Browse topics
By lifecycle stage
Vesting
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.
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: a full vesting year at a public company
An engineer with a large RSU year, and the tax bill nobody warned her about.
2026 RSU supplemental withholding rates
The flat supplemental rates that apply to your 2026 vests, and why they often under-withhold.
State tax on RSUs when you move states
Move to a no-tax state and your RSUs do not all become tax-free. The state where you worked while they vested can still tax that slice of the income.
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 tax estimator
A simple way to estimate the tax on a vesting year and the shortfall your withholding leaves behind. The interactive version is on the way.
RSU withholding gap calculator
See how much your company under-withheld on a vest and what to set aside before April.
RSU net shares after withholding calculator
Estimate how many shares you actually keep once taxes are withheld at vest.
RSU sell-or-hold after-tax calculator
Compare selling at vest against holding, after tax and after concentration risk.
Laid off with unvested RSUs on the table
What one worker actually kept after a layoff, and the one severance term that saved part of the pile.
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
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.
Missing the 30-day 83(b) deadline (and skipping it on purpose)
The 83(b) election has a hard 30-day window and no late forgiveness. Miss it, or skip it, on early-stage stock and you can hand the IRS a tax bill that grows every year the company does well, on shares you cannot sell to pay it.
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.
RSAs vs RSUs: the differences that actually matter
An RSA is real stock you own at grant; an RSU is a promise of stock later. That one distinction decides whether you can file an 83(b), when you owe tax, and whether you vote your shares from day one.
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.
Case study: the missed 83(b) that cost six figures
An early hire skipped the form, then vested into a unicorn valuation. The tax bill arrived years before any chance to sell.
ISOs
NSOs
ESPPs
Hybrids & more
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.
A phantom stock payout at a private company
An executive watched her phantom units pay out at a sale, then learned the whole check was wages. A walk through what landed, what was withheld, and what she owed.
When cash-settled equity beats real shares
Real shares win on taxes almost every time. So why take SARs or phantom stock, and once you have them, how do you plan a payout you mostly cannot control?
How SARs and phantom stock show up on your W-2
Both land in your wages, taxed like a bonus, and the withholding usually falls short of what you owe.