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IPO

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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.
Explainer

How RSUs are taxed at an IPO

An IPO can detonate years of double-trigger RSUs into one tax year. The income stacks, the withholding falls short, and the bill arrives while the stock is still locked up.
Case study

Case study: holding RSUs through an IPO

Double-trigger shares all settle at once, and a six-figure tax bill lands in one quarter.

Restricted stock

Start here for this stage Case study

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 Case study

Case study: exercising pre-IPO ISOs

An early employee exercised before the IPO and made an AMT bet that paid off. The lesson is in why it worked, not that it did.
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.

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.