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Filter across every equity type at once. Combine a lifecycle stage with a tax concept, a strategy, and a format to find exactly what fits your situation.
RSUs
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 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 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.
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.
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.
2026 RSU supplemental withholding rates
The flat supplemental rates that apply to your 2026 vests, and why they often under-withhold.
Case study: holding RSUs through an IPO
Double-trigger shares all settle at once, and a six-figure tax bill lands in one quarter.
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.
How to value an RSU offer against base salary
Discount the equity for vesting risk and volatility before you compare two job offers.
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.
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.
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.
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.
Restricted stock
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.
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.
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.
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.
Should you file an 83(b) election? The decision and the breakeven
For early-stage stock worth almost nothing, filing the 83(b) is close to a no-brainer. It only gets hard once the shares carry real value and the tax you prepay stops being a rounding error. The breakeven is the price where prepaying finally beats waiting.
2026 update on filing the 83(b) election
The current filing and proof rules for an 83(b) election, including the IRS's official Form 15620. The 30-day clock has not budged.
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.
Profits interests vs equity at an LLC
The startup-equity cousin that works very differently for tax. A profits interest can be worth zero today and still hand you real upside later.
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.
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.
ISOs
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.
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.
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.
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.
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: 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 90-day scramble after leaving
An employee left with $90k of in-the-money ISOs and 90 days to find the cash, or lose them.
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.
ISO AMT estimator
Estimate the alternative minimum tax a planned ISO exercise would trigger this year, before you write the check to exercise.
ISO exercise cost calculator
Add up the strike price and the AMT so you know the full cash cost of exercising your ISOs, not just the sticker price.
NSOs
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 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.
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 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.
Case study: an advisor's NSOs taxed on a 1099
No employer withholding meant the entire tax bill on the spread came due at filing, with nothing set aside.
Case study: exercising NSOs during a sabbatical
A year off dropped the bracket, and a planned NSO exercise rode the savings down with it.
Case study: spreading NSOs across three years
How staging exercises across three years kept one engineer out of the top bracket and saved five figures.
Early-exercising NSOs and the 83(b) election
Exercise before vesting while the spread is tiny, file an 83(b), and you tax the gain now at a near-zero number instead of later at a big one. The risk is real cash on stock that can go to zero.
Multi-year NSO exercise planner
Model exercising in chunks to keep each year out of the top bracket, using a bracket-headroom worksheet you can build by hand.
NSO exercise calculator
Estimate the spread, the tax, and the cash you actually need to exercise, in four numbers you can do on a napkin.
State taxes on NSOs when you change states
Move to a no-tax state and you still owe the old state on the part of the spread you earned there. The income follows the workdays, not your new address.
ESPPs
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.
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.
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.
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.
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: 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.
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.
ESPP cost basis adjustment calculator
Work out your corrected basis so you do not pay tax on the discount twice.
ESPP return calculator
See the annualized return on your ESPP after the discount, lookback, and tax.
ESPP vs 401(k): where should the next dollar go
Both are good. They do different jobs, and the order you fund them in can leave real money on the table. Here is the priority I use.
How to fund a maxed ESPP without the cash on hand
Maxing the plan means a chunk of every paycheck vanishes for months before you see stock. Here is how to bridge that gap without taking on risk that eats the discount.
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.
Should you fund your ESPP or hold cash for RSU taxes
When the ESPP and your RSU tax bill compete for the same paycheck, one of them is a near-certain return and the other is a bill you already owe. That settles the order.
Hybrids & more
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.
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 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.
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?
Case study: a SAR payout at a private company
Cash settled at a tender offer, taxed entirely as ordinary income, with a withholding gap that landed in April.
Concentration risk calculator
See how much of your net worth is riding on a single company stock, and the line where it gets dangerous.
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.
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.
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.
QSBS
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.
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.
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.
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.
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.
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.
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.