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Diversify concentration
RSUs
Case study: a full vesting year at a public company
An engineer with a large RSU year, and the tax bill nobody warned her about.
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.
Case study: holding RSUs through an IPO
Double-trigger shares all settle at once, and a six-figure tax bill lands in one quarter.
ISOs
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.
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.
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
ESPPs
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.
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.
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.
Should you fund your ESPP or hold cash for RSU taxes
When the ESPP and your RSU tax bill compete for the same paycheck, one of them is a near-certain return and the other is a bill you already owe. That settles the order.
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.
ESPP vs 401(k): where should the next dollar go
Both are good. They do different jobs, and the order you fund them in can leave real money on the table. Here is the priority I use.
Hybrids & more
Secondary sales and tender offers for private shares
How employees turn private stock into cash before an IPO, what the price really means, what it taxes, and how much you should actually sell.
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?
Concentration risk calculator
See how much of your net worth is riding on a single company stock, and the line where it gets dangerous.
Selling private shares in a tender offer: taxes and mechanics
An engineer sold a slice of his startup stock in a tender offer before the IPO. Here is how the window worked, what it taxed, and how he decided how much to sell.