Post-IPO & public

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

RSUs

Recommended 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.

Explainer

How RSUs are taxed at an IPO

An IPO can detonate years of double-trigger RSUs into one tax year. The income stacks, the withholding falls short, and the bill arrives while the stock is still locked up.

Case study

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

Recommended Case study

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.

ESPPs

Recommended In-depth

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.

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.