Family, estate & charitable

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

RSUs

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Sell at vesting or hold? The complete RSU decision

Sell at vesting unless you can name a real reason to hold. This is the whole decision, start to finish: the default, how to fund the tax, when holding earns its keep, how to diversify a pile you already have, and how to give shares away without paying gains.

ISOs

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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.

NSOs

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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.

Hybrids & more

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How equity comp is split in a divorce

Unvested grants are often marital property, dividing them is its own tax problem, and the real cost is the time.

QSBS

Recommended Guide

What makes stock qualify as QSBS

QSBS is not a label you choose at sale. It is a stack of conditions your stock had to meet the day it was issued: the right entity, a small-enough company, original issuance straight from the company, a qualifying business, and a long enough hold.

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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.

Case study Start here

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.

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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.