All Calculators — Cliff & Vest

01 Calculator 83(b) Election Calculator Filing an 83(b) election taxes you now, on today’s value, instead of at each vesting date on whatever the shares are worth then. Usually that is a large win. Occasionally it is a disaster you cannot undo. This prices both paths. Lifetime tax saved by electing · Tax due within 30 days
02 Calculator AMT Credit Recovery Calculator Paying alternative minimum tax on an ISO exercise creates a minimum tax credit that never expires. It also never arrives all at once. §53 releases it only in years where your regular tax exceeds your tentative minimum tax, which for most people is a few thousand dollars a year — until the shares are sold. Years to recover it all · Credit you can claim each year
03 Calculator ESPP Disposition Calculator Sell your employee stock purchase plan shares too early and the whole discount is ordinary income — even if you sold at a loss. This works out what each path costs, and whether holding on is actually worth it. Tax this sale costs you · Net proceeds after tax
04 Calculator Exercise Financing Break-Even Calculator Non-recourse lenders will pay your strike price and your tax bill in exchange for interest and a share of the upside. Whether that is a lifeline or an expensive mistake depends on the exit price — and the honest comparison is not against paying cash, but against doing nothing at all. Net if you pay cash · Net if you finance
05 Calculator ISO AMT Calculator Exercising an incentive stock option produces no regular taxable income and can still produce a very large tax bill. This works out the alternative minimum tax, the total cash you need, and the largest exercise you can make without triggering AMT at all. AMT caused by this exercise · Total cash needed
06 Calculator NSO Exercise Cost Calculator Exercising a non-qualified stock option is a taxable event the moment you do it. Your company has to collect the withholding before it will issue the shares, so the bill is not deferred to April — it is due now. This works out how much, and whether you can cover it. Cash needed on the day · Shares to sell to cover it
07 Calculator Offer Comparison Calculator An offer letter values your equity at shares times today’s price. That figure ignores the strike you have to pay, the tax you will owe, and the possibility that a private company’s shares end up worth nothing. This prices both offers on the same basis. Advantage to Offer A · Offer A’s equity must be this likely to tie
08 Calculator QSBS Eligibility & Exclusion Calculator Section 1202 can exclude millions of dollars of gain from federal tax entirely. It is also the most conditional provision an ordinary shareholder will ever meet: six tests, two entirely different regimes depending on whether you acquired the stock before or after 4 July 2025, and a rate trap in the middle of the new one. Share of gain excluded · Tax saved by qualifying
09 Calculator RSU Withholding Shortfall Calculator Your employer withholds a flat 22% on vesting RSUs regardless of what you actually earn. If your real rate is 32% or 35%, the difference is a bill you meet in April. This works out exactly how large it is. Additional tax you will owe · Shares to sell to cover it
10 Calculator Tender Offer & Secondary Sale Calculator A tender offer is usually the first time startup equity turns into money. What you keep depends far less on the price than on what you were holding when the offer arrived — and on whether anything was withheld before the cash reached you. Net cash you keep · Cash that reaches you at closing