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Mergers & acquisitions

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RSUs

Start here for this stage In-depth

How RSUs work

An RSU is a promise of shares once you vest. That one fact, the gap between the promise and the shares, decides when you owe tax, what you own, and what you walk away with if you leave.
In-depth Start here

The RSU tax traps that hit in April, and how to dodge them

The flat rate your company withholds at vesting is almost always lower than what you owe, and that gap is just the first of the RSU traps. This is the complete field guide: the withholding gap, estimated taxes, the double-taxed 1099-B, short-term gains, blackouts, wash sales, acceleration, and the private-company bill on shares you cannot sell.

Restricted stock

Start here for this stage Explainer

Restricted stock in an acquisition

When your company gets bought, your restricted stock can cash out, convert to acquirer shares, or roll into new vesting. Which one you get, and whether your unvested shares accelerate, decides what the deal actually pays you.
Case study Start here

A founder's restricted stock, start to exit

Follow one founder's restricted stock from incorporation to acquisition, and watch how a single form filed in week one decides what the exit actually pays. The tax fork happens at the beginning, not the end.

ISOs

Start here for this stage Deep dive

ISOs and the AMT: the complete guide

Exercising and holding ISOs can hand you a cash tax bill on a gain you never sold, and this is the whole story of how that happens and how to plan around it.
Case study

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.

Hybrids & more

Start here for this stage Case study

A phantom stock payout at a private company

An executive watched her phantom units pay out at a sale, then learned the whole check was wages. A walk through what landed, what was withheld, and what she owed.
Guide Start here

When cash-settled equity beats real shares

Real shares win on taxes almost every time. So why take SARs or phantom stock, and once you have them, how do you plan a payout you mostly cannot control?
Case study

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.

QSBS

Start here for this stage Case study

Case study: a founder's QSBS exit, mostly tax-free

Five years held, the qualified small business stock exclusion claimed, and a large chunk of the gain off the table. The win was set up at incorporation, not at the sale.