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RSUs
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.
Case study: holding RSUs through an IPO
Double-trigger shares all settle at once, and a six-figure tax bill lands in one quarter.
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.
Restricted stock
ISOs
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.
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: 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: 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.
NSOs
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: 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.
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.
ESPPs
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.
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.
Hybrids & more
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.
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.