell.
Case study: the $14,000 double-tax RSU mistake
How a wrong 1099-B basis overcharged one filer, and how the amended return fixed it.
How RSUs are taxed at an IPO
An IPO can detonate years of double-trigger RSUs into one tax year. The income stacks, the withholding falls short, and the bill arrives while the stock is still locked up.
RSU sell-or-hold after-tax calculator
Compare selling at vest against holding, after tax and after concentration risk.
Case study: holding RSUs through an IPO
Double-trigger shares all settle at once, and a six-figure tax bill lands in one quarter.
Restricted stock
Restricted stock in an acquisition
When your company gets bought, your restricted stock can cash out, convert to acquirer shares, or roll into new vesting. Which one you get, and whether your unvested shares accelerate, decides what the deal actually pays you.
A founder's restricted stock, start to exit
Follow one founder's restricted stock from incorporation to acquisition, and watch how a single form filed in week one decides what the exit actually pays. The tax fork happens at the beginning, not the end.
ISOs
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.
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.
Planning the ISO exercise year
Exercise up to the point where AMT kicks in, early in the year, then stop and repeat. The whole strategy is choosing how much spread to recognize, when to hold, and when to sell, on purpose.
Case study: exercising pre-IPO ISOs
An early employee exercised before the IPO and made an AMT bet that paid off. The lesson is in why it worked, not that it did.
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.
Case study: a disqualifying ISO sale to diversify fast
Why one founder chose ordinary income over holding a single volatile stock for the lower rate.
Case study: the AMT trap when the stock crashed
A worker owed AMT on a paper gain, then the shares fell 70%. Here is what he did next and what would have saved him.
Case study: what happens to ISOs in an acquisition or IPO
A liquidity event finally lets you sell, and that is exactly when ISO holders make their most expensive mistakes. The money showing up is not the same as the money you keep.
NSOs
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.
Case study: a large NSO exercise in one year
A director exercises $300k of spread at once, gets surprised by the bracket math, and learns the lever was the calendar all along.
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.
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.
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.
ESPPs
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.
The ESPP mistakes that quietly cost you money
From selling a few days early to paying tax twice on your discount, the ESPP punishes small oversights. Here is the full list of the traps and how to dodge each one.
Case study: two years of ESPP, two outcomes
Same plan, same employee. One year she sold at purchase. The next year she held for the tax break. Here is which one came out ahead.
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.
Is maxing out your ESPP worth it
With a real discount and a quick sale, an ESPP is often the highest-return benefit you have. This is the whole playbook: whether to max it, how to fund it, when to sell, and the rare case for holding.
ESPP cost basis adjustment calculator
Work out your corrected basis so you do not pay tax on the discount twice.
Case study: catching the ESPP double-tax before filing
One filer almost paid tax twice on the same discount. The fix was one number on one form, and it saved him about $4,000.
Keeping ESPP shares from concentrating your portfolio
The discount is real, but every share you keep stacks more of your net worth on the one stock that already signs your paycheck. Here is how to take the deal without taking the bet.
ESPP return calculator
See the annualized return on your ESPP after the discount, lookback, and tax.
Case study: holding ESPP shares straight into a crash
He held for the lower tax rate and watched the stock fall 60% before the clock ran out. The tax break saved a little. The hold cost a lot.
Hybrids & more
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.
How equity comp is split in a divorce
Unvested grants are often marital property, dividing them is its own tax problem, and the real cost is the time.
Selling private shares in a tender offer: taxes and mechanics
An engineer sold a slice of his startup stock in a tender offer before the IPO. Here is how the window worked, what it taxed, and how he decided how much to sell.
Concentration risk calculator
See how much of your net worth is riding on a single company stock, and the line where it gets dangerous.
QSBS
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.
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.
Planning around QSBS: setup, stacking, and the 1045 rollover
The QSBS exclusion is mostly decided at the moment you get the stock, not the moment you sell. This is the planning playbook: lock in qualification early, multiply the cap with gifts and trusts, and use a Section 1045 rollover to rescue a forced early exit.
Does your state honor the QSBS exclusion
QSBS is a federal break, and states get a vote. California taxes the gain in full while New York generally follows the federal exclusion, so the same sale can split two ways.
Case study: a founder's QSBS exit, mostly tax-free
Five years held, the qualified small business stock exclusion claimed, and a large chunk of the gain off the table. The win was set up at incorporation, not at the sale.
QSBS and California
California ignores the QSBS exclusion entirely. A gain the IRS lets you exclude in full is taxed at up to 13.3 percent by California, and the only real fix is residency, set up years before you sell.