Startup equity taxes, explained in plain English
Every rule that touches your equity, with worked examples you can check. Start with the featured guide, then go deeper on your grant type or event.
Your Real Tax Rate on Equity: Effective vs. Marginal vs. Withheld
Three numbers get confused: your bracket, what was withheld, and what you actually pay. Here is how each equity event changes your real rate.
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Too Little Tax Taken Out? How to Spot and Fix Underwithholding
Your employer withholds a flat 22% on most equity income, but your real rate can be far higher. Here's how to spot the gap and close it.
Penalties for Paying Tax Late: Underpayment, Late-Payment and Late-Filing
Three different penalties can apply when tax is paid late. Here's what each costs and how the safe harbors keep you clear.
Buying Pre-IPO Shares on the Private Market: The Tax Basics
The IPO isn't a tax event for you. What matters is your purchase price, your purchase date and when you sell.
How commissions and bonuses are taxed and withheld
A commission check isn't taxed at a special rate, but it's withheld differently from your salary. Here's why big checks can look over-taxed, and why you may still owe in April.
How ESPP shares are taxed
Your ESPP discount is taxed when you sell, not when you buy. How much counts as salary depends on how long you held the shares.
W-4 Step 4(c): How to Add Extra Withholding and Close a Tax Gap
Step 4(c) on your W-4 lets you add a fixed extra amount to every paycheck. It's the simplest way to close a gap from RSUs, commissions or a planned stock sale, and the IRS treats it more kindly than a late estimated payment.
Pay the Tax When the Money Lands: Liquidity Events, Stock Sales, and the Lockup Cash Trap
A stock sale, tender offer, or IPO creates a tax bill the day it happens, but the bill often doesn't feel real until April. Here's why to pay it right away, and how to plan when your shares are locked up and the cash isn't there yet.
Can You Move to Florida or Texas to Avoid Tax on Your Stock?
Your equity was granted in one state and pays out after you move to another. Here's which state taxes what, why the move-to-Florida plan usually falls short, and the situations that catch people out.
RSU and Stock Option Taxes at IPO: What Employees Owe
What happens to your RSUs, options, and shares when your company goes public, why the 22% withholding usually falls short, and how to plan around the lockup.
When Your Startup Is Acquired: How Your Equity Is Taxed
An acquisition can pay you in cash, in the buyer's stock, or both, and some of it may come later. What you owe this year depends on what you hold and how the deal is built.
How Startup Equity Is Taxed: The Complete Guide to RSUs, ISOs and NSOs
Every type of equity is taxed at a different moment and at a different rate. Start here: what triggers tax for RSUs, ISOs and NSOs, and where the surprises hide.
Selling Company Stock? Why Nothing Is Withheld — and How to Pay the Tax Right Away
When your RSUs vest, your employer withholds tax. When you later sell those shares, nobody does. Here's why the gap happens and three ways to close it.
How RSUs Are Taxed: Vesting, Withholding and Selling
RSUs are taxed twice: as salary when the shares arrive, and as a capital gain on any growth after that. Here's how each step works.
The RSU Withholding Gap: Why 22% Usually Isn't Enough
Your employer withholds a flat 22% on RSUs. If you earn more than about $200,000, you probably owe far more, and the difference is due in April.
Double-Trigger RSUs at a Private Company: What Happens at IPO
Years of vested RSUs can become taxable on a single day, often before you're allowed to sell. Here's how to prepare.
How ISOs Are Taxed: Exercise, AMT and Qualifying Sales
ISOs offer the best tax treatment of any employee equity, but only if you meet two holding periods and survive the AMT. Here's the full picture.
ISO Exercises and the AMT: How to Estimate It and Get It Back
Exercising ISOs can create a large tax bill with no cash to pay it. Here's how AMT works in 2026, how to find your crossover point, and how the credit returns it.
How NSOs Are Taxed: Exercise, Withholding and Sale
With NSOs, the moment you exercise is the moment you owe tax, as ordinary income on the spread. Here's the math and how to plan it.
Early Exercise and the 83(b) Election
Early exercise plus an 83(b) election can lock in almost no tax today and start every holding clock. But you have 30 days, and the money is at risk.
IPO Lockups: How to Plan Your First Sale
When the lockup ends, you can finally sell. Decide before that day which shares to sell, how the gains are taxed, and how you'll pay the tax.
Tender Offers and Secondary Sales: How They're Taxed
A tender offer lets you sell before an IPO. Depending on what you sell, the proceeds can be a capital gain, wages, or both.
Moving States Before an IPO: How Equity Income Is Sourced
It's not the state you lived in when the grant was given. Pay from equity is taxed where you worked between grant and vest, and growth after that is taxed where you live when you sell.
Estimated Taxes and Safe Harbor for Equity Windfalls
A big equity year almost always means under-withholding. The safe-harbor rules tell you the minimum to pay during the year to avoid any penalty.
Leaving a Startup: Your Stock Option Exercise Deadline
When you leave, the clock starts. Most plans give you 90 days to exercise vested options or lose them. Here's how to decide.
QSBS (Section 1202): Excluding Gains on Startup Stock
If your shares qualify as QSBS, millions of dollars of gain can be federally tax-free. Here's who qualifies and how the new tiered rules work.
Long-Term vs Short-Term Capital Gains on Company Stock
One day can separate a 37% federal rate from 20%. Here's when your holding clock starts for each kind of equity, and the 2026 rates.
What the 2025 Tax Law Changed for Equity Holders in 2026
The tax law signed in July 2025 kept current rates but reshaped AMT, QSBS and the SALT deduction. Here's what matters if you hold equity.
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