The Crossover

Exercising can create tax without cash. There’s a limit before it does.


The IRS computes your taxes under two systems and you pay whichever is higher. Exercising ISOs creates paper income that only the second system, the AMT, counts. You have a cushion before it owes anything, and the crossover is the share count where that cushion runs out. We find yours before you exercise a single share.

Estimated $0-Tax Exercise Limit · Tax Year 2026Sample data

15,294 shares

Exercise up to this many shares with the 409A at $19.00and an estimated $0 of additional tax.

Strike price · sample grant $2.00

Cash to exercise

$30,588

Sold to cover

1,610

Shares kept

13,684

Estimates from fictional sample data. Your actual crossover depends on income, filing status, state, deductions, prior exercises, and grant-level strike prices.

Your crossover is not a recommendation to exercise. It’s one boundary within a larger decision.

What You’d Keep · Same-Day SaleSample data

$3.57M

Gross proceeds

−$68K

Strike cost

−$1.28M

Estimated tax

$2.22M

Net after-tax

In a same-day exercise and sale, the bargain element is generally taxed as ordinary compensation income. Qualifying instead can change the outcome by six figures. The analysis quantifies both, plus partial sales from 20% to 100%.

The Liquidity Event

Selling into the event: what you’d actually keep.


If you exercise and sell as part of a tender offer, acquisition, or IPO, the full gain is taxed as ordinary income that year. The analysis maps the path from gross proceeds to net after-tax cash, shows how selling only part of the position can fund the taxes on the rest, and quantifies what holding to qualify would change.

Where We Fit

There is risk in exercising. There can be a cost to waiting.


Exercising ISOs means committing cash to company stock that may rise, fall, or stay illiquid. Waiting preserves flexibility, but it can delay important holding periods and reduce access to favorable tax treatment. We do not tell you whether the company is a good investment. We quantify what exercising now, gradually, or later would mean for your taxes and cash, because those choices have measurable value and expiration dates. Your financial advisor can help you weigh the investment risk, and together you decide with both sides of the picture.

The Deliverable

One example of what you’d get.


Every engagement produces a CPA-reviewed report built from your real grants, income, and filing status — crossover, liquidity, or several scenarios side by side, depending on what you’re deciding. Below is a sample of the crossover report, so you can see the format before you share anything real.

Common Questions

“What the hell’s an ISO?” Fair question.


Thirteen plain-English answers — from what an ISO actually is, to what happens when you sell, to how we start. No jargon, no judgment.

Whatever you’re deciding, start with the number.

A 30-minute conversation is enough to know what you actually need. No pressure, no jargon, just a clear read on your situation.

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