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Post-sale & reinvestment

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RSUs

Start here for this stage In-depth

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

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: a disqualifying ISO sale to diversify fast

Why one founder chose ordinary income over holding a single volatile stock for the lower rate.

ESPPs

Start here for this stage Explainer

Keeping ESPP shares from concentrating your portfolio

The discount is real, but every share you keep stacks more of your net worth on the one stock that already signs your paycheck. Here is how to take the deal without taking the bet.

QSBS

Start here for this stage Explainer

Reporting a QSBS exclusion on your return

The QSBS break is not automatic on your tax return. You report the full sale, then back the exclusion out with the right code, or the gain stays taxed.
Guide Start here

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.
Explainer Start here

How people accidentally blow their QSBS

Most QSBS gets lost by accident, not by bad luck. A redemption, an early sale, the wrong entity, a secondary purchase, or missing records can quietly kill a break worth more than the mistake ever felt at the time.
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.
Explainer

QSBS and California

California ignores the QSBS exclusion entirely. A gain the IRS lets you exclude in full is taxed at up to 13.3 percent by California, and the only real fix is residency, set up years before you sell.