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Defer & time it right

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Minimize immediate tax Defer & time it right Diversify concentration Family, estate & charitable Pre-IPO & private Post-IPO & public Life events

ISOs

Recommended Guide

How ISOs are taxed at exercise and sale

ISOs skip ordinary tax at exercise, but the disposition decides everything: clear both holding clocks and the whole gain is long-term capital gains, miss either and the spread becomes ordinary income.
Deep dive Start here

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.
Guide Start here

Planning the ISO exercise year

Exercise up to the point where AMT kicks in, early in the year, then stop and repeat. The whole strategy is choosing how much spread to recognize, when to hold, and when to sell, on purpose.

NSOs

Recommended Guide

How NSOs are taxed: the bargain element and everything after

The spread between the stock price and your strike at exercise is ordinary income, taxed like salary that year. Then the shares are just stock. This is the whole NSO tax picture: the spread, the payroll surtaxes, the withholding gap, your real basis, and the capital gain after.
In-depth Start here

NSO exercise strategy: when to exercise, hold or sell, and the moves around it

The one lever an NSO hands you is the calendar. This is the whole playbook: when to exercise, whether to hold or sell, how to spread it, how to fund the tax, and how to give the shares away.
Tool

Multi-year NSO exercise planner

Model exercising in chunks to keep each year out of the top bracket, using a bracket-headroom worksheet you can build by hand.
Case study

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

Case study: exercising NSOs during a sabbatical

A year off dropped the bracket, and a planned NSO exercise rode the savings down with it.

Hybrids & more

Recommended Guide

How SARs and phantom stock are taxed

Cash-settled equity looks like stock and gets taxed like salary. The whole payout is ordinary income the day it lands, there is no capital gains door, and the only real lever you have is timing.
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?

QSBS

Recommended Guide

QSBS (Section 1202): the complete guide

Qualified small business stock can erase the federal tax on a startup-stock sale, sometimes the whole thing. This is the full story: which rules apply to your shares, how the exclusion is sized, the holding clock, and the per-issuer cap that decides how much you actually shelter.
Guide Start here

Planning around QSBS: setup, stacking, and the 1045 rollover

The QSBS exclusion is mostly decided at the moment you get the stock, not the moment you sell. This is the planning playbook: lock in qualification early, multiply the cap with gifts and trusts, and use a Section 1045 rollover to rescue a forced early exit.