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Holding period
RSUs
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.
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.
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.
RSU sell-or-hold after-tax calculator
Compare selling at vest against holding, after tax and after concentration risk.
Restricted stock
ISOs
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.
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.
How ISOs work
Incentive stock options can turn your entire gain into long-term capital gains, no ordinary income at all. The path is narrow, every step has a deadline, and this is the whole map from grant to sale.
Case study: the AMT trap when the stock crashed
A worker owed AMT on a paper gain, then the shares fell 70%. Here is what he did next and what would have saved him.
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.
NSOs
NSO traps: the double-counted basis, the cash bills, and the deadlines that kill grants
The expensive NSO mistakes are quiet ones. The double-counted 1099-B basis taxes you twice, under-withholding ambushes you in April, illiquid stock owes cash you can't raise, and two deadlines erase winning options. Here is all of it.
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.
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.
ESPPs
ESPP reporting: Form 3922, Form 8949, and the basis fix
The form your employer sends, the forms you file, and the one adjustment that keeps you from paying tax on your discount twice. A full walkthrough with a worked example and a pre-sale checklist.
The ESPP mistakes that quietly cost you money
From selling a few days early to paying tax twice on your discount, the ESPP punishes small oversights. Here is the full list of the traps and how to dodge each one.
Case study: two years of ESPP, two outcomes
Same plan, same employee. One year she sold at purchase. The next year she held for the tax break. Here is which one came out ahead.
How an ESPP works: the complete guide
An employee stock purchase plan lets you buy company stock at a discount, often with a lookback that quietly doubles the deal. For most people who have one, it is the best return available at work, and this is the whole story of how it runs.
Is maxing out your ESPP worth it
With a real discount and a quick sale, an ESPP is often the highest-return benefit you have. This is the whole playbook: whether to max it, how to fund it, when to sell, and the rare case for holding.
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.
Case study: holding ESPP shares straight into a crash
He held for the lower tax rate and watched the stock fall 60% before the clock ran out. The tax break saved a little. The hold cost a lot.
Hybrids & more
QSBS
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.
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.
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.
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.
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.