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Equity compensation, in depth
Plain-English walkthroughs of the topics our calculators run on. Written for tech employees with real equity at stake, with the math, the trade-offs, and the landmines spelled out.
Alternative Minimum Tax
How to find your ISO AMT crossover point (2026)
Your AMT crossover is the largest ISO exercise you can make in a year before alternative minimum tax adds to your bill. The math, the four traps, the calculator.
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Alternative Minimum Tax
AMT credit recovery in plain English
The alternative minimum tax (AMT) you pay on an exercise-and-hold ISO is mostly a prepayment, not a cost: Form 8801 carries it forward as a credit against future regular tax. The catch is the pace. A single filer earning $250,000 claws back about $14,900 a year, so a $134,654 credit takes nine-plus years unless something changes. Here are the mechanics, what speeds them up, and how the calculator schedules around them.
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Alternative Minimum Tax
Form 6251, walked through with a real ISO exercise
Form 6251 is where the alternative minimum tax (AMT) actually happens: a second computation of your entire federal tax that adds your incentive stock option (ISO) bargain element back on line 2i and bills the excess on line 11. We fill it in with one real exercise: 10,000 ISOs at a $5 strike and $50 fair market value, on $250,000 of income, end at $134,654 of AMT, due in cash before the shares are ever sold.
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Private-company liquidity
Pre-IPO secondary sales: the tax mechanics
A tender offer is often the only liquidity window a private company opens before the IPO, and what you keep depends on what you sell into it. Already-exercised incentive stock options (ISOs), unexercised options, restricted stock units (RSUs), and qualified small business stock (QSBS) each carry different tax mechanics; the wrong lot converts long-term gains to ordinary income or breaks a five-year clock. The price and the deadline are fixed for you. Which shares to sell is the decision, and it is tax math.
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Non-qualified stock options
NSO exercise: sell now or hold for long-term capital gains?
Sell at exercise, for most people: the NSO bargain element is taxed as ordinary income either way. The decision framework, plus six traps that cost real money.
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Restricted stock units
Sell RSUs at vest or hold? And why 22% withholding isn't enough
Sell RSUs at vest, for most people: the tax is locked in either way. And 22% withholding is not enough at a 32-35% marginal rate. Find your specific April gap.
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Concentration and diversification
How much of your net worth should be in one stock?
Above 10% of liquid net worth, a single stock is worth managing; above 25% it shapes your outcomes. How to diversify without losing half your gains to tax.
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Concentration and diversification
Exchange funds: are they actually worth it?
Contribute appreciated stock to a pooled fund, receive a diversified basket, pay no tax on the swap: that is the exchange fund pitch. The structure works, but you pay with a seven-year hold, fee drag on the whole position, and a tax bill that is deferred, not erased. It earns its keep for a narrow profile: very low basis, very large position, no cash need for seven-plus years. For most equity holders, a scheduled sell-down wins. Here is the comparison the pitch leaves out.
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Hedging concentrated positions
How a zero-cost collar works on concentrated stock
A zero-cost collar pairs a protective put with a sold call that pays for it: downside floored, upside capped, no cash outlay. How it compares to a plain protective put and a lower-cost put spread, and what each costs.
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Founder & employee stock
Does your stock qualify for QSBS? The Section 1202 tests (2026)
Stock that clears the eight Section 1202 tests makes the first $10-15 million of gain federally tax-free. The tests, the cap math, and five ways to lose it.
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Cashing out stock
Cashing out stock for a goal? Convert your risk tolerance into cash.
Selling vested stock for a house, tuition, or a sabbatical seems simple: sell enough to hit the number. But two people selling the same shares at the same price can keep very different amounts. We calculate whether the extra cash from waiting is worth the risk, then return the lowest-tax sell schedule to get there.
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Selling as an insider
10b5-1 plans for tech employees and Section 16 officers
Rule 10b5-1 lets you commit to a sell schedule while you are clean of material nonpublic information, then trade on autopilot, even through blackout windows. Since the December 2022 amendments the defense comes with real machinery: 30-to-120-day cooling-off periods, a no-overlap rule, officer certifications, and quarterly disclosure. The legal wrapper is the easy part. The schedule inside it, how many shares, which lots, which months, is a math problem you commit to in advance, so compute it before you sign.
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Equity compensation
Planning RSUs, ISOs, and NSOs together across tax years
When you hold all three grant types at once, the tax on each one depends on the others. This is the order of operations for sequencing restricted stock units, incentive stock options, and non-qualified options across multiple years, plus the free calculators for each piece.
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Restricted stock units
Which RSU lots should you sell first?
Diversifying a concentrated stock position? The lots you sell, and the years you sell them in, change the tax bill. Specific identification, long-term timing, and bracket spreading, versus your broker's first-in-first-out default.
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Compare
OptionsAhoy alternatives: equity planning tools and services compared
Secfi’s calculators, Carta’s and ESO Fund’s AMT estimators, Equity Simplified, advisor software, wealth managers: this page compares products that share OptionsAhoy’s objective, planning your equity. Products with different objectives (financing an exercise, pooling shares, managing wealth at large) are out of scope no matter who sells them. Head-on tables, when each alternative is the better choice, and every factual claim linked to its source.
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Compare
Free AMT calculators compared: estimating a year vs. optimizing the schedule
Carta, ESO Fund, Equity Simplified, Secfi, and OptionsAhoy all publish free AMT calculators. The real difference is not accuracy, it is scope: most estimate one year of alternative minimum tax for one exercise, and one computes the multi-year exercise schedule that minimizes it. Here is what each tool does, when a single-year estimate is enough, and what it cannot see.
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Compare
ISO exercise planners compared: scenarios you pick vs. a computed optimum
Every ISO exercise planner answers "what if I exercise now vs. later?" The dividing line is what gets searched. Scenario tools (Secfi’s Equity Planner) evaluate the plans you think to try; single-position planners (Equity Simplified) compute exercise amounts against AMT for one year; OptionsAhoy’s optimizers search the space of multi-year plans and return the best one they can prove. Here is who makes what, and when each approach is the right one.
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Compare
RSU calculators compared: vest math, sell-vs-hold, and lot order
Most RSU calculators answer one question: what is this vest worth after taxes? That is the easy third of the problem. The decisions that move real money are whether to hold after vest (the sell-vs-hold cliff at 12 months) and which lots to sell first when unwinding a position. Here is what each free tool computes, and which decisions each one can and cannot answer.
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Calculators
Run the numbers on your own grant
Every article above pairs with a free calculator that takes your grant data and produces an answer. No signup.